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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.
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Apr 13, 2022

Domm Holland is the Founder and CEO @ Fast.

Last week Fast announced they would be shutting down the company.

In this exclusive 20VC episode we discuss:

  • What really happened with Domm's towing business in Australia?
  • What are the 1-2 biggest mistakes made at Fast?
  • Why has Bolt worked in a way that Fast has not worked?
  • What is it like having Stripe as an investor in your company?
  • Could the board have done more to prevent what happened at Fast?

 

Apr 11, 2022

Avichal Garg is Co-Founder & Partner @ Electric Capital, last month Electric announced they had raised $1BN for their new fund making them one of the largest independent and crypto-native VC firms in the world. As for Avichal, prior to Electric, he was an investor in crypto projects such as Anchorage, Bitwise, Lightning Labs, and OpenSea and unicorns such as Airtable, Cruise, Deel, Figma, Notion and many more. On the operating side, Avichal successfully sold his last company to Facebook where he became Director of Product Management for the Local product group, a team of 400 engineers responsible for billions in revenue.

In Today’s Episode with Avichal Garg You Will Learn:

1.) Origins into Venture:

  • How did Avichal make his way into the world of startups and angel investing?
  • How did Avichal make the pivot from software to crypto investing?
  • Was Avichal nervous when making the move to institutionalize what had been personal investing?
  • What does Avichal know now that he wishes he had known at the start of Electric?

2.) The Landscape: Crypto Investing

  • How does Avichal assess the crypto fund landscape today?
  • Will we continue to see a small number of firms (a16z, Katie Haun, Paradigm, Electric) dominate the market?
  • What happens to all the small crypto funds that have been raised in the last year?
  • Why does Avichal believe crypto investing is much more collaborative than venture investing?
  • How can venture size returns be made if the ownership levels are so much smaller?

3.) Crypto Firms vs Traditional VC Firms:

  • Why does Avichal believe that crypto is software eating money?
  • What does this mean for traditional venture? Who will survive? Who will die? Who will thrive?
  • Why can generalist firms not compete with crypto native firms?
  • How are the teams of crypto native firms structured so differently to those of traditional VCs?
  • Do crypto projects and investments need the same level of service and help that generalist VCs provide with their platform services?

4.) Tokens - Equity - Liquidity:

  • How does Avichal advise investors on how to think through token vs equity investing?
  • When does it make sense to have a token vs not having a token?
  • How are crypto tokens priced and valued? What do you need to know when buying tokens?
  • How does the liquidity of crypto markets make it challenging for investor psychology?
  • What is the biggest lesson Avichal has learned on when is the right time to sell?

5.) DAOs: 101

  • What are DAOs? Are they not just another form of government?
  • What makes one DAO successful and another not?
  • What tooling and infrastructure are required to manage a DAO successfully?
  • What does Avichal believe the vision of a DAO should be? How should they define success?

Item’s Mentioned In Today’s Episode with Avichal Garg

Avichal’s Favourite Book: The End of the World Is Just the Beginning: Mapping the Collapse of Globalization

Avichal’s Most Recent Investment: Magic Eden

Apr 8, 2022

Eric Liaw is a General Partner @ IVP, one of the leading later-stage venture capital and growth equity firms of the last decade with $8.7 billion of committed capital and a 40-year IRR of 43.1%. At IVP eric has led investments in Datadog, Github, Klarna, Robinhood and UiPath to name a few. Prior to joining IVP, Eric was with Technology Crossover Ventures (TCV) and was actively involved in originating, executing and managing investments, including Netflix, Zillow and eHarmony. As a result of his investing success, Eric was recognized by GrowthCap as one of the Top 25 Software Investors of 2021 and 2020.

In Today’s Episode with Eric Liaw You Will Learn:

1.) Origins into Venture:

  • How did Eric make his way into the world of venture way back over 20 years ago?
  • What were some of Eric's biggest lessons from his early years at TCV?
  • What are the most significant changes in venture over the last decade?

2.) Eric Liaw: The Investor:

  • How has Eric changed as an investor over the last decade? What caused those changes?
  • How does Eric reflect on his own relationship to price? How does he determine when to pay up vs when to remain disciplined?
  • What has been Eric's biggest miss? How did it alter his style of investing?
  • From UiPath to Supercell, what has been Eric's favourite story of travelling around the world to win a deal?

3.) The Market: Venture

  • How does Eric expect IPO markets to behave as we move further in 2022?
  • How does Eric expect large M&A to play out for the rest of the year?
  • With the public markets crashing; how does this impact the large growth rounds of 2021?
  • What does Eric expect to happen to early stage pricing with the crash at late stage?
  • How does Eric expect crossover funds to behave in this new environment?

4.) Eric Liaw: The Person

  • How does Eric think about being an awesome Dad and also not losing an inch on being a world class investor?
  • How does Eric reflect on his own ego when having such large investing wins? Where does he feel he is most insecure?
  • How did having children really impact his mindset towards investing and working with founders?

Item’s Mentioned In Today’s Episode with Eric Liaw

Eric’s Favourite Book: No Rules Rules: Netflix and the Culture of Reinvention

Eric’s Most Recent Investment: Aiven

Apr 6, 2022

Brian Hale is Vice President of Consumer Product & Growth @ Doordash. Before joining Doordash, Brian spent an incredible 10 years at Facebook, most recently as VP of Product Growth working across Instagram, Messenger, Whatsapp and more. Prior to Facebook, Brian was Director of Growth @ Uptake.com and it all started for Brian in 1999 working at ACDSee in Canada where he was asked to “figure out that search engine thing”. 

In Today’s Episode with Brian Hale You Will Learn:

1.) Brian Hale: Entry into Growth:

  • How Brian made his way into the world of growth from being a "marine ceramic engineer"?
  • What were 1-2 of his biggest takeaways from his 10-year journey with Facebook?
  • What are 1-2 of the biggest misconceptions about the Facebook growth team?

2.) When is the Right Time:

  • When is the right time for startups to hire their first growth leads or reps?
  • How should the founder allocate resources to the growth team? Hire new designers, engineers etc for the team or pluck them from existing teams within the company?
  • What are the biggest mistakes startups make on the timing of this hire?
  • How can startups accurately assess whether they have product-market-fit?
  • What levels of retention suggest PMF? How does this change by industry?

3.) Who To Hire:

  • Step by step, how does Brian structure the interview process for all new growth hires?
  • What are the must-ask questions for growth leaders to ask candidates in interviews?
  • What are the clear signs and answers that suggest a 10x growth hire? How do the very best interact with data? What do they really hone in on?
  • What literal tests does Brian do to determine the quality of a hire? How do the best perform?

4.) Onboarding and Integration:

  • What is the optimal onboarding process for all new growth hires?
  • What can leaders do to set their new growth teams up for success?
  • What are the biggest ways new growth hires can mess up in the first 60 days?
  • What have been some of the biggest challenges for Brian in his onboarding at Doordash?

Apr 4, 2022

Thomas Tull is a leading entrepreneur and investor as the Founder, Chairman and CEO of Tulco, LLC. he has made notable investments in the likes of FIGS, Colossal, IL MAKIAGE, Pinterest, Zoox and Oculus Rift. Previously, Tull was the founder, CEO and Chairman of Legendary Entertainment, the film company that produced blockbusters including The Dark Knight trilogy, 300 and The Hangover franchise. Outside of his investment work, Thomas is a trustee of Carnegie Mellon University, Yellowstone Forever, the National Baseball Hall of Fame and Museum, and the Smithsonian Institution. If that was not enough, Tull is also part of the ownership group of the Pittsburgh Steelers, the six-time Super Bowl champions.

In Today’s Episode with Thomas Tull You Will Learn:

1.) From Laundromats to Legendary Entertainment:

  • How did Thomas first make his way into the world of business starting with laundromats?
  • How did growing up without money impact Thomas' early mindset?
  • What advice does Thomas give to young people today on starting their own business?

2.) Thomas Tull: The Investor:

  • How does Thomas approach risk today? Where is the boundary of acceptable vs unacceptable risk?
  • How does Thomas assess his own relationship to money? How has it changed over time?
  • How does Thomas protect himself from people and occasions where one is being used for their money or status?
  • To what extent does Thomas believe success is luck vs skill?

3.) Legendary Entertainment:

  • How did Thomas make his way into the movie business with the founding of Legendary Entertainment?
  • How did Thomas first meet Chris Nolan? What did the early days of making Batman Begins look like?
  • What were some of the most memorable times from making 300 with Gerard Butler?
  • What were some of the most challenging elements of scaling Legendary? With the benefit of hindsight, is there anything that Thomas would do differently?

4.) The Macro:

  • Why does Thomas believe public markets are the least rational they have ever been?
  • From geo politics to climate change, what is Thomas most worried about today in the world?
  • What does Thomas believe we should focus on as positives moving forward? What should we be excited about?

Item’s Mentioned In Today’s Episode with Thomas Tull

Thomas' Favourite Book: Sapiens: A Brief History of Humankind

Thomas' Most Recent Investment: Colossal

Apr 1, 2022

Eduardo Vivas is the Co-Founder and CEO @ Curated, a network where product experts monetize their passion and help consumers make the perfect purchase. To date, Eddie has raised over $141M from some of the best including CapitalG, Greylock and Forerunner to name a few. Eddie is also a stellar angel investor with a portfolio including Telegram, Truebill, AppLovin and Dollar Shave Club among others. Prior to Curated, Eddie spent 3 years at Linkedin as Head of Talent Solutions, following his startup, Bright, being acquired by them in 2014.

In Today’s Episode with Eddie Vivas You Will Learn:

1.) The Founding of Curated:

  • What was the aha moment for Eddie with Curated?
  • What were Eddie's biggest takeaways from his prior companies? What did he take with him that worked? What did he disregard that did not work?
  • What were some of Eddie's biggest lessons from Linkedin? How did it impact his mindset?

2.) The Compound Startup:

  • Why did Eddie decide it was right to build so much of the tooling themselves?
  • How does Eddie determine when to buy vs build?
  • What are the biggest mistakes Eddie sees founders making when building multiple internal tools at the same time?
  • How does build a compound startup increase the strategic value of a company?

3.) Hiring: Missionaries not Mercenaries

  • How does Eddie structure his hiring process at Curated? Why does he not believe that startups are for everyone?
  • What are the biggest signals that a person is a missionary and not a mercenary? How do mercenaries act in a way that is different to missionaries?
  • What questions in an interview process show these traits?
  • What are some of the biggest mistakes Eddie has made when hiring?

4.) Equity and Compensation:

  • What is Eddie's biggest advice to founders when it comes to equity allocations for the team?
  • Why does Eddie believe it is crucial to offer and provide secondaries for the team?
  • How does Eddie feel about the amount of secondaries founders take today so early?

Item’s Mentioned In Today’s Episode with Eddie Vivas

Eddie’s Favourite Book: Predictably Irrational: The Hidden Forces That Shape Our Decisions

Mar 30, 2022

Olivia Nottebohm is the Chief Revenue Officer @ Notion where she leads the Sales, Marketing, Customer Success and Customer Experience teams. Prior to Notion, Olivia was the COO @ Dropbox where she achieved the first 4 quarters of profitable growth. Before Dropbox Olivia spent over 5 years at Google including as VP Cloud GTM Operations and Global SMB Sales. Finally, before Google, Olivia spent a whopping 15 years at McKinsey & Company.

In Today’s Episode with Olivia Nottebohm You Will Learn:

1.) Origins:

  • How Olivia made her way into the world of startups and tech?
  • What are 1-2 big takeaways Olivia has from her 5+ years at Google? How have they shaped her operating mindset today?
  • How does Olivia balance her love for analysis and data with speed and agility of decisions?

2.) Good vs Great Operations (Ops):

  • What does great ops really mean to Olivia? What are the 1-2 things founders can implement today to improve their ops immediately?
  • What are the core mistakes founders make when instilling ops for the first time?
  • How does Olivia coordinate the global Notion team to be as effective as possible?
  • What has worked? What has not worked?

3.) The Hiring Process:

  • Why does Olivia believe all leaders will have to accept they will not have all the talent they need over the coming years?
  • With that in mind, is it best to hire B players or always keep the bar high? If and when can the bar be lowered?
  • How does Olivia construct the hiring process? What are the core questions she will always ask?
  • What is the secret to great referencing? How does Olivia enable the other side to feel safe telling her everything they know about the candidate?

4.) Cross-Functional Communication:

  • How does Olivia advise founders on the best way to get different functions working together?
  • What works? What does not? What are some big mistakes Olivia sees over and over?
  • At what point in company scaling does this comms begin to breakdown?

Item’s Mentioned In Today’s Episode with Olivia Nottebohm

Grow Fast or Die Slow: The role of profitability in sustainable growth

Mar 28, 2022

Jeff Lieberman is the Managing Director @ Insight Partners, one of the leading investing franchises of the last 25 years with their most recent flagship fund announced earlier this year being a staggering $20BN. As for Jeff, over the last 24 years at Insight, he has led investments in leading companies such as Qualtrics, DeliveryHero, HelloFresh, Cvent, Mimecast, and Udemy. As a result of his many investing successes, he has been selected by AlwaysOn as a Venture Capital 100 winner and by Forbes as a member of the Midas List.

In Today’s Episode with Jeff Lieberman You Will Learn:

1.) Origins into Venture:

  • How did Jeff's roommate at college open his eyes to the world of venture capital?
  • What were Jeff's biggest lessons from seeing the work ethic of his parents?
  • How does Jeff imbue the same level of ambition on his children that he had growing up with no money?
  • Why is Jeff keen for his children not to go to college? How does he advise them?

2.) Jeff Lieberman: The Investor:

  • What are Jeff's biggest observations on the current landscape given his seeing first hand the dot com bust and 2008? How is now different? How is it the same?
  • Price Sensitivity: How does Jeff reflect on his own price sensitivity? How has it changed over time?
  • Deployment Pace: How does Jeff analyse deployment pace today both for the industry and for Insight? Does Jeff agree with the notion of "playing the game on the field"?
  • The Biggest Miss: What have been some of Jeff's biggest misses? How did those misses impact the process with which he invests?

3.) Insight: The Firm

  • What are the most challenging elements of firm building today?
  • Why do all juniors have control over the Partners calendars? How does this work in practice?
  • How does Jeff create an environment of safety where very young, junior people feel like they can challenge anyone and have discussion?
  • How do Insight train young people? What is the process? What works? What does not work?

4.) AMA:

  • What does Jeff know now about venture that he wishes he had known when he started?
  • What would Jeff most like to change about the world of venture capital?
  • What advice does Jeff give to young people today entering the industry?

Item’s Mentioned In Today’s Episode with Jeff Lieberman

Jeff’s Favourite Book: Man's Search For Meaning

Jeff’s Most Recent Investment: Choco

Mar 25, 2022

Casey Winters is the Chief Product Officer at Eventbrite where he leads the PM, product design, research, and growth marketing teams. Prior to Eventbrite, Casey spent close to 3 years at Pinterest where he led the growth product team.

Andy Johns is one of the pre-eminent growth leaders of the last decade. Andy’s career started in growth at Facebook when the company scaled from 100M-500M active users. Since he has worked in some of the leading growth orgs at companies like Twitter, Quora and more recently at Wealthfront as Head of Growth and President.

Bangaly Kaba is the Head of Platform Growth @ Popshop Live, a live streaming mobile marketplace that combines commerce, entertainment, and social. Prior to Popshop, Bangaly led the product growth and consumer product orgs at Instacart and before Instacart was Head of Growth @ Instagram, where he built and led the product team that helped grow Instagram from 440M to > 1B monthly actives in 2.5yrs.

Elena Verna is a master when it comes to all things starting and scaling growth organizations. Previously, Elena spent over 7 years as SVP Growth @ SurveyMonkey where she ran product, growth marketing, and data teams. Post SurveyMonkey, Elena worked with the rocket ship that is Miro both as Interim CMO and as an advisor.

Ed Baker is an angel investor and growth advisor to various startups including Lime, Zwift, Whoop, Crimson Education, GoPeer, and Playbook. Ed was the VP of Product and Growth at Uber from 2013-2017. Prior to Uber, Ed was the Head of International Growth at Facebook.

Rob Schutz is Chief Growth Officer and Co-founder at Ro, the healthcare technology company building a patient-centric healthcare system. Under Rob’s growth leadership, Ro has become one of the fastest-growing companies in the country. Prior to Ro, Rob was VP of Growth at Bark, the makers of BarkBox, and helped scale revenue from zero to $100 million.

In Today’s Episode with Ed Baker You Will Learn:

1.) Casey Winters:

  • How does Casey define "growth"? How does it differ from product?
  • How do the best growth leaders decide between art vs science when making growth decisions?

2.) Andy Johns:

  • What is Andy's biggest advice to founders looking to build their first growth team?
  • What unexpected choice did Andy decide to make at Twitter that moved the needle for new user acquisition?

3.) Bangaly Kaba:

  • What were some of Bangaly's biggest takeaways from scaling Instagram from 440M users to 1BN?
  • What decisions did Bangaly make without data? How did they go? What did he learn?

4.) Ed Baker:

  • What are Ed's biggest takeaways from facebook around structuring growth teams?
  • What are Ed's biggest pieces of advice for startyups looking to grow internationally?
  • What were some of Ed's biggest learnings from working with Travis @ Uber?

5.) Elena Verna:

  • What is the difference between a good vs great growth model?
  • When does one need to change or amend their growth model? How does one know when it is working?

6.) Rob Schutz:

  • Why does Rob believe that startups should not diversify their customer acquisition channels too quickly?
  • How does Rob assess resouirce allocation and spend on new channels? How did this process look when partnering with the MLB for Ro?

Mar 23, 2022

Grant LaFontaine is the Founder & CEO @ Whatnot, the fastest-growing marketplace in the US, empowering people to make a living off their passion. To date, Grant has raised over $225M for Whatnot from the likes of CapitalG, a16z, YC, Scribble Ventures and Wonder Ventures to name a few. Prior to Whatnot, Grant was a PM @ Facebook working on the Oculus App Store and before that was the founder of Kit.com, ultimately acquired by Patreon.

In Today’s Episode with Grant LaFontaine You Will Learn:

1.) The Founding of Whatnot:

  • How did Grant make his way into the world of tech and startups?
  • What were some of his biggest lessons from Facebook? How did that impact how he has built Whatnot?

2.) Impossible To Hire Product Managers:

  • Why does Grant believe it is impossible to hire product managers today?
  • How does this impact the decision-making powers of engineers?
  • How does Grant test for this product knowledge in all engineers he adds to the team?
  • What are clear signals of 10x engineers in hiring processes?

3.) A/B Testing and Risk Mindset:

  • Why does Grant not believe in the effectiveness of A/B testing? Why does it not work?
  • Why does Grant believe one of the biggest reasons for startups failing is they do not take enough risk?
  • How does Grant try to ensure that his team takes as much risk as possible with everything that they do?
  • How does mindset to risk change with scale of company and with leadership?

4.) AMA:

  • Why does Grant disagree with founders angel investing?
  • What are the biggest challenges Whatnot has faced in scaling?
  • CEO coach? Who? When? What is the biggest lesson?
  • What is the single driving metric of Whatnot? How does Grant advise founders to determine their North Star metric?

Item’s Mentioned In Today’s Episode with Grant LaFontaine

Grant’s Favourite Book: Foundation: 1/3 (Foundation Trilogy)

Mar 21, 2022

Luciana Lixandru is a Partner @ Sequoia, one of the world’s most renowned and successful venture firms with Sequoia-backed companies accounting for more than 20% of NASDAQ's total value. As for Luciana, at Sequoia she has led investments in the likes of PennyLane, Xentral, Veed and Ledgy to name a few. Prior to joining Sequoia in 2020, Luciana was a Partner @ Accel where she made investments in Hopin, Miro, UiPath, Tessian and Deliveroo. As a result of such investing success, Luciana was #2 on the Midas List in 2021.

In Today’s Episode with Luciana Lixandru You Will Learn:

1.) Origins:

  • How did Luciana make her way from a small town in Romania to being Partner @ Sequoia?
  • What were the 1-2 crucible moments in her life that changed the course of her life?

2.) Luciana: The Investor

  • How has Luciana's investing style changed and developed over the years?
  • How does Luciana reflect on her own relationship to price? What misses caused these changes?
  • Hopin, Miro, Deliveroo, UiPath, how did having such winners so early impact Luciana's investing mindset?
  • What would Luciana say is her biggest insecurity today? What drives this?

3.) Sequoia: The Team

  • What are Luciana's biggest takeaways from working with Doug Leone, Alfren Lin, Roelof Botha and Pat Grady?
  • What does the decision-making process look like for new deals within Sequoia?
  • How does the Sequoia partnership create an environment of safety where everyone can discuss and debate freely?
  • How does Luciana approach training and mentorship? What works and what does not?

4.) Sequoia in Europe + Sequoia's Arc:

  • What is Arc? Why was now the right time for Sequoia to do it?
  • What is the structure for the program?
  • How many startups are part of it? Who is able to apply?
  • How much capital do the startups receive? What else do they receive in mentoring etc?
  • In 5 years time, what would success look like for Luciana with Arc?

Item’s Mentioned In Today’s Episode with Luciana Lixandru

Luciana’s Favourite Book: The Spy and the Traitor: The Greatest Espionage Story of the Cold War

Mar 16, 2022

Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and is one of the most popular newsletters on Substack. Lenny is also an extremely active angel investor with a portfolio including Figma, Sorare, Clubhouse, Vanta, WhatNot and many more incredible companies. If that was not enough, Lenny also has the best course on product management, check it out here.

In Today’s Episode with Lenny Rachitsky You Will Learn:

1.) Origins in Product:

  • How did Lenny make his way iunto the world of product management at Airbnb?
  • What were some of his biggest takeaways from his time at Airbnb on product?
  • What mistakes did he make on product at Airbnb? How did it impact his product thinking?

2.) Product Management: 101

  • How does Lenny define product management today? How is the role of PM changing?
  • When is the right time to hire your first PM as a startup?
  • What is the difference between Head of Product and CPO? When do you hire each?
  • What are the biggest mistakes founders make when hiring their first product hires?

3.) The Hiring Process:

  • How should founders breakdown the process of hiring for their first in product?
  • What does the interview process look like? How should founders structure it?
  • What core questions should teams ask of prospective candidates?
  • What are red flags when interviewing potential product hires?

4.) The Onboarding Process:

  • How should founders structure the onboarding process for new product hires?
  • What can founders do to make PMs successful in their first 30 days?
  • Where do many product hires make the biggest mistakes in the first 30 days?
  • What can product hires do to build trust with their new team?

Items Mentioned in Today's Episode with Lenny Rachitsky

Lenny's Fave Book: The Mom Test

Mar 14, 2022

David Friedberg is Founder and CEO of The Production Board (TPB), a holding company established to solve the most fundamental problems that affect our planet, by reimagining global systems of production. Prior to founding The Production Board, David founded The Climate Corporation, a 10-year journey that culminated in their $930M acquisition by Monsanto. If that was not enough, David is the Founder and Chairman at Metromile and also sits on the board of Soylent, Clara Foods, Tillable, Cana Technologies and more.

In Today’s Episode with David Friedberg You Will Learn:

1.) Origins:

  • How David made his way into the world of startups and technology from academia and physics?
  • What were David's biggest takeaways from scaling The Climate Corp to $930M exit to Monsanto?
  • How did the exit put pressure on David for all future companies he builds? How does he manage that?

2.) The Macro: Venture + The Economy

  • How does David foresee the impending rate hikes? What impact will this have on venture and the economy?
  • What segment of the market will be first to be hit? Why is growth investing last to be hit? How does early stage play out in this very new environment?
  • How will we see the velocity of capital deployment change in this new period? What does David believe are some of the crucial flaws of the venture model?
  • How does David reflect on his own price sensitivity? What lessons has he learned from deals he has done or missed that have changed his perspective?

3.) David Frankel: The Business Builder

  • What is David's rubrik for business value creation? How has this changed with time?
  • How mentally plastic does one have to be around the time it takes to see margins, unit economics etc change from negative to positive?
  • How does David and the team approach building new companies at TPB? Where do they find the founding teams? How do they incentivise them?
  • How does TPB approach continuous funding for the companies they create? What milestones need to be hit? How do they assess them?
  • How does David approach liquidity with regards to exits for the companies they create? Why does their holding company structure mean they have different incentives to VCs?

4.) David Friedberg: Father and Husband

  • How does David reflect on his own relationship to money today? How has it changed over time?
  • What have been David's biggest realisations on what provides him true happiness?
  • How did having children change his operating mentality? What does being a great father mean to David?

Item’s Mentioned In Today’s Episode with David Friedberg

David’s Favourite Book: Zen Mind, Beginner's Mind

Mar 11, 2022

Sid Sijbrandij is the Co-founder & CEO @ GitLab. GitLab’s single application helps organizations deliver software faster and more efficiently while strengthening their security and compliance. Prior to their IPO last year, Sid raised funding from some of the best including ICONIQ, GV, Tiger, Coatue and D1 to name a few. Under his leadership, the company has grown to over 1,500 employees and over 30 million registered users. If that was not enough, Sid is also an active angel and sits on the board of Meltano, a spinout of Gitlab that allows you to manage all the data tools in your stack.

In Today’s Episode with Sid Sijbrandij You Will Learn:

1.) The Founding of Gitlab:

  • How did Sid make his way into the world of tech and startups?
  • What was it about Gitlab as a project that excited Sid so much from Day 1?
  • How did Sid convince his co-founder to turn Gitlab from a project into a company?

2.) The Future of Work:

  • Why does Sid believe it is a fallacy that everyone will go back to the office?
  • What are the 1-2 most important things for companies to do when moving to a remote work environment? Where does Sid see many make mistakes?
  • What have Gitlab done to create a remote working environment so successfully? What have they tried that has not worked?
  • What stage of company building does remote work best for? When is it most challenging?

3.) Sid: The Leader

  • How has Sid changed and evolved as a leader over the Gitlab journey?
  • How does Sid look to get as much feedback as possible on his leadership?
  • How does Sid create an environment of safety where everyone feels they can provide feedback?
  • How does Sid work with his CEO coach? Should every CEO have one? What should one look for in them? How do you know when you need to change your CEO coach?

4.) Sid: The Board Member:

  • What have been Sid's biggest lessons on what makes successful board management?
  • In prep for the meeting, what materials does Sid provide? When does he send them? Does he present to the board? What mistakes do founders make in boards?
  • From being on the other side as a board member, what does Sid believe the best members do?
  • What would Sid most like to change about board meetings today?

Item’s Mentioned In Today’s Episode with Sid Sijbrandij

Sid’s Favourite Book: High Output Management

Mar 9, 2022

Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. In this role, Jeanne is responsible for all sales functions across the region including Sales Development, AEs, Solutions Architects, and many more. Jeanne also continues to spearhead Stripe's Enterprise strategy. Prior to this role, Jeanne was Stripe's Head of North America Sales where she built out Stripe's Acquisition Sales teams. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM.

In Today’s Episode with Jeanne DeWitt Grosser You Will Learn:

1.) Entry into Sales:

  • How did Jeanne make her way into her first sales job in tech?
  • What did Jeanne learn from her many years at Google about how sales should interact with engineering?
  • In hindsight, what would Jeanne have done differently/improved from her time with Dialpad?
  • How did the role with Stripe come about?

2.) The Playbook:

  • Does the founder need to be the one to create the sales playbook?
  • When is the right time to bring in the first sales hire? Should they be a sales leader or rep?
  • How does both the playbook and the type of sales hire change when hiring for a product-led-growth motion vs a traditional enterprise motion?
  • What are the single biggest mistakes founders make when hiring their first in sales?

3.) The Hiring Process:

  • How should founders structure the hiring process for their first sales hires?
  • What did Dialpad do in the sales hiring process that worked well? How has Jeanne taken that to her hiring process at Stripe?
  • What should be achieved or learned in each consecutive interview?
  • How can founders use sales case studies most effectively? How can founders know if sales candidates truly have a strong grasp of the product?
  • What are early signs of a 10x sales hire? What are red flags to look out for in the process?

4.) Sales Onboarding:

  • What does the ideal onboarding process look like for new sales hires?
  • What tasks and duties should all sales hires perform in the first 60 days?
  • What are early signs that a new hire is not performing to the right standard?
  • How does the first few months differ for sales reps when comparing a product-led-growth company to an enterprise company?
  • What should sales leaders do to ensure that new hires engage with product and customer success efficiently?

Mar 7, 2022

Harley Finkelstein is the President of Shopify, the platform modern commerce is built on. Over the last 12 years, Harley has partnered with Tobi to the tune of building Shopify's revenue to over $4.6BN in 2021 and the team to over 10,000 employees. On the side, Harley is an Advisor to Felicis Ventures and in the past has held board seats at CBC, Omers Ventures and The C100. If that was not enough, you can see Harley on a screen near you as one of the “Dragons” on CBC’s Next Gen Den.

In Today’s Episode with Harley Finkelstein You Will Learn:

1.) The Founding Story:

  • What was Harley's first entrepreneurial endeavour?
  • How did seeing his family lose everything impact Harley's mindset and ambition?
  • How did Harley first meet Tobi @ Shopify? How did the Shopify journey begin?

2.) Leadership Lessons:

  • How has Harley changed as a leader over the 13 years with Shopify?
  • How does Harley embrace vulnerability and authenticity in his communication with the team?
  • What is Harley most insecure about when he looks at leadership today?
  • What have been some of the biggest lessons Harley has learned from his board on what great leadership is?

3.) The Art of Marriage:

  • What does Harley believe makes the most successful marriage?
  • Why have Harley and his wife been seeing a marriage therapist from the early days?
  • What is the biggest mistake people make when communicating with partners?
  • How has Harley changed as a husband over the years?

4.) The Joy of Fatherhood:

  • Does Harley always believe he has been a good father?
  • What was his realisation moment that he was not being the father he wanted to be?
  • What core elements of his behaviour did he change? How did that impact his relationship with his kids?
  • How does Harley ensure he performs at the highest level while also being there and being present for his family?

Item’s Mentioned In Today’s Episode with Harley Finkelstein

Harley’s Favourite Book: The Book of Ichigo Ichie: The Art of Making the Most of Every Moment, the Japanese Way

Feb 28, 2022

Scott Dietzen is Vice Chairman of the Board of Pure Storage and served as the Company’s CEO from 2010 to 2017. Under his leadership, Pure grew to thousands of employees and
completed an IPO in 2015. Dietzen is a four-time successful entrepreneur with WebLogic, Zimbra, and Transarc. Before Pure, he was President and CTO of Zimbra (now part of VMware), but originally acquired by Yahoo!, where Dietzen served as interim SVP of Communications and Communities. Prior to Zimbra, Dietzen was CTO of BEA Systems, where he helped craft the technology and business strategy for WebLogic that drove BEA from $61m in annual revenues prior to the WebLogic acquisition to over $1B.

In Today’s Episode with Scott Dietzen You Will Learn:

1.) The Journey to Pure Storage CEO:

  • How did Scott make his way into the world of tech and startups?
  • What was the hardest element of making the transition from CTO to CEO?
  • What advice would Scott give to more technical leaders looking to make the move to CEO? Where do so many make mistakes?

2.) How To Build Trust in a Team:

  • What are the most important ways that leaders can build trust with their teams?
  • How can leaders be honest and share the hard truths without damaging role?
  • What is the right tone to communicate both the big wins and big losses?
  • Why does Scott always believe the losses teach more? How does Scott approach post-mortems?

3.) The Biggest Mistakes Founders Make:

  • What are the single biggest hiring mistakes that founders make?
  • What are the single biggest firing mistakes executives make?
  • Why should founders sometimes say no to customers?
  • How should founders approach investor selection and valuation for rounds?

4.) How to Optimise a Board:

  • What specifically can founders do to optimise their board?
  • What are the biggest errors founders make when communicating with their board?
  • What is the value per word framework? How does it tell which board member is the best?

Item’s Mentioned In Today’s Episode with Scott Dietzen

Scott’s Favourite Book: The 22 Immutable Laws Of Marketing

Feb 25, 2022

Sahil Bloom is the Founding Partner @ SRB Ventures, a $10M fund that leverages the 500K followers Sahil has amassed to invest at the intersection of venture and media. Previously, Sahil spent 7 years at a large investment fund managing >$3.5 billion in capital and serves on the board of 4 companies. He has also been an active angel investor in over 30 companies.

In Today’s Episode with Sahil Bloom You Will Learn:

1.) How Sahil made his way from a career in traditional finance to building a media company and leveraging that to raise the latest SRB fund? How does Sahil advise others is the best way to "find their zone of genius"?

2.) How To Build a Media Engine:

  • What have been some of Sahil's biggest lessons on what works on Twiter and what does not work?
  • What is the golden rule for Twitter?
  • How does Sahil plan and come up with ideas for his Twitter threads? What tools and software does he use? How long does each thread take?

3.) The End of the Road for Traditional Venture:

  • Why does Sahil think traditional venture is dying?
  • What newcomers will take the place of the existing incumbents?
  • Why does he think they are weak? What do new players provide that they do not?
  • Which existing players will remain and be strong? Which will fade out?
  • Does Sahil believe that VCs really provide any value?

4.) SRB Ventures:

  • Why did Sahil decide to raise the new fund?
  • How did he decide on size of the fund? What is the strategy? What is the portfolio construction?
  • How does SRB provide media services others do not?
  • How did Sahil meet Tim Cook and get him to invest in the fund?
  • What is the biggest thing Sahil believes most people misunderstand about luck?

Item’s Mentioned In Today’s Episode with Sahil Bloom

Sahil’s Favourite Book: When Breath Becomes Air: Kalanithi Paul

Sahil’s Most Recent Investment: Wander

Feb 23, 2022

Tiger Global are one of the most discussed venture firms on the planet. With a deal cadence and capital deployment speed that is unmatched, they have made their mark on the venture landscape like no other over the last 24 months. Today we are joined by leaders from Sequoia, Benchmark, Thrive Capital, General Atlantic, GGV and Aleph to discuss the rise of Tiger and how it impacts the venture ecosystem.

In Today’s Episode on Tiger Global You Will Learn:

1.) Doug Leone: Sequoia Capital

  • Why we need to change the words when use in venture? Why we need to get rid of "the game"?
  • How does the rise of Tiger compare to the rise of prior entrants with the same approach?
  • Why does Doug believe that the craft of venture will persist despite these new entrants?

2.) Bill Gurley: Benchmark Capital

  • How does Bill analyse the change in late stage venture today?
  • What are the main drivers of the increased competition in late stage venture?
  • Why does Bill get concerned not by Tiger but how others respond to Tiger's model?
  • How does Bill analyse the entry of hedge funds and PE funds into traditional venture models?

3.) Michael Eisenberg: Aleph

  • How does Michael think about the "weaponisation of capital"?
  • What are the significant benefits for a fund of having more capital than their competitors?
  • How does this capital advantage change in boom and bust times?

4.) Anton Levy: General Atlantic

  • Why does Anton believe that funds are leveraging their assets more efficiently than ever?
  • How does Anton approach the mindset of AUM scaling without lowering returns?
  • Why does Anton never want to compete on price?
  • How does GA think about competing in a world of Tiger and hedge funds investing in tech?

5.) Hans Tung: GGV

  • Why did Hans always believe the model to look at moving forward was Tiger?
  • Why does Tiger's business model allow them structural and financial advantages over their competitors?
  • What does Hans make of the data network effects of Tiger with their strategy?

6.) Kareem Zaki: Thrive Capital

  • Why does Kareem think Tiger's approach makes absolute sense?
  • Why does Kareem believe so many in venture like to try and discredit the Tiger model?
  • How does Tiger's approach differ to Thrive's?

Feb 18, 2022

Max Rhodes is the Co-Founder and CEO @ Faire, the online marketplace where retailers discover their next bestsellers from independent brands across the globe. To date, Max has raised over $1.1BN with Faire from some of the best including Sequoia, Founders Fund, DST, Forerunner, Lightspeed and many more. Prior to starting Faire, Max spent close to 5 years at Square in numerous different roles including Director of Consumer Product at Caviar.

In Today’s Episode with Max Rhodes You Will Learn:

1.) The Founding Story:

  • How Max made his way into the world of startups with his joining an early Square team?
  • How did his 5 years at Square impact how he approaches company building with Faire?
  • How did Square's approach to product and mission impact Max's thinking?

2.) How To Hire Effectively:

  • How does Max construct the hiring process? Where do many founders make mistakes?
  • What does Max mean by "deep behavioural interview"? What questions does he ask?
  • What are the signals of 10/10 candidates? What are red flags he looks for?
  • How does Max determine capability? What literal tests can be done to test for this?

3.) How To Reference People:

  • How does Max approach the referencing process when hiring people?
  • How does Max make the other side feel comfortable, so they will open up and share everything?
  • What have been some of Max's biggest lessons on what it takes to do referencing well?
  • Where do many make mistakes with referencing?
  • How does Max use an "out of 10" system to determine the quality of the candidate?

4.) How to Strategise:

  • How does Max use strategy docs to orient the direction of the company?
  • How often does Max write them? How long do they take to write?
  • What are the core components of the strategy docs?
  • Who else is involved in their writing? Once written, what is the right format to discuss with the team?
  • How does Max approach how rigid he is to the strategies outlined? How does he determine whether he should change strategy or stick to plan?

Item’s Mentioned In Today’s Episode with Max Rhodes

Max’s Favourite Book: Good Strategy Bad Strategy, Who: The A Method for Hiring

Feb 16, 2022

Ed Baker is an angel investor and growth advisor to various startups including Lime, Zwift, Whoop, Crimson Education, GoPeer, and Playbook. Ed was the VP of Product and Growth at Uber from 2013-2017. Prior to Uber, Ed was the Head of International Growth at Facebook, a company he joined after they acquired a startup he co-founded called Friend.ly, which had grown to over 25 million users.

In Today’s Episode with Ed Baker You Will Learn:

1.) Ed Baker: Entry into Growth:

  • How Ed made his way into the world of growth from his start founding a dating site while at Harvard?
  • How he made his way to lead international growth at Facebook? How his time with Facebook led to his joing Uber to start Uber's growth team?
  • What were Ed's biggest lessons from Uber and Facebook? How did his approach to growth and mindset change as a result of his time there?

2.) When is the Right Time:

  • When is the right time for startups to hire their first growth leads or reps?
  • How should they determine whether to promote from within or hire externally?
  • What are the biggest mistakes startups make on the timing of this hire?
  • How can startups accurately assess whether they have product-market-fit?

3.) Who To Hire:

  • Step by step, how does Ed structure the interview process for all new growth hires?
  • What are the must ask questions for growth leaders to ask candidates in interviews?
  • What are the clear signs and answers that suggest a 10x growth hire?
  • What literal tests does Ed do to determine the quality of a hire? How do the best perform?

4.) Onboarding and Integration:

  • What is the optimal onboarding process for all new growth hires?
  • How do the best growth hires start in the first 60 days? What do they achieve?
  • What are some of the early signs that a growth hire is not working out?
  • How should the relationship be between the CEO and the Head of Growth?
  • How can the Head of Growth foster a strong relationship between growth and product teams?

Feb 14, 2022

Geoff Lewis is the Founder and Managing Partner @ Bedrock, now with over $1BN in AUM, Bedrock invests in breakout technology companies that are incongruent with popular narratives. In the past, Geoff has backed some generational defining companies such as Wish, Lyft, Nubank, RigUp, Vercel, Anduril and many more. Prior to founding Bedrock, Geoff was a Partner @ Founders Fund.

In Today’s Episode with Geoff Lewis You Will Learn:

1.) How Geoff made his way into the world of venture with his joining Founders Fund? How his time with Founders Fund led to his co-founding Bedrock with Eric?

2.) Geoff Lewis: The Investor:

  • How does Geoff reflect on his own relationship to price? How does he determine when to pay up vs walk away?
  • How does Geoff approach the re-investment decision-making process? Where do most go wrong when it comes to allocating reserves?
  • What have been some of Geoff's biggest misses? How did they impact his investing mindset?
  • Why does Geoff not believe that ownership is as crucial as other VCs suggest?

3.) Bedrock: The Firm

  • What have been some of the biggest challenges in building Bedrock?
  • Where does Geoff believe many firms make core mistakes in firm building?
  • What are the differences between principles and rules? Why does Geoff believe all firms need to have principles?
  • How does Geoff approach internal talent building? What are the signals of people that will succeed in venture? How do they approach learning?

4.) The Market:

  • How does Geoff analyse the current state of the venture market?
  • Does Geoff agree with the notion of "play the game on the field"?
  • Why does Geoff think markups are BS and just VCs looking for external validation?
  • How has Geoff learned to isolate from the VC community and retain that purity of mindset working with great entrepreneurs?

Item’s Mentioned In Today’s Episode with Geoff Lewis

Geoff’s Favourite Book: Friedrich Nietzsche

Geoff’s Most Recent Investment: Praxis

Feb 11, 2022

Aaron Levie is the Founder and CEO @ Box, the company incorporating the best of secure content collaboration with an intuitive user experience suited to the way people work today. Prior to their IPO in 2015, Aaron raised from some of the best in the business including the main man Mark Cuban, a16z, Emergence, DST, Coatue, DFJ and many more. Aaron founded the company from his dorm room at the University of Southern California and has led the company to 1,900 employees and over $770M in revenue, as of 2021 data.

In Today’s Episode with Aaron Levie You Will Learn:

1.) How Aaron founded Box from his dorm room at the University of Southern California? What was that founding a-ha moment? What did the first year look like? Does Aaron agree, "serial entrepreneurship is overrated"?

2.) Phases of Leadership and Company Growth:

  • How does Aaron define the different phases of leadership required as a company grows?
  • Which phase did Aaron find the most challenging? How did he overcome it?
  • What are the first things to break when companies grow? What can founders do to prevent this?
  • Does Aaron agree, "the best CEOs are the best resource allocators"?

3.) The Market:

  • How does Aaron thinkj about the dislocation between private company valuations and public company market caps?
  • What does Aaron believe are the biggest challenges founders face when they are over-capitalised?
  • What does Aaron mean when he says, "raise when cash is cheap, spend as if it was expensive"? How does Aaron advise founders on fundraising today?

4.) The Team and Culture:

  • How does Aaron create a safe space where all team members can come to him with anything?
  • How does Aaron approach effective goal setting? How does one balance between achieveable and also aggressive goals?
  • How does Aaron approach the art of delegation? What is his decision-making framework for what to delegate vs what to control?

Item’s Mentioned In Today’s Episode with Aaron Levie

Aaron’s Favourite Book: Innovator's Dilemma: When New Technologies Cause Great Firms to Fail (Management of Innovation and Change)

Feb 9, 2022

Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, the leading online platform for the creative industry, and served as CEO until Adobe acquired Behance in 2012. Behance now has over 25M members. Scott is also an early advisor and investor in Pinterest, Uber, Sweetgreen, Carta, Flexport, Airtable, and several others. Finally, if that was not enough, Scott is the author of two national bestselling books - Making Ideas Happen and The Messy Middle.

In Today’s Episode with Scott Belsky You Will Learn:

1.) Narrow the Focus, Increase the Quality:

  • What does Scott believe is the core challenge in product?
  • What was the single biggest product challenge Scott faced at Behance? How did they overcome it?
  • When should product teams listen to customer feedback vs ignore it?
  • What are the core questions product teams should ask user groups to extract the most feedback and value?

2.) The Importance of the First Mile:

  • What does Scott believe makes a great first mile when it comes to the product experience?
  • Where do so many companies go wrong in creating the first mile user experience?
  • Which company at scale has retained this simplicity of the first mile? How did they do it?
  • What does Scott mean when he says, "the devil is in the defaults"? What can product teams learn from this?

3.) The Makings of a Great Product Leader:

  • What are the 3 core questions every great product leader should ask on every screen?
  • How do the best product leaders structure product reviews?
  • Who is invited to product reviews? How often are they? Who sets the agenda? When is it sent?
  • What do the best product leaders do to retain direction and productivity in reviews when there are many people and many ideas? How do they stay on track?

4.) The Hirings of a Great Product Team:

  • How can founders know whether to hire the product leader or retain the role? When is the right time?
  • What are the single biggest mistakes founders make when hiring their first product hires?
  • How should founders structure the hiring process for product hires? What should they look to gain from each interview?
  • What are the must ask questions in those interviews? How do the best respond?
  • What case studies or physical tests can be done to determine the quality of a candidate?

Feb 7, 2022

David Frankel is a Co-Founder and Managing Partner @ Founder Collective, one of the great seed firms of the last decade with a portfolio including Uber, Coupang, Airtable, Whoop and many more incredible companies. Previously, David was Co-Founder and CEO of Internet Solutions (IS), the largest ISP in Africa, ultimately acquired by NTT. David is also a founding board member of Endeavor SA and in the past has been selected by the World Economic Forum for the Global Leader of Tomorrow (GLT) program.

In Today’s Episode with David Frankel You Will Learn:

1.) How David made his way into the world of angel investing? How his mindset changed when making the transition from angel to an institutional investor with the founding of Founder Collective?

2.) Building the Firm: Founder Collective

  • What are the biggest challenges in venture firm building today?
  • Why is "deploy" and "the game" banned as words within Founder Collective? What terms are promoted as an alternative?
  • How does David construct investment decision-making in the partnership?
  • How does David create a safe space where all team members can share their thoughts in a non-judgemental, safe environment?
  • What are the biggest mistakes or challenges that David sees firms make when building?

3.) David Frankel: Investor Mindset

  • How does David analyse the current seed market today? What does he like? What worries him?
  • Does David agree that early stage investing has never been less collaborative?
  • How does David reflect on his own relationship to price today? How does he determine when to pay up vs when not to?
  • How does David think about the compression on fund deployment timelines? Will this change?
  • How does David keep a fresh and clean mind when viewing new opportunities, having seen many work and not work? How does one retain that mental purity when investing?
  • What have been some of David's biggest misses? How did it impact his style of investing?

4.) The Partnership:

  • What was the most recent disagreement David had with the partnership? How was it resolved?
  • How does David approach self-doubt and insecurity within the partnership? How can this be managed successfully?
  • What have been some of David's biggest lessons on how to give effective feedback without being judgemental?
  • In a world of Zoom, how did the partnership retain the same level and quality of connection that they had in person? What works? What does not work?

Item’s Mentioned In Today’s Episode with David Frankel

David’s Favourite Book: The Code Breaker: Jennifer Doudna, Gene Editing, and the Future of the Human Race

David's Most Recent Investment: PairTree

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