Everybody wants a deal
For years, my wife and I traveled the world full-time (wrote this book about it) and we stayed exclusively in Airbnbs. Having a kitchen meant we could cook at “home” instead of eating every meal at a restaurant, which matters a lot when you’re on the road for years at a time.
The problem? The good Airbnbs are really expensive.
The mortgage on our house in Florida (taxes and insurance included) runs under $2K a month so having to pay $5K to $8K a month for a much smaller apartment felt insane. So I started negotiating with Airbnb hosts, and it worked better than I ever expected.
In one year, I negotiated nearly $100K off Airbnb rentals. I posted this on social media:
Once I realized what I’d figured out, the next question was obvious: plenty of other people stay in Airbnbs so why not teach them how to do this too?
The fancy term is: Knowledge Productization.
So I made a course!
Sitting inside some of those very same negotiated apartments – and at one point, filming at the top of the Acropolis in Athens – I put together an eight-lesson video course (with copy and paste scripts) walking people through my exact negotiation process. I added bonus videos, packaged it up, and sold it through Gumroad.
Here are just a few of the promo videos and BONUS videos:
What I learned
Gumroad makes it really easy to sell a digital course without building a website. I also got significantly better at video production (Final Cut Pro with 360-degree videos) while creating this course.
Why the black shirt?
For reasons I still can’t explain, I convinced myself I had to wear the same black button-down shirt for (nearly) every lesson. Every single one. It added absolutely nothing.
Why I shut it down (2022)
This one’s a little different from the usual “here’s what I’d do differently” section.
I shut it down because I felt bad.
At one point during our travels, we rented from a family who genuinely went out of their way to take care of us. They treated us like we were family, not just an Airbnb booking. They helped us with local recommendations, gave us rides and even cooked us dinner a few times. They were always so happy and pleasant to be around. And I couldn’t shake the feeling that I’d used my negotiating skills to take thousands of dollars away from them. I didn’t want anyone to ever do that to them again.
So I pulled the course.