The Man Who Sold Off Vacasa: Sell Your Airbnb Business NOW — Before The Window Closes! | Jacobie Olin artwork

The Man Who Sold Off Vacasa: Sell Your Airbnb Business NOW — Before The Window Closes! | Jacobie Olin

Short Term Rental Secrets Podcast

August 10, 2026

What is your short term rental management company actually worth?
Speakers: Michael Sjogren, Jacobie Olin, Mike Reilly

Topics: Investing, Business, Entrepreneurship

**Michael Sjogren** (0:00)
If you've been interested in selling your short term rental business, then we've got a treat for you today. Today, we've got Jacobie Olin, the founder and managing partner of C2G Advisors. If you don't know who C2G is, they are the largest and probably most prominent M&A advisory firm, specifically dedicated to short term rentals. So you may have heard about the Vacasa and Casago deal that went through last year. Jacobie and his team brokered that deal. They also sold off all the Casago franchises after. They have been involved in every major transaction in the short term rental industry. Today Jacobie is going to talk about what does that process look like, how is your company going to be valued, and how can you maximize that value of your property when you decide the right time is to sell.
So sit back, enjoy this one. You're probably going to want to take some notes. Let's welcome Jacobie Olin.

**Jacobie Olin** (0:48)
Thanks Mike. Glad to be here.

**Michael Sjogren** (0:51)
Yeah, man. I've enjoyed a lot of conversations with you over the last year and a half. I always enjoy our combos. I always learn a ton and for the folks that aren't familiar with you and C2G Advisors, you want to just give us the 60 second scanning on what C2G does, the services you provide and how long you guys have been in the game.

**Jacobie Olin** (1:09)
Yeah, sure. So at C2G Advisors, I'm the founder and managing partner.
We're an industry focused M&A advisory firm. So the industry we're currently solely in is the short term vacation rental industry. Depending on who you talk to, it can be called short term rental. Some people call it vacation rental, Airbnb, whatever it is, it is all more or less the same thing.
We specifically work with companies that are looking to scale or companies that are looking to sell. So primarily, we work with companies really all across the US, a little bit in Canada, a little bit in Latin America. When they're looking to sell, we'll take them through a whole process, evaluation process, and then we'll take it to the entire sales process. And our goal is really to work with them, help get them the highest possible price for their business, but also help them find the best potential partner for the future of their business, their employees and their homeowners. Been in the business now for, I mean, I was born and raised in this crazy pirate industry, but went by separate ways for a while and came back in 2017 So it's been almost a decade now. Our team, we do around 20 transactions a year for about $200 million in total enterprise value. Since we are just in one industry, we go up and down market in terms of transactions. So last year, for example, we did a $100 million deal, which was extremely fun and crazy. And then we also at the same time did $150,000 deal. And really, so we do everything in between. I would say our average transaction falls around that like $5 to $10 million of EV. But it's fun. We've learned how to speak Main Street and how to speak Wall Street, depending on who our client is and who the buyers are.

**Michael Sjogren** (3:00)
I'm getting Cody Sanchez vibes. You're like the dude version of Cody Sanchez in our industry.

**Jacobie Olin** (3:06)
Love it.

**Michael Sjogren** (3:08)
So yeah, I mean, probably most notably last year was the Vacasa Casago deal, which you guys brokered. I know that was a long process to get that through. What does that actual process looks like when two giant companies are doing a merger like that?

**Jacobie Olin** (3:24)
How much time do we have, Mike?

**Michael Sjogren** (3:26)
I'll go all day, buddy. You tell me.

**Jacobie Olin** (3:28)
So that was one of the wildest, most exciting, call it like 12 months of my life in terms of my work life. Sorry, I don't want to wait with two children and I'm married, so I need to correct myself.

**Mike Reilly** (3:44)
We can edit that out. We'll get the AI to edit.

**Jacobie Olin** (3:47)
Yeah, perfect. No, that was an incredible time. I told my wife before all the transactions occurred, that I was going off the war and please don't divorce me for the next 12 months because it's going to be a wild time. So really taking a step back and there's some things I can't share, but the larger transaction of Casago taking Vacasa private, so that was like step one. Then step two was selling off all of the individual Vacasa markets to buyers to buy as Casago franchises. So it was a large endeavor and Steve Schwab was the founder of Casago and really was a visionary through this. Then Joe Riley came in and was the more or less the executioner and really that those second resales would not have happened and not being there. On the Casago-Vacasa front, it was super interesting. So Casago submitted an offer to take Vacasa Private and right as that was happening, and it was like, I don't remember $120 million deal, something that nature, right as that was happening, a company called Davidson Kempner, DKP, was a minority shareholder of Vacasa and there ended up being kind of a battle behind the scenes and then it ended up spilling out publicly to an extent of DKP submitting higher offer and then, or Casago submitting a higher offer and then it was going back and forth and back and forth and you could go into Vacasa's investor relations and literally watch it play out day by day and they were having to send emails back and forth aboard and it was wild and if it was a $50 billion deal or $100 billion deal, like it would have been front page news of every news station and article all across the country, but it was just a tiny $100 something million deal. So the only press it got was from within our little tight, goofy industry. But it was pretty cool to watch that happen back and forth and ultimately Casago won that bid and the shareholders voted for them to take Vacasa private. Once that happened, Vacasa was in some challenging times. I think we all understand that. I think they were 95 plus percent down from when they went public a couple years earlier. So the clock was ticking for selling off these markets to individual franchisees. And that was Roy Steve's vision there was to really bring the ownership back to the local level kind of where it belonged versus Vacasa's centralized strategy that they had done.

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