3 Things I Wish I Knew When Founding a Company 20 Years Ago

Twenty years ago, I launched my company with a head full of optimism and a thin playbook. The market was smaller, capital was scarcer, and the word “scale” usually referred to manufacturing, not software.

Let me save you twenty years. Through three recessions, a pandemic and a Russian hack I’ll never forget, I learned that every outcome — good and bad — was dictated by three things: approach to equity, obsession with speed and commitment to building for the future, not just the present.

If I could sit down with a new B2B founder today, these are the three conversations I’d make sure we had — the same ones I wish someone had with me early on.

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1. Don’t give it all away

Early on, most founders pay their first hires in equity. Each grant solves an immediate payroll problem but also sets the “going rate” for everyone who follows and nibbles away at the founder’s ownership. Over time, as more hires come on board expecting similar equity deals, the option pool expands, and suddenly, there’s not enough left to offer meaningful stakes to the senior leaders who matter most for the company’s next phase of growth.

To fix this imbalance, you must recognize that you have precisely one window to fix it, and that’s now. It means having the hard conversations about revisiting vesting, adding performance cliffs and making room for future partners. The pain of doing it now is nothing compared to the pain of explaining a broken cap table to new investors. We survived a similar case because we ripped that band-aid off, just before our next round made it impossible to do so.

Today, I tell founders to treat equity like a reserved seat at the board table: only give it to people whose judgment you’ll still respect a decade later. If only I had known that timing and value alignment in equity partnerships mattered so much, I would have saved myself countless hours of renegotiation had it been available back then.

Related: 3 Things to Consider Before Going ‘All in’ on Your Startup

2. Move faster than feels comfortable

Another blind spot for most founders is velocity, which goes unnoticed until it starts costing real money. Founders who insist on flawless forecasts and endless debate often end up watching the market sprint ahead while their projects idle in “analysis” mode. It’s crucial to remember that most opportunities have a shelf life, and the price of hesitation usually outweighs the cost of a measured mistake.

With that in mind, I had to make sure our teams embrace a bias toward action. Each year, we challenge ourselves to shorten our decision-to-execution cycle. We concentrate on the highest-payoff priorities, make the call, and then move immediately. While we may inevitably miss the mark at times, we correct them faster than we once made them.

Clearly, there’s no substitute for experience. The older I get, and the more seasoned our leadership team becomes, the quicker we can weigh risks, spot patterns and avoid analysis paralysis. That pace creates its own momentum. Once speed becomes the expected culture, your team instinctively builds processes to protect it. So when early-stage founders ask me how fast they should move, my answer is always faster than you think, and then faster still.

Related: What Every B2B Brand Should Be Doing to Earn Trust in 2025

3. Build like you’re already big

In hindsight, we made the classic mistake of building to match the previous quarter’s demand instead of our initial goals. We told ourselves that fifty customers was a stretch, so we provisioned servers, support seats and deployment scripts for a company that size — nothing more. As we started to scale, sales momentum started inching us closer and closer towards the ambitious 5,000-site mark we’d only daydreamed about.

Many founders discover, right in the middle of a launch, that an early single-tenant setup and bare-bones deployment pipeline won’t stretch to meet sudden demand. Deadlines start to drift while the team upgrades to multi-tenant architecture and spins up redundant cloud instances. The extra spend always outruns what a forward-looking investment would have cost, yet the experience makes scaling cheaper while it’s still in theory.

That’s why every roadmap review should open with a simple stress test. For example, for us, “What breaks if we need to bring 150 sites online next month?” — and why budgets must include the infrastructure to pass that test, even when today’s revenue makes the line item look ambitious. Planning for surge capacity before it’s urgent keeps launches on schedule and turns growth into a feature, not a fire drill.

The second truth is that infrastructure alone won’t save you; the people building and running it will. Think of your core team as the “founding fathers” of a forever company. You need complementary skill sets, shared loyalty and relationships that hold under pressure because pressure will definitely come. Get that inner circle right, and you’ll have the resilience (and the conviction) to keep investing ahead of your growth curve.

The uncomfortable math of first principles

Looking back across twenty years, I see with perfect clarity how every triumph and setback connects to our first principles. Mind you that those choices were never comfortable in real time as they tug on payroll, patience and budgets that already feel stretched. But that discipline consistently bought us agility. It gave us the freedom to pivot when the market turned and the readiness to jump on a once-in-a-decade chance. That, more than any clever tactic, is how you build an institution designed to outlast its founding story.