My 5 year plan

Good morning.

It’s time I take a moment and summarily share my goals and mission, and exactly how I think I’ll get there.

Today I’m writing out my 3-5 year plan to capitalize on what I think is the best opportunity in entrepreneurship: off-market, digital businesses owned by Baby Boomers.

Today’s topics:

  • The well-publicized wealth transition

  • The 3% niche I’m targeting

  • My 3-5 year plan (with numbers)

The “Silver Tsunami”

Recent headlines I found discussing Boomer business transitions

Our country is full of enterprising Baby Boomers who are getting tired in the office and growing romantic about the beach.

You probably know some of these folks.

One particular gentleman I know, Jim, owns an HVAC business. He’s about 60 and a second-gen HVAC owner.

He’s tired of driving his service van and spends a lot of time fantasizing about what RV he should buy and drive down to Florida.

Business is solid/fine: low 7 figures revenue, neglected, long-time customer base (which includes folks that followed him from his dad’s business).

Jim is part of the so-called “Silver Tsunami” — the millions of Baby Boomer business owners who will need an exit. Soon.

You’ve heard this story before. Lots of ink spilled over the prior decade talking about it.

And I want to capitalize on this great opportunity!

But the story always, ALWAYS focuses on guys like Jim.

And I have one major problem……

I barely know how to change my own air filter. I ain’t running an HVAC company!

The Boomer business owners I’m targeting

There’s another group of Baby Boomer business owners that don’t make it as subjects of these stories.

They’re nearly unicorns.

They’re the guys and gals who own businesses like Wireless Estimator.

Click the link and peruse that site. You’ll see it’s nothing special on its face.

What’s special about Wireless Estimator is it’s the go-to source for news, jobs, and resources for the $1.5T telecom industry. And it’s been that way for 20 years!

If you’re anyone in telecom, you know Wireless Estimator.

(Side note: I know because I spent a year recruiting tower climbers as a side hustle.)

It’s owned and run by one guy: Craig.

Craig’s been crushing it with Wireless Estimator since 2003.

He’s doing it with his keyboard and his website instead of a wrench and a service van.

There are thousands of folks like Craig out there. I could paste screenshots of conversations with 10 similar businesses that you’ve never heard of.

My totally unscientific guess is 3% of Boomer business owners own a digital-based asset.

For some reason, they don’t get much publicity and not many people know about them.

But I suspect Craig, like everyone else at some point, is thinking about his exit.

And I want to be part of that.

My 3-5 year plan

So here’s what I’m going to do about it.

📌 Mike’s plan to acquire a homerun business

  1. Build a list. 5,000 Baby Boomer-owned, online businesses that aren’t for sale.

  2. Build relationships with 100 of these Boomers. Get curious and take the long view: in-person visits, handwritten notes, coffee meetings.

  3. Write. Share my story and what I’m doing (in this newsletter and on X/Twitter). In the process meet some like-minded people.

  4. Buy a homerun. ~$200k-$500k cash-flow business with loads of potential for an owner with fresh eyes, tech, naivety, and enthusiasm.

  5. Grow. Maximize the business’s cash flow potential. Target: $1m earnings.

  6. Buy again. Use the cash flow to acquire another business from my network of folks who are ready to call it quits.

  7. Repeat ad infinitum. Do steps 2-6 until I get tired and/or content.

To me, the most joy is between steps 2-3… doing something I find pleasure in while meeting some awesome people.

And, that’s you! So, thanks for reading and for the responses. I thrive off them.

Mike