By Bob Louthan | CEO, VeteranCrowd
Two Closings
I have worked directly with privately held businesses since 1994. In 2008, I closed two deals that changed how I do business.
The first client was not a veteran. The work was done, the agreement signed, the company sold. Then, at the closing table, he decided our fee was negotiable. In my business, we call that a “fee-ectomy.”
The second client was Warren Jenkins, a former Army noncommissioned officer and a fellow man of faith. When his company sold, he never pulled out our contract. He called and asked, “How much do we owe you?” I told him. He paid it.
One man honored his word. The other went looking for a way out of it. That experience was not a judgment on every civilian in business. But it reminded me how much I valued the trust I found among fellow veterans.
From 2008 forward, I decided to work only with veteran-led companies.
The Speed of Trust
If you’ve served, you already know why. If you haven’t, let me show you.
Put two veterans who have never met in the same room. Within five minutes, one discovers the other was a Marine. Correction: is a Marine. Then the insults start. Somebody brings up crayons. Somebody says “Chair Force.”
Warren never missed a chance to remind me that NCOs run the Army and officers just sign for it.
To an outsider, it sounds like the start of a fight. It’s the opposite. It’s a password. It’s our love language. It says, “I know where you’ve been. I know what you gave up. I know you didn’t quit when it was cold and wet and miserable, because neither did I.”
That’s the speed of trust. Shared experience can cut through months of sizing each other up. Two people shake hands, and the handshake means something. Of course, a shared uniform does not guarantee character. What matters is how a person lives up to that trust.
Simon Sinek has described how Navy SEALs weigh performance against trust: a high performer nobody trusts can be a worse teammate than a solid performer everyone relies on. I learned something similar at the deal table. Trust matters more than pedigree, a fancy degree, or raw talent alone.
That’s why I say veteran-led, not just veteran-owned. Ownership is a designation. Leadership is what you see when you walk the floor. It’s the morning brief and the after-action review. It’s the five-paragraph order and the OODA loop that turns faster than the competition’s. It’s leaders who train their people, then trust them with real authority. That’s how purpose, service, and ethics show up in daily work.
Same Mission, New Methods
My timing was terrible. In 2008, the floor fell out of the economy. Mergers and acquisitions trail the market, so once our deals in progress closed, the phone went quiet. I never doubted the decision.
I’ve spent the 18 years since in the veteran-led business world. I’ve interviewed veteran founders on the Mission Oriented podcast. I’ve sat in folding chairs at Bunker Labs and Patriot Boot Camp and stood at the back of veteran service organization conferences. I’ve hosted veteran business events where you could feel the room light up as people discovered who had served where.
Here’s what I learned in those rooms: veterans often want to do business with other veterans. That’s a gift. It can also get us into trouble.
Character gets you started. It doesn’t teach you to read a balance sheet, build a sales pipeline, or negotiate a term sheet. The mission may still be service, but the methods are different. Either learn those skills or recruit people who already have them.
Along the way, I watched good veterans struggle. Three lessons kept coming back, and I learned every one of them the hard way.
Lesson One: Make the Ask
The first lesson sounds simple. Ask.
Think about how you were trained. You don’t talk about yourself. You give credit to the team. If you have to tell people how good you are, you probably aren’t. That humility is one of the best things about us.
Now picture a veteran founder across the table from an investor. Fifteen minutes in, she has talked about her team, her customers, and her market. She hasn’t once explained why she is the person to lead this company. When it’s time to name the number, she looks down at her notes and says it quietly, almost like an apology.
Early-stage investors are not just evaluating a spreadsheet. They are asking: Do I trust this person? Can this team execute? Do I want to work with them when the plan falls apart? The numbers matter, but so does the leader sitting across the table.
If you won’t make the case for yourself, nobody in that room will make it for you. Making the ask isn’t bragging. It’s briefing the mission. You’ve done it before, standing in front of a commander. Do it again.
Lesson Two: Don’t Ruin a Good Reputation
The second lesson: veteran-owned may open the door. Don’t ruin the opportunity.
That label can get you into rooms. A buyer who served sees it on your card and takes the meeting. An investor who wore the uniform returns your call. That goodwill is real. Be grateful for it.
But once you walk through that door, nobody buys a label. They buy value, a fair price, and the confidence that you’ll show up when you said you would.
A reputation takes years to build and minutes to ruin. Miss a delivery date. Cut a corner. Make a promise you can’t keep. The door that swung open so easily can slam shut.
The label might get you the first meeting. Being veteran-led means doing what you said you would do when you said you would do it. That is what earns the second order.
Lesson Three: DROOM
The third lesson comes with an acronym, because of course it does. DROOM: Don’t Run Out of Money.
I’ve been on both sides of this one, first as a banker and now as a founder.
Veterans can treat capital like a requisition: figure out the minimum, fill out the paperwork, make it last. Asking for more can feel greedy. But investment capital isn’t a supply request. It’s a responsibility to the people who trusted you with their money. Those investors are weighing your risks and returns against every other place they could put it.
Growth can choke a business. Every new order can mean more inventory, more payroll, and more money owed to you that hasn’t arrived yet. Your working capital needs can grow faster than your cash comes in.
Picture Patton’s Third Army in late August 1944. After the Allied breakout from Normandy, his forces raced across France. By early September, the advance had stalled for lack of fuel. The enemy had not stopped every tank. The supply lines simply could not keep up.
I know that feeling. In our own company, we never seemed to have enough time or money to do everything. We had to ration both. More than once, we came close. Very close. The kind of close that keeps you staring at the ceiling at 3 a.m.
So plan for more cash than your most optimistic forecast requires. Secure capital before you desperately need it. And watch your runway the way you used to watch fuel and ammunition.
What Investors Really Look For
Which brings me to the question veteran founders ask me most: What do bankers and investors really look for?
My answer is one word: perseverance.
Experienced investors know the plan will change on first contact. They want to see whether you’ll still be standing when it does, still adapting and still pushing toward the objective when you’re tired, short on supplies, and nobody is coming to help. They also need to believe you have the judgment and resources to make that persistence count.
Veterans know that ground. We’ve been there. But perseverance needs fuel. You need both the will to keep going and the money to do it.
The Handshake
Warren and I still talk today, nearly two decades after that phone call. We still give each other a hard time. And I would still do a deal with him on a handshake.
That’s the whole thing, really. Two people who served, who trust each other, doing business the way it ought to be done.
So if you’re a veteran thinking about starting or growing a business, here’s what I’d tell you: Bring your character with you. Learn the business. Make the ask. Protect your name.
And whatever you do, don’t run out of gas.
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As the Voice of the Veteran Community, The Havok Journal seeks to publish a variety of perspectives on a number of sensitive subjects. Unless specifically noted otherwise, nothing we publish is an official point of view of The Havok Journal or any part of the U.S. government.
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