20 VC 063: What It Takes To Standout In A Crowded Market with Ezra Galston @ Chicago Ventures

20 VC 063: What It Takes To Standout In A Crowded Market with Ezra Galston @ Chicago Ventures

Ezra Galston is a VC @ Chicago Ventures, where he focuses on consumer facing and marketing tech investments and is actively involved with Blitsy, BloomNation, Kapow Events, Luxury Garage Sale, Shiftgig, SpotHero, and Zipments. Ezra’s thoughts on startups, have been published in the Wall Street Journal, TechCrunch, VentureBeat and Re/code.
Prior to Chicago Ventures, Ezra was a Young Entrepreneur at Foundation Capital. Before business school, Ezra served as the Director of Marketing for CardRunners Gaming – the parent company of CardRunners, Hold’em Manager and DraftDay – and before then earned a living as a professional poker player. If that wasn't enough he is also the author of one of our fave VC blogs www.breakingvc.com.

In Today's Episode You Will Learn:

  • How Ezra became a Poker Player and then transitioned to the world of Venture Capital?
  • What is the mission with Chicago Ventures? Average ticket size? Preferred sector?
  • How important is it for startups to be close to their investors, geographically and relationship wise?
  • For marketplace startups, what metrics does Ezra really deep dive on?
  • With the likes of Instacart raising huge rounds, why are we seeing this huge increase in food tech?
  • In hugely crowded markets, how does Ezra sort the wood from the trees?
  • What advice would Ezra recommend to individuals looking to enter the VC industry?

Items Mentioned In Today's Episode:

Ezra's Fave Book: The Little Prince

Ezra's Fave Blog or Newsletter: Stratechery by Ben Thompson, Carpool.vc

Ezra's Fave Productivity Tools: Rapportive, Bitmoji

Ezra's Most Recent Investment: Luxury Garage Sale, Attendant

Bill Gurley: 10 Factors To Consider When Evaluating Digital Marketplaces

HungryRoot: Charlie O'Donnell, Brooklyn Bridge Ventures

As always you can follow Harry, The Twenty Minute VC and Ezra on Twitter right here!

Jaksot(1399)

20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

Chris Degnan is the former Chief Revenue Officer at Snowflake, where he was instrumental in scaling the company from less than $1M in ARR to over $3B in annual revenue. He joined as the first sales hires and built Snowflake's go-to-market engine from scratch, growing the team from to more than 6,000 globally. Under his leadership, Snowflake became one of the fastest-growing enterprise software companies in history, achieving a record-breaking IPO in 2020. AGENDA: 04:34 How to Build a Sales Team from Scratch 07:49 How to Hire and Evaluate Sales Leaders 15:23 Four Big Lessons Scaling Snowflake to $3BN ARR 31:30 Comparing Snowflake and Databricks: What Databricks Did Better? 35:26 How to Manage Sales Team Morale in Competitive Markets 43:53 Why Customer Success is BS and What To Do With It 48:31 How Every Sales Leader Needs to Change in An AI World 49:37 Biggest Reflections on Sales Leadership 54:38 Quick Fire Questions and Final Thoughts 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

10 Loka 20251h 2min

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

AGENDA: 03:29 OpenAI and AMD's Major Partnership 07:35 Microsoft Have F***** Up the OpenAI Partnership 17:08 OpenAI's Developer Day Announcements 20:45 Why VC is the Most Forgiving Asset Class on Price and Valuation 29:10 What Does it Take to IPO in 2025: Why Snyk Will Not IPO 42:30 Four Strategies Companies Need to Take to Own Their Own Destiny 49:31 Vercel Raises $300M at $9BN: Suicide Round or Strategic 55:39 Does King Making Really Work in Venture Capital: Legora vs Harvey 01:08:11 Chamath Raises Latest SPAC: SPACs are Back 01:10:56 Polymarket Raises $2BN at a $9BN Valuation 01:14:53 Quick Fire Questions and Wrap-Up

9 Loka 20251h 24min

20VC: Cerebras CEO on Why Raise $1BN and Delay the IPO | NVIDIA Showing Signs They Are Worried About Growth | Concentration of Value in Mag7: Will the AI Train Come to a Halt | Can the US Supply the Energy for AI with Andrew Feldman

20VC: Cerebras CEO on Why Raise $1BN and Delay the IPO | NVIDIA Showing Signs They Are Worried About Growth | Concentration of Value in Mag7: Will the AI Train Come to a Halt | Can the US Supply the Energy for AI with Andrew Feldman

Andrew Feldman is Co-Founder & CEO of Cerebras, building the world's fastest AI inference and training. Cerebras recently closed a $1.1BN Series G round at an $8.1 billion valuation, backed by top names including Fidelity, Atreides, Tiger Global, Valor Equity and 1789 Capital. Under his leadership, they've leapfrogged GPU limits in inference, operate at trillions of tokens per month, and are filing to go public soon. AGENDA: 02:43 Why We Did Not IPO and Raised $1BN From Fidelity 05:03 Analysis of Chip and Compute Landscape Today 07:14 NVIDIA Showing Signs They Are Running Out of Ideas 13:57 The Real Questions to Ask on Chip Depreciation 24:54 Energy Requirements for AI: Is it Feasible? 29:25 Mag7 Value Concentration: Feature or a Bug 31:57 Talent is the Bottleneck and Trump Makes it Worse 32:55 The War for Talent: Secrets No One Sees 34:22 Evaluating the Data Centre Economy: Many Will Lose Money 38:01 Three Changes the US Could Make to Beat China in AI 42:30 Why 80% of our Revenues are in the UAE 47:26 Quick Fire Questions 58:59 Why Work Life Balance is Total BS

6 Loka 20251h 4min

20Growth: How to Use Influencers to Scale Growth Insanely Fast | How to Optimise User Onboaring for Growth | How the Best Growth Teams Create Organic Growth and Community | Why LTV/CAC Models are BS with Ketty Slonimsky

20Growth: How to Use Influencers to Scale Growth Insanely Fast | How to Optimise User Onboaring for Growth | How the Best Growth Teams Create Organic Growth and Community | Why LTV/CAC Models are BS with Ketty Slonimsky

Ketty Slonimsky is Chief Growth Officer at Palta, the platform behind apps like Flo (the #1 female health app with 77M+ MAU), Simple, and Zing AI, where she leads a centralized growth function across the portfolio. She was previously first VP Product & Growth at HeliosX (£900M+ ARR, bootstrapped D2C healthtech), has advised companies like SonderMind, Runna, Guardio, Cheddar, P&G Digital Ventures, and is a board advisor at HeliosX. AGENDA: 02:33 What is Growth and When to Hire For It 06:04 Three Profiles of Successful Growth Leaders 10:07 Challenges and Learnings from Failed Ventures 21:17 How to Optimise User Onboarding for Growth 26:14 Biggest Lessons on Retention 30:25 How to Artificially Create Organic Growth and Community Building 32:10 Why LTV Models are BS 37:35 How to Use Influencers to Grow Insanely Fast 47:07 The Metrics that Matter in Growth 49:48 Push Notifications and Engagement: What To Do vs What Not to Do? 51:57 Quick Fire Round

3 Loka 20251h

20VC: Are Burn Multiples BS in an AI World | Sam Altman Needs $1TRN of Energy | Klarna, Figma, Stubhub, all Down: Are Public Markets Turning? | FiveTran and DBT: Is the Wave of Consolidation About to Begin?

20VC: Are Burn Multiples BS in an AI World | Sam Altman Needs $1TRN of Energy | Klarna, Figma, Stubhub, all Down: Are Public Markets Turning? | FiveTran and DBT: Is the Wave of Consolidation About to Begin?

AGENDA: 03:58 Understanding Burn Multiples and Capital Efficiency in an AI World 11:54 What Metrics Founders Need to Focus on in a World of AI 19:31 The Role of Kingmakers in Venture Capital: Harvey, Abridge, Profound 33:42 Klarna, Figma, Stubhub, all Down: Are Public Markets Turning? 36:35 OpenAI Needs the Same Energy as Japan… WTF! 41:09 How Can We Fund the $1TRN Sam Altman Needs for Energy 52:39 FiveTran and DBT: Is the Wave of Consolidation About to Begin? 59:44 Does Private Equity Need to Change in a World of AI 01:06:23 Political Expression and Corporate Responsibility

2 Loka 20251h 16min

20VC: OpenAI and Anthropic Will Build Their Own Chips | NVIDIA Will Be Worth $10TRN | How to Solve the Energy Required for AI... Nuclear | Why China is Behind the US in the Race for AGI with Jonathan Ross, Groq Founder

20VC: OpenAI and Anthropic Will Build Their Own Chips | NVIDIA Will Be Worth $10TRN | How to Solve the Energy Required for AI... Nuclear | Why China is Behind the US in the Race for AGI with Jonathan Ross, Groq Founder

Jonathan Ross is the Founder & CEO of Groq, the AI chip company redefining inference at scale. Under his leadership, Groq has raised over $3B from top investors. The company has reached a valuation of nearly $7B, positioning itself as one of NVIDIA's most formidable challengers. Previously at Google, Jonathan led the team that built the first Tensor Processing Unit (TPU), making him one of the leading architects of modern AI hardware. AGENDA: 00:00 The Future of AI and Compute 05:07 Why the Hyperscalers Have to Keep Spending Recklessly on AI 12:49 Why OpenAI and Anthropic Will Have to Build Their Own Chips 19:47 OpenAI and Anthropic Will be $5BN Companies: The Bull Case 29:50 Why China is Behind the US in AI and Deepseek is More Expensive to Run 33:55 How Europe Could Compete in AI and Why the US is More Risk Averse Than Europe 42:51 Why AI Will Lead to Too Many Not Too Few Jobs 43:19 Deflationary Pressures and New Job Markets 45:51 The Future of Vibe Coding 47:14 Why AI Companies Should Strive to Have Low Margins 49:31 Why We Have to Have Nuclear Energy and How to Bring it Back 56:55 How Permits are Ruining the Potential of AI 01:03:58 Why OpenAI and Anthropic are so Undervalued 01:16:53 Quickfire: Biggest Fear, Nvidia: $10TRN, Zuck Buying AI: Work or Not

29 Syys 20251h 21min

20Product: Revolut Business $1BN Revenue: Five of the Biggest Product Lessons | How Revolut Structures Product and Design Teams | How Revolut Experiments and Invests in New Product Bets | How Revolut Ships Product So Fast with James Gibson

20Product: Revolut Business $1BN Revenue: Five of the Biggest Product Lessons | How Revolut Structures Product and Design Teams | How Revolut Experiments and Invests in New Product Bets | How Revolut Ships Product So Fast with James Gibson

James Gibson is Head of Revolut Business. Under his leadership, Revolut Business now processes over $33 billion in monthly transaction volume and generates more than $1BN in annualised revenue. AGENDA: 04:10 Is Consulting the Worst Background for Aspiring PMs 07:09 How Revolut Hires for it's Product Team 17:21 How Revolut Sets Goals: What Works, What Does Not 19:37 How Revolut Structures Their Product Teams 22:13 How Revolut Structures Product Review Sessions 27:23 New Bets Process at Revolut 29:11 How Revolut Balances Super Users and General Customers 36:55 How Revolut Drives Product Velocity and Efficiency 39:26 Future of Product with AI 44:56 Quick Fire Questions and Reflections

26 Syys 202554min

20VC: NVIDIA Invests $100BN Into OpenAI | Is Triple, Triple, Double, Double Dead | Navan Files to go Public & Notion Hits $500M ARR | The Impact of H1B Visas on Startups in the US

20VC: NVIDIA Invests $100BN Into OpenAI | Is Triple, Triple, Double, Double Dead | Navan Files to go Public & Notion Hits $500M ARR | The Impact of H1B Visas on Startups in the US

AGENDA: 00:00 Why I am 100% Equities and 0% Cash 04:35 Nvidia's Massive $100BN Investment in OpenAI 08:39 Is Anthropic Negatively Positioned by OpenAI Gaining NVIDIA Investment 27:30 Is Triple, Triple, Double, Double Dead 44:00 Navan Files to Go Public at $8BN 49:31 Lockup Periods and Liquidity 50:35 Impact of H-1B Visa Changes on Startups 01:02:42: Notion Hits $500M ARR Re-Accelerating 01:09:42 Why Founder Friendly is Total BS Today

25 Syys 20251h 19min

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