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The Hustle Trap: Learning How to Work Less Can Lead to Success

Wonder Podcast: Empowering Women Entrepreneurs to Change the World

Release Date: 03/30/2026

The Hustle Trap: Learning How to Work Less Can Lead to Success show art The Hustle Trap: Learning How to Work Less Can Lead to Success

Wonder Podcast: Empowering Women Entrepreneurs to Change the World

Ryan Crownholm is an army veteran, serial entrepreneur, and founder of MySitePlan.com and DirtMatch.com. He is also the president and founder of Crown Capital Adventures Inc. When a runaway truck left him with a shattered femur and punctured lungs on a California hillside, he almost lost everything. Watching his business thrive without him from a hospital bed, Ryan discovered the leadership lesson that would change everything: Knowing firsthand how broken the construction industry was, he turned that experience into technology that now serves over 70,000 customers nationwide. Listen in as Ryan...

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More Episodes

Ryan Crownholm is an army veteran, serial entrepreneur, and founder of MySitePlan.com and DirtMatch.com. He is also the president and founder of Crown Capital Adventures Inc. When a runaway truck left him with a shattered femur and punctured lungs on a California hillside, he almost lost everything. Watching his business thrive without him from a hospital bed, Ryan discovered the leadership lesson that would change everything: Knowing firsthand how broken the construction industry was, he turned that experience into technology that now serves over 70,000 customers nationwide. Listen in as Ryan shares his incredible journey from living out of his car to building AI-powered companies and why he believes the entrepreneurs who thrive in the next decade will be the ones who learn to work smarter, not just harder. His book, “The Hustle Trap,” is a guide for how to do less work while making more.

Timestamps:

01:25 The Accident That Changed Everything

03:35 Beginnings in Construction 

05:53 Exiting

07:38 MySitePlan

08:19 The Hustle Trap

10:25 Capitalizing On AI

17:30 AI Disruption

22:07 The Human Touch

24:35 Leadership Shift

25:51 Volunteering for Purpose and Mentorship

27:43 Staying Calm

29:45 Freedom Through Travel and Adventure

32:35 Books Beliefs and Entrepreneur Advice

34:31 Work for Yourself Mindset

Links:

Ryan’s Website: https://www.ryancrownholm.com/

The Hustle Trap: https://a.co/d/07LOoCEo