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The Rich Somers Report

He Used to Work for Airbnb, Now He’s Developing Boutique Hotels ⎮ Mike Demson E395

The Rich Somers Report

Rich Somers

Investing, Business

5.01K Ratings

🗓️ 6 September 2025

⏱️ 44 minutes

🧾️ Download transcript

Summary

From corporate cubicle to boutique hotel developer—this is how you flip the script. In this episode, Rich sits down with Mike Demson, a former Airbnb employee who walked away from the W-2 grind to build a portfolio of boutique hotels. From spotting undervalued properties to designing experiences travelers actually crave, Mike breaks down how he’s turning his insider knowledge of Airbnb into long-term wealth in hospitality. They cover: Why Mike left Airbnb to go all-in on boutique hotelsThe on...

Transcript

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0:00.0

What's the Warren Buffett quote? Be fearful when others are greedy and greedy when others are fearful.

0:06.0

You know, I think short-term rentals and Airbnbs are great. You have to be differentiated. You have to have some

0:12.5

sort of advantage. You have to understand the market and who your travelers are. But, you know,

0:17.7

what it comes down to is, you know, creating what shifts are coming in the market and then having that vision for multiple years down the road.

0:29.8

What's going to be the next thing?

0:33.2

Welcome to the Rich Strummers Report where we talk real estate, business, and wealth building all while keeping it real. No fluff, no BS. I hope that you enjoy the show.

0:46.7

All right, guys, welcome to another episode of the report today. I got someone who's doing big

0:53.2

things in the boutique hotel investing space,

0:56.0

used to work for Airbnb, and now he's developing and renovating boutique hotels up in Northern

1:01.4

California going all in on this new space. I got my man, Mike Dempson. Mike, welcome to the show,

1:08.6

baby. How are we feeling today? Doing great. Thanks for having me.

1:11.2

I'm so pumped for this conversation, man. So much to cover, so much to talk about with all the

1:15.8

shifts that are going on right now. But first things, first man, used to work for Airbnb,

1:20.1

which I just now learned what the heck were you doing for Airbnb now? It's doing growth marketing.

1:25.4

Worked across email, Google ads, Facebook ads, work with a lot of

1:30.6

influencers and basically, you know, creating content for the brand. And it was a good introduction.

1:36.1

I figured out, you know, what works in terms of design, marketing and just positioning of

1:41.7

and then now today, you're taking advantage of the tightening Airbnb regs, the shifts in Airbnb,

1:48.8

the trends that are going on right now.

1:51.1

Give us big picture right now.

1:52.5

What are you doing in the in the boutique hotel space?

1:54.9

You bet.

...

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