Matt Watson grew up in a trailer park in Oklahoma and worked flea markets with his dad from the age of five. At 22, he founded VinSolutions, a CRM for car dealerships. Eight years later, he sold it to AutoTrader for $150 million. He was 29 and the largest shareholder.

Then he kept building. Stackify. At Capacity. And now Full Scale, a 350-person software company he chose to keep instead of sell.

In this episode, Matt and I go deep on what actually happens after you go from nothing to generational wealth in your 20s. We talk about how the day the $150 million wire hit felt like, what surprised him most about having that kind of money, why more money more problems is absolutely the case, and why he started Stackify two months after his exit even though he could have stopped.

We also get into the hard lessons he learned as a solo CEO in his 30s,  why he's simplifying his life at 45 after buying Ferraris and part of a private jet, and what he'd tell someone who thinks money is the answer to everything hard in their life. 

This is a conversation about what  happens after you make it. If you've ever wondered what's on the other side of the number you're chasing, this one's for you.

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(01:19) Trailer park to flea markets at 5 years old
(03:37) Did he ever dream big
(04:57) When it felt like a real business
(07:45) Selling for $150 million at 29
(07:59) Off the rollercoaster
(08:46) Why the exit made life worse
(11:32) What surprised him about money
(12:28) Why friends stop inviting you over
(13:03) Starting again two months later
(13:51) Solo CEO, hard lessons
(15:36) Being his own VC
(16:42) Diagnosing ADHD at 40
(20:02) His most important company
(23:27) Startups are brain damage
(28:21) Ferraris, a jet, letting go
(30:03) The key to happiness

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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