Selling Your First Company: A Founder's Guide

In 2020, I sold The Pressure King—the pressure washing company I started at 16—to a private equity firm. I was 20 years old.

It was surreal. This thing I'd built as a teenager, knocking on doors and washing driveways, was now worth real money to serious investors.

But the process taught me more than the outcome. Here's what I wish I'd known.

The Decision to Sell

Selling wasn't always the plan. I loved the business. But several factors converged:

The Business Had Outgrown Me

At its peak, The Pressure King had:

• Multiple crews running daily
• Commercial contracts with property managers
• Recurring residential customers
• Equipment and vehicles worth six figures

Managing all of this while trying to figure out what came next in my life was overwhelming. The business needed a different kind of operator than a 20-year-old founder.

The Market Was Hot

PE firms were rolling up home services businesses aggressively. Pressure washing, lawn care, HVAC, plumbing—anything with recurring revenue and local density was getting acquired.

When buyers are eager, sellers have leverage.

I Wanted to Build Something New

The itch to start something else was strong. I had ideas for software companies, for disrupting legacy markets, for building at scale. The Pressure King was a great business, but it wasn't where I wanted to spend my 20s.

The Process

Finding Buyers

I didn't use a broker. For a business my size, the fees didn't make sense. Instead:

1. Researched PE firms active in home services
2. Reached out directly via LinkedIn and email
3. Talked to other founders who had sold similar businesses
4. Let word spread through industry contacts

Within a few months, I had multiple interested parties.

Due Diligence Hell

This is where most founders underestimate the work. Buyers want everything:

Category	What They Want
Financial	3 years of P&L, balance sheets, tax returns, bank statements
Operational	Customer lists, contracts, employee records, equipment inventory
Legal	Business licenses, insurance policies, any litigation history
Growth	Marketing spend, customer acquisition costs, retention rates

If your books aren't clean, due diligence will kill the deal or crush your valuation. I was lucky—I'd been meticulous about documentation from the start.

Negotiation

The headline number matters less than the structure. Key terms to understand:

Purchase price: The total amount, but rarely paid all at once.

Cash at close: What you actually get on day one. This is the real number.

Earnout: Additional payments tied to future performance. Risky—you're betting on execution you may not control.

Holdback: Money held in escrow for potential claims. Usually 10-20% for 12-18 months.

Non-compete: How long you can't start a competing business. Standard is 2-5 years.

I optimized for cash at close and a short earnout period. I wanted clean separation, not years of entanglement.

What I Got Right

Documentation

Every customer, every contract, every piece of equipment was documented. When buyers asked questions, I had answers. This built trust and sped up the process.

Systems

The business ran on systems, not on me. Checklists, processes, training materials—everything was documented. This made the business transferable, which increased its value.

Patience

I didn't take the first offer. Having multiple interested buyers gave me leverage. The final deal was significantly better than the initial offers.

Legal Help

I hired a lawyer experienced in M&A. The cost was worth it. They caught issues I would have missed and negotiated terms I didn't know to ask for.

What I Got Wrong

Emotional Attachment

I was more attached than I admitted. Watching someone else take over something I'd built from nothing was harder than expected. I second-guessed the decision for months.

Transition Planning

I underestimated how long the transition would take. Even after closing, I was answering questions and helping with customer relationships for longer than planned.

Tax Planning

I should have started tax planning earlier. The structure of the deal has major tax implications. A few months of advance planning could have saved significant money.

Taking Time Off

I jumped straight into the next thing. In hindsight, I should have taken a few months to decompress, reflect, and plan. Instead, I was already building what became Blackbox Holdings within weeks.

The Aftermath

Selling The Pressure King gave me:

Capital: Seed money for future ventures without needing outside investors.

Credibility: "Sold a company to PE" opens doors that "started a pressure washing business" doesn't.

Experience: The M&A process taught me how deals work, which helps when raising money or acquiring companies.

Freedom: The ability to take risks on new ideas without financial pressure.

But it also meant:

Loss of identity: For four years, I was "the pressure washing guy." That identity was gone overnight.

Watching from the sidelines: Seeing decisions made that I disagreed with, but no longer having a say.

The "what if": Wondering what the business could have become if I'd kept building.

Advice for First-Time Sellers

1. Know Your Number

Before talking to buyers, know what you need. Not what you want—what you need to walk away satisfied. This prevents emotional decision-making.

2. Get Your Books Right

Start now. Clean financials, documented processes, organized records. This is worth more than any negotiation tactic.

3. Talk to Other Founders

Find people who've sold similar businesses. Their experience is invaluable. Most are willing to share if you ask.

4. Don't Rush

Unless you're in distress, time is on your side. More buyers, better terms, cleaner process.

5. Plan for After

What are you going to do the day after closing? Have an answer. The void is real.

Looking Back

Selling The Pressure King was the right decision. The capital and experience enabled everything that came after—DuckDuckSign, Alignmint, Roladexter, Band Voyage, and the rest of the Blackbox Holdings portfolio.

But I'd be lying if I said it was easy. Selling something you built is emotional, complicated, and permanent.

If you're considering it, go in with eyes open. And feel free to reach out—I'm happy to share more.

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Your first company teaches you how to build. Selling it teaches you how business really works. Both lessons are invaluable.