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: January, 2024
Jan 31, 2024

Dave Kellogg is one of the OGs of Saas. Among his many accomplishments, Dave was the CMO of Business Objects where he helped scale the business from $30M to $1BN in revenue. Dave has also been a CEO twice, once scaling the business from $0 to $80M and the other business from $8M to $50M before selling it. Dave is also an advisor to some of the best including GainSight, Logickull, MongoDB, Pigment, Recorded Future, and Tableau.

In Today's Episode with Dave Kellogg We Discuss:

1. What are the Metrics That Matter:

  • Why is CAC payback period such a flawed metric?
  • What is CAC ratio? Why is it more effective than understanding payback?
  • Why is gross revenue retention more important than net revenue retention?
  • What are the single biggest mistakes that founders make when using metrics today?

2. How to Build and Scale the Best Sales Teams:

  • Why should founders hire three sales reps at one time? What is the benefit?
  • What are the three different types of sales calls all teams must have?
  • What should all CEOs and Heads of Sales ask of their sales team in forecasting?
  • What is the single biggest mistake most companies make in forecasting?
  • How should a CEO/board member respond to a sales team that lets a deal slip to next quarter?

3. Are CFOs Buying New Tech and How to Win Renewals:

  • Are CFOs open for business? How has the top down sales process changed in the last year?
  • Why is the way that startups think about renewals completely broken?
  • What are the three different types of customer success teams we have today?
  • What is the core role of customer success? How can we incentivise them to sell more?

4. Mastering Product Marketing, Customer Profiles and Crossing the Chasm:

  • How can we use product marketing to increase sales velocity?
  • What is the single biggest risk in product marketing today?
  • What does Dave mean when he says "an ICP starts as an aspiration and becomes a regression?"

Jan 29, 2024

Ryan Akkina is a member of the Global Investment Team at the MIT Investment Management Company (MITIMCo), which is responsible for managing MIT's endowment and pension plans. Ryan has invested in the likes of Sequoia, Kleiner Perkins, a16z, Greenoaks and Initialized to name a few. Ryan also leads many of MITIMCo's direct co-investments including most notably into Coupang and Rippling. Prior to joining MITIMCo, Ryan was a consultant at McKinsey & Company.

In Today's Episode with Ryan Akkina We Discuss:

1. From Engineer to LP with MIT:

  • How did Ryan make his way into the world of fund investing as an LP with MIT?
  • Why did he turn down the chance to be a VC early in his career?
  • What does Ryan know now that he wishes he had known when he started at MIT?

2. The Manager Evaluation Process for MIT:

  • What does Ryan look for most when investing in new managers?
  • How important is track record when evaluating a new manager?
  • What is the biggest mistake Ryan has made in picking a manager? What did he not see that he wish he had seen? How did that change his process?

3. How MIT Builds Their Portfolio:

  • How does MIT construct their portfolio from private to public to everything in between?
  • What are the three different types of check sizes that MIT writes when investing in new managers?
  • What are the most common reasons why MIT will not re-up with a manager?
  • What are the single biggest reasons why great managers turn bad?

4. MIT: The Direct Investor:

  • Why does MIT see so much opportunity in direct investing?
  • How does MIT approach the direct investing process? How do they approach underwriting themselves vs working with their managers in the process?
  • How do MIT think about the right number of direct deals to make up their portfolio?
  • How do they approach check sizing on a per-company direct investment?
  • What has been Ryan's biggest direct investing mistake? How did that change his approach and mindset?

5. LP Markets Today and Where We Go From Here:

  • Are LPs open for business today? What type of firms will not struggle? Which will?
  • How does Ryan view liquidity windows today? When will M&A and IPO markets open?
  • What would Ryan most like to change about the world of LPs?
  • Why does Ryan believe the LP incentive structure in terms of compensation is broken?

Jan 26, 2024

Dave Ripley is the CEO @ Kraken, one of the world's largest cryptocurrency exchanges, valued in 2022 at a whopping $10.8BN. Prior to Kraken, Dave was the Co-Founder of Glidera, a market-leading Blockchain technology company that Kraken acquired in 2016.

In Today's Episode with Dave Ripley:

1. From Boston Consulting Group to CEO of Kraken:

  • How did Dave first make his way into the world of crypto?
  • What are the single hardest elements of a CEO transition?
  • What does Dave know now that he wishes he had known about CEOship?

2. What is the Usage for Crypto:

  • Other than as a store of value, what application usage does crypto serve?
  • Global payments are fine as is and are improving, why do they need crypto?
  • Global remittance is served by Remote and Deel, why do they need crypto?
  • No applications have been provided well, what really is the use case that makes sense?

3. Should Gensler Be Let Go and The SEC is Wrong:

  • Why is the approach of the SEC completely flawed?
  • Should Gensler be fired for his ineffectiveness?
  • What is the right policy stance and approach to take from here?

Jan 24, 2024

Sean Murray is the CRO @ Greenhouse which is the fourth company Sean has scaled successfully into the enterprise. Sean's prior roles include revenue leadership positions at Saleloft (CRO), Xactly (VP Sales), and CEB, now Gartner (Head of MID Global Sales).

In Today's Episode with Sean Murray

1. The Origin Story: Is a Love of Sales Born:

  • How did Sean first fall in love with Sales?
  • What does Sean know now that he wishes he had known when he started his career in sales?
  • What is Sean's biggest advice to a young person entering the sales world today?

2. Sales has Changed; You Need to Change with It:

  • Why do CMOs need to be good sellers and CROs need to be good marketers today?
  • Have we seen the total blending of sales and marketing today?
  • Should we get rid of all sales teams and just have content marketing teams?

3. How to Move into the Enterprise Successfully:

  • What are the three biggest mistakes startups make when scaling into the enterprise?
  • What easy wins can they do early in the sales process to enterprises to get a good start?
  • How important are logos? Does social validity really work in enterprise?
  • How should sales teams use discounting in enterprise sales most effectively?
  • What is the right way for sales leaders and CROs to budget for enterprise?
  • Is there a way to test enterprise without committing the company and a lot of resources?

4. How to Build the Best Sales Team Today:

  • What is the right hiring process for all new sales hires?
  • What are the questions you have to ask in the interviews?
  • What do the case studies entail? What are signals of the best reps?
  • What are the biggest mistakes teams make when hiring new sales reps?
  • What have been Sean's biggest lessons on comp and negotiation with new reps?

Jan 22, 2024

Adam Fisher is a Partner @ Bessemer Venture Partners and one of the most successful investors in Israel over the last two decades with seed investments in Fiverr, Wix, Melio, HiBob and more. Adam has now made over 60 investments and has had an incredible 23 successful exits. Adam has now been in venture for over 27 years having started his career at Jerusalem Venture Partners in 1996.

In Today's Episode with Adam Fisher We Discuss:

1. Lessons from 27 Years in Venture Capital:

  • How did Adam first make his way into the world of venture straight out of college?
  • Does Adam agree with Doug Leone that VC has changed from a "boutique, high margin business to a commoditized, low margin industry"?
  • What does Adam know now that he wishes he had known when he started in venture?

2. How to Pick Winners: 23 Exits in 60 Investments:

  • To what extent does Adam think pattern recognition is a good thing? When is it bad?
  • Does Adam prefer to invest in outsider founders approaching a problem with fresh eyes or insider founders who know the problem back to front?
  • Why does Adam believe that "category creation is BS"?
  • Why does Adam not like to invest in big, hugely ambitious markets? Why are smaller markets best?

3. The Deal: Mastering the Art of Negotiation and the Deal:

  • How does Adam reflect on his own relationship to price?
  • When doing an investment, does Adam think about who would do the next round?
  • How important is ownership to Adam? Does he want it all on first check?
  • Why does Adam not like to invest in hot AI rounds?
  • What have been Adam's single biggest investing mistakes? How did it change his approach?

4. Mastering the Art of Portfolio Management:

  • Why does Adam believe that it is impossible to know which of your portfolio will be the breakout winners early on?
  • How does Adam approach reserve allocations with this in mind?
  • How does Adam know when is the right time to sell a position?
  • What does Adam believe was the biggest sin of the zero interest rate environment period?

Jan 19, 2024

Zaria Parvez is Duolingo’s Senior Global Social Media Manager where she is famed for scaling Duolingo's TikTok from 50K followers in September 2021 to 8M followers today. The Duolingo TikTok has 143 viral videos (view counts of 1M or higher) due to Zaria’s creativity. What started as a test-and-learn initiative has become Duolingo's most successful social buzz and word-of-mouth initiative to date – all because of Zaria's insights, instincts, and expertise.

In Today's Episode with Zaria Parvez:

1. From College Student to TikTok Star:

  • How did Zaria make her way into the world of social media and Duolingo?
  • When did Zaria realize the power of TikTok? What did she do as a first step?
  • What does Zaria know now about growing on TikTok that she wishes she'd known when she started?

2. How to Create a Viral Video:

  • What have been Zaria's biggest lessons in what it takes to create a viral video?
  • What does Zaria mean when she says the best content is "medicine to candy"?
  • What does the ideation process look like for new content ideas?
  • How much budget should be set aside for new content?
  • What does Zaria mean when she says Duolingo's TikTok needs to view like a "sitcom"?

3. How to Tie Success in Content Back to Hard Dollars:

  • How is "success" in content measured at Duolingo?
  • How fast does Zaria know if a video is a hit or not? What is the right cadence to post?
  • How should companies determine whether content is ultimately successful or not?
  • What is the single metric that Zaria is focused on today?

4. How to Build the Best Content Team:

  • Why should companies not work with content agencies if they want the best results?
  • Why does Zaria believe you have to hire troublemakers if you want success in content?
  • What are the single biggest mistakes companies make w

Jan 17, 2024

Shyam Sankar is Chief Technology Officer and Executive Vice President of Palantir Technologies in addition to the Chairman of Ginkgo Bioworks. Shyam holds a B.S. in Electrical and Computer Engineering from Cornell University and a M.S. in Management Science and Engineering from Stanford University.

In Today's Episode with Shyam Sankar:

1. Journey to the Top of Defence:

  • How did Shyam make his way into the world of startups and get a role with Kevin Hartz at Xoom?
  • How did seeing Shyam's parents lose everything impact his mindset and drive?
  • What does Shyam know now that he wishes he had known when he started his career?

2. How the World's Governments Buy Defence:

  • What is the playbook for selling defence to different governments?
  • Why is the way that governments purchase and procure so broken?
  • If Shyam were head of the DOD, what would he change?
  • Why does the DOD "need to pick winners"?
  • Which governments are the best to work with? Which are the worst?

3. A World In Conflict: What Changes:

  • How does conflict change the buying process and urgency for governments?
  • How do elections change the buying cadence and process for different governments?
  • Looking forward to 2024, how does Shyam predict the state of different global conflicts?

4. Hiring 101: You Have To Hire Artists:

  • What have been Shyam's single biggest lessons on what it takes to hire the best of the best?
  • Why does Shyam believe that hiring great people is like talent management in Hollywood?
  • Why does Shyam believe talent should be "shielded from budgets"?
  • What have been some of Shyam's biggest hiring mistakes? How did he learn from them?

Jan 15, 2024

Brian Halligan is the Co-Founder and Executive Chairperson of HubSpot. Brian led the business as CEO for 15 years from Day 1 to a $30BN public company with 7,000 employees. Among Brian numerous achievements, Brian is famed for coining the term "inbound marketing", he is a globally recognised author, he is also an incredible teacher having developed MIT’s popular Scaling Entrepreneurial Ventures class. In addition to all of this, he is also the Co-Founder of Propeller Ventures, a $100 million climate tech venture fund, specializing in ocean innovation investments.

In Today's Episode with Brian Halligan We Discuss:

1. The Makings of a Generational Defining Entrepreneur:

  • How did the first job as a paperboy lead to the founding of a $30BN company?
  • How does Brian analyse the importance of luck vs skill in success?
  • What is Brian running from? What is he running towards?

2. How to Be the Best Leader from 15 Years as CEO:

  • What are Brian's biggest lessons in leadership from Elon Musk and Jensen Huang?
  • How has Brian's leadership style changed over time?
  • Why is the way leaders prioritise what they do today completely broken?
  • How can leaders use quarterly goals to prioritise most effectively?
  • Does Brian believe people are born CEOs? Are MBAs worth it for CEOs?

3. How to Build the Best Team:

  • What is the #1 failure condition of teams today?
  • Why does Brian believe most of your employees are mercenaries and not missionaries? Is that ok?
  • Why do recovery plans never work? Once lost, can trust in teams be regained?
  • Are people destined for certain stages of company growth?
  • Why does culture always break when teams hit 100 people?

4. The Best Deal in VC History:

  • Why did Hubspot sell 47% of the company to General Catalyst in their Series A?
  • How did Sequoia come to lead their Series D?
  • How much of a needle mover is it for companies and founders to have Sequoia invest?
  • Why did Brian sell secondary to Sequoia in the Series D? Is it the most costly mistake he has made?

Jan 12, 2024

Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Just last week, Keith announced he would be rejoining Khosla from Founders Fund, where he spent an immensely successful 5 years as a General Partner. Prior to Founders Fund, Keith started his career at Khosla where he spent 6 years and led investments in DoorDash, Opendoor, Webflow and more.

In Today's Episode with Keith Rabois We Discuss:

1. The Decision to Rejoin Khosla Ventures:

  • Why did Keith decide to rejoin Khosla Ventures from Founders Fund?
  • What did Keith miss most that Khosla did, that Founders Fund did not?
  • How did Delian take the news?

2. Comparing Two Great Firms: Founders Fund vs Khosla Ventures:

  • Investing Style: How does Keith compare the investing styles when analyzing FF and KV?
  • Price Discipline: Which firm is more price-disciplined? Does price discipline even matter?
  • What are the single biggest mistakes Keith has made on price? How did it change how he invests?
  • Founder Type: What sort of founder would choose KV? What founder would choose FF?
  • How did the depth & quality of investment decision-making compare between KV and FF?

3. What It Takes To Win in Venture in 2024:

  • Liquidity: What have been Keith's biggest lessons on when is the right time to sell positions?
  • Capital Planning: What have been Keith's biggest lessons on the most effective use of reserves?
  • Why does Keith believe if you do not lose some deals as an investor, you are not competing for the right companies?
  • Khosla Ventures recently raised $3BN. How important is the ability to support companies across their lifetime in 2024 vs stage specific?

4. Where is The Best Place to Invest:

  • Why does Keith think seed is the best place to be investing today?
  • Why despite the better risk/reward profile, does Keith think Series A is not the best place to invest?
  • Does Keith believe we will see the return of growth investing in 2024?
  • What does Keith predict for the M&A market in 2024? Did Figma kill all activity?
  • When will the IPO windows open again? Why would Stripe go out this year?

5. Keith Rabois: AMA:

  • Why did Keith not want to start his own fund? Will he ever?
  • What have been Keith's biggest lessons from working with Vinod Khosla and Peter Thiel?
  • What were Keith's biggest lessons from Roelof Botha on what it takes to be an effective board member?
  • How does Keith think about bitcoin in 2024?

Jan 10, 2024

Jamin Ball is a Partner @ Altimeter Capital where he sits on the board of Airbyte, Clickhouse, dbt Labs, Prisma, Tabular. Jamin has also led investments in Deel, MotherDuck, Personio and Starburst. Prior to Altimeter, Jamin spent 5 years at Redpoint where he led investments in Workato, Monte Carlo, Cityblock Health, Root Insurance.

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 We Discuss:

1. How to Invest Successfully in 2024:

  • What are the three biggest mistakes growth investors can make in 2024?
  • Why should founders not start a platform company?
  • What were Jamin and Ed's biggest mistakes from the ZIRP era?
  • How does Jamin justify paying an $8BN price for Hopin? What were his lessons?

2. The M&A Markets in 2024:

  • Did Figma kill the M&A markets for 2024? What should we expect in M&A?
  • Why will private companies buying private companies be a massive segment in 2024?
  • What are Ed and Jamin's biggest tips to founders considering selling their company in 2024?

3. When Will IPOs Come Back:

  • What will be the catalyst to the opening of the IPO markets?
  • Will Stripe and Databricks go public in 2024? What others should we expect?
  • What are the three requirements for a company to go public in 2024?

4. Firesales: Investors Need Cashback:

  • Why does Ed believe now is the time in the cycle where late-stage investors want cash back to distribute back to their LPs or to recycle?
  • What should we expect to see in terms of acqui-hires and firesales?
  • What are the different incentives when comparing founders vs early stage VCs vs late stage VCs when it comes to acquisitions?

Jan 8, 2024

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 and the firm now has over $1B in assets under management. Nick is famed for being one of the first investors in OpenSea.

Kyle Samani is the Co-Founder and Managing Partner @ Multicoin Capital, one of the leading crypto native funds of the last decade with positions in Solana, FTX, Fractal, and Helium to name a few.

In Today's Episode We Discuss:

1. Moving Away from a Shitcoin Casino:

  • What will it take for crypto to move away from being shitcoin casino?
  • Why does Nick believe that "crypto has been a free for all and greed got the better of people"?
  • Why does Nick believe that crypto shilling will reduce the amount of violence in the world?

2. FTX: The Biggest Ponzi Scheme in Plain sight:

  • How does Kyle reflect on SBF and FTX today? Should he have known it was a fraud?
  • How did Nick see so far ahead of time that SBF was not genuine?
  • What are the most striking lessons when comparing Coinbase's Superbowl advert to FTX's?

3. Where Politics and Crypto Collide:

  • SBF was one of the largest donors to Biden, what does this say about the rise of "crony capitalism"?
  • What candidates running in the election will be best for crypto?
  • Why will Trump win the election and be the first President to rule from a prison cell?
  • Why is the strategy pursued by Gensler and the SEC so flawed?

4. The Great NFT Comeback, The Crypto IPO Season:

  • What will be the next crypto company to IPO? When?
  • When will NFTs come back? What will cause this?
  • Will Opensea ever be worth $13BN again? What is their future?

Jan 4, 2024

Joining Harry in the hot seat today is Jason Lemkin, Founder @ SaaStr and one of the OG SaaS investors of the last decade. The discussion today is broken into two segments:

2023: A Year in Review:

  • Breakout company
  • Best early-stage fund
  • Best late-stage fund
  • Most surprising event
  • Founder of the Year

2024: Predictions: What is to Come:

  • Does the IPO window open?
  • Do Stripe, Databricks, and more go public?
  • What happens to early-stage venture markets?
  • Does the growth stage come roaring back?
  • What happens to the M&A market?
  • How does Trump change the startup ecosystem?
  • Will a generation of young VCs be washed out the system?
  • Will a ton of venture firms shut down?