All episodes

Episode · Sep 9, 2026 · 2 hr 11 min

From Compulsive Gambler to a $465 Million Exit

with Rich Galgano

Rich Galgano is a former compulsive gambler who entered Gamblers Anonymous at 23 and built Windy City Wire.

Listen on
“I'm looking for the Gamblers Anonymous room.”
Rich Galgano

Summary

Rich Galgano describes growing up in Bolingbrook in a five-child family where money was tight. A fight left him with a broken leg and led his father to pull him out of Illinois State. In community college and afterward, he gambled on poker, dice and blackjack while holding jobs. After a three-day run at casinos left him broke, he called 1-800-GAMBLER and went to Gamblers Anonymous at 23. He says he has not gambled in nearly 33 years.

Rich and Gary Keller started Windy City Wire in 1994 with a $100,000 bank line and a plan written on Subway napkins. A lawsuit over customer solicitation nearly bankrupted them, but a contact at Gamblers Anonymous led Rich to attorney Dan Purdum. After the case settled, the company expanded, took on investors, bought back shares, and sold to Diploma PLC for $465 million in 2020. Rich also discusses his heart problems, his later company Scylos, and Reload, a recovery tool he is building.

Show notes

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: @richgalgano

His book: Down to the Wire: The Outlandish Tale of How I Quit Gambling to Win Big.

Read the transcript

Transcript

Made from YouTube's automatic captions and lightly corrected, so a few words and names may be off. Click a time to play the video from there.

Ken Rideout

All right, guys. Today's special guest, former gambling degenerate turned entrepreneurial superstar, the great Rich Galgano. Welcome to the show, Rich.

Rich Galgano

Thanks, Ken. Appreciate the opportunity to be here and tell my story and share my wisdom, maybe.

Ken Rideout

Yeah, I'm dying.

Rich Galgano

Depends who uh who tells you it's wisdom or not.

Ken Rideout

I'm dying to hear it. And I hope you don't take the uh former gambling degenerate as an insult. I I am an exjunkie. So I think most of us that are in recovery can recognize how deep into our addictions we were.

Rich Galgano

I always call myself a degenerate compulsive gambler. But you can't say that today cuz the young kids, you know, you can't call them degenerates.

Rich Galgano

I am. I am a gun guy.

I'll have to get you some of the protective ones, too. I feel like a real uh superhero when I put on my shooting glasses here. But let's get into it, man. Where'd you grow up? I grew up in a town called Bolingbrook, Illinois, which is about 25 miles west, pretty much west of Chicago. Middle class, lower middle class uh area. Uh my father was a Korean War vet. Never really he had jobs, never really a career, always had jobs. And my mother, both of them grew up in Chicago.

Uh and my mother, by the time I was the last of five kids, and by the time I was in first grade, my mother had entered the working world. And you're talking, this is 1974, 1975. That was a rarity.

Key takeaways

  • A winning streak can keep compulsive gambling going even when losses outweigh the wins.
  • Rich called 1-800-GAMBLER and went to Gamblers Anonymous when a three-day betting run left him broke.
  • A referral from another Gamblers Anonymous member connected Rich with the lawyer who defended Windy City Wire.
  • Rich and Gary started Windy City Wire with a bank line and a business plan drawn on Subway napkins.
  • The $465 million sale did not settle the health and personal problems Rich discusses later.
  • Buying back shares helped Rich regain control before the later sale.

Nowhere to Hide

A weekly letter from Ken Rideout about doing the uncomfortable part, and the reasons we use to avoid it.

It starts with 3 Days, 3 Hard Things: one short story from Ken and one hard thing to do, every day for three days. Then one letter a week.