1 in 20 Trust AI With a Deal: How to Close the Trust Gap

Why do customers who praise your demo end up not buying? In this striking episode of Predictable B2B Success, Vinay Koshy interviews Dan Mosher, CEO and co-founder of DealGround, about the awkward gap between using a state-of-the-art product and trusting it when it really counts.

Since Dan Mosher knows the kind of thing it takes to gain a foothold in difficult markets, having been involved in growing companies such as Postmates, Brightroll, and Presto, and usually getting there a bit too early, he is now addressing the trust gap in commercial real estate, a field in which agents enjoy using AI tools but seldom actually use them to close deals.

In this episode, you'll learn why many excellent products stall at the "pilot" stage and what shifts a customer's mindset from curiosity to confidence. You'll learn how Dan Mosher turned a deeply skeptical person into a fan in just one demonstration, and why building trust has nothing to do with features and everything to do with reframing expectations, embracing failures, and quickly bringing forward the "aha!" moments.

If you're struggling with market timing, finding it hard to turn trials into trust, or considering your own move from a corporate job to startup life, you won't want to miss the practical advice and hard-earned lessons in this discussion.

Some topics we explore in this episode include:

• Why B2B buyers use but rarely trust AI and what flips the switch
• The double standard: Human error vs. AI mistakes in business decisions
• How AI hype sabotages adoption and how to set expectations that build trust
• Where commercial real estate agents actually waste the most time
• Turning product demos into “aha” moments that change hardened minds
• Walking the privacy line: When valuable data becomes “too personal”
• Leveraging strategic partnerships to punch above your startup's weight
• Accuracy promises: How to win deals without overpromising on AI
• Why startups fail when tech builds for industries they don't understand
• The first 90 days: How smart leaders validate ideas before leaving their day job