Startup Strategy

Most failed startups didn't have wrong ideas. They had right ideas, executed at the wrong scale, at the wrong time.

Founders obsess over product decisions. The hire that actually determines company trajectory gets maybe a week of consideration.

Homejoy burned through $38M optimizing the wrong metric. The number that actually predicts startup survival isn't how fast you spend — it's what you're buying with each dollar.

Cheap pricing feels safe for new founders. It's often the thing that makes buyers walk away.

Every successful startup has a story about the customer they almost built for instead of the customer who actually mattered. Here's what that mistake looks like in practice.

Everyone obsesses over who joins a startup first. The hire that actually determines your trajectory is usually the one after that.

When a startup runs out of money, founders obsess over their cap table and their team. Their customers are an afterthought. That's a moral failure, not just a strategic one.

Before the database, the dashboard, or the data team, there was a Google Sheet. And for many successful startups, it held up longer than you'd expect.

Better products lose to inferior ones all the time. The difference is almost never quality. It's who had a path to the customer.

Founders obsess over not hiring sales too soon. The opposite mistake kills just as many companies, just more slowly and with better excuses.

Figma spent years iterating on a product almost nobody used. Then they stopped. Here's what that decision actually looked like.

The customers who saved you in year one are often the ones constraining you in year three. That loyalty runs both ways, and it's costing you.

Being first is overrated. The companies that dominate markets are rarely the ones that invented them. Founders just can't admit that.

Zenefits hired like a 5,000-person company when it had 500 employees. The wreckage was instructive.

Stripe's early growth nearly destroyed the company. The lesson isn't about bad customers. It's about what happens when you say yes to everyone.

Everyone celebrates the first customer. The second one is the only signal that actually tells you something useful.

Pricing below your costs doesn't buy you time. It just makes you fail slowly, then suddenly, with a customer base you can't actually serve.

Raising money before you have leverage feels like progress. It's usually the opposite. Here's what it actually costs you.