Season 1 · Episode 75 · October 21, 2026 · 1h 4m

Building Products with AI Without Losing Human Judgement | w/ Ben Bilbrough

Show Notes

AI makes it easier to build a product, change your mind and start again. But when you can turn an idea into something usable over a weekend, it’s easy to fall in love with what you’ve made before you’ve worked out whether anyone needs it.

In this week’s episode, Jess and Kyle speak with serial founder Ben Bilbrough about building products with AI. His latest project, U26.vote, helps Americans understand the potential influence of their vote, but his experience offers practical lessons for anyone using AI to turn an idea into a business.

Ben shares how his team used AI to process complex data, develop ideas and iterate quickly—and where human expertise remained non-negotiable. They discuss what happens when Claude sounds right but isn’t, why easier development doesn’t always lead to better products, and how to keep a team focused when changing direction takes so little effort.

From the freedom to scrap your own work to the risks of falling in love with it, we explore what AI changes about product development, what it doesn’t, and why knowing what not to build matters more than ever.

Ben Bilbrough: https://www.linkedin.com/in/ben-bilbrough/

U26.vote: https://u26.vote/

ActionTank.io: https://actiontank.io/

Boardy: https://www.boardy.ai/

What You’ll Learn

How small teams can use AI to build products and iterate faster
Why the freedom to scrap your work can be both an advantage and a risk
Where human expertise remains non-negotiable when building with AI
Why vibe coding makes it easier to skip the questions that matter
How to keep your team and your AI focused when changing direction is easy
Why falling in love with the problem matters more than falling in love with your product

00:44 Weekly Catch-Up

05:02 This Week: What It Takes to Build Something Useful with AI

09:23 Introduction to Ben Bilbrough

12:42 Ben's Background in SMB and the Wedding Industry

14:17 The Knot, AOL and Ben’s First Exit

16:16 Why Ad Tech Treats Us as Consumers

18:26 How Nonprofits Can Ask Supporters for More Than Money

21:28 Understanding Voter Engagement and Political Influence

23:25 U26.vote: Scoring the Power of Your Vote

26:40 Building U26.vote With AI

31:50 AI as a Force Multiplier

37:05 Who Do You Need in the Room When Building With AI?