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...

High-achieving professionals often feel trapped by careers they worked decades to earn. Long hours, constant stress, and systems that reward volume over impact leave them exhausted—yet afraid to step away because of income, identity, or fear of the unknown. At the same time, affordable housing is disappearing. Starter homes are no longer being built, rents continue to rise, and entire communities are priced out of

Doctors, executives, and other “dangerously overeducated” professionals tell themselves they can’t pivot. They postpone freedom until retirement, trading health, family time, and joy for security. The result? Burnout, regret, and years lost in careers that no longer fit who they’ve become.

In this episode, Jeff Kikel sits down with Dr. Maureen Gibbons, former emergency room physician turned lifestyle medicine expert and coach, to share how she intentionally transitioned out of traditional medicine without burning the boats. Dr. Maureen reveals how she rebuilt her career around health freedom, time freedom, and income freedom, created scalable systems instead of another stressful job, and now helps physicians and high-achievers escape burnout while making a bigger impact. If you’ve ever wondered whether it’s possible to redesign your life before retirement, this conversation delivers clarity, courage, and a practical path forward.

Key Takeaways:

• Why burnout isn’t a personal failure—it’s often a broken system

• How Dr. Mo transitioned from ER medicine to lifestyle medicine without financial panic

• The identity crisis professionals face when stepping away from prestigious titles

• Why creating systems can accidentally recreate another stressful job

• The dangers of hiring friends and “hiring for potential” too early

• How group coaching accelerates growth through shared learning and trust

• Why freedom requires aligning health, time, and income—not just money

• The concept of choosing relevance over retirement

• Why passive income and scalable skills are not a zero-sum game

• How small freedoms (like buying movie popcorn without stress) define real wealth

About the Guest:

Dr. Maureen “Moe” Gibbons—known as Dr. Moe—is a physician, entrepreneur, and author of Freedom to SHIFT. She helps high achievers trade overload for health, time, and income freedom through practical lifestyle medicine and real-world systems.

Links:

https://shiftwithdrmoe.com/

https://www.facebook.com/DrMoeGibbons

https://www.instagram.com/drmoegibbons

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? “I’d start with the same morning routine I do every day—take care of my body and my brain first. Then I’d ask, ‘Where do I put this $500 so it can multiply?”

2. What is the biggest mistake that you have made in business? “Hiring friends and hiring for potential—hopes and dreams. That’s what ruins friendships and creates pain.”

3. What is a book that you would recommend? “Buy Back Your Time by Dan Martell. That book was a complete game-changer for me.”

4. What is a tool that you use every day that you would recommend? “My calendar. If you can’t see how you’re spending your time, you don’t know what your priorities really are.”

5. What is your definition of freedom? “Being able to do what I want, when I want, without fear. And if my husband has a week off and says, ‘Can we go...

For many investors, real estate feels out of reach. Prices are high, competition is fierce, and institutional players dominate the market—leaving everyday investors unsure where to find stable cash flow and long-term opportunity.

At the same time, affordable housing is disappearing. Starter homes are no longer being built, rents continue to rise, and entire communities are priced out of traditional real estate ownership. Investors chase trendy assets while overlooking one of the most resilient and misunderstood sectors in real estate.

In this episode, Jeff Kikel sits down with Leo Young, former Tesla employee and co-founder of Cornell Communities, to unpack why mobile home parks and manufactured housing are becoming one of the most compelling real estate investments today. Leo shares how burnout and uncertainty at Tesla pushed him to seek passive income, how his first distribution check changed everything, and why professionally run mobile home communities can deliver strong cash flow while doing real social good. This conversation breaks down the stigma, the numbers, and the future of affordable housing investing.

Key Takeaways:

• How Leo went from studying finance and working at Tesla to real estate investing

• Why a single passive income check completely changed his mindset about wealth

• The truth about mobile home parks—and why the stigma is fading

• Why manufactured housing is the cheapest form of non-government subsidized housing

• How owning the land (not the homes) creates stability and lower default risk

• Why municipalities rarely approve new parks—and how that limits supply

• How professional operators improve communities through deferred maintenance upgrades

• Typical cap rates and why institutional money is flooding into the space

• The difference between active and passive investing in mobile home parks

• Why relationship-based deal sourcing beats competing with Wall Street funds

• How bundling small parks can create institutional-grade exit opportunities

About the Guest:

Leo Young is the Founder of Cornell Communities, a real estate firm revitalizing manufactured housing communities across eight states. He leads more than 500 affordable housing units and over $30M in assets while delivering strong, consistent returns for his investors. Before launching Cornell Communities, Leo worked in private equity and was the top regional salesperson at Tesla. Today he helps audiences understand the real story behind affordable housing, entrepreneurship under pressure, and building systems that scale.

Links:

https://leoyoungrealestate.com/

https://www.facebook.com/leoyoungre/

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

https://www.instagram.com/leoyoungrealestate

https://www.linkedin.com/in/leo-young/

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? “I’d reach out to my contacts and see how I can help them. The first step is re-establishing a financial base, because when you’re in survival mode you don’t make good decisions. I’d find a way to transact and build from there.”

2. What is the biggest mistake that you have made in business? “Thinking I could do everything myself. Even if you can, you shouldn’t....