Startup Gold

Why Great Entrepreneurs Should Optimize for Rejection

Chris Jaeb, founder of, teaches entrepreneurs how to be more efficient

Aaron Dinin, PhD
3 min readSep 7, 2021


Photo by Isaiah Rustad on Unsplash

Welcome to the first installment of Startup Gold! In this series, I’ll be sharing “gold nuggets” of startup wisdom I’ve personally recorded during interviews for my podcast series, Web Masters. The entrepreneurs I interview have sold their companies for millions or billions of dollars. During our conversations, they often share valuable “nuggets” of startup wisdom that don’t fit into the theme of the episode and get left on the cutting room floor. Rather than trash that great advice, I collect their “gold nuggets” and share them here. Enjoy!

Gold Nugget #1:

“My goal was to drive everyone to a no. The quicker I could get people to say no, the sooner I could call the next person. Every time I got to a no, I was getting closer to getting a yes.”

— Chris Jaeb @

Who said it:

Chris Jaeb originally founded the company that became, which is the company Mark Cuban bought from him and would eventually sell to Yahoo! For $5.7 billion.

Why entrepreneurs should care: was the first company to use the Internet as an audio broadcasting platform for sports and other notable events. In order to do that, the company’s founder, Chris Jaeb, had to secure broadcasting rights, which was difficult and time consuming work that required lots of cold calls to people who often hung up on him.

The same is true for your startup. As an entrepreneur in the early days of building a company, you’re going to be reaching out to lots of people — potential sales prospects, investors, partners, and employees — and trying to convince them to work with you. Most will ultimately reject you.

However, because people are nice (and/or don’t like being confrontational), they’ll still talk with you even when they know they’re going to eventually turn…



Aaron Dinin, PhD

I teach entrepreneurship at Duke. Software Engineer. PhD in English. I write about the mistakes entrepreneurs make since I’ve made plenty. More @