Lessons from 15 Years On

It’s been 15 years since I filed that paperwork to start Seabourne Consulting in 2009, and honestly, I wasn’t thinking beyond the fact that I didn’t want to job hunt. Starting a company right after the global financial meltdown wasn’t, on paper, my best idea. But I was young and optimistic, and bureaucracy was no match for that kind of energy. So, in a mix of timing, necessity, and a bit of naïveté, I dove in.

Fast forward, and somehow, it all worked out. Seabourne grew to 40 people, I launched a few spin-offs, and even sold one. I’ve celebrated wins, lived through losses, and, if I’m honest, probably ruffled more than a few feathers along the way. I’d like to say it was all strategy, but there’s no sugarcoating it: luck played a much bigger part than I ever imagined.

Here’s what I’ve learned in the past decade and a half:

Cash is King

If you’d asked me early on, I would have sworn that revenue was the key to scaling a business. Get more customers, money flows in, and everything else falls into place. Except it doesn’t. What I’ve learned—often the hard way—is that cash flow is king, not revenue. Maximizing available cash, whether from financing or profits, is essential to staying alive in the game. The moment you lose sight of your cash, you’re on a slippery slope.

I remember the first big contract I landed that launched the company: working with the Federal Communications Commission to launch an open data platform. At the time, it was by far the most money I had ever planned for, and I immediately started creating complicated spreadsheets for how I would spend all the incoming cash. But nowhere in those models did I plan on saving the money or building for sustainable growth. In my mind, the purpose of revenue was to be spent in order to grow, and if you didn’t spend it, you weren’t growing. This kind of binary thinking ultimately created a number of (totally foreseeable) cash crunches and layoffs when times inevitably got less good.

Minimizing expenses matters, too. It’s all too easy to get comfortable when the books look good and overlook where money’s leaking out. I’ve been guilty of ignoring expenses when I should have been paying attention, and that always backfires when income takes an unexpected dip. Finally, increasing revenue is a long game—one that’s unpredictable at best. The most you can do is stay in the race long enough to take advantage of growth when it decides to show up.

Growth Can’t Be Forced

Business growth is a bit like trying to rush a garden to bloom in winter. All the effort, all the long hours, and pushing won’t change the fact that conditions aren’t right. You can’t bend the seasons to your will, and trying too hard often leads to burnout. I’ve seen it, lived it, and now, I try to do less—but when the right opportunity presents itself, I’m all in.

After a couple of years of successes (and bumps) at Seabourne, I decided we needed to diversify and try our hands at building and selling software products. The margins in consulting felt too low, and I had these dreams of winning the lottery and launching the next big product company. Over the next few years, we self-funded and launched three different product concepts, each of which lost money.

My mindset was so focused on creating things that I failed to look up and examine the market we were trying to enter and our potential customers. Based on our work in D.C., we had focused on data products for NGOs and governments, completely ignorant that 2011 and 2012 were probably the worst time to do this, as government budgets all over the country were in deficit. I would finally get a success in this space, but not until five years later when the larger macro environment had improved.

Back in 2009, I had no idea how lucky I was to be based in Washington, D.C. at a time when government stimulus was fueling the local economy. It was a fluke, but that was the environment that helped Seabourne survive when many others couldn’t. Timing and luck, I’ve learned, are better business partners than sheer determination.

Less Is More

As the company grew, so did the number of voices offering advice. More people wanted to get involved, most with their own interests at heart. I wish I had kept my circle smaller. There’s wisdom in focusing on fewer, higher-quality inputs. You don’t need an army of advisors—just the right ones. In fact, smaller management teams and fewer advisors often mean better, more focused decisions.

In my second year of Seabourne, we continued to grow, and it made sense to bring in some outside perspectives on our strategy and growth path. But as a closely held company, we didn’t have directors, so I created an advisory board instead. For the next six months, I went around trying to fill my board with experienced folks who seemed excited by me and what we were doing.

Little did I realize at the time, but the board ended up being a net negative. By including lots of people with different experiences, I ended up getting many different and often contradictory pieces of advice. I spent more time managing egos and group dynamics than I did developing strategy, and in the end, I suffered a fair amount of reputation damage because the company wasn’t doing as well as hoped, and I ended up not taking a lot of the advice I had asked for.

Get a Therapist

No, really. I’m not being glib. Running a business will bring all your unresolved baggage to the surface. Whether it’s family dynamics, personal insecurities, or old wounds, they’ll find a way to make themselves known. And when they do, they’ll sabotage your decision-making. In hindsight, I wish I’d sought out professional help earlier, not only for myself but for the people around me. My identity became so wrapped up in the company’s success that I often put business ahead of the people I cared about. That’s a tough mistake to live with.

Looking Forward

We’re entering a new era. The days of easy financing and cheap debt are behind us. Venture capital and private equity aren’t going to flow like they did during the zero-interest-rate years, which means we’re all going back to basics. Competent business operations will once again be the differentiator, and cash flow will be king.

And then there’s AI. If I were starting a company today, the first question I’d ask isn’t, “Who should I hire?” but rather, “Do I need a person to do this at all?” The shift toward usage-based models, driven by the cost of computing in AI, will transform business models. The days of 95% margins may be behind us, but that’s just part of the evolving landscape. Adapt, or get left behind.

As I reflect on the past 15 years, I realize that building a business is as much about navigating luck, timing, and market forces as it is about strategy, effort, and vision. The journey is unpredictable, and while you can control many aspects of the process, the truth is that adaptability, resilience, and a clear understanding of your own limitations are what keep you moving forward. There will always be new challenges, emerging trends, and unforeseen obstacles, but if there’s one thing I’ve learned, it’s that the most important part of success is simply staying in the game long enough to see it happen.