Pivotal Moments That Changed How Founders Run Their Businesses

"As a founder, what’s one pivotal moment or hard-earned lesson that fundamentally changed how you run your business—and how did it shape your leadership or company culture moving forward?

Here is what 7 thought leaders had to say.

Transparency Turned a Setback into a Stronger Company Culture

One pivotal moment for me came during our first major service setback at 3G Pool Services. A client’s pool project faced unexpected delays, and instead of owning up immediately, I tried to fix everything quietly behind the scenes. That decision backfired, it taught me that transparency is not just good ethics, it’s good business.

Since then, I’ve built a culture around open communication, where my team feels comfortable admitting mistakes early and finding solutions together. It completely changed how I lead, I stopped trying to be the person with all the answers and became the person who helps everyone find better ones. That shift turned our crew into a tighter, more accountable team, and our clients can feel that honesty in every interaction.

Ross Wilbur, Owner, 3G Pool Services

Systems Replace Self: How I Tripled My Company's Growth

My third year at KhrisDigital was a turning point. I had already created a number of successful affiliate sites, but all components of the business were contingent on me. Unless I ceased writing, publishing, or outreach, the revenue decreased in a few weeks. Those forces made me redefine what growth was.

I have re-designed my whole content system in such a way that it is able to operate without me being around all the time. I also reported transparent working out procedures, instructed authors to concentrate on the purpose and search intent, and presented a content calendar combining the long-term growth of the SEO strategy with the affiliate push. In six months, the production increased three times, and revenue increased over 60 percent.

The change also transformed my outlook towards leadership. I no longer thought of business as part of me and started considering it a separate machine that could be operated by other people without any hesitation. This has redefined our culture toward marking out our culture in terms of clarity, ownership and execution rather than perfection. All the contributors are aware of what success is without me telling them what I consider the definition of success.

Khris Steven, Owner & Marketer, KhrisDigital

Impact Over Perfection: The Beyond Chutney Revolution

There was a time when I pushed too hard for perfection. I wanted every campaign, every post, every tiny detail to look flawless. It reached a point where progress slowed because we were constantly polishing instead of launching. One day, after spending hours tweaking a single headline, I realized I was missing the bigger picture — impact over perfection.

That moment changed how I run Beyond Chutney. I started valuing action, creativity, and learning from real results instead of obsessing over spotless execution. It also reshaped our culture. Now, my team knows it's okay to experiment, make mistakes, and adapt. We celebrate progress, not just perfection. It made the entire process feel more human — and honestly, a lot more fun.

Bernhard Schaus, Online Marketer, Beyond Chutney

Trust Your Team: How Client Loss Transformed Leadership

I lost one of our most important clients a few years ago because I was trying to handle everything on my own. I believed that being a good leader entailed making all of the decisions, reviewing every project twice, and staying up late to make corrections myself. That client's departure really got to me. I recall wondering where I'd gone wrong while sitting in the office long after everyone had left and the only sound was the air conditioner humming.

That experience made me face myself and understand that trust is a duty rather than a risk. I began to involve the team more, solicit their feedback, and give them more responsibility for their work. The transformation was astounding. In all honesty, people felt happier, more creative, and more invested. It taught me that being a leader is about knowing when to let others take the wheel, not about gripping it tighter.

Eugene Musienko, CEO, Merehead

Delegation Means Decisions, Not Just Tasks

One moment that completely changed how I lead was realizing that delegation is not about giving tasks; it is about trusting people with decisions. In the early days, I felt I had to be involved in every detail to keep quality high. That belief worked for a while, but it soon became a trap. During one intense client project, my need to control everything slowed the team down and caused frustration. I was unintentionally blocking creativity by not giving space to others.

That experience forced me to rethink leadership. I learned that true delegation means giving ownership, not oversight. Once I started empowering team members to take responsibility and make choices, everything changed. Productivity improved, but more importantly, people became more confident and engaged. They no longer waited for instructions; they built solutions and brought new ideas to the table.

This shift transformed our company culture. Instead of one person managing every step, Spectup evolved into a space where everyone feels trusted and accountable. It also gave me the freedom to focus on long-term vision and strategy while knowing that execution was in capable hands.

Looking back, that lesson taught me that leadership grows when control is shared. Trusting your team is not a risk; it is an investment that multiplies the impact of your business.

Niclas Schlopsna, Managing Consultant and CEO, spectup

The Moment That Redefined My Leadership

One pivotal moment that changed everything for me was when we lost a major client early on because we overpromised and under-communicated. It was a painful but necessary wake-up call. I realized that trust isn’t built through perfection but through consistency and transparency. Since then, I’ve made open communication a cornerstone of our culture whether it’s with clients or within our team.

We now share wins and setbacks in real time, so no one feels left in the dark. That shift didn’t just make us stronger as a business; it made us more human. It taught me that leadership isn’t about having all the answers — it’s about creating an environment where people feel safe enough to find them together.

Brian Greenberg, Founder, Insurancy

Steer the Ship, Stop Rowing It

There was a point where I was everywhere. I added myself to every meeting, and I try to do work that my people should have been doing. Then one of my team members joked that we'd move faster if I'd stop assisting. So I backed off. I let my people do what I hired them to do. The result? They crushed it as they should have. These days, my job's a lot more about steering the ship than rowing it. Good leadership is also about great self-preservation.

Cody Jensen, CEO & Founder, Searchbloom