What Would You Tell the Paul from Six Months Ago?

Song Lyrics from the Band Sleep Token for the song Past Self

This was the question my coach just asked me in our last session. It’s because I just passed the six-month mark of leaving the rat race of corporate life to go out on my own. Although I covered what month six looked like in my last update, I also wanted to summarize the full stretch.

As I mentioned in my first-month check-in, this journey was “a blend of short-term, therapeutic projects, converting side hustles into streamlined revenue streams, and a long-term, strategic play to acquire a small business.” I had my hands in a lot over the past few months, and while I enjoyed the freedom to work on whatever inspired me each day, it also wasn’t focused on any one thing.

My coach could tell something was different with me, and I think she wanted to compare today’s Paul to the version she met several months ago. Between my body language and my words, I could tell something had shifted too. I talked about feeling like I have a purpose, a mission, something to drive toward. She could see and feel the excitement.

After six months of exploration and experimentation, the answer to what I needed to be doing was right in front of me: Radio Chatter.

If I take a step back and reflect on why I went into entrepreneurship, it was to build more time into my life and design a lifestyle I wanted to live. One of the key things I love is being outside and going on adventures. I do that through overlanding (car camping meets off-road adventure) and the dedicated vehicle we’ve built to take us on those trips.

So How Did I Answer Her Question? Two Parts:

1. Talk to Your Friends TAM and SAM

First, I would tell past Paul: before discounting an idea or pathway, fully understand the opportunity. This is obvious in hindsight. Understand your TAM/SAM (total addressable market | serviceable available market). I’ve coached this stuff in Design Thinking workshops!

Since we started Radio Chatter, we always said it was just “fun” and “not something we plan on retiring on.” I found those exact quotes when I was updating our website, which links to one of our first interviews with our partners at Midland. I also talked about this mindset shift in a previous post about our “Silly Card Game,” which is what we often called it.

But here’s the reality: I spent time researching this past month and found the Overland Expo industry report. In the U.S. alone, 2.9 million people call themselves "overlanders." Not only that, 8 million people took an “overlanding trip,” and that number is expected to reach 12 million in 2025 and beyond. That doesn’t include "off-roaders" who may not identify as "overlanders," though they still fit within our product’s demographic. Those overlanders also spend an average of $500 a year on gear.

Some basic math says we only need a fraction of a percent of this market, and just a few percent of their yearly spend, to have a strong small business. This doesn’t include international business, where we’ve already shipped physical product to Australia, South Africa, Canada, and the UK. Our mobile app has been purchased in Australia and Canada too.

I was listening to the Problem Solvers podcast and an episode called Why Many Companies Fail, and How to Avoid It. The guest, Arjan Singh, was talk about business assumptions and what he sees as the three business killer assumptions:

Market Assumptions
Competition Assumptions
Assumptions about Yourself

My biggest learnings over the last three months specifically were around market and myself. I believed the overlanding market wasn’t big enough to sustain the lifestyle we’d built with two comfortable salaries. And I believed we couldn’t build our company into something sustainable for such a niche market. It was always going to be a “fun side hustle.”

Sometimes You Have to Go Through It

The second thing I’d tell my past self is that you have to go through this experience, even if it hurts to think about what could have been accomplished with Radio Chatter if it had been the priority from day one.

I had wanted to buy a business long before Radio Chatter, so that was something I had to explore to realize it might not be for me. I also needed to experience life without a steady income to see what truly matters to me and my family.

Early on, in my Clarity in the Climb post, I wrote about my values: Legacy Through Leadership, Alignment Over Achievement, Clarity Before Motion, Educating & Uplifting Others, Continuous Learning, and Exploration & Experimentation.

As the six-month mark approached, I faced a big decision: should I focus solely on building Radio Chatter, or keep it as a side hustle while pursuing business acquisition or something else as my main path? After working on everything for half a year, it was time to commit.

Business acquisition was still a real option this whole time. I’d been discussing one company with partners since day one, and the talks had just been reactivated in October after months of silence.

Looking at my values, especially Alignment Over Achievement and Clarity Before Motion, the answer became clear. It also showed up in a text exchange with my business partners. We had gone back to the bank with a new financing request under different terms. When their response was lukewarm, we had to decide whether to keep negotiating or seek private financing.

My reply (after a few days of silence because I was at Overland Expo East) was:

"I've been racking my head back and forth on this though on what I want to do personally. At this point, I am just not interested in putting what they require on the line because honestly, I don't ‘need’ this business or the income from it for my future. So why would I risk what I have for something I don't need?"

That hit me hard as I wrote it. It didn’t align with my values, especially Alignment Over Achievement: “I prioritize values, integrity, and life design over titles or career ladders. Success means saying yes to the right things, not just more things.”

Yes, I’ve always wanted to own a business (I do, with my wife), and I’ve always wanted to buy a business, but just because I’ve wanted it doesn’t mean I need it.

Just because a dream starts one way doesn’t mean it has to stay that way. Even though I love being busy and once imagined myself as a serial entrepreneur bouncing between ventures, that’s not the life I’m designing for anymore. That was the life of Paul before this journey was designing for.

When I step back and look at the past six months, I’m not as far along financially as I expected to be, but clarity-wise, I’m ahead. I’ve also accomplished more than I expected. Let's take a step back and look my back needs a good ol' 'at a boy' kind of pat.

Created and launched the Apple mobile app version of Radio Chatter (Android is nearly complete).
Evaluated about a dozen businesses for acquisition, including executing an LOI and completing due diligence on one. Not many people can say they have done that.
Took second place in an OpenAI/ChatGPT hackathon.
Supported Mountain State Overland by planning the route for Hammer Down 6 and helping lead Adventure X Fest - something I would never have had time to do with my past job.
Taught a class about creating an overlanding side hustle at Overland Expo Mountain West.
Had great conversations with others pursuing similar paths, including a talk for BizHives on the importance of having a career coach.
Spent a full week tearing apart and rebuilding my truck to install much-needed upgrades before a big trip.
Went impromptu fishing for a few days with my father, brother, and brother-in-law. I was able to leave mid-week to balance my busy weekend of coaching kids sports. Not possible with my past job.

So, past Paul: you may not be where you thought you’d be, but the future is bright, and you’re designing a life that’s true to who you are. Send it.