My guest today is Adam Rossi. He sold his company, Platinum Solutions, 14 years ago and walked away with life changing wealth. But what hit him first after his exit was regret. We talk about how he came to terms with his new reality, searched for his new purpose, and dealt with losing his found identity. My favorite part of Adam's story is that he built his company with his wife, Leila, and their marriage didn't just survive. Building and selling the business, it actually got stronger through it. We talk about what Adam would do differently now that he's had 14 years to reflect. Adam's story is fascinating and full of hard won wisdom. I'm so grateful he shared it.

00:00:00 – Introduction & Adam’s Exit Story
00:01:06 – Why Exited Founders Make Bad Investors
00:05:15 – From Angel Investing to Private Equity
00:09:00 – Why Most Second Companies Fail
00:10:15 – Lessons from a Failed Acquisition
00:12:07 – Buying vs. Building a Business
00:14:34 – Regret After Exit and Finding New Purpose
00:17:27 – Sacrifice, Purpose & The Next Big Thing
00:20:18 – Impact, Meaning & Philanthropy Struggles
00:23:44 – Coaching Entrepreneurs as a Calling
00:25:18 – Why He Hasn’t Jumped into a Big Mission Yet
00:27:00 – Kids, Family, and Timing the Next Move
00:29:00 – Angel Investing: Rise and Decline
00:31:06 – The Illusion of Control in Angel Investing
00:32:35 – Advice for New Angel Investors
00:34:45 – Lifestyle Balance Post-Exit
00:36:00 – The Grind Years: 20-Hour Days and Stress
00:38:00 – Building a Business with His Wife
00:41:30 – Division of Labor and Complementary Skills
00:43:00 – Conflict Resolution in a Husband-Wife Team
00:44:45 – Why They Didn't Start a Second Business Together
00:46:15 – Raising Entrepreneurial Kids with Wealth
00:50:45 – The Only Real Passive Investing Strategy
00:53:26 – Life Rules: Wealth vs. Freedom
00:56:40 – Is Balance Between Mission and Freedom Possible?
00:58:45 – Mental Health After the Exit
01:01:00 – Why He Shares His Story Publicly
01:03:15 – A Book for His Kids and Maybe the World
01:07:17 – Will He Publish It?
01:09:41 – How Adam Wants to Be Remembered
01:10:36 – Closing Thanks & Final Reflections

Going Back to School with The Master Investor