1,146 episodes

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.

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

    • Business
    • 4.4 • 429 Ratings

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.

    20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

    20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

    Sam Blond is the former CRO at Brex, where he led the company from near $0-$400M in ARR and a $12.5B valuation. Before Brex, Sam was VP of Sales at Zenefits, where he led the company from $0-$70M ARR in 2 years and a $4.5B valuation. Sam joined Founders Fund as a Partner in 2022 and recently left to focus more on operating.

    In Today's Episode with Sam Blond We Discuss:
    1. Lessons From Scaling Brex to $400M ARR & Zenefits to $70M ARR:

    What are the secrets that very few people know, that led to the success of Brex and Zenefits? What was the single worst sales investment Brex made? What was the best? What are Sam's biggest tips to people picking the rocketship they will join?
    2. Who, What and When to Hire:

    When is the right time to hire your first sales rep? Should the founder be the one to create the sales playbook? What is the right profile for the first sales hire? Does it matter if the new hire has domain experience? Why does Sam always advocate to hire through network and not recruiters?
    3. How to Hire the Best Sales Reps:

    What are the questions Sam always asks in interviews with sales hires? Does Sam do case studies with candidates? What is he looking for? What are the biggest green and red flags a candidate can show in an interview process? What are the biggest mistakes founders make when hiring sales teams?
    4. How to Have the Best Performing Sales Team:

    What are the three ways to measure the success of a rep in the first 30-60 days? Why does Sam believe most startups are doing outbound wrong? What should they change? Why does Sam believe demand gen is the bottleneck for all companies? What can be done to solve the demand gen challenge? How does outbound change in a world of AI?

    • 1 hr 14 min
    20VC: Are the Best CEOs the Best Fundraisers, Are the Best Founders Insiders or Outsiders to a Problem, Why Ownership Should Not Be a Focus in VC & The Biggest Lessons Scaling MongoDB to $26BN Market Cap with Kevin Ryan, Founder @ AlleyCorp

    20VC: Are the Best CEOs the Best Fundraisers, Are the Best Founders Insiders or Outsiders to a Problem, Why Ownership Should Not Be a Focus in VC & The Biggest Lessons Scaling MongoDB to $26BN Market Cap with Kevin Ryan, Founder @ AlleyCorp

    Kevin Ryan is one of the leading serial entrepreneurs and investors in New York. Previously he co-founded MongoDB, Business Insider, Gilt Groupe, Zola, Nomad Health, Pearl Health, and was the CEO of DoubleClick (Acquired by Google for $3.1B). Today, Kevin is the founder and CEO of AlleyCorp, a venture capital firm that incubates and invests in transformative companies in healthcare, diversified tech, robotics, and impact. Just yesterday, Alleycorp announced their $250M fund, their first ever external capital. 
    In Today’s Episode with Kevin Ryan We Discuss:
    Early Signs of Entrepreneurship
    How did Kevin’s early life shape his career? How would his parents and teachers describe him?
    Does Kevin agree that successful entrepreneurs always show signs early?
    What does Kevin think about luck vs. skill? Why does Kevin think that most things are out of your control as an entrepreneur?
    Lessons from Founding 10+ Companies Worth $27BN
    Does Kevin agree the best CEOs are also the best fundraisers?
    What were Kevin’s biggest lessons from scaling DoubleClick from 20 to 2000 employees?
    What was Kevin’s a-ha moment behind Business Insider? What was the reason behind its success?
    Why does Kevin believe the best founders are always in unfamiliar fields?
    Incubating World’s Best Companies
    How does Kevin allocate resources between incubations vs. investments?
    What are the biggest commonalities between successful companies at AlleyCorp?
    Is Kevin a market-led or people-led investor?
    What does Kevin think is the most important element in achieving product-market fit?
    What was Kevin’s biggest miss on selecting founders? What were his takeaways?
    Current State of Venture
    Why does Kevin believe venture is more competitive now than ever before?
    What does Kevin know now that wish he’d known when he started investing?
    Does Kevin agree rich investors make better investors?
    Why does Kevin not care about ownership?
    Does Kevin agree with Doug Leone that venture has transitioned from a high boutique margin industry to a low margin commoditised industry?
    Does Kevin agree with Peter Fenton that price is a mental trap?
     

    • 1 hr 3 min
    20VC: Postmates Founder Basti Lehmann on How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN, Why Great VCs Add No Value and VC Value Add is BS Marketing & Why The Biggest Companies in History Will be Born Today and Replace Incumbents

    20VC: Postmates Founder Basti Lehmann on How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN, Why Great VCs Add No Value and VC Value Add is BS Marketing & Why The Biggest Companies in History Will be Born Today and Replace Incumbents

    Basti Lehmann is the co-founder and former CEO of Postmates, the on-demand delivery service that raised over $900M from the likes of Tiger Global, Founders Fund, Spark Capital and Andreesen Horowitz. Following Uber’s $2.65BN acquisition in 2020, Basti founded TipTop, a platform for fast tech sales which Marc Andreesen led the $20M seed round for.

    In Today’s Episode with Basti Lehmann We Discuss:
    From US Immigrant to Billion Dollar Founder
    How did Basti start his career hacking AT&T?
    How did early hardships shape Basti’s work ethic?
    What were Basti’s biggest challenges building Postmates?
    Lessons from Raising $900M
    How did Basti raise $20M from Marc Andreesen?
    How does Basti select which VCs to work with?
    Why does Basti think 99% of VCs are sheep?
    Why does Basti think great VCs add no value?
    Why does Basti think having to educate investors is a massive red flag?
    Selling Postmates for $2.65BN
    Why did Basti sell Postmates to Uber? How did the acquisition happen?
    Was there anything Basti would have done differently?
    What does Basti think makes Dara Khosrowshahi a great CEO?
    What is Basti’s biggest advice to founders on acquisitions?
    Future of AI: Startups or Incumbents?
    What does Basti think is the biggest challenge of LLMs today?
    Why does Basti think inference computing will be the future of AI?
    Why does Basti think incumbents can be replaced?
    Why does Basti think the biggest companies are being born today?
     

    • 59 min
    20VC: Oscar Health: How to Deal with a 94% Decline in Market Cap, "Why I Stood Aside as CEO" and The Rebound Journey to $5.8BN in Revenue with Mario Schlosser, Co-Founder @ Oscar Health

    20VC: Oscar Health: How to Deal with a 94% Decline in Market Cap, "Why I Stood Aside as CEO" and The Rebound Journey to $5.8BN in Revenue with Mario Schlosser, Co-Founder @ Oscar Health

    Mario Schlosser is the Co-Founder and Chief Technology Officer at Oscar Health. The public company that went public with a market cap of $7.1BN. Following a tumultuous time in the markets, their stock price dropped 94%. Today, the company has rebounded and has a market cap of $3.2BN with an astonishing $5.8BN of revenues. Before co-founding Oscar, Mario also co-founded the largest social gaming company in Latin America.

    In Today's Episode with Mario Schlosser We Discuss:
    1. From German Middle-Class to Public Company Founder:

    How did Mario make his way into the world of tech and come to co-found Oscar with Josh Kushner? Does Mario agree with Jensen Huang that "we should all have lower expectations"? What does Mario know now that he wishes he had known when he started Oscar?
    2. Why Did Oscar Tank 94% in the Public Markets:

    What was the core reason why Oscar tanked 94% in the markets? What would Mario have done differently knowing all he knows now about public markets? Does Mario regret going public? What are the biggest pros and cons?
    3. The Mental Challenge of a 94% Market Cap Decline:

    How did Mario mentally deal with the company being down 94%? What does he say to himself in the truly hard times? How did Mario use his co-founder, a coach and his family, to get through the really bad times? What are Mario's experiences like with anti-depressants? What worked? What did not?
    4. Firing Yourself as CEO:

    Why did Mario decide to step aside as CEO? What was the decision-making process? On reflection, does Mario think he was a good CEO? Where was he good? Where was he bad? What are the biggest management pieces of advice that Mario thinks are BS?

    • 1 hr 9 min
    20VC: Founders Fund's Trae Stephens on Why The Most Competitive Deals are the Worst, Why No Company is Successful Because of their VC, Why We are Making ZIRP Mistakes Again Today, Why Loss Ratio is BS and Upside Maximisation is Everything

    20VC: Founders Fund's Trae Stephens on Why The Most Competitive Deals are the Worst, Why No Company is Successful Because of their VC, Why We are Making ZIRP Mistakes Again Today, Why Loss Ratio is BS and Upside Maximisation is Everything

    Trae Stephens is a Partner at Founders Fund, one of the world's leading funds where he has worked with some of the best and backed the likes of Palmer Luckey with Oculus and Ryan Peterson @ Flexport since the very early days. Trae is also Co-founder and Executive Chairman of Anduril Industries, a defense technology company focused on autonomous systems, and Co-founder of Sol, a next-generation wearable e-reader. Previously, Trae was an early employee at Palantir Technologies, where he was also an integral part of the product team, leading the design and strategy for new product offerings.

    In Today's Episode with Trae Stephens We Discuss:
    1. From Hustling into Georgetown to Peter Thiel Ushering You into VC:

    What is Trae's story of how he got into Georgetown University, despite being rejected the first time? How did Trae make his way into the world of VC? How did Peter Thiel recruit him to Founders Fund? What advice did Brian Singerman give Trae in his first week in VC? Why is it so important?
    2. How the Best Venture Firm in the World Invests:

    Decision-Making Process: Why do Founders Fund not have partner meetings? What is the investment decision-making process? Why does more process lead to mediocre outcomes? Competitive Deals: Why does Trae believe the most competitive deals are always the worst? What do Founders Fund do to specifically avoid the "herd mentality"? Upside Maximisation: Why does no one at Founders Fund care about "downside protection"? How do the team approach scenario planning and upside maximisation?
    3. Do VCs Really Add Value:

    Why does Trae think putting VCs on a board for "value add" is total BS? Are there any cases in which Trae believes the VC can really move the needle for a company? Why does Trae believe venture would be better if it were just operator investors? Why does Trae believe platform approaches to VC value add is BS?
    4. The Future of VC: Who and How to Win:

    How did being an operator at the same time as investing, make Trae a better investor? Why does Trae believe that vertical investing is BS and generalised is better? How does Trae favour; market, product and people? Will Trae back a founder when he hates the idea? What have been Trae's biggest lessons from his biggest hits and biggest misses in 10 years?

    • 1 hr 12 min
    20VC: The Memo: The $23BN Company You Might Not Have Heard Of: Tradeweb, The Story of 27 Years of Compounding Growth Leading to the Market Leader with $1.4BN in Revenue and 50% EBITDA Margins

    20VC: The Memo: The $23BN Company You Might Not Have Heard Of: Tradeweb, The Story of 27 Years of Compounding Growth Leading to the Market Leader with $1.4BN in Revenue and 50% EBITDA Margins

    Billy Hult is Chief Executive Officer of Tradeweb Markets (Nasdaq: TW), as Billy puts it, they are the "electronic interface that connects Citadel and Goldman". They are also one of the most under the radar but incredible businesses of the last 20 years. Through no glitz acquisitions or specific moments, TradeWeb has compounded organic growth for the last 27 years to today, with a market cap of $22BN.

    In Today's Episode with Billy Hult:
    1. From Betting Shop Worker to Public Company CEO:

    How would Billy's teachers and parents have described the young Billy? Why does Billy think it is so important to have a hard first job when growing up? What does Billy know now that he wishes he had known when he started?
    2. What it Takes to be a World-Leading CEO:

    How does Billy define the role of the CEO? What are the core tenets? What has been the single hardest element of CEOship to learn? Does Billy care about being liked? How does that impact his management style? Why does Billy think it is so important for CEOs to make "big bets"? What have been his biggest?
    3. Hiring World-Class Teams in 2024:

    What have been some of Billy's biggest hiring mistakes? What did he learn from them? How does Billy weigh IQ vs EQ and hustle? Which wins? Why? Does Billy think this generation of millennials is too soft? What are the single biggest lessons Billy has on when to delegate vs when to retain control?
    4. Money, Power and Family:

    How does Billy approach his relationship to money today? How has it changed over time? Fame, power or money, rank them from 1-3. How does Billy rank them? How does Billy describe his own style of parenting? How has it changed over time?

    • 51 min

Customer Reviews

4.4 out of 5
429 Ratings

429 Ratings

AH_12 ,

Asparagus from Veggie Tales

I’m almost certain the host is the voice actor for the asparagus from veggie tales

Arj-Un ,

Must listen for any founders.

Harry is simply brilliant at this. I’ve learnt more as a founder listening to this podcast than reading a plethora of books. His curation of questions, guest list, and applicability of content to real world problems that founders face on their journey is unmatched. It is timeless in that it keeps with the latest trends in the industry. When you’re on a walk, a drive, or simply with a few minutes on hand, this podcast will help you realize new pathways applicable to your journey. Whether you’re a first time founder or a serial entrepreneur, add this to your collection of knowledge bases. You will be thankful!

Adi rates ,

Too good to miss!

Just heard my first show, the Ultimate Hiring Playbook with Matteo Franceschetti and I was glued to both the content and the delivery. Harry Stebbings packed dozens of high value questions and Matteo delivered as much good insights as he possibly could.

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