About this episode

This episode discusses the challenges of selling unproven AI technology to skeptical enterprise buyers with insights from Jeff Smith, CEO of 2nd Set AI.

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…

People in this episode

Host: Walter Thompson

Guest: Jeff Smith

Topics covered

• selling AI
• enterprise technology
• trust building
• startup challenges
• product-market fit
• compliance issues

Keywords

• AI sales
• enterprise buyers
• startup
• trust
• product education
• compliance
• generative technology

Mentioned in this episode

Organizations: 2nd Set AI, media, entertainment, sports, fashion, investor

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