In January 2014, I was rapidly building up the number of spaces in our portfolio at M-Spaces. We got over $1M ARR! (As a refresher, we would lease apartments, furnish them, and then exclusively use the apartment to host guests on AirBnB).

I was in contact with Mark Cuban at the time. Was by far the most helpful investor I ever had. I don’t think a single email I sent went without a reply for longer than 15 minutes.

He agreed to a $150k convertible note (in hindsight, I obviously should’ve asked for more). They wired it to my bank account.

During the wire transfer, I had a walk with [Bob Metcalfe]. He said “Don’t count the check until it’s in the bank account.” At the time, I thought it was hilarious.

The wire bounces! The name on the wire was for M-Spaces and the name on the bank account was Monk Group, a general LLC I used for a broad range of business. M-Spaces was still being incorporated in Delaware.

This is exactly what happens to Richard Hendricks in the first scene of Silicon Valley

That blow was enough for Stephen, Mark’s portfolio manager that I was working with. He backed out of the deal, and eventually Austin passed a law that essentially requires you to own the spaces that you’re hosting from, so I shut M-Spaces down. We still have a good relationship, so I’ll probably work with Mark again in the future.

Ultimately, Mark made the correct decision. I don’t think the 150k wouldn’t have affected the incoome.