014: How To Break Into The Tech Startup Industry (Ryan Delk)

Ryan DelkDid you ever ask yourself: what’s the craziest thing I can do in this situation? If not, you might after listening to our guest for episode 14! He did and it paid off immeasurably.

Ryan Delk of Gumroad got his technology legs through an experience in Nairobi, Kenya and it all started when he asked himself that very question. Asking that question led to an internship in Kenya which helped him see tech start-ups were his cup of tea.


Ryan, a native of Orlando Florida, was always interested in how to create value for other people and have them happily pay him for it. As a kid, he was busy coming up with company ideas like lawn services for his neighbors, fixing and flipping iPhones for a profit and the like.

When he went to college, he was sure his path was investment banking or working on Wall Street. But that changed during his first internship at a bank in Orlando where they did loans of $10-$40 million. He enjoyed it, but in the end he realized it wasn’t the perfect fit for him.


  • Should you start in a smaller market or dive into the larger one right away?
  • The opportunities in Africa for technology today.
  • How many cold emails did he send while trying to get into the tech world in San Fran?
  • Does product drive growth according to Ryan?
  • How did he overcome his fears about networking his way into the tech field?

The next summer he asked himself: What’s the craziest thing I can do? What’s something I can do that I won’t ever be able to do again? And through a family connection, he found it.

A family friend was the founder of iHub (and other businesses) and had some projects in Kenya he wanted Ryan’s help with. So Ryan set off on a three-month adventure in Nairobi, where he worked on growing a tech incubator space as well as technology-related conferences.

Through that experience, Ryan developed relationships that opened doors for him and also gave him the hands-on experience he needed to see that tech start-ups were his bag. Shortly after, he found Gumroad and reached out to the founders. Although it took some time and quite a bit of chutzpah on Ryan’s part, he did become a part of the company after he moved to San Francisco.

Today Ryan loves working at Gumroad, from the teams they have created within their organization to the innovation they are bringing to the marketplace.

Let Ryan know what you liked about his story and what you learned from his experiences! Drop a note below in the comments or Tweet us!

Tweetable: “Add value before you ask for value.” Ryan Delk  



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