Starting a Business in the Middle of Nowhere

Happy Tuesday!

Quick, before we begin, my buddy Grant and I just vibe coded something pretty cool. It’s a simple chat-based invoicing tool that generates a PDF invoice and payment link instantly, from 1 simple prompt.

We’re looking for a beta testers to give some feedback! Click here for early access: invoicefreely.com 

Okay, let’s get into it.

Last month, I threw a dart at a map of Texas. It landed on a tiny town called Flats.

I made myself a promise: I couldn't come home to see my kids until I doubled whatever money I started with. No audience leverage, no internet business shortcuts, no backing out.

What followed was eight hours of rejection, awkward door knocking, lukewarm sales, and one of the most satisfying $30 I've ever earned.

I wanted to break down some of the major lessons and takeaways… and why it matters for anyone thinking about starting something. You can also check out the full episode here: YouTube. Sometimes you just need to see someone doing it to believe it's possible.

Alright, so, I drove two hours from Dallas with $20 in my pocket. My rule was simple: double my money through legitimate business before I could go home. If I bought something for $200, I had to sell it for $400 before leaving. No exceptions.

Flats turned out to be an intersection. Literally. One stop sign. A few mobile homes. A guy with a "I'd turn back if I were you" sign on his property.

So I drove into Flats proper and started knocking on doors.

Puppies:
That's when I met Danny-the self-proclaimed "Rascal of Flats" and he had a problem: five pitbull-lab mix puppies whose mama got hit by a car when they were three weeks old. He'd raised them himself, but he knew they'd get run over too if he didn't find them homes.

"I don't know how to turn on a computer," he told me.

I saw an opportunity. What if I listed them online and found buyers?

Facebook doesn't allow pet sales. I got blocked immediately. So I pivoted. I joined every Emory-area Facebook group and posted about free puppies needing homes. People commented with interest but ghosted my messages.

Finally, a woman responded who places rescue puppies as a passion project and drove two hours to Danny's place. He decided to keep three of them (he'd gotten attached), so she took two.

Not a perfect ending, but way better than five puppies getting hit by cars.

The Rejection Loop:
After leaving Danny's place, I started knocking doors in earnest. Here's what nobody tells you about door-to-door sales: it's brutal.

"Just had it done." "That's my job." "Not a good time." "We stick to ourselves."

I offered gutter cleaning, pressure washing, weed eating, window washing. Nothing. My friend Kyler drove out to help, and we tried a different angle. We posted a pressure washing service on Facebook Marketplace. Still nothing.

Then we shifted strategy. Instead of targeting homes without landscaping (people who clearly didn't value it), we looked for homes with nice yards. The logic: someone maintaining six fruit trees is already thinking about what else they could add. Someone with a dirt lot doesn't care.

That reframe led us to Leah.

beehiiv just dropped their biggest update. Ever. And it’s going to be HUGE for digital creators. They released dynamic podcast websites, AI website builder, native analytics, direct digital product sales with zero commission, and link in bio.

If you’re a creator, you’re probably paying for seven different tools right now. Your newsletter platform, a separate website, Podpage, Gumroad, Calendly, Google Analytics, Linktree. That's what.. five hundred bucks a month? Minimum? And none of them talk to each other.

beehiiv just replaced all of that with their one platform. One subscription. Everything integrated. Head to beehiiv.com/Chris and use the code CHRIS30 to get your 30% off your first 3 months. If you're still using another newsletter platform, you're wasting time and bleeding money.

Lawns:
Leah was mowing her lawn when we walked up. She looked miserable doing it. I offered to finish the job for $20.

She said yes immediately.

One hour later, I had the best-looking lawn of my amateur mowing career. She handed me $30. A $10 tip because, in her words, "You made my day."

That $30 represented everything. Not just the money, but the validation that someone would pay for help. That the value exchange worked. That I could earn without asking permission from an algorithm or an audience.

I own my time. I own my paycheck.

Waters:
We still needed to double our original $20. So we went to Dollar General. We had $10 left after gas, which bought us a poster board, a Sharpie, and 32 bottles of water for $5.

The county fair was happening that night. Water costs $3 inside. We stood outside with our sign and sold bottles for $1 each. No cooler, no ice, just room-temperature water and a story.

"Every no is closer to a yes" became our mantra.

People walked past. We got ignored. We got flat rejections. But eventually, someone bought three bottles. Then another person. Then a guy bought three more. By sunset, we'd sold enough. $38 total. More than double what we started with.

I could finally go home.

Alright, these side hustles aren’t quite as sexy and flashy as the ones I typically share, but they teach some major lessons:

1. Constraints force creativity.

I couldn't use my audience. I couldn't start an internet business. I couldn't go home until I succeeded. Those limitations forced me to think like someone with nothing. That's exactly the mindset most people need when starting out.

2. Sell to people who already buy.

Don't pitch landscaping to someone with a dirt yard. Don't offer services to people who've never paid for services. Find the person already mowing their lawn who clearly hates it. That's your customer.

3. The story sells better than the service.

"I charge $20 to mow lawns" is a commodity. "I threw a dart at a map and can't go home until I double my money" is a story. Leah didn't just pay for a mowed lawn. She paid to be part of something interesting. People buy the why.

4. Every platform has arbitrage.

The fair sold $3 water we bought for 15 cents. These gaps exist everywhere. Your job is to find them and bridge them.

5. Rejection is data, not judgment.

Fifteen “no”s taught me what didn't work. The sixteenth door was Leah. If I'd stopped at ten, I'd still be in Emory. Don’t give up.

Your Move:
You don't need to throw a dart at a map. But you might need to manufacture your own constraint. What if you couldn't use your network for your next business idea? What if you had to make your first $100 this weekend? What if you couldn't go to bed until you'd talked to 10 potential customers?

Constraints reveal what you're actually capable of when the safety nets disappear.

I went to Flats with $20 and came home with $38, puppies rescued, and a reminder that entrepreneurship isn't about viral hacks or passive income.

It's about knocking doors until someone says yes.

Speaking of finding of what you’re actually capable of: I've been building a private community called TKOwners for people interested in starting real businesses. We have a slack channel where we drop insane AI tools and possibilities everyday.

If you want to start your own business, or make your current one more successful, this is your place. We help people who are ready to do the work, not just talk about it.

If you're serious about staying ahead of this AI revolution and getting help from top business builders, check it out at tkowners.com.

It's where the hundreds of action-takers hang out. And you could be there too.

And again, if you want to watch the roadtrip, check out the full episode here: YouTube. Sometimes you just need to see someone doing it to believe it's possible.

Get out there and take action. You can just do things.  

Have a great week!

Chris

P.S. I share deep dives on business ideas and complete playbooks three times a week on YouTube and every podcast platform.