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











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Now displaying: October, 2023
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?

Oct 25, 2023

Ely Lerner is an EIR at Reforge and an advisor for startups transitioning from traction to hypergrowth. Previously he was Head of Consumer Product at Chime, and before that spent an incredible 8 years at Yelp in a number of different roles including Head of Product at Eat24, and Product Leader/GM at Yelp.

In Today's Episode with Ely Lerner We Discuss:

1. Entry into Growth:

  • How did Ely make his way from engineering manager to growth leader?
  • What are a couple of his single biggest takeaways from his time with Yelp and Chime?
  • Why do employees in large companies have to have P&L ownership when innovating within the larger company they are in?

2. Advisors: What, When and How:

  • What are the three different types of advisors founders can work with today?
  • When is the right time to engage with each of them?
  • Should the advisor have had direct experience with the problem you need help with?
  • How should these advisors be compensated; what is normal?
  • What are 1-2 of the biggest reasons startup advisory roles do not work out?

3. Offense vs Defence: The Tricky Balance:

  • What is the difference between offense and defense in product strategy?
  • What should the resource allocation be between the two?
  • What is the right amount of offensive strategies to have on at the same time?
  • How can leaders prevent their defensive teams from feeling like second-class citizens?

4. Ely Lerner: AMA:

  • Why does Ely disagree with many and suggest that horizontal products do have a core ICP?
  • Should growth teams sit on their own or within functions in the org?
  • What are the core reasons teams fail to ship fast?
  • What state should your data be in when you bring in your first growth hire?

Oct 23, 2023

Matthieu Rouif is the Co-Founder and CEO @ PhotoRoom, one of the fastest-growing YC companies having scaled to an astonishing $50M in ARR in just 3 years. Their capital efficiency is immense having scaled to $20M in ARR on just $2M of invested capital. Prior to founding PhotoRoom, Matthieu founded several start-ups, including an app for ski resorts, HeyCrowd, and Replay, a video editor which was ultimately acquired by GoPro. Whilst at GoPro, Mattheiu led all image editing products.

In Today's Episode with Matthieu Rouif We Discuss:

  1. From GoPro to One of YC's Fastest Growing Companies:

  • How did Matthieu make the move from GoPro to founding PhotoRoom?
  • What are the big mistakes Matthieu made on prior companies that he did differently with PhotoRoom?
  • What does Matthieu know now that he wishes he had known when he started PhotoRoom?

2. Scaling to $20M in ARR with $2M of Cash:

  • What allowed Matthieu and PhotoRoom to be so capital-efficient in their scaling?
  • What are the biggest mistakes founders make when it comes to resource allocation and capital efficiency?
  • On reflection, what did Matthieu not spend money on that he wishes they had spent money on?

3. Consumer Subscription + Photo Editing: Is it a Good Business:

  • What are the customer acquisition costs by channel for PhotoRoom?
  • What are their payback periods on a per-customer basis?
  • How can it be a good business when the churn rate annually is 30-40%?
  • How does this space play out with Canva, Adobe, Veed, Kapwing? Who wins?

4. The Future of AI:

  • Who wins; incumbents or startups?
  • What matters more; data size or model size?
  • Will UI be more or less important in an AI-first world?
  • Why does Matthieu believe that everyone hates command line prompts?
  • Will we see $BN revenue companies created with just 10 people?

Oct 20, 2023

Harry Stebbings is the Founder of 20VC, building the next great financial institution at the intersection of media and venture capital. 20VC has reached over 125M downloads in 100+ countries and has featured the likes of Doug Leone, Bill Gurley, Marc Benioff, Daniel Ek and more. On the investing side, Harry has raised over $400M and made investments in the likes of Pachama, Linear, TripleDot, Superhuman, AgentSync, Linktree, Sorare and more.

In Today's Episode We Cover:

  1. Are LPs Open for Business:

  • How has what LPs look for in new manager investments changed?
  • What type of funds will be able to raise? Which will not be able to raise?
  • What can managers do to significantly increase their chances of raising a new fund?

2. The Seed Investing Landscape: Harder Than Ever

  • Why is seed pricing as high as ever?
  • Why are multi-stage funds more active in seed than ever? How does this impact seed?
  • How will seed change and evolve over the next 6-12 months?

3. Series A + B: The Best Place to be Investing

  • Why is Series A the best risk/reward insertion point when investing today?
  • How has the competition level at Series A and B changed?
  • What do many people not see or know about this stage of the market today?

4. Is Growth Dead: Are Growth Deals Getting Done:

  • What two core elements are needed if you want to raise a growth round today?
  • How have growth round valuations been impacted over the last 12 months?
  • To what extent do founders need to change their expectations on the price of rounds they will be able to get done today?

5. M&A and IPOs: Tough Times Ahead

  • Why will we see continued low levels of activity in M&A markets?
  • What acquisitions are we seeing take place?
  • When will the IPO window crack open?
  • Why were Klaviyo, Instacart and Arm not enough to open the windows?

Oct 18, 2023

Beezer Clarkson leads Sapphire Partners‘ investments in venture funds domestically and internationally. Beezer has invested in some of the best firms of a generation including USV and Point Nine to name a few. Beezer began her career in financial services over 20 years ago at Morgan Stanley in its global infrastructure group. Prior to joining Sapphire in 2012, Beezer managed the day-to-day operations of the Draper Fisher Jurvetson Global Network, which then had $7 billion under management across 16 venture funds worldwide.

In Today's Episode with Beezer Clarkson We Discuss:

  1. LP Landscape: WTF is Going On:

  • Are LPs really all closed for business?
  • What has changed in what LPs want to see from managers they are looking to invest in?
  • What has changed about the size and pace of new commitments for LPs?
  • Are all LPs moving away from growth?

2. 2020-2022: Years in Review:

  • Are LPs frustrated by managers who reduced deployment timelines to 12-18 months?
  • Are LPs frustrated with managers who did not take liquidity when they could have done?
  • How does Beezer advise managers on when and how to take liquidity in their best positions?
  • Are managers accurately marking their portfolios to their LPs today?
  • Why does Beezer believe the incentive mechanism for LPs is broken today in many ways?

3. How To Build a Top Decile Firm:

  • Why does Beezer believe if you want to have the best returns, you have to have one company that returns the fund? Can you not do it with multiple half-fund returners?
  • Is ownership core to all the best firm's top performance? Is it the size of outcome or the size of ownership that drives the best performance across the board?
  • What does data show on how the best funds take significant risk? What are their loss ratios?
  • What are the core tradeoffs to Beezer between scaling AUM and providing top decile returns?

4. LP Markets: The Times They are a Changing:

  • Does Beezer believe LPs will remain cold on large $1BN+ growth firms?
  • Which segments of the market are hot? Which are cold?
  • What are the most significant changes we will see in the LP markets moving forward?
  • Is today the new normal or are we in a downturn that we will come out of?


Oct 16, 2023

Matthew Prince is the co-founder and CEO of Cloudflare, on a mission is to help build a better Internet. Matthew has scaled Cloudflare to over $1BN in revenue, $20BN in market cap, and over 3,200 employees. Today the company runs one of the world's largest networks, which spans more than 200 cities in over 100 countries. Matthew is a World Economic Forum Technology Pioneer, a member of the Council on Foreign Relations, winner of the 2011 Tech Fellow Award, and serves on the Board of Advisors for the Center for Information Technology and Privacy Law.

In Today's Episode with Matthew Prince We Discuss:

1. From Selling Fireworks to Public Company CEO:

  • How did Matthew first make money selling fireworks as a kid?
  • Does Mathew believe in the trope "you have to love what you do"?
  • What does Matthew know now that he wishes he had known when he started Cloudflare?

2. Money, Identity and Happiness:

  • Why does Matthew feel many of the most successful founders lose their way when they leave their companies? How does he assess Gates, Bezos and others?
  • Does Matthew tie his own identity to Cloudflare and the success of the company?
  • How does Matthew evaluate his own relationship to money today? How has it changed over time?
  • How does Matthew keep score today on how he is doing? What is success to Matthew?

3. The Three Outcomes for Companies Today:

  • What are the three outcomes available to companies today?
  • What is the worst and why?
  • What are the two biggest mistakes Matthew sees founders make today?
  • Why does Matthew know that diverse teams are more successful? What is the proof?
  • What is Matthew's single biggest advice to founders when it comes to selecting a co-founder?

4. Focus is BS: You Have to Have Mega Ambition:

  • Why does Matthew believe it is BS to have a very specific target customer from the offset?
  • What does Matthew believe are the benefits of not having an ICP in the early days?
  • What are the biggest pieces of VC advice to founders that Matthew knows to be wrong?

Oct 12, 2023

Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade with a portfolio including Lemonade, Melio and HoneyBook, just to name a couple of Aleph’s unicorns.

Adi Levanon is the Founder & Managing Partner @ Selah Ventures, a solo-GP-founded venture fund investing $500k checks into AI-based solutions that enhance financial services, healthcare organizations, fintechs, and SMBs, with a focus on founders in the US and Israelis globally.

In Today's Episode on Israeli Resilience We Discuss:

  1. Where are we at today? What is it like on the ground, today?
  2. Have the international community reacted as expected? What more can be done?
  3. What does it mean to be called up for "reserve"?
  4. How are companies dealing with 25% of their teams being called into the armed forces?
  5. Are VCs investing still? Does work carry on?
  6. Whose reactions are exemplary and we should look to follow?
  7. Whose have been woeful and should be called out?
  8. What are the single biggest misconceptions of the situation?
  9. What can people do to help? What can be done?

Oct 11, 2023

Deven Parekh is a Managing Director at Insight Partners, one of the leading investing franchises of the last 25 years. Deven has made more than 90 investments since joining in 2000 including in the likes of Twitter, Alibaba,, Chargebee and Automattic (WordPress) to name a few.  

Woody Marshall is a General Partner @ TCV, one of the most successful growth funds of the last decade with a portfolio including the likes of Facebook, AirBnB, Spotify, LinkedIn and many more incredible companies.

Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. 

In Today's Episode We Discuss:

1. The Growth Landscape Overview:

  • Is growth dead? Are any growth deals getting done?
  • How has the price changed for growth deals that are getting done?
  • Which type of growth companies will vs will not be able to raise?
  • What happens to all of the growth companies with $300-$500M in cash but little revenue?

2. The Great Reset: Valuations Need to Change:

  • Why should companies be actively resetting their valuations? What are the benefits?
  • What will happen between VCs and LPs when there is no incentive for VCs to reset their portfolio valuations when they need to go out and raise from those same LPs?
  • Structure is often part of these valuation resets, is structure to rounds always bad? When is it good? What type of structure is acceptable vs unacceptable?

3. Are the Public Markets Creeping Open:

  • Should we take comfort from ARM, Instacart and Klaviyo and assume the public markets are going to open again? If not, what will cause them to open?
  • How should we analyze the performance of the IPOs above? Many have been negative, are they right to suggest this is not the response we wanted?
  • Why does Woody believe, like Instacart taking a 75% discount to their last round, we should have more and more companies go public at discounts to their last private round?

4. Late Stage Growth is Dead and Revenue Multiples:

  • Why is late-stage growth dead? How long do we think this will last?
  • How should we assess revenue multiples today? New normal? Same as always? How will revenue multiples look in 12 months from now?
  • How should we analyse the large late stage growth rounds for hyped AI companies? What happens there?

Oct 9, 2023

Scott Farquhar is the Co-Founder & Co-CEO @ Atlassian. Scott co-founded the company with his university friend, Mike Cannon-Brookes, in 2002 from Australia. Over an incredible 20-year journey they have grown to a market cap of $50BN today, over 11,000 staff globally and serving over 260,000 customers. Scott is also a co-founder of Skip Capital, a private investment fund with a portfolio including Figma, Snyk, Canva and more.

In Today's Episode with Scott Farquhar We Discuss:

1. The 20-Year Journey to $50BN Market Cap:

  • How did Scott first make his way into the world of tech and come to co-found Atlassian?
  • What does Scott know now that he wishes he had known at the beginning?
  • From 20 years with Mike, what is Scott's biggest advice on choosing your co-founder?

2. The Fundraising Masterclass with Atlassian:

  • An emergency phone call, a honeymoon cut short; how did the first funding round for Atlassian come to be? Where was the business revenue-wise at the time?
  • Why did Scott not like the traditional fundraising process? What did he do to add game theory and ensure that they got the best deal as a company?
  • Why did Scott choose Accel with their offer? How did Peter Fenton lose a $3BN deal with Atlassian?

3. Lessons Scaling Atlassian to $4BN in Revenue:

  • What does Scott believe are the 4 core roles of the CEO? Is resource allocation the most important?
  • What are the single biggest acts of commission and omission that Scott regrets?
  • What are the biggest lessons Scott has from shutting down Stride, their Slack competitor?

4. Scott: The Father, Husband and Philanthropist:

  • What does great fatherhood mean to Scott today?
  • What is the secret to a truly successful marriage?
  • How does Scott assess his relationship to money today? How has it changed with time?
  • How does Scott think about bringing children up in a world of affluence and abundance?

Fun Fact: Every single 20VC episode is recorded with Riverside.FM. It is the one product that I could not live without. Try it today here ( and use the code 20VC for 15% off.

Oct 6, 2023

Guillermo Rauch is the Founder and CEO @ Vercel, giving developers the frameworks, workflows, and infrastructure to build a faster, more personalized Web. To date, Guillermo has raised $312M from Accel, Bedrock, Greenoaks, GV and more. Prior to founding Vercel, Guillermo co-founded LearnBoost and Cloudup where he served the company as CTO through its acquisition by Automattic in 2013.

In Today's Episode with Guillermo Rauch We Discuss:

1. From Argentina to SF: The Boy Making Money Online:

  • How did Guillermo first get into computers and start making money online?
  • Does Guillermo still believe the US and SF offers the same opportunities it did when he came?
  • Did Guillermo feel the weight of responsibility of providing for his family at a young age?

2. Timing, Markets and Narrative Violations:

  • Why does Guillermo believe it does not matter being first but being right?
  • Why does Guillermo believe the most important thing for a company is market selection?
  • Why does Guillermo believe it is crucial that founders and companies have "narrative violations"?

3. The Future of AI:

  • What model will win in the future; open or closed?
  • Where does the value accrue; startups or incumbents?
  • How will the SaaS business model change in a world of AI?

4. Silicon Valley's Most Successful Angel You Did Not Know:

  • What are some of Guillermo's biggest lessons from angel investing?
  • What is his single biggest miss? How has it changed how he thinks?
  • What have been his biggest hits? How did they impact how he thinks about what it takes to win?

Oct 4, 2023

Matt Rosenberg is Grammarly’s Chief Revenue Officer and Head of Grammarly Business. He leads all B2B revenue, operations, and growth for Grammarly Business, Grammarly for Education, and Grammarly for Developers. Previously, as CRO of Compass, he took the company into the Fortune 500 and contributed to a more than eightfold increase in business growth. Prior to Compass, Matt served as Eventbrite’s CRO leading them to become the largest event platform in the world by event count.

In Today's Episode with Matt Rosenberg We Discuss:

1. From Miserable Lawyer to World Beating Sales Leader:

  • How did Matt make the transition from lawyer to sales leader?
  • What does Matt know now that he wishes he had known when he started in sales?
  • What are Matt's biggest pieces of advice for anyone who wants to make a career change and is lacking confidence?

2. The Playbook and Hiring The Team:

  • How does Matt define the "sales playbook"?
  • Should the founder be the one to create and execute V1 of the playbook?
  • Should the first sales hire be a rep or a sales leader?
  • When is the right time to make that all-important first sales hire?

3. Discounting, Champions and Urgency:

  • What can sales team do to create urgency in deal cycles? What works? What does not?
  • How does Matt approach discounting? When to do it vs when not to? What level is acceptable?
  • What are the biggest secrets to creating champions within prospects?
  • Why does Matt believe that deals are won and lost in prospecting?

4. Developing Great Sales Talent:

  • How does Matt use sales call recordings to train teams? What is his 3x3 matrix for coaching calls?
  • What is a good reason to lose a deal vs a bad reason? How does Matt do deal reviews?
  • What are the single biggest elements sales leaders can do to nurture sales talent?
  • What are the biggest mistakes sales leaders make when developing talent internally?

Oct 2, 2023

Phin Barnes is the Co-founder and Managing Partner of The General Partnership (TheGP), a venture capital firm that’s redefining what partnership means for founders. Previously, Phin spent over a decade at First Round Capital, where he was responsible for over 60 investments including Blue Apron, Notion, Clover Health, Gauntlet and Persona. Before First Round, he created an independent video game company and before that was an early employee at AND 1 Basketball where he helped scale the brand from $15 to $225 million in revenue and served as the Creative Director for Footwear.

In Today's Episode with Phin Barnes We Discuss:

  1. From Creative Director to Venture Capitalist:

  • How did Phin make his way into the world of venture having been a Creative Director at a basketball brand?
  • What does Phin know now that he wishes he could tell himself on his first day in venture?
  • What are 1-2 of Phin's biggest lessons from his 10 years at First Round which shapes how he invests?

2. The Venture Capital Model is Broken:

  • Why does Phin believe the current services model of venture is broken?
  • Do the best founders need your help?
  • What have been some of the biggest lessons in what the best founders want from their VCs?
  • What happens to this generation of firms with massive support teams?
  • Do VCs use these support teams merely to justify massive fund size scaling to LPs?

3. The Venture Landscape Today:

  • How can we compete in a seed landscape of $5M on $25M against large multi-stage firms?
  • What founders types are attracted to big brands? What founder profiles are taken in by large rounds and high prices?
  • Is Phin more or less excited about seed-stage investing now than he has been before?

4. Investing Lessons 101:

  • What is Phin's biggest hit? How did seeing their success impact his mindset?
  • What is Phin's biggest loss? How did the loss impact how he views investing?
  • Traction, team, market; how does Phin rank the three in prioritisation?
  • What should all young people know when entering the venture landscape?