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Stop Driving Your Business Backwards with Tony Cotrupe

Writer: kneetoknee
kneetoknee
Jul 22
5 min read

The Question That Opens Every Deal


Tony Cotrupe has spent thirty five years in investment banking, private equity, and business consulting. He has sat across the table from executives, factory owners, and family businesses passing from one generation to the next. When I asked him how he starts every one of those conversations, he didn't talk about spreadsheets. He said three words: how can I help.

That's the whole opening. No sales pitch stacked with jargon and slide decks. He listens until people start telling him what they need, and most of the time, he told me, they end up saying things they never planned on bringing up in that meeting.

The Rearview Mirror

Tony gave me an image I've spoken about in other settings that applied to business as well. He told me to imagine driving down the highway looking only in the rearview mirror instead of through the windshield. If the road behind you is straight, you're fine. The moment there's a turn, a dip, a tree in the road, you're in trouble.

Business owners do this constantly. They run the company today the same way they ran it five years ago, because the road behind them looked fine. Then the market shifts, a big client changes terms, or a supplier disappears, and the wreck happens fast.

Producer of Value or Consumer of Value

I asked Tony how the average guy translates high-level advisory work into his own career. He told me to ask one question constantly: am I creating value, or am I consuming it.

He said companies drift from producing value to consuming it slowly, almost without anyone noticing. Revenue can look fine while the underlying value quietly erodes. The fix starts with knowing where you actually stand, not where you assume you stand.

He defined fair market value the way a textbook would: a willing buyer, a willing seller, both with full information, neither under pressure to act. Then he told me something that stuck. In thirty five years he has never once seen a transaction that hit all three conditions cleanly. There's always an information gap. There's always some form of pressure.

Six Months of Inventory

Tony told me about a packaging company he worked with years ago. The CFO called him thrilled. They'd just landed a contract with a massive retailer he called "Stuff Mart." She thought the deal would triple the size of the company.

The contract required the company to hold six months of inventory on hand at all times, with penalties if they fell short. The margins on that account were already lower than every other customer. The company had to sink cash into product that might sit for half a year before it sold. Working capital got crushed.

That company doesn't exist anymore.

Tony was careful to say it wasn't the only factor. But the excitement over a big win blinded the team to the terms buried inside it. Growth is not the same thing as value. A bigger contract can shrink a company just as easily as it can grow one.

The Three-Part Read

Tony breaks a business down into three layers before he forms an opinion on it. First the company itself: what makes it tick, what drives its value, where the risk hides. Second the industry: who has the leverage, how much power a business has against its suppliers and its customers, how easily a competitor could open up across the street tomorrow and start eating the same lunch.

Third, the economy sitting over the top of both. He used equipment manufacturers as the example. When interest rates climb, customers stop financing new machinery. It has nothing to do with the quality of the equipment or the strength of the sales team. It's the cost of money working against them, and no amount of hustle inside the building changes that.

I kept thinking about how rarely any of us zoom out that far. Most of the time we're heads-down on the company layer, maybe the industry layer if we're paying attention. The economy layer feels too big to touch, so we ignore it and wonder later why a good year turned sideways.

The Line at My Door

Tony's story about the packaging company reminded me of my own. Years ago I took over running a company where the previous owners had trained everyone to ask before doing anything. For weeks I had a line of people outside my office door, waiting to ask me basic questions.

I finally told my team: if you have a question, bring me three solutions first, and then we'll talk about which one makes sense. Within a few months, the line disappeared. People started solving problems instead of forwarding them to me.

Tony brought up something Steve Jobs is credited with saying: hire smart people and let them do their jobs. That's what building real value inside a company looks like. Not one guy holding every decision. A team that can move without him.

The One Question We Ask Every Guest

At the end of every KneeToKnee episode, I ask the guest the same question: what's one thing our listeners can do today to build deeper connections with those around them.

Tony's answer was simple. Reach out to someone you haven't talked to in a long time. A high school friend. An old colleague. Someone who shaped who you are, even if you haven't spoken in years.

That question landed harder than usual for me, because earlier that same day I'd gotten on the phone with someone I hadn't talked to in a long time. Her husband had been my boss years ago. I found out during that call that he'd passed away. We spent a few minutes trading old stories, and I felt grateful we still had a way to reach each other.

Tony said it brings dividends in ways you can't imagine. I believe him.

What I Took From This One

This conversation started as a business episode and ended as a relationship episode, which tells you how tightly the two are actually connected. The way Tony builds trust with a client is the same way any of us build trust with anyone: show up, ask how you can help, and listen to the answer.

Check your own business, your career, your relationships, against the rearview mirror test. If the road ahead looks exactly like the road behind, you're probably fine. If something has shifted, don't wait for the wreck to notice it.

And call that person you've been meaning to call. Get the book Inspired by the podcast: Connection the Ultimate Force Multiplier: https://www.amazon.com/dp/B0H44R97ZX


KneeToKnee is where men build the crew that rebuilds them. Fitness, fatherhood, career, marriage. Men perform better when connected to other men. Some links are affiliate links.

 
 
 

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