Gritty Founders, Weird Markets, and Vertical AI with Dan Teran of Gutter Capital

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.

The episode is now available on Apple Podcasts, Spotify, Amazon, and YouTube Music.

Chapters from Gritty Founders, Weird Markets, and Vertical AI with Dan Teran of Gutter Capital

• 00:04 – Gutter Capital, “real-world” problems, and why this convo matters

• 00:57 – What a “classic Gutter company” looks like (vertical AI/SaaS/marketplaces + overlooked insights)

• 02:49 – How they find non-traditional founders: cold inbound, feedback loops, and getting “proved wrong”

• 04:39 – Elbow Grease: why they launched an AI accelerator + what it’s optimizing for

• 06:29 – Why Gutter avoids dev tools—and where AI gets defensible in the real economy

• 08:42 – Portfolio examples: HVAC back-office AI agents + post-disaster reconstruction (CV + voice AI)

• 10:42 – Discipline vs flexibility: valuation rigidity, broad domains, and learning into “weird” industries

• 12:37 – Founder empathy: what “showing up” looks like when you’ve been in the trenches

• 14:43 – Managed by Q → WeWork: what Dan learned from selling, and protecting the team in the deal

• 16:20 – Why founders should build acquirer relationships early (creating optionality over time)

• 18:11 – The top-heavy venture market + why Gutter keeps funds small to stay aligned with founders

• 19:53 – Talent as a product: embedded head of talent, hiring leverage, and raising the bar portfolio-wide

• 21:47 – Why Gutter insists on seed board seats + “board hygiene” as a Series A advantage

• 23:42 – Concentrated portfolio construction: why ~15 companies per fund (and the data behind it)

• 25:37 – “Bullshit” conventional wisdom: second-time founders are overrated + “best founders don’t need help”

Chapters from Gritty Founders, Weird Markets, and Vertical AI with Dan Teran of Gutter Capital

• A “classic Gutter company” starts with a founder who’s seen the problem up close — Dan keeps coming back to the idea that the best early-stage insights aren’t invented in a pitch deck; they’re earned by being in the mess. That’s why Gutter leans into vertical AI / vertical SaaS / marketplaces in unsexy corners of the real economy where insiders can spot what outsiders miss.

• Cold inbound is a feature, not a bug — Instead of pretending the top of the funnel is only warm intros, Dan talks about building a system where cold founders can get real feedback, stay in the orbit, and come back sharper. The meta-point: early investing is often about giving yourself enough “shots on goal” to be surprised.

• Elbow Grease is an “AI accelerator,” but the real product is density + repeatable early access — The program is residential in NYC, built around getting teams physically close, moving fast, and tightening the loop between building and fundraising. The structure is explicit ($300k for 9%), but the underlying strategy is: see great companies earlier, help form them, and be positioned to keep leading as they grow.

• Real-world AI becomes defensible when it’s married to workflow + distribution — Dan draws a line between “very online” AI (where differentiation erodes fast) and AI that’s embedded in messy operations—where data, integrations, and behavior change compound. The examples he uses (like HVAC back-office agents and disaster recovery workflows) highlight that “boring” markets can create moats.

• Be rigid on price so you can be flexible everywhere else — He frames valuation discipline as the thing that lets Gutter wander widely across industries without losing the plot. If you keep your entry price sane, you can take shots in weird markets—gravel, construction, electrification—where the upside can be enormous but narratives are thin.

• Make hiring a first-class investing function — One of the most practical parts of the convo is how seriously Gutter takes talent: an embedded head of talent from day one, deep involvement in early team-building, and a track record of recruiting a large number of hires across the portfolio. The punchline: if you want outlier outcomes, you can’t treat hiring as “founder-only.”

• Small funds + meaningful ownership = alignment you can actually feel — Dan’s argument isn’t just philosophical—it’s structural. In a top-heavy venture market, he wants to stay in the zone where they can get meaningful ownership early and keep showing up with follow-on conviction, rather than being forced into “write big checks or don’t matter” dynamics.

• Two contrarian takes: second-time founders are overrated, and the best founders do want help — He pushes back on the current “second-time founder mania” and calls out the mythology that elite founders don’t need investors. His version is sharper: great founders are hungry for leverage—the real question is whether an investor is actually qualified to provide it.

The content here is for informational purposes only and should not be construed as investment, legal or tax advice. The opinions expressed by guests are their own and do not reflect the views of Seaplane Ventures. Our host, guests and clients may hold investments discussed in this podcast. Please invest responsibly.