Adam Rossi, who sold his company Platinum Solutions and found life-changing wealth, shares his journey of coping with regret and redefining purpose post-exit. He discusses the challenges of transitioning from entrepreneurship to investing, emphasizing the importance of mindfulness. Adam's insights on balancing family life with business are particularly compelling, revealing how building the business with his wife, Leila, strengthened their marriage. He reflects on the allure of philanthropy and the struggle for meaningful impact versus financial gains.
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insights INSIGHT
Why Exited Founders Struggle Investing
Exited founders often make bad investors due to a lack of investing experience outside their core industry.
Optimism and a tendency not to say no make them vulnerable to scams and poor investments.
question_answer ANECDOTE
Failed Acquisition Due to Hubris
Adam quickly bought a HVAC manufacturing company after his software exit but missed a major problem in due diligence.
His hubris and speed led to a poor acquisition resulting in a significant loss.
volunteer_activism ADVICE
Buy to Skip Viability Stage
Acquiring a company with an existing product-market fit can skip the risky viability stage.
This trade-off of money for time reduces risk and accelerates growth for seasoned founders.
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Finding Success, Happiness, and Deep Purpose in the Second Half of Life
Arthur C Brooks
In 'From Strength to Strength', Arthur C. Brooks addresses the inevitable decline in abilities that comes with aging and provides a practical guide on how to transform this period into an opportunity for growth. Drawing on social science, philosophy, biography, theology, and eastern wisdom, as well as interviews with everyday men and women, Brooks advocates for refocusing on priorities such as deep wisdom, detachment from empty rewards, connection and service to others, and spiritual progress. He argues that by adapting our expectations and focusing on these areas, we can achieve increased happiness and purpose in our later years.
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
Exit Paradox 