20VC: Why VC Returns Will Get Worse, Why LP Incentive Structures are so Broken, What is the Answer to Liquidity with No M&A or IPOs, When to Sell vs Hold Your Winners & Turning $5M into $250M with The Trade Desk | Roger Ehrenberg, Eberg Capital

20VC: Why VC Returns Will Get Worse, Why LP Incentive Structures are so Broken, What is the Answer to Liquidity with No M&A or IPOs, When to Sell vs Hold Your Winners & Turning $5M into $250M with The Trade Desk | Roger Ehrenberg, Eberg Capital

Roger Ehrenberg is a legend of the venture industry as the Founder of IA Ventures, among the most successful seed-stage venture firms of this generation, having seeded companies including Datadog (NASDAQ: DDOG), Digital Ocean (NYSE: DOCN), The Trade Desk (NASDAQ: TTD) and Wise (LSE: WISE.L). Today Roger is the Founder and Managing Partner of Eberg Capital, a pioneer in bridging the gap among sports franchises, sports betting, media and entertainment. Roger’s current sports investments include stakes in the Miami Marlins, Real Salt Lake, Alpine Racing, Betr, Commonwealth, Kero Sports, Simplebet, SlamBall, Smarkets and WagerWire.

In Today's Episode with Roger Ehrenberg We Discuss:

1. The Commoditisation of Venture and Worsening Returns:

  • Why does Roger disagree with Doug Leone that "we have moved from a boutique high margin business to a commoditised low margin industry"?
  • Why does Roger believe we will see consistently worsening returns in venture?
  • Is this influx of LP capital cyclical or is it here to stay?

2. The New LPs and The Broken Existing LP World:

  • Why does Roger think the existing incentive structure for LPs is totally broken?
  • Who are the most important new LPs entering the venture market?
  • How do sovereigns and pension funds entering venture change the industry?
  • Which players have capitalised on this new LP class best?

3. Where Does the Liquidity Come From:

  • With the closed IPO window and lack of M&A, where will liquidity come from in the next 24 months?
  • Would a Trump administration open M&A markets? Does Roger agree M&A markets are shut down?
  • When does Roger believe IPO markets will open again? Will Databricks and Stripe go out in 2024?
  • If Roger were to run a continuity fund strategy, how would he structure it? What would he do?

4. When to Sell and When to Hold:

  • How does Roger advise managers on when to sell vs when to hold?
  • How important is it for a new firm to have a company go public in the first five years?
  • What are Roger's biggest lessons from selling The Trade Desk at a $2.5BN valuation?
  • How does Roger think about managers thinking they should manage the public book of their portfolio for their LPs? What are the pros and cons?

5. Relationship to Money:

  • Do rich investors make better investors? How does investing when you have a lot of cash already change your mindset around investing and exiting?
  • How does Roger analyse his relationship to money today?
  • What have been the single biggest needle movers in his wealth journey? How did it feel when he made a $6M bonus?

6. The Secrets to Parenthood and Marriage:

  • What does it mean to be a great father for Roger?
  • How does Roger think about bringing his children up with the same level of hunger and ambition, despite being brought up with such wealth?
  • What are Roger's two biggest lessons on the secret to a great marriage?

Avsnitt(1356)

20VC: The $BN Greenoaks Backed Protein Bar | Hitting $100M Revenues in David's First Year: Lessons & Mistakes | $0 to $600M: The Untold RXBAR Story | Product-Market-Fit, Pricing, Branding: What Every Founder Gets Wrong Today with Peter Rahal

20VC: The $BN Greenoaks Backed Protein Bar | Hitting $100M Revenues in David's First Year: Lessons & Mistakes | $0 to $600M: The Untold RXBAR Story | Product-Market-Fit, Pricing, Branding: What Every Founder Gets Wrong Today with Peter Rahal

Peter Rahal is the Co‑Founder & CEO of David Protein, the highest protein‑to‑calorie ratio for any protein bar on the market. Peter has raised over $85M from Greenoaks, Dr. Peter Attia and Dr. Andrew Huberman with the latest round valuing the company at $725 million. The company is poised for over $100 million in first‑year revenue. Formerly, Peter co‑founded RXBAR in his mom’s basement with a $10k start, growing it into a household brand and selling it to Kellogg for $600 million. poised for over $100 million first‑year revenue   Agenda for Today:  00:04 – The One Piece of Advice from My Father That Made $600M 00:07 – Selling Protein Bars from a CrossFit Gym to $2M in Year One 00:12 – Why Raising Money Early Would Have Killed RXBAR’s Success 00:15 – Product vs Brand: What Every Brand Gets Wrong Today 00:17 – Why Red Bull is the Best Brand in the World? What Can We Learn From It?  00:20 – Are Brands the New Religion? How Status and Community Really Work 00:27 – The Boiled Cod Stunt: Brilliant Marketing or Massive Waste of Time? 00:35 – Selling RXBAR for $600M: Inside the Decision and the TAM Ceiling 00:40 – $100M Overnight: What Really Changes When You Get Rich 00:44 – The Hidden Costs of Success: Health, Relationships and Obsession 00:47 – Why Peter Doesn’t Care What People Think… and Actually Likes Upsetting Them 00:53 – The $10B Plan for David: From Protein Bars to a Portfolio of Brands

8 Aug 1h 6min

20VC: Figma's 250% Pop - The Greatest IPO Mispricing Ever | Meta and Microsoft Blowout Quarters: Broken Down | Cognition Raises at $15BN and Ramp at $22BN | CRV Downsizing and What It Means for LPs and GPs

20VC: Figma's 250% Pop - The Greatest IPO Mispricing Ever | Meta and Microsoft Blowout Quarters: Broken Down | Cognition Raises at $15BN and Ramp at $22BN | CRV Downsizing and What It Means for LPs and GPs

Agenda: 00:00 – The Worst IPO Mis-Pricing Ever: What Really Happened at Figma 02:30 – Fidelity vs Founders: How Important is Fidelity When Going Public 07:00 – Why Founders Secretly Want a Pop, Even If It Makes Them Look Stupid 10:15 – The Truth Behind the $3B Figma "Left on the Table"  14:00 – Direct Listings vs IPOs: Should Figma Have Gone Direct  23:00 – CEO Compensation is Broken, Brian Halligan Doesn’t Hold Back 29:00 – The New Normal: Growth Rounds with Elon-Style Moonshot Packages 33:00 – Is Canva Next? Why Founders Should "Run, Forrest, Run" to the NASDAQ 36:00 – The Case for Going Public: VCs Are a Bigger Pain Than Public Markets 44:00 – Can AI Even Work for SMBs? Why No One’s Cracked the Code (Yet) 51:00 – Meta’s Monster Quarter: Growth, Cash Burn, and the Real AI Strategy 56:00 – CEO of the Year? Why Jensen Huang Leaves Zuck & Satya in the Dust 1:00:00 – Cognition's $15B Deal & Mass Layoffs: The Most Savage M&A Move of 2025 1:07:00 – Ramp’s $22B Raise: Genius Move or Suicide Round? 1:09:00 – CRV Shrinks, Benchmark’s Bet, and the Future of Venture Strategy

7 Aug 1h 20min

20Sales: $0-$3.7BN: The Databricks CRO’s Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

20Sales: $0-$3.7BN: The Databricks CRO’s Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

Ron Gabrisko is the Chief Revenue Officer at Databricks, where he joined in 2016. Under his leadership, Databricks has scaled from $0 to $3.7BN annualized revenue. He has grown the sales team from 0 to over 1,000 globally, leading expansion into enterprise, government, and international markets. Ron previously held senior sales roles at Cloudera and IBM, bringing deep experience in data and AI infrastructure. His tenure at Databricks has been defined by hypergrowth, multi-product adoption, and world-class GTM execution. Agenda for Today: 00:04 – The Databricks Origin Story: Ali, Ben Horowitz & 7 PhDs 00:08 – Ali vs JPMorgan: Turning Down $10M to Stay Cloud-First 00:13 – Prospecting Day: How Ron Scaled the GTM Culture 00:16 – Why Databricks’ Pricing Model Was Its Secret Weapon 00:19 – Enterprise vs SMB: The Risky Bet That Paid Off 00:23 – From $2M to $13M ARR: How Ron Built the First Sales Engine 00:29 – Can AI Replace Salespeople? Ron’s Brutally Honest Take 00:36 – How to Get Your First Million-Dollar Rep (and Keep Them) 00:42 – The Culture Secret Behind Scaling to 5,000 Sales Reps 00:45 – Why Databricks Waited Until $500M ARR to Go International 00:52 – What Makes a Great Sales Meeting? Ron’s Gold Standard 00:58 – The Snowflake Wars: Why Ron Says Databricks Is 5 Years Ahead

4 Aug 1h 15min

20VC: Inside Carnegie Mellon's $4BN Endowment | Why 90% of LPs Shouldn't Invest in VC | The $140BN Problem with Multi-Stage Funds | The Hidden Math Behind DPI, TVPI, and Illiquidity with Miles Dieffenbach

20VC: Inside Carnegie Mellon's $4BN Endowment | Why 90% of LPs Shouldn't Invest in VC | The $140BN Problem with Multi-Stage Funds | The Hidden Math Behind DPI, TVPI, and Illiquidity with Miles Dieffenbach

Miles Dieffenbach is Managing Director of Investments at Carnegie Mellon University, where he helps oversee a $4 billion endowment with a focus on venture capital, private equity, and alternative investments. Under his leadership, CMU’s private book has remained self-funding during some of the toughest years for liquidity.  Agenda for Today: 00:04 – "I Had Cancer at 26 – It Changed Everything" 07:00 – Inside the $4BN Carnegie Mellon Endowment: The Investment Blueprint 10:45 – Are LPs Getting Screwed in Venture? 13:30 – 90% of LPs Shouldn’t Be in Venture – Here’s Why 16:00 – Seed Funds Are a Trap (And No One Wants to Admit It) 20:00 – The $140BN Problem with Multi-Stage Funds 24:00 – "Index Is the Best in the Game – Here's Why They Win" 29:30 – "The Dirty Secret of LPs: Brand Over Performance" 34:30 – "When Founder-Friendly Goes Too Far" 38:00 – "The OpenAI Bubble – Will It All Go to Zero?" 44:00 – "Ping Pong Diligence & Wildest Fundraising Stories"

4 Aug 1h 27min

20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

Agenda: 00:00 - Why Benchmark Is Bleeding Partners (and Why That’s the New Normal) 04:57 - “I Wouldn’t Leave Benchmark… Unless I Had THIS” — Jason on Brand vs Autonomy 09:01 - The Rise of the Solo GP & The Death of LP Conventional Wisdom 13:50 - The Unstoppable Force of Elad Gil & The Myth of LP Discipline 18:45 - Is Vibe Coding the New SaaS? Jason’s $10K/Month Spend Reveal 26:57 - Cursor’s Growth Is Insane—But Is It Sustainable? 31:44 - Will Microsoft, Google, or Amazon Win the AI Infra War? 37:42 - Is GitHub Copilot the Biggest Miss in Microsoft’s History? 44:15 - Are Big Tech Incumbents Now Too Powerful to Fail? 48:00 - Apple’s AI Problem: Is It Time for a Management Overhaul? 52:30 - Figma’s IPO: $30B Return, Zero Hype. What Happened? 1:06:00 - Final Bets: Cursor to $4B ARR, Lovable to $400M ARR, OpenAI to $800BN?

31 Juli 1h 21min

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

Martin Casado is a General Partner @ a16z where he leads the firms $1.25BN infrastructure fund. At a16z, Martin has led investments in companies like Cursor, dbt Labs, and Fivetran to name a few. Before joining a16z, he co-founded Nicira, acquired by VMware for $1.26B. At VMware, he served as CTO of Networking. Widely regarded as a visionary in enterprise infrastructure, Martin has helped shape the modern cloud computing stack. Agenda: 00:00 – Analysis of Current AI Investment Landscape 04:45 – Will Anthropic Kill the AI App Layer? 09:20 – “The Oligopoly Is Coming—Just Like Cloud” 12:50 – Are AI Models Actually Terrible Venture Investments? 15:40 – Why it is BS to Put Down AI Apps for Having Temporary Revenue 21:30 – “Open Source Is a National Security Weapon—And We're Losing” 26:40 – “Have the Foundation Models of the Future All Been Founded Already” 34:30 – Why it is BS to Denigrate AI Apps for Having Low Margins 38:40 – Does AI Make 1x Engineers 10x or 10x Becomes 100x 44:10 – “We’re All Dead Wrong About AI and Job Loss” 50:30 – “The Only Sin in Venture: Backing the Wrong Winner” 55:10 – What People Think They Know About Wealth But Do Not

28 Juli 1h 10min

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

Fernando Fanton is one of the most respected product leaders in Europe, having held Chief Product Officer roles at Monzo and Just Eat. He previously led product and tech at Rappi, one of Latin America's most valuable startups. Today, Fernando is the CPO @ Property Finder; one of the biggest breakout unicorns from MENA.  Agenda: 00:00 – Is “having a vision” actually killing great product teams? 03:15 – Why do most products suck—and what separates the great ones? 07:20 – Should we kill the PM role entirely? Fernando says maybe. 11:45 – Is Monzo’s obsession with trust more powerful than speed? 16:10 – What’s the #1 reason internal tools will never replace SaaS? 21:00 – Will AI wipe out the need for designers and PMs? 26:30 – Is it arrogant for product teams to protect users from “bad” choices? 32:15 – What’s the future of product when OpenAI controls the whole stack? 37:40 – What Monzo product blew up—and why no one saw it coming? 42:55 – Can a bank built on principles really become a $100B company?

27 Juli 1h 7min

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

Agenda: 00:00 – Did Jason Just Kill Replit?  03:45 – Why Claude Lies To You and Cannot Be Trusted 06:50 – You Cannot Trust Agents. Period. 10:20 – Why Windsurf Was Dead Without Claude 12:30 – Cursor vs. Lovable: What’s the Better Bet? 14:40 – Should You Still Invest in Cursor at $28B? 18:05 – Would You Bet on Anthropic at $100B or OpenAI at $300B? 24:15 – Inside OpenAI’s Secret Weapon: The Calvin French-Owen Memo 27:50 – Perplexity Just Crushed ChatGPT and Claude 32:15 – Will Cursor Build Their Own Models Before Anthropic Cuts Them Off? 33:20 – Figma’s IPO at $16B: Outrageous or Fair Game? 41:55 – 90% of Seed Funds Are Cooked—Is Rob Go Right? 52:15 – How Often Do You Meet a Founder Who Can Return the Fund? 1:08:00 – Which Seed Fund Would You Back Today?

24 Juli 1h 21min

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