From Cold Calls to Conversations

A Better Way to Source Deals

In partnership with

Hey Investors,

Last month, I shared what I learned from calling 10 porta potty business owners.

Since then, I’ve gone deeper—and hit some walls.

To broaden my search, I started combing through Chamber of Commerce directories. They're often organized by business type, so I figured I could scan for industries that fit my buy box: steady demand, simple ops, and room for improvement. That led me to one that seemed promising:

👉 Storage (self-storage, boat/RV parking, etc.)

These are high-demand, asset-heavy businesses with minimal maintenance and strong margins.

What’s not to like?

So I picked up the phone again. And this time...a lot of owners were angry that I called.

Like really angry.

💡 Quick Note: Is Self-Storage Just a Real Estate Play?

Pretty much—but with one big advantage.

Buying a multiunit apartment complex usually requires a commercial loan with 25% down.

But self-storage? It often qualifies for an SBA loan, meaning just 10% down.

That small difference gives you serious leverage.

Same capital, 150% more buying power.

But there’s a catch:

SBA loans require a personal guarantee.

If the business fails, you're still on the hook—personally.

Know the upside. But be clear on the risk.

❌ The Old Approach: “You selling?”

My initial strategy was straightforward: call the owner, ask if they were thinking about selling in the next few years, and then ask a few questions about their business to qualify them.

I figured the direct approach was the best approach.

I was wrong.

It turns out owners in this industry get called dozens of times per week. Usually by big private equity firms that have quite a lot of money to spend.

I wasn’t doing anything wrong—but I was adding to the noise.

Given the competition and negative impact it had on owners, I did the only sane thing:

I pivoted.

✅ The New Approach: “Can I learn from you?”

Instead of asking about deals, I started asking for wisdom.

  • “What’s it like running this kind of business?”

  • “What’s something most people misunderstand about your industry?”

  • “If your kids were going to take this over, what would you want them to know?”

Almost immediately, the tone changed.

People opened up. They told stories. They gave honest, hard-won insights. Some even offered to introduce me to others.

💡 The Bigger Realization

Sourcing opportunities isn’t just about finding businesses—it’s about building trust.

Even if someone’s not ready to sell, they might know someone who is.

Even if they never sell, they might teach me something that shapes the next deal.

And honestly? It’s more fun this way.

I'm learning. I'm connecting with cool people. I'm building a network that money can’t buy.

You just can’t beat that.

If you're a business owner in Michigan and want to share your story, I'd love to hear it.

No pressure, no pitch—just a real conversation.

Just hit reply.

—Dakota

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