Writing

Seven Hard-Earned Lessons for First-Time Founders

Starting a company is a crash course in humility. You’re juggling 100 decisions a day, half of which you’ve never faced before. You’re trying to build a product, grow a business, and stay sane—all at once.

Here are seven principles I’ve seen trip up first-time founders (myself included). If you're just getting started, I hope this saves you some scar tissue.

The Founder’s Vision Trap: Why Culture Beats Tech Every Time

It starts, as these stories often do, with a bold vision.

A founder has an idea — one they’re convinced is going to change the game. It’s innovative. Disruptive. The kind of idea that turns heads and opens investor checkbooks. Before long, there’s money in the bank, a team in place, and the runway to bring this vision to life.

From the founder’s perspective, the stars are aligning. The idea has been validated — after all, someone just put money behind it. Now it’s just a matter of execution.

But this is where things often go wrong.

What Design Teams Can Learn from Air Traffic Control

When pilots call up air traffic control (ATC), they don’t just announce their presence—they request a specific level of service based on their needs. For small aircraft, this often starts with a basic service, where controllers keep track of the flight and notify emergency services if something goes wrong. If pilots need more, they can ask for a traffic service, where ATC provides warnings about nearby aircraft. For even greater support, there’s a deconfliction service, where controllers actively give instructions to help pilots avoid collisions.

This structured approach got me thinking: Should design teams operate in a similar way?

Why VCs Say No: The Real Reasons Behind the Rejections

When a VC passes on your startup, it often feels personal. But in reality, most rejections come down to patterns they’ve seen before. Sure, some decisions hinge on chemistry or a gut feel, but most are rooted in a rational (if sometimes unspoken) assessment of risk and return.

That said, storytelling still matters—a lot. Founders often fail to tell the right story. You need to make your vision clear and believable, your momentum feel part of a deliberate and executable plan, and your success feel inevitable. VCs see dozens of decks a month, many tackling similar problems. Your job is to make yours stand out.

Here are the most common reasons why investors pass, grouped into themes they’re evaluating in every pitch.