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/