A founder who sold his startup for $200 million paid for all 160 employees to party with him in Vegas - 'On a scale of 1 to OMFG, it was probably a 10'

If you're in your twenties, and you sell your company for more than $200 million, what do you do to celebrate?

For the three cofounders of Bleacher Report, the answer was a trip to Las Vegas. But they didn't just buy their own way. They also paid for all of their 160 employees to join them in Vegas.

In an interview for Business Insider's podcast, "Success! How I Did It," Bleacher Report cofounder Bryan Goldberg revealed a lot of business tips and tricks. But he also discussed how the Las Vegas trip happened. His team had just sold Bleacher Report to Turner Media for about $200 million, and Turner hadn't fully "wrapped its arms" around Bleacher Report yet, so there was a short window of opportunity to plan an epic trip.

Goldberg wouldn't reveal many details, except to say that they all managed to come back alive. He says he won't be doing that again if his new startup, Bustle, gets acquired, because he is now "old, stodgy Bryan" and it "isn't the right thing to do."

But it sure sounded like fun!

Here's the exchange:

Alyson Shontell: You sold Bleacher Report and you and your cofounders went to Vegas. Tell me about the trip.

Bryan Goldberg: Under no circumstances will I talk about the Vegas trip.

Shontell: Oh, come on! You were young and dumb then. It doesn't matter.

Goldberg: I cannot believe we did that.

Shontell: Why? That's what everyone should do when they sell, right?

Goldberg: No, it's not what you should do!

Shontell: Who all went to Vegas?

Goldberg: The whole company.

Shontell: The entire company, all of Bleacher Report?

Goldberg: The entire company.

Shontell: Did you pay for them all?

Goldberg: We did. The founders paid for it. We had sold the company. We had made money, and we said, "Let's each chip in like X-thousand dollars and fly the company to Vegas."

Shontell: How many people was it at that point?

Goldberg: At that point it was like 160 people, 170 people. The CEO, Brian Grey, very wisely didn't go. I think one of the fun things about having a CEO when you're in your 20s running a company is he can be the grown-up and he can look the other way. He was like, "I'm not going anywhere near this. You pay for it out of pocket. You do it on the weekend. This is not a Bleacher Report event."

It was so early after the sale that I think Turner hadn't really put their arms around us, so we had this very narrow window for the founders to pay out of pocket to do a noncompany event on the weekend to go to Vegas.

As we know, what happens in Vegas stays in Vegas, but I would say that on a scale of 1 to 10 - like, OMFG - it's probably a 10. I don't know what an 11 would look like. I'm not going into it, except to say we all came back alive.

As we know, what happens in Vegas stays in Vegas, but I would say on a scale of 1 to 10 - like OMFG - it's probably a 10.

Shontell: What does a 10 look like?

Goldberg: You want to know what a 10 looks like? It looks like all the things you think about in a rock-star moment. It helped build the team. It was not forgotten, and that sort of behavior never again happened, and will never happen again.

Shontell: There's not going to be some Bustle Cancun trip when you sell?

Goldberg: If we sell Bustle, and I hate to say it - and my team at Bustle is going to hear this podcast and say, "Well, wait a minute. Bleacher Report got to do a Vegas trip - why don't we?" - and I'm going to say, "You know what, because I was young then and I'm old now, and old, boring, stodgy Bryan in his mid-30s is not going to do a trip to Vegas because it's just not the right thing to do."

I'm beet red right now - thank God this is a podcast. Because you just can't do those sorts of things. Not in the year 2017, 2018, 2019, whatever it turns out to be.

Shontell: Not with social media there to capture it all.

Goldberg: Exactly. I mean, Twitter existed but things were different back then.

To listen to the full podcast and learn how Goldberg built a $200 million business, plus get his thoughts on where the media industry is heading, check out the episode below: