Connection Is the New Currency with Jason Yeh, Part 2

This week, Dan picks up right where he left off with Jason Yeh, founder of Scaling Freedom, for a rapid-fire dive into the real-world side of AI. Jason shares battle-tested frameworks for deciding when to use AI (and when a simple script is smarter), explains why human connection will matter even more as automation spreads, and gets personal about parenting, education, and staying nimble in a market that changes every week. If you’re wondering how to weave clarity, technology, and meaning together—without losing the human spark—this conversation is for you.

Show Highlights

• Treat AI like a smart “drunk intern”—speak out loud, let it interview you, and watch the prompts improve [00:00:31]

• Build a custom GPT that turns raw thoughts into perfectly engineered prompts [00:02:37]

• “AI on a bad system just scales the mess”—why process always comes before tooling [00:04:36]

• The hidden gold mine of manual data entry and how scraping invoices unlocks insights [00:06:51]

• Jason’s 4-point litmus test for any AI project: Painful · Existing process · High impact · Strong data [00:09:56]

• Planner vs. Solver: use one “conductor” agent plus narrow specialists for higher accuracy [00:17:13] 

• Klarna’s chatbot fiasco & the lesson: some moments demand a human, not a bot [00:18:28]

• “Connection is the new currency”—brands that stay human will win customer loyalty [00:23:09]

• Staying nimble: why Jason refuses to ossify into a single product in a hype-driven market [00:24:45]

• The next frontier: AI-personalized education and raising kids who still think critically [00:28:12]

• Using Perplexity for curiosity walks and co-creating bedtime stories with your kids [00:32:37]

For more updates and my weekly newsletter, hop over to https://betterquestions.co/

To learn more about Jason Yeh, check out the websites below: 

https://scalingfreedom.ai/

https://www.linkedin.com/in/jasonjyeh/