Startup Stories: Andy Dunn, Bonobos Founder and CEO

Dec 11, 2018

The entrepreneur’s journey is never linear. It gives perspective to look at successful founder’s stories and what their path looked like. For Andy Dunn, Bonobos Foudner and CEO, he titled his mini essay, The Risk Not Taken. You can read the full article here, but to summarize:

keep moving, traveling and meeting new people. It’s the road not taken that you regret.

Andy Dunn shares the story of how he decided to start Bonobos, a process that left him living with a 6-figure debt, in pricey NYC, on a date at a cash-only restaurant…with insufficient ATM funds to pay the check:

“The feeling of no money in the bank, of rejection by ATM, is always a bad one. With a cash-only date in progress it became in fact one of the most sickening feelings I have ever experienced.”

He traces his current situation back to a decision that he was forced to make a number of years ago:

“If you can’t decide what to do, get on the road. You won’t find the answer. It will find you.”

Prior to starting Bonobos, Andy did a Bain consulting project in San Salvador for 6 months:

“I was working for an airline, and the travel on that airline was free if there was an open seat. I spent my weekends in Roatan, San Pedro, Antigua, Guatemala City, Havana, and San Jose. Fried chicken was often put in the overhead compartments of the planes.”

He became friends with people who inspired him to travel more, and would later become Bonobos angel investors:

“Two South Africans in particular, Matt Bresler and Dave Eadie, inspired me tochange. Four years later they’d both wire money into Bonobos as angel investors without really knowing a thing about the company. I wanted to be like them. Imitation, it turns out, is a great engine for personal growth. I decided to travel as much as I could. Over the next four years, squeezed between another job and two years in business school, I went to 30 countries. Over the past decade, I think the number is closer to 50.”

He learned that the risk not taken is far worse than the risk taken and failed:

“Very little is obvious in the research on human decision making and happiness. Very few things are proven. One thing that is proven is this: the only regrets the octogenarians have are for the risks not taken.

…which inspired him to turn down a VC job offer and join his friends who were selling better-fitting pants:

“We were going to take Brian’s pants and sell them online. We were going to prove that the internet was going to be come the core medium for storytelling, for delivering great service, and for transacting goods: that it was the future of how brands would be built.”

The life on an entrepreneur is risky & challenging. It is not a journey that should be taken alone. At Jumpstart, we are focus on mentor-driven guidance and building a community of entrepreneurs around you.

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