Striking Out on My First Attempt

One of the driving forces behind leaving my W2 job was to buy back my time. For me, time has always mattered more than money because I have wide interests and zero tolerance for wasted energy.

About ten years ago, my wife and I made our first trade in the money-for-time equation: we hired a housekeeper. It wasn't always consistent at the start, but over the years, we found someone reliable who has now cleaned our home every other week for the past eight years. That decision alone accounts for nearly $40,000 spent on a single service. A service that gave us back hours of time and mental bandwidth.

Recently, I came across Codie Sanchez's "Venmo Challenge." The idea is simple: look at the small businesses you already spend the most money on. If you think you could own and grow one of them, start there.

By that metric, housekeeping topped our list. It seemed like a natural starting point. But the service we use is a franchise and that doesn't fit my deal box. One of the biggest reasons I left corporate America was to escape bureaucracy, egos, and regain creative freedom. I didn’t want another boss, even a franchisor. When I explored a failing business that turned out to be part of a national franchise, the long list of limitations reaffirmed that this path wasn't for me.

So I thought more broadly. Where else do I spend money locally? What other businesses do I respect, even admire? That brought me to another candidate, albeit with a much lower spend: a self-service car wash that I frequent after every overlanding trip.

My interest in car washes didn’t come from online trends since all the vending machines and laundromats have dried up. It started in 2021 at Overland Expo East in Virginia. One evening around a campfire, I chatted with a retired auto worker with an incredible off-road setup. As he shared stories of international travel, someone asked how he funded it all. His answer? Car washes. He owned several. The years they did well, he traveled the world. The years they didn’t, he stayed stateside. That conversation stuck with me. How can I create this freedom?

Years later, I still hadn’t forgotten it. I started frequenting a local self-service wash to keep my off-road vehicle clean. I often saw an older man taking out the trash and wondered if he was the owner. But I never had the nerve to approach him directly.

Instead, I turned to the internet. I found the property owner’s name and address and sent a handwritten letter with a photo of my rig. I explained who I was, why I was interested, and what I hoped to explore. As scary as it was to drop it in the mail, I reminded myself that the worst thing that could happen was they say 'no' or not even respond. This was re-affirmed with the book Things That Matter and some quotes I really liked, such as "So many people would rather be disappointed and unfulfilled doing things that are safe than go through the anxiety of chasing valuable dreams and goals. Sadly, they prefer a safe, meaningless status quo over taking a risk that might lead to failure- or might lead to success."

A few days later, I received a voicemail:

"Good morning Paul, this is [name] from [business and location]. I received your letter yesterday and I appreciate your interest in wanting to purchase businesses for yourself and your wife, particularly my business. However, as of now, I have absolutely no interest in selling the business in the foreseeable future. I'll keep your phone number and information on hand. If when you are there washing your truck and you see me, please walk over and introduce yourself. Best regards, [name]."

I haven’t seen him since, but I will introduce myself when I do.

Since then, I’ve continued reaching out to businesses. Sometimes I reach out by email, sometimes by traditional mail. Some business owners respond. Some don’t. And that’s okay.

This process is part of a bigger journey. I’m not just looking to buy a business. I’m intentionally designing a life where ownership gives me back my time, my creativity, and my freedom. Every person I reach out to is a small step toward that vision.