By Ryan Fitzgerald, Founder of Timberline Exit Partners
July 1, 2025
Before I ever advised anyone on selling their business, I was in the exact same position you might be in today. I’ve been the one staring at the ceiling at 2 AM, wondering if it was the right time to sell. I’ve felt the anxiety of keeping the biggest decision of my life a secret from the employees who felt like family. And I’ve navigated the emotional rollercoaster of seeing my life’s work translated into a number on a contract.
Selling a business isn’t just a financial transaction; it’s a profound life event. My experiences as an owner of a playground construction company, a bookstore, and a thrift store taught me invaluable lessons that no textbook or seminar ever could. Now, as a business broker, these lessons are the foundation of how I guide my clients.
If you are a business owner thinking about your future, here are the three most important things I learned from selling my own businesses.
1. Your Business is Worth What a Buyer Will Pay, Not What a Spreadsheet Says.
When I first thought about selling, I did what most owners do: I ran the numbers. I looked at my assets, my profits, and what I felt the business was worth. But the hard truth is that a business’s value isn’t a calculation; it’s a conviction. A buyer has to be convinced that your business is worth the price.
My biggest lesson was that clean, verifiable financials are the language of conviction. A buyer (and more importantly, their lender) won’t be impressed by a story of “how much the business really makes.” They need to see it, clearly and professionally, in your financial statements.
This is where my background in the tax and financial services industry became my secret weapon. I learned to “recast” my financials long before I ever thought of selling—adding back my personal car expenses, discretionary travel, and other perks to show the true, underlying profitability, or Seller’s Discretionary Earnings (SDE). When a buyer’s accountant came asking questions, the answers were already there, organized and defensible.
The takeaway for you: Start cleaning up your books today, even if you’re years away from selling. Separate personal and business expenses with religious discipline. When the time comes, a buyer won’t just be buying your business; they’ll be buying your credibility.
2. Confidentiality is Not Just a Buzzword; It’s Your Most Valuable Asset.
The fear of a premature leak is real. What if my employees find out and start looking for other jobs? What if my customers hear a rumor and lose confidence? What if my biggest competitor finds out and uses it against me?
I lived with that low-grade anxiety. Every conversation with my wife felt like a state secret. This taught me that the process itself must be designed to protect confidentiality.
A professional broker’s most important job is to be the buffer. They are the ones who can market your business anonymously, field all the initial inquiries, and force every single interested party to sign a strict Non-Disclosure Agreement (NDA) before they even learn the name of your company. They vet buyers to separate the serious contenders from the “tire-kickers,” ensuring that only a handful of highly qualified, confidential parties ever get access to your sensitive information.
The takeaway for you: Do not try to sell your business on your own. The risk of a breach of confidentiality is too high. A single slip-up can damage morale and your company’s value. A controlled, professional process is the only way to protect your legacy.
3. You Are Not Selling a Business; You Are Selling a Future.
When I sold my first company, I was obsessed with its history. I wanted to tell the buyer about every success, every challenge overcome, every long night I put in. While that story is important, I quickly learned that buyers are not buying your past; they are buying their future.
A buyer’s most important question is, “How will this business make money for me, without you?” Your job is to provide a clear and compelling answer.
This means two things:
- Have a Growth Story: What are the untapped opportunities? Is there a new service line to launch? A new market to enter? An operational efficiency to be gained? You need to present the business not as a finished masterpiece, but as a fantastic platform for future success.
- Make Yourself Replaceable: The more a business depends on you personally, the less it’s worth. I learned to document my processes, delegate responsibilities, and build a team that could function without my daily intervention. This de-risks the business for a buyer and makes them confident they can successfully take the reins.
The takeaway for you: Spend the years leading up to your sale thinking like a buyer. Document your systems, empower your team, and identify 2-3 clear, actionable growth opportunities. When you sell, you’re not just handing over the keys; you’re handing over a roadmap to future prosperity.
Selling a business is a journey. It’s complex, emotional, and one of the most important things you will ever do. Having an advisor who has walked that path themselves can make all the difference.
If you’re starting to think about your own exit, let’s have a confidential conversation. I’ve been there, and I can help.