16. Elizabeth Yin

CEO and Co-founder: LaunchBit

“The first company I started, a social shopping application, was a complete disaster. We built out what we thought was an awesome tool, but nobody wanted it. We wasted about $20k and about 1.5 years. From that experience, I realized that as much as there is a shortage of tech talent, the hard part isn’t the technology — it’s getting user demand.

If I were to have done things differently, I would’ve tested the market with little hacks before building out a product. I would’ve created landing pages to capture contact information of potential users and would’ve talked with them beforehand. I would’ve generated fake buttons that led nowhere or to a “coming soon” message to measure demand. In short, I wish I’d known to build as little as possible to test the market before building a product.”

15. Nick Francis

Co-founder and CEO: Help Scout

“I wish that I knew how difficult it is to acquire a customer, get them to pay for your product and believe it’s as magical as you think it is.

Most startup founders count on customer acquisition as a foregone conclusion, yet it’s the number one thing that keeps them up at night for the first 2-3 years if not longer. Every part of that process is deeply challenging for a company. It also doesn’t happen quickly.”