Shalom Lamm on Learning the Hard Way: How a Costly Mistake Became a Turning Point in Business

Every business has its highlight reel—milestones hit, deals closed, revenue growth. But behind every shiny success story is a graveyard of hard lessons, tough calls, and decisions that didn’t go as planned.

Entrepreneur Shalom Lamm is no stranger to these kinds of moments. Over the course of building and advising multiple ventures, Lamm has seen firsthand how even experienced business leaders can make missteps—sometimes big ones. But what separates thriving businesses from those that crumble is how leaders respond in the aftermath.

“You don’t learn much from your wins,” says Lamm. “It’s the decisions that go sideways—the ones that hurt—that teach you what really matters.”

In this post, we unpack the worst business decision Lamm ever made, what it cost, and why he credits that experience with making him a stronger, more grounded entrepreneur today.

 

The Decision That Seemed Right (Until It Wasn’t)

At the time, it felt like the smart move: expand fast to capture market share. Shalom Lamm and his team were leading a growing real estate venture and had built early momentum in several markets. When an opportunity arose to enter a new, highly competitive metro area, it looked like the next logical step.

“On paper, it made sense,” Lamm recalls. “We had capital, a replicable model, and confidence. The numbers looked tight but doable. We thought, if we don’t go now, someone else will.”

With speed in mind, the team greenlit a major investment: a multi-property acquisition that would double their holdings in just a few months. They stretched their resources, leaned heavily on debt, and put much of their team’s focus into launching the new market.

At first, things went smoothly. But cracks began to show quickly.

 

The Fallout: What Went Wrong

Despite promising analytics and thorough prep, the new market underperformed. Local regulations were more complex than anticipated. Leasing took longer. Renovation timelines slipped. And worse, the team’s focus on the expansion left core markets neglected.

“We realized too late that we’d overextended,” Lamm admits. “We tried to scale something that wasn’t truly ready to scale—and we lost sight of our foundation in the process.”

The financial strain was intense. Cash flow slowed. Morale dipped. At one point, Lamm says he questioned whether the company could survive at all.

 

Lessons From the Edge

It took over a year to unwind the damage. The team had to divest properties, renegotiate financing, and rebuild operational stability. But through it all, Lamm and his leadership team learned lessons that have reshaped how they run businesses today.

1. Don’t Confuse Momentum With Readiness

Just because something is working doesn’t mean it’s ready to scale. The team mistook early wins for systematized success.

“Momentum can mask weakness,” Lamm says. “We hadn’t pressure-tested our systems. We thought we had a machine when we only had a strong streak.”

Now, his team uses a simple rule: no expansion unless the current system is boringly stable.

 

2. Always Leave Breathing Room

In the rush to grow, the business stretched itself too thin—financially and operationally. They chased aggressive targets with no margin for error.

“It wasn’t the expansion that broke us—it was the lack of buffer,” Lamm explains. “One delay, one misstep, and everything started to unravel.”

Today, he budgets with built-in cushions and ensures every major initiative has a contingency plan.

 

3. Growth Without Culture Is Fragile

One of the biggest blind spots was cultural. The new market never fully absorbed the company’s values, expectations, or standards. With leadership split between regions, cohesion suffered.

“You can’t outsource culture,” Lamm says. “It’s not something you install—it’s something you cultivate. And we weren’t present enough to do that.”

Now, culture-building is non-negotiable during any expansion. The company invests time and leadership presence in every new location before launching at scale.

 

4. Failure Is the Best Filter for Leadership

The pressure exposed gaps in leadership—not just among managers, but at the executive level. Some team members stepped up. Others froze.

“We found out who we were in the storm,” says Lamm. “That clarity was painful—but priceless.”

Today, the company prioritizes leadership development far more seriously. Soft skills, emotional intelligence, and crisis management are now part of the core training process.

 

The Rebuild: Stronger, Leaner, Wiser

It wasn’t easy, but the business rebounded. The core markets recovered. New frameworks were implemented. Expansion strategies became far more disciplined.

More importantly, Lamm says, the experience reshaped the team’s mindset.

“We’re still ambitious—but it’s a different kind of ambition now,” he reflects. “Less ego, more intention. Less speed, more precision. We’re building something that lasts, not just something that impresses.”

 

Advice for Founders Facing Regret

Shalom Lamm is quick to acknowledge that business mistakes are inevitable. But the difference lies in how leaders handle them.

“The worst decision you make isn’t what breaks you,” he says. “It’s how you respond after it.”

For founders navigating regret or fallout from a poor choice, Lamm offers this guidance:

• Own it early – “The longer you delay accountability, the deeper the damage.”
• Fix the root, not just the result – “Patchwork never lasts. Get to the system failure beneath the mistake.”
• Be transparent with your team – “Trust builds when leaders are honest—even about failure.”
• Let it shape you, not define you – “The goal isn’t to avoid mistakes. It’s to let them sharpen your instincts.”

Final Thoughts: Failure Isn’t the End—It’s the Turning Point

Every entrepreneur dreams of making the right call every time. But reality is messier. Even the sharpest leaders—like Shalom Lamm—make decisions that hurt. What matters most isn’t avoiding those moments—it’s how you recover, rebuild, and refuse to let them own your story.

“Looking back, that decision almost broke us,” Lamm says. “But it also built the version of us that could thrive long-term. And that’s a trade I’d make again.”