Castro's $2M Podcast Loss

Andrew Wilkinson shares a story about his worst investment - buying a podcast player called Castro and losing money due to lack of focus and strategy.

"My worst investment this year was actually from about 5 years ago. It's a great example of shiny object syndrome, lack of focus, and what I call a money bonfire.

I bought a podcast player called Castro about 5 years ago. At the time, I was really hopped up about podcasts and subscription podcasting. It was around the time I started coming on MFM actually. I bought the business because I was excited about the space, not because I had a plan.

The business basically just languished. The founders left, I couldn't find anyone to run it, and just every month it lost 10 to 20k. It was a small enough number that blended into all my other stuff - I just didn't really notice it, it wasn't an urgent thing. This tiny little ember turned into a money bonfire.

I think I lost $2 million over the last 5 years on this business. Now I'm in the process of selling it. It's one of those things where I've done this so many times - I start something and it's a runaway train. I just don't get the right people in and it slowly burns money."