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The Real Challenge — Picking the Right Business

Hey Investors,

This week, I’ve been deep in the trenches and wanted to share a behind-the-scenes update.

When I pivoted into buying a business, I ran into a challenge that trips up a lot of smart would-be entrepreneurs:

👉 “I don’t know what business I should buy.”

It sounds simple — but it’s not.

There’s a massive gap between “I want to own a business” and “I know exactly what kind of business will set me up for long-term success.”

This is where a lot of corporate escapees and first-time buyers get stuck. And I did too — for a while.

But instead of staying in analysis paralysis, I made a decision:

Take deliberate, imperfect action — and let clarity emerge through doing.

And guess what? It worked.

My Criteria — And What I Chose

I asked myself a simple question:

What kind of first business will stack the odds in my favor?

Here’s the criteria I landed on:

✅ Generates strong cash flow
✅ Has steady, durable demand
✅ Operationally simple (no tech complexity, no crazy staffing headaches)
✅ “First deal friendly” — something that builds early wins and confidence

After a lot of research and filtering, one model stood out:

👉 Porta potty rentals.

Dear reader, I can see your face now:

“Seriously, Dakota? Porta potty rentals? You’re nuts!”

I won’t argue with you, but it DOES check every box:

→ Recurring revenue by renting access to hard assets
→ Asset-heavy, which makes bank financing easier
→ Demand is constant — construction, events, municipalities always need capacity
→ Simple to operate, with clear cost structure and service model

It’s one of those unsexy but excellent businesses — exactly what I was looking for.

You’re probably thinking:

“Okay, okay, I get what you’re saying, but how do you KNOW this is the right business?”

Great question, here’s my answer: I don’t!

It’s not about making the RIGHT or WRONG choice.

It’s about gathering just enough information to move fast and learn.

And in that regard, it’s good enough.

So here’s the next step…

How I’m Sourcing Deals (This Week’s Progress)

I can talk about buying businesses all day long, but that’s meaningless unless I have a plan for locating and initiating deals.

So with my target niche locked in, here’s what I did this week:

1️⃣ Built a comprehensive list of every porta potty rental business within driving distance
2️⃣ Prioritized by proximity to reduce logistics overhead
3️⃣ Researched employee count, revenue, and digital presence to gauge sophistication and potential fit
4️⃣ Narrowed it to a Top 10 list of targets — these are the owners I’ll be contacting first

Next step: start calling, build relationships, and open conversations.

Some will be ready to talk now. Some won’t. That’s fine — this is a long game.

Why Share All This?

Because so many of you are on the same journey:

→ You want to own a business
→ You want more freedom and control
→ But you’re stuck at “where do I start?”

I’m sharing this play-by-play because I want to show what it actually looks like to build your first acquisition path.

It’s not perfect. It’s not magic. It’s just consistent action, applied intelligently.

(And my fair share of courage to look stupid while I figure it all out.)

More updates soon — onward,

Dakota Crisp, PhD

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