Dan Teran is a Cofounder and Managing Partner of Gutter Capital. Gutter is an early-stage firm based out of New York focused on founders tackling the world’s toughest problems. We talked about why Gutter invests with conviction, why they seek out founders with unique insights rather than Gutter trying to dream up their own, and how AI can solve problems in the real world, not just online. We also dug into:

+ Gutter’s core focus on vertical AI, vertical SaaS, and marketplaces tackling messy, real-world problems

+ Why Dan gravitates toward underestimated, “lived-experience” founders over polished, pedigreed profiles

+ Inside Elbow Grease, Gutter’s AI accelerator: structure, check size, and how they plan to keep backing winners

+ How Gutter turns talent into a product: embedded head of talent and heavy support on early hiring

+ The firm’s discipline on valuations, small fund sizes, and staying aligned with founders in a top-heavy market

+ Why Gutter insists on taking a board seat at seed and how that sets companies up for stronger Series As

+ Dan’s lessons from selling Managed by Q to WeWork and why founders should build acquirer relationships early

+ Two contrarian views: second-time founders are overrated, and the best founders do want real help from their investors

Investing in Startups is produced by Seaplane Ventures and hosted by Joe Magyer.

E47: Gritty Founders, Weird Markets, and Vertical AI with Dan Teran