Startup Strategy

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.

Early adopters save your startup. They also, if you're not careful, define it in ways that make scaling nearly impossible.

Discounting your way to early traction feels like progress. It's usually the first step toward building a business that can't survive.

The customers who save your startup in year one are often the ones who quietly strangle it in year three. Here's why.

Success teaches the wrong lessons. The habits that got you through your first company are often exactly what will sink your second.

Most founders set prices by asking 'what's fair?' The actual question is different, and getting it wrong quietly kills companies.

Three of tech's biggest companies nearly collapsed serving customers who were never going to make them successful. The pattern is more common than founders admit.

Most founders treat market focus as a constraint to overcome. The ones who win treat it as a weapon.

Chasing product-market fit too early is one of the most reliable ways to build a company that fits the market that exists instead of the one that's coming.

Figma's pricing wasn't aggressive. It was a statement about what kind of company they were building and who they were building it for.

The funding advantage is real. It's also a trap. Here's what actually happens when startups have too much money to spend.

In 2013, every reasonable person told Butterfield that enterprise chat was a dead market. He ignored them. Here is why that was the right call.

Everpix had hundreds of thousands of users and a product people loved. It shut down because it priced itself into a corner it couldn't escape.

The waitlist, the invite code, the cryptic landing page. Deliberate obscurity is a growth strategy, and it works because scarcity is a feeling you can manufacture.