Podcasts about episode you will learn

Alexis Ohanian is the Founder @ Seven Seven Six, his new fund which just recently announced their first investment leading the $4M seed round for Dispo. Prior to founding Seven Seven Six, Alexis was the Co-Founder & Managing Partner @ Initialized Capital, where he backed many a unicorn including Ro, Flexport, Patreon, GOAT just to name a few. Alexis is also the co-founder @ Reddit, commonly referred to as the front page of the internet, their latest valuation priced the company at $3Bn. In Today’s Episode You Will Learn: 1.) When Alexis left his L Sats to go get waffles, what did he learn about himself? How did that lead to founding Reddit? How did Reddit lead to angel investing? How did that lead to Initialized? 2.) Why did Alexis leave Initialized? Why was now the right time? What worked with Initialized that he has taken with him to Seven Seven Six? What did not work with Initialized that he has learned from? How does he view VC NPS as a result of this and the learnings? 3.) How does Alexis analyse his own relationship to money today? How did his relationship with his mother and her illness impact how he thinks about wealth and happiness? How did he feel when at 22 he sold Reddit? How does he feel about the "keeping up with the Jones'" mentality? 4.) How did having Olympia change how Alexis operates and invests today? How does Alexis define backing projects he would be proud to talk to Olympia about? How does he feel about the type of deals many investors make today? 5.) How did Alexis first meet PG from YC? How did he feel when he heard he believed in him and Steve with Reddit? How did that change how Alexis feels about being the first person to really back someone? Item’s Mentioned In Today’s Episode Alexis’ Favourite Book: Superforecasting: The Art and Science of Prediction Alexis’ Most Recent Investment: Dispo As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Stewart Butterfield is the Founder & CEO @ Slack, the leading channel-based messaging platform, used by millions to align their teams, unify their systems and drive their businesses forward. Prior to their direct listing in June 2019, Stewart raised over $1.3Bn from the likes of Accel, Thrive, Softbank, Kleiner, IVP, T Rowe, GV and a16z to name a few. Prior to founding Slack, Stewart co-founded Flickr, a company he built into one of the largest web services in the world. Due to his many incredible successes, Stewart has been named to the 100 Most Influential People in the World by Time Magazine, and one of the Top 50 Leaders by BusinessWeek. In Today’s Episode You Will Learn: 1.) How Stewart made his way into the world of startups and came to found Flickr? What was his founding moment for the Slack journey? 2.) How does Stewart think about and assess his relationship to money? How has it changed over time? What does Stewart believe are the 3 levels of wealth? How does Stewart think about his identity being tied to the company? Is that a challenge? How does he mitigate it? 3.) How does Stewart describe his management style and philosophy today? How has it changed over time? How does Stewart approach reversible vs irreversible decisions? How does Stewart structure post-mortems? Why does Stewart believe effective entrepreneurship is like parkour? 4.) How does Stewart think about and advise on the debate between direct listing, IPO and SPAC? What has been better/worse and different since making the transition to being a public company? What have been some of the biggest surprises? 5.) Why does Stewart believe that for most companies, comprehension is the reason for the lack of adoption and customer acquisition? How does he look to solve that with Slack? What have been their biggest mistakes on messaging and branding? Item’s Mentioned In Today’s Episode Stewart’s Favourite Book: Leadership and Self-Deception: Getting Out of the Box, Crucial Conversations Tools for Talking When Stakes Are High, The Courage To Be Disliked As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dan Levine is a Partner @ Accel, one of the world's leading venture firms with a portfolio including the likes of Facebook, Slack, Qualtrics, UiPath and Deliveroo. As for Daniel, he actually joined Accel in 2010 before leaving to join Dropbox. At Dropbox, he worked on the platform team helping open the platform to third-party developers and launched and managed many of the company’s developer-facing initiatives. Following Dropbox, he rejoined Accel and has led investments in Scale.ai, Mux, Vercel and Sentry to name a few. In Today’s Episode You Will Learn: 1.) How Dan made his way into the world of venture with Accel? How that led to his joining Dropbox? What led to his re-joining Accel 3 years later? 2.) How does Dan assess the current state of the seed and Series A landscape? How does Dan analyse the rise of pre-emptive rounds? How does Dan determine when to lean in and pre-empt vs when not to? What does Dan think is the biggest myth about raising a Series A? 3.) How does Dan analyse multi-stage funds so actively entering seed? What has Accel's seed portfolio data shown? How many went on to raise a Series A? How many did Accel lead? How many companies died? What is the biggest problem this portfolio presents? 4.) How does Dan analyse the trio of people, product and market? How does Dan approach market sizing? How does Dan approach the risk associated with market timing? What risk is he willing to take? What is he not? When can one stretch on market? When is it a stretch too far? 5.) How does Dan evaluate the rise of solo capitalists? What does he see as the core pros and cons of the model? What are the pros and cons of the partnership model like Accel has? How does Dan evaluate the rise of investor personal brands today? What worries him? Item’s Mentioned In Today’s Episode Dan’s Favourite Book: Titan: The Life of John D. Rockefeller, Sr. (Vintage) Dan’s Most Recent Investment: Altinity As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Zach Weinberg is a Co-Founder of Operator Partners, operators funding operators, with no outside LPs, just their own capital. Fun fact, 20VC Fund has actually invested with them in 3 companies from Alt, Dooly.ai and Boom Pay. Prior to founding Operator Partners, Zach was the Co-founder/COO of Flatiron Health (acq @Roche for $2b) and before Flatiron Zach co-founded Invite Media (acq @Google for $81m). If that was not enough, Zach has also been an incredibly successful angel in the past with a portfolio including RigUp, Ro, Color, BlueApron and Plaid to name a few. In Today’s Episode You Will Learn: 1.) How Zach made his way into the world of startups, came to found Flatiron (acq for $2Bn) and how that led to Operator Partners? 2.) How does Zach analyse his own personal capital allocation? How much in funds? How much in cash, equities, direct, credit etc etc? How does Zach analyse his relationship to money? How has it changed over time? How does Zach evaluate his relationship to risk? 3.) What does Zach make of the rise of pre-empted rounds? When should founders takem them vs reject them? How does Zach feel about multi-stage funds re-entering seed aggressively? How does he advise founders? What are the pros and cons of having multi-stage money? 4.) How does Zach think about the importance of ownership? How does Zach analyse the re-investment decision? How does he approach reserve allocation? How does Zach reflect on his own price sensitivity? How has his relationship to price and ownership changed with time? 5.) How does Zach feel about Brian Armstrong's piece on employees bringing their own political and external beliefs into the workplace? Why does Zach believe that companies are not a democracy? Why does Zach believe that we do not live in a democracy any longer? Item's Mentioned In Today's Episode Zach's Favourite Book: Calling Bullshit: The Art of Skepticism in a Data-Driven World Zach's Most Recent Investment: David Energy As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Helgason is the Founder @ Unity, the company that gives content creators the tools to create innovative RT3D experiences and deliver better processes for almost every industry. Prior to their IPO in 2020, Unity raised from the likes of Sequoia, Thrive, DFJ, SilverLake and then individuals including Max Levchin and VMWare's Diane Greene. If that was not enough, David is currently a Partner @ Nordic Makers, a group of ten top Nordic angels working together to be the best angel investors in the Nordics. David also serves on the board of Labster, Realm.io and Quizup. In Today’s Episode You Will Learn: 1.) How David made his way from founding Unity in a cafe in Denmark to the $10Bn+ public company it is today? 2.) How would David describe his leadership style? How has it changed over time? What were the biggest challenges David faced as the Founding CEO? 3.) What was the decision-making behind David's transition out of the CEO role? What was challenging? What was key to make the transition successful? How did David know John Riccitiello was the right person for the role? How does David advise other founders contemplating the same? 4.) How does David analyse his own board management style? What are the most important elements a board member can do to help the company and founder? What makes Roelof Botha such a special board member to have? How does David advise new board members today to be successful? 5.) Why does David believe running a company is like a liberal art? How does David think about the importance of vision? How does David assess the current state of the European tech landscape? What can be done to improve it? How can investor approach change for the better? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Roleof Botha is a Partner @ Sequoia Capital, one of the world’s leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UiPath, Zoom, the list goes on. As for Roelof, at Sequoia he has led rounds into the likes of YouTube, Instagram, Eventbrite, Square, MongoDB, 23andMe and Unity Technologies to name a few. Before joining the world of venture, Roelof was the CFO @ Paypal playing a key role in their hyper-growth from 2000-2003. In Today’s Episode You Will Learn: 1.) How did Roelof go from actuary in South Africa to CFO @ Paypal? What were his biggest lessons from seeing Paypal burn $10M per month? How did Paypal lead to his joining Sequoia as a Partner? 2.) Market Evaluation: Does Roelof agree that the market is crazy today? How does today compare to prior vintages? How does Roelof assess the compression of fundraising timelines? With compressed timelines, how does he build relationships of trust with founders? 3.) Founder Evaluation: What were Roelof's lessons on founder assessment from Don Valentine? What matrix did Don teach Roelof to assess founders on? How does Roelof feel about the rise of competitive rounds? When should founders take them vs remain heads down on execution? 4.) Investment Mentality: How did Roelof prevent becoming too confident when early investments went well? How does Roelof prevent relying on past failures as a reason for turning down opportunities today? What can investors do to retain a very flexible mind? Why does Roelof believe you are only as good as your next investment? 5.) Sequoia's Edge: How does Roloef think about what it takes for Sequoia to retain it's edge at the top? How does Roloef measure the success of the Sequoia scout program? How did they structure it? How has the structure changed? What do they plan to do moving forward? 6.) Board Membership: How would Roloef evaluate his current style of board membership? How has that style changed over time? What elements did he find challenging? What advice would Roelof give to new board members adopting their first board seats? Items Mentioned In Today’s Show: Roelof’s Favourite Book: Man's Search For Meaning Roelof’s Most Recent Investment: mmhmm As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Eoghan McCabe is a technology entrepreneur. He's started a number of companies, the most notable of which is Intercom, the conversational relationship platform. He was CEO of Intercom for nearly 10 years, during which he grew the company to hundreds of millions in annual revenue, nearly 700 employees, and raised nearly $250M from the likes of Kleiner Perkins, Index, Bessemer, and ICONIQ. He's also invested in dozens of companies including Stripe, Figma, SuperHuman, and Coda. In the summer of 2020 he moved to the role of Chairman of Intercom. In Today’s Episode You Will Learn: 1.) How Eoghan made his way into the world of startups from Ireland and came to build one of the Valley's greats with Intercom? 2.) How does Eoghan thinking about living and thriving with a chip on one's shoulder? What does Eoghan advise in terms of one's search for their true selves? What were his biggest learnings in his search? What does Eoghan advise people who maybe feel they have lost themselves? 3.) Having been CEO of a $Bn company for close to 10 years, how does Eoghan think about dealing with the weight of expectation placed on shoulders? How did he manage it? How does he think about his identity being so tied to his company? 4.) In terms of being one's authentic self, how can one achieve this while also respecting their stakeholders who may hold different views? How does Eoghan think about being an authentic leader vs bowing down to the demands of your team? What is the right balance? 5.) Why does Eoghan think that vision can actually be limiting? How does Eoghan think about stress testing one's vision and ambition? What adversity from early VCs did Eoghan have to fight against? How does Eoghan encourage dissent and debate within his teams? Items Mentioned In Today’s Show: Eoghan’s Fave Book: Breathe: simple breathing techniques for a calmer, happier life As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Cyan Banister is one of the most successful and renowned early-stage investors of the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Today Cyan is a Partner @ Long Journey Ventures, joining the team there following a 4-year stint @ Founders Fund where she led deals in both Niantic and HQ Trivia. Prior to Founders Fund, Cyan was a super successful operator and angel, co-founding Zivity and before that being an early employee at Ironport, leading to their acquisition by Oracle. In Today’s Episode You Will Learn: 1.) How Cyan made her way into the world of startups? How SpaceX came to be her 1st angel investment? How that led to her joining the world of VC? 2.) How does Cyan think about and assess her relationship to money? Why does someone believe she had a fear or loathing of money? What made Cyan the capitalist she is today? How does Cyan analyse her relationship to risk? Has Cyan always trusted her own convictions? 3.) How does Cyan think about her own investment decision-making process? What were Cyan's biggest lessons from her experience with HQ Trivia? How did she change how she interacts with founders pre-investment? Why does Cyan never Google someone before meeting? 4.) How does Cyan think about price sensitivity today? Why does she believe there will be a reckoning? How will this shake out in terms of who succeeds and who fails? Why is Cyan in favour of party rounds? How does she think about VCs with sharp elbows? 5.) Why does Cyan believe SF is eating itself? What can be done to reinvigorate the city positively? What can be done to solve much of the homelessness problem? Why does Chesa Boudin never convict anyone? Why does Cyan believe her "BLM tweet is not spicy"? Why is Cyan fundamentally sad and worried for the current state of the world? Items Mentioned In Today’s Show: Cyan’s Fave Book: Snow Crash As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Spike Lipkin is the Founder & CEO @ Newfront Insurance, the modern insurance brokerage empowering risk management experts with advanced technology to deliver innovative solutions to their clients'. To date, Spike has raised from some of the best in the business including Founders Fund, Meritech and 20VC Fund. Prior to founding Newfront, Spike was one of the first employees at Opendoor, where he helped grow the team from 5 people to an enterprise value of over $5Bn today. Prior to Opendoor, Spike was an investor at Blackstone, where he served on the startup team that built Invitation Homes into the largest owner of single-family real estate in the United States. In Today’s Episode You Will Learn: 1.) How Spike made his way from banking to be one of the first operators at Opendoor to founding the next generation of insurance with Newfront? 2.) What were some of the biggest takeaways for Spike from his time at Opendoor as employee #5? How does Spike approach prioritisation? How does he determine what to delegate vs what to control? 3.) How would Spike describe his own style of leadership? How has Spike needed to change his style with the business? What does Spike believe is his biggest weakness as a leader? What is he doing to confront it and grow as a leader? What is the most important thing a leader can do? 4.) How does Spike think about what it takes to acquire the very best talent? What does his framework for hiring look like? Why did Spike decide to hire a COO? Why was then the right time? How does Spike think about the balance between hiring external vs promoting internal? 5.) Why did Spike believe it was important not to announce any of his prior fundraises? How did Spike approach investor selection with Newfront? Does Spike believe founders should meet with VCs between fundraises? Which angel has done the most to move the needle for the company? How? Items Mentioned In Today’s Show: Spike’s Fave Book: Team of Rivals: The Political Genius of Abraham Lincoln As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

George Zachary is a General Partner @ CRV, one of the nation's oldest and most successful early-stage venture capital firms with a portfolio including the likes of Airtable, DoorDash, Dropbox, Niantic and many more. As for George, today at the firm he focuses on advancing health through revolutionary computer science, centred around bio-engineering. During his incredible 16 year tenure at CRV, he has led deals in the likes of PillPack, Udacity, Scribd and HealthIQ. Before joining CRV, George was a General Partner @ Mohr Davidow Ventures for over 6 years. In Today’s Episode You Will Learn: 1.) How George made his way into the world of venture over 21 years ago and how he came to be a General Partner @ CRV 16 years ago? 2.) How did seeing the booms and busts of the dot com and 08 impacts George's investment mindset? What is the right way to voice concerns in an internal investment discussion? How does George now view capital intensity? How does it impact his conviction and check size? 3.) Why does George believe one should invest in founders who do not need their investors help? Why does George believe the best founders have experienced some form of parental instability? How does George detect the psychological need to win when he meets founders? What are the signs? 4.) How would George describe his own philosophy of board membership? How has it changed over time? What are the 2 control functions that a board member has? What advice does George give to new board members today? Where do many young board members make mistakes? 5.) How does George analyse his own personal relationship to money? How has it changed over the years? How did his relationship to money change his relationship with people? Was that challenging? How did he cope with it? How does he advise others who experience the same? Items Mentioned In Today’s Show: George's Favourite Book: Foundation Trilogy George’s Most Recent Investment: Glympse Bio As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Lawee founded CapitalG, Alphabet’s independent growth fund, in 2013, drawing on his experience both at Google and as a serial entrepreneur. Since then, he has helped transform high-potential startups into some of the most highly valued businesses of our generation, including Airbnb, Lyft, Snap, Robinhood, Credit Karma, Oscar, Lending Club and Thumbtack. Prior to CapitalG, David played a pivotal role in Google’s growth story--first as Google’s Chief Marketing Officer and then as the instrumental VP of corporate development where his group spearheaded over 100 acquisitions for the company. CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How David made his way into the world of startups, came to be the first CMO @ Google and how that led to his founding CapitalG? 2.) Having operated and invested through both the dot com and 08', how has seeing the booms and busts impacted David's investing mindset? How does David think about temporal diversification today with CapitalG? Why does David believe diversification is largely overrated? 3.) How does David think about portfolio construction today, given CapitalG is a growth fund? How does David compare early-stage to growth today? How does David think about loss ratios at growth? How does David benchmark good vs great from a multiple perspective at growth? 4.) How does CapitalG approach investment decision making today? How does David avoid consensus thinking/following the crowd when it comes to deals? Why does David believe investment clubs operate much more successfully than partnerships? How does that change the structure for CapitalG? 5.) How has David seen himself evolve and develop as a board member of the years? What type of board member would David say he is today? How does that change with the founder? Who is the most memorable board member David has sat on a board with? Items Mentioned In Today’s Show: David’s Fave Book: Born A Crime: Stories from a South African Childhood  David’s Most Recent Investment: Albert As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Arlan Hamilton is the Founder and Managing Partner @ Backstage Capital, the seed fund that has paved the way investing exclusively in startups that are led by underrepresented founders. Backstage Capital also expanded their model and now have Backstage Accelerator working with companies across 4 cities. Last month, Mark Cuban gave Arlan $6M to invest in underestimated founders (ArlanWasHere Investments Fund I). Arlan is also an Author of "It's About Damn Time". If you would like to invest with Arlan, you can, check out BackstageCrowd.com with over 2,000 accredited and non-accredited investors, they just completed their 6th deal and $1m raised within 3 months of launch. In Today’s Episode You Will Learn: 1.) How Arlan made her way from the airport floor to founding her own venture firm, Backstage Capital and writing a book, "It's About Damn Time"? 2.) How does Arlan assess her own relationship to money and wealth? What is Arlan's thinking around her desire to give away 90% of her wealth? How does Arlan evaluate her own appetite for risk? How has that changed over time? 3.) From a strategic perspective, what are some core elements to Arlan's strategy that are not obvious? What are the main misconceptions that remain with regards to under-represented founders? What does Arlan believe are the leading indicators when assessing founders today? 4.) What does Arlan believe have been the biggest challenges in building the firm that is Backstage? What have been the core breaking points in the scaling of people and strategy? How does Arlan think about the relationship between brand vs reputation? What does Arlan believe are the main misconceptions people have about her? 5.) How would Arlan like to see the world of venture change over the next decade? What can LPs do to encourage more under-represented founders are backed? How can this be measured? Who should be held accountable? Items Mentioned In Today’s Show: Arlan’s Fave Book: What I Know For Sure by Oprah Winfrey As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Palmer Luckey is the Founder @ Anduril Industries, founded on the premise of radically transforming the defence capabilities of the United States and its allies by fusing artificial intelligence with the latest hardware advancements. To date, Palmer has raised over $385M with Anduril from Founders Fund, a16z, Elad Gil, Spark Capital, Lux Capital, General Catalyst and 8VC to name a few. Prior to changing the world of defence, Palmer founded Oculus VR where he designed the Oculus Rift. Oculus VR was acquired by Facebook for $2.3Bn in 2014. In Today’s Episode You Will Learn: 1.) How Palmer made his way into the world of startups, made his way from trailer to selling Oculus for $2.3Bn to changing the defence industry with Anduril today? 2.) How does Palmer evaluate his own relationship to money? How has that changed since his $2.3Bn Oculus exit? How does Palmer assess his relationship to risk? How does Palmer approach the correlations between money, risk and happiness? 3.) What were some of Palmer's biggest takeaways from his time scaling Oculus? How have they informed his mindset with Anduril? What worked? What did not work? How has Palmer changed as a leader? How does Palmer approach personal development? How does he optimise for it? 4.) Palmer scaled Oculus to 1,400 people in 1 year, where do organisations break with scale? Why does Palmer believe, "you never want to play yourself"? Where does he feel his biggest weakness is as a scaling leader? How does Palmer approach hiring at scale yet maintaining culture? 5.) From a defence standpoint, why does Palmer feel the US needs to be more like the Chinese? Why is the DoD so poor at investing in innovation? What does it take to sell into the DoD really effectively? Why have the only 2 successful defence companies been founded by billionaires? Items Mentioned In Today’s Show: Palmer’s Fave Book: The Three-Body Problem As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Shishir Mehrotra is the Founder & CEO @ Coda, the startup that brings all of your words and data into a flexible all-in-one doc. To date, Shishir has raised over $140M from some great names including Greylock, Kleiner Perkins, General Catalyst, NEA and Homebrew to name a few. Prior to founding Coda, Shishir spent an incredible 6 years at Google in a couple of different roles; first as Director of Product for Youtube Monetisation and then moving to Youtube VP of Engineering, Product and UX. Before Google, Shishir was with Microsoft for 6 years as a Director of Program Management. Shishir also serves on the board of Spotify. In Today’s Episode You Will Learn: 1.) How Shishir made his way into the world of tech, came to be VP of Engineering, Product and UX @ Youtube and how it led to founding Coda? 2.) What is the No 1 quality of a good decision? How does Shishir think through reversible vs irreversible decisions? What are the 4 phases of decision-making? When should decisions be based on speed vs not? How can teams adjust questions to come to more productive outcomes? 3.) How does Shishir encourage debate and dissent within team discussions? How can leaders build deep trust with their teams? How can leaders create true democracy for idea sharing and meritocracy? Should ideas always be acted on immediately? What are the pros and cons? 4.) How does Shishir think about and evaluate his own operating cadence? How has this changed over time? How does Shishir approach time allocation? What have been his core learnings? How does Shishir divide his time between proactive and reactive tasks? 5.) How does Shishir approach OKR setting? What can leaders do to create aspirational and inspirational goals? How should goals be correctly communicated across orgs? How many OKRs should one team/person have? How should attribution across OKRs be given? Items Mentioned In Today’s Show: Shishir’s Fave Book: Switch: How to change things when change is hard  As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Pall and Drew Taggart are the Founders of The Chainsmokers and Mantis. The Chainsmokers are one of the most sought after musical acts of our time. As for Mantis, just last week they announced their first $35M venture fund and have backing from Ron Conway, Mark Cuban and Keith Rabois. They have already invested in hotly contested rounds for Fiton and Loansnap. Drew and Alex also own a production studio, are stakeholders in the spirit brand JaJa Tequila and last year co-founded the anti-scalper ticketing platform Yellowheart. In Today’s Episode You Will Learn: 1.) How Drew and Alex made their way into the world of tech and startups and how they came to found a venture firm with Mantis? 2.) Why did Alex and Drew decide now was the right time for the fund? What did they look for in their LPs? How do they use their LPs to strategically help their companies? What is their preferred stage, sector? Do they have ownership requirements? 3.) Are Alex and Drew nervous about making the move into venture? If everyone has a chip on their shoulder, where does the chip on their shoulder come from? How do they think about their own vulnerabilities? How do they manage them? What works? What does not? 4.) What ways do Alex and Drew most like to work with their founders? Where do they provide outsized value? What are some examples of this? How do they think about working with VCs to get into the best rounds? How do they want to position Mantis in the ecosystem? 5.) With the tequila brand, the film production company and now the venture fund, how do they think about the expansion of "The Chainsmokers Empire"? What does this look like in 10 years? How would they like it to expand and grow? Items Mentioned In Todays Episode Drew's Favourite Book: The Unbearable Lightness of Being As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Podcast Notes Key Takeaways The reason Lambda School is so successful is that they cover the downside for their students: Students don’t have to pay anything until they get a job “If it doesn’t work out, you don’t pay anything” – Austen AllredWhen you raise a round of capital, chances are you’re also letting that investor join your board“It is a marriage” – Austen AllredHiring a Chief Operating Officer requires customization, you can’t just hire one off the shelf. You want the COO’s strengths to be the founder’s weaknesses and vice versa.“It’s a really symbiotic relationship” – Austen AllredSilicon Valley was like Florence during the Renaissance except for techAusten believes that because so many people are moving out of San Francisco, you no longer have to go there to network and build a great company. The next tech city will be in the cloud.“I definitely think we won’t ever really go back to 2019 Silicon Valley” – Austen AllredRead the full notes @ podcastnotes.org Austen Allred is the Founder & CEO @ Lambda School, the startup that remotely trains people to become a web developer or data scientist and the students pay no tuition until they are hired. Just last month, Lambda's $74M Series C was announced led by Gigafund bringing their total funding to date to over $129M with prior investors including Stripe, Bedrock, GV, Gigafund and GGV to name a few. Prior to founding Lambda, Austen was Senior Manager for Growth @ LendUp and before that co-founded Grasswire. In Today’s Episode You Will Learn: 1.) How Austen made his way into startups having slept in a Honda Civic and how he went from homeless to rockstar founder @ Lambda? 2.) How does Austen evaluate his own attitude to risk? How does Austen think about downside protection today? How has this changed over time? How does Austen feel about founders taking secondaries? How does Austen think about his own relationship to money? 3.) Having raised his Series C last month, why did Austen choose the investors he did? How did the round progress? What made Gigafund different to alternate options? What makes the best board members in Austen's mind? What makes the worst? 4.) What have been the most challenging elements for Austen of scaling the team? How does complexity change with time in team scaling? Why did Austen bring in a COO? What did he look for in the role? How does Austen advise others on bringing in a COO? 5.) Why does Austen believe that post-COVID we will never go back to the valley as we knew it? Why does Austen believe the valley represents the biggest potential squandering of wealth in history? How does Austen evaluate the government intervention we have seen? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Austen Allred is the Founder & CEO @ Lambda School, the startup that remotely trains people to become a web developer or data scientist and the students pay no tuition until they are hired. Just last month, Lambda's $74M Series C was announced led by Gigafund bringing their total funding to date to over $129M with prior investors including Stripe, Bedrock, GV, Gigafund and GGV to name a few. Prior to founding Lambda, Austen was Senior Manager for Growth @ LendUp and before that co-founded Grasswire. In Today’s Episode You Will Learn: 1.) How Austen made his way into startups having slept in a Honda Civic and how he went from homeless to rockstar founder @ Lambda? 2.) How does Austen evaluate his own attitude to risk? How does Austen think about downside protection today? How has this changed over time? How does Austen feel about founders taking secondaries? How does Austen think about his own relationship to money? 3.) Having raised his Series C last month, why did Austen choose the investors he did? How did the round progress? What made Gigafund different to alternate options? What makes the best board members in Austen's mind? What makes the worst? 4.) What have been the most challenging elements for Austen of scaling the team? How does complexity change with time in team scaling? Why did Austen bring in a COO? What did he look for in the role? How does Austen advise others on bringing in a COO? 5.) Why does Austen believe that post-COVID we will never go back to the valley as we knew it? Why does Austen believe the valley represents the biggest potential squandering of wealth in history? How does Austen evaluate the government intervention we have seen? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ravi Gupta is a Partner @ Sequoia Capital, one of the world's leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UiPath, Zoom, the list goes on. As for Ravi, prior to Sequoia, he spent 4 years as COO & CFO @ Instacart playing an integral role in their hyper-growth journey. Before that Ravi spent 10 years as a Director @ KKR. In Today’s Episode You Will Learn: 1.) How Ravi made his way from KKR to being one of the key execs leading Instacart? How Instacart led to Ravi becoming a Partner @ Sequoia? 2.) When thinking about team, what does Ravi believe is the single most important question to ask? How does Ravi determine between good and great when assessing talent? What are the leading indicators? What have been Ravi's lessons on what it takes to acquire those great talents? 3.) How does Ravi think about and approach prioritisation today? How does Ravi analyse what to delegate vs what to control? Should you get good at your weaknesses and double down on strengths? How does Ravi think about vulnerability within leadership? How did he show that vulnerability as a leader at Instacart? 4.) In joining Sequoia, what has Ravi been most impressed with in regards to the team? What has he been most surprised by? Why is Ravi so bullish unanimous decision-making is right? How do founders determine which Sequoia Partner will be on their board? 5.) How does Ravi think about what it takes to be the very best board member? Who is the best board member Ravi has worked with? What made them so special? What advice does Ravi give to new board members adopting board seats for the first time? Items Mentioned In Today’s Show: Ravi’s Fave Book: Clay Christensen: How Will You Measure Your Life? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Tew is the Co-Founder and Co-CEO @ Calm, the #1 App for Meditation and Sleep allowing you to find your calm, sleep more, stress less and live better. To date, the company has raised over $143M in funding from some of the best including Lightspeed, Insight, TPG and then some very cool names such as Ashton Kutcher, Harry Styles, Brad Feld and Jason Calacanis. Prior to Calm Alex founded numerous other startups including PopJam, Pixelotto and most famously rose to internet fame with his founding of The Million Dollar Homepage. In Today’s Episode You Will Learn: 1.) How Alex went from playing Fifa with Michael Acton Smith in Berwick St, London to founding one of the hottest startups in the valley, Calm? 2.) What does Alex believe the very best brands do today? How do they message? How do they present? How do they divide opinion? How did Alex think about the early Calm brand? How has it changed? How does Alex advise others looking to build a company brand? 3.) Does Alex agree with Peter Fenton, "there is a lack of free and open distribution"? How does Alex analyse the economics for customer acquisition costs today? What is a good paid vs organic ratio? How do CACS change over time in Alex's experience? 4.) What have been Alex's biggest learnings on what it takes to build a viral product? Where do many people go wrong? Why does Alex believe pressure is the enemy of creativity? Does Alex believe people should create time for creative thought? What does Alex do to stimulate idea creation? 5.) How has Alex seen himself evolve and develop as a leader over the last 5 years? What have been the hardest elements to scale? How does Alex think about effective delegation? What have been Alex's biggest lessons on what it takes to hire A* people consistently? Items Mentioned In Today’s Show: Alex’s Fave Book: Godel, Escher, Bach: An Eternal Golden Braid As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Podcast Notes Key Takeaways “We see this SPAC phenomenon not as a flash in the pan, not as a quick up and down…but really an enduring vehicle to bring our innovation companies to market and we find that to be extremely exciting”– Troy Steckenrider What is a SPAC?A SPAC is a pool of capital that is used to invest in a private company and help them go public. The capital is raised on the public markets through a traditional IPO and goes into a bank where it is held for up to two years. During that 2-year time, the SPAC management team has an opportunity to go find a partner company, negotiate a deal with them, and take them public. What are the benefits of a SPAC?From the private company’s perspective, it’s an easier path to get into the public marketsFrom the SPAC’s perspective, it’s a way to invest in a company before it IPOs“A company with a strong management team with a clear competitive advantage in an unusual market will always find great investors and draw those great investors” – Kevin HartzRead the full notes @ podcastnotes.org Kevin Hartz is Co-Founder & Partner @ A*, a newly listed special acquisition company which raised $200M to acquire and take public a tech startup. Kevin is also the Co-Founder, former CEO, and Chairman Eventbrite (NYSE: EB). Before Eventbrite, Kevin was the Co-Founder & former CEO of online money transfer service, Xoom (acquired by PayPal for $1.1B). Kevin is also one of the most successful early-stage investors in the business with a portfolio including the likes of Airbnb (Seed, Series A), Uber (Series B), Pinterest (Seed, Series A), Trulia (first check) and PayPal (Seed). Troy Steckenrider is Kevin's co-founder and Partner @ A*. Prior to A*, Troy was COO @ ZeroDown changing the landscape for homeownership with $136M in funding. Before ZeroDown, Troy spent 5 years at Opendoor as Director of Capital Markets. Before that hyper-growth experience at Opendoor, Troy enjoyed roles at both Bain Private Equity and McKinsey. In Today’s Episode You Will Learn: 1.) How Troy and Kevin came together to co-found A*? What is a SPAC? What are Kevin and Troy looking to achieve with the SPAC? 2.) What does Kevin believe are the primary drivers for the rise in SPAC's over the last few years? How will they change the structure of both the VC and startup industry? How will the SPAC landscape evolve over the next few years? What is the biggest challenge they face? 3.) Why does Kevin believe that the fee structure for SPACs is egregious? How would they like to change the incentive structure? How does the timeline for a SPAC transaction compare to that of an IPO? How does the fee structure compare when comparing SPACs to banks in IPOs? 4.) Why did Kevin and Troy choose $200M for the right size for their first SPAC? How does the size of the SPAC determine the type of company the SPAC will merge with? What are Kevin and Troy looking for in their partner company? 5.) What does the fundraising process look like for a SPAC? How do SPAC sponsors deal with the challenge that LPs call pull out if they do not like the proposed partner deal? When evaluating SPACs, what do investors look to invest because of? What makes A* special? Items Mentioned In Today’s Show: Troy’s Fave Book: Churchill: Walking with Destiny As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Podcast Notes Key Takeaways “We see this SPAC phenomenon not as a flash in the pan, not as a quick up and down…but really an enduring vehicle to bring our innovation companies to market and we find that to be extremely exciting”– Troy Steckenrider What is a SPAC?A SPAC is a pool of capital that is used to invest in a private company and help them go public. The capital is raised on the public markets through a traditional IPO and goes into a bank where it is held for up to two years. During that 2-year time, the SPAC management team has an opportunity to go find a partner company, negotiate a deal with them, and take them public. What are the benefits of a SPAC?From the private company’s perspective, it’s an easier path to get into the public marketsFrom the SPAC’s perspective, it’s a way to invest in a company before it IPOs“A company with a strong management team with a clear competitive advantage in an unusual market will always find great investors and draw those great investors” – Kevin HartzRead the full notes @ podcastnotes.org Kevin Hartz is Co-Founder & Partner @ A*, a newly listed special acquisition company which raised $200M to acquire and take public a tech startup. Kevin is also the Co-Founder, former CEO, and Chairman Eventbrite (NYSE: EB). Before Eventbrite, Kevin was the Co-Founder & former CEO of online money transfer service, Xoom (acquired by PayPal for $1.1B). Kevin is also one of the most successful early-stage investors in the business with a portfolio including the likes of Airbnb (Seed, Series A), Uber (Series B), Pinterest (Seed, Series A), Trulia (first check) and PayPal (Seed). Troy Steckenrider is Kevin's co-founder and Partner @ A*. Prior to A*, Troy was COO @ ZeroDown changing the landscape for homeownership with $136M in funding. Before ZeroDown, Troy spent 5 years at Opendoor as Director of Capital Markets. Before that hyper-growth experience at Opendoor, Troy enjoyed roles at both Bain Private Equity and McKinsey. In Today’s Episode You Will Learn: 1.) How Troy and Kevin came together to co-found A*? What is a SPAC? What are Kevin and Troy looking to achieve with the SPAC? 2.) What does Kevin believe are the primary drivers for the rise in SPAC's over the last few years? How will they change the structure of both the VC and startup industry? How will the SPAC landscape evolve over the next few years? What is the biggest challenge they face? 3.) Why does Kevin believe that the fee structure for SPACs is egregious? How would they like to change the incentive structure? How does the timeline for a SPAC transaction compare to that of an IPO? How does the fee structure compare when comparing SPACs to banks in IPOs? 4.) Why did Kevin and Troy choose $200M for the right size for their first SPAC? How does the size of the SPAC determine the type of company the SPAC will merge with? What are Kevin and Troy looking for in their partner company? 5.) What does the fundraising process look like for a SPAC? How do SPAC sponsors deal with the challenge that LPs call pull out if they do not like the proposed partner deal? When evaluating SPACs, what do investors look to invest because of? What makes A* special? Items Mentioned In Today’s Show: Troy’s Fave Book: Churchill: Walking with Destiny As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Kevin Hartz is Co-Founder & Partner @ A*, a newly listed special acquisition company which raised $200M to acquire and take public a tech startup. Kevin is also the Co-Founder, former CEO, and Chairman Eventbrite (NYSE: EB). Before Eventbrite, Kevin was the Co-Founder & former CEO of online money transfer service, Xoom (acquired by PayPal for $1.1B). Kevin is also one of the most successful early-stage investors in the business with a portfolio including the likes of Airbnb (Seed, Series A), Uber (Series B), Pinterest (Seed, Series A), Trulia (first check) and PayPal (Seed). Troy Steckenrider is Kevin's co-founder and Partner @ A*. Prior to A*, Troy was COO @ ZeroDown changing the landscape for homeownership with $136M in funding. Before ZeroDown, Troy spent 5 years at Opendoor as Director of Capital Markets. Before that hyper-growth experience at Opendoor, Troy enjoyed roles at both Bain Private Equity and McKinsey. In Today’s Episode You Will Learn: 1.) How Troy and Kevin came together to co-found A*? What is a SPAC? What are Kevin and Troy looking to achieve with the SPAC? 2.) What does Kevin believe are the primary drivers for the rise in SPAC's over the last few years? How will they change the structure of both the VC and startup industry? How will the SPAC landscape evolve over the next few years? What is the biggest challenge they face? 3.) Why does Kevin believe that the fee structure for SPACs is egregious? How would they like to change the incentive structure? How does the timeline for a SPAC transaction compare to that of an IPO? How does the fee structure compare when comparing SPACs to banks in IPOs? 4.) Why did Kevin and Troy choose $200M for the right size for their first SPAC? How does the size of the SPAC determine the type of company the SPAC will merge with? What are Kevin and Troy looking for in their partner company? 5.) What does the fundraising process look like for a SPAC? How do SPAC sponsors deal with the challenge that LPs call pull out if they do not like the proposed partner deal? When evaluating SPACs, what do investors look to invest because of? What makes A* special? Items Mentioned In Today’s Show: Troy’s Fave Book: Churchill: Walking with Destiny As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jennifer Tejada is the CEO @ PagerDuty, the company that provides a real-time operations platform ensuring less downtime for your digital services. Prior to their IPO in 2019 PagerDuty raised funding from some of the best in the business including Accel, a16z, Baseline, Bessemer and Harrison Metal to name a few. As for Jennifer, prior to PagerDuty, she was CEO of Keynote Systems leading to their acquisition by Dynatrace. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at Mincom, leading them to their acquisition by ABB. If that was not enough, Jennifer is also on the The Estée Lauder Companies Inc. (NYSE: EL). CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Jennifer made her way into the world of SaaS and came to be one of the leading enterprise CEOs today with PagerDuty? How does Jen advise graduates on joining a startup vs large incumbent? 2.) How does Jen analyse and evaluate her relationship to risk? What does Jen do to remove herself from her environment and make the clearest decisions? How has Jen's decision-making process changed? How does Jen encourage debate and free thought sharing internally? 3.) How does Jen think about the role of insecurity within leadership? What would Jen say are her biggest insecurities? How does Jen manage them and mitigate them today? What works? What does not? Why does Jen believe data is the key to overcoming insecurities? 4.) What have been Jen's biggest lessons on what successful board management looks like? What separates good vs great board members? How can CEO's structure their board in an optimal way? What do they need? What do they not need? How does scale change this? 5.) How does Jen think her style of leadership has changed over the years? What have been Jen's lessons on what it takes to both acquire and retain the very best execs? Where do many go wrong here? Items Mentioned In Today’s Show: Jennifer’s Fave Book: Tuesdays With Morrie: An old man, a young man, and life's greatest lesson As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sahil Lavingia is the Founder and CEO @ Gumroad, the company that helps creators do more of what they love. With Gumroad, Sahil has raised funding from an all-star list of investors including Accel, Kleiner Perkins, First Round and then Max Levchin, Chris Sacca, Ron Conway and Naval Ravikant on the individual side. However, most recently Sahil has made waves launching one of the first rolling funds on AngelList with his being $6M per year. In the past, Sahil has backed the likes of Lambda School, Figma, HelloSign and Haus to name a few. In Today’s Episode You Will Learn: 1.) How did Sahil make his way into the world of startups and angel investing? What were his biggest takeaways from being employee #2 at Pinterest? How did that experience impact his mindset? 2.) Why did Sahil decide to make his new fund an AngelList rolling fund? How is it structured? Does Sahil think this will represent a seismic shift in early stage investing? Is this a game of the 1%? Why does Sahil think early-stage remains so undervalued? How will this impact Series A pricing? 3.) How does Sahil assess his own price sensitivity today? How does Sahil think about the right way to turn down a founder? Where do many go wrong? How does Sahil feel about the rise of pre-empted rounds? How does Sahil advise seed founders with offers from multi-stage firms? 4.) What does Sahil believe founders care most about today in their investors base? How does Sahil think about investor brand and distribution? How does Sahil analyse the pros and cons of party rounds? How does Sahil advise founders on constructing their early cap table? 5.) How does Sahil think about his relationship to risk and to money? How did Sahil deal with it when his investors wrote off his company? How did Sahil feel about the weight of expectation placed on his shoulders at such a young age? How did he deal with this? Items Mentioned In Today’s Show: Sahil’s Fave Book: How to Win Friends and Influence People As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ben Rubin is the Founder & CEO @ /talk, the anti-meeting tool for fast, decentralised conversations. Prior to co-founding /talk, Ben was the Co-Founder & CEO @ Houseparty, where he scaled the product to millions of users and raised over $70M in funding from the likes of Sequoia, Greylock and Entree Capital to name a few. In addition over the last few years Ben has enjoyed roles at Sequoia as a Scout and then also at Benchmark as an Entrepreneur-In-Residence. In Today’s Episode You Will Learn: 1.) How Ben made his way into the world of startups and came to found Life on Air, later turning into Meerkat and Houseparty? 2.) What were Ben's key learnings from the Houseparty scaling experience? Why are the traditional metrics we use to measure startup success (DAU, MAU etc) insufficient? What is the nuance to metrics? How does Ben think about being first to market vs being the best to market? 3.) How does Ben believe the product principles differ when comparing the 0-1 stage vs 10-100 stage? How does Ben think about where to be rigorous on product? How does Ben advise founders to discover the key guiding product principle? What was it for Ben with Meerkat? 4.) Meerkat pivoted to Houseparty 3 months after having raised $40M, how did Ben communicate that to the board? How did they respond? How does Ben believe the best boards operate? What does Ben most look for in his board members? Where do many go wrong with board management? 5.) From the team side, when in hypergrowth, when do things start to break? What profiles are usually the first to break? Does that mean one should not hire those profiles? What can the leader do to create that intimacy and trust amongst the team? Items Mentioned In Today’s Show: Ben’s Fave Book: Seneca: The Shortness of Life As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Apurva Mehta is the Managing Partner @ Summit Peak Investments, investing in early stage venture capital funds and making direct co-investments. To date they have backed the likes of Raymond Tonsing, Lachy Groom and Josh Buckley to name a few on the fund side and then on the direct side, invested in Airtable, Virta Health and Sourcegraph. Prior to founding Summit Peak, Apurva spent 7 years as the Deputy Chief Investment Officer at Cook's Children's Hospital and before that spent 3 years as Director of Portfolio Investments at The Juilliard School. In Today’s Episode You Will Learn: 1.) How did Apurva make his way into the world of fund investing? How did that lead to his founding Summit Peak and also becoming a GP? 2.) How does Apurva think about how much importance to place on references when diligencing managers? What reference types mean a lot? Which mean less? Why does Apurva still believe early-stage is the most inefficient segment of the venture landscape? 3.) How does Apurva think about GP commits? Is it fair to have a required benchmark? How does Apurva advise founders on LP concentration limits? When is one LP too much of a fund? How does Apurva advise managers on selling a stake in the management company? 4.) As a fund of funds, how does Apurva approach fund portfolio construction today? How does this differ between the fund portfolio vs the direct portfolio? How does Apurva think about the compression of fundraising timelines both with GPs and Founders? Why does Apurva believe founders at the early-stage care less about firm brand today? 5.) How does Apurva feel about investing in managers he has not met in person? How does the GP/LP fundraising process need to change? How does COVID change the fundraising process for venture funds? How will LPs react to these changes? Items Mentioned In Today’s Show: Apurva’s Fave Book: Principles: Life and Work by Ray Dalio Apurva's Most Recent Investment: Sourcegraph As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Anna Khan is a General Partner @ CRV, one of the pre-eminent firms of Silicon Valley stretching over what is now an incredible 18 funds. In their portfolio, they have the likes of Airtable, Doordash, Postman and PillPack to name a few. As for Anna, prior to joining CRV, she spent an incredible 6 years at Bessemer investing in the likes of Intercom, NewVoiceMedia, RainforestQA and Zylo. If that was not enough, Anna is also the Founder & CEO @ Launch X Ventures, offering female entrepreneurs an immersive opportunity to learn how to raise capital for their businesses. In Today’s Episode You Will Learn: 1.) How Anna made her way into venture as an analyst with Bessemer and how that led to her scaling the venture ladder to now being GP @ CRV? 2.) How does Anna feel about the importance of analysts in venture? Should founders spend meaningful time with analysts? How should they determine which to spend time with? What were the biggest lessons Anna learned about venture and people from being an analyst at Bessemer? 3.) With the rise of rounds being pre-empted, how does Anna determine when to lean in and move on a deal vs when to wait? How does Anna determine when to stretch vs be disciplined on valuation? Why does Anna believe very few firms are "doing real early-stage investing" today? 4.) Why does Anna believe that there are so much fewer women in venture? How does Anna respond to the suggestion that it is a "pipeline problem"? How would Anna advise an all-white male partnership looking to truly change how they work? How does carry come into showing commitment? 5.) What advice does Anna give to people on developing your early network? Why does Anna believe VCs spending time with VCs is antithetical? How has Anna's investment decision-making process changed over the last 9 years? How does Bessemer's compare to CRV's? Items Mentioned In Today’s Show: Anna’s Fave Book: Why We Sleep: The New Science of Sleep and Dreams As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Dev Ittycheria is the President and CEO @ MongoDB, recognized as the world's most popular next-generation database and the first database company to go public in over 26 years. Prior to their IPO, MongoDB raised from some of the best in the business including Sequoia, USV and NEA to name a few. As for Dev, before Mongo Dev was Managing Director at OpenView Venture Partners, Venture Partner at Greylock Partners, and CEO/Co-founder of BladeLogic, which was acquired by BMC for $900 million. Dev has also sat on some incredible boards including AppDynamics, athenahealth and BazaarVoice. In Today’s Episode You Will Learn: 1.) How Dev made his way into the world of startups? How Dev made his entry into the world of venture? How that led to his joining Mongo as CEO? 2.) How has Dev seen his style of leadership change over the last few years? What are the 3 core benefits of being vulnerable with your investors? Why does Dev believe you sometimes have to be inefficient to be effective? What element/trait would Dev like to improve and develop as a leader? 3.) Where does Dev believe the majority of leaders make mistakes when it comes to scaling their teams and orgs? How does Dev think about the debate of whether to promote internally or hire externally for a role? Why does Dev believe the asymmetry of information there is dangerous? 4.) What has been Dev's biggest lessons when it comes to the speed that information is relayed within orgs? How does this differ between good news and bad news? What can leaders do to create environments where bad news is shared freely? Where do many go wrong here? 5.) How does Dev advise founders on the criteria they should use to determine which investors to work with? What has been so impressive to Dev about working with Sequoia? How would Dev describe Roelof Botha's style of board membership? How can investors crucially build trust with their CEOs? Items Mentioned In Today’s Show: Dev’s Fave Book: High Output Management As always you can follow Harry and The Twenty Minute VC on Twitter here!

Joe Thomas is the Founder & CEO @ Loom, the startup that helps you get your message across by making it easy to record instantly shareable videos. To date, Joe has raised over $68M from some of the valley's leading firms including Sequoia, Kleiner and Coatue as well as individuals such as Mathilde @ Front, Kevin & Mike @ Instagram and Dylan Field @ Figma to name a few. Prior to founding Loom, Joe was in LA as Director of Product at MyLife.com and before that Director of Operations at MediaPass. Due to Loom's success, Joe has been named to Forbes 30 Under 30 for Enterprise Tech. In Today’s Episode You Will Learn: 1.) How Joe made his way from the mid-West to the valley and came to found one of the hottest startups today in Loom? 2.) What does Joe believe are 3 rules to operate remote teams successfully? Why does Joe believe in remote + HQ as a model so much? How do the tools and culture need to change with this as a new format for work? How do leaders now need to learn to write more than ever before? 3.) How has fundraising fundamentally change in the world of COVID? What are the benefits? What can founders do and tools can they use to increase their chances of getting funded in a COVID world? What did Coatue do to build rapport and trust without meeting in person? 4.) What advice would Joe give to founders on how to pick their early VCs? How does Joe advise founders when it comes to accepting multi-stage money at seed? Why does Joe believe you need to be upfront with your VCs about their ability to build future ownership? 5.) Sequoia and Coatue led the Series B, how did the round go down many months before Joe and Loom planned to raise it? What did Sequoia do to win and close the deal? How did that as a founder make Joe feel? How does Joe advise VCs on what it takes to win the most competitive of deals? Items Mentioned In Today’s Show: Joe’s Fave Book: Enders Game, Think On These Things As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Steve Jurvetson is the Co-Founder @ Future Ventures who announced their debut and flagship $200M Fund in 2019. Steve's incredible portfolio includes the likes of SpaceX, Tesla, Planet, Memphis Meats, Hotmail, and the deep learning companies Mythic and Nervana. Steve also sits on the board of both SpaceX and Tesla. Prior to founding Future, Steve was the co-founder of renowned valley firm Draper Fisher Jurvetson where he led investments in 5 companies that went public in successful IPOs and several others that became billion-dollar acquisitions. In Today’s Episode You Will Learn: 1.) How Steve made his way into the world of startups and Silicon Valley and how that led to his creation of “The Lean Startup Movement”? 2.) How does Steve think about and assess market timing? How does Steve assess technical risk? Given the long term horizons of such deep tech projects, does Steve think we need to change the 10 + 2-year fund life structure? How would Steve like to see funds structured? 3.) Given the sheer size of outcomes if these plays work, how does Steve assess his own price sensitivity? How does Steve approach the challenge there is a lack of downstream investors for such deep tech projects? How does Steve try and catch an industry on the cusp of a transition? 4.) How does Steve assess his own relationship to money? How has it changed over the years? Why does Steve fundamentally believe that venture partnerships do not scale? Where do venture partnerships breakdown? How can one introduce cognitive diversity into a firm? 5.) Having worked with Elon Musk across both SpaceX and Tesla, what does Steve believe makes Elon one of the most gifted entrepreneurs of our time? What is Steve's most memorable moment from his many years of friendship with Elon? What have been his biggest takeaways from SpaceX and Tesla? Items Mentioned In Today’s Show: Steve’s Fave Book: Out Of Control: The New Biology of Machines, Social Systems, and the Economic World Steve's Most Recent Investment: Prellis Biologic As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Clay Wilkes is the Founder & CEO @ Galileo, the API standard for card issuing and digital banking, powering many of the leading global FinTech companies including Chime, TransferWise and Monzo to name a few. Prior to their reported $1.2Bn acquisition by SoFi, Clay raised just $86M in funding with Galileo from the likes of Accel and Ryan Smith @ Qualtrics, having run the company as a profitable company before that for over 15 years. Clay also has a keen interest in philanthropy having created the Galileo foundation with his wife in 2005. In Today’s Episode You Will Learn: 1.) How Clay made his way into the world of tech and startups more than 20 years ago and how he came to build the foundations for many fintechs today with Galileo? 2.) When looking at the current financial ecosystem does Clay believe we are in a phase of bundling or unbundling? Does Clay believe we will see the verticalisation of banking? Will every company become a payments company? Does Clay believe we will see consolidation in the space? 3.) What does Clay believe were the benefits of going 15 years withour raising VC money, building a profitable business? What are the trade offs? What could he have done if he had raised? With hindsight, does Clay wish he had raised earlier? Why was then the right time to raise? 4.) Why does Clay believe the discovery mechanism for VCs finding startups is broken? How did Clay select the venture firm he chose to work with, Accel? What advice does Clay give to board members when it comes to being the best board member to their founders? 5.) Why did Clay believe that selling to SoFi was the right decision? What are the benefits of the merger? How does Clay think about the competitive element that many of Galileo's current clients are competitors with SoFi? How do they remedy and solve for that today? Items Mentioned In Today’s Show: Clay’s Fave Book: Why Nations Fail: The Origins of Power, Prosperity and Poverty As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Brad Feld is a Co-Founder and Managing Director @ Foundry Group, one of the most successful venture firms of the last decade with a portfolio including the likes of Zynga, Fitbit and Sendgrid to name a few. Brad is also a co-founder @ Techstars and prior to Foundry, he co-founded Mobius Venture Capital.  Tracy Lawrence spent the last 8 years as Founder & CEO @ Chewse, the startup that it effortless for office managers to order delicious food for their teams.  Tracy grew the team to 300 people across 4 markets, raised millions in venture capital, and ultimately sold the business to Foodee. Jerry Colonna is the CEO of Reboot.io where he is now the professional coach to some of the world's leading founders. Prior to his work with Reboot, Jerry was an early-stage VC co-founding Flatiron alongside Fred Wilson in 1996. In Today’s Episode You Will Learn: 1.) How did Brad, Jerry and Tracy all experience their first forms of depression? At what stage did it become a more prominent part of their life? Why do they think then was the catalyst? 2.) Why does Jerry believe that despite what people say, no one is crushing it? How can founders present their vulnerability as a strength? At what point did Tracy realise this? How did she convey her vulnerability to her team? Who is to blame for the lack of vulnerability and fear of opening up? 3.) How does Brad think about tying happiness to milestones? What are the biggest dangers of doing so? Does this mean one does not have goals? How does one balance between ambition and appreciating the present? How did Brad learn this when Amy asked for a divorce? How did he respond? 4.) Why does Brad believe fear, guilt and anxiety are useless emotions? What was the result of Tracy tying her mental state to her revenue line? How does Tracy think about the loneliness of being a founder? What does Brad believe is some of the biggest BS in the industry? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Steve Blank is one of the leading luminaries of Silicon Valley, credited with being foundational to the creation of The Lean Startup movement and having spent the last 9 years at Stanford University as a professor and the last 8 as a Senior Fellow @ Columbia University. Steve is the author of "The Four Steps To The Epiphany" and "The Startup Owner's Manual". Prior to joining the world of academics and writing Steve spent over 20 years in the world of entrepreneurship as part of, or co-founded eight Silicon Valley startups ranging from semiconductors, video games, personal computers, and supercomputers. If that was not enough, Steve is also on the Defense Business Board for the United States Department of Defence. In Today’s Episode You Will Learn: 1.) How Steve made his way into the world of startups and Silicon Valley and how that led to his creation of "The Lean Startup Movement"? 2.) Why does Steve vehemently disagree with Adam's Smith's "Invisible Hand" theory when it comes to government intervention? Why is this proven to have failed? How does this only help the rich become richer? As a result, what needs to change in the mechanics of the economy? 3.) Why does Steve not believe that there is accountability placed on investors and founders for projects they create and invest in? Why does Steve believe for the majority of investors today, they have no social conscience? How could this be changed and improved? 4.) How did seeing the booms and busts of the dot com and 2008 impact Steve's operating mentality? What are the 3 core traits that will ensure success for founders in a post COVID world? How should founders change their decision-making process post-COVID? Why does Steve believe in "benign dictatorship"? Items Mentioned In Today’s Show: Steve’s Fave Book: Innovator's Dilemma: When New Technologies Cause Great Firms to Fail As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Mather is the Founder & CEO @ The Athletic, the startup bringing you in-depth sports stories you won't hear anywhere else. To date, Alex has raised over $139M with The Athletic from some of the best in the business including Founders Fund, Bedrock, Y Combinator and Emerson Collective to name a few. Before founding The Athletic, Alex spent an incredible 5 years as part of the hyper-growth @ Strava serving Vice President of Product Management and Product Design. In Today’s Episode You Will Learn: 1.) How Alex made his way into the world of tech and startups with Strava? How did his time at Strava lead to his founding The Athletic? 2.) With the scaling of The Athletic to over 500 people, how has Alex seen his leadership style change and adapt? What does he need to improve? How did having children impact how he thinks about management? What lessons did he take from Strava on what worked for community building? 3.) What was it like raising money for a subscription media business back in 2016? Who was the first person to really take a bet on Alex and The Athletic? What value adds does Alex think are the most important for VCs to provide? What are the biggest investor misconceptions around media? 4.) How does Alex see the future structure of the media landscape? What elements of media is Alex most concerned about right now? Does Alex view Substack as competition? What does Alex believe will be the 2 ways to succeed in media moving forward? 5.) What have been the biggest customer acquisition learnings for Alex from The Athletic? How does Alex feel about platform reliance for customer acquisition with Facebook? What does it take to successfully acquire customers on Facebook at scale? Items Mentioned In Today’s Show: Alex’s Fave Book: The Kingdom of God is Within You As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Joe Lonsdale is a General Partner @ 8VC and in the past has invested in many notable companies including Wish, Oculus, Oscar and Guardant Health. As a result, in both 2016 and 2017, Joe was the youngest member of the Forbes 100 Midas List. Prior to 8VC, Joe co-founded Palantir, one of the world's most impactful multi-billion dollar software companies. Joe also co-founded and serves as Chairman @ Addepar, which has over $1.8 trillion managed on its wealth management technology platform. If that was not enough, Joe is also a founder of Affinity, Anduin and Esper. In Today’s Episode You Will Learn: 1.) How Joe made his way into the world of tech and startups, came to co-found Palantir and Addepar and how that led to his founding 8VC? How does Joe believe the study of history makes one a better investor? 2.) Why does Joe believe that the best VCs are company builders? How does Joe think about, evaluate and put into action the incubator model? How does Joe respond to LPs that suggest it is a distraction? How does voting for incubations differ for investment voting? 3.) What does contrarian thinking really mean to Joe? What does Joe do to specifically engender contrarian thinking in the 8VC partnership? What is the relationship between contrarianism and political correctness? How does Joe think about the dangers of woke culture today? 4.) How does Joe advise founders to think through cash burn and runway today? What is going to happen to companies that sacrified growth for gross margin in 1 year? How does Joe advise founders on the balance of sticking to your vision and mission vs knowing when to give up? 5.) Why does Joe think it is important to not just start new companies but new cities also? Despite the insane cost of living, why does Joe believe the Valley has given rise to the insane levels of innovation it has done? Will the dominance of the valley remain over the next decade? Items Mentioned In Today’s Show: Joe’s Fave Book: How Innovation Works, A Time to Build: From Family and Community to Congress and the Campus Joe’s Most Recent Investment: Beacon As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Julia DeWahl is one of the rising stars of the Silicon Valley angel investor community with a portfolio including the likes of Linear (Sequoia-backed), Modern Fertility (USV backed) and Primer (Founders Fund backed). Prior to angel investing Julia was one of the first 10 employees at Opendoor seeing their hyper-growth first hand in many different roles from Head of Seller Experience to being General Manager of Pheonix & City Operations. Before Opendoor, Julia spent 3 years as a consultant at Bain. If that was not enough, Julia is also an avid cyclist and is setting up a women's cycling apparel line alongside her investing. In Today’s Episode You Will Learn: 1.) How Julia made her way into the world of startups with Opendoor from Bain and how that position at Opendoor led to her angel investing? What were the 1-2 takeaways for Julia from her time at Opendoor that have most impacted how she angel invests today? 2.) Customer Discovery: When is the right time to engage in deep customer discovery work? How does one select the customers to go deep with? How does Julia structure the process? What questions are most revealing? Where do many go wrong? How does one determine the feedback to accept vs which to reject? 3.) How does Julia think about implementing systems for growth? What is the structure of these systems? Where does one start? How does Julia determine the metrics to track and focus on? How does Julia balance between growth vs profitability? 4.) Does Julia believe people can really scale with the company? What are the leading indicators that people are struggling to scale with the company? How does Julia advise generalists to survive and thrive in a scaling organisation? Should they specialise? 5.) What have been some of Julia biggest lessons of what it takes to be successful as an angel today? Who has Julia learned and gained the most from in this new discipline? How does Julia measure her own success as an angel? What are the core challenges? Items Mentioned In Today’s Show: Julia’s Fave Book: The Courage To Be Disliked: How to free yourself, change your life and achieve real happiness Julia’s Most Recent Investment: Primer: Homeschool with superpowers As always you can follow Harry and The Twenty Minute VC on Twitter here!

Oren Zeev is the Founding Partner @ Zeev Ventures, one of the best and most under the radar firms in the early stage Silicon Valley landscape. Over the past decade, Oren has backed the likes of TripActions, Tipalti, Audible, Houzz, Chegg and Hippo Insurance to name a few. Prior to crushing it with Zeev Ventures, Oren spent 12 years as a General Partner @ Apax Ventures, starting in Israel and then moving to the US where he headed the Technology Practice of Apax and the Silicon Valley office. In Today’s Episode You Will Learn: 1.) How Oren made his way into the world of venture with Apax and how that led to his founding his own firm, Zeev Ventures? 2.) Having been in a venture partnership, why did Oren want to be a solo GP? What are the benefits? How does it change decision-making? What are the downsides? How does Oren discuss deals and ideas without partners? How does Oren explain the decision to LPs on being a solo GP? 3.) Why does Oren not believe in thesis-driven investing? What are the dangers and downsides to it? Why do most managers still do it then? Why does Oren specifically look for under-appreciated markets? How is pricing and competition different there? How does Oren assess his own price sensitivity? 4.) Why does Oren think that diversification is overrated? How does Oren think about cross-fund investing? Why is it such a strength that managers should use? Why do many not do it? How does Oren think about reserve allocation? Why is he the only VC to not have a reserves strategy? 5.) How does Oren think about fund deployment timelines? Why do LPs not like the annual fundraising approach? How does Oren size up his position in companies over time and round? How does Oren feel about founders taking secondaries? Items Mentioned In Today’s Show: Oren’s Fave Book: The Last Lion: Winston Spencer Churchill: Defender of the Realm Oren’s Most Recent Investment: Treeverse As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Lo Toney is the Founding Managing Partner @ Plexo Capital, a very unique firm making both direct investments and fund investments. They have invested in Precursor, Boldstart, Female Founders Fund and WorkBench on the fund side and then PlayVS, Replicated and StyleSeat on the direct side. Prior to Plexo, Lo was a Partner @ GV (Google Ventures) and before that was a Partner with Comcast Ventures where he led the Catalyst Fund. Before venture Lo was an operator enjoying exec roles at Zynga, Nike and eBay. In Today’s Episode You Will Learn: 1.) How Lo made his way into the world of venture with GV and how that led to his innovating on the venture model investing in both funds and directly with Plexo today? What were Lo's biggest takeaways from his 5 years as a Partner @ GV? 2.) How will GPs raising today be impacted by COVID? How does this differ dependent on the stage they invest and the size of fund they are raising? How does Lo advise managers communicating with existing and new potential LPs today? 3.) What does Lo mean when he discusses your "minimum viable fund size"? How does Lo advise GPs when it comes to closing strategies? How much do they need for first close? How many closes should there be thereafter? Should they take the money when it is on the table? 4.) How does Lo feel about anchor LPs taking/investing in the GP? What are the benefits for the manager of doing so? Why does Lo believe there is such a binary view towards it? Why does Lo disagree with the benchmarks set of what a GP commit "should be"? 5.) Why does Lo believe we will see the hybridization of GP/LP over the coming years? What are the benefits of having your LP also direct invest? What are the core challenges to the model? How does Lo envisage the world of venture evolving over the next decade? Items Mentioned In Today’s Show: Lo’s Fave Book: Why Should White Guys Have All the Fun?: How Reginald Lewis Created a Billion-Dollar Business Lo's Most Recent Investment: PlayVS As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.      

Andrew Wilkinson is the Managing Partner @ Tiny, a vehicle that buys, builds and invests in wonderful internet companies. Within their family of companies is Dribble; home to the world's best design professionals; MetaLab and Supercast to name a few. Tiny does also make venture investments in the likes of Superhuman, SpaceX, Pitch and Buffer. Today Andrew oversees a group of companies with over 300 employees and tens of millions in revenue. In Today’s Episode You Will Learn: 1.) How Andrew made his way from founding a design agency in Canada to starting Tiny and building a family of companies with over 300 people? 2.) What does Andrew mean when he says, when buying companies he looks for companies like New Zealand? What qualities/features do they have? How does Andrew think about price sensitivity when acquiring these companies? What determines paying a premium price to Andrew? 3.) How does Andrew assess and analyse true defensibility within company strategies today? Why does Andrew not believe they will lose any companies? How does Andrew think about grow vs profitability? Are they mutually exclusive? When does one pour fuel on the fire and raise big? 4.) How has Andrew seen himself develop and change as a leader over the last 5 years? What does truly great delegation look like? What is Andrew's biggest weakness? What is his biggest insecurity? How does Andrew think about sink the boat vs non-sink the boat decisions? 5.) Does Andrew believe we will see the unbundling of social networks moving forward? What are the core characteristics that determine whether a social network will win? Why does Dribble have defensibility as a brand against all large incumbents? Items Mentioned In Today’s Show: Andrew’s Fave Book: Tao of Charlie Munger: A Compilation of Quotes from Berkshire Hathaway's Vice Chairman As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

David Sacks is the Co-Founder @ Craft Ventures, one of Silicon Valley's leading early-stage funds with David's portfolio including the likes of Facebook, Tesla, SpaceX, Palantir, Affirm, Airbnb, Slack and Bird to name a few. David started his career in tech as the first product leader and COO @ Paypal, growing payment volume from $0-$500M per month, leading to their $1.5Bn acquisition by eBay. David then founded Geni.com, creating a family tree for the whole world, the company was acquired 3 years later by MyHeritage. David then founded Yammer, the secure solution for internal corporate communication and collaboration, acquired by Microsoft for $1.2Bn. Finally, David then became COO and Interim CEO @ Zenefits before starting Craft. In Today’s Episode You Will Learn: 1.) How David made his way from founding Yammer to creating one of the valley's newest and most prestigious firms in Craft Ventures? Given David's operating success he could have angel invested continuously, why decide to start a fund? What does he ultimately want to achieve with Craft? 2.) How did experiencing the Dot Com Bubble with Paypal and then 2008 impact David's investing and operating mindset? Does David believe VCs really are "open for business" today? How is VC behaviour shifting when comparing early to later stage? How is Craft responding? 3.) Unit Economics: How does David assess unit economics in early-stage opportunities he is looking to invest in? What does proper attribution look like? Where do many go wrong with unit economics? Is it too early to try and assess unit econ at seed? How does David think about having mental plasticity towards unit economics, recognising how they change over time? 4.) Customer Acquisition: Does David agree with Peter Fenton, "there is a complete lack of free and open distribution"? What are the rules of thumb on CAC that David does and then does not agree with? How does David feel about blended CAC? What separates good from great when it comes to CAC/LTV? 5.) Churn: How does assess net negative churn in the businesses he works with? What is great, good, decent and poor? How does avid think about logo vs dollar retention? How does David advise founders who feel COVID has not impacted churn for them? What should they expect? 6.) Burn + Capital Efficiency: How does David analyse burn and capital efficiency today? What does he mean when he discusses "the burn multiple"? How should the burn multiple change with the stage of the business? How does David advise founders on how aggressively to cut burn today? Items Mentioned In Today’s Show: David's Fave Book: Thucydides’ Trap David's Most Recently Announced Investment: Sourcegraph As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Chris Best is the Founder & CEO @ Substack, the company that makes it simple for a writer to start a paid newsletter. To date, Chris has raised over $17M in funding from the likes of a16z, Y Combinator, Twitch CEO Emmett Shear and Zynga Co-Founder Justin Waldron to name a few. Prior to founding Substack, Chris was the Co-Founder & CTO @ Kik, letting users connect with friends, groups and the world around them. The company raised over $220M in funding from Spark, Tencent and USV to name a few. In Today’s Episode You Will Learn: 1.) How Chris made his way into the world of startups and came to found Kik? How his journey with Kik led to his founding Substack? 2.) During COVID, traditional media publications have been hit hard and Substack has taken off, how does Chris see the correlation there? Given the public journal of record has always been free, how does Substack interact with public news? What does Chris 3.) Why does Chris believe that micropayments are a fundamentally bad idea? Structurally why would they not work? Does Chris agree the biggest problem consumers face today in content is one of discovery? Why not? 4.) When designing the Substack product today, how does Chris think about incentive design? Why does Chris believe with incentives, Substack is the opposite of Twitter from a product perspective? Why have the "economics of attention now been flipped?" 5.) How has Chris seen himself evolve and change as a leader over the last 3 years? What advice would Chris give to CTOs making the move into the role of CEO? What does Chris believe his greatest strengths and weaknesses are as a leader? How does Chris find the war for talent today? Items Mentioned In Today’s Show: Chris’ Fave Book: The Death and Life of Great American Cities As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Merci Victoria Grace is a Partner @ Lightspeed Venture Partners, one of the valley's leading venture firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Affirm, AppDynamics and more. As for Merci, prior to entering the world of venture, Merci spent 3 years at Slack including as Head of Growth where she grew the growth team to over 50 people and drove DAU's from 500K to 5M in under 2 years. Merci is also the Founder of Women In Product a global community of incredible women in product management. CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Merci made her way into the world of venture having led the growth team at Slack for close to 3 years? 2.) Merci has been working to productise venture, so what core elements of venture need productising? What systems and tools has Merci put in place to create a product around these processes and methods? What have been the biggest challenge in the attempt to productise VC? 3.) How does the decision-making process look like at Lightspeed? How does Merci use post mortems to help her improve post having lost a deal? How does she structure those post-mortems? What have been some of the core takeaways? What internal tech stack does LSVP run itself on? 4.) How does Merci see the future of the collaboration tools market? Are we entering a period of bundling or unbundling? How does Merci feel about the debate between synchronous and asynchronous? How does Merci determine between those who have grown sustainably vs unsustainably in the time of COVID? 5.) Why do the majority of collaboration tool startups fail? What do they get so wrong in their go-to-market? For those that succeed, what are the commonalities in those that succeed? Why is being good at Twitter a competitive advantage? How does Merci feel about the Superhuman, high touch onboarding style? Items Mentioned In Today’s Show: Merci’s Fave Book: Never Split The Difference: Negotiate As If Your Life Depended on It As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Ryan Petersen is the Founder & CEO @ Flexport, the operating system for global trade with over $1.3Bn in funding from the likes of Softbank, Founders Fund, DST, GV and First Round to name a few. Justin Kan is the Founder @ Atrium and Twitch (acq by Amazon for $1Bn). Justin is also a prolific angel with a portfolio including the likes of Scale AI, Digits, Cruise and Triplebyte to name a few. Matteo Franceschetti is the Founder & CEO @ Eight Sleep, the #1 Smart Mattress, designed to help you fall asleep faster and stay asleep. To date, Matteo has raised over $70M from Founders Fund, Khosla Ventures, Craft Ventures, Kevin Hartz and Ryan Petersen to name a few. Steve Schlafman is a Coach and Investor @ High Output. Previously Steve was a Partner @ Primary Ventures in NYC and before that Principal @ RRE. CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) What was your realisation moment for stopping drinking? How did it come about? What was your prior relationship to alcohol like? 2.) For me I always found an excuse to not stop drinking, when you think about your attempts to give up, what excuses did you provide as reasons for continuing to drink? What insecurities and vulnerabilities did drinking hide and mask for you? How did it impact them? 3.) From a literal standpoint, how did you approach giving up the act of drinking? What tools did you find most helpful? What resources do you recommend? How has your life changed since you stopped drinking? Matteo, you have the data from Eight Sleep, what does the data say about how stopping drinking truly impacts your sleep? 4.) People often say that stopping drinking kills your social life, what would you respond to that commonly held belief? What other core misconceptions do you find people hold towards drinking? To those considering giving up drinking, what would you advise them? What do you know now about alcohol that you wish you had known earlier? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Avi Meir is the Founder & CEO @ TravelPerk, the travel management platform that combines the best of leisure and corporate travel into one smooth experience. To date, Avi has raised over $134m with TravelPerk from the likes of DST, Spark Capital, Felix Capital and Heartcore to name a few. Prior to founding TravelPerk, Avi co-founded HotelNinjas, a hotel management product that was acquired by Booking.com. Before that Avi was VP Product at budgetplaces where he managed a team of 50 across product and marketing. In Today’s Episode You Will Learn: 1.) How Avi made his way into the world of startups and came to change the way we think of corporate travel with TravelPerk? 2.) Why has Avi advocated for the re-opening of society much sooner than others have done? If Avi were in government, what would he advocate for and do? How does Avi try and effectively assess the core risks of COVID both from a societal and economic perspective? 3.) How does Avi feel when he hears the comparison of COVID to Saars or 9/11 when it comes to their impact on travel? Why is this so different? Why does Avi believe 2021 will be a bigger year for business travel than 2019? 4.) How does Avi advise founders heavily impacted by COVID to really effectively analyse their spend and optimise runway? How does Avi think approach the element that sales and marketing is now non-revenue driving? How does Avi approach resource allocation as a result? 5.) Does Avi believe we will see a fundamental re-shaping of corporate travel? What will change? How does domestic travel change? What will the landscape look like on the other side? Who will survive? Who will thrive? Does Avi feel now is an opportune time for M&A? Items Mentioned In Today’s Show: Avi’s Fave Book: The Hundred-Year-Old Man Who Climbed Out of the Window and Disappeared As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Elad Gil is one of Silicon Valley's most successful and prominent angels of the last decade with a portfolio including the likes of Stripe, Square, Airbnb, Pinterest, Instacart, Flexport and Brex to name a few. Prior to solely company investing, Elad was an operator as Founder and CEO @ Color Genomics for their first 3 years. Before Color, Elad was a VP of Corporate Strategy @ Twitter following their acquisition of the company he founded, Mixer Labs. Before founding Mixer, Elad spent 3 years at Google where he was involved with 3 acquisition including the Android acquisition. In Today’s Episode You Will Learn: 1.) How Elad made his way into the world of startups and how that led to his investing in some of the most prominent companies of the last decade? 2.) How is the venture and startup landscape shifting right now? What does Elad make of the large multi-stage funds re-entering seed? How does Elad advise founders when it comes to taking secondaries? 3.) What are the core elements startups need to assess to fully understand their cash position? What is the optimal runway to have and to raise for today? How can founders stress test their runway models? Where does Elad see the most mistakes when it comes to runway? 4.) Does Elad believe the VC messages of "Open for Business" during COVID? How does Elad advise founders when it comes to valuation sensitivity today? What are the core terms that founders should watch out for when raising? How does Elad see venture fund reserve allocations changing? 5.) What are the core tenets of an effective layoff strategy? How should they determine the right level of aggression with which to make cuts? How can layoffs be done in a way that maintains internal culture and morale? Where does Elad see many going wrong when it comes to layoffs? 6.) Which business will thrive in COVID times? Which will die? What are the leading indicators of each? How does Elad determine in the businesses that are growing immensely during COVID, those that are sustainable growth and those which are purely due to COVID? Items Mentioned In Today’s Show: Elad’s Fave Book: Master of the Senate: The Years of Lyndon Johnson Elad’s Most Recent Investment: Deel As always you can follow Harry, The Twenty Minute VC and Elad and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ariel Cohen is the Founder & CEO @ TripActions, the company trusted by more than 4,000 companies to manage their business travel and expenses. To date, Ariel has raised more than $980M with TripActions from the likes of Lightspeed, Oren Zeev and a16z to name a few. Prior to TripActions, Ariel co-founded StreamOnce, a business multimedia integration platform which was acquired by Jive Software. Prior to StreamOnce, Ariel led Product Management in a senior leadership role at Hewlett-Packard. In Today’s Episode You Will Learn: 1.) How Ariel made his way into the world of tech and came to change the way we think about business travel today with TripActions? 2.) What are TripActions doing in their business to be there for their partners, customers and suppliers in the long term? TripActions engaged in layoffs, how did Ariel approach the size of layoff required? What is the right way to do layoffs? How does this change in a remote world? 3.) Given the uncertainty, how does Ariel advise founders to assess and correct their burn and spending? What is a reasonable amount of runway to reserve for? For those hit hard on the demand side, what can they do to build durable defensibility when they can't scale demand? 4.) How does Ariel view the future of business travel? Does Zoom replace much of the business trips? What will the landscape look like in 3 years? What players will survive? Who will thrive? 5.) From a founder psychology perspective, what has Avi done to cope in these very challenging times? What has worked? What has not worked? What does Ariel advise founders struggling to cope psychologically? What can investors do to be there for their founders? Items Mentioned In Today’s Show: Ariel’s Fave Book: Mr Vertigo As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Hamilton Helmer is the Managing Partner & Chief Investment Officer @ Strategy Capital a long-only public equity fund that selects securities for investment based on Power Dynamics, a proprietary model of fundamental value, developed by Hamilton over decades of strategy consulting with clients such as Hewlett-Packard, Adobe and more. Hamilton is also the author of one of my favourite books, 7 Powers. If that was not enough, Hamilton is also an Instructor in the Economics Department @ Stanford University. In Today’s Episode You Will Learn: 1.) How Hamilton made his way into the world of investing from advising some of the largest tech titans on the planet with Adobe and HP? 2.) What is a strategy mental model? What makes the most effective strategic models? What characteristics do they have? How should founders balance between sticking to models and being willing to change them? What are Hamilton's biggest takeaways from working with Netflix? 3.) "All strategy begins with invention", what did Hamilton mean by this? How does Hamilton explain the success of copycats in markets? How does Hamilton separate between first mover and creator? How does Hamilton analyse the transition from startup to pricer with scale economics? 4.) How does Hamilton advise founders to view and approach competition? Why does Hamilton totally disagree with the requirement of being 10x better than your competition? Is product innovation alone enough without brand or business model innovation? 5.) How does Hamilton define "brand"? Is brand an attainable strategy alone or is it the byproduct of something else? How transferable is brand in one category to alternative categories? How does a brand truly know when they have sustainable leverage and power? Items Mentioned In Today’s Show: Hamilton’s Fave Book: The Road to Reality: A Complete Guide to the Laws of the Universe, Stardust As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sarah Kunst is the Founder and Managing Director @ Cleo Capital with a portfolio including the likes of StyleSeat, Glow Bar and PlateJoy to name a few. Prior to venture, Sarah served as a senior advisor at Bumble where she focused on their corporate VC arm, Bumble Fund, and on the board of the Michigan State University Foundation endowment. If that was not enough, Sarah is also a contributing editor @ Vanity Fair. Due to her success, Sarah has been named a Future Innovator by Vanity Fair and a top woman in VC by Wall St Journal. In Today’s Episode You Will Learn: 1.) How Sarah made her way into the world of venture from Bumble and how that led to her founding Cleo Capital? 2.) Does Sarah believe VCs really are still "open for business"? What does Sarah make of all the dry powder sitting on the sidelines? How does Sarah think reserve allocation strategies will change today? Why does Sarah believe another great vintage of funds is to come, as it did in 08'? 3.) What would Sarah most like to change about the world of venture? Does Sarah agree that GP commit expectations prevent diversity in venture? How was the fundraising process for Sarah? How can VCs prove skin in the game without having personal capital? 4.) What is the #1 piece of advice Sarah is giving her founders in these COVID times? How does Sarah advise her founders on approaching the talent market today? How does Sarah advise her founders on burn and capital allocation given COVID? Items Mentioned In Today’s Show: Sarah’s Fave Book: Attached: Are you Anxious, Avoidant or Secure? How the science of adult attachment can help you find – and keep Sarah’s Most Recent Investment: Planet Forward As always you can follow Harry, The Twenty Minute VC and Sarah and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mike Maples is a Founder & Partner @ Floodgate, one of the leading early-stage firms of the last decade with investments in the likes of Lyft, Twitch, Twitter, Okta and Sonos to name a few. He has been on the Forbes Midas List since 2010 and was also named one of “8 Rising Stars” by FORTUNE Magazine. Before becoming a full-time investor, Mike was involved as a founder and operating executive at back-to-back startup IPOs, including Tivoli Systems (IPO TIVS, acquired by IBM) and Motive (IPO MOTV, acquired by Alcatel-Lucent.) In Today’s Episode You Will Learn: 1.) How Mike made his way from founding startups to entering the world of venture and the gap he saw in the market when founding Floodgate? 2.) Mike has previously said, "a startup is not a company, it is a series of breakthroughs". How does Mike define a breakthrough? What are the 2 most meaningful breakthroughs a startup can experience? Which excites Mike the most to see? How do the best startups scale pre-breakthrough to post-breakthrough? 3.) What are the core ways inflections can create breakthrough opportunities? What were Mike's learnings on inflections from investing in Lyft? What does Mike mean when he talks about the importance of "backcasting"? What did investing in Twitch teach Mike about forecasting? 4.) How does Mike feel about the rise of operator and angel funds? How does Mike analyse the re-entrance of large multi-stage funds back into seed markets? Does Mike agree with Semil Shah, "founders are voting with their feet and taking multi-stage money at seed"? 5.) As Mike's peers have all moved into larger funds, Mike did not, why? How does Mike view "fund size as your strategy"? How does Mike think about the centrality of ownership? Does Mike really believe you can concentrate capital into your winners? What are the challenges? Why does Mike feel self-promotion is one of the biggest challenges in VC? Items Mentioned In Today’s Show: Mike’s Fave Book: Superforecasting: The Art and Science of Prediction Mike’s Most Recent Investment: CommonStock As always you can follow Harry, The Twenty Minute VC and Mike and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Conor White-Sullivan is the Founder & CEO @ Roam Research, the tool taking over our industry providing a seamless note-taking tool for networked thought. Prior to founding Roam, Conor founded 2 prior businesses and also worked at HuffPost as a Co-Founder of HuffPost Labs where he reported directly to Arianna Huffington and HuffPost CTO. In Today’s Episode You Will Learn: 1.) How Conor's high school wrestling career taught him "how to win"? What was the founding story with Roam? How does Conor think about when to stay true to the vision and persist vs when to give up? 2.) How does Conor think about the product design philosophy they have @ Roam? Conor has said before, "Roam is not about taking better notes", what is Roam about then? How does Conor think about the importance of adding challenge to a product? What does he mean when he discusses the importance of "low floors and high ceilings" with regards to product design? 3.) How would Conor analyse his own hiring and team-building philosophy? Why are the two most important traits, "girt and autodidacts"?How does Conor really stress these two characteristics in an interview process? Why does Conor choose to live with the team? What are the benefits of this? 4.) Does Conor believe we are in a phase of bundling or unbundling when it comes to collaboration tools? Does Conor believe we will see large players acquire and consolidate over the coming months? Why does Conor compare Roam more to Google than other collaboration tools? 5.) How does Conor think about go-to-market today? What were some of Conor's biggest takeaways for bootstrapping for years with revenue from customers? Why is Conor borrowing from the Tesla GTM? What does that really mean in practice? Items Mentioned In Today’s Show: Conor’s Fave Book: How to Read a Book: The Classic Guide to Intelligent Reading As always you can follow Harry, The Twenty Minute VC and Conor and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Mark Cuban is a serial entrepreneur, investor, and owner of the Dallas Mavericks. His career began with his founding of MicroSolutions, a company he went on to sell to CompuServe in 1990. Then in 1995 Mark co-founded Broadcast.com - streaming audio over the internet. In just four short years, Broadcast.com (then Audionet) was sold to Yahoo for $5.6 billion dollars. Following the acquisition in 2000, Mark acquired the Dallas Mavericks where since his taking over they have competed in the NBA Finals for the first time in franchise history in 2006 - and becoming NBA World Champions in 2011. They are currently listed as one of Forbes' most valuable franchises in sports. If that was not enough, Mark is also one of ABC's "Sharks" on the hit show Shark Tank. In Today’s Episode You Will Learn: 1.) How Mark made his way into the world of technology and startups having been fired from his first job in sales? 2.) How does Mark evaluate his relationship to wealth and money? How has that changed over time? What advice does Mark have to those that tie happiness and money together? 3.) What does Mark think about Silicon Valley investors today? Why does he believe they and the valley are like Hollywood? Why does Mark believe that if the greatest tech companies of today had been started elsewhere, they would be more successful? 4.) How does Mark evaluate his own investing philosophy today? How does Mark think about price and price sensitivity? Why is Mark so keen to have his investment funded from the cashflow of the business? Does this not narrow opportunity and limit upside? How does Mark evaluate risk today? 5.) Why does Mark believe post-COVID is the single greatest time to be an entrepreneur? What advice would he give to an entrepreneur starting their new business in this time? How would Mark go about the re-opening of society post lockdown? Items Mentioned In Today’s Show: Mark’s Fave Book: Rebooting AI: Building Artificial Intelligence We Can Trust, Healthy Buildings: How Indoor Spaces Drive Performance and Productivity As always you can follow Harry, The Twenty Minute VC and Mark and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.