Portfolio Career Podcast

Are you looking to stand out when building your business? Listen to this new episode with Phil and Xandie. You will learn about how Phil developed his unique selling point to clients by talking to them. You will learn about how Xandie decided to start her business and got her initial customers. You will also learn about the importance of relationships and building relationships when building your business. Excited for you to build and grow your Portfolio Career! 

Jenny Rothenberg, Cofounder of Smooth Media, shares real strategies behind sustainable creator monetization. We dive into content-market fit—creating content your audience actually wants rather than chasing viral moments—and why events might be the most underutilized monetization strategy for creators today. Whether you're looking to monetize for the first time or diversify your income streams, this conversation offers actionable insights you can implement immediately.

Are you looking to date? Listen to this Podcast Mixer episode where three people share their stories, experiences, and interests on dating. There is a common theme around the importance of friendship and maintaining a friendship while dating. If you are interested in dating, this episode is for you!

Are you looking to date or find a partner? If so, how are you thinking about it? Ben Von Wong has created a dating framework to help him think about dating. In this episode, you will learn about the framework and the reasons why he created it. You will also learn about the importance of friendship and clear communication in dating.

Are you looking to build a service-based business? For Jess Goldberg, she initially started building her leadership and communication business on the side while working. Her clients loved her work and referrals started to come in, and keep coming in. She found even more success offering a course on Maven, and then the rest became history. In this episode, you will also learn some communication tips and frameworks. Excited for you to build and grow your Portfolio Career!Connect with Jess on LinkedIn!

This episode was special. Chris Schembra is a really good friend. And he is a really good question asker. I wanted to share an update with you and Chris made this happen. We covered a lot of topics that I may not have talked about before. You will learn about prior life chapters and how that has helped shaped who I am today. I hope this episode is interesting to you. Please let me know what you think! Excited for you to build and grow your Portfolio Career!

Are you looking to host dinner parties? Saba Ahmed is the Cofounder of Tiny Dinner, a company that hosts dinner parties in homes. In this episode, you will learn about how many people is good for a dinner party, the importance of curating an attendee list, where dinner parties should be held and so much more! Excited for you to build and grow your Portfolio Career!Connect with Saba on InstagramConnect with David on Instagram

Have you ever been frustrated with a situation? Amanda Pena, creator of The Rules of 30 Instagram account with over 130,000 followers, turned her frustration into impact. Amanda's account went viral, resonating with many women in their 30s. In this episode, you will hear more about her spiky point of view on societal pressures and the benefits of delaying life milestones, and much more. Excited for you to build and grow your Portfolio Career!Follow The Rules of 30 Instagram account hereFollow David's Instagram account here

Are you looking to level-up your life? Listen to this episode to hear Life Hacks from the three people. This episode was recorded at the Life Hacks mini-conference. You will learn about tech tools, ways to improve your email outreach, and so much more! Tune to level-up!

In this episode, we explore the creative process from initial spark to finished work. Discover how creators across all disciplines develop their ideas, use AI, balance structure with spontaneity, and develop resilience. Whether you're a seasoned artist or just beginning your creative journey, join us for practical insights on transforming your ideas into art. This episode was recorded during a Hot Pod Podcast Mixer with 8 or so people. Excited for you to build and grow your Portfolio Career!

Valerie Chapman shares her journey from being laid off twice to becoming a LinkedIn creator, achieving over 120 million impressions in 90 days. Valerie shared how she is leveraging AI to build powerful personal brands on LinkedIn. She also often posts about AI on LinkedIn, and how she saw a gap in the market to do so. Valerie also stresses the need for people to use AI for strategic planning and to brainstorm a bigger life for themselves. If you are looking to level-up and learn about AI, cold email, creating content and video content and more, this episode is for you!Connect with Valerie on LinkedInConnect with David on LinkedIn

Bethany Crystal discusses her transition from a fractional worker to an AI founder. She shares her experience of using AI often in her role at a dev shop and how it saved her life during a near-death experience. Bethany highlights her new app, MuseKat, designed to help parents explain museum exhibits to their kids using AI-generated audio stories. Bethany also reflects on the evolving job market and the need for individuals to adapt and leverage AI tools to stay relevant. She shared how she is building this app as a way of creating a container that works for and excites her while wanting to be part of the growing AI sector. Excited for you to build and grow your Portfolio Career!Connect with Bethany on TwitterConnect with David on Twitter

Can our thoughts truly shape our reality? In this episode, we explore manifestation through many different lenses. Is it the same as goals or something else? In this episode, you will hear 7-8 people discuss this and more. Tune in and maybe you will manifest something :)Connect with David on Instagram!

In this episode, you will hear from Wen-Jay Ying, Founder of Local Roots, a modern CSA that recently ended its core operations after 14 years. Wen-Jay discusses her journey, starting from her passion for local food and her decision to create a business that supports organic and sustainably grown ingredients. She highlights the challenges faced during the pandemic, including increased demand and operational stress. Despite the success, Wen-Jay decided to pivot and is now focused on new business ideas. If you are looking to pivot or start a new chapter, this episode is for you!Connect with David on InstagramConnect with Wen-Jay on Instagram

Are you looking to grow your impact, influence and income? This episode was recorded during the Strategic Storytelling Summit that I cohosted with Terry Rice. In this episode, you will hear three people share about how they are using stories and storytelling as a way to grow. For many of us, telling our story is very important. Listen to this episode to hear about how three people tell their story and more! Excited for you to build and grow your Portfolio Career!Connect with me on IGLearn more on my Substack

In this episode, we dive into the power of collaboration and how communities have grown through with other organizations and communities. During this Podcast Mixer episode, you will hear multiple stories from people sharing real-world stories, practical strategies, and lessons learned. This conversation will give you valuable insights on building and sparking meaningful connections and amplifying your impact. Tune in and discover how working together can make our communities stronger!Let's connect on InstagramLearn more about my work on Substack!

When was the last time you had a hard conversation? What did you learn from it? What did you wish you would've done differently. In this episode, you will hear stories about people having a hard conversation. I hope this episode makes future hard conversations easier. Excited for you to build and grow your Portfolio Career!

In this episode, you will learn from Anne-Laure Le Cunff, Founder of Ness Labs and the author of a new book called Tiny Experiments, about the power of personal experimentation. Anne-Laure shares how she crafted an experiment to write a book on experiments, and explains practical methods for designing your own life experiments. She emphasizes the importance of setting deadlines and embracing uncertainty. She also touches on the emotional aspects of letting go of desired outcomes and her own definition of success. Excited for you to build and grow your Portfolio Career!Learn more about the book Tiny ExperimentsConnect with Anne-Laure on Instagram!Connect with David on Instagram!

Do you know your enneagram type? Have you ever considered how your type impacts your connect with other people. In this episode, Jon Wu talks about the enneagram personality test, why he loves it, and how it can help you better understand yourself. In this episode, we talk about our enneagram types and how they show up in the world, and how to potentially navigate hard conversations. If you are looking for a way to better understand yourself and your relationships, this episode is for you!Connect with Jon on TwitterConnect with David on Twitter

Have you ever made a mistake? Probably, right? Building community is hard and mistakes happen. Listen to this episode where 10 or so community builders shared stories of mistakes, learnings, and how they are thinking about these situations now. Maybe if you aren't making mistakes, you aren't trying hard enough. Excited for you to build and grow your Portfolio Career!

Are you looking to building a community-focused business? Listen to this episode with Emily Chertow, the Founder or Journaling Classes. She has been hosting journaling classes for over 6 years. Since early 2024, she has been full-time on building her business. In this episode, you will hear about starting her community, inflections, and learnings from going full-time. Excited for you to build and grow your Portfolio Career!Learn more about Journaling Classes!Learn more about me!

What does it mean to live an A+ life? Katy Atherholt and I both explored this topic and chatted about it in this podcast episode. After a separate conversation, we both decided to write an essay on this topic and then we discussed it on this podcast. Interestingly, we both had different points of view and could see each other's prospective. Your point of view is likely different too, which is amazing. When you know what A+ looks like, hopefully it means it is easier to live it.Connect with Katy on TwitterConnect with David on Twitter

Kameron Monet is an attorney, content creator, and entrepreneur with over 60,000 Instagram followers and nearly 100,000 YouTube subscribers. She began creating YouTube videos in 2014, initially for fun, and later monetized her content. Kameron posted videos while she had a traditional job as a lawyer and many of them became very popular. She talked about leaving her job, becoming a consultant, and now how she works on her own as a lawyer for content creators. In this episode, you will learn about the power of niche content and how it only takes one video to change your life. We also talked using YouTube and Instagram stories to create community and more. Excited for you to build and grow your Portfolio Career!Learn more from Kameron on InstagramLearn more from David on Instagram

Join us as we explore the art of bouncing back from life's challenges in this powerful episode. This episode was recorded among  8 or so people at a dinner table. You will hear stories from people who turned their setbacks into springboards for growth and learnings. Whether you're dealing with career hurdles, personal struggles, or unexpected detours, this conversation offers valuable insights to help you not just recover, but emerge stronger from life's setbacks.Connect with David on InstagramRead my newsletter here!

In this episode, meet Remington Davenport, who left her career in sales to pursue her passion: creating the world's backgammon club in NYC with the NYC Backgammon Club. Remington shares how she moved to NYC and didn't see any backgammon events that really resonated with her - so she started hosting her own. The word began to spread, and her events started growing in popularity and frequency. So, she decided to go full-time on this. You will learn about her decision to do this, about partnering with venues, and what she has noticed about building her community and more. If you are interested in community building or following your passion, this episode is for you.Learn more about the NYC Backgammon ClubConnect with David on Instagram

Did you build community in 2024? How are you thinking about it in 2025? In this episode Veronica Kaulinis, the Founder of Vulnerable AF, and I discuss the answer to these questions and more. You will learn about the momentum of hosting good events, the benefits of curation, why more time spent upfront is helpful later on, and so much more. If you are interested in community building, this episode for you!Connect with Veronica on IGConnect with David on IG

Are you looking to work professionally as a community builder? Listen to this episode with Jessica Lowenstein who has been working professionally in the field since 2016. She is currently Head of Community and Events at Hampton, a community for founders and CEOs. She has had numerous other community roles. In this episode, you will learn about how the profession has evolved, what she loves about the work, what she looks for when hiring for community roles, and what Hampton's community team looks like. Excited for you to build and grow your Portfolio Career!Connect with Jess on LinkedIn!Connect with David on LinkedIn!

Are you a community builder looking to build a portfolio career? Listen to this podcast episode with Mallory Contois, the Founder of the Old Girls Club (OGC) and Head of Community at Mercury. In this episode, you will learn how Mallory launched OGC and how she built it to be async-focused and how it was helpful for her to get her current role. Mallory is also passionate about portfolio careers and emphasizes the importance of having a clear investment thesis to guide career decisions and advocates for monetizing passions. Excited for you to build and grow your Portfolio Career!Connect with Mallory on LinkedInConnect with David on LinkedIn

What are you excited about? What are you inspired by? Hearing stories about these two topics.... can be inspiring! For episode 350, I hosted an event and invited people to share these stories. Thank you for being part of my podcasting journey, even if this is just for your first episode. Excited for you to build and grow your Portfolio Career!Connect with David on InstagramLearn more in my newsletter

Yena Kim has built the Menswear Dog brand and business for 10+ years, which is crazy and inspiring to think about. You will learn about how her dog, Bodi, first went viral and then how Yena quickly responded on this fame through partnerships and more. In this episode, you will learn about working on things you love, making it easier to work with press, how the creator economy is growing, why online marketing on your own is becoming increasingly important. Unfortunately, Bodi passed away a few days before this podcast recording and Yena talks a little bit about this. This was a special and powerful episode and I hope you enjoy it!Learn more about Meanswear Dog on IGConnect with David on IG

Are you looking to build community? Jaclyn Pascocello is the Founder of Fabrik, a home for community builders. They currently have a physical space open in Tribeca for community builders to host gatherings. I am a member and have hosted a few events there. In this episode, we talk about launching Fabrik, event insights for community builders, and so much more!Connect with Jaclyn on LinkedInConnect with David on LinkedIn

Are you looking to live a life with relationships and friendships at the center of it? In this episode, my good friend Lani Assaf and I walked and talked about our lives and how we are both living like this. We also talked about the challenges and joys of maintaining friendships, the impact of working remotely, and the need for spontaneity and intentionality. Lani emphasized the value of containers for freedom, joy, and play, while I highlighted the significance of repeated interactions and shared experiences. We both reflect on the changing seasons and their impact on their lives, and what else has been on our minds living in Brooklyn. Hope you enjoy it!Connect with Lani on InstagramConnect with me on Instagram

Are you looking to build or grow a community? Listen to these 5 hot takes from community builders. These mini-clips were recorded at my Community Builders and Creators mini conference aka C3 in November. If you are interested in community building, this episode is for you!Connect with me on InstagramLearn more in my newsletter

In this episode, you will hear stories of when people were scared and afraid of something. Through inspiring stories, actionable tips, and a few laughs along the way, we'll show you how to be scared and brave —at the same time. Whether you're facing a career pivot, a big life decision, or just a new personal challenge, this episode will give you the tools to push past your fear and go for it anyways.Connect with David on InstagramRead David's newsletter

What does it mean to truly feel alive? In this episode, we dive into the moments, choices, and emotions that awakened a deeper sense of vitality. Whether it's connecting with people, connecting with music, or a general sense of safety, we discussed stories when people felt alive. Tune in, and let's discover together what makes us feel most alive.Connect with David on InstagramRead David's Substack

In this episode, you will hear the origin story of a community, my Hot Pods, a business, and much more. You will hear about these key moments, what we learned from them, and how things are going now. Tune in to hear stories of creativity, inspiration and passion from those who dared to take the first step. If you've ever wondered how great things begin, this is the episode for you!Connect with David on InstagramRead David's Substack newsletter

Being a community builder is hard. You may want to grow your community but also want to do it thoughtfully. You may want to scale its intimacy but not if it is going to hurt the quality of the community. And then there are business model considerations and challenges. In this Podcast Mixer episode, 10 or so community builders discussed these kind of challenges. If you are a community builder or want to be, this episode may definitely be for you! Connect with David on InstagramRead David's Substack 

What is something that has changed you? In this episode, you will hear short stories and discussion on this topic. You will learn how projects, relationships, cities and more changed people. You never know what the next thing will be that changes you. Listen and enjoy this episode!Connect with David on Instagram

What is something that you have overcome? In this episode, you will hear short stories from people about overcoming something in their lives. Hopefully it helps you realize that whatever you are going through today that it can get better. For me, it was overcoming shyness. I am not shy anymore and this has greatly improved my life. Listen to hear amazing stories!

Should you live with your friends? What happen can happen when you live with people for 3 years? Rina, Juvoni, and I have lived together for three years. We have learned a lot about each other. Juvoni and I didn't initially know Rina, but now she is a close friend. We got together for a chat before Rina moved out. If you want to learn more about us, roommate dynamics, about being a better roomate, this episode is for you! Connect with David here!

Are you looking to slow down to speed up? Steve Schlafman is the Founder of Downshift, a coaching company helping high-performers downshift towards a new life. They offer the world's first decelerator program. Steve has been on the podcast twice before, and in this episode, we also discussed the current state of my podcast in an open and vulnerable way. I hope you enjoy getting to learn more about my view on the content of the show and more too. Excited for you to build and grow your Portfolio Career!Connect with Steve on TwitterConnect with David on Instagram

Has someone taken a chance on you or bet on you early? When this happens, it can have a big and/or lasting impact. In this episode, a few friends shared stories about when someone bet on them early, what they learned from it, and more. Today is a good day to thank someone who bet on you, or to take a chance on someone else. Excited for you to build and grow your Portfolio Career!Connect with David on Instagram

Are you looking to find a romantic partner? In this episode, three people talk about what is going on with their dating lives and what kind of person they may be interested in. A common theme was about being intentional about dating. If you want to learn about dating, relationships, and more, this episode is for you!Connect with David on Instagram

Are you looking for a breakthrough? The next one could happen soon. In this podcast episode, you will hear multiple stories from people sharing breakthroughs. You will hear all types of breakthroughs. Excited for you to build and grow your Portfolio Career!Let's connect on Instagram

Are you looking to build a community or grow one? In this episode, you will hear from 3 community founders about how they are building their communities. You will learn from Ben Bradbury about throwing large-scale reading parties and more at Reading Rhythms. You will learn from Rachel Saslaw about growing StoryTell while working full-time. You will learn from Elle Wilson about building a friends of friends dating event community called Met Through Friends. Excited for you to build and grow your Portfolio Career!Connect with David on InstagramRead David's newsletter

In this episode, we dive into the pivotal moments that changed the course of our lives. Whether it's a career breakthrough, a personal revelation, or an unexpected experience, these turning moments can shape who we are and who we become. Listen to this episode where you will hear 7 people's turning moment stories. Excited for you to build and grow your Portfolio Career!Connect with David on InstagramRead David's Portfolio Career Substack newsletter

What has been an inflection moment for you? In this episode, you will hear from three other community builders sharing about the inflection moments for their communities and for them personally. Your next inflection moment could be right around the corner. Excited for you to build and grow your Portfolio Career!Connect with David on InstagramRead David's Portfolio Career Substack

Are you going through a transition? In this episode, you will hear stories about prior transitions and learnings from it. You will also hear stories about how people are currently going through transitions currently. We are regularly changing and evolving, hopefully this episode helps you in whatever you may be going through. Excited for you to build and grow your Portfolio Career!Connect with David on InstagramRead David's Portfolio Career Substack newsletter

Are you trying to build a project, side hustle, or a business? If so, you will likely have to get through the hard part. It could be internal. It could be external. Or both. In this Podcast Mixer episode, you will hear stories, experiences, and advice from founders and creators who have navigated the hard part and more. Excited for you to build and grow your Portfolio Career!Connect with David on InstagramLearn from David's Portfolio Career Substack

This episode was originally aired on the Chief of Staff Podcast, which is a podcast I help produce. In this episode, I chatted with my coworker and General Manager of Chief of Staff Network, Rahul Desai. We talked about our Chief of Staff experiences, how we work together, how we support Chiefs of Staff, tips to get a Chief of Staff role, and so much more. Excited for you to build and grow your Portfolio Career!Learn more about the Chief of Staff Network!

Is it possible to feel love in other ways besides romantically? In this Podcast Mixer episode, you will hear stories about celebrating love in all of its forms. Talking about love with friends is fun too. I recommend it. I hope this episode makes you feel more hopeful too. Excited for you to build and grow your Portfolio Career!Connect with David on InstagramSubscribe to the Portfolio Career Substack