Most founders walk out of a pitch meeting with no idea what actually happened. The investor said they were interested. They asked for more information. They suggested you come back with traction. And you took all of that as a good sign — when in reality, you’d already been passed on.
In this episode of FOMO Sapiens, Patrick McGinnis welcomes Charlie O’Donnell, founder of Brooklyn Bridge Ventures and author of Founder Unfriendly: What Investors Won’t Tell You About Getting Funded, for a conversation that every founder should hear before they walk into their next pitch meeting. Charlie O’Donnell has spent over two decades in the New York startup ecosystem, beginning as the first analyst at Union Square Ventures, helping launch First Round Capital’s NYC office, and ultimately building Brooklyn Bridge Ventures, the first venture fund based in Brooklyn, where he backed over 100 companies, including Hungryroot and Petal.
The conversation covers:
Patrick and Charlie O’Donnell also get into FOMO as a fundraising mechanic, the systemic pressures on diverse fund managers, and why go-to-market, not traction or narrative, is the single hardest thing most founders fail to get right.
Charlie O’Donnell is a highly sought-after coach to top venture capitalists and a faculty member teaching entrepreneurship at NYU’s Courant Institute. He is the founder of nextNYC, the most active tech community and events platform in New York City.
For over two decades, Charlie O’Donnell has been a mainstay in the NYC startup and innovation ecosystem. He began his career as the first analyst at Union Square Ventures after working in General Motors’ venture capital and private equity group. In 2009, he helped First Round Capital open its New York office, sourcing early investments in companies such as GroupMe, Singleplatform, Moat, and Backupify.
In 2012, he launched Brooklyn Bridge Ventures—the first venture fund based in Brooklyn—backing more than 100 local startups, including Hungryroot, Petal, Brigit, Shortcut, Radformation, and Imagen. Known as the most accessible early-stage investor in New York, Charlie prioritized inclusivity: 40% of BBV’s portfolio companies were female-founded, 30% had a BIPOC founder, and 9% had a Black founder.
Charlie O’Donnell has been named to Business Insider’s 100 Most Influential People in NY Tech five times and featured on City & State’s Tech Power 50. He is recognized for his early eye for transformational companies. Nick Bilton cited him as an influence on Twitter’s earliest investors in Hatching Twitter, and Dennis Crowley credits him with helping kick off Foursquare’s first funding round. At First Round Capital, Charlie sourced investments in Singleplatform (acquired by Constant Contact), GroupMe (acquired by Skype), Backupify, and Refinery29.
Outside of tech, Charlie O’Donnell is passionate about expanding public access to New York’s waterways. In 2010, after seven years as a volunteer at Downtown Boathouse, he co-founded the Brooklyn Bridge Park Boathouse, which welcomed 9,000 paddlers to the East River in 2022 with the help of 150+ volunteers. He has returned to serve as President of the organization.
Charlie is also an endurance athlete, a longtime member of the Brooklyn Triathlon Club, and a 20-year veteran (and captain) of his local co-ed softball team. In winter, you’ll find him playing goalie at Prospect Park’s ice rink. He lives in Park Slope with his wife and daughter, where he is President of their co-op board.
Since 2004, Charlie has shared his writing at www.thisisgoingtobebig.com.
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