He Lost Everything. Then Rebuilt His Life. With Reid Zeising | Ep 90

Reid's career began in investment banking, where he worked on major financial transactions and developed a passion for complex deals. Eventually, that ambition led him to pursue a takeover of the restaurant chain Backyard Burgers.

After a two-year battle, he succeeded in taking the company private in November 2007.

But the victory didn't feel the way he'd imagined.

Reid describes looking around the room after closing the deal and realizing that everyone there had been paid to attend. What should have been a defining moment of success became one of the loneliest days of his life.

Then the financial crisis hit.

The business struggled, Reid lost everything, and he was left with approximately $22 million in contingent liabilities that took five years to resolve.

What followed was a personal transformation.

Reid talks openly about confronting his ego, finding mentors, rebuilding his values, and learning that success doesn't have to come at someone else's expense.

He eventually found a new opportunity helping people access funds and medical care while awaiting personal injury settlements. That opportunity grew into GAIN Servicing, a business built around financial solutions, technology, and relationships with healthcare providers and law firms.

The conversation also explores the realities of scaling a company, building leadership teams, managing remote employees, preparing for growth, and making difficult decisions during the COVID shutdown.

And through it all, Reid returns to one central lesson: success means more when you're helping other people succeed.

• From investment banking to entrepreneurship
• The takeover of Backyard Burgers
• Losing everything after the financial crisis
• The $22 million financial aftermath
• Ego, humility, and personal transformation
• How mentorship helped Reid rebuild
• The origins of GAIN Servicing
• Financing medical care and legal settlements
• Scaling a company through people and processes
• Why leadership must evolve as companies grow
• The challenges of remote work
• How Reid's team navigated COVID
• Finding purpose in helping others succeed

If you're building a business, leading a team, or navigating a difficult chapter in your own entrepreneurial journey, Reid's story offers a powerful perspective on what success really means.