Episode 425 of The VentureFizz Podcast features Charlie O’Donnell, Founder of Brooklyn Bridge Ventures and now, a published author.

Charlie is a staple of the NYC startup scene and someone who has had a significant influence in helping to build the ecosystem to what it is today. I first met Charlie back in 2010 at First Round Capital’s offices in NYC. At the time, I was helping out some of the city’s early high-flyers, like Birchbox. As you’ll see if you’re watching the video – or hear in this interview, I actually still have his business card from that meeting.

2010 was still the early innings for New York tech, and our conversation is a fun trip down memory lane. Charlie had his hands in some of the most important building-block companies of that era, including Foursquare, GroupMe, and Etsy. We also dive into the story of his investment in Backupify, a Boston startup founded by Rob May that was eventually acquired by Datto.

After his time at First Round, Charlie went on to launch Brooklyn Bridge Ventures, becoming the first VC to plant a flag in Brooklyn. He is now out with a new book titled Founder Unfriendly: A No-Nonsense Guide to How Investment Decisions Actually Get Made. It’s an honest look at what actually happens after you leave a pitch meeting.

Chapters:

00:00 Intro: Charlie O’Donnell

01:44 Meeting Charlie Back in 2010

03:27 Advice for Networking and Navigating the Job Market in 2026

06:35 Getting His Career Started in Corporate Pension Fund Industry

12:49 Early Days of the NYC Startup Scene

15:43 Early at Union Square Ventures

20:32 Early USV Deals: Twitter, Delicious, Etsy, Indeed

27:50 Challenges of Building in Recruiting & EdTech Industries

31:32 How Foursquare Led to NYC’s Startup Rebirth & His Role at First Round Capital

43:42 Sourcing GroupMe

49:00 The story of Backupify

52:16 Launching Brooklyn Bridge Ventures

54:35 Becoming a VC Coach

55:27 Founder Unfriendly – Book Details

58:55 Is Your Company a Fit for Venture Capital?

01:05:22 How Your Investors Might Affect Your Exit

01:12:59 More Details About Founder Unfriendly