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 for more information on the podcast, show notes, resources and more.
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Now displaying: 2023
Dec 22, 2023

Dave Powers serves as President and CEO of Deckers Brands, a global footwear and apparel company where he focuses on the company’s five high-performing brands: UGG®, Teva®, Sanuk®, HOKA One One® and Koolaburra®. Prior to Deckers, he held executive leadership roles at Converse and Timberland, where he led worldwide retail merchandising, marketing, visual and store design as well as the creation of a sustainable line of footwear and apparel.

In Today's Episode with Dave Powers:

1. The Unlikely CEO of a Global Footwear Company:

  • How did Dave make his way into the world of consumer and fashion from the ground up?
  • Why did Dave never think he was the type of person to be a CEO?
  • What does Dave know now that he wishes he had known when he started his career?

2. From $1.1M Acquisition to $1.4BN Revenues: The Hoka Story:

  • Why did Deckers acquire Hoka for $1.1M? What did they see in this, at the time, futuristic running shoe that no one else saw?
  • Was the growth of Hoka linear or were there needle-moving moments that propelled the brand?
  • What did they do so right that led to their success?
  • What would Dave have done differently in the Hoka journey if he had his time again?

3. From $14.7BN Acquisition to Oprah's Favourite: The UGG Journey:

  • How much of a needle mover was it for UGG when Oprah added it to her list of favourite items?
  • Why did UGG go through a tough period? What did they do wrong?
  • What does it take to resurrect a brand? How can they bring UGG back to life and make it cool?

4. From Abercrombie to LVMH: An Analysis of the Industry:

  • How does Dave analyse the rise and fall of Abercrombie and Hollister? Where did it go wrong?
  • What does Dave believe LVMH are the best in the world at? What does he learn from them?
  • How important is it for consumer companies to have a hero product?
  • How can consumer companies scale to mass markets without losing their core audience?

Dec 20, 2023

Gustav Söderström is the Co-President, CPO & CTO at Spotify. Gustav has been instrumental in taking Spotify from a 30-person operation in Sweden when he joined to being the global leader of the space.

Scott Belsky is 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. 

Tomer Cohen is the Chief Product Officer @ Linkedin where he is responsible for setting and executing the global product strategy at LinkedIn.

In Today's Episode on How AI Changes The Future of Product and Design We Discuss:

1. Why AI Is Now the Product that UI Serves:

  • Why does Gustav believe that AI is now the product?
  • How has the importance of UI changed with the rise of AI?
  • How did TikTok change the product paradigm over the last few years?

2. What Matters More Models or Data:

  • What is more important the size of the model or the amount of data a company has?
  • Will companies use many models at the same time?
  • Why will companies using many models at once create a huge opportunity for startups?
  • Will every company have their own model? What will be the decision-making framework of whether to have your own model or leverage another?
  • How does the rise of AI change how companies approach data acquisition, collection and cleaning?

3. The Workforce Needs to Change with AI:

  • How do product leaders and teams need to change in an AI-first world?
  • What do designers need to do to stay up to date in an AI-first world?
  • What does it mean to be good at prompting? How can people get good at prompting?
  • Why will AI kill companies that charge by the hour?
  • Why will seat pricing die in a world of AI? What will be the business model for AI?

4. Incumbents vs Startups: Who Wins:

  • Do incumbents win in a world of AI or do startups?
  • Why is AI primed for incumbents to win and move fast in a way they could not in prior technology cycles?
  • What are the biggest hurdles and challenges incumbents have to face that startups do not?
  • What are the biggest barriers that startups have to win in a world of AI that incumbents do not have?

Dec 18, 2023

Peter Lacaillade is a Managing Director @ SCS Financial Services where he leads its private investment program where he oversees the firm’s activities in private equity, opportunistic credit and private real assets. Peter has been an early backer of Thrive, Founders Fund, a16z, Greenoaks and 20VC. Before SCS, Peter was an Associate at HarbourVest Partners in its Secondary Group where he analyzed venture capital, growth equity and buyout investments.

In Today's Episode with Peter Lacaillade We Discuss:

1. Becoming One of the Great LPs in Venture:

  • How did Peter make his way into the world of fund investing as an LP?
  • What does Peter know now that he wishes he had known when he started as an LP?
  • Why does Peter believe now is the best time to be investing in newer, emerging managers?

2. How to Pick the Best Venture Managers:

  • What are the commonalities in the best VCs Peter has invested in?
  • How important is track record for Peter when evaluating managers?
  • What mistakes has Peter made when it comes to manager selection? What did he learn?
  • How do the best managers build relationships with their LPs?

3. Building a Portfolio That Can 5x:

  • In a venture fund portfolio, what is the distribution between those that outperform, perform as planned and then underperform?
  • How does Peter invest in both large franchises and emerging managers with a barbell approach? How much in established franchises and how much in emerging managers?
  • Are managers actively marking down their portfolios in the last 18 months? Who has been the best at this and who has been the worst? How much should portfolios be marked down?
  • How does Peter evaluate the compression of deployment timelines we saw in the last 18 months?

4. A Breakdown of the LP Landscape:

  • Family Offices: What are the biggest dangers of having family offices as LPs? Why do multi-family offices tend to be better?
  • Endowments: Are they really as stable as people think they are? What separates a good vs great endowment? Who stands out?
  • Fund of Funds: Why does Peter think fund of funds deserve more credit? How should managers think about working with FoFs most effectively?
  • What is the right level of concentration managers should have between these different LP profiles?
  • What are the biggest mistakes emerging managers make when approaching LPs?

Dec 15, 2023

Davis Smith is the Founder and Chairman of Cotopaxi, an outdoor brand with a humanitarian mission. The company has assisted over 4 million people living in poverty. The company has been profitable for the last 4 years and is expected to do $160M in revenue in 2023, up from $55M just two years before. In April 2023, Davis resigned after 10 years as CEO to lead a mission for his church in Brazil for three years. Davis is an EY Entrepreneur of the Year and was recognized as Utah’s Businessperson of the Year in 2022. He is an adventurer who has floated the Amazon on a self-made raft, kayaked from Cuba to Florida, and explored North Korea.

In Today's Episode with Davis Smith We Discuss:

1. From Selling $6M Worth of Pool Tables to the Amazon of Brazil to Founding Cotopaxi:

  • How did Davis scale a pool table business to $6M in revenue?
  • What were Davis' biggest takeaways from building the Amazon of Brazil, raising millions in VC funding and the business failing?
  • How did depression and 36 hours on a sofa lead to the a-ha moment for Cotopaxi?

2. The Billion Dollar Company, Rejected by 100 Investors:

  • How was the early fundraising journey for Davis with Cotopaxi? Why did so many investors say no?
  • What was the best VC meeting he has ever had? Why do women understand Cotopaxi better?
  • What does Davis believe are the biggest misalignments between VCs and Founders?
  • Why does Davis believe we need a new type of financial product to fund long term projects?
  • What are the biggest elements of fundraising that Davis believes founders do not understand?

3. Scaling Cotopaxi to $150M in Revenue:

  • What are Davis' biggest lessons on what works and what does not from scaling Cotopaxi to $150M in revenue?
  • Why did Davis not lay anyone off but decide everyone should take a pay cut instead? How did that go down?
  • Why does letting people leave work earlier lead to better talent wanting to join your company?
  • Why does Davis believe that you absolutely can build a huge business with balance in your life?

4. Life, Parenting, Marriage:

  • Why does Davis believe that so many entrepreneurs chase the wrong thing? What do they chase? What should they be chasing instead?
  • How does Davis analyze his relationship to money today? Does it make you happy?
  • What does great parenting mean to Davis? How has that changed over time?
  • How does marriage change when comparing pre-kids and post-kids?
  • Was Davis nervous about becoming a father for the first time at the age of 24?

Dec 13, 2023

Steve Goldberg is the Chief Revenue Officer at Salesloft, the sales engagement platform that was acquired by Vista in 2022 for $2.3BN. Prior to Salesloft, Steve was Group Vice President of Enterprise at Yext and before that was a Senior VP @

In Today's Episode with Steve Goldberg:

1. Becoming a Sales Leader:

  • When did Steve first fall in love with sales?
  • Why does Steve believe sales is more psychology than anything else? What can sales reps do to master the psychology of their prospects?
  • What does Steve know now about sales that he wishes he had known in the beginning?

2. How to Close Prospects Faster Than Ever:

  • How does Steve build relationships with prospects very fast? What questions does he ask?
  • How does Steve know if he is really speaking to a buyer? What are the signals?
  • How does Steve advise sales reps on getting multiple relationships within an account to prevent the potential of losing your champion?
  • How does Steve feel about discounting? When is the right time to do it?

3. How To Do The Best Deal Reviews:

  • What makes good vs great deal reviews? Who is invited? Who is not?
  • Who sets the agenda? Who is responsible for what?
  • How do deal reviews change throughout the quarter and throughout the year?
  • Is a deal slipping into the next quarter an acceptable excuse for a sales rep to give?

4. How to Ensure Renewals in a World When They are Not Guaranteed:

  • Have all budgets centralized back to the control of the CFO?
  • Are people right to say that no CFOs are buying new technology today?
  • What is the best way to show to customers the value you provide?
  • Why does Steve believe revenue operations is the most valuable role within an org?

Dec 11, 2023

Sam Corcos is the Co-Founder & CEO @ Levels, the company helping you see how food affects your health with data from biosensors like continuous glucose monitors (CGMs). To date, Sam has raised over $89M for Levels from the likes of a16z (Jeff Jordan sits on his board), Founder Collective, Breyer Capital and Shrug Capital to name a few. Prior to Levels, Sam founded two prior companies, CarDash; a Y Combinator company that makes automotive repair and maintenance convenient. Before Cardash, Sam founded, Sightline Maps, an intuitive platform for 3D printing and visualizing topographical maps, marketed primarily towards the U.S. military.

In Today's Episode with Sam Corcos:

1. The Founding Moment:

  • What was the a-ha moment for Sam with the founding Levels?
  • What were the big mistakes Sam made with prior companies that he did not take with him to Levels?
  • What does Sam know now that he wishes he had known when he started Levels?

2. How to Fundraise Like a Pro:

  • Why does Sam believe that founders should take as many meetings with VCs as possible?
  • What are the biggest mistakes founders make when meeting investors?
  • Should founders meet with associates in the fundraising process?
  • What does Sam mean when he says, "you have to create theater" when pitching?

3. How to Extract the Most Value from Your Investors:

  • What have been Sam's biggest lessons on how to put your investors to work?
  • What is the right and most strategic way to ask investors for specific help?
  • How can founders create a competitive environment where VCs are competing to help?
  • Which investors have been the most helpful?
  • Why are post-IPO operators the best angels to have as investors?
  • How has the a16z platform team been such a needle mover?

4. How to Find Your Partner and Master Parenting:

  • What does Sam mean when he says he had a "one pager" in what he wanted in a partner?
  • What was in the one-pager? How did dates respond?
  • What are the biggest mistakes people make when dating?
  • What is Sam most nervous about on becoming a parent?
  • How does Sam think having a child will impact his marriage?

Dec 8, 2023

Sanjit Biswas is the Founder and CEO @ Samsara, allowing businesses that depend on physical operations to harness Internet of Things (IoT) data. Over the last 8 years, Sanjit has scaled Samsara to $1BN in ARR and a public company with tens of thousands of customers. Before Samsara, Sanjit was the CEO and co-founder of Meraki, one of the most successful networking companies of the past decade. Sanjit grew Meraki from his Ph.D. research into a complete enterprise networking portfolio. Meraki's sales doubled every year from inception and in 2012, Cisco acquired Meraki for $1.2 billion. Huge thanks to Doug Leone for some fantastic question suggestions pre this episode.

In Today's Episode With Sanjit Biswas We Discuss:

1. From Founding to $1BN in ARR in 8 Years:

  • What was the founding a-ha moment for Sanjit with Samsara?
  • Sanjit sold his prior company Meraki for $1.2BN, what worked with Meraki that Sanjit took with him to Samsara? What did not work that he left behind?
  • What does Sanjit know now that he wishes he had known when he started Samsara?

2. The Man Who Found Product Market Fit Time and Time Again:

  • What is the one single moment that Sanjit believes you know you have product market fit?
  • What are the biggest mistakes founders make when chasing product market fit?
  • How does being a bootstrapped company change how a company approaches chasing PMF?

3. Mastering a Multi-Product Company:

  • How do you know when it is the right time to launch a second product?
  • Does the second product have to make the first product better?
  • What are the biggest mistakes companies make when going multi-product?

4. The Art of Great CEOship:

  • Does Sanjit believe that the best CEOs are the best capital allocators?
  • What has been the single best and single worst capital allocation decision in Samsara's journey?
  • What are the biggest mistakes Sanjit has made in leadership? How did he learn and grow from them?

Dec 6, 2023

Geoff Charles is the VP of Product at Ramp, leading the product management, operations, and support teams. Prior to Ramp, Geoff helped spin off Mission Lane and scale credit products to millions of consumers. He started his career advising Fortune 100 financial services companies.

In Today's Episode with Geoff Charles We Discuss:

1. How to Become a Product Leader:

  • How did Geoff make his way into the world of product?
  • What are the single most important skills for product people to learn early?
  • What are the biggest mistakes that product people make early in their career?

2. When and Who to Hire for the First Product Team:

  • When is the right time to hire your first product people outside of founding team?
  • Why are the best product teams in the early days professional services teams?
  • What is more important; the person has stage or sector experience, when joining?
  • Should you hire senior product people or junior product people as the first hires?

3. How to Increase Velocity Using Sprints:

  • How does Geoff and Ramp use two-week sprints to have insane product velocity?
  • How are they structured? How are goals set? Who is included?
  • What makes a good vs a bad sprint? How is accountability tied to sprints?
  • When do two-week sprints no longer become possible? What happens then?

4. Going Multi-Product, Will Incumbents Kill You and Product Re-Usability:

  • When is the right time to add a second product?
  • What are the biggest mistakes companies make when going multi-product?
  • Why is it unlikely that an incumbent is the one to kill you? What competitor should worry you?
  • What does Geoff mean when he speaks of "product re-usability"? Why is it crucial to velocity?

Dec 4, 2023

Tooey Courtemanche, Jr. is the Founder, CEO, President, and Chairman of the Board of Procore. He founded Procore in 2002 with a mission to connect everyone in construction on a global platform. After 13 years of business, the company had just $9.6M in revenue, 8 years after that they have over $890M in revenue. Under his leadership, Procore has grown to become a leading global provider of construction management software, connecting over 2 million users across 150+ countries. Today Procore trades on the New York Stock Exchange under the ticker PCOR. Huge thanks to Brian @ Bessemer and Will @ Iconiq for some amazing question suggestions today.

In Today's Episode with Tooey Courtemanche:

1. The Founding of a $8.5BN Company:

  • How did Tooey's wife, Hilary and their house-building lead to the idea for Procore?
  • What does Tooey know now that he wishes he had known when he started?
  • Did Tooey always know he would be a success? What was the moment of most doubt?

2. The 13-Year Journey to $9.6M in Revenue:

  • Why did it take so long to hit the $10M revenue mark? What changed in 2015?
  • What is Tooey's biggest advice to founders and investors who face market timing risk?
  • Why was Tooey laughed out of VC offices in 2008? What are his biggest pieces of advice to founders raising from VCs today?
  • How does Tooey advise founders on the balance between vision and sticking to a mission vs realising when it is not working and giving up?

3. The Art of Great CEOship:

  • What advice did Tobi @ Shopify give Tooey on being a great CEO? How did it impact his approach?
  • What are the biggest differences between the reality of being a CEO and the Instagram version?
  • What have been Tooey's biggest lessons on hiring? Why does hiring smart, ambitious but not humble people never work?
  • Why does Tooey believe the idea of "becoming an entrepreneur" to be BS?

4. Parenting, Money and Marriage:

  • Why does Tooey believe great parenting is like great CEOship?
  • How does one bring up children to be ambitious and humble in a very privileged upbringing?
  • What are the secrets to being there as a husband while also being a rockstar CEO?
  • How does Tooey reflect on his own relationship to money and wealth today?

Dec 1, 2023

Dominik Richter is the Founder & CEO @ HelloFresh, one of the largest direct-to-consumer businesses of the last decade and the #1 recipe box delivery service. Fun fact, two of the three biggest cooking facilities in North America are HelloFresh facilities with the third being Disney World Orlando. Dominik has made over 40 angel investments in the EU and the US.

In Today's Episode with Dominik Richter We Discuss:

1. The Founding of One of the Largest D2C Companies:

  • How did Diminik's dreams of being a footballer translate to founding HelloFresh?
  • What does he know now that he wishes he had known when he started?
  • Why does Dominik respect the brands that large banks have built?

2. To Raise or Not to Raise:

  • Why does Dominik believe when you raise VC, you either have to sell or go public?
  • What are the single biggest differences between raising in the US vs Europe?
  • What are Dominik's biggest pieces of advice to founders raising today?
  • Why does Dominik believe so many of the D2C companies should not have raised venture funding?

3. The IPO: When, How and Why:

  • Why did Dominik decide to IPO the business so early?
  • Why does Dominik believe that the first-day trading price is irrelevant?
  • Why does Dominik believe that timing is so important when going public?
  • What are the biggest pros and cons of being public?

4. The Rise and Fall of D2C:

  • D2C has been crushed lately, why? Is this the end of D2C as a category?
  • Is D2C an investable category for VC? HelloFresh is one of the biggest and $2.5BN market cap?
  • What have been the best and worst resource allocations Dominik has made?
  • Do recessions help or hurt recipe box businesses?

Nov 29, 2023

Guillaume Cabane is a growth advisor to high-growth SaaS Startups, including Ramp, Spot, Airbyte, G2, Gorgias, Metadata, Madkudu, and others. Guillaume held VP of Growth roles at Drift, Segment, and other successful startups, where he helped them grow from ~50 to 300. Prior, Guillaume spent 6 years at Apple.

In Today's Episode with Guillaume Cabane We Discuss:

1. Entry into Growth:

  • How did Guillaume make his way into the world of growth?
  • What are 1-2 of his biggest lessons from him time at Segment where he 4x revenue?
  • What does Guillaume know now that he wishes he had known when he entered growth?

2. Enterprise vs SMB & CAC/LTV:

  • Why does Guillaume think it is harder to go enterprise down than SMB up?
  • What are the biggest mistakes companies make when scaling into enterprise?
  • What are the biggest mistakes startups make with product-led-growth motions?
  • Why does Guillaume believe it is impossible to analyse CAC/LTV in early companies?

3. Activation, Engagement and KPI Setting:

  • What are the biggest mistakes companies and teams make in activation?
  • What can growth and marketing teams do to guarantee engagement in prospects?
  • Why are all KPIs not tied to revenue BS?

4. Hiring the Growth Team:

  • What are the core characteristics of great growth hires?
  • How quickly does it become apparent when you have made a bad growth hire?
  • Why do founders make the best profiles when hiring your first growth hire?
  • What are the biggest mistakes Guillaume has made when hiring for growth?

5. Why Growth is Like Venture:

  • What is the secret to building a great growth portfolio?
  • Why is it impossible to scale to $50M ARR with only one good channel?
  • What is the right way to spread resources across channels?
  • When is the right time to add new channels and diversify?

Nov 27, 2023

Keith Rabois is a General Partner @ Founders Fund, one of the world's best venture funds with a portfolio including the likes of Facebook, SpaceX, Anduril, Tesla and many more. For the last 23 years straight, Keith has either invested in or founded a $BN company. Keith is also the Co-Founder and CEO @ Openstore, the company that will buy or run your Shopify business.

Mike Shebat is the Founder and CEO @ Traba, the company providing industrial staffing when and where you need it. To date, Mike has raised $49M with Traba from some of the best including Founders Fund, General Catalyst and Khosla Ventures.

In Today's Episode We Discuss:

1. What it Takes to Build a Great:

  • Why does Mike expect everyone to work in office 12 hours per day, 4 days per week?
  • At what point does an extra hour of work not lead to more output?
  • What are the expectations in terms of emails, out of office, the weekends?
  • Keith, from the 23 BN companies you have worked with, is this insane work ethic aligned to all of them? Which had it? What did not?
  • What core components of PayPal's work ethic made it so strong? What does Keith mean when he says Linkedin could and should have been 5x bigger?

2. The Hiring Process for the Swat Team:

  • What does the hiring process look like for this type of work environment?
  • What are the signs that someone is really aligned to it vs faking it for the interview process?
  • What have been Keith's biggest lessons on both compensation and title in the hiring process?
  • Why does Keith believe that culture is like concrete? What are the biggest mistakes he has made on culture and what would he have done differently?

3. First-Time Founders, Innate Entrepreneurs & Europe's Failing:

  • Does Keith agree the best founders always show signs of early entrepreneurship in their teens?
  • Why does Keith prefer first-time founders to serial entrepreneurs? Why are they better?
  • Why does Keith believe that Europe has not created a $100BN company since 1990?

4. Remote Work, Network Effects and Baseball:

  • Why does Keith believe being great in venture is like baseball?
  • Why does Keith and Founders Fund not invest in remote teams? How does he explain Gitlab?
  • Why does Keith believe Airbnb has the best network effect he has ever seen?

Nov 24, 2023

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support.

Yann LeCun is VP & Chief AI Scientist at Meta and Silver Professor at NYU affiliated with the Courant Institute of Mathematical Sciences & the Center for Data Science. He was the founding Director of FAIR and of the NYU Center for Data Science. 

Emad Mostaque is the Co-Founder and CEO @ StabilityAI, the parent company of Stable Diffusion. Stability are building the foundation to activate humanity’s potential.

Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC.

Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages.

Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses.

Cris Valenzuela is the CEO and co-founder of Runway, the company that trains and builds generative AI models for content creation. 

Richard Socher is the founder and CEO of Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016.

In Today's Episode We Discuss:

  1. Foundational Models: Analysis

  • Will foundational models become commoditized?
  • Who are the major players? What are their different strengths?
  • Who will win? Who will lose?
  • How important is the size of the model vs the quality of the data?

2. Open vs Closed:

  • What are the biggest pros and cons of an open ecosystem for LLMs?
  • Why is it naive to think that open-source LLMs will prevail?
  • What will determine which method wins?

3. An Analysis of the Incumbents:

  • Why is Google the most vulnerable? What can they do to regain ground?
  • Why is Apple the sleeping giant? How could they win the next wave of AI?
  • What should Amazon do today to compete with Microsoft?

4. The Future: Doom and Gloom?

  • Why is it ridiculous to assume AI systems want to dominate?
  • Why will AI create a renaissance of creativity and human freedom?
  • What role should regulation play in the advancement and progression of AI?

Nov 22, 2023

Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC. Jeff previously served as Twitter's Head of Consumer Product, a position he came to following the acquisition of his prior company, Crashlytics. Today, Crashlytics is the de-facto mobile crash reporting solution for iOS and Android and runs on over 6 Billion monthly active smartphones worldwide.

In Today's Episode with Jeff Seibert We Discuss:

1. The Art of the Pivot:

  • What are Jeff's biggest pieces of advice to founders pivoting?
  • How do you know when you have enough data to make the decision to pivot?
  • What are the single biggest mistakes founders make when pivoting?

2. AI: Who Wins and Who Loses:

  • Why does Jeff believe that OpenAI will transition into an infrastructure play?
  • What are the most significant challenges OpenAI will face moving forward?
  • Why does Jeff believe that Apple are best positioned to win in an AI world?
  • Why does Jeff believe that Google are the most vulnerable incumbent?
  • What would Jeff do if he was CEO of Google?

3. LLMs: What Happens Now:

  • Will we see the commoditization of LLMs?
  • What are the biggest misconceptions people have on training and fine-tuning LLMs?
  • Will we see LLMs increasingly specialise to vertical-specific models or will they remain horizontal?
  • What is the difference between a thick and a thin wrapper when building on top of LLMs?

4. Angel Portfolio in Review:

  • How many angel checks has Jeff written? How many failed? How many home runs?
  • Does Jeff believe that company valuations are being kept artificially high?
  • How did Jeff make 200x selling through the secondary market for a now failing company?
  • What are Jeff's three biggest pieces of advice for angels today?

Nov 20, 2023

Matteo Franceschetti is the Co-Founder and CEO @ Eight Sleep, a company dedicated to fueling human potential through optimal sleep. To date, Matteo has raised over $160M for the business from the likes of Founders Fund, Ryan Petersen, Naval Ravikant, Kevin Hart, AROD and many more.

In Todays Episode with Matteo Franceschetti We Discuss:

1. Why Did Sleep Need "Solving":

  • Why did Matteo decide he wanted to spend decades of his life-solving sleep?
  • If Matteo has known how hard it was going to be, would he do it again?
  • What does Matteo know now that he wishes he had known at the start of the journey?

2. Hiring the Best Team:

  • What is Matteo's playbook for hiring?
  • What are the five questions that Matteo asks in every interview?
  • What are big red flags? What are strong signals of great talent?
  • If people have been let go in a RIFF, is that a concern?
  • How does Matteo construct hiring panels? What vote count is enough for an approved hire?
  • What are Matteo's biggest lessons on title and pay a new hire receives?
  • What are some of Matteo's biggest lessons when it comes to firing people?

3. Funding the Business:

  • What was the hardest round to raise? Why?
  • Are investors justified in their skepticism of hardware?
  • What are the single biggest pieces of advice Matteo would give to founders on raising?
  • How impactful has it been having Keith Rabois and Founders Fund as an investor?
  • Do VCs really add value?

4. Mastering Health, Sleep and Nutrition:

  • How does your diet impact the quality of sleep you have?
  • How does exercise and the time of exercise impact your sleep?
  • What are some common rules on sleep that are BS and myths?
  • What are some of the most non-obvious truths about getting great sleep?

Nov 17, 2023

Rebecca Kaden is a Managing Partner @ Union Square Ventures, one of the leading early-stage firms of the last decade with investments in Twitter, Twilio, Coinbase and many more.

Nicole Quinn is a General Partner @ Lightspeed where she has led investments or sits on the board of Calm, Cameo and LunchClub to name a few.

Eurie Kim is a Managing Partner @ Forerunner Ventures, the leading early-stage consumer fund. Eurie has led investments and sits on the board of Oura, The Farmers Dog, Curology and more.

In Today's Roundtable We Discuss:

1. Seed Rounds:

  • Is it even possible for traditional seed funds to play in a world of multi-stage funds investing so aggressively at the seed stage?
  • Is seed immune to the macro environment? Will seed pricing remain as high as ever?
  • What advice does the team have for seed founders approaching a Series A? What do they need?

2. Series A:

  • How is the Series A market looking today? Is there a crunch at the Series A?
  • To what extent are valuations compressed at the Series A?
  • What 3 core elements do companies at the A stage, looking for a Series B next, need to focus on?

3. Series B and Beyond:

  • Is the real crunch at the Series B?
  • Why are down rounds so much better than structured rounds for companies raising?
  • Will we see a wave of M&A in the next 12 months?

4. Crypto, AI and Hot Takes:

  • Why is now the best time to be investing in crypto?
  • Why is investing in AI a lottery right now?
  • What is the most controversial thing that each believes today?

Nov 15, 2023

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support. Today Des leads all Intercom’s R&D efforts, and parts of Intercom’s marketing.

In Today's Episode with Des We Discuss:

1. From Consultancy to Founding a Unicorn:

  • What was the founding a-ha moment for Des and the team with Intercom?
  • Why does Des believe that most startup advice is BS and outdated in 5 years?
  • What does Des know now that he wishes he had known when he started?

2. LLMs: The World is Not Equal:

  • What does Des mean when he says the world of LLMs is not equal?
  • How do the different LLMs very in quality, price and speciality?
  • Does Des agree with Alex @ Nabla, "the best companies in the future will work with many LLMs at the same time and switch between them for different things"?
  • To what extent does Des believe LLMs will be commoditised and it will be a race to the bottom?
  • Would Des be a buyer of OpenAI at a $90BN price? Why not?

3. How to Survive in a World of OpenAI:

  • What two simple questions will determine if Open AI will kill your existing business?
  • What 3 criteria will determine if there is a new business to be built on top of OpenAI?
  • What is the different between a thin layer on top of an LLM and a thick wrapper with real value?
  • Which traditional incumbents are most vulnerable? What should they do in this new world?
  • How long does it take for incumbents to really be impacted?

4. The Titans of Tech: Who Wins:

  • Why does Des believe that Apple could be a massive winner in the next wave of AI?
  • Why does Des believe that Google have not been impressive and failed to keep pace?
  • Why does Des think OpenAI should be wary of Amazon? What could they do to threaten them?
  • What opportunity does Facebook have here? How could Instagram and Whatsapp win?

5. Startup and Investing 101:

  • Why does Des believe that every founder should write a blog post per week?
  • Why does Des believe that most B2B marketing sucks? What makes great B2B marketing?
  • What are Des' biggest lessons from the Hopin journey?
  • How has Des' angel investing changed in the last year with the rise of AI?

Nov 13, 2023

Ryan Petersen is Founder & CEO @ Flexport, a leader in global supply chain technology. In 2022, Flexport moved more than $26 billion of merchandise. Over the last 10 years, Ryan has raised close to $2.5BN for the business with the latest valuation pegging the business at $8BN. Prior to starting Flexport, Ryan was the founder and CEO of ImportGenius, a premier provider of transaction data for the global trade industry.

In Today's Episode with Ryan Petersen We Discuss:

1. The Origins of a Generational Defining Leader:

  • What did Ryan want to be when he was growing up?
  • How did scooters and motorbikes in China lead to the idea for Flexport?
  • What does Ryan know now that he wishes he had known when he started Flexport?

2. Speed and Money: The Secrets To Execution:

  • Does Ryan believe speed is key to execution? What is the difference between speed and velocity?
  • What advice does Ryan have to founders who raise a lot of money? How should it impact hiring?
  • What are the most common ways founders become inefficient post-fundraising?
  • Why does Ryan look to invest in founders with jaded pasts and a chip on their shoulder?

3. The Art of Resource Allocation:

  • Are the best CEOs the best resource allocators?
  • What is the single best resource allocation Ryan has made? What did he learn?
  • What is the worst? What did he learn?
  • What have been Ryan's biggest hiring mistakes? How did that change his approach?

4. The Wider World:

  • Is Ryan long or short on China? Why?
  • Will we see global trade become nationalized? Why?
  • Will we see interest rates raised further? What impact does that have on trade?
  • What has been the impact of war on trade and the shipping industry?

5. Ryan Petersen: The Father and Husband:

  • How has having kids changed how Ryan approaches leadership and management?
  • How does Ryan juggle 2 young kids and leading a 2,500 person company?
  • How does Ryan retain romance with his wife while also being a full-on CEO of a large co?
  • Does money make you happy? What does it help with? What does it not help with?

Nov 10, 2023

Chris Degnan serves as Snowflake’s Chief Revenue Officer and has been with the company since 2013. Starting as employee #13 and Sales employee #1, Chris built a go-to-market strategy from the ground up, driving sustained high growth and global reach. Under his sales leadership, Snowflake has grown its annual product revenue from $0 to over $1 billion. Prior to Snowflake, Chris served in Sales leadership roles at EMC and Aveksa, and worked in enterprise sales at Informatica and Covalent Technologies (acquired by VMware).

In Today's Episode with Chris Degnen We Discuss:

1. From SDR To World Leading CRO:

  • How did Chris first make his way into the world of sales?
  • What does he know now that he wishes he had known when he started in sales?
  • What are the single biggest mistakes young sales people make today scaling their careers?

2. The Secret to Hitting Quota in Sales:

  • Why does Chris believe all reps need to do 8 customer calls per week?
  • How do the best sales reps approach sales prospecting today?
  • Is cold outbound dead? How does Chris advise his teams on cold calls and emails?
  • What are the best reasons reps should say no to customers?
  • Should reps be discounting today? What is an acceptable level?

3. Sales and Product: The Most Important Relationship:

  • Why does Chris believe sales and product is the most important relationship?
  • What can leaders do to ensure sales and product communicate effectively?
  • How does Chris use sales calls today both with his sales team and with product?
  • What are the single biggest reasons comms between sales and product breaks?

4. Mastering Sales Leadership:

  • How does Chris approach sales forecasting? What works? What does not work?
  • Does Chris celebrate when quota is hit? How do you find the balance between pushing further and harder but also celebrating the wins?
  • How do the best sales leaders train and develop their talent? What do the worst do?

5. Customer Success is BS: Professional Services for the Win:

  • Why does Chris believe that customer succeed is BS and you should get rid of it?
  • Why are professional services so much better?
  • How should the org be structured then when removing CS and adding professional services?
  • Who is then responsible for upsell?

Nov 8, 2023

Danny Cohen is the President of Access Entertainment, a division of Len Blavatnik's Access Industries. Access Entertainment’s corporate investments include film and television studio A24; Europe’s fastest-growing company Tripledot Studios; creator economy leader Spotter; and a new immersive arts’ experience launched in collaboration with David Hockney and Lightroom. Before joining Access, Danny was the Director of BBC Television where he had responsibility for all of the BBC's network channels and the greenlighting and production of the BBC's drama, entertainment, comedy, arts, history, science, educational content and documentary. 

In Today's Episode with Danny Cohen We Discuss:

1. From Leading the BBC to Investing for Len Blavatnik:

  • How did Danny make his way from leading the BBC to investing for Len @ Access?
  • What was he most nervous about when making the transition to investing?
  • What has been the hardest investing skill to learn?

2. Great Founders are Like Great Actors:

  • What are the biggest similarities in what makes the best founders and the best actors?
  • How are the best founders different from the best actors?
  • Why does Danny believe the risk that an actor takes is so different to the risk founders take?
  • How does Danny feel both founders and actors can and should be managed?

3. The Future of Media:

  • What does Danny mean when he says he looks for "eyeballs and attention" when investing?
  • How does legacy media respond to the threat created by social media today?
  • How does AI change the future of content creation and distribution today?
  • How do the strikes in Hollywood impact the future of content supply?

4. Marriage, Children and Loneliness:

  • Why does Danny believe that loneliness will continue to be the biggest problem we face?
  • What are Danny's biggest pieces of advice from 17 years of happy marriage?
  • Why did Danny decide to not have children? What did that decision-making process look like?

Nov 6, 2023

Joey Zwillinger is the Co-Founder & CEO @ Allbirds, the company behind the world's most comfortable shoe. In Nov 2021, Joey took the company public and the stock soared to an all-time high of $4BN, today the company has a market cap of $137M. Prior to Allbirds, Joey spent six years at biotechnology firm, Terravia, leading its renewable chemical business, developing and selling high-performance algae-based chemicals into various industries such as CPG, personal care, and industrials.

In Today's Episode with Joey Zwillinger We Discuss:

  1. The Founding Moment:

  • How did Joey's wife's friendship lead to the co-founding of Allbirds?
  • What does Joey know now that he wishes he had known at the founding moment?
  • What does Joey believe he is running away from? What is he running towards?

2. Public Market Performance Review:

  • Why has Allbirds lost 97% of it's value since going public? What mistakes were made?
  • Why has revenue declined for the first time this year?
  • What strategic investments have Allbirds pulled back on or paused entirely?
  • When will Allbirds be profitable?

3. The Competition:

  • How do Allbirds compete and catch up with On and Hoka?
  • What strategic mistakes did Allbirds make in COVID that allowed others to take the crown?
  • Was the movement into running and athletics a mistake for Allbirds?

4. Joey Zwillinger: The Leader and Person:

  • Did Joey take secondaries out during the Allbirds journey?
  • How does Joey reflect on his own relationship to money?
  • How has Joey dealt with the last 12 months personally? How does he manage the stress effectively?

Nov 3, 2023

Jack Altman is the Founder and CEO @ Lattice, the #1 people management platform, last valued at $3BN. Jack is an investor through his founding of Jack Altman Capital where he has invested in WorkOS, NexHealth,, Mercury and more.

Auren Hoffman is the Founder and CEO @ Safegraph, the most accurate database of global points of interest, last valued at $550M. Auren is an investor through his founding of Flex Capital where he has invested in Chime, Checkr, Coinbase, Flexport, Vercel and more.

Jason Lemkin is the Founder and CEO @ SaaStr, the world's largest SaaS community. Jason is an investor through his founding of The SaaStr Fund. In the past, Jason has invested in Pipedrive, Algolia, Salesloft, Front, GreenHouse,, Gorgias and more.

In Today's Episode on Founder-Led Funds We Discuss:

  1. Why have we seen the rise of "Founder-led Funds"?
  2. Are founder-led funds more empathetic to the founders they invest in?
  3. How do founder-led funds source and pick investments in a way that traditional VC does not?
  4. Will we see founder-led Funds truly compete against the Sequoias of the world?
  5. How does being an operator make you a better investor?
  6. How does investing help you be a better founder and operator?
  7. How do you communicate your investing practice and firm to your company and team?
  8. What are the biggest excitements and concerns LPs have for Founder-led Funds?
  9. Will we see the face of venture changing much more broadly and structurally?
  10. How do founder-led funds manage both time and company conflicts?

Nov 1, 2023

David Meyer is the SVP Products at Databricks where he drives product strategy and execution. He previously ran Engineering and Product Management at OneLogin, where he grew the company to thousands of customers and market leadership. Before OneLogin, he cofounded UniversityNow, an accredited open university system, running Product and Engineering. Prior to that, David managed a $1 billion portfolio of business intelligence products at SAP and co-led cloud strategy. His first software journey was at Plumtree which went public before being acquired by BEA in 2005.

In Today's Episode with David Meyer We Discuss:

  1. Entry into Product:

  • How did David make his way into the world of product? Why did he not want to go into it?
  • Why does David advise everyone "do not go into product management"?
  • What does David know now that he wishes he had known when he entered product?

2. How to be a Great Product Leader:

  • Why does David think most leaders suck at leading?
  • Why is the most important thing to make your team feel seen? What can leaders do to ensure this?
  • Why does David help his team members to find other roles outside of the company?

3. Building the Best Product Team:

  • How does David hire for product today? What questions does he ask? What signals does he look for?
  • What are David's biggest hiring mistakes? How did they change his approach?
  • What are the biggest mistakes founders make when hiring for product?
  • Why should you hire people who are not in product today?

4. David Meyer: The Art or Science of Product:

  • Is product more art or science? If David were to put a number on it, what would it be?
  • Is simple always better when it comes to product?
  • Will AI remove the importance and focus on UI?
  • Why are the most impressive companies business model innovations not product innovations?

Oct 30, 2023

Nick Tomaino is the Founder and General Partner @ 1confirmation, one of the leading seed firms fueling the decentralization of the web and society. The fund started with $26M in backing from individuals including Peter Thiel and Mark Cuban and it has been reported that the firm now has over $1B in assets under management. Nick has led seed investments in OpenSea, dYdX, SuperRare, Polkadot and Cosmos among others. Prior to 1confirmation, Nick was a Principal @ Runa Capital and before that led business development and marketing at Coinbase in the early days of the company.

In Today's Episode with Nick Tomaino We Discuss:

  1. From Cryptokitties to founding the Leading Seed Crypto Firm:

  • How did Nick first come into contact with crypto and bitcoin specifically?
  • How did getting fired from Coinbase catalyse his move into venture?
  • What does Nick know today that he wishes he had known when he started investing?

2. The Landscape Today: Funds and SBF

  • Are the current generation of crypto funds too large? Should they give money back to their LPs?
  • Will the next generation of crypto funds be smaller? Are any crypto funds able to raise right now?
  • Why does crypto Twitter hate crypto VCs? Who are the worst VCs for pump and dump?

3. SBF & FTX: What Actually Happened, Who is to Blame, What Happens from here?

  • What is the biggest misconception on SBF and FTX today?
  • Who should be held accountable? What else would Nick like to see?
  • How should FTX change the way that LPs invest into venture managers?

4. How to Build the Best Crypto Portfolio in Venture:

  • How large are the funds? How does Nick determine the right size for a fund?
  • How many investments does Nick make per fund? How do loss rates look in crypto?
  • What have been Nick's biggest investment hits and losses? How did that impact his mindset?

5. The Future for NFTs and Opensea:

  • Why does Nick remain bullish on the future of NFTs?
  • How is Nick able to remain optimistic about the future of Opensea given their volumes?
  • Where does Nick believe the fair price for Opensea should be today?
  • Did Nick sell their Opensea at the $13Bn round?

Oct 27, 2023

Ed Sim is one of the best seed round investors in venture as the Founder and Managing Partner @ Boldstart, Ed focuses specifically on developer, infra and SaaS at pre-seed and seed round. Over the last decade, Ed has backed some of the best including Snyk, BigID, Kustomer, Front and Superhuman.

In Today's Episode on Seed Rounds We Discuss:

  1. The Three Types of Seed Round:

  • What are the three different types of seed round today?
  • Has seed ever been this competitive?
  • Will seed be unimpacted by the macro decline we are seeing?
  • Why are growth and multi-stage funds being more active than ever in seed?

2. Too Much Cash Will Kill You!

  • Why does Ed believe that too much capital can kill companies at the seed round?
  • Why does Ed believe that the best founders are not always optimising for the highest price?
  • What are the single biggest negatives of taking a high price at the seed round?
  • What advice does Ed have for founders who have large offers from multi-stage funds at seed?

3. Is Growth Dead?

  • Why does Ed disagree and suggest that growth is not dead?
  • What do multi-stage and growth funds now what to see that they did not before?
  • How will the growth market evolve over the next 12-18 months?

4. IPOs, AI and M&A:

  • What will cause the IPO windows to crack open again?
  • Why does Ed believe that many investing in AI are simply giving money to Nvidia?
  • Does Ed agree that 95% of the cash going into AI from venture today will go to zero?
  • Will we see more or less M&A in the next 12 months?
  • How did Ed evaluate the Loom acquisition by Atlassian?

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