7. My Trailer Rental Journey: Mistakes, Lessons, and What I’d Do Differently

This episode is different.Instead of another success story, I’m sharing my own journey into the trailer rental business. And it’s still a work in progress.From buying my first trailers to dealing with damage on day one, chasing “passive income,” and realizing I wasn’t marketing nearly enough… I break down what actually happened.If you’ve ever thought about starting a rental side hustle, this is the honest version, not the highlight reel.I cover: Why I got into trailer rentals in the first place  The biggest mistake that cost me money  What I misunderstood about “hands-off” income  Why my business grew… then slowed down  Marketing efforts that worked (and didn’t)  Lessons from buying the wrong equipment  What I would do differently if starting today  The decision I’m facing: go all-in or get out This isn’t a polished success story. It’s a real look at building something that hasn’t fully clicked yet and figuring out what comes next.If you're in the middle of your own journey, this one’s for you.