From Compulsive Gambler to a $465 Million Exit | Rich Galgano

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 problems that forced him to take his health seriously and what he’s building now with Scylos and Reload. This guy can tell a story. Hope you guys enjoy this one.  Follow Rich: @richgalganoHis book: Down to the Wire: The Outlandish Tale of How I Quit Gambling to Win Big. Thanks to ROKA for supporting the show. Please take a minute to subscribe and leave a comment. It makes a huge difference. More about the show at theothersideofhard.com. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Rich Galgano (00:40) Sponsor Shoutout Roka (01:08) Growing Up in Bolingbrook (02:01) Old School Childhood Lessons (04:23) Sports Setback Sparks Drive (06:51) Early Gambling and Work Ethic (08:27) College Poker and Party Fight (13:08) Riverboat Casinos Take Over (15:01) Blackjack Wins and Two Lives (16:45) Wire and Cable Sales Origins (21:57) Cold Calling and Big Margins (25:05) Chapter 11 Chaos and Mentors (29:53) Benders and Rock Bottom Signs (30:59) Broke at O'Hare (31:30) Back to the Casino (32:51) Three-Day Betting Spiral (34:30) Calling 1-800-GAMBLER (35:47) First GA Meeting Reality (39:14) 33 Years Clean (40:50) Clarity and Career Ambition (45:47) Starting the Wire Business (48:53) TRO Lawsuit Shock (52:39) GA Connection Finds Real Lawyer (59:16) Dan Purdum Courtroom Turnaround (01:02:22) Depositions and Fighting Back (01:03:14) Leaking Price Fixing (01:04:31) Winkle Breaks Under Deposition (01:06:40) Settlement Without Paying (01:08:44) Business Explodes After Lawsuit (01:09:25) Why Take Investors (01:10:16) Marriage and Staying Grounded (01:12:49) Money Doesn’t Fix You (01:13:42) Raising Money in LA (01:19:46) Taking Chips Off Table (01:20:40) Dodging a Bad LBO (01:23:15) The $6.5M Wire Moment (01:25:08) Private Equity Exit Pressure (01:28:48) The Great Buyback (01:33:04) Selling for $465M (01:35:34) Why Sell to Strategic (01:36:53) Family Office Focus (01:37:09) Cylos Endpoint Vision (01:38:06) Embezzlement and Rebuild (01:38:44) Stateless OS Explained (01:40:48) Go To Market Fundraising (01:41:30) Son Runs Investments (01:42:47) Venture Lessons and Diligence (01:47:53) Health Scare Wake Up (01:53:24) Longevity and Biohacking (01:58:05) Reload Recovery Tool (02:06:00) HYROX and Family Drive (02:09:17) Book Plug and Wrap Learn more about your ad choices. Visit megaphone.fm/adchoices