This VC Admitted He Was Wrong for Passing on the Seed - Jake Fingert, Camber Creek - EP#119

He rejected a founder’s seed round. When that founder went out to raise his Series A, Jake’s firm was the first call he made. Jake is the Managing Partner at Camber Creek, a venture firm that invests in proptech and fintech, has nearly $1 billion under management and has backed more than 50 companies, including Bilt Rewards. Before venture, he worked in consulting at Deloitte and BCG, then in government, first at GSA and then as a senior policy advisor on the National Economic Council in the Obama White House. He and David have known each other for over 25 years. In this episode of Not Another CEO, he explains how he decides whether to back a founder, what founders get wrong about his side of the table, and what the White House taught him about building companies. Here are the best takeaways from the episode: 1. Resilience beats everything: Jake backs founders who found a problem with no good solution and will do whatever it takes to solve it, not people drawn to the Silicon Valley or YC image. Very few companies become multibillion dollar successes overnight, so he wants the founder who can keep going through the hard stretches. 2. A no can be a request for proof: Jake passed on Bilt’s seed round but told the founder to stay in touch. Over the next 12 months the founder did what he said he would, including partnerships with banks, airlines and hotels, and Camber Creek was the first call for the next round. 3. Self-awareness is a filter: Jake would rather hear what you got wrong than hear that everything is perfect. A founder who can’t name what keeps them up at night is a quick pass, because it shows a lack of self-awareness and empathy for customers, employees and investors. 4. He decides fast, then verifies: About 30 minutes tells Jake whether he wants to partner with someone for ten years. Customers, other investors and even a college roommate then tell him whether that person will build a big company. 5. Bring your board questions you can’t answer yourself: The most common pitfall Jake sees is founders asking questions they already know the answer to. Send the financials in advance and spend the meeting on real strategic choices, with board members who bring different backgrounds. Quote of the Show “To me, one of the biggest turn offs is when I meet a founder and I say, you know, what keeps you up at night? And they say nothing.” - Jake Fingert, Managing Partner, Camber Creek Guest featured in this episode: Jake Fingert, Managing Partner, Camber Creek LinkedIn: https://www.linkedin.com/in/jake-broder-fingert-a4388b3/ Camber Creek: https://cambercreek.com/ We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode. Chapters: 00:00 Introduction 02:07 The one trait Jake looks for in founders 03:53 Passing on Bilt's seed round 08:23 The red flag: "nothing keeps me up at night" 10:21 How fast a VC decides 15:25 How to run a board meeting 22:53 From GSA to the White House 27:23 What founders don't understand about VCs 33:13 How Jake has changed in ten years 38:00 Is this 2021 again? 42:53 Moats and founder-led sales in the AI era 55:15 What to teach your kids: AI tools and finding truth