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  • Financial Record Cleanup: What Buyers Actually Look for in Diligence

    I still remember the first time I sold a business. Well, “business” is a generous word. It was more like a side hustle with delusions of grandeur and a shoebox full of receipts. The buyer’s accountant took one look at my “records” and laughed. Not a polite chuckle either. A full belly laugh. I learned something that day: your financial house needs to be in order long before anyone shows up with a checkbook.

    These days I’ve been on both sides of the table, and let me tell you, buyers are nosy. Not in a creepy way. In a “show me every penny since 2019” kind of way. Here’s what they actually dig into during diligence, and how to get your books ready before the spotlight hits.

    They Want Clean Books, Not Perfect Ones

    Nobody expects a small business to have pristine, audit-ready financials. What buyers hate is messy books. There’s a difference. Missing invoices and mystery expenses? Red flags. A QuickBooks file that reconciles every month, even with a few handwritten notes in the margins? Totally fine.

    Here’s what to tidy up first:

    1. Reconcile every bank and credit card account monthly. All of them. Yes, even the one you use for “business lunches” that are really just you and your dog.

    2. Match every expense to a receipt or invoice. If you can’t find one, document why.

    3. Separate personal and business spending. This one hurts, I know. But commingled funds make buyers run for the hills.

    Revenue Recognition: The Silent Deal Killer

    Buyers don’t just want to see money coming in. They want to see it coming in predictably. If your revenue spikes every March because of one whale client, say so. Hiding lumpy revenue is worse than having it.

    Be ready to explain:

    • Your top five customers and what percentage of revenue each represents

    • Any contracts with auto-renewal or cancellation clauses

    • Seasonal patterns and how you plan around them

    I once watched a deal nearly collapse because the seller “forgot” that 40 percent of revenue came from a single client. The buyer found out. They always find out.

    Tax Filings and the Dreaded Notice Letter

    Buyers pull tax transcripts. Every return, every schedule, every amendment. If you’ve got an open IRS notice sitting in a drawer, deal with it now. Not next quarter. Now.

    A few things to have ready:

    • Filed returns for the last three to five years

    • Proof of payment for any payroll taxes

    • Documentation for any penalties or late fees you’ve paid

    Old tax problems don’t necessarily kill a sale, but surprises do. Disclose early and you keep the trust.

    The Paper Trail Buyers Trust Most

    Here’s the thing about diligence. It’s not really about numbers. It’s about confidence. Buyers want to feel like nothing will jump out of the closet after closing. Clean records build that confidence. Messy ones erode it, no matter how profitable you are.

    So before you list your business, do a dry run. Pretend you’re the buyer. Ask yourself the uncomfortable questions. Then fix what you find. Your future self, and your buyer’s accountant, will thank you.

  • Improving Margin Direction to Defend Your Valuation Multiple

    Here’s something I’ve learned from decades in the gym and in business: nobody respects a physique that only looks good under perfect lighting. Same goes for your company’s margins. Investors can spot a pump fake from a mile away.

    Let me share a story.

    Back in my competitive days, I watched plenty of young bodybuilders chase size at all costs. They’d add pounds of mass, sure, but it was sloppy weight. No definition. No foundation. The judges saw right through it. The guys who won? They built lean muscle year after year and kept their conditioning dialed in.

    Your valuation multiple works the same way. Revenue growth gets attention. Margin direction earns trust.

    Why Margin Direction Matters More Than a Single Good Quarter

    A lot of founders treat margin like a vanity metric. They spike it before a raise, then let it slide. Investors remember that pattern.

    Think about what a multiple really represents. It’s a bet on your future. When your margins are trending up, you’re telling the market your operations are getting sharper. You’re proving the business can scale without the costs scaling right alongside it.

    Here’s what buyers and investors actually want to see:

    1. Consistent margin expansion over multiple periods

    2. A clear story behind what’s driving that expansion

    3. Evidence that the improvement is repeatable, not a one-time trick

    Chasing a single impressive quarter is like crash dieting before a show. You might look decent for a weekend. You won’t hold it.

    Three Levers That Actually Move Margin Direction

    I keep things simple. In training and in finance, the fundamentals win.

    Pricing discipline. Most companies leave money on the table because they’re scared to charge what they’re worth. Small, regular price adjustments compound quietly. Test them. Measure them. Keep what works.

    Cost structure honesty. Go through your expenses like you’re auditing a training program. What’s actually building the business? What’s just comfortable habit? Cut the fluff and protect the investments that drive real output.

    Operational leverage. This is the big one. Map out which costs stay flat as revenue grows. When those fixed costs shrink as a percentage of sales, your margins expand on autopilot. That story sells itself.

    The Discipline Nobody Wants to Hear About

    Margin improvement is boring work. It’s tracking unit economics on a Tuesday night instead of chasing the shiny new partnership. It’s saying no to low margin deals that make the top line look pretty.

    Sound familiar? It’s the same reason most people never build a stage ready physique. The daily grind isn’t glamorous. It just works.

    Here’s a quick gut check I run before every planning cycle:

    • Are my gross margins trending up over the last four to eight quarters

    • Can I explain the driver behind each improvement in one sentence

    • Would these gains survive a downturn or a price war

    If any answer is shaky, that’s my training priority for the next quarter.

    Defending Your Multiple Starts With the Trend Line

    Investors don’t pay premiums for promises. They pay for proof. A steady margin trend tells them your team knows how to run the business tighter every single year. That narrative protects your multiple when markets get nervous and gives you room to negotiate when they don’t.

    So before your next board meeting or pitch, pull up the trend line. If it’s flat, fix it. If it’s rising, tell that story loud and clear.

    Build lean. Stay consistent. Let the numbers do the talking. That’s how you defend a valuation multiple that actually holds up.

  • Fixing Customer Concentration: A Seller’s Guide to Protecting Your Multiple

    I learned a brutal lesson about customer concentration the hard way. Years ago I walked into a business that looked like a dream on paper. Nice revenue, clean books, owner ready to retire. Then I cracked open the customer list and almost choked on my protein shake. One client accounted for 61% of sales. Sixty one. That deal fell apart faster than my first attempt at a cut, and honestly it deserved to.

    Since then I have helped dozens of owners wrestle this problem to the ground. Here is the playbook.

    Why Buyers Run From Customer Concentration

    Picture handing your life savings to someone who says one phone call could erase a third of their income. That is what a buyer sees when one customer dominates the revenue sheet. Deals get repriced, delayed, or killed outright. Multiples shrink. Sometimes the buyer wants a chunk of the price held in escrow for years. Nobody trains for this moment. You just wake up one day and realize your biggest client owns your exit.

    First Step: Measure the Damage Honestly

    Pull three years of revenue by customer. List every account over 5%. Then answer one question for each big one:

    • Do they have a contract and when does it expire?

    • Could they leave tomorrow with zero penalty?

    • Are they paying market rates or sweetheart rates?

    If the answer to the middle question is yes, you have work to do. No shame in it. Most owners built their business on one big break. I get it.

    The Fix: Grow Around the Problem

    Here is the part people miss. You do not necessarily need to fire your whale. You need to make the whale smaller as a percentage of a bigger pond.

    1. Add new logos. Even small ones. Ten clients at 2% each beats one client at 20%.

    2. Raise your prices on the dominant account if the market allows it. Better margins make the relationship less fragile.

    3. Convert informal arrangements into written contracts with notice periods.

    Contract Terms That Calm Buyers Down

    When I sit across from a nervous buyer, these terms do the heavy lifting:

    • Multi year agreements with clear renewal language

    • Reasonable termination notice, 90 days or more

    • Defined pricing so there are no surprise renegotiations

    • Documentation showing the relationship survived at least one price increase

    No contract is bulletproof. A signed deal signals commitment and that matters at the negotiating table.

    Diversify Beyond the Customer List

    A buyer’s fear is really about dependency. Show them the business does not live or die on one relationship. How?

    • Document your sales process so revenue is not trapped in the owner’s head

    • Build a referral pipeline that feeds new accounts every quarter

    • Keep at least one growth channel running that does not touch the big client

    Timing Matters More Than You Think

    One more thing from the gym of hard knocks. Start this work two to three years before you plan to sell. Buyers want to see a trend line, not a panic move six months before listing. I have watched sellers scramble at the last minute and pay for it in the multiple. Do not be that person.

    The Bottom Line on Protecting Your Multiple

    Customer concentration is fixable. It just takes time, honest numbers, and a plan you actually follow. Do the boring work now and your exit gets smoother and richer. Trust me on this one. Your future buyer is already nervous. Give them less to worry about.

    Quick recap:

    1. Measure revenue by customer across three years

    2. Grow new accounts until the big one shrinks by percentage

    3. Lock in contracts and notice periods

    4. Start at least two years before selling

    That is the whole game. Go lift some weights and get to work.