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In this episode, Jason and Rippling's Senior SDR Director, Bert Brokaw, talk about what it really takes to crush the Director of SDR role, from leading managers and aligning with executives to building a high-performing outbound culture. Tune in to learn how top leaders grow strategic SDR teams that consistently deliver results. ‍ Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

Miles Clements is a Partner @ Accel where he helps to lead their growth fund. At Accel, Miles has led or invested in Atlassian, Cursor, Linear, and more.  AGENDA:  03:38 Where is True Alpha and Value in a World of AI  05:10 Why it is Total BS that Cursor is Dead 07:55 Why Cursor Were Not Wrong to Build Their Own Models 09:38 What is the Upside When Investing in Cursor at $27BN? 15:12 Do Sub $10BN Outcomes Even Matter to a Fund the Size of Accel? 17:07 Losing ServiceTitan: Investing Lesson Learned… 19:55 Missing Rippling: What We Learned 27:20 What is Accel's Win Rate 30:22 How VCs Approach Ownership Has Changed 35:09 Does Miles Feel Happier or Sadder to be an Anthropic Investor Post Pentagon Debacle 36:45 What Happens to Companies Like Miro and Snyk with High Prices to Live Upto? 38:05 Why it is a Great Time to Be Thoma Bravo and Vista  38:36 Why Founder-Led Companies Are Always Better 41:12 Why Would Any Founder Go Public Today 43:48 When is the Right Time to Take Chips Off The Table? 45:24 Should VC Firms Have Evergreen Funds and Be Responsible for Public Positions 50:28 You Can Pick Any VC to Join Accel, Who Does Miles Choose…     

TRANSCRIPT Robertson: [00:00:00] Gissele: Hello and welcome to the Love and Compassion podcast with Gissele. We believe that love and compassion have the power to heal our lives and our world. Gissele: Don’t forget to like and subscribe for more amazing content. And if you’d like to support the podcast, please go to buy me a coffee.com/love and compassion. Today we’re talking about how to become a more compassionate civilization in light of the world’s most recent events. Robertson Work is a nonfiction author, social ecological activist, and former UNDP policy advisor on decentralized government, NYU Wagner, graduate School of Public Service, professor of Innovative Leadership and Institute of Cultural Affairs, country Director, conducting community organizational and leadership initiatives. Gissele: He has worked in over 50 countries for over 50 years and is founder of the Compassionate Civilization Collaborative. He has five published books and has [00:01:00] contributed to another 13. His most well-known book is a Compassionate Civilization. Every week he publishes an essay on Compassionate Conversations on Substack. Gissele: Please join me in welcoming Robertson work. Hi Robertson. Robertson: Hi Giselle. How are you? Gissele: I’m good. How about yourself? Robertson: I’m good, thank you. I here in the Southern United States. I’m glad you’re in wonderful Canada. Robertson: great admiration for your country. Gissele: Ah, thank you. Thank you. Gissele: I wanted to talk about your book. I got a copy of it and it was written in 2017, but as I was reading it, I really found myself listening to things that were almost prophetic that seemed to be happening right now. What compelled you to write Compassionate Civilizations at this moment in history. Robertson: Yes. Thank You you so much, and thank you for inviting me to talk with you today. Robertson: And I wanna say I’m so touched by the wonderful work of the Matri Center for Love [00:02:00] and Compassion. I have enjoyed looking at your website and listening to your podcast and hearing Pema Chodron speak about self-love. If it’s okay, I’d like to start with a few moments of mindful breathing Gissele: Yes, definitely. Robertson: okay. I invite everyone to become aware of your breathing, being aware of breathing in and breathing out. Breathing in the here and in the now. Breathing in love. Breathing in gratitude. I have arrived. I am home. I’m solid. I am free breathing in, breathing out here now. Robertson: Love [00:03:00] gratitude. Arrived home solid free. Okay. And to your question, after working in local communities and organizations around the world with the Institute of Cultural Affairs and doing program and policy work with UNDP and teaching grad school at NYU Wagner, I felt called to articulate a motivating vision for how to embody and catalyze a compassionate civilization. Robertson: So each of us can embody, even now, even here, we can embody and catalyze a compassionate civilization in this very present moment. We don’t have to wait, you know, 50 years, a hundred years, a thousand years. we can embody it in the here and the now. So I was increasingly aware of climate change, climate disasters, [00:04:00] the rise of oligarchic, fascism, and of course the UN’s sustainable development goals. Robertson: I also had been studying the engaged Buddhism of Thich Nhat Hahn for many years, and practicing mindfulness and compassionate action. As you know, compassion is action focused on relieving suffering in individual mindsets and behaviors, and collective cultures and systems. The word that com it means with, and compassion means suffering. Robertson: So compassion is to be with suffering and to relieve suffering in oneself and with others. So, I gave talks about a compassionate civilization in my NYU Wagner grad classes and in speeches in different countries. Then in 2013, I started a blog called The Compassionate Civilization. So in 2017, there was a [00:05:00] new US president who concerned me deeply and who’s now president again. Robertson: So a Compassionate Civilization was published in July of that year, as you mentioned, 2017. The book outlines our time of crisis and provides a vision, strategies and tactics of embodying and catalyzing a compassionate civilization, person by person, community by community. Moment by moment it it includes the movement of movements, mom that will do that. Robertson: Innovative leadership methods, global local citizen, and practices of care of self and others as mindful activists. So there’s a lot in it. Yeah. The Six strategies or arenas of transformation are environmental sustainability, gender equality, socioeconomic justice, participatory governance, cultural tolerance and peace, and non-violence, socio. Robertson: So since then [00:06:00] I’ve been promoting the Compassionate Civilization Collaborative, as you mentioned, to support a movement of movements. The mom, Gissele: thank you for that. I really appreciated that. And I really enjoyed the book as well. It’s so funny that, the majority of people see a world that doesn’t work and they want things to change, but they don’t do something necessarily to change it. When did compassion shift from a private virtue to a public mission for you? Robertson: Great question. Thank you. I think it began the private part began very early in my Christian upbringing. I was raised by loving parents to love others. You know, love of neighbor is the heart of Christianity. And understand that love is the ultimate reality. You know, that you know, as we say in Christianity, God is love. Robertson: So then when I went off to college at Oklahoma State University, I found myself being a campus activist. So I shifted to activism for civil rights. We were [00:07:00] demonstrating for women’s rights and for peace in Vietnam. As you know, the Vietnam War was raging. And after that, I attended Theological Seminary at Chicago Theological Seminary, but. Robertson: My calling happened when I was still in college, and it was in a weekend course, just a one weekend in Chicago. Some of us drove up and attended a course at, with the ecumenical Institute in the African-American ghetto in Chicago. And my whole life was changed in one weekend. I mean, I woke up that I could make a difference and I could help create a world that cared from everyone, you know? Robertson: And here I was. I was what? I was a junior in college. So then after that, I worked after college and grad school. I worked in that African American ghetto in Chicago with the Ecumenical Institute. And then in Malaysia, I was asked to go to Malaysia and my wife and I did [00:08:00] that, Robertson: And then. We were asked to work in South Korea, which we did. And then the work shifted from a religious to secular is we now call our work the Institute of Cultural Affairs. And from there we worked in Jamaica and then in Venezuela, and then back in the US in a little community in Oklahoma Robertson: And then I also worked in poor slums and villages. So then with the UNDP. I worked in around the world giving policy advice and starting projects and programs on decentralized governance to help countries decentralize from this capital to the provinces and the cities and towns and villages to decentralize decision making. Robertson: Then my engaged Buddhist studies particularly with Han and his teachers and practice awakened me to a calling to save all sentient beings. what [00:09:00] an outrageous calling, how can one person vow to save all sentient beings? But that’s what we do in that tradition of the being a BofA. Robertson: So through mindfulness and compassionate actions. So then I continue my journey by teaching at NYU Wagner with grad students from around the world. I love that so much. Then to the present as a consultant, speaker, author, and activist locally, nationally, and globally. So Gissele has been quite a journey, and here we are in this moment together, in this wild, crazy world. Gissele: Yeah, for sure, One of the things that I really loved about your book that you emphasize that we need to have a vision for the world that we wanna create. If we don’t have a vision, then we can’t create it, right? many of us are, focusing on anti, anti-oppressive, anti crime, anti this, anti that. Gissele: But we’re not really focusing on what sort of world do we wanna create? and I’ve had conversations with so many people, and when I ask the question, if people truly [00:10:00] believe. The human beings could be like loving and compassionate, and we could create a world that would be loving and compassionate for all many people say no. Gissele: And so I was wondering, like, did you always believe that civilization could be compassionate or did you grow into that conviction? Robertson: Great question. I definitely grew into it. Yeah. even as a child, I was awakened, you know, by the plight of African Americans in my country, in our little town in Oklahoma. Robertson: So I kind of began waking up. But I wasn’t sure, how much I or we could do about it. So I really grew into that conviction through my journey around the world working in over in 55 countries, it’s interesting the number of people your podcast goes to serving people and the planet. Robertson: So. Everywhere I worked Gissele, I was touched by the local people, that people care for each other, you know, in the slums and squatter settlements, in villages, in cities, the, the rich and the [00:11:00] poor. everywhere I went regardless of the culture, the language, the races, the issues the, the local people were caring. Robertson: So my understanding is that compassion is an action. It’s not just a feeling or a thought. It’s an action to relieve suffering in oneself and in others. but suffering is never entirely eliminated. You know, in Buddhism, the first noble truth is there is suffering, and it continues, but it can be relieved as best we can with through practices, through projects, through programs, and through policies. Robertson: So what has helped me is to see, again, a deep teaching in Buddhism that each person is influenced by negative emotions of greed, fear, hatred, and ignorance. And yet we can practice with these and to become aware of them and just, and to let them go, you know, and to practice evolving into loving kindness as [00:12:00] you, as you do in in your wonderful center. Robertson: Teaching more loving, kindness, trust and understanding. We can embrace inner being that we’re all part of everything. We’re all part of each other. You know, we’re part of the living earth. We’re part of humanity. I am part of you, you are part of me. And impermanence, you know, that there is no separate permanent self. Robertson: Everything comes and goes, and yet the mystery is there’s no birth and death. ’cause you and I. we’re part of, this journey for 13.8 billion years of the universe, and yet we can, in each moment, we can take an action that relieves our own suffering and in others. So, as you said, a vision is so, so important. Robertson: I’m so glad you touched on that, that a vision can give us a calling to see where we can go. It can motivate us, push us, drive us to do all that we can to realize it, you know, if I have a vision for my family. To care for my family. If [00:13:00] I have a vision for my country, if I have a vision for planet Earth, that can motivate me to do all I can do to make that really happen. Robertson: So right now there are so many challenges facing humanity, climate disasters. Oh my, I’m here in Swanno where we’ve had a terrible hurricane in 2024. We’re still recovering from it. Echo side, you know, where so many species are dying of plants and animals. It’s, it’s one of the great diebacks of in evolution on earth, oligarchic, fascism. Robertson: Right now, we’re in the midst of it in my country. I can’t believe it. You know, you’re, you’re on 81. I, I thought I was, gonna die and still live in a country that believed in democracy and freedom and justice. And so now here we, I have to face what can I do about oligarchic, fascism and social and racial and gender injustice. Robertson: Other challenges, warfare. And here we are in this crazy, monstrous war [00:14:00] in the Middle East. You know, what can we do? What can I unregulated? Artificial intelligence very deeply concerns me. we’ve gotta regulate artificial intelligence so it doesn’t hurt humans and the earth. Robertson: It doesn’t just take care of itself. So, you know, it’s easy Gissele to be despairing and to give up, you know, particularly at this moment. But actually at any time in our life, we’re always tempted to say, oh, well, things will be okay, or There’s nothing I can do, you know, but neither of those is true. Robertson: There are things we can do. We can stop and breathe and continue doing what we can where we are. with what we have and who we are. We do not have to be stopped by despair or by cynicism or by hopeism. We don’t. So thank you for that question about vision. I vision still wakes me up every day and calls me forward. Robertson: I’m sure it does. You as well. Gissele: Yeah. I [00:15:00] mean, without vision, it’s like you don’t have a map to where you’re going to, right.what’s our destination if we don’t have a vision? And so this is for me, why I loved your book so much. you are helping us give a vision Gissele: I mean, the alternative is what is the alternative? there’s my next question. What happens to a society that abandons compassion? Robertson: Exactly. Well, I sort of touched on it before. it falls into ignorance and into greed. Wanting more wealth, more power. for me for my tribe and, and falls into hatred, falls into fear, falls into violence, and that’s happening now, she said. Robertson: But I love what Thich Nhat Hahn reminds us of, of is that if there is no mud, there is no lotus. And that, that means is, you know, if there is no suffering, there can be no compassion . So without suffering and ignorance, there is no compassion or wisdom, because suffering calls us to relieve it. when I see [00:16:00] my wife or children in pain, I want to help them. Robertson: or when I see others, neighbors, you know, during the pandemic, our neighbors took food and water to each other. You know, after the hurricane, neighbors brought us water. suffering calls the best from us, it can, it can also call, call other things. But again, there’s no mud. Robertson: The lotus cannot grow. So we can continue the journey step by step and breath by breath. So that’s what I’d say for now. but that’s an important question. Gissele: you said some key things including that, people have a choice. They can choose to be compassionate, or they can choose to use that fear for something else, right. Gissele: But I often hear from people, well, you know, they want institutions to change. why are the institutions more, equitable, generous, compassionate and you know, like. I don’t know if we have a vision for what compassionate institutions look like, [00:17:00] what would compassion look like at that level? Robertson: Oh, that’s where those six areas you know, the compassion would look like practicing ecological regeneration or sometimes called environmental sustainability. You know, that we we’re part of the living Earth gazelle, We’re not separate from the earth . We breathe earth air, we drink earth water. Robertson: We you know, the earth. Hurricanes come. The earth. Floods come We are earthlings. I love that word, earthlings, and so, how do we help regenerate the earth as society? And that’s why, you know, legislation aware of climate change, you know, to reduce carbon emissions. Robertson: The Paris Accord, and that’s just one example, how do we have all laws for gender equality so that women receive the same salaries as men and have the same rights. as men, we gotta have the laws, the institutions you know, and the participatory democracy, that we have a constitution. Robertson: a constitution is a vision. of what we are all about. Why are, we’re [00:18:00] together as a country, so that we can each vote and express our views and our wishes, and that government is by foreign of the people. It is. So it’s, it’s critical, you know, that we vote and get out the vote again and again and again. Robertson: And to create those laws, those institutions they care for everyone. And the socioeconomic justice. we need the laws and institutions that give full rights to people of color to people of every culture and every religion, and every gender every transgender, every human being, every living being has rights. Robertson: That’s why the Universal Declaration of Human Rights is so important. I’m so grateful that it was created earlier in the last century in my country our country cannot go to war without congressional approval. Robertson: Aha. did that just not happen? Yes. But it’s in the Constitution. the law says that we must talk about it [00:19:00] first. We must send the diplomats. We must doeverything we can before we harm anyone. War is hell. there are other ways of dialogue and diplomacy. Robertson: we can do better. But again, it takes the laws and institutions. Gissele: thank you for that. I do think that we have some sort of sense in terms of what we find doesn’t work for us, right? these institutions don’t work, they’re based on separation, isolation, punishment, and we see that they don’t work. We see that, like inequality hurts everyone. Gissele: We see that all of these things that we’re doing have a negative impact, including war. And yet we don’t change. What do you think prevents societies from becoming more compassionate? Robertson: if we’re in a society that if harming people through terrible legislation and laws and policies that makes it hard for people then have to either rebel and then they can be you know, killed. Or they have to form movements peaceful movements like the [00:20:00] Civil Rights Movement in my country, you know, with Martin Luther King leading peace marches and our peaceful resistance, in Minneapolis, the peaceful resistance to ice, so what one big thing that’s, that makes people think they can’t be compassionate again, is the, larger society, you know, the institutional frameworks and legislations and laws and government practices. Robertson: But even then, as we’re seeing, you know, in Minneapolis and everywhere, and Canada is leading in so many ways, I think I, I’m so grateful for the leadership of your, your prime minister, calling the world thatwe must not let go of the international rules rules based international practices that we’ve had for the last 80 years, my whole life. Robertson: You know, we’ve had the, the UN and the international rules and now some powers want to throw those out, but no, no, we are gonna say no. we’re [00:21:00] surrounded by forces of wealth and power as we know. And however we can each do what we can to care for those near hand, far away, the least the last, and the last for ourselves, moment by moment. Robertson: Breath, breath by breath. And sometimes we, the people can change history and the powerful can choose compassion. And, we’ve changed history many times. We’ve created democracy. We, the people who have created civil right. Universal education and healthcare of the UN and much more. Robertson: you touched a moment ago on the pillars of a compassionate civilization. You know, there are 17 UN sustainable development goals, as you know, but I decided 17 was a big number, so I thought, why don’t we just have six? That’s why my book, it has six arenas of transformation for ease of memory and work. Robertson: and they are environmental sustainability, gender equality, socioeconomic justice, participatory governance, cultural tolerance, peace and nonviolence. So modern [00:22:00] societies can be prevented from being compassionate also by Negative emotions as we were talking about, of ignorance, greed, hatred, and violence. Robertson: Greed thinking, I need more wealth. I’m a billionaire, but I need another billion. You know, I’m the richest billionaire in the world, but I wanna buy the US government hatred, violence. So these all for me, all back into the Buddhist wisdom of the belief that I’m a separate self. Robertson: Therefore, all that’s important is my ego. Hell no, that’s wrong. You know, my ego is not separate. When I die, my ego’s gone. You know, all that’s gonna be left when I die, or my words and my actions, my actions will continue forever. my words will continue forever. May I, ego? No. So the, if I believe my ego is all there is, and I can be greedy and hateful and fearful and violent, but ego, unlimited pleasure and narcissism, fear of the other, ignorance of cause and effect, these don’t have to drive us. So [00:23:00] structures and policies based on negative emotions and the delusion of a separate self and harm for the earth. We don’t have to live that way. We don’t have to believe propaganda and misinformation and ignorance, and we can provide the education needed and the experience. Robertson: We don’t have to accept wealth hoarding. You know, why do we have billionaires? Why isn’t $999 million enough? Why doesn’t that go to care for everyone and to care for the earth? So again, we have to let go of wealth hoarding of power hoarding. Robertson: we don’t need all that wealth. We don’t need all that power. We can, we can care for each other. We can care for the earth. Gissele: There, there are so many amazing things that you said. I wanted to touch on two the first one is that I was having a conversation with an indigenous elder, and he said to me, you know, that greed is just a fear of lack, right? Gissele: And it really stopped me in my tracks because, when we see people hoarding stuff in their [00:24:00] house, we think, well, that’s abnormal. And yet we glorify the hoarding of wealth. But it isn’t any different than any sort of other mental health issue in terms of hoarding. And so that really got me to think about the role of fear. Gissele: And, if somebody’s trying to hoard money, it’s not getting to the root of the problem, issue. It’s never gonna be enough because they’re just throwing it into an empty hole. It’s a a billion Jillian, it’s never gonna be enough because it’s never truly addressing the problem. Gissele: But one of the things that you said as we were chatting is, that the wealthy, the elite, they can choose compassion, they can always choose it, which is an amazing insight. And yet I wonder, you know, in terms of people’s perspectives of compassion and power, do you think that the two go hand in hand or can they go hand in hand? Gissele: Because I think there might be some worries around, well, if I’m more compassionate, then I’m gonna be, taken advantage of, I’m gonna be, a mat. what is your [00:25:00] perspective? Robertson: Oh, I agree with everything you said and your question is so, so important. Thank you so much. Robertson: there are billionaires and then there are billionaires like Warren Buffet. Look, he’s given. Tens of billions of dollars away, hundreds of billions of dollars away, and other billionaires have done that. And then there are the billionaires, who think 350 billion isn’t enough. Robertson: You know, I need more. Well, that’s crazy. That is sick. That is sad that, that is a disease. And we have to help those people. I feel compassion for billionaires who think they need another 10 billion or another a hundred billion, or they need five more a hundred million dollars yachts, or they need another 15 $200 million houses around the world and that that is very sad. Robertson: And that they’re really suffering. They’re confused. Yeah. They forget what it means to be human. They’ve forgotten what it needs to be. An earthling that we’re just here for a moment. Gissele: Agree. Robertson: We’re just here for a moment, for a [00:26:00] breath, and we’re gone. Breathe in, we’re here, breathe out, we’re gone. And so we can stop. Robertson: We can become aware of that fear, as you said. We can take good care of that fear. I love the way Thich Nhat Hahn says. He says, hello, fear, welcome back. I’m gonna take good care of you. Fear. I’m gonna watch you take care of you. You’re gonna Evolve. ’cause everything is impermanent. Everything changes. So fear will change. Robertson: Fear can change. Fear always changes It evolves into Another emotion, another feeling, So let it go. Let it go. In the truth of impermanence. ’cause everything is impermanent. Fear is impermanent. So we also can remember the truth of inter being that I am part of what I fear, I am part of. Robertson: This current federal administration. You know, I’m part of the wealthy elite, and it is part of me. I fear of the US administration right now, but it is part of [00:27:00] me and I’m part of it. I fear climate change, but it is part of me. I’m part of it. I fear artificial intelligence , unregulated. I fear old age, but boys, I’m 81 and a half, it’s here. Robertson: So I’m gonna take care of it. I’m gonna say, Hey, old man, I’m gonna take care of you. And they’re all me. There’s no separation. I love Thich Nhat Hahn’s word. We enter are, we enter are now, how can I stop, become aware of fear, breathe in and out, and know the truth of inter being and impermanence and accept it. Robertson: Care for it. get out to vote, care for the self, write , speak, do what I can to care for what I can. My family, my neighbors, my city, my county, my country, my world. And everything changes. Everything passes away. Everything comes in and out of [00:28:00] being, what happened to the Roman Empire? Gissele: Mm, Robertson: what’s happening to the American Empire. Everything comes in and goes out like a breath, breathing in and breathing out. And then everything transforms into what is next? What is next? what is China going to bring? Ah, there is so much that we don’t know, Robertson: I love Thich Nhat Hahn’s teaching that. when we become aware of a negative emotion, we should Stop, breathe, smile. And then say, oh, welcome. Fear. Welcome back. Okay, I’m gonna take care of you. Okay, we’re in this together. Robertson: And then you just, you keep breathing in awareness and gratitude and things change. Your grandkid calls you, your baby calls you, your dog, your cat. You see the clouds, you see the earth, the sun. You see a star. You realize you’re an [00:29:00] animal. You know the word animal means breath. Robertson: We are animals. ’cause we breathe. We’re all breathing. So I love that. You know it. I love to say I am an animal. ’cause I, you know, we, human beings are often not, we’re not animals. We’re superior To animals, you know? Right. we are animals, that’s why we love our dogs and cats and we can love our, the purposes and the elephants and the tigers and the mountain lions and, and the cockroaches and the chickpeas and the cardinals we are all animals. Robertson: We’re all breathing. So I love that. Gissele: Yeah. Yeah. Oh, that was so beautiful. I felt that also, I really appreciated the practice too. In this time when we, like so many us are, are feeling so much fear and so much uncertainty and not knowing how things are gonna pan out, to just take a moment to breathe and reconnect to our true selves, I think is so, so fundamental. Gissele: And I hope that listeners are also doing it with us. you know, as I have [00:30:00] conversations with people around the world we talk a lot about, the way that the systems are set up, the institutions. Gissele: And it took a lot of hard work for me to realize that we are the institutions, just like you said, so the institutions are made up of people. And I was so glad to see that in your book, that you clearly say, you know, like it’s about people. It’s about us. It’s like we make up these institutions, you know? Gissele: And when I’ve looked at myself, I’ve asked myself, who do I wanna be? What do I really, truly wanna embody? And my greatest wish for this lifetime is to embody the highest level of love and to truly get to the point where I love people like brothers and sisters, that I care for them and that we care for one another. Gissele: And yet, there are times when I wanna act from that place, but the fear comes up, the not wanting or not trusting or believing when the fear comes up, how can compassion really help us change ourselves so that we can create a [00:31:00] different world? Robertson: What you said is so beautiful, and your question is so powerful. Thank you. Yes. And I’m gonna get personal here. we can do what we can, we can take care of ourselves, we can take care of others as we can, but we shouldn’t beat ourselves up when we can’t. You know? Robertson: So I, here I’m 80, I’m over 81, and I have issues with balance and walking, and I have some memory issues and some low energy issues. So I have to be kind to myself. I, so I’ve just decided that writing is my main way of caring for the world. That’s why I publish one or two essays a week on Substack, on Compassionate Conversations for 55 countries in 38 states. Robertson: And so I said, you know, I used to travel around the world all the time. Not anymore. I don’t even want like to travel around the county. Robertson: Anyway, I’m an elder , so I have to say , okay, elder, be kind to [00:32:00] yourself, but also do everything you can, write everything you can speak with Gazelle if you can. Robertson: I also have to decide who I’m gonna care for. I’ve decided I’m gonna care for my wife who just turned 70 and my two kids and my two grandkids, my daughter-in-law, my cousins and nieces and nephews, my neighbors here and North Carolina. Robertson: The vulnerable, you know, I give to nonprofits who help the hungry and the homeless to friends and to people around the world through my writings and teachings And so the other day I drove to get some some shrimp tacos for my wife and me for dinner. Robertson: And a lady came up and she had disheveled hair. And she just stood by my car and I put the window down a little and she said. can you drive me to Black Mountain? that’s not where we were. I was in another town. ‘ cause I’m out of my medicine. Robertson: She just, out of the blue said, stood there and said that. And I thought, [00:33:00] oh, oh, hmm. Oh, so, oh yes. So I, I wanted to say, but who are you? How are you? Do you live here? Do do you have any friends or family? Do you, you, can I give you some money? Do you have, but I was kind of, I was kind of struck dumb, you know? Robertson: I thought, oh, oh, what should I do? And so I said, oh, I’m so sorry I don’t live in Black Mountain. And she said, oh. And she just turned and walked away and she asked two other cars and they said no. And then she walked away. And then she walked away. I thought, oh, Rob, Rob, is she okay? Does she have a family? Robertson: Did she have a house? What if she doesn’t get her medicine? How can she walk to that town? Could you have driven her and delayed taking dinner home to your wife? And then I said, but I don’t know. And then I thought, oh, but she’s gone. And I then I said, okay, Rob. Okay, Rob, [00:34:00] you’ve lived 81 years. You’ve cared for people in the UN in 170 countries. Speaker 3: Yeah. Robertson: And you’ve been in 55 countries, you’re still writing every week, you’re taking care of your neighbors and family and friends. Don’t beat yourself up. Old guy. Don’t beat yourself up. But next time, you know what Rob, I’m gonna say, Hey, my dear one, are you okay? I don’t have any money, but I can I buy you? Robertson: We are here at the taco shop, Can I buy you dinner? I would, I’m gonna say that next time, Rob. I’m gonna say that. and then I also gazelle,I’m gonna support democratic socialist institutions. You know, some people are afraid of that word, democratic socialist. Robertson: But you know, the happiest countries in the world are democratic socialist countries. Finland is the world’s happiest country. Denmark, Sweden, Norway, the Netherlands, Iceland, those are in the top 10 [00:35:00] when they’ve, when there have been analysis of, if you, if you Google happiest countries in the world, Robertson: those Nordic countries come up every year. Why? They are democratic socialist countries. You pay high taxes and everybody gets free college. You know, free education, free college, free health everybody gets taken care of in a democratic socialist country in the Nordic countries and New York City. Robertson: I’m so proud that our new mayor in New York City Zoran Mai is a democratic socialist. He is there to help everybody, but particularly those who are hurting the poor, the hungry , the sick, or the people of color, women, the elderly, the children. I’m so proud of him and I write about him on my substack and I write him Robertson: I he’s one of my heroes just like Bernie Sanders is one of my heroes. And Alexandria Ocasio Cortes, a OC is one of my, my heroes, CA [00:36:00] Ooc. So, and you know, I used to never tell anybody I was a Democratic socialist ’cause I was afraid. I thought, oh, they’ll think I’m a socialist. Hell no. I am now proud to say I’m a democratic socialist. Robertson: I’m a Democrat. I vote the Democratic ticket, but I’m always looking for progressives, progressive Democrats, you know, democratic socialist Democrats. because, you know, our country can be more like Finland, Denmark, Sweden, Norway, the Netherlands, Iceland New York City. New York City is showing us the way America can be like a New York City. Robertson: I’m so proud of New York City and I used to live in New York City so as an old person. I can only do what I can do. and I’m not saying, oh, I poor me. I can’t do anything. No, no. I’m not saying that. I’m saying I can do a hell of a lot as this 81-year-old, it’s amazing what I can do, but that is why I write and speak and care for my family, neighbors, friends, the poor. Robertson: [00:37:00] Donate to nonprofits for the homeless and the hungry vote. Get out the vote. So yes, that’s my story. Gazelle. Gissele: I totally relate. I mean, I’ve been in circumstances like that as well, where you wanna help. But the fear is like, what if a person kills you? What if they don’t really have medication? Gissele: What if you get hurt or they try to rob you or they have mental health problems? Mine goes to protection and it is very human of us to go there first. And so, so then we get stuck in that ping pong in that moment and then the moment passes and you’re like, you know, was it true? Could I have driven that person? Gissele: And that would’ve been something I wanted to do for sure. But in that moment, you are stuck in that, yo-yo, when the survival comes in. And so helping ourselves shift out of that survival mode, understanding and learning to have faith and trust. And for me that’s been a work in progress. Gissele: It really has been a work in [00:38:00] progress. The other thing I wanted to mention, which I think is so important that we need to touch on. It’s the whole concept of socialism. So I was born in South America before I came to Canada and so I remember lots of my family members talk about this, there’s many South American countries that got sold communism, as socialism we’re talking about approaches that instead of it being like a democratic socialism that you’re talking about, which is the government, make sure that people are taking care of and that the people are probably taxed and provided for what would happen in those countries was that. Gissele: Everything got taken away. People were rationed certain things, and, it was horrible. it was not good, but it was not socialism. And there was many governments that took the majority of the money, then spent it on themselves, left the country, took it themselves, and so especially the Latin American community is very much afraid of socialism because they think back to that, the [00:39:00] rationing of electricity, the rationing of food, the rationing of all of that stuff, it wasn’t provided openly. Gissele: It was, everybody gets less. And so you have these people with this history that then have come to the US and think they don’t want socialism. They think democracy means that people aren’t gonna take stuff away from them, but that’s not what it means either. ’cause I don’t even know if like in North America we have a true democracy. Robertson: so thinking about reframing of how we think or experience democratic socialism, that it doesn’t mean less for everybody and in everything controlled by the government. It means being provided for abundantly and, also having the citizens be taxed more, which means we are willing to share our money so that we can all live well, Beautiful. Beautiful. Oh, thank you. Hooray. Wonderful. What country are you? May I ask where you coming? Gissele: Yeah, of Robertson: course. Gissele: Peru, I Gissele: [00:40:00] Yeah. Robertson: Wonderful. I’ve been to Peru a few times. A wonderful, beautiful country. And I, I lived in Venezuela for five years. ‘ cause I love, I have many friends in Venezuela. Robertson: But anyway I agree with everything you just said. That’s why I said what I said that I now can, I can confess that I am a democratic socialist. And that’s not socialism. It’s a social democracy is what it’s called. Yeah. That’s what they call it in Finland and Denmark and so on. Robertson: They call it social democracy. It’s democracy. But it, as you say, it’s cares for everyone and for the earth. We have to always add and the earth, ’cause you know, all the other species and, and the other life forms and the ecosystems, the water, the soil, the air, the minerals the plants, the animals. Robertson: and we have the money, as you said. I mean, if I had $350 billion, think of what taxes I could pay if the tax rate was, you know, 30%. [00:41:00] And rather than nothing, some of these, some of these folks pay, Gissele: well, I think we have glorified that we all wanted that, right? Like we got sold this good that oh, we should all want to be as wealthy as possible, right? And so we normalize the hoarding of money. Not the hoarding of other stuff, right? Gissele: And so we have allowed that, which gets me to my, next point, you talk about the environmental impact as part of a compassionate society, which absolutely is necessary. Gissele: And as human beings, we can be so lazy. We want convenience. We want to, have our package the next day. We don’t wanna wait. are we willing to pay higher wages? Are we willing to wait? Longer for our packages, like, are we willing to, invest in our wardrobe instead of buying fast fashion? Gissele: We don’t do these things and these have environmental impacts, and it also have human impacts, and at the end, they have impact on us. What can we do to ensure that, that we address that [00:42:00] complacency so that we are creating a fair, affordable , and compassionate world. Robertson: So important. Thank you. Robertson: It’s, it’s a life and death question. So yes, we should always ask about ecological and social impacts and take actions accordingly. That’s why I recycle every day. You know, some people say, oh, recycling is stupid. What do they really do with this, with it? You know, are they, are they really careful when you, they pick it up? Robertson: but I recycle religiously every day That’s why I support climate and democracy through third act. There’s a group that Bill McKibbon has started here in the US called Third Act. It’s a group of elder activists, activists over 60 who are working on climate and democracy issues. Robertson: So I’m doing that. That’s why I vote and get it out to vote. And as I said, I vote for Democrats and Democratic socialists. That’s why I write and speak and vote for ecological regeneration for social justice, for peace, for [00:43:00] democratic governance. It’s so critical that we keep questioning our actions like. Robertson: Okay, why am I recycling? Is it really worth the time? You know, deciding about every item, where it goes, and then putting out it out carefully and rinsing it first. And is that really going to help the world? ’cause you also know we need systemic changes, because you can always say, oh, but what the individual does doesn’t matter. Robertson: We need laws, we need institutions of ecological regeneration, and we need laws on caring for the climate and stopping climate change. So you can talk yourself out of individual responsibility when you realize that we need laws and institutions that protect the environment. Robertson: But it’s both. It’s both. what each person does, because there are millions of us individuals. So if there are millions of us act responsibly, that has, is a huge impact. And then if we [00:44:00] also have responsible laws and institutions that care for the environment as well as all people, then that’s a double win. Robertson: So I agree with you. We have to keep asking that question over and over and making those decisions and they’re hard decisions. We have to decide. Gissele: Yeah, I’ve had to look at myself like one of the commitments I’ve made to myself is not buying fast fashion. And so, investing in pieces, even though sometimes I feel lack oh my God, spending that much money on this, you know? Gissele: Yeah. It all comes back to me. if I am not willing to pay a fair wage, that means that the next person doesn’t get a fair wage, which means they don’t wanna pay a fair wage and so on and so forth. And then it comes back to me, you know, my husband has a business and then, you get people that don’t also wanna pay a fair wage. Gissele: It’s all interconnected. And so we have to be willing, but that also goes to us addressing our fear, our fear of lack, that we’re not gonna have enough. All of those things. And the biggest fundamental [00:45:00] fear, and you mentioned death to me, is the ultimate Gissele: fear That we must overcome I think once we do, like, I think once we understand that we are not, this human vessel. Gissele: that we’re not just this bag of bones and live in so much constrained fear that perhaps we could. really open up ourselves to be willing to be more compassionate . What do you think? Robertson: Absolutely. I’m with you all the way. Yes. We fear death because we’re caught in that illusion of a separate permanent self. Robertson: You know, it’s all about me. Oh, this universe is all about me. The universe was created 13.8 billion years for me. Robertson: Yeah. But it’s all about me and particularly my ego, honoring my ego. Building up my ego, praising my ego being, you know, that’s why I wanna be rich and famous. Robertson: Fortunately, I never wanted to be rich or famous, but that’s another story. We’ll talk about that some other time. But everything and [00:46:00] everyone is impermanent. When I realized that truth and it, it came to me through engaged Buddhism, but you could, you could get that truth in many, many ways. Robertson: That everything and everyone is impermanent. we’re part of the ocean. But the waves don’t last forever, do they? But the ocean lasts forever. Robertson: So My atoms, are part of the 13.8 billion year old universe. my cells are part of the living earth. Yes, they remain When I die, you know, go back into the earth. back into the soil and the water and the air but My ego doesn’t remain. What, what remains, as I said before, are my actions. Robertson: Everything I did is still cause and effect. Cause and effect. Rippling out. Rippling out. Okay. Rob, what did you do? What did you say? did you help that, did you touch that? Did you say that? so my actions and words continue rippling forever. So Ty calls that, or in the Plum Village tradition of engaged Buddhism, it’s called my continuation. Robertson: Your actions and your words [00:47:00] are your continuation that last forever as your actions and words will continue through cause and effect touching reality forever. So when my ego does not remain so I can smile and let it go. I often think about my continuation. You know, I say, well, that’s why, maybe why I’m writing so much and speaking so much. Robertson: And caring for so many people every day, you know, caring to care for my wife and my children and grandchildren and friends and neighbors, and the v vulnerable and the hungry, and the homeless, and the, and my country, and my city, and my county, and my, and why do I write substack twice a week? Robertson: And containing reflections on ecological, societal, and individual challenges and practices. And so every, week I’m writing about practices of mindfulness and compassion. So I’m trying to be the teacher. I’m trying to send out words of mindfulness and compassion so that they will continue reverberating when I’m dust, Robertson: So [00:48:00] I’m reaching out. In my substack to just those 55 people in 55 countries, in 38 states, touching hearts and minds and even more on social media. every month I have like 86,000 views of my social media. Why do I do it? It’s not just about ego, you know? Robertson: Oh, Rob, be famous. No, Rob is not famous. I’m a nobody. I gotta keep giving and giving and giving, you know, another word, another action, so I can, care for people around me through personal care, donations, voting, volunteering workshops, I’m helping start a workshop in our neighborhood on environmental resilience through recycling, through group facilitation. Robertson: I’m trained in, facilitation. I’ve been trained my whole life to ask questions of groups so they can create their own plans and strategies and actions. that’s some of my answer. Robertson: I hope that makes some sense. Gissele: Thank you very much. I appreciated your answer and it made me really think you are one of our compassionate leaders, right? [00:49:00] You’re, you’re kind of carving the way and helping us reflect, ’cause I’ve seen some of your substack, I’ve seen like your postings. Gissele: That’s actually how I kind of reached out to you. ’cause I was so moved by the material that you were sharing, the willingness to be honest about what it takes to be compassionate and how hard it can be sometimes to look at ourselves honestly, because we can’t change unless we’re willing to look at ourselves. Gissele: All aspects of ourselves, like you said, we are the billionaires, we are the oligarchy, we are all of these people. The racism that voted that in the, the racism that continues to show the fear, all of that is us. And so from your perspective, what do compassionate leaders do differently? Robertson: Yes. Well, it great question. Robertson: what do compassionate leaders do differently? Well, he or she or they. Robertson: are empathic. I think it starts with empathy. What are like, what are you feeling? What are you thinking? Robertson: What are you, what’s happening in your life? So an empathic [00:50:00] leader listens to other people. They see where other people are hurting. They care. They ask questions and facilitate group discussions, enable group projects. They let go of self-importance, you know, that it’s not all about me. Robertson: They let go of narcissism. They let go of, the ego project. They help others be their greatness. They care for their body mind so that they can care for others. and they donate and vote and recycle and more and more and more and more. did you know in Denmark. In elementary school every week, children are taught empathy. Robertson: You know, they have courses on empathy, Robertson: when I was growing up, I,didn’t have courses in school on empathy in church school, you know, in my Sunday school at, in my church. I was taught to love my neighbor and to love everyone, and that God was love. But in school, in my elementary [00:51:00] school and junior high and high school, we didn’t talk about things like empathy and compassion. Gissele: Yeah. Thank you for sharing that. I did know about Denmark ’cause my daughter and I are co-writing a book on that particular topic. The need to continue to teach love and compassion in, Gissele: being a global citizen. Right? And, and I’m doing it with her perspective because she just graduated high school, so she has like the fresher perspective, whereas mine’s from like many moons ago. Gissele: We need to continuously educate ourselves about regulating our own emotions, having difficult conversations, hearing about the other, other, as ourselves. Because that’s, from my perspective, the only way that we’re gonna survive. a friend of mine said it the best that we were having a conversation and she does compassion in the prison system and she says, I can’t be well unless you are well. Gissele: My wellness depends on your wellness. And that just hit me in my heart, like, ugh. Not that I live it every day, Robertson, Gissele: every day I have to choose and some [00:52:00] days I fail, and other days I do good in terms of like be more loving and compassionate and truly helping the world. But it’s a choice. It’s a continual choice. So this goes to my biggest challenge that maybe you can help me with, which is, so I was having this conversation with my students. We were talking about how. In order to create a world that is loving and passionate for all, it has to include the all, even those who are most hurtful, and that is really difficult . Gissele: I’m just curious as to your thoughts on what starting point might be or what can help us look at those who do hurtful things and just horrible things and be able to say, I see God within you. I see your humanity. Even though it might be hard. Robertson: Yes, It is hard. several years ago when I would hear [00:53:00] leaders of my country speaking on the media, I would get so repulsed that I would turn it off but I began practicing. Robertson: I practiced a lot since those days and I realized, you know. People who hurt, other people are hurting themselves. they’re actually hurting. they’re suffering. People who hurt others have their own suffering of, they’re confused. they’ve forgotten what it means to be human. Robertson: They’re, full of, greed, of their own fears, all about me. Maybe they’re filled with hatred they become violent. they’re suffering. I still find it very difficult to read or listen to certain people. Robertson: But what I do is I stop and I breathe and I smile and I say, okay. Robertson: I care. I’m concerned about you. I don’t know what I can do, but I am gonna do everything I can to care for the people, being hurt, you know, like my fellow activists in [00:54:00] Minneapolis are doing, or elsewhere, we could mention many places around the world where people are risking their own lives. Robertson: You know, in Minneapolis, two activists were killed, Ms. Good Renee Good, and Alex Pretty were killed because they went beyond their fear, you know? they got out there in the street because the migrants were being hurt and they got killed. Robertson: So, you know, At some point you have to come to terms with your own death, I don’t know if I have a, a minute to go or 20 years, I still have to let go. And so how do I care for my wife, my family, my friends, my neighbors my country, the vulnerable, the homeless, the hungry, and, as you said, for the wealthy and powerful who are hurting others, you know, starting wars attacking migrants, killing activists. Robertson: It’s hard. You know? So I have to say, I love the story of [00:55:00] when during the Vietnamese war Thich Nhat Hahn and his monks. They did not take sides. They did not say we’re on the side of the Vietnamese or the us. They did not take a side in the war. This is hard for me ’cause I, I usually take sides. Robertson: The practice was, okay, we’re not going to support we’re Vietnamese or the us. Were going to care for everyone. So they just went out caring for people who were getting hurt and during the war, people who were hungry, people who needed food, people who were bleeding, Robertson: So they decided their role was to care for those who were hurt not to attack. To say, I’m for the blue and I’m against the red. They said, I’m just gonna, care . Like, the activists in Minnesota, They’re, they’re not attacking ice, they’re singing to ice. Robertson: And so yes, we have to acknowledge our own anger. [00:56:00] I’m angry with these politicians. sometimes I want, to hate them, but I have to say, I do not hate you, my friend. You are confused. You’re so confused. You’re hurting others. So you’re so hurtful. Robertson: You don’t realize how you’re hurting others. But, I’ve got to try to stop you from hurting others. I’ve got to try to help those who are hurt and maybe I’m gonna get hurt, you know, because in the civil rights movement, if you’re out there doing on a peace march, you might get beaten up. Robertson: as I said, I’ve lived in villages, poor villages, and. Urban slums in several countries. And some people could say, well, that’s stupid. You could get hurt. You know, you could, you could as a white person living in a African American slum or in a Korean village or in a Venezuelan village, Robertson: So, you know, I say, was I stupid? Was I risking and I was with my wife and children? Was I risking the lives of my wife and children by living in slums and, and villages? Yes. Was I stupid? I mean, [00:57:00] no, I wasn’t stupid, but I was risking our lives. But I somehow, I was, called I wanted to do it. I said, okay. Robertson: but my point is it’s risky, you know? And you have to keep working with yourself. That’s why I love the word practice. Robertson: You know, in Buddhism we keep practicing, and I love your, the teaching of that you have on your website of Pema Chodron, you know, on self-love. You know, you have to keep practicing. How do I love myself? Say, okay, I’m afraid and I’m just this little white person, but or I’m this little old white person, but I’m gonna do everything I can and be everything I can. Robertson: I really appreciated the story of Han not choosing sides. I mean, you’re right. If we are going to see each other’s brothers and sisters and is is one global family, we can’t pick a side over the other, even though we so want to. Gissele: And, and I’m with you. when I think that there’s a [00:58:00] unfairness, when there’s people that are vulnerable or suffering, I’m more likely to pick to the side that is like, oh, that person is suffering. They’re the victim. But what you said is spot on. People that truly lovewho have love in their heart, like when you were raised with love. Gissele: You had love to give others because your cup was full. So it overflowed to want to help others, to want to love others. People that are hurting, that don’t have love in their hearts are those that hurt other people. Robertson: Mm-hmm. Gissele: They must because they must be so separated from their own humanity. Robertson: Yes, yes, yes. Gissele: And yet things are changing. You mentioned Minnesota, and I wanted to mention that I love that they’re doing the singing chants, and they’re not making them wrong. they’re singing chants like you can change your mind. You don’t have to be wrong. You don’t have to experience shame and guilt for the choice you’ve made. You can always change your mind. And in your book, you talk a lot about movements. Do you wanna [00:59:00] share a little bit about the power of movements and helping us create a compassionate civilization? Robertson: Oh, yes. Thank you. I’m, I’m a big movement fan. it started in college with the Civil Rights Movement. I realized, wow, you know, if a lot of people get together and do something together, it can make a difference. Like the Civil Rights movement. Gissele: Yeah. Robertson: And the women’s movement and peace movement. Robertson: And like in Vietnam, the peace movement, we could really make a difference if we get out in March. I think that being an individual or part of an organization that is part of a movement can be a powerful force. And so I focus in my life and that, that book on the six movements that I’ve mentioned, and those movements can work together. Robertson: And when they work together, they become a movement of movements. They become mom. Hmm. I like that because I I’m a feminist and I think that we need so [01:00:00] desperately we need more feminine energy inhumanity and in civilization. Robertson: So I’m a unapologetic feminist. And so that’s why I like that the movement of movements, the acronym is Mom, you know, and so it’s the Moms of the World will lead us like you. And so they’re the movements of ecological regeneration, socioeconomic justice, I’m repeating gender equality, participatory governance, cultural tolerance, peace and non-violence. Robertson: And you know, we also have the Gay Rights Movement, the democracy movement. there’s so many movements that it made a huge difference. So. I began saying that I, after writing the book, I said, okay,now my work is the work of the Compassionate Civilization Collaborative. Robertson: And I decided I wouldn’t make an organization, I it, wouldn’t have a website, I wouldn’t register it. I wouldn’t raise money for it. It would just be anybody and everybody [01:01:00] who was part of the movement of movements who was working to create a compassionate civilization. Robertson: So that’s what I did. And that’s where I am. I’m this old guy in my home. I don’t get out a lot. I don’t drive a lot. I just drive to nearby town. I have a car, but I don’t use it a lot. I don’t like to walk up and down hills. Robertson: IAnd sometimes I can’t remember things and I say, Hey, but look, you have so many friends all over the world and you can keep encouraging through your writing. So that’s why I keep writing, you know, it is for the movement of movements. Robertson: I guess that’s why I write. here’s something I want to share, something I thought or felt or something that I wrote about. And maybe it will touch you. Maybe it’ll encourage you. Maybe we’ll help you in your life. Robertson: I live in a homeowners association neighborhood. It’s a neighborhood that has a homeowners association. We’re 34 families and we have straight families, gay families. we have white families and non-white families. [01:02:00] We have Democrats, Republicans and Socialists. Robertson: We have Christians and Buddhists and Hindus. And so what I do, I say, Hey, we’re all neighbors. We all helped each other during the pandemic. We all helped each other after the hurricane. It doesn’t matter what our politics are or our religion or our sexuality, we’re all human beings. Robertson: We’re all gonna die. we all want love. We all want happiness. And We can be good neighbors. We don’t have to have ideology, you know, we don’t have to quote the Bible, we don’t have to quote Buddha. We can just be good neighbors. So we’re gonna have a workshop this spring And so we’re all going to get together down the street in this big room, in the fire station, and we’re gonna have a two hour workshop. And will it help? I don’t know. Will it make us better neighbors? I don’t know. Why am I doing it? I’m driven to do it. I’ve done workshops all over the world and I wanna do a workshop in my neighborhood. Robertson: I’ve done workshops with the un, I’ve done [01:03:00] workshops with governments, with cities So I love to facilitate. I love getting people together to solve problems together to listen to each other, respect each other, to honor each other. Gissele: so I’m just gonna ask you a couple more questions. But I’m just gonna make a comment right now about what you said because I think it’s so important. Gissele: Number one is I love that your neighborhood is a microcosm of what our world could be like . The fact that people got together to help and make sure that people were taken care of. If we could amplify that, that could be our world. I think that’s such a beautiful thing. Gissele: And the other thing that I think is really fundamental is that even through your life, you are showing us that some people are going to go pickett. And that’s okay. Some people are gonna write blogs to help us, and that’s okay. Some people are gonna do podcasts, and that’s okay. There are things that people can do that don’t have to look exactly the same. Gissele: Some people are going to have more courage, and they’re going to put their bodies in front and potentially get hurt. Other people, maybe they can’t do [01:04:00] that. So there are many different ways to help. The other thing that you said that was really, really key is the importance of moms . And that was one of the things that really touched me about your book, the acronym. Gissele: I was like, oh my God, I so resonate with this. Because I do feel that we need more feminine energy. We really kind of really squash the feminine energy. But the truth of the matter is we need more because fundamentally, nurturance is a mother energy is a feminine energy. Gissele: Compassion’s a feminine energy. Yes, yes, yes, Robertson: yes, yes, Gissele: so if I can share my story. Last night I was at hockey game. My son was playing hockey. Robertson: Mm-hmm. Gissele: And our team they don’t like to fight. Gissele: We play our game and we have fun and we’re good. And so the previous teams that were there, it was under Youth 15, most of the game was the kids fighting. And taking penalties. And so the game ends, the people come off the ice and two men that are starting to get like into a fight [01:05:00] now, woman got in front of them. Gissele: Wow. and said, we all signed a form that said, this is just a game. Remember who this is for? even though she was elevated, she totally stopped that fight between two men that we were not small. And So it was, it was really interesting. Robertson: Wonderful. Gissele: it was a woman who actually stopped a fight Gissele: It’s the feminine power. And that doesn’t mean, and I wanna make this clear, that doesn’t mean that men have to be discarded or have to be treated the same way that women are treated. ’cause I think that’s a big fear. That’s a big fear that some white males have. It’s no, you don’t have to be less than, Robertson: right. Robertson: We need Gissele: to uplift the feminine energy. So there’s a balance. ’cause right now we’re not balanced. Robertson: Exactly. Exactly. Oh, boy. Am I with you there? there’s a whole section in my book, as you noticed on gender equality I’m gonna read a tribute to Mothers I. Robertson: Tribute to Mothers Giving Birth to New Life, nurturing, [01:06:00] sustaining, guiding, releasing, launching, affirming Love. Be getting Love a flow onwards. Mother Earth, mother Tree, mother Tiger, mother Eve. My grandmother’s Sally and Arie, my mother, Mary Elizabeth, my children’s mother, Mary, my grandchildren’s mother, Jennifer, my grandchildren’s grandmothe

Microcosmos Records presents Ride The Cosmic Wave, the new album by Síntese. Síntese is the solo project of Paulo Oliveira from Guimarães, Portugal. Previously known as part of the psytrance act Spectra, Paulo stepped away from the project in 2014 and spent several years immersed in shamanic practices — a period that quietly reshaped his creative direction. Síntese emerged in 2018, rooted in openness, improvisation, and a desire to move beyond genre boundaries. Ride The Cosmic Wave is his tenth album. The music is created in the moment — hypnotic, gently experimental, guided more by feeling than by formula. Soft cosmic textures and slowly evolving harmonies settle into a space between deep listening and gentle motion, unhurried and borderless. Each track carries its own quiet intention, leaving space for the listener to travel freely. Put on Ride The Cosmic Wave and drift through the sound world of Síntese.

Ever wonder why some COOs scale businesses to legendary heights while others get swallowed by chaos and politics? If you're craving clarity, confidence, and uncommon edge in your second-in-command role, this Fan Favorite episode is your wake-up call. Cameron Herold sits down with Matt MacInnis, COO of Rippling and co-founder of Inkling, for a raw, actionable conversation about the real challenges behind hyper-growth, hiring, trust, and culture. They dig into what makes the COO role so “special,” how to build a game-changing flywheel, and why patience, precision, and authenticity are the ultimate power moves.The pain of “going it alone” is real. Tune in to learn how to avoid disaster, dodge politics, and harness proven tactics you won't find in any business book. Don't wait until burnout bites. Listen now for fiercely exclusive COO insights, bold truths, and systems that will let you scale smarter, not harder.Timestamped Highlights[00:02:22] – The hidden pain in HR, IT, and how Rippling breaks the “original sin” of bad data[00:05:55] – Why Matt almost walked away—then got schooled by Parker's contrarian “rocket ship” logic[00:08:30] – The untold power of preexisting trust between CEO and COO—and what happens if you hire without it[00:12:49] – Topgrading secrets: Why most executive hiring fails and how to get it right (even when everyone says they're an “A player”)[00:15:44] – Copilot dynamics: How Matt and Parker run the company with surprisingly little contact (and why it works)[00:19:18] – Should you debate the CEO in front of the team? The cathartic, risky art of public disagreement[00:23:13] – Inside Rippling's flywheel advantage—what Salesforce, Facebook, and Brex did differently and why you can too[00:31:04] – Killing bureaucracy and politics: The simple rule for hiring and process that most leaders ignore[00:39:29] – The brutal, proven formula for layoffs: What Sequoia teaches (and how to survive the “survivor's guilt”)About the GuestMatt MacInnis is the Chief Operating Officer of Rippling, a revolutionary all-in-one HR and IT platform transforming how businesses scale and manage people. Matt was also the co-founder and CEO of Inkling, a mobile learning platform that raised over $100M before its acquisition. With deep roots at Apple and a Harvard engineering degree, Matt blends big-company brilliance with entrepreneurial firepower. He's known for breaking boring business norms and igniting hyper-growth, all while refusing to tolerate politics, inefficiency, or shallow executive hiring.

The Shred is a weekly roundup of what's making headlines in the world of employment. The Shred is brought to you today by Jobcase.

#330 | Dave is joined by Ryan Narod, VP of Marketing at Rippling, to break down how Rippling has built one of the stand outbrands in B2B right now. Ryan walks through real examples of campaigns they've run over the last year, from scrappy iPhone videos and webinar promos to high-production customer stories and their 2026 Super Bowl commercial. They talk about how Rippling shifted from being great at growth marketing to building a brand people actually recognize, how they inject more personality and “human” into everything they ship, and how they measure brand marketing without losing pipeline accountability. To see Ryan's real campaign examples, head over to youtube.com/@heydavegerhardt.Timestamps(00:00) - - Why Rippling is going all-in on brand (02:51) - - Ryan's background and why he joined Rippling (04:14) - - What Rippling does and how they position the platform (08:14) - - What “brand marketing” means at Rippling (10:34) - - Building a story that makes HR the hero (19:47) - - Ryan shares Rippling marketing examples (ads, videos, webinars) (27:17) - - High-production customer storytelling (Berries) (32:39) - - The “HR Deserves Better” campaign (35:37) - - How Rippling measures brand and pipeline impact (43:14) - - The Super Bowl commercial and what it takes to pull it off (45:17) - - Final takeaways and wrap-up Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.  ***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used. In today's episode, we discuss: Why design leaders who stop designing stop leading The four pillars every design manager must master How to delegate when you're a perfectionist Why leaders need strong opinions How to scale good judgment What Rippling's operating system teaches about speed and commitments References: Airbnb: https://www.airbnb.com/ Amazon: https://www.amazon.com/ Apple: https://www.apple.com/ Asana: https://www.asana.com/ Brian Chesky: https://www.linkedin.com/in/brianchesky/ CrossFit: https://www.crossfit.com/ Figma: https://www.figma.com/ Honeywell: https://www.honeywell.com/ Liz Sanders: https://www.linkedin.com/in/sandersliz/ Nest: https://store.google.com/category/google_nest Notion: https://www.notion.so/ Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Rippling: https://www.rippling.com/ Stripe: https://www.stripe.com/ Where to find Ryan: LinkedIn: https://www.linkedin.com/in/ryanwlucas/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Intro 00:08 What design actually does at a software company 01:40 The roots of design: from industrial design to software 03:29 Useful, usable, desirable — and used 04:49 How design relates to engineering, product, and marketing 08:15 Measuring success as a design leader 12:40 The gap between director and VP-level design leadership 14:23 Why great design leaders jump up and down in altitude 19:26 The four pillars every design manager must master 21:34 Over-indexing on quality and the perfectionist trap 25:11 When lowering the quality bar actually cost the business 27:53 How to build judgment through pattern matching 31:25 How Ryan's design team differs from the rest 34:31 Why Figma is not the source of truth 36:32 How Ryan spends his week: recruiting, crits, and staff meetings 38:39 The "Do/Try/Consider" framework 42:12 The most important decisions of the past year 44:05 Should one-on-ones exist? 46:45 How to scale judgment 50:49 What to look for when hiring your first design leader 54:54 Advice for young designers who want to lead 58:24 Demanding yet supportive: A balanced management style 01:02:43 What Rippling's operating system teaches about execution

Keith Rabois joins the Newcomer Podcast for a wide-ranging conversation that moves between tech, venture capital, and politics.On the tech side, we start with Brex being acquired by Capital One and what that means for Ramp. Rabois argues that banks won't build the “finance organization of the 21st century,” and frames Ramp's ambition as building the CFO's “eyes, ears, and actions” across a company. We also discuss Rippling's strategy, investor responsibilities around integrity and ethics, and how he thinks about “barrels and ammunition” when companies try to do many things at once.From there we get into AI investing and Rabois's view that what matters is the end-customer value proposition and the durability of the advantage. He explains Rogo as an AI “copilot” for investment bankers and talks about workflow and data moats.The episode also turns heavily to politics and current events: Trump, tech's relationship with the administration, immigration (including H-1B and O-1 visas), free speech, and foreign policy debates (including China, Europe, and the Middle East). We also argue through a recent incident involving law enforcement and protest/obstruction, and close with Opendoor—where Rabois lays out his view of the company's turnaround, retail investors, and the company's weekly “accountability” metrics updates.

Plus Texas actor James Van Der Beek has died at the age of 48, hundreds of dogs have been rescued from a Dallas animal fighting operation, the city of Dallas' representation on the DART Board of Directors can soon change after a newly passed resolution, and more!

Keith Rabois joins the Newcomer Podcast for a wide-ranging conversation that moves between tech, venture capital, and politics.On the tech side, we start with Brex being acquired by Capital One and what that means for Ramp. Rabois argues that banks won't build the “finance organization of the 21st century,” and frames Ramp's ambition as building the CFO's “eyes, ears, and actions” across a company. We also discuss Rippling's strategy, investor responsibilities around integrity and ethics, and how he thinks about “barrels and ammunition” when companies try to do many things at once.From there we get into AI investing and Rabois's view that what matters is the end-customer value proposition and the durability of the advantage. He explains Rogo as an AI “copilot” for investment bankers and talks about workflow and data moats.The episode also turns heavily to politics and current events: Trump, tech's relationship with the administration, immigration (including H-1B and O-1 visas), free speech, and foreign policy debates (including China, Europe, and the Middle East). We also argue through a recent incident involving law enforcement and protest/obstruction, and close with Opendoor—where Rabois lays out his view of the company's turnaround, retail investors, and the company's weekly “accountability” metrics updates.

Maxima is building AI agents that automate enterprise accounting while maintaining the auditability and control standards finance teams require. In a recent episode of BUILDERS, we sat down with Yogi Goel, CEO and Co-Founder of Maxima, to explore his eight-year journey at Rubrik from Series C through IPO, and how those lessons shaped his approach to solving the 70-80% of finance time currently wasted on manual work. Topics Discussed: Why Rubrik's approach—entering stagnant markets with first-principles thinking—became Maxima's blueprint Securing $3K-$5K POC commitments from Figma mockups before writing code Why Scale AI and Rippling rejected a point solution and demanded 3-4 modules from day one The compound startup model: building multiple products simultaneously to meet buyer expectations How 17% of CFOs are adopting AI tools today (vs 51% in software development) Why finance teams view AI agents as "digital college freshmen" who need proof of work Hiring from YouTube Studios, Apple, and Robinhood instead of legacy finance software companies How NetSuite World conference booth sizes revealed the data integration infrastructure gap The $3K-$5K validation threshold that proved finance pain was urgent enough to pay pre-product GTM Lessons For B2B Founders: Demand generation unlocks engineering potential: Yogi learned from his Rubrik mentors: "focus on demand and if you have great engineers then they will solve the problems." Maxima built products in 2-3 months they didn't initially know were technically feasible—because customer demand pulled the engineering team forward. For founders with strong technical teams, customer demand should drive the roadmap, not engineering's comfort zone. Trust your engineers to solve hard problems when customers are waiting. $3K-$5K is the pre-product validation threshold: Before writing any code, Yogi secured POC commitments at this price point based solely on Figma mockups. This isn't about revenue—it's about proving urgency. Verbal interest means nothing. Small pilot commitments mean "we'll try it someday." But $3K-$5K pre-product means "this problem is urgent enough to pay before seeing a working solution." Use this threshold to separate real pain from polite interest. Sophisticated buyers will reject your narrow MVP: Scale AI and Rippling told Maxima explicitly: "If you will only build this one thing, we will not buy. You have to commit to building three, four modules." Conventional wisdom says start narrow, but enterprise buyers with complex workflows won't adopt point solutions that create new integration headaches. When sophisticated buyers articulate their real buying criteria, ignore the startup playbook. Yogi built a "compound startup" with 4-5 modules from day one because that's what the market demanded. Target acute pain over easy access: Early-stage companies (10-30 people) were easier to reach but finance wasn't urgent enough. At that scale, it's "build product, ship product"—finance operations aren't broken enough to warrant urgent attention. Companies at 500-1,000+ employees have finance teams drowning in manual work that prevents strategic contribution. Target where pain justifies urgent action and budget exists, not where calendar access is easiest. Hire intensity and first-principles thinking over domain knowledge: Maxima deliberately hired zero engineers from legacy finance software companies. Their frontend engineer came from YouTube Studios. Others came from Apple, Robinhood, Netflix—none with financial product experience. Yogi's three hiring criteria: "incredible intensity, huge confidence in themselves, and fast thinking mode." Domain expertise creates pattern-matching to old solutions. First-principles thinking creates breakthrough products. One team member didn't finish high school but is "one of the best out there." Make AI explainable or finance teams won't adopt: Finance teams adopted faster than expected because Maxima showed every calculation step. "If they can prove by looking at the Math, you know, 18 plus 88 plus 36 is X. And I can see the step of the work, they are willing to give it to them." This isn't about fancy UX—it's about auditor-grade proof of work. Finance professionals won't trust black box outputs. Build transparency into the product architecture, not as an afterthought. This explainability became Maxima's competitive moat. Conference booth sizes reveal infrastructure gaps: At NetSuite World, the largest booths weren't ERP vendors or payment processors—they were data integration companies. This single observation validated that enterprises are desperately solving data fragmentation problems. Companies manually download from Stripe, Snowflake, Salesforce weekly to build Excel pivots. Maxima invested in upstream integrations as core infrastructure from day one. Use industry conferences to validate where companies are spending money on workarounds—that's where infrastructure gaps exist. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Matt MacInnis spent 6 years as COO at Rippling and now leads as CPO. He joined Rippling in 2019, when there were only 70 people, and has led the company across multiple stages.Before that, Matt was a founder for 9 years, building Inkling after 7 years at Apple. These three chapters of his career shape this conversation. We focus on how to build and operate teams as a company scales. Matt explains how he thinks about speed versus real progress, and which parts of building a company should move fast and which should move slowly. He shares how he decided when to introduce processes at Rippling, when to keep things informal, and how to recognize when a process that once helped the company had started to slow it down.We discuss how his role changed as Rippling grew from around 70 people to 100, then to 500, and now to thousands. He explains what he paid attention to at each stage and which metrics he deliberately did not obsess over.These are practical lessons for founders, from the earliest days of a startup to the challenges of scaling a large organization.0:00 - Trailer01:11 – One thing people get wrong about building a business?04:01 – Great founders find markets that already exist06:36 – What does a “death march” mean at Apple?10:11 – How to build a good team in early-stage startup?12:33 – Learnings from Apple to Inkling18:11 – Processes to set up in startups25:20 – Humans always optimize for comfort (and why that's bad instinct)33:09 – Why success teaches you more than failure36:01 – How should processes change as company scales?42:11 – How is AI changing the software industry?54:03 – If Matt were starting up today, how would he do it?57:07 – How would Next-gen PM roles look like?01:01:51 – Matt shares about Rippling CEO Parker01:04:32 – Founder instinct vs Data01:06:06 – Over-optimizing for employee comfort01:07:27 – If building a startup feels comfortable, it's probably dead01:08:36 – One thing only CEO's should do forever01:11:15 – One piece of startup advice Matt doesn't trust-------------India's talent has built the world's tech—now it's time to lead it.This mission goes beyond startups. It's about shifting the center of gravity in global tech to include the brilliance rising from India.What is Neon Fund?We invest in seed and early-stage founders from India and the diaspora building world-class Enterprise AI companies. We bring capital, conviction, and a community that's done it before.Subscribe for real founder stories, investor perspectives, economist breakdowns, and a behind-the-scenes look at how we're doing it all at Neon.-------------Check us out on:Website: https://neon.fund/Instagram: https://www.instagram.com/theneonshoww/LinkedIn: https://www.linkedin.com/company/beneon/Twitter: https://x.com/TheNeonShowwConnect with Siddhartha on:LinkedIn: https://www.linkedin.com/in/siddharthaahluwalia/Twitter: https://x.com/siddharthaa7-------------This video is for informational purposes only. The views expressed are those of the individuals quoted and do not constitute professional advice.Send us a text

Get ready for a high-octane episode, as Joel Cheesman and Emi Beredugo take the mic to dissect everything from "bougie" McDonald's Valentine's stunts to the high-stakes world of Big Tech. The duo dives deep into Rippling's bold Super Bowl debut featuring Tim Robinson, debating whether the "evil genius" move is a brilliant recruitment play or a calculated nod to Wall Street. While Microsoft celebrates a massive LinkedIn revenue milestone—proving the platform has officially pivoted from a resume database to a short-form video powerhouse—the hosts shift gears to the grittier side of the job hunt. From the rise of "Resume Botox" and ageism to the "resume slop" currently clogging AI-driven hiring funnels, the gloves come off. Plus, don't miss the heated critique of ZipRecruiter's new "Be Seen First" feature, which Emi and Joel argue might be doing more harm than good for the modern candidate. Chapters 00:00 - Introduction and Super Bowl Excitement 05:04 - The Beckham Family Drama 08:58 - Valentine's Day Fast Food Promotions 14:09 - Rippling's Super Bowl Ad 22:01 - LinkedIn's Revenue Growth and Strategy 27:57 - The Rise of Resume Botox and Ageism in Job Market 30:58 - The Age Discrimination Dilemma 35:59 - AI's Impact on Hiring Practices 45:00 - The Clumsy Evolution of Recruitment 56:04 - ZipRecruiter's Controversial New Feature

The Shred is a weekly roundup of what's making headlines in the world of employment. The Shred is brought to you today by Jobcase.

In this episode, Jason Bay sits down with Rippling's VP of Sales Enablement, Jonas Master to explore how effective sales training, paired with clear priorities, measurement, and reinforcement, drives real behavior change and consistent performance gains. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

Today on the Newcomer Podcast, we're at MongoDB.Local for a series of conversations on how enterprise AI is actually being built.MongoDB CEO CJ Desai joins the show 65 days into the role to explain why San Francisco is “back,” how MongoDB is repositioning itself for the AI era, and why unstructured data has made the company's platform a natural foundation for AI-native applications. He shares his view on the AI hype cycle, the rapid rise of companies like OpenAI and Anthropic, and why MongoDB is staying model-agnostic as AI product cycles accelerate.We also sit down with Rippling's Head of AI Ankur Bhatt to discuss how AI is being deployed inside a live enterprise system. The conversation covers building agents across payroll, IT, and finance, why agent identity and accountability matter, and how Rippling is approaching permissions, access control, and AI-driven productivity at scale.A grounded look at the enterprise AI stack, from the data layer to real-world deployment.MongoDB #Rippling #AIAgents #VentureCapital

In this episode, Carlos Gonzalez de Villaumbrosia, CEO & Founder at Product School, interviews Anique Drumright, General Manager and VP of Product at Rippling, the workforce management platform valued at $16.8 billion with over $570 million in ARR.Anique is a product veteran who has shaped high-growth teams at Uber, TripActions, and Loom. Now at Rippling, she helps lead a workforce of over 4,000 employees, including 100 former founders, to maintain the speed and ownership typically lost at scale. In this conversation, Anique breaks down how Rippling successfully operates as a compound startup and why product leaders must evolve into General Managers.What you'll learn:How to pivot from managing a backlog to owning a P&L as a GM.The Compound Startup framework for consolidating enterprise categories.How to build high-performing teams by hiring for "founder-level" curiosity.Strategies for proving ROI to enterprise customers to drive platform adoption.Key takeaways:Go and See: Why leaders must personally investigate customer issues to set the bar for quality.Singular Obsession: How to organize teams to maintain focus and velocity as you scale.Automating ROI: How Rippling uses product efficiency to justify headcount reduction for clients.Credits:Host: Carlos Gonzalez de VillaumbrosiaGuest: Anique DrumrightSocial Links: Follow our Podcast on Tik Tok here Follow Product School on LinkedIn here Join Product School's free events here Find out more about Product School here

THIS is how you keep your infrastructure costs from spiraling out of control. Today, we're talking to Albert Strasheim, CTO at Rippling. We discuss the cost crisis facing CTOs in the age of AI, how he reduced infrastructure costs by 30% while growing traffic by 25%, and why holding back feedback is actually the most selfish thing a leader can do. All of this right here, right now, on the Modern CTO Podcast!  To learn more about Rippling, check out their website here.

Lenny's Podcast: Product | Growth | Career ✓ Claim : Read the notes at at podcastnotes.org. Don't forget to subscribe for free to our newsletter, the top 10 ideas of the week, every Monday --------- Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you've gone too far3. Matt's transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion's success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling's vision and success(01:17:48) AI's impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman's website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I'm Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Lenny's Podcast: Product | Growth | Career ✓ Claim Key Takeaways Deliberately understaff projects: Constraints force creativity and prevent bloat from politics and bureaucracyYou've gone too far when teams can't ship basic functionalityThe sweet spot is uncomfortable but productive tensionGood teams get tired; great teams run in the red constantly and destroy good teams in that momentHigh alpha, low beta framework: Evaluate people and processes on upside potential (alpha) versus volatility (beta)Prioritize high alpha opportunities even with higher betaProcesses exist solely to lower beta but suppress alpha as a trade-offThe nuanced dance is decreasing volatility where needed (like payroll) without killing upside in innovation areasKnow when to quit your startup: If you're not certain you have product-market fit, you don't have itCompanies that hit big do so quickly; the “never quit” mentality is VC propaganda designed to extract value from founders, not protect themPivot twice or three times maximum, typically by year fourYou're running an experiment to see if the universe has binding receptors for your product. If not, move on… Leadership means fighting entropy relentlesslyTeams naturally optimize for local comfort and disorderExecutives must demand 99% energy levels daily, or the system decaysTop performers don't get 10% more rewards; they get 10-100xBeing “chill” accomplishes nothingWithholding negative feedback is selfish because you prioritize your comfort over making teammates and the company better Read the full notes @ podcastnotes.orgMatt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you've gone too far3. Matt's transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion's success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling's vision and success(01:17:48) AI's impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman's website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I'm Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

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The Legion of Doom (LoD) wasn't just a “hacker group”, it captured the essence of underground hacking in the 80s/90s. BBSes, phreaking, rival crews, and the crackdowns that changed everything. From those humble beginnings came a legacy that still echoes through modern security culture today.SponsorsSupport for this show comes from ThreatLocker®. ThreatLocker® is a Zero Trust Endpoint Protection Platform that strengthens your infrastructure from the ground up. With ThreatLocker® Allowlisting and Ringfencing™, you gain a more secure approach to blocking exploits of known and unknown vulnerabilities. ThreatLocker® provides Zero Trust control at the kernel level that enables you to allow everything you need and block everything else, including ransomware! Learn more at www.threatlocker.com.This show is sponsored by Rippling. Rippling is the unified platform for Global HR, Payroll, IT, and Finance. They've helped millions replace their mess of cobbled-together tools with one system designed to give leaders clarity, speed, and control. With Rippling, you can run your entire HR, IT, and Finance operations as one, or pick and choose the products that best fill the gaps in your software stack. Learn more rippling.com/darknet.This show is sponsored by Meter, the company building networks from the ground up. Meter delivers a complete networking stack - wired, wireless, and cellular - in one solution that's built for performance and scale. Meter's full-stack solution covers everything from first site survey to ongoing support, giving you a single partner for all your connectivity needs. Go to meter.com/darknet to book a demo now!Sources Book: Masters of Deception (https://amzn.to/4q3O0gJ) Book: The Hacker Crackdown (https://amzn.to/3N4bovY)

At the end of Michael's first Wavemaker Conversation with psychiatrist Irvin Yalom, in 2015, Michael extracted a promise: that Dr. Yalom would join him for another conversation after Yalom completed his memoir. Two years later, Dr. Yalom released his memoir, and kept his promise.Irvin Yalom is a highly esteemed psychoanalyst, with a large, devoted following; a Professor Emeritus at Stanford University; and a best-selling author. Among his most influential books is “Staring At The Sun: Overcoming the Terror of Death.”Michael is bringing this conversation with Dr. Yalom and the previous one (entitled 50,000 Hours Of Therapy) out of the Wavemaker archives because he hopes and believes that they will provide fuel for a fulfilling 2026.https://wavemaker.me

Your brand isn't losing to competitors, it's getting flattened by “good enough.”In a world where AI can generate passable B2B content in seconds, bland isn't safe. It's fatal.In this episode, Dan Schwer of Rippling breaks down what brand actually looks like inside a 6.000-person SaaS company with a creative team of 15. We go straight at the uncomfortable stuff: why “brand vs. demand” is a lazy (and expensive) debate, how a brand refresh becomes a business lever (not a design hobby), and what it takes to keep quality high when the org is moving at startup speed and the pipeline still wants receipts.If you're still treating brand as the “pretty layer” on top of performance, this one's going to sting — in a useful way.We also cover:Brand ROI without the fantasy math: Measuring impact through speed, scale, and craft.The “brand vs. demand” trap: Why the fight is fake — and what actually drives pipeline.Video as the new moat: Product launches, customer stories, and earning attention in B2B.AI won't fix bad taste: Where AI helps, where it slows you down, and why judgment still wins.

2025 didn't just shake HR and recruiting. Nope, it yanked the curtain back and lit the place on fire. This year-in-review isn't about press releases and keynote fluff. It's about what really went down when the doors were closed: job boards locking down your hiring data like it's nuclear codes, HR tech rivals apparently confusing “competition” with espionage, private equity strip-mining legacy platforms,and founders playing 4D chess while employees got stuck paying the entry fee. From Indeed trying to own the entire hiring pipeline, to the Rippling vs. Deel spy thriller nobody asked for, to Monster France shutting its doors while exec bonuses stayed warm, to Job.com's bankruptcy unfolding like reality TV — none of this is theoretical. It all happened. Add AI agents ghosting resumes, Slack messages turning into courtroom exhibits, LinkedIn becoming a credibility minefield, and recruiters caught in the blast radius wondering how the hell this became their job. Welcome to 2025's Wrap-Up Show. HR's messiest season yet.

Jason Lemkin is the founder of SaaStr, the world's largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn't, and how the GTM landscape is quickly being transformed.We discuss:1. How AI is fundamentally changing the sales function2. Why most SDRs and BDRs will be “extinct” within a year3. What Jason is observing across his portfolio about AI adoption in GTM4. How to become “hyper-employable” in the age of AI5. The specific AI tools and tactics he's using that have been working best6. Practical frameworks for integrating AI into your sales motion without losing what works7. Jason's 2026 predictions on where SaaS and GTM are heading next—Brought to you by:DX—The developer intelligence platform designed by leading researchersVercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the webDatadog—Now home to Eppo, the leading experimentation and feature flagging platform—Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation—Where to find Jason Lemkin:• X: https://x.com/jasonlk• LinkedIn: https://www.linkedin.com/in/jasonmlemkin• Website: https://www.saastr.com• Substack: https://substack.com/@cloud—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jason Lemkin(04:36) What SaaStr does(07:13) AI's impact on sales teams(10:11) How SaaStr's AI agents work and their performance(14:18) How go-to-market is changing in the AI era(19:19) The future of SDRs, BDRs, and AEs in sales(22:03) Why leadership roles are safe(23:43) How to be in the 20% who thrive in the AI sales future(28:40) Why you shouldn't build your own AI tools(30:10) Specific AI agents and their applications(36:40) Challenges and learnings in AI deployment(42:11) Making AI-generated emails good (not just acceptable)(47:31) When humans still beat AI in sales(52:39) An overview of SaaStr's org(53:50) The role of human oversight in AI operations(58:37) Advice for salespeople and founders in the AI era(01:05:40) Forward-deployed engineers(01:08:08) What's changing and what's staying the same in sales(01:16:21) Why AI is creating more work, not less(01:19:32) Why Jason says these are magical times(01:25:25) The "incognito mode test" for finding AI opportunities(01:27:19) The impact of AI on jobs(01:30:18) Lightning round and final thoughts—Referenced:• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org• SaaStr Annual: https://www.saastrannual.com• Delphi: https://www.delphi.ai/saastr/talk• Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/• Vercel: https://vercel.com• What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• ElevenLabs: https://elevenlabs.io• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack• Bolt: https://bolt.new• Lovable: https://lovable.dev• Harvey: https://www.harvey.ai• Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence• UiPath: https://www.uipath.com• Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser• Agentforce: https://www.salesforce.com/form/agentforce• SaaStr's AI Agent Playbook: https://saastr.ai/agents• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan• Brian Halligan's AI: https://www.delphi.ai/minds/bhalligan• Sierra: https://sierra.ai• Fin: https://fin.ai• Deccan: https://www.deccan.ai• Artisan: https://www.artisan.co• Qualified: https://www.qualified.com• Claude: https://claude.ai• HubSpot: https://www.hubspot.com• Gamma: https://gamma.app• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b• Brex: https://www.brex.com• Outreach: https://www.outreach.io• Gong: https://www.gong.io• Salesloft: https://www.salesloft.com• Mixmax: https://www.mixmax.com• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr• Clay: https://www.clay.com• Owner: https://www.owner.com• Momentum: https://www.momentum.io• Attention: https://www.attention.com• Granola: https://www.granola.ai• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Palantir: https://www.palantir.com• Databricks: https://www.databricks.com• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan• Rippling: https://www.rippling.com• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna• Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza• Sora: https://openai.com/sora• Reve: https://app.reve.com• Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/• The Revenue Playbook: Rippling's Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you've gone too far3. Matt's transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion's success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling's vision and success(01:17:48) AI's impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman's website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I'm Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

A modern sales enablement strategy isn't about more activity - it's about better preparation. In this episode of B2B Sales Trends, we explore why preparation has become the true differentiator in B2B selling and enterprise sales strategy. In this conversation, host Harry Kendlbacher sits down with Gena Dakos, a seasoned sales enablement leader, to unpack how high-quality outreach, customer empathy, and thoughtful preparation help sellers stand out in a noisy, AI-driven market. From executive discovery to enterprise-scale deals, this episode reframes enablement as confidence, clarity, and credibility - not just training.

Welcome to the podcast, Rippling IT, who are working on a novel solution for full lifecycle management related to the devices that their platform enables. Hosts: Tom Bridge - @tbridge@theinternet.social Selina Ali - LinkedIn Guests: Zaafir Kherani - LinkedIn Sponsors: Iru 1Password Backblaze Meter Watchman Monitoring If you're interested in sponsoring the Mac Admins Podcast, please email podcast@macadmins.org for more information. Get the latest about the Mac Admins Podcast, follow us on Twitter! We're @MacAdmPodcast! The Mac Admins Podcast has launched a Patreon Campaign! Our named patrons this month include Weldon Dodd, Damien Barrett, Justin Holt, Chad Swarthout, William Smith, Stephen Weinstein, Seb Nash, Dan McLaughlin, Joe Sfarra, Nate Cinal, Jon Brown, Dan Barker, Tim Perfitt, Ashley MacKinlay, Tobias Linder Philippe Daoust, AJ Potrebka, Adam Burg, & Hamlin Krewson  

The Topline team interview Ethan Smith, founder of Graphite, an San Fransico-based growth and SEO agency with clients like Notion, Webflow and Rippling. As well as Rahul Jain from Noble, a consultant who writes and speaks about AI. Thanks for tuning in! Catch new episodes every Wednesday. Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Chapters: 00:00 Introduction and Host Introductions 00:41 How Well Do You Know AI Search? 08:14 SEO vs. AI: The Changing Landscape 13:42 The Role of PR in AI Search 14:46 Get Cited By THESE Websites 18:13 SEO Strategies in the AI Era 25:07 Is SEO Actually Dead? 33:16 HubSpot's Message to The Market 34:27 SEO Evolution and Traffic Trends 34:54 The Future of Search and LLMs 36:34 Signs You Have The Wrong Product 40:01 Scaling AI Search Content 46:38 The Role of PR and AI in Marketing 01:01:42 What Have You Learned?  

Blake breaks down how AI can help with cost segregation and explains why AI currently works best on tasks that take humans 2-5 minutes. Michael Burry is betting against AI companies, claiming they're manipulating earnings by stretching server depreciation from 3-4 years to 5-6 years, adding billions to their bottom lines. Also covered: Intuit's $100 million annual OpenAI deal to integrate QuickBooks and TurboTax into ChatGPT, new bank evidence in the Rippling corporate espionage case, and a survey showing 10% of adults are acting on AI tax advice despite error rates up to 50%.SponsorsOnPay - http://accountingpodcast.promo/onpayRelay - http://accountingpodcast.promo/relayCloud Accountant Staffing - http://accountingpodcast.promo/casChapters(00:00) - Welcome to The Accounting Podcast (00:49) - Blake's Illness and Recovery (02:05) - Upcoming Topics (04:06) - Cost Segregation Explained (06:46) - AI in Cost Segregation (11:15) - AI's Current Capabilities and Limitations (19:10) - Intuit's OpenAI Deal (22:01) - Intuit's Strategy and Industry Implications (30:12) - Michael Burry's New Bet Against AI (31:21) - Depreciation and AI Companies (39:15) - Rippling vs. Deel: Corporate Espionage (42:44) - New Jersey's Alternative Pathways Bill (44:39) - AI's Role in Tax and Investing Advice (47:37) - Defining Audit Quality: PCOB's New Initiative (51:56) - FASB's Costly Lease Standard (56:13) - Ancient Accounting Systems in Peru (58:45) - Conclusion and Viewer Interaction  Show NotesComing soon!Need CPE?Get CPE for listening to podcasts with Earmark: https://earmarkcpe.comSubscribe to the Earmark Podcast: https://podcast.earmarkcpe.comGet in TouchThanks for listening and the great reviews! We appreciate you! Follow and tweet @BlakeTOliver and @DavidLeary. Find us on Facebook and Instagram. If you like what you hear, please do us a favor and write a review on Apple Podcasts or Podchaser. Call us and leave a voicemail; maybe we'll play it on the show. DIAL (202) 695-1040.SponsorshipsAre you interested in sponsoring The Accounting Podcast? For details, read the prospectus.Need Accounting Conference Info? Check out our new website - accountingconferences.comLimited edition shirts, stickers, and other necessitiesTeePublic Store: http://cloudacctpod.link/merchSubscribeApple Podcasts: http://cloudacctpod.link/ApplePodcastsYouTube: https://www.youtube.com/@TheAccountingPodcastSpotify: http://cloudacctpod.link/SpotifyPodchaser: http://cloudacctpod.link/podchaserStitcher: http://cloudacctpod.link/StitcherOvercast: http://cloudacctpod.link/OvercastClassifiedsCollective by DBA - https://collective.cpa/ Want to get the word out about your newsletter, webinar, party, Facebook group, podcast, e-book, job posting, or that fancy Excel macro you just created? Let the listeners of The Accounting Podcast know by running a classified ad. Go here to create your classified ad: https://cloudacctpod.link/RunClassifiedAdTranscriptsThe full transcript for this episode is available by clicking on the Transcript tab at the top of this page

Nasdaq bleibt trotz starker Nvidia-Zahlen volatil. Google bringt Gemini 3 Pro als neues Spitzenmodell auf eigenen TPUs und führt mehrere Benchmarks an. Anthropic verdoppelt seine Bewertung binnen drei Monaten; Microsoft und Nvidia investieren Milliarden. Perplexity startet ein kostenloses Shopping-Tool, bleibt aber ohne klares Geschäftsmodell. Nvidia meldet erneut starkes Wachstum und optimistische Guidance. Baidu kämpft trotz KI-Trend mit rückläufigem Umsatz. Klarnas erste Zahlen seit dem IPO enttäuschen. PDD warnt vor Abschwächung, Temu unter Druck durch neue Importregeln. Larry Summers verlässt das OpenAI-Board. Bei Deel taucht ein Bestechungsskandal auf. Grok lobt Elon Musk überschwänglich. Lutnicks Familie profitiert von KI-Deals. Android Quick Share wird mit iOS AirDrop kompatibel. Unterstütze unseren Podcast und entdecke die Angebote unserer Werbepartner auf ⁠⁠⁠⁠⁠doppelgaenger.io/werbung⁠⁠⁠⁠⁠. Vielen Dank!  Philipp Glöckler und Philipp Klöckner sprechen heute über: (00:00:00) Intro & Nasdaq Volatilität nach Nvidia Earnings (00:03:19) Google Gemini 3 Pro Launch ohne Nvidia-Chips (00:06:32) Anthropic $350B Deal (00:20:34) Perplexity (00:30:08) Nvidia Earnings (00:38:30) Baidu Earnings (00:40:06) Klarna Earnings (00:47:20) PDD Earnings (00:53:53) Larry Summers tritt nach Epstein-Files zurück (00:57:35) Deel Bestechungsskandal gegen Rippling (01:01:34) Grok (01:06:19) Familie Lutnick (01:09:10) Android Quick Share mit iOS AirDrop kompatibel Shownotes US-Tech-Aktien fallen bei Volatilitätsschub an der Wall Street – ft.com Google bringt Gemini 3 heraus, sein bisher 'intelligentestes' KI-Modell – theverge.com Anthropic kooperiert mit NVIDIA und Microsoft, expandiert auf Azure – linkedin.com Anthropic auf $350 Milliarden geschätzt nach Investition von Microsoft, Nvidia – cnbc.com Perplexity kündigt kostenloses Produkt zur Vereinfachung des Online-Shoppings an – cnbc.com Nvidia-Aktien steigen aufgrund unerwartet starker Umsätze und Prognose – cnbc.com Baidu verzeichnet trotz KI-Boom den größten Umsatzrückgang – bloomberg.com Anmelden bei Similarweb Plattform – pro.similarweb.com Klarna übertrifft Umsatzschätzungen im ersten Quartalsbericht seit IPO – cnbc.com Temu-Eigentümer PDD warnt vor Abschwächung in Chinas Konsumsektor – bloomberg.com Musk's xAI baut 500 Megawatt Rechenzentrum in Saudi-Arabien – bloomberg.com Larry Summers tritt aus OpenAI-Vorstand zurück – axios.com Charles Rollet über X: Deel verbuchte angebliches $6k Bestechungsgeld als Geschäftsausgabe – x.com Groks Verehrung von Elon Musk wird seltsam – theverge.com Familienangelegenheit: Söhne des Handelsministers profitieren vom KI-Boom – nytimes.com Android Quick Share jetzt kompatibel mit iOS AirDrop – blog.google

Max Altman is Co‑Founder & Managing Partner at Saga Ventures, a US$125 M early‑stage fund.  Before Saga Max was an investor with Apollo Projects, Hydrazine Capital and Altman Capital (where he helped deploy over US$500 M) into breakout names such as Rippling and Reddit. AGENDA: 03:55 – Venture Capital Is FULL of Tourists With Single-Digit IQs 06:20 – Inside the Madness of Parker Conrad: Genius, Chaos, and WTF Emails 10:35 – The Rippling Deal That Changed Everything 12:40 – Living in Sam Altman's Shadow: The Confession 17:30 – $200M Fund Mistakes: Max's Brutal Lessons From Hydrazine 22:05 – The $2B Reddit Return… and the $2B Left on the Table 25:00 – Why Climate Tech Is a Total VC Mirage 28:40 – The New Seed War: Can Anyone Survive Sequoia & Andreessen? 46:55 – Max's Boldest Predictions  

Why do billions of dollars of stock trade hands based on napkin math and vibes? Billy Gallagher, CEO of Prospect and former Rippling employee, joins Patrick McKenzie (patio11) to walk through the information asymmetry that costs less-sophisticated employees massive amounts of money. From understanding when to early exercise options to navigating 83B elections and tender offers, they discuss the critical decisions that have a shot clock ticking the day you sign your offer letter.–Full transcript available here: www.complexsystemspodcast.com/understanding-equity-at-tech-companies/–Sponsor: Framer is a design and publishing platform that collapses the toolchain between wireframes and production-ready websites. Design, iterate, and publish in one workspace. Start free at framer.com/design with code COMPLEXSYSTEMS for a free month of Framer Pro.–Links:Prospect: www.joinprospect.com/–Timestamps:(00:00) Intro(00:44) Billy's professional journey(01:07) Equity management challenges(02:29) The importance of equity compensation(04:53) Equity grant structures in startups(06:09) Understanding vesting terms(07:09) The value of equity over time(08:48) The myth of options as lottery tickets(11:23) Career tailwinds from startup experience(14:25) Breaking into the tech industry(15:16) The role of equity in compensation(17:49) Employee equity plans and dilution(19:59) Sponsor: Framer(21:06) Stock options vs. RSUs(21:55) The decision to exercise options(27:11) Tax implications of exercising options(33:03) The role of HR in equity management(36:14) Bootleg spreadsheets and vibes-based investing(38:09) Navigating tax complexities in different scenarios(41:31) The importance of extended exercise windows(44:18) Challenges with tax residency and remote work(49:43) The role of accountants in managing equity(53:41) Understanding the 83(b) election and QSBS(01:01:03) Tender offers and secondary sales(01:08:38) Strategies for exercising and selling options(01:12:28) Navigating financial decisions in startups(01:16:59) Wrap

Side A of StrangeCast Episode 120 debuted earlier this week and Adnan Riaz and Adam Evalt are BACK for the Side B part of Player 1 vs The World's podcast episode. The Lost Records Journal co-hosts continue their talk around the aftermath of Life Is Strange: Double Exposure publisher Square Enix dropping its bombshell news on the U.S. and UK-based divisions of the Japanese company.

Arjun Sethi is co-CEO of Kraken, one of the most secure and enduring cryptocurrency platforms. He is also Chairman of Tribe Capital, a leading venture capital firm managing $1.7B in assets, with investments in Block, OpenAI, Rippling, Slack and xAI among others.Previously, Arjun was a Partner at Social Capital, where he led the venture team. He co-founded two startups—LOLapps (acquired by 6waves) and MessageMe (acquired by Yahoo). He joined Yahoo's executive team to lead data and analytics teams and run mobile and emerging products. He also served as a Board Observer, helping to oversee the investment in Alibaba. Arjun has also incubated and co-founded Termina.ai, Kapital, and Foundation Robotics.

Alicia Katz Pollock joins the show fresh from Intuit Connect with detailed notes on everything announced for QuickBooks Online and the accounting profession. The discussion covers Intuit's consolidation strategy to reduce reliance on third-party apps, the new tiered pricing structure for the Intuit Accountant Suite launching in 2026, and how AI agents are currently performing in bank feeds and transaction categorization. They also examine QuickBooks' move into CRM and marketing tools, the role of QuickBooks Live in Intuit's strategy, and what alternatives small businesses and accountants might consider.SponsorsCloud Accountant Staffing - http://accountingpodcast.promo/cas Rippling - http://accountingpodcast.promo/ripplingBILL - http://accountingpodcast.promo/billChapters(00:00) - Introduction and Guest Welcome (00:56) - Intuit Connect Conference Overview (01:32) - Changes in QuickBooks and Intuit's Strategy (02:03) - AI Integration in QuickBooks (05:26) - The New Customer Hub and MailChimp Integration (06:54) - Concerns About AI and QuickBooks Ecosystem (12:10) - ProAdvisors' Role in the AI Era (19:44) - Addressing Reporting and Automation Issues (27:43) - The Future of QuickBooks Online Accountant (28:21) - New Features and Paid Tiers (29:24) - Intuit Accountant Suite Overview (30:40) - Core and Accelerate Versions (30:54) - Client Management and Dashboards (33:22) - Practice Management Tools (34:01) - Intuit's Market Strategy (38:04) - ProAdvisor and QuickBooks Live (40:31) - Quicken's Comeback (43:34) - AI and Automation in Accounting (53:52) - Intuit's Future Plans and Innovations (56:44) - Conclusion and CPE Information  Show NotesComing soon!Listen and Subscirbe to The Unofficial QuickBooks Accountants Podcast!https://uqb.show/subscribeConnect with Alicia Katz Pollock!https://www.linkedin.com/in/aliciakatzpollock/https://royalwise.com/ Need CPE?Get CPE for listening to podcasts with Earmark: https://earmarkcpe.comSubscribe to the Earmark Podcast: https://podcast.earmarkcpe.comGet in TouchThanks for listening and the great reviews! We appreciate you! Follow and tweet @BlakeTOliver and @DavidLeary. Find us on Facebook and Instagram. If you like what you hear, please do us a favor and write a review on Apple Podcasts or Podchaser. Call us and leave a voicemail; maybe we'll play it on the show. DIAL (202) 695-1040.SponsorshipsAre you interested in sponsoring The Accounting Podcast? For details, read the prospectus.Need Accounting Conference Info? Check out our new website - accountingconferences.comLimited edition shirts, stickers, and other necessitiesTeePublic Store: http://cloudacctpod.link/merchSubscribeApple Podcasts: http://cloudacctpod.link/ApplePodcastsYouTube: https://www.youtube.com/@TheAccountingPodcastSpotify: http://cloudacctpod.link/SpotifyPodchaser: http://cloudacctpod.link/podchaserStitcher: http://cloudacctpod.link/StitcherOvercast: http://cloudacctpod.link/OvercastClassifiedsCollective by DBA - https://collective.cpa/ Want to get the word out about your newsletter, webinar, party, Facebook group, podcast, e-book, job posting, or that fancy Excel macro you just created? Let the listeners of The Accounting Podcast know by running a classified ad. Go here to create your classified ad: https://cloudacctpod.link/RunClassifiedAdTranscriptsThe full transcript for this episode is available by clicking on the Transcript tab at the top of this page

High-volume recruiting is officially in its “everything is on fire” era. Applicant fraud is exploding. Screening is eating recruiter calendars alive. And scaling sourcing without torching your team? Good luck doing that manually in 2025 and beyond. So we're bringing in the people who actually lived it… not analyst fantasy land. In this session — leaders from Rippling, Phantom, Foley and more break down the pain they actually felt, the bad solutions they tried first, and how they finally got ahead of the chaos. You'll hear exactly how the speakers have taken a native approach in catching fraud before it infects pipelines, shrink screening overhead, and put recruiter time back into outbound sourcing where it actually moves the needle — not “spreadsheet archaeology.” Speakers include: Vijay Mani — Co-Founder & CEO, Covey Jay Patel — Sr Director Talent, Rippling (ex DoorDash) Laura Stapleton — VP People, Foley (ex Engine) Derrick Gellidon — Head of Talent, Phantom (ex Lyft, Instacart) And yes… Chad & Cheese stirring the bourbon into the chaos.

Blake and David cover BDO's legal threat against Going Concern over independence questions, Crowe hiring an investment bank to explore private equity options, and Trump pardoning Binance founder after the crypto venture made his family richer than their entire property portfolio. Plus, tariffs create a paperwork nightmare for small businesses, accounting ranked 90th out of 100 best jobs, a film production accountant who embezzled $2 million for Vegas stays and sugar daddy payments, and the Supreme Court hearing arguments on whether Trump's tariffs amount to an illegal $3 trillion tax.SponsorsCloud Accountant Staffing - http://accountingpodcast.promo/cas Rippling - http://accountingpodcast.promo/ripplingChapters(00:00) - Welcome to the Accounting Podcast Live from Intuit Connect (01:16) - Top Story: BDO vs. Going Concern (05:02) - The Fraud Triangle and Independence in Accounting (08:21) - BDO's Response to Allegations (18:02) - Accountants Rank 90th Best Job in the US (19:38) - Stablecoins and Treasury Management (20:28) - Trump Pardons Binance Founder (24:29) - Positive Hiring Outlook in Accounting (25:41) - Impact of Trump's Tariffs (28:44) - Challenges for Small Businesses Due to Tariffs (32:46) - Workplace Friendships and Pay Cuts (34:35) - App News: Keeper Rebrands to Double (37:53) - AI Adoption in Accounting (45:25) - Fraud in Film Production Accounting (48:15) - Private Equity in Accounting Firms (50:49) - Conclusion and Upcoming Events  Show NotesA Message from CEO Wayne Berson to BDO USA Professionals https://www.bdo.com/insights/press-releases/a-message-from-ceo-wayne-berson-to-bdo-usa-professionalsAuditor BDO Cuts Jobs With Focus on Managing Apollo Debt https://www.bloomberg.com/news/articles/2025-10-11/auditor-bdo-cuts-jobs-with-focus-on-managing-apollo-debtAccountants Hold the 90th Best Job in U.S. News & World Report's 2025 Rankinghttps://www.cpapracticeadvisor.com/2025/10/27/accountants-hold-the-90th-best-job-in-u-s-news-world-reports-2025-ranking/171733/Accountant - Career Rankings, Salary, Reviews and Advice https://money.usnews.com/careers/best-jobs/accountantTrump pardons Binance founder Changpeng Zhao, aka "CZ" https://www.cnbc.com/2025/10/23/trump-pardons-binance-founder-cz-zhao.htmlThe Accounting Firm Weighing Private-Equity Ownership After Years of Ignoring Calls https://www.wsj.com/articles/the-accounting-firm-weighing-private-equity-ownership-after-years-of-ignoring-calls-8b7377fcCrowe Ponders PE Investment Amid Middle Market Firm Shake-Up https://news.bloombergtax.com/financial-accounting/crowe-ponders-pe-investment-amid-middle-market-firm-shake-upThe Disproportionate Effects of Declining Interest Within Different Accounting Fields: An Uneven Pipeline (CPA Journal)https://www.cpajournal.com/2025/10/22/the-disproportionate-effects-of-declining-interest-within-different-accounting-fieldsMovie Accountant Charged with Embezzling Nearly $2M From Indie Films https://www.cpapracticeadvisor.com/2025/08/12/movie-accountant-charged-with-embezzling-nearly-2m-from-indie-films/167240/Need CPE?Get CPE for listening to podcasts with Earmark: https://earmarkcpe.comSubscribe to the Earmark Podcast: https://podcast.earmarkcpe.comGet in TouchThanks for listening and the great reviews! We appreciate you! Follow and tweet @BlakeTOliver and @DavidLeary. Find us on Facebook and Instagram. If you like what you hear, please do us a favor and write a review on Apple Podcasts or Podchaser. Call us and leave a voicemail; maybe we'll play it on the show. DIAL (202) 695-1040.SponsorshipsAre you interested in sponsoring The Accounting Podcast? For details, read the prospectus.Need Accounting Conference Info? Check out our new website - accountingconferences.comLimited edition shirts, stickers, and other necessitiesTeePublic Store: http://cloudacctpod.link/merchSubscribeApple Podcasts: http://cloudacctpod.link/ApplePodcastsYouTube: https://www.youtube.com/@TheAccountingPodcastSpotify: http://cloudacctpod.link/SpotifyPodchaser: http://cloudacctpod.link/podchaserStitcher: http://cloudacctpod.link/StitcherOvercast: http://cloudacctpod.link/OvercastClassifiedsCollective by DBA - https://collective.cpa/ Want to get the word out about your newsletter, webinar, party, Facebook group, podcast, e-book, job posting, or that fancy Excel macro you just created? Let the listeners of The Accounting Podcast know by running a classified ad. Go here to create your classified ad: https://cloudacctpod.link/RunClassifiedAdTranscriptsThe full transcript for this episode is available by clicking on the Transcript tab at the top of this page

Outbound prospecting isn't dead, it's just different. TSHP welcomes Jason Bay, outbound sales coach, trainer, and SKO speaker for a conversation about how to outbound smarter. Uncover the math problem haunting sales teams—those dismally low cold call and conversion rates—and explore innovative ways to manage and improve them. Discover how sales reps can benefit from AI tools like ChatGPT for practical, real-world experience, even when live conversations are scarce. Mark and Jason shed light on crafting an effective sales rhythm, and how voicemails can double as marketing messages, guiding prospects to your emails, rather than just seeking callbacks.

Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-quality experiences to business buyers — a lesson that shapes how Serval turns complex IT automation into something that feels magical. In this episode, Jake and Brett dive into the lessons from Verkada that inspired Serval's founding, what it takes to disrupt entrenched enterprise categories, and practical tips for getting deeply embedded with customers and hiring high-quality candidates. In today's episode, we discuss: Why building “in existing categories” can be more powerful than creating new ones The lessons from Verkada that shaped Serval's platform strategy The customer interview question that unlocked the IT buyer's hidden pain points How Serval's automation builder uses AI to generate code-based workflows Redefining engineering and PM roles with forward-deployed engineers Keeping the hiring bar high in an AI-native startup Why there's a “land grab” moment right now in enterprise AI And much more... Where to find Jake: LinkedIn: https://www.linkedin.com/in/jakestauch/ Twitter/X: https://x.com/jakeserval Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Alex McLeod: https://www.linkedin.com/in/alexmcleodio/ Clay: https://www.clay.com Cloudflare: https://www.cloudflare.com Cursor: https://cursor.sh Filip Kaliszan: https://www.linkedin.com/in/kaliszan/ Hans Robertson: https://www.linkedin.com/in/hansrobertson Linear: https://linear.app Okta: https://www.okta.com Rippling: https://www.rippling.com Serval: https://www.serval.com/ ServiceNow: https://www.servicenow.com Verkada: https://www.verkada.com Workday: https://www.workday.com Timestamps: (02:25) Lessons from holding different product roles (07:29) Turning “hard mode” into a moat (10:49) The early days of Serval (12:59) Scratching the founder itch (14:57) Unconventional interview techniques (17:47) Solving core interview challenges (21:10) Planning the early product roadmap (23:03) The surprising power of patience (26:12) Serval's impressive technical advantage (27:35) Disrupting legacy incumbents (31:13) Building for mid-market and enterprise (33:35) Serval's enduring roadmap (36:08) How to sell to an existing market (39:16) The evolving role software plays (43:55) Building for AI that didn't exist yet (49:49) Serval's forward-deployed engineers (58:31) The hybrid PM-GM (1:00:27) “You can over-prioritize” (1:02:48) The unexpected value of panic buttons (1:04:50) What Serval looks for in new talent (1:07:01) The ultimate hiring litmus test (1:13:59) Building out Serval's go-to-market function (1:16:31) The evolving IT market in 2025

Alex Bouaziz is the Co-Founder and CEO @ Deel, the $17BN global payroll juggernaut that just last week announced their latest $300M fundraise led by Ribbit, a16z and Coatue. Deel has been on the most insane journey, they do $1BN+ in ARR, they just had their first $100M revenue month and they have been profitable for over 3 years.  AGENDA: 03:38 Announcing $300M Fundraise at a $17BN Valuation 06:24 Rippling vs Deel: WTF is Going On? Where is the Lawsuit?  14:01 Why 1-1s Are BS and Leaders Should Stop Doing Them 17:31 Do Rich Leaders Make Better Leaders 28:33 Biggest Lesson from Ben Horowitz? Why Most CMOs Are Bad? 34:48 Lessons from Nik @ Revolut and Why Companies Need to Make Their Own Software 42:23 Deel's Acquisition Playbook: Lessons from 13 Acquisitions 45:17 How to Price Acquisitions? How to Align Incentives with Founders? 55:45 Deel is Profitable and Growing Fast: When is the IPO? 01:01:35 Best Acquisition Ever + Worst Ever: What Did We Learn?  

Could an AI catch what auditors and a CFO missed? This week, Blake and David unpack how a founder used Claude to scan QuickBooks and uncover a $2.1M embezzlement in 18 minutes. They also tackle Deloitte's AI ‘workslop' refund, shutdown-driven IRS and air travel woes, the IRS's new “CEO” and crypto ties, OpenAI's personal finance play, EY's audit rebound, BDO's ESOP squeeze, and crypto funds courting CPA clients.SponsorsCloud Accountant Staffing - http://accountingpodcast.promo/cas Rippling - http://accountingpodcast.promo/ripplingAssembly - http://accountingpodcast.promo/assemblyChapters(01:35) - Deloitte's AI Report Scandal (09:05) - Government Shutdown Impact on IRS and Air Travel (23:56) - AI in Accounting: Risks and Opportunities (34:49) - Competing with the Status Quo (35:38) - Pricing Bookkeeping Services (36:31) - Standardizing Services Based on Price (37:14) - Client Needs vs. Service Offerings (38:00) - The Monthly Close Obsession (40:01) - Broken Charts in Financial Reports (43:15) - Cracker Barrel Logo Controversy (47:08) - EY's Audit Quality Turnaround (49:53) - Crypto Investment Schemes (55:48) - BDO's Financial Struggles (01:00:34) - Conclusion and Announcements  Show NotesDeloitte to partially refund Australia for report with apparent AI-generated errors https://abcnews.go.com/Technology/wireStory/deloitte-partially-refund-australian-government-report-apparent-ai-126281611Claude Exposed My Co-Founder's $2M Theft — AI Evidence Turned Into Lawsuit https://techbullion.com/claude-exposed-my-co-founders-2m-theft-ai-evidence-turned-into-lawsuit/New Research: 20% of Americans use AI tools 10X+/month, but growth is slowing and traditional search hasn't dippedhttps://sparktoro.com/blog/new-research-20-of-americans-use-ai-tools-10x-month-but-growth-is-slowing-and-traditional-search-hasnt-dipped/The Danger of Bad Charts https://www.cpajournal.com/2025/10/10/the-danger-of-bad-charts-2/Cracker Barrel's logo controversy was driven by bots https://www.nrn.com/casual-dining/cracker-barrel-s-logo-controversy-was-driven-by-bots-what-operators-should-learn-from-thisOur commitment to audit quality — Ernst & Young LLP's 2025 report https://www.ey.com/en_us/assurance/audit-quality-reportEY drops clients to improve audits after leading Big Four in deficiencies https://www.cfobrew.com/stories/2024/08/27/ey-drops-clients-to-improve-audits-after-leading-big-four-in-deficienciesOpenAI Buys Personal Finance App Roi https://www.pymnts.com/acquisitions/2025/openai-buys-personal-finance-app-roi/With its latest acqui-hire, OpenAI is doubling down on personalized consumer AI https://techcrunch.com/2025/10/03/with-its-latest-acqui-hire-openai-is-doubling-down-on-personalized-consumer-ai/BDO USA Expands Professional Services Capabilities Through HORNE https://www.bdo.com/insights/press-releases/bdo-usa-expands-professional-services-capabilities-through-horneAuditor BDO Cuts Jobs With Focus on Managing Apollo Debt https://www.bloomberg.com/news/articles/2025-10-11/auditor-bdo-cuts-jobs-with-focus-on-managing-apollo-debtNeed CPE?Get CPE for listening to podcasts with Earmark: https://earmarkcpe.comSubscribe to the Earmark Podcast: https://podcast.earmarkcpe.comGet in TouchThanks for listening and the great reviews! We appreciate you! Follow and tweet @BlakeTOliver and @DavidLeary. Find us on Facebook and Instagram. If you like what you hear, please do us a favor and write a review on Apple Podcasts or Podchaser. Call us and leave a voicemail; maybe we'll play it on the show. DIAL (202) 695-1040.SponsorshipsAre you interested in sponsoring The Accounting Podcast? For details, read the prospectus.Need Accounting Conference Info? Check out our new website - accountingconferences.comLimited edition shirts, stickers, and other necessitiesTeePublic Store: http://cloudacctpod.link/merchSubscribeApple Podcasts: http://cloudacctpod.link/ApplePodcastsYouTube: https://www.youtube.com/@TheAccountingPodcastSpotify: http://cloudacctpod.link/SpotifyPodchaser: http://cloudacctpod.link/podchaserStitcher: http://cloudacctpod.link/StitcherOvercast: http://cloudacctpod.link/OvercastClassifiedsCollective by DBA - https://collective.cpa/ Want to get the word out about your newsletter, webinar, party, Facebook group, podcast, e-book, job posting, or that fancy Excel macro you just created? Let the listeners of The Accounting Podcast know by running a classified ad. Go here to create your classified ad: https://cloudacctpod.link/RunClassifiedAdTranscriptsThe ...

“I wouldn't be able to be the Chief Marketing Officer of the company without AI. … It's like having a person expert in marketing that explains things exactly the way I want to understand them.” -Gianluca Ferremi   Gianluca is a technology expert with over 25 years of experience in innovation and digital transformation. He's launched two AR/VR educational apps used by 35,000 students, generated $46.5M in B2B sales, and co-launched the first low-cost Pay TV in South Africa. Specializing in soft skills development, Gianluca believes in an education that values human talent and personal growth. Website: https://www.wisepath.ai/ LinkedIn: https://www.linkedin.com/in/gianlucaferremi/    Most product demos suck. Madhav knows this better than anyone—after a decade in B2B marketing, he's seen thousands of terrible demos kill deals. That's why he leads marketing at Storylane, where 4,000+ teams like Gong, Clari and Rippling now create killer demos in 2 minutes instead of 2 weeks. Website: https://www.storylane.io/ LinkedIn: https://www.linkedin.com/in/madhavbhandari/ YouTube: https://www.youtube.com/@StorylaneOfficial/videos   In this episode, we explore the intersection of education, technology, and storytelling—how innovation in both learning and marketing can unlock growth, impact, and connection.   Apply to join our marketing mastermind group: https://notypicalmoments.typeform.com/to/hWLDNgjz   Follow No Typical Moments at: Website: https://notypicalmoments.com/ LinkedIn: https://www.linkedin.com/company/no-typical-moments-llc/ YouTube: https://www.youtube.com/channel/UC4G7csw9j7zpjdASvpMzqUA Instagram: https://www.instagram.com/notypicalmoments Facebook: https://www.facebook.com/NTMoments

Blake and David examine the growing threat of AI-generated fake receipts, with 32% of accountants unable to recognize fraudulent documents and 30% reporting an increase in fraud since last year. They also discuss the concerning decline in entry-level auditor positions (down 43% since January) as firms adopt AI automation, while nearly half of accounts payable professionals now fear layoffs and also explore the concept of "work slop"—low-quality AI-generated work costing businesses nearly $200 per employee monthly—and debate whether firms should require clients to use standardized technology stacks, with only 37% currently doing so. SponsorsCloud Accountant Staffing - http://accountingpodcast.promo/cas Rippling - http://accountingpodcast.promo/ripplingBill.com - http://accountingpodcast.promo/bill.comBluebook - http://accountingpodcast.promo/bluebookChapters(01:43) - Headline Story: Tech Stack Adoption in Accounting Firms (03:05) - Survey Insights: Tech Stack Usage in Firms (07:15) - AI's Impact on Entry-Level Jobs (13:55) - The Rise of 'Work Slop' and Its Costs (20:44) - AI and Automation in Accounting (25:08) - Human-in-the-Loop Automation with Zapier (28:22) - AI in Tax Research and IT Blockers (30:51) - Competitive Moats and Custom Bots (32:26) - Exciting Changes in CPE Standards (34:59) - Drake Software's Cloud-Based Tax Solution (43:06) - State Department Embezzlement Scandal (44:59) - Trump's Tariff Announcements (50:28) - H-1B Visa Fee Increase (56:20) - Conclusion and CPE Information  Show Notes32% of accountants can't recognize AI-generated fake receipts https://www.accountingtoday.com/news/32-admit-they-cannot-recognize-ai-generated-fake-receiptsEntry-level auditor job postings fell 43%, per Randstad https://www.accountingtoday.com/news/entry-level-auditor-job-postings-fell-43-per-randstadAI-Generated "Workslop" Is Destroying Productivity https://hbr.org/2025/09/ai-generated-workslop-is-destroying-productivity97% say CPA firms not using tech efficiently says survey https://www.accountingtoday.com/news/97-say-cpa-firms-not-using-tech-efficiently-says-surveyCPA.com & BILL Growth Survey: How Firms Plan to Stay Ahead https://www.bill.com/blog/cpa-and-bill-growth-technology-surveyAP Pros Face Growing Layoff Concerns and See Automation as a Career Lifeline https://www.cpapracticeadvisor.com/2025/09/11/ap-pros-face-growing-layoff-concerns-and-see-automation-as-a-career-lifeline-2/168818/Get more control over your workflows with Human in the Loop! https://help.zapier.com/hc/en-us/articles/38838619533069-Get-more-control-over-your-workflows-with-Human-in-the-Loop54% use AI in tax research, but search engines remain prominent https://www.accountingtoday.com/news/54-use-ai-in-tax-research-but-search-engines-remain-prominentDrake Software Introduces Drake Tax Online https://www.cpapracticeadvisor.com/2025/09/24/drake-software-introduces-drake-tax-online/169572/Drake Software Launches Drake Tax Online: Powerful, Flexible Tax Software in the Cloud https://www.prnewswire.com/news-releases/drake-software-launches-drake-tax-online-powerful-flexible-tax-software-in-the-cloud-302566087.htmlNASBA, AICPA release proposed revisions to CPE standards https://www.journalofaccountancy.com/news/2025/sep/nasba-aicpa-release-proposed-revisions-to-cpe-standardsNASBA, AICPA Release Exposure Draft of Proposed Revisions to CPE Standardshttps://nasba.org/blog/2025/09/15/revisions-to-cpe-standards-2025/ H-1B FAQhttps://www.uscis.gov/newsroom/alerts/h-1b-faq Need CPE?Get CPE for listening to podcasts with Earmark: https://earmarkcpe.comSubscribe to the Earmark Podcast: https://podcast.earmarkcpe.comGet in TouchThanks for listening and the great reviews! We appreciate you! Follow and tweet @BlakeTOliver and @DavidLeary. Find us on Facebook and Instagram. If you like what you hear, please do us a favor and write a review on Apple Podcasts or Podchaser. Call us and leave a voicemail; maybe we'll play it on the show. DIAL (202) 695-1040.SponsorshipsAre you interested in sponsoring The Accounting Podcast? For details, read the prospectus.Need Accounting Conference Info? Check out our new website - accountingconferences.comLimited edition shirts, stickers, and other necessitiesTeePublic Store: http://cloudacctpod.link/merchSubscribeApple Podcasts: http://cloudacctpod.link/ApplePodcastsYouTube: https://www.youtube.com/@TheAccountingPodcastSpotify: http://cloudacctpod.link/SpotifyPodchaser:

In this episode of the Dental Boardroom Podcast, host Wes Read, CPA and financial advisor at Practice CFO, continues the discussion on putting your kids on payroll as a smart tax and wealth-building strategy. This time, he dives deeper into how to maximize the benefits by pairing payroll with 529 education savings accounts and Roth IRAs.Key Takeaways:Shifting income for tax savings:Move income from a higher parent tax bracket to your child's 0% bracket (standard deduction in 2025 is $15,750).Saves roughly $3,000–$4,000 per child per year. Over many years, that adds up significantly.Practical execution:Children can start as early as age 6–7 and continue through college years.Create job descriptions and light documentation (e.g., photos, office work, modeling fees) to substantiate employment.Use a modern payroll service (Wes recommends Rippling) to simplify compliance.How to use the payroll funds:Deposit paychecks into the parent's checking account (simpler than setting up child accounts).Direct those funds toward:A custodial Roth IRA (tax-free growth).A 529 education savings account (tax-free growth + tax-free qualified withdrawals).529 Education Plans explained:State-administered plans with varying benefits Utah's “My529” (Vanguard, low-cost index funds) is Wes' favorite.Benefits:Tax-free growth and withdrawals for education.Potential state tax deductions in some states.High contribution limits.Parent-owned accounts are more favorable for financial aid and offer flexibility to transfer funds among siblings.Can cover not just college, but also K–12, trade schools, apprenticeships, and up to $10K in student loan repayment.Suggested split strategy:After payroll and FICA taxes, about $14K remains per child.Example: Fund $7K to a Roth IRA + $7K to a 529 plan, balancing retirement savings with education funding.Risk & compliance notes:Wes has never seen an IRS audit on this strategy in 17+ years, but stresses proper documentation.Pay a fair wage aligned with actual work performed.Always consult your CPA if unsure.Big picture:This is more than just tax savings it's wealth building.Combining small strategies like payroll, home office, auto deductions, and retirement plans can collectively cut taxes by 30–60% (or more) and accelerate financial independence.Why This Matters:By intentionally leveraging tax rules, you can redirect money that would have gone to the IRS into your kids' education, retirement, or family wealth. Over time, these small wins compound into major financial independence.

Howie Liu is the co-founder and CEO of Airtable, the no-code platform valued at around $12 billion. After a viral tweet declared “Airtable is dead” based on incorrect data, Howie led a radical transformation: reorganizing the entire company around AI, becoming an “IC CEO” who codes daily, and achieving over $100 million in free cash flow.What you'll learn:1. The “fast thinking” vs. “slow thinking” team structure that lets Airtable ship AI features weekly (inspired by Daniel Kahneman)2. Why Howie uses AI hourly (not daily) and is Airtable's #1 inference-cost user globally3. Why CEOs must become ICs again in the AI era (and how to restructure your calendar to make it possible)4. Why “playing” with AI tools should be mandatory—Howie tells employees to cancel all meetings for a week to experiment5. The specific skills product managers, engineers, and designers need to develop to succeed in the AI era6. Why evals can kill innovation (and when to use “vibes” instead)—Brought to you by:LucidLink—Real-time cloud storage for teamsDX—The developer intelligence platform designed by leading researchersClaude.ai—The AI for problem solvers and enterprise—Where to find Howie Liu• X: https://x.com/howietl• LinkedIn: https://www.linkedin.com/in/howieliu/• Email: howie@airtable.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Howie Liu and Airtable(04:05) The “Airtable is dead” viral tweet controversy(08:07) The rise of IC CEOs(10:57) AI's paradigm shift in product development(16:27) Specific changes Airtable has made(21:38) Fast- and slow-thinking teams(32:57) The emergence of new form factors in AI models(34:48) Airtable's vision and philosophy(40:20) Empowering teams with AI tools(46:50) Encouraging experimentation and play(50:55) Cross-functional skills in product teams(01:03:35) The importance of evals and open-ended testing(01:08:06) Key strategies for AI-driven success(01:12:43) Counterintuitive startup wisdom(01:22:21) Don't step away from the details that you love(01:25:50) Advice for aspiring engineers and designers(01:30:00) Lightning round and final thoughts—Referenced:• Airtable: https://www.airtable.com/• All In podcast: https://allin.com/• Nikita Bier on X: https://x.com/nikitabier• Figma: https://www.figma.com/• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder and CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper• Every: https://every.to/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Windsurf: https://windsurf.com/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Rippling: https://www.rippling.com/• Omni: https://www.airtable.com/lp/ai-psu-plp• How ChatGPT accidentally became the fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Palantir: https://www.palantir.com/• Harvey: https://www.harvey.ai/• v0: https://v0.dev/• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Replit: https://replit.com/• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Lovable: https://lovable.dev/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Runway Game Worlds: https://play.runwayml.com/login• Sesame: https://www.sesame.com• NotebookLM: https://notebooklm.google• Salesforce: https://www.salesforce.com• Andrew Ofstad on LinkedIn: https://www.linkedin.com/in/aofstad/• Stripe: https://stripe.com/• Eames chair: https://en.wikipedia.org/wiki/Eames_Lounge_Chair• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• IDEO design thinking: https://designthinking.ideo.com/• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• The Studio on AppleTV+: https://tv.apple.com/us/show/the-studio/umc.cmc.7518algxc4lsoobtsx30dqb52• Silicon Valley on HBOMax: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d• Self Edge: https://www.selfedge.com/• Studio D'Artisan: https://www.selfedge.com/studio-dartisan• Whitesville T-shirt: https://store.toyo-enterprise.co.jp/shopbrand/ct48/• Guest Series | Dr. Paul Conti: How to Understand & Assess Your Mental Health: https://www.hubermanlab.com/episode/guest-series-dr-paul-conti-how-to-understand-and-assess-your-mental-health—Recommended books:• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032• Trauma: The Invisible Epidemic: How Trauma Works and How We Can Heal From It: https://us.amazon.com/Trauma-Invisible-Epidemic-Works-Heal/dp/1683647351/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader My guest: Sam Lessin is a Partner at Slow Ventures, with prior experience as Vice President of Product Management at Facebook and CEO of Drop.io. His career highlights include serving as a key executive at Facebook, leading product management efforts, and successfully co-founding Fin. His current role at Slow Ventures involves investing in innovative startups across various sectors, showcasing his expertise in entrepreneurship and venture capital. Notes: Key Learnings The 4:30 AM Advantage – Sam's father would be at his desk by 4:30 AM every day, saying, "It's easy to look smart if you have a several-hour head start on everyone else." Early work creates compounding advantages over time. Either Be Early or Be Late, Don't Be On Time – Father's wisdom about timing and seasons. Start your career super early to get ahead, or strategically wait and come in later. Timing matters more than perfect preparation. Joy as the Ultimate Competitive Advantage – "I just don't think that in the long run, angry people win." Look for joyful people in hiring and partnerships because joy is sustainable while anger burns out. Type Two Fun Builds Resilience – Type 1 fun is enjoyable while doing it (rollercoaster). Type 2 fun "completely sucks while you're doing it, but there's joy on the other side" (climbing mountains, marathons). Entrepreneurs need Type 2 fun experiences. Practice Voluntary Hardship – Sam ran a sub-3-hour marathon and got a pilot's license not for love of activities, but for "practice moments" of perseverance. Creates evidence that you can handle business adversity. Right Person, Right Opportunity, Right Time – Don't ask "is this a great person?" Ask, "Is it the right person at the right moment?" Success requires all three elements to align, not just talent. Write Publicly for Intellectual Receipts – "If you can't write the check, write me the thesis and timestamp it." Writing creates accountability, proves thinking ability, and builds reputation over time. Nobody Knows What They're Doing – Working at Bain taught Sam that even prestigious companies "have no idea what you're doing." This is liberating—you can figure it out too. Big Things Take Time (Slow Ventures Philosophy) – Most success isn't quick wins. Venmo took "so many turns of the crank." Be patient finding the right wind, then sail fast when you catch it. Embrace Being Wrong Most of the Time – Seed investing means "you're mostly wrong, you mostly lose money." Success comes from being very right occasionally, not being right consistently. The Solana 2000x Return Story – Put in $400K, returned 2000x to LPs. Success came from the intersection of thesis (looking for "Ethereum killer") and relationships (following Raj Gokal through multiple startups). Use Humor and Authenticity as Filters – Slow Ventures website looks like a law firm in tuxedos "on purpose." If you don't think it's funny, "you're not who we want to invest in." Writing Pushes Away Wrong People – "I really like to be not liked by the people I don't want to work with." Authentic writing attracts the right people and repels the wrong ones. Manufacturing Hardship for Privileged Kids – "Tiger Dad" sports culture might be a misguided attempt to create necessary adversity for wealthy children who lack natural hardships. I loved the throughline of this whole conversation being about his dad, working exceptionally hard, and having joy and excitement for the journey. Maybe it was the near-death experiences that his dad had that led to that mindset. Regardless, it's something we can all learn from. We want to be around optimistic people who have joy and love for what they're doing… Nobody knows what they're doing. We're all figuring it out as we go. You'll never learn unless you go out and do the thing. Figure it out as you go. Just get started. And iterate. Learn. Try again. And keep going. Advice from Sam – Write publicly. You don't know what you think until you get your thoughts out of your head onto the page. And if you publish them, you have a record of the journey. Also, you might attract someone to work with. That is how Jack Raines (guest on episode #539) caught Sam's attention, and now they work together. Useful Quotes: "It's easy to look smart if you have a several-hour head start on everyone else." "I just don't think that in the long run, angry people win." "Either be early or be late, don't be on time." "The right question is, is it the right person at the right moment?" "Writing is thinking. If you can't write, you can't think." "I feel like a tenured professor of capitalism—responsible to make a lot of money over the long term by being very right every once in a while with permission to be wrong all the time." "One of the most insulting things you can call someone is a market participant." "The beauty of the internet is so big. The right people find you." "Big things take time." "Life's short. Is this really what you're spending your time on?" Apply to be part of my next Learning Leader Circle. Time Stamps: 00:11 Sam's Dad's Unique Career Path 00:39 Life Lessons from My Dad 04:35 The Trade-offs of Hard Work 06:57 Betting on the Right People 07:23 The Importance of Joy in Success 10:39 Overcoming Hardships and Building Resilience 20:40 My Journey: From Harvard to Bain 26:06 Joining Facebook and Learning from Mark Zuckerberg 29:36 Balancing Joy and Competitive Spirit 30:15 The Story of Rippling and Parker 31:48 The Solana Investment Journey 34:33 The Importance of Writing and Public Thought 41:07 The Philosophy Behind Slow Ventures 52:54 Advice for Aspiring Venture Capitalists 55:46 Future Plans

My guest today is Ramtin Naimi. Ramtin is the founder of Abstract Ventures, one of the most talked-about seed funds in Silicon Valley. What makes Ramtin's story so compelling isn't just his firm's remarkable track record—including early investments in Rippling, Solana, and dozens of unicorns—but also the unconventional path he took to get there. From running a hedge fund straight out of high school to filing for bankruptcy at 24, then bootstrapping his way to building a $2 billion AUM venture firm using AngelList and relentless hustle. Our conversation begins in an unexpected place—the art world—where Ramtin has become a sophisticated collector, learning from mentors like Michael Ovitz about market dynamics that surprisingly mirror venture capital. We dive deep into how the art world actually works, and Ramtin explains how these lessons about "masterpieces" apply directly to identifying power-law companies in venture. We go deep on his approach to early-stage investing and how he built Abstract as a co-investment vehicle alongside firms like Sequoia, Benchmark, and Andreessen Horowitz. We explore his portfolio construction model, his philosophy on dilution-sensitive founders, and why he takes upwards of 30 pitch meetings per week to build his "frame of reference." We discuss why Abstract has the highest graduation rate from seed to Series A among all seed funds, and how this competitive advantage compounds over time. This is his first time telling his story, and we discuss the power of pattern recognition, relentless work ethic, and the unique opportunities available to those willing to start from scratch in Silicon Valley. Please enjoy this great conversation with Ramtin Naimi. Colossus Review Profile: Ramtin Naimi For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠here⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:40) Learning from Mentors and Starting to Collect (00:08:50) Parallels Between Art and Venture Capital (00:12:57) Challenges in Art Collecting (00:20:45) The Role of Status in the Art World (00:25:00) Who Makes the Most Money in the Art World? (00:28:19) Abstract Ventures: Early Stage Investing (00:42:34) Starting a Venture Capital Firm from Scratch (00:43:12) Overcoming Bankruptcy and Early Struggles (00:50:34) Evaluating Technical Capabilities and Momentum (01:02:53) Competing for Deals and Building Relationships (01:15:25) The Role of Brand in Venture Capital (01:22:39) Early Life and Entrepreneurial Beginnings (01:28:40) Starting a Hedge Fund and Learning Hard Lessons (01:31:26) Transition to Venture Capital (01:37:19) Building Abstract and Family Life (01:52:03) The Kindest Thing Anyone Has Done For Ramtin