Retired From Corporate America at 44

Episode 002: Retired From Corporate America at 44

Andy Olen shares the personal story behind his decision to walk away from corporate America at age 44. He wasn't done working, but stopped outsourcing his time, energy, and financial future. What followed was the intentional leap into solopreneurship, building a business of one, reclaiming family time, and unlocking what Andy calls self-wealth.

Episode Highlights

- Why Andy’s corporate “retirement day” was quiet, uncelebrated, and eye-opening
- Lessons from Formula One legend Lewis Hamilton and the symbolism of the number 44
- The emotional tug-of-war between fear and commitment when leaving corporate life
- The “burn the boats” mindset and why going back was never an option
- How 17+ years in corporate leadership masked the real limits on wealth creation
- Why W-2 income and corporate 401(k) plans quietly stunt financial growth
- How LLCs and S-Corps unlock flexibility, tax efficiency, and self-directed investing
- The overlooked power of Solo 401(k)s and reinvesting in yourself
- Redefining wealth as more than money: time, freedom, and optionality
- Why Andy started North Hall Partners and why he chose a business of one

Key Takeaway

Corporations are designed to extract your best years and cap your upside.
Solo entrepreneurship creates leverage... financial, personal, and emotional.

Self-wealth isn’t about getting rich fast.
It’s about owning your time, controlling your capital, and creating options.

Memorable Moments

“There was no farewell tour. No sheet cake. Just a bad cafeteria salad.”
“I didn’t retire from work—I retired from the corporate grind.”
“At 44, I realized I couldn’t work this hard to make other people wealthy.”

Connect with Andy

Email: [email protected] 
Substack: Bet On Yourself — daily notes, long-form essays, and practical playbooks
Subscribe to the podcast for future episodes on: Solopreneurship, Self-wealth strategies, Financial independence for professionals, Building a business and life on your terms

Final Thought

Andy has lived on both sides:
17+ years in corporate leadership
6+ years as a successful solopreneur

This podcast is about sharing the cookbook, the recipes, and the lessons learned so you don’t have to figure it out the hard way.

It’s time to stop outsourcing your future.

It’s time to bet on yourself.