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.

• 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/

This week, Dan sits down with Jason Yeh, founder of Scaling Freedom, to talk about identity, resilience, and rediscovering purpose through AI. Jason opens up about going against expectations, getting laid off (again), and why community has become the most vital part of his entrepreneurial path.

This is a personal and practical conversation on how Jason helps business owners bring AI into their work in ways that are human, useful, and deeply thoughtful — including a clear “Three A’s” framework you won’t want to miss.

Don’t miss this if you’ve ever wondered how to connect clarity, technology, and meaning — especially in times of uncertainty.

Show Highlights:

• Why Jason asks “What do you like to do?” instead of “What do you do?” [02:25]

• Growing up under pressure — and choosing his own way anyway [06:00]

• The defining moment: delaying graduation for a surprise study abroad [13:07]

• How getting laid off (again) led Jason to AI and entrepreneurship [17:24]

• The power of hiking, reflection, and reconnecting with community [20:13]

• Jason’s clear and useful “3 A’s” framework for AI: Automation, Answers, Advice [30:00]

• His #1 tip to beat prompt paralysis — “Have AI interview you” [34:14]

• Why connection is core to Jason’s business philosophy [27:22]

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/

Continuing from last week, today we discuss the fascinating ideas from Eric Nehrlich’s book, challenging how we perceive problems and revealing the empowering potential of our choices.

This episode takes you through Eric's unique journey from the corporate world to a coaching career, where he blends varied methodologies for life-changing results. Learn how to confront personal fears and make decisions that truly matter.

Don't miss out on the chance to gain insights that can redefine your approach to both personal and professional challenges.

Show Highlights:

• This is the only thing you can control [03:16]

• What is the meaning of accepting your reality? [09:49]

• Would you want your child to stay at a job he hates? [12:36]

• Discover a holistic approach towards coaching [14:31]

• Learn about Eric’s journey of coaching executives [19:52]

• Discover the real job of a coach [20:04]

• What are the unconscious fears that hold leaders back? [21:56]

• This is how you can get over your fears [25:32]

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

To learn more about Eric Nehrlich, check out the websites below:

https://www.toomanytrees.com

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

https://www.toomanytrees.com/book