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.
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.
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.
As a Venture Partner at a VC fund, I've reviewed hundreds of pitch decks in my time. In fact most funds will receive thousands of decks a year, with only a small fraction leading to conversations and even fewer resulting in investments. With those kinds of odds, your pitch deck needs to be exceptional - think 8 or 9 out of 10 - to stand out.
Back in 2005, I wrote my first book—and learned the hard way why traditional publishing isn’t for everyone. The book, one of the first on CSS design, was published with Apress and turned out well, but the experience of working with the publisher was anything but fun.