Building an early-stage startup isn’t just about the technology — it’s about earning trust before the proof exists.

In this episode of Fund/Build/Scale, I’m joined by Jeff Smith, CEO and co-founder of 2nd Set AI, a startup building generative image and video tools for media, entertainment, and sports organizations.

Jeff is a repeat founder navigating a familiar but uncomfortable phase: selling complex, unproven AI into large enterprise organizations that are curious about generative technology — and deeply wary of it at the same time.

We talk about why his team pivoted away from an early market that wasn’t ready, how they earned investor trust without product-market fit, and what it actually takes to sell AI into organizations where legal, brand, and compliance concerns can stop a deal cold.

This conversation isn’t about overnight success. It’s about iteration discipline, founder-investor trust, and the realities of selling emerging technology to skeptical enterprise buyers.

RUNTIME 31:28

EPISODE BREAKDOWN

(2:10) What is 2nd Set AI?

(2:53) How/why the company pivoted from fashion to entertainment

(8:34) How 2nd Set AI landed its first paid engagement

(12:15) Effective product education helps overcome sales objections

(16:45) Founders beware: enterprise AI adoption gets bogged down by compliance issues

(19:25) “I’m not sure I believe in a lot of moats right now.”

(25:47) How Jeff measures progress toward PMF

LINKS

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Thanks for listening!

– Walter.

Selling Unproven AI to Skeptical Enterprise Buyers