Reckless or Right?

Words: Damian Lang

When Everyone Says Quit, But Your Gut Says Push

I have been in business long enough to know it humbles even the most confident entrepreneur. It can test your nerves and make you question every decision, especially when you’re surrounded by mentors and advisors who all share the same opinion, but your instincts tell you they're wrong. I found myself in that position not long ago.

Five years ago, one of my companies was on the brink of collapse with debt mounting at an alarming rate. I spent many nights staring at the ceiling, trying to figure out how we could turn it around. I had valued members of my organization, outside advisors, and financial professionals, all of whom told me it was time to shut it down. And to be fair, the numbers supported them. We had made mistakes, some of them expensive, and every forecast pointed toward doom.

With all the evidence lining up on one side, logic said to listen. But in a decision like that, the loudest voice should belong to the person with the most to lose. On paper, it appeared they were right. However, what they couldn't see was what I knew for a fact: if this business turned around, it would not be a slow, incremental recovery. It would flip like a switch.

I’m sure some believed I was in denial, but my position wasn't based on guesswork. I listened to audiobooks and spent hundreds of hours studying companies in similar situations. Some had survived. Some died.

During my research, I came across Professor Tom Eisenmann’s Harvard Business School study, “Why Start-ups Fail.” One of the key takeaways was that many collapsing businesses aren't actually doomed; they are suffering from a “false start.” On paper, they look broken because they are bleeding cash, but structurally, they’re just unfinished.

That was exactly the state of my company. It wasn’t a dead enterprise; it was a business that had not yet found its footing. That insight allowed me to see light at the end of the tunnel.

I know how that sounds. Every stubborn entrepreneur who has ever refused to walk away probably says the same thing. The challenge is knowing whether that light is a real opportunity or an oncoming train. But I wasn't operating on blind optimism; I now understood what our data was actually saying. The underlying market demand was proven, which meant the company was worth saving. There were still significant operational problems that needed to be addressed, but we had the capacity to solve them. However, turning things around requires capital, and with our current numbers, no outside investor would fund the fix.

So, I decided to invest more than $9 million of my own cash in the company, with no guarantee I would ever see it again. Outwardly, that probably looked reckless. From my perspective, it was a calculated risk.

I believed I would get every dollar back many times over, but before making that commitment, I forced myself to answer two questions honestly. First, if it succeeds, will the upside justify the risk? I had to be certain that the potential gains would be massive enough to bury the expensive mistakes we had already made. Second, if this fails completely, can I survive it? While it would be a significant financial hit, I knew it wouldn’t destroy my family or my other businesses. That was important.

In my experience, too many business owners in similar situations make mistakes because they haven't addressed both sides of that equation. They either risk money that will ruin them or walk away because they haven’t clearly calculated the true upside against the downside. Recognizing those boundaries is what changes the outcome.

Because I knew I could survive the worst-case scenario and that the reward would vindicate the struggle, taking the risk wasn't reckless. It was a deliberate, clear-headed choice. Yet living with my decision was a different story. Conviction doesn’t insulate you from the day-to-day pressure. There were still nights when I wondered if everyone else had been right. Every new obstacle brought those advisor warnings roaring back into my head: shut it down, cut your losses. You realize how brutally lonely it is to stand your ground when every other smart person in the room is turning toward the exit.

But I kept coming back to the same certainty. We were going to hit that turning point, and when we did, everything would change instantly. On one side were heavy losses, and on the other side were tremendous gains. My job was simply to keep the company alive long enough to reach that turning point. I truly believed the eventual turnaround would completely offset the missteps we made along the way. That certainty was my anchor.

If 40-plus years of building businesses have taught me anything, it’s that the person most deeply invested in the outcome is usually the only one willing to keep believing. Therefore, they have earned the ultimate voice in deciding whether to push forward or pull the plug. Belief alone, however, is never enough to pull off a turnaround. In this case, the president and CFO provided the fierce leadership and strict financial discipline, while our team dug in to solve the relentless daily problems that came with working under immense pressure. It was the collective effort of a group that refused to quit.

Today, the company I almost walked away from five years ago has been sold. The staggering return vindicated every dollar I risked. The switch flipped exactly as I believed it would. On this side of the sale, I can tell you the most important investment was not just the money. It was trusting my instincts and staying in the fight long enough for the business to become the success I always believed it could be.

Sometimes the hardest part is recognizing the difference between a business that is broken and one that has not reached the other side of its problems. That distinction can cost millions to learn, and it can be equally devastating if you walk away too soon.

Should you ever find yourself staring at a company that everyone says is finished, I am not suggesting that you ignore advisors or blindly follow your gut. As a leader, once you’ve sought counsel and studied the numbers, the final decision is yours. If you’re confident the gains will cover the mistakes already made and you can survive a loss if you’re wrong, then write the check and push forward.
___

Damian Lang is CEO of Lang Masonry Contractors, Wolf Creek Construction, Buckeye Construction and Restoration, 3 Promise Labor Services, FlexCrew, and EZG Manufacturing. To view the products and equipment his companies created to make job sites safer and more efficient, visit his website at ezgmfg.com. To receive his free e-newsletters or to speak with Damian about his management systems or products, email dlang@watertownenterprises.com or call 740-749-3512.

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