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

Latest Episodes:

20VC: Tiger Global Saved by OpenAI | Coatue's New Fund: Hype or Substance | Why SBF is the Greatest Investor of the Last 5 Years | Why Big Funds are Investing in Perplexity May 15, 2025

Show notes

Items Mentioned in Today's Episode:

04:11 Owner's New $120M Round at $1BN

06:05 Why Series A is F****** Today

14:55 Could Tiger Global Be Saved by OpenAI and Scale

22:43 Why SBF is the Greatest Investor of the Last Decade

31:34 Why No Individuals Should Invest in Venture Funds

36:27 Why Microsoft Laying 3% of Their Workforce Off is not Enough

41:38 OpenAI's New CEO: Non-Technical CEOs Running OpenAI

44:48 Why Big Funds are Investing in Perplexity

54:43 Why Clay Should Raise a Warchest and Go to War

01:00:05 The Impact of AI on Marketing and Sales

20VC Exclusive: Mercury Founder Launches First $26M Fund | Why Founders Should Take the Highest Price | Why Serial Entrepreneurs are Better | Why AI Is So Overhyped | The Future of Venture Capital with Immad Akhund May 12, 2025

Show notes

Immad Akhund is the CEO of Mercury. Launched in 2019, Mercury has raised $500M in funding from Sequoia, Coatue, CRV, Andreessen Horowitz and others. He is a former part-time partner at Y Combinator and is an active angel investor, with more than 350 investments in startups including Rippling, AirTable, Rappi, Applied Intuition, and Substack.

In Today's Episode We Discuss:

04:38 Exclusive News: New Fund Announcement

05:15 Lessons from 350 Angel Investments

12:27 Why Founders Should Always Push for the Highest Price

14:40 Biggest Wins and Misses in Angel Investing

22:56 How Sequoia Came to Lead the Series C for Mercury

31:32 Why Move From Angel to VC

33:41 Is It Wrong For Founders to Also Have Funds with LP Capital?

36:28 AI Investments: Overhyped or Worthwhile?

41:14 Raising a First Time Fund: Challenges & Surprises

49:47 The Future of Venture Capital

54:36 Quickfire Questions and Reflections

20VC: Four Traits of the Most Successful Founders | How to Hunt and Close Talent Like a Pro and Where All Founders Go Wrong | Lessons Raising $397M From the Best Investors in the World with Eléonore Crespo @ Pigment May 09, 2025

Show notes

Eléonore Crespo is the Co-Founder and CEO @ Pigment, one of Europe's fastest-growing companies. With Pigment, Eleonore has raised over $397M from the best in the world including ICONIQ, Greenoaks and IVP to name a few. Prior to Pigment, Eléonore was on the other side of the table as an investor with Index Ventures.

In Today's Episode We Discuss:

[04:10] "I had 3 surgeries. That's when I knew I had to become a founder."

[06:50] Why Index Ventures isn't on her cap table

[08:40] Eleonore's CIA-style co-founder hunt (she literally made a target list)

[11:50] Co-CEOs: "We talk 3x a day. That's our superpower."

[13:30] The boutique coffee metaphor for product excellence

[15:40] Yuri Milner's 4 traits of legendary founders (one is shocking)

[17:30] "Hiring is everything. I hunt talent like a football scout."

[19:00] Wild Olympic Games story → led to hiring a top CFO

[24:50] How she filters out title-chasers and political hires

[29:30] "Too much process? I make teams list the dumbest ones."

[33:00] Her blunt answer on whether Europe can produce scale execs

[35:00] Why she raised so much money… even when they didn't need it

[38:50] Board power is real: "They can fire you. I've seen it."

[43:30] Rob Ward's counter-cyclical advice: double down during a downturn

[44:50] "We closed a massive US deal… at 2am… while drenched in rain."

[47:10] Selling into the US as a European founder—her full playbook

[50:20] The hardest part of being a CEO no one talks about

[54:00] "Children remind you what happiness is."

[56:30] "I don't fast. That would make me unhappy." On longevity culture

[59:20] Why her husband knows nothing about Pigment

[01:04:20] "Forget $50B. I want to build a $200B company."

Follow Eleonore Crespo

LinkedIn: Eleonore Crespo
Pigment: pigment.com

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Please read the offering circular and related risks at invest.modemobile.com. This is a paid advertisement for Mode Mobile's Regulation A+ Offering. Past performance is no guarantee of future results. Investing in private company securities is not suitable for all investors because it is highly speculative and involves a high degree of risk. It should only be considered a long-term investment. You must be prepared to withstand a total loss of your investment. Private company securities are also highly illiquid, and there is no guarantee that a market will develop for such securities. DealMaker Securities LLC, a registered broker-dealer, and member of FINRA | SIPC, located at 105 Maxess Road, Suite 124, Melville, NY 11747, is the Intermediary for this offering and is not an affiliate of or connected with the Issuer. Please check our background on FINRA's BrokerCheck.

20VC: Benchmark vs a16z: Why Stage Specific Firms Win | Windsurf Sells For $3BN | Decagon Raises at 100x ARR | Do Mega Funds Win the Future of VC | What Does Harvard's Losing Their For-Profit Status Mean for VC May 07, 2025

Show notes

Today's Topics:

04:44 Analysis of $3 Billion Windsurf Acquisition

12:39 Will Mega Funds Win the Future of Venture Capital

18:39 Does Every Fund Have to do Pre-Seed to Win Series A and B Today

27:53 Why AI Will Create Massive Unemployment

31:06 The $100,000 Bet on the Future of Work

35:52 Why Venture Has Become a Bundled Good

37:52 Why Stage Specific Firms Will Win: a16z vs Benchmark

40:16 What Does Harvard Losing It's For Profit Status Mean for Venture

42:57 Why AI is Maiming and Not Killing Growth Companies on the Path to IPO

45:41 Decagon Raises 100x ARR: The Breakdown

52:50 Why VCs Are Upside Junkies and What That Means Today

01:03:37 Olo Looking to Sell: What Happens When Public Companies Want to Sell

20VC Exclusive: Why Mega Platforms Will Win in VC | Why You Cannot Do VC If You Do Not Do Pre-Seed | Why Market Sizing is BS | Where Will Foundation Models Build/Buy Apps vs Where Will They Not with Bucky Moore May 05, 2025

Show notes

Bucky Moore is a Partner @ Lightspeed Venture Partners, announced exclusively in the show today on 20VC. Prior to Lightspeed, Bucky spent an incredibly successful 7 years at Kleiner Perkins working with Mamoon Hamid to build one of the most successful early stage firms of the last decade. Bucky has made investments in the likes of Prisma, Netlify, Browserbase and more.

In Today's Episode We Discuss:

03:07 Big News: Joining Lightspeed Venture Partners

04:09 Why Mega Platforms Will Win the Next 10 Years of VC

09:33 Are Foundation Model Companies Good Venture Investments

16:04 What Applications Will Model Providers Buy/Build? What Will They Not?

22:03 How to Approach Price Sensitivity in a World of AI

28:25 Why is it BS to do Market Sizing When Making Investments in AI

34:03 Is the Future of VC Domain Specialization

38:38 How to Know What Company Wins in Super Competitive Markets

41:06 Why Every Firm Has to do Pre-Seed To Win in VC Today?

44:43 The Risks of Multi-Stage Investing: Is Signalling Risk Real?

48:53 Investing Lessons from Leading Rounds in Glean and Windsurf

56:54 Quick Fire Round: Lessons from Mamoon, Fave CEO, Next 10 Years

20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI May 02, 2025

Show notes

Reggie Marable is the Head of Global Sales at Sierra, a conversational AI platform for businesses. Sierra enables companies like ADT, Sonos, SiriusXM, and WeightWatchers to build AI agents that transform customer experiences. The company has rapidly become a hypergrowth leader in Silicon Valley, recently securing a funding round that values it at $4.5 billion. Before joining Sierra, Reggie was the Head of Sales in North America at Slack and the Area Vice President of Enterprise Sales at Salesforce.

In Today's Episode We Discuss:

02:50 "What I Learned from Failing Early as a CRO"

06:06 The Most Effective Sales Strategy and the BS Sales Methodology

06:55 How to Build Sales Processes from Scratch

12:28 When and How to do Verticalised Sales Teams

14:15 How to Become World Class as Sales Prospecting and Outbound

17:21 How to Use Proof of Concepts to Win Enterprise Deals

22:04 Enterprise vs. Self-Serve: Both or One and How

30:09 Building a Sales Team from Scratch

37:39 Structuring the Hiring Process

41:14 How Founders F*** Up Hiring in Sales

46:25 Handling Salary and Title Expectations

51:36 How to Run Effective Deal Cycles

57:06:07 How to do Onboarding for New Sales Hires

59:07:48 How to do Post Mortems in Sales Processes

01:04:24 Negotiating Enterprise Deals

01:08:04 Quick Fire Round: Sales Tactics and Strategies

This episode is brought to you by Capchase, helping software and hardware companies close deals while accessing TCV upfront. Learn more at capchase.com/20vc.

20VC: Why Fund Returners Are Not Enough Anymore | Why Sequoia Had the Best Strategy at the Worst Time | What it Takes to Be Good at Series A and B Today | Benchmark Leads Manus Round: Should US Funds Invest in Chinese AI May 01, 2025

Show notes

In Today's Episode We Discuss:

03:56 Why The Risk Lever Has Been Turned Higher than Ever in VC

06:04 Why IRR is the Hardest Thing to Control

09:36 Is Lack of Liquidity Short Term Temporary or Long Term Structural

12:17 Why Fund Returners Are Not Good Enough Anymore

16:03 Sequoia: The Best Strategy at the Worst Time

26:30 What it Takes to be Good at Series A and B Today

34:14 Only Three Company Types Survive AI

41:35 ServiceNow: 25% Pop, WTF Happened

45:29 Palantir and SAP Ripping: Do Incumbents Win AI

49:43 Are Benchmark Wrong to Invest in Chinese Made Manus

01:00:52 Geopolitical Risks in Investments

01:11:36 European vs. US Tech Culture

20VC: VCs are Spreadsheet Monkeys and are Commoditised | Why Fees and Carry Misalign GPs and LPs | Why Founders Will Realise Multi-Stage Funds Damage Seed Rounds | Why We Need European Sovereignty More Than Ever with Taavet Hinrikus Apr 28, 2025

Show notes

Taavet Hinrikus is a Partner at Plural, the early-stage fund that backs the most ambitious founders on a mission to change the world through technology. He co-founded Wise in 2010, where he was CEO and later Chairman, which went public in the first-ever direct listing in Europe in 2021. Prior to that, Taavet was Skype's Director of Strategy until 2008, having joined as its first employee. He's been an active investor for more than a decade,with personal investments in the likes of Bolt and Synthesia.

In Today's Show We Discuss:

04:08 VCs are Spreadsheet Monkeys

05:41 Why Banker European VCs Suck More Than The Others

11:20 Why Serial Entrepreneurs Are Better

14:48 Why the 2:20 Fee and Carry Model in VC is Broken

18:01 What are the Biggest Ways VC Investment Decision-Making is Broken

28:26 Why is it BS when VC Firms Need Every Partner to Meet the Founder

31:24 When and Why Will Founders Realise Multi-Stage Firms are Bad Early Investors

34:35 Why Does Europe Need to Build it's Own Tech Now More Than Ever

37:24 Will Putin Invade More European Countries

39:29 What are the Dangers of Having US Made Tech in Europe

47:12 How Does the Change in Relationship Between the US and Europe Impact How We Build Our Tech Ecosystem?

52:36 Quick Fire Questions and Reflections

20Growth: Inside Kraken's $1.5BN Growth Playbook: What Works, What Doesn't and What No Founders Understand About Growth That Will Change Their Company with Mayur Gupta Apr 25, 2025

Show notes

Mayur Gupta is currently the CMO at Kraken, one of the largest crypto platforms in the world. Prior to that, he lead Marketing, Business Transformation and Growth at Gannett - USA Today Network, led Growth at Spotify and was the CMO at Freshly which eventually got acquired by Nestle. He was the first ever Chief Marketing Technologist at Kimberly Clark.

In Today's Episode We Discuss:

03:25 Biggest Growth Lessons from Spotify

08:21 Role of Marketing in Product-Led Companies

13:35 How to Build a Growth Engine

20:40 Organic vs. Paid Growth Strategies

27:36 The Branding Dilemma: Performance vs. Brand Marketing

28:37 Creating Demand: The Role of Upper Funnel Marketing

29:35 Balancing Investment: Immediate vs Long Term Bets

30:03 Channel Saturation and Experimentation

31:42 Growth Strategies and Performance Metrics

34:54 Growth: Big Swings or Moving % Points

40:04 Successful Growth Experiments and Tactics

44:56 Quick Fire Questions and Final Thoughts

20VC: OpenAI's $3BN Acquisition of Windsurf: The Breakdown | Are Endowment Funds F******* & How LP Deployment to Venture Will Change in 2025 | Why Revenue Multiples are BS, The Rise of AI Rollups and Multi-Stage Funds Destroying Seed Investing Apr 24, 2025

Show notes

In Today's Show We Discuss:

04:49 Breaking Down the $3BN Windsurf Acquisition

06:18 Why Sam Altman is Playing a Master Game

12:40 Why Multi-Stage Funds are Destroying Seed Managers

21:52 Are Endowment Funds F******

27:38 What Would Rory Do If He Was CFO of an Ivy League Endowment Fund

43:38 The Denominator Effect and It's Impact on Venture Allocations

49:36 Why Revenue Multiple is BS & What You Need to Know

51:34 The Rise of AI Rollup Plays & Are They Good Businesses

55:29 Competitive Markets: How to Make Money in Them?

01:02:58 Why If You Can Guarantee 5x, You Should Always Do the Deal