10 Lessons From 10 Years — How to Build a Lasting Business

It’s a strange moment to write about what makes companies last, with global uncertainty at historically high levels and leaders being asked to make huge bets on AI, talent and where the world is going. At the same time, employees are nine times more likely to be engaged when they believe their company has a secure future. 

Consider those two findings for a second: The defining tension of building a company today is that the ground is shakier than ever, and the people you lead need more steadiness than ever. That tension is exactly what the last decade of building Ninety has been about. 

I spent years as an investor and board member watching capable teams struggle with the same problems: lack of shared vision, cultures without purpose, priorities that didn’t translate into coordinated work and leaders who didn’t have a connected view of how their company was running. I founded Ninety to build the business operating system I kept wishing those companies had. In doing so, I started living these problems from the inside. 

On our 10th anniversary, here are 10 lessons I learned the hard way.

1. Vision and culture come first

That’s what attracts and retains great people. I keep coming back to the old Drucker line that culture eats strategy for breakfast. For me, that is how enduring organizations work. Ninety was never trying to be the cheapest tool or the one with the most features. It was built around service, stewardship, high trust and doing the right thing. That culture is what let us keep good people through hard years.

2. Lead with customer experience

Every company has to choose a core value proposition, whether it’s lowest cost, constant innovation, exclusivity or service. We picked service, and we’ve been tested on it. When COVID hit and revenue dried up for entire client sectors overnight, the short-term move would’ve been to nickel-and-dime people to protect our own numbers. We chose the opposite. We gave customers grace when they were struggling, because in the long run, genuine care builds trust that no marketing budget can buy.

3. Build resilience, not perfect plans

No plan survives the first real hit; what matters is whether the company can absorb it and keep functioning. That is resilience, and it comes from where you spend your energy. Energy is finite. Spend it fighting things you can’t control, like market swings, regulatory shifts or a competitor’s moves, and you’ll have nothing left for what you can control, like aligning your team, executing and managing cash.

4. Don’t burn bridges, even when you’re forced into plan B

A few years ago, EOS Worldwide dissolved its licensing program and launched its own operating system software. Ninety’s software had been built around that ecosystem, so this was a gut punch. We could have thrown a fit, taken our ball and gone home. Instead, we went back to the questions that keep our decisions aligned with who we are. We chose to stay agreeable, keep improving our own platform and remain true to our principles. When EOS later reached back out to reestablish the partnership, that grace paid off and we reengaged on far better terms.

5. Stay ahead of the curve, then be patient

You have to anticipate where the world is going and invest before customers even know they need it, whether it’s adopting technology in traditional spaces or integrating AI into core workflows. It’s important to temper your ambition with honesty, as real organizational evolution takes two to three years of grinding effort.

6. Culture has to fit the environment you’re operating in

The market has a major impact on what kind of culture you need. A fast-moving, highly ambiguous space, like what we see around AI right now, requires people who can live in the gray area, move quickly, work hard and adapt. A culture that was perfectly right for one environment can start to break when the environment changes.

7. Leadership demands evolve with the organization

Every stage of development asks something different of the people leading it. Some leaders keep expanding their capacity to handle complexity, while others hit a ceiling they can’t even see. For example, the right team at 10 people might not be the team that carries you through to 100 or 300 employees. Someone can be a wonderful human and strong cultural fit and still not have what the next, more complex seat requires. Building something enduring means telling the truth about what the company needs.

8. Own the one-way-door decisions yourself

Founders make plenty of bad calls. The point is to stay humble enough to see what happened, own it and get better. But some decisions can’t be undone, like letting people go. Those one-way-door moments can reveal a lot about the true nature of the organization and its leaders. You can delegate a lot of tasks and responsibilities as you scale, but you can’t fully outsource decisions that carry deep cultural consequences. Those you have to carry yourself and make sure they align with your values.

9. Build mechanisms for the truth to surface

Great companies don’t have bystanders. The thing that goes unsaid is usually the thing that eventually hurts you. Enduring organizations create shared language and enough trust that people feel comfortable raising issues before they become permanent problems. At Ninety, we lean on phrases like “succeed or escalate,” “what’s working, what’s not,” and “what are the growth opportunities?” They may sound simple, but each one gives someone permission to surface a concern early.

10. Remember that everyone’s job is to help the organization win

It takes more than everyone simply doing their specific function well or optimizing their own department. Everyone has to understand what winning looks like and be able to step outside their lane when the company needs it. That is where a vision, a handful of clear quarterly rocks and an integrated business operating system earn their keep: They turn scattered priorities into coordinated work that everyone can see.

Closing thoughts

Ten years in, with more than 18,500 companies now running on Ninety, I’m more convinced than ever that building a great organization is a beautiful mess. It’s hard, humbling and full of lessons you would never have chosen. Love the game, be great at the work, stay humble, show grace and keep getting better. If the creek don’t rise and the sun still sets, you’ll find a way forward and be stronger for it in the end.

It’s a strange moment to write about what makes companies last, with global uncertainty at historically high levels and leaders being asked to make huge bets on AI, talent and where the world is going. At the same time, employees are nine times more likely to be engaged when they believe their company has a secure future. 

Consider those two findings for a second: The defining tension of building a company today is that the ground is shakier than ever, and the people you lead need more steadiness than ever. That tension is exactly what the last decade of building Ninety has been about. 

I spent years as an investor and board member watching capable teams struggle with the same problems: lack of shared vision, cultures without purpose, priorities that didn’t translate into coordinated work and leaders who didn’t have a connected view of how their company was running. I founded Ninety to build the business operating system I kept wishing those companies had. In doing so, I started living these problems from the inside.