Many professionals spend years climbing the ladder only to discover they’ve built a business—or career—that depends entirely on them. Long hours, constant stress, declining health, and zero flexibility quietly replace the freedom they were chasing.

Even successful exits don’t guarantee peace. Without intention, entrepreneurs fall right back into grind mode, recreating the same pressure under a new name. Add health scares, burnout, and mental overload, and “success” starts feeling like a trap instead of a win.

In this episode, Jeff Kikel sits down with James Lang, a former college dropout turned COO who helped scale and exit a $20M company, to unpack what real freedom looks like after success. James shares how health challenges forced him to redesign his life, why most people accidentally build prisons instead of businesses, and how he’s now helping companies navigate AI without fear, hype, or ballooning costs. This conversation is a powerful reminder that freedom isn’t just about money—it’s about health, clarity, and building systems that work with your life, not against it.

Key Takeaways:

• Why most people unknowingly build businesses that trap them instead of free them

• How James went from college dropout to COO and successful company exit

• Why “toxic entrepreneurship” is replacing real ownership in the gig economy

• The danger of being told how much you’re allowed to earn

• How health crises force better business design (whether you like it or not)

• Why mental health is a leadership advantage—not a weakness

• The hidden cost problem no one is talking about in AI

• Why James avoids investing in AI stocks despite working in the space

• How AI should multiply people, not replace them

• Why trust-based teams are essential to freedom

• The difference between building fast and building sustainably

About the Guest:

Today’s guest is James Lang, Managing Partner at OverLang Venture Partners and a leader with a remarkable track record in scaling organizations. Before launching his venture firm, James served as Chief Operating Officer of a MedTech startup where he generated over $20 million in revenue and built a team of 60 people from the ground up—developing talent, culture, and operational excellence along the way.

Now, James is focused on helping American companies leverage AI the smart way. Through OverLang Venture Partners, he and his team have developed a proprietary AI infrastructure designed to accelerate growth while respecting—and enhancing—the human capital inside each organization. James brings a blend of real-world executive experience, technical insight, and a passion for empowering businesses to compete in a rapidly evolving digital landscape.

Links:

https://www.overlang.com/

https://www.facebook.com/james.lang.542358

https://www.youtube.com/@OverLangVenturePartners

Fast Five Questions:

1. If you woke up and your business was gone, you have $500, a laptop, a place to live, and food, what would you do first? “The first thing I’m doing is calling the people in my network that I already have trust and mutual respect with and asking how I can help. Step one is helping someone else. Step two is understanding why they need that help—because that’s where opportunity lives.”

2. What is the biggest mistake that you have made in business? “Grinding without paying attention to my mental health. I thought I just had to work harder and push through, and I didn’t realize how much damage that...