How To Start a Company

The first time I started a company, I made every mistake in the book. The second time, I made new ones. The third time, I began to understand that entrepreneurship is less a skill than a discipline — a set of habits of mind that need to be cultivated deliberately.

What follows is not a how-to manual. Books have been written on hiring, fundraising, product development, go-to-market. What I want to share is the prior question: before any of that, what does it take to turn an idea into something that lasts?

Start With Pain, Not Opportunity

The worst companies I've seen — and the hardest early-stage pitches to sit through — start with a market opportunity. "The X market is worth $40 billion. We plan to capture 1%." That is not a company. That is a spreadsheet with ambitions.

The best companies start with pain. Someone — ideally the founder — encounters a problem that is genuinely frustrating, expensive, or demeaning, and cannot stop thinking about how to fix it. The Founding insight of QLess was simple: people hate waiting in line. Standing in a queue is one of the most dehumanizing experiences of daily life. We set out to eliminate it. That animating problem gave us clarity through years of pivots, setbacks, and fundraising challenges.

Ideas Are Overrated; Execution Is Overrated Too

There is a persistent debate in startup culture: is it ideas or execution that matters? The answer is that the question is wrong. Both matter — but what matters most is the feedback loop between them. The ability to generate ideas, test them cheaply, fail fast, update your model, and iterate quickly is the real competitive advantage.

This is why experienced operators so often beat brilliant visionaries in the market. Not because execution beats ideas, but because they have learned to execute in service of learning — to treat every product release not as a bet but as an experiment.

Build the Team Before You Need It

The single most important non-product decision you will make is who you hire. Most founders hire too late (waiting until the pain is unbearable), too fast (panic-hiring the first warm body with a good resume), or too narrowly (people exactly like themselves).

The people you need most are the ones you are least like. If you are a builder, you need a seller. If you are a dreamer, you need an operator. The hardest thing in early-stage companies is admitting you cannot do everything well — and then actively seeking someone who does the things you can't.

The Long Game

Startups are not sprints. The companies that succeed over decades are built by founders who can sustain energy, curiosity, and integrity through disappointment. That requires knowing why you are doing this — not for the outcome (the exit, the valuation, the recognition) but for the work itself.

The companies I'm most proud of are the ones where I woke up every morning wanting to solve the problem — not wanting to have solved it, but wanting to work on it. If you can find that feeling, protect it fiercely. It is rarer, and more valuable, than any market insight.