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!

Episoder(1433)

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20VC: Groq's $20BN NVIDIA Acquisition | Manus Acquired by Meta for $2BN | Why Sam Altman Does Not Care About Dilution | Navan Trading at 4x ARR & Why Going Public Does Not Make Sense Anymore | The Rise of Invisible Unemployment and Labour Markets in 2026

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20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

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20VC: Enterprises Will Not Adopt AI without Forward-Deployed Engineers | Who Wins the Data Labelling Race: How Does it Shake Out? | How Synthetic Data Threatens the Future of Human-Generated Data with Matt Fitzpatrick, CEO of Invisible Technologies

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20VC's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face

20VC's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face

AGENDA: 03:48 Founder of the Year 2025 06:58 Product of the Year 10:05 Fund of the Year 20:52 Breakout Companies of 2025: Who Made the Biggest Impact? 26:57 Biggest Surprises of 2025 32:57 Predictions...

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20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf

20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf

Gérald Marolf is the Chief Product Officer at On Running. Gérald oversees the full range of On's shoes, apparel and accessories to make sure each delivers performance, comfort and style. Before On, Gé...

19 Des 202556min

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

AGENDA: 03:32 Lightspeed's $9 Billion Fundraise 05:20 The Impact of Mega Funds on Seed VCs 10:09 The Supercycle of Growth and Late-Stage Investments 13:06 Disney Invests $1BN into OpenAI and What It M...

18 Des 20251h 22min

20VC: a16z's David George on How $BN Funds Can 5×, Do Margins & Revenue Matter in AI & the Most Controversial Bet at a16z

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David George is a General Partner at Andreessen Horowitz, where he leads the firm's Growth investing team. His team has backed many of the defining companies of this era, including Databricks, Figma, ...

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20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg

Raaz Herberg is the Chief Marketing Officer and VP Product Strategy at Wiz, the fastest-growing cloud security company in history. As one of the first 10 employees, Raaz has helped scale the business ...

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