Excerpt from Boring F*Cks – Investors Are Getting rich off businesses you’ve never heard of

You wrote a check three years ago. $25,000. Maybe $50,000.

You haven’t seen a dollar back. You probably never will.

You don’t talk about this investment anymore.

You wince a little when the founder posts on LinkedIn.

The company sounded right. The founder was sharp—former Google, Stanford MBA, the usual signals. The deck was tight. The market was “massive.” Someone you respected was already in. The round was closing Friday.

You wired the money Thursday.

Now you’re on a cap table you don’t fully understand, holding shares you can’t sell, in a company that’s raised two more rounds—each one diluting you further. The founder is “exploring strategic options,” which means they’re trying not to die.

You’re not an investor in that company. You’re a hostage.

You’re not dumb. You just played a game you didn’t understand, on someone else’s terms.

That game is the Excitement Delusion.

I Know Because I Did It Too

I’ve written those checks.

Early in my investing life, I put money into a startup over two years. It was an AI tool for mental health targeting unhoused individuals.

I remember refreshing my inbox waiting to hear if the “big customer” had closed. I remember telling my friends “it’s fine, this one’s more about the relationship.” I remember the slow, quiet moment when I realized I’d never see that money again—and that I’d done it to myself.

The company died. Total invested well into the 6-figures. Total returned across all three: $0.

I didn’t lose that money because I was stupid. I lost it because I was playing a game designed for institutions, using my own cash as the entry fee.

That’s when I started asking a different question.

Not “what’s the upside if everything works?”

But: “How reliably will this pay me back?”

That question killed every exciting deal I looked at. And it opened a door to a completely different kind of investing—one that actually works for people like us.

This book is what I learned on the other side of that door.

Path A and Path B

Here’s the fork in the road.

Path A: You put $50,000 into a startup. It’s exciting. It’s “disruptive.” It might be huge. You wait. You hope. Three years later, you have nothing but a PDF cap table and a founder who won’t make eye contact.

Path B: You put that same $50,000 into a boring cleaning company that’s been profitable for a decade. Nothing sexy. No pitch deck. Just a business that cleans offices and deposits checks. You get a few thousand a month in distributions until you’ve got your money back plus a chunk on top. Then it keeps paying.

No miracles. No hoping. Just cash, moving.

One path is a lottery ticket. The other is a machine.

Right now, Path B might sound unrealistic—like something that exists for other people with better deal flow or insider access. That’s fine. This book is about exactly how to find those businesses, evaluate them, and structure deals that actually pay you.

The Test

The Excitement Delusion isn’t stupidity. It’s a set of emotional triggers that hijack smart people. Here’s how to know if you’re caught in it.

You’re in Excitement Delusion if:

☐ You’ve invested in something you can’t explain in one sentence to a skeptical friend

☐ You’ve written a check because a round was “closing soon” and you didn’t want to miss it

☐ You’ve held an investment for 2+ years, received $0 in cash, and couldn’t exit if you wanted to

☐ You’ve celebrated a company raising another round—which diluted you—as if it were a win

If you checked two or more, you’re not an investor. You’re a fan with a brokerage account.

If you checked even one, you’ve already paid a tax to excitement.

The Math You’re Actually Playing

You deploy $125,000 into exciting deals over a few years. Five checks of $25,000 each.

Here’s what happens:

• 2–3 go to zero. Company dies or fades into nothing.
• 1–2 return something—maybe 1x, maybe 2x, after 5–7 years if you’re lucky.

This math “works” for funds that write 200 checks and collect management fees while they wait.

You’re not a fund.

You don’t write 200 checks. You don’t collect fees. You don’t have institutional LPs with 30-year horizons absorbing your losses.

You have your own money, your own timeline, and a spouse who asks uncomfortable questions.

Individual angels aren’t playing the power law. They’re playing hope one hits. And hope is not a strategy.

Now run that same $125,000 through Path B.

You put the money into two boring businesses. Nothing fancy—a commercial cleaning operation and a small service company. Both have been profitable for years. You structure simple deals: you get paid quarterly, in cash, from actual earnings.

Year 1: Cash starts coming back to you. Year 3: You’ve received a meaningful chunk of your principal. The assets are still working. Year 5: Depending on how you structured it, you may have returned your full investment—and you still own the equity.

What “Durable” Means

I’ll use the word “durable” a lot in this book. Here’s exactly what it means:

Durable Investing = putting capital into assets that:

1. Are designed to pay you cash within roughly 12–24 months—not “eventually,” not “at exit”
2. You can explain in one sentence—”they clean buildings and people pay them monthly”
3. Don’t require a greater fool—the return comes from the business, not from selling to the next guy

Three criteria. That’s the filter.

Most exciting investments fail all three. They don’t pay cash for years. They require jargon to explain. And their entire value depends on someone else paying more later.

Durable investments are boring. They’re explainable. And they pay you in cash, not stories.

What This Book Will Do

If you don’t change how you invest, here’s your next ten years:

Locked-up capital. Bullshit quarterly updates. A portfolio you’re embarrassed to explain at dinner.

If you do change:

Ten years from now, you have a stack of boring assets sending you checks, from businesses you can explain in one sentence.

This book shows you how to find these deals, evaluate them like an operator, structure them so you’re protected, and build a portfolio that pays you while you sleep.

Not because it’s exciting.

Because it works.

Turn the page. You’ve paid enough tuition.

📥 TOOLKIT REFERENCE Score yourself and any deal using the “Excitement Delusion Diagnostic.” Download at azgari.org/calm-investor-toolkit

Frequently Asked Questions

How do I start a service business in 2026?

Start by choosing a service type based on demand, skills, and startup costs. Then register your business, get required licenses, purchase equipment, set up insurance, and begin marketing to your target customers.

What’s the most profitable service business to start?

Profitability depends on your market and execution. High-margin services include HVAC, plumbing, electrical, and specialized cleaning. Lower-cost startups like pressure washing and lawn care can also be highly profitable.

How much money do I need to start a service business?

Startup costs range from $5,000 for basic services (cleaning, lawn care) to $100,000+ for licensed trades (HVAC, plumbing). Many profitable businesses launch for $15,000-$30,000 with essential equipment and marketing.

Do I need experience to start a service business?

No, many successful owners started with zero experience. Learn through training, shadowing, and starting with simpler jobs. Business skills often matter more than technical expertise, which can be hired.

How long until a new business is profitable?

Most service businesses can be profitable within 3-6 months with consistent effort. Breaking even typically happens in 6-12 months. Building to full income replacement usually takes 12-24 months.

Should I buy a franchise or start independently?

Independent businesses offer more control and no royalty fees (5-8% ongoing). Franchises provide systems but limit flexibility. For most service businesses, independent ownership with proper guidance provides better returns.

Related Reading

• Complete Guide to Service Business Startup Costs
• Hidden Costs of Buying a Franchise
• How to Get an SBA Loan for a Service Business

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