Member Spotlights

Member Spotlight: Jesse Randall '11

Serial Entrepreneur, Dive

If there is one thing that all T-Birds can agree on, it’s a love for international travel. Jesse Randall ’11 is no different. First bit by the travel bug when he went to live and volunteer in Puebla, Mexico for two years after high school, he continued with a college internship in Brussels and most recently, he and his wife just returned from a trip to Romania and Bulgaria. Next time, they hope to make it a family trip with their four young children.

Not only was Jesse bit by the international bug, he was bit by the entrepreneurial bug. With a passion and dedication for start-ups, Jesse has worked with over 150 of them and even founded six on his own, in the last seven years. His career has been in start-ups, funded companies and a venture capital firm, in industries such as healthcare, consulting, and internet software, his primary industry.

Jesse builds software for the internet, mobile applications and more, to help grow companies. As he describes it, start-ups have three phases: Validation (0-1) to get your “ducks in a row”, Initial Sales (1-5) figuring out how to sell and get traction, and then scaling a Repeatable Process (5-100). He focuses on the 1-5 --  the hard, early growth, establishment stage of a business that has a product or service and is ready to start making sales.

Jesse’s latest company, Drip, creates sales infrastructure services for companies. He builds and operates the system finding the ecosystem of who they should get in touch with, reaches out to start the conversation, and then hands off those leads. He leverages LinkedIn and a host of cutting edge technologies toolsets that have only existed for the last couple of years. This helps him manage 1,500 unique contacts automatically on behalf of each client.

An additional project Jesse is working on right now is a digital travel publication,, a bucket list information site. This portal creates a report of the thousands of sites from abroad and creates a standardized way to present that information so a user can utilize it more easily. His intention is for people to mark their bucket list items to save as a “wish list” for later as a personalized list of 100 things to do in life. The site and content is under construction and should launch in the next 8-10 months.

Jesse lives in Arizona, not too far from Thunderbird, and commented that there is 10x the start-up activity in the valley since 2010. For T-birds that are interested in start-ups, Jesse has this advice to offer:

“Just do it! Start with nights and weekends, and try to determine if there is really something there.”

His challenge to every entrepreneur is to get to $10,000 in monthly reoccurring revenue on your own. If you can’t do this with the skillset you have, you need to go find a skillset that is valuable to somebody. The best thing you can do is to create something, get it in the hands of someone else as fast as possible, and generate revenue. One of the biggest things that he has learned along the way is the longer you wait to do the journey, the bigger the risk it is to take that journey. Just like travel, sometimes you just have to go for it and embrace the adventure.

On his weekends (and very early mornings), Jesse enjoys competitive cycling and training for triathlons. He is doing the 107 mile Tour de Tucson in November, and is training for his first half-Ironman race in the spring. If you’re ever in town he’ll gladly take you out for a ride!


Connect with Jesse Randall here!


Special thanks to Spotlight Author, Liz Peck '15, Team TIAA Volunteer

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