Learning From Failure: 3 $100M+ Operators & Their Darkest Moments

Sean Frank (0:00)

Welcome to the Operators Podcast. This week, we are going to celebrate a big event in Curtis' life, and you are going to hear each of us share one of the hardest moments we went through in our business careers and what we learned from it, how it changed us and transformed our future. We're so glad that you're with us today. Guys, how are we doing?

Curtis Matsko (0:20)

Well, my birthday's coming up in tomorrow.

Sean Frank (0:24)

Your way, no way, no freaking way. Your birthday is tomorrow?

Curtis Matsko (0:30)

Yeah, I'm taking 24 people.

Sean Frank (0:32)

Curtis, we share a birthday.

Matt Bertulli (0:34)

We share a birthday.

Sean Frank (0:36)

This is, it's like seeing a double rainbow. I don't know, like I am ecstatic. To share a birthday with you.

Curtis Matsko (0:45)

Do you know how many times people have said, you're like Mike from Simple Modern? Not fricking once in my life has that ever been.

Sean Frank (0:52)

I would question the sobriety or sanity of anybody that would say that. But I'll take the comparison for sure.

Curtis Matsko (1:00)

Oh, right, yeah. No, we got an equity partner with our company.

It took us a long time to do all the account. I think I talked to over 120 accountants, finance people, consultants, bankers, dip idiots, losers, people who asked me stupid questions.

Mike Beckham (1:20)

Why are you talking about your new equity partners in that way?

Curtis Matsko (1:23)

But we did an equity partnership.

I'm still the CEO.

I'm still, there's a board and I'm the head of the board. But I sold a huge chunk of the company to the equity partnership to be more steady, to get that next run to half a billion and a billion. And it seemed like a big thing. I'm gonna, if you've never, if you've done it, you know that the final moment is all done online. And it's just bankers saying, do you approve? Do you approve? Do you approve? The money's transferred? It's so weird.

Mike Beckham (1:55)

Dude, that call is so weird.

Curtis Matsko (1:58)

It's like 40 people you've never met. You agree to it and it's done in 35 seconds.

Sean Frank (2:04)

And all of a sudden many zeros appear.

Curtis Matsko (2:06)

That's what they say. I just, not a single thing changed. Everyone says, did you buy anything? And I'm like, no, no, nothing.

I came back, you know, I said what I wanted to do most. I wanted to do an podcast with Mike and Matt.

Sean Frank (2:22)

That's what I'm doing. Well, Curtis, then you're in luck because that is the topic today.

Mike Beckham (2:30)

You guys are too good.

Sean Frank (2:31)

Curtis, what is one thing you want to give some money to? You have the money to give now. What is one thing you want to give towards?

Curtis Matsko (2:37)

Mike, that's a great question. In the final couple months before this was done, I was still, I said, what is the chances this goes through? And they're like, it's 50-50 because we think you might change your mind. And I almost did. We're growing so fast, I almost said, go kiss my ass. Like, and more lawyers and more finance people. I just was like ready to tell them. And the only way I could stay positive was thinking, who can I help by doing this? And I'll tell you one that I just did. I am 14 and a half years sober. And the person who saved my life was a guy who was four and his brother was three when he was found in a hotel room where his mother abandoned him. Spent life in jail, fighting, drug addiction, the most kind, amazing, brilliant man I've ever met. And I called him up a couple of days ago and said, hey, how are you doing? And he's like, he called me governor. He's like, governor, I spent a year with this man who saved my life, like literally. And I said, I would like to send you this chunk of money. And he's like, his wife was there and says, is this real?

Like, is this possibly true? And he said, this is the governor, this is Curtis. Like, this is, if he says it, it's real. That's hard for a guy who spent his first year of sobriety with me. And I said, David, could you use this money? And he said, there are people on my roof right now because I have holes in my roof and no one, and I can't pay for it.

He said, this is a gift I could not even dream of.