From Compulsive Gambler to a $465 Million Exit | Rich Galgano
About this episode
Rich Galgano shares his journey from gambling addiction to building a successful business with a $465 million exit.
Rich Galgano came back from Vegas so broke that a friend had to pay to get his car out of the airport parking lot. He swore he was done gambling. Then he got home, found $500, and went straight back to another casino. I know what it’s like to promise yourself you’re finished and then do the same shit again. This week, I sat down with Rich to talk about the gambling addiction that was taking over his life, the three-day bender that finally made him ask for help, and walking into Gamblers Anonymous at 23. He told me he hasn’t gambled in nearly 33 years. But getting out of the casino was just the beginning. Rich and his business partner started Windy City Wire with a $100,000 bank line and a business plan they worked out at Subway. Almost immediately, they were fighting a lawsuit that threatened to shut them down. The story of how he found the right lawyer and fought back is fucking unbelievable. He went on to build a company that sold to Diploma PLC in a $465 million deal in 2020. We get into recovery, knowing your worth, choosing the right partners, buying back your own business, and why money doesn’t fix what’s going on in your head. Rich also shares the heart…
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