Most Entrepreneurs Start Companies. The Smart Ones Buy Them.

Most entrepreneurs chase invention. Smart ones sometimes choose acquisition.

Consider this:

• 90% of startups fail.
• 80% of small businesses survive five years or more.
• Millions of baby boomer–owned businesses will change hands this decade.
• Many of those businesses already work but need new ownership.

This isn’t a knock on startups. It’s a reminder: the math often favors buying over building.

JMM: Just make money

I was once that founder with a napkin sketch and a spreadsheet: collecting domains, entering pitch competitions, driving across country to California and dreaming big.

Then I watched my father’s friend retire from dentistry at 53 and buy a small sheet metal company for 3x earnings. He’d never run a manufacturing business. Put down 10%. Had spent his entire career looking at teeth, not running a factory floor.

A year later, he was making more than he did in his entire twenty-five-plus-year dental career.

That changed how I saw entrepreneurship. Why was I trying to invent something…When I could buy something that already worked?

The biggest marketplace in the world

Every day, 10,000 baby boomers turn 65. Many own businesses, real ones like machine shops, clinics and distribution firms. Not unicorns, but durable.

Six million of these businesses will need to change hands this decade.

Most fall into a quiet lower end of the middle market:

• Valued at $500K to $5M
• Too small for private equity, unless there’s a roll-up in play
• Too boring and stable to attract VC
• Too unloved to spark a bidding war

Many sell for 2–4x earnings.

Three paths to ownership (Without being rich)

People hear “$2.5 million business” and stop listening. But buyers don’t pay full price out of pocket.

Path 1: The Bootstrap Buy

Use the business’s own cash flow. I bought my first company with 10% down, raised from friends and family. The seller carried 40% as a note. Banks covered the rest. My out-of-pocket? Less than a new car.

Path 2: The Partner Path

Some investors aren’t chasing unicorns; they’re looking for steady. Retired execs. Small family offices. Owners who’ve already had a win. A 20% return from a stable business beats most alternatives.

Path 3: The Creative Deal

One person I know bought a $3 million HVAC company with zero down. The seller stayed on. They split profits 50/50 for two years. Ownership transferred once the handoff was smooth.

Stop thinking like an employee who needs cash up front. Start thinking like a dealmaker who creates wins for everyone.

Related: How I Built a Framework to Accelerate Product-Market Fit

A shift in the landscape

Four trends are changing what it means to become an owner:

1. The Retirement Wave

By 2030, every baby boomer will be over 65. Many still own the companies they built.
Most don’t have a plan for what comes next. They’re not looking to grow. They’re looking for an exit.

2. The Financing Shift

Seller financing used to signal distress. Now it’s common. SBA loans are accessible.
Banks are open to small, cash-flowing deals again. Structures that seemed exotic 20 years ago are now standard.

3. The Remote Revolution

Geography matters less. You can run a manufacturer in Ohio from Denver. I once commuted to Pennsylvania from California. United Airlines was my office.

4. The Startup Slowdown

Capital is getting pickier. A business doing $2M in EBITDA looks better than a startup with $0 revenue and a $20M cap table. While most entrepreneurs pitch VCs, thousands of profitable businesses wait quietly for their next owner.

How to think like an acquirer

Builders chase ideas, but acquirers chase working systems.

1. Start with industries that have recurring revenue, fragmented players, and low capital needs like HVAC, pest control, or property management.
2. Look for stable businesses run by retiring owners, not failing ones.
3. Pay for current cash flow, not future hopes.
4. Structure deals with seller financing or earnouts to keep transitions smooth.

The real opportunity is to buy boring, steady businesses, then run them better. That’s how you skip the risky early stages and start with customers who already pay.

Related: Skip the Startup Struggle — Here’s How Buying a Business Lets You Profit Sooner

Ask “what could I buy?”

Most entrepreneurs start by asking: “What could I build?”

It’s a fair question if you’re drawn to invention. But there’s another question worth asking: “What could I buy?”

When you build, you’re betting on:

• An unproven idea
• Customers you haven’t met
• Economics you hope will work
• Yourself, starting from zero

When you buy, you’re betting on:

• A model that already functions
• Real customers with repeat behavior
• Financial history you can inspect
• Your ability to improve, not invent

One isn’t better. But one starts with momentum. Buying isn’t easy. You’ll lose deals. You’ll spend money and come up short. You’ll feel the weight of leading people who didn’t choose you.

But you’ll also walk into something that works. With a team. A reputation. A rhythm.

And maybe that’s all the permission you need to begin.

The path forward

The best time to buy a business was ten years ago. The second-best is now. Are you an entrepreneur who needs to invent? Or one who needs to own?

Some people need to start from scratch. But if you care more about freedom than fame, more about cash flow than cap tables, and more about ownership than originality, then there’s another way.

The businesses are out there. The owners are ready. The math is in your favor.

Get out there and JMM.

Most entrepreneurs chase invention. Smart ones sometimes choose acquisition.

Consider this: