Trap Travels – Interview with Adam Goldstein of Hipmonk

Hiscox Brave Entrepreneur Interview Series

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Interview series sponsored by Hiscox Small Business Insurance. Hiscox specializes in IT / technology, marketing, consulting, health and beauty, photography and many other professional services business, creating coverage for specific risks in your industry..

The day after graduating from college, most of us are still celebrating or recovering from the night before. Adam Goldstein, now 27, graduated from MIT a day after he started hipmunk with co-founder Steve Hoffman.

Travel-planning site HipMonk now employs more than 40 people and has raised more than $ 40 million since its launch about five years ago. Adam described the company as “the fastest and easiest way to plan a trip, helping travelers save time and money.” By focusing on the hassle of a trip, visitors can see comprehensive search results that represent the least and most painful travel options, showing the time saved and the time spent in transit depending on the chosen option.

Pain Debate

In his senior year leading the MIT debate team, Adam was crowned the North American Debate Champion. As team captain, Adam was responsible for booking travel plans for the entire team. He quickly realized the challenges of finding, coordinating and booking travel plans for a large group. Poor customer service and the dull user interface presented a very good opportunity to pass on his negative experiences.

When it came to making hipmunk, the hardest clients to please Adam and Steve were themselves. “We had to go through a bunch of different iterations until we found something we thought was easy to use and very useful – useful enough that none of us would go back to anything else,” Adam said.

Creating an end-to-end product that was better than anything else that exists is part of the necessary solution. The product was nicely assembled, but you can’t get travel service without the offer. Airlines and hotel chains are often reluctant to provide inventory to unreliable startups. “It was a chicken and egg problem.” With perseverance and a bit of luck, they were able to get their first delivery just in time for Demo Day at Y Combinator. Shortly after Demo Day, Hipmonk received their first Million Seed Fund.

After teaching middle school how to program, Adam first started practicing his entrepreneurial side. Instead of buying a chess clock to play chess, Adam created a computer program that would act as a chess clock. He soon realized that he could sell his apps online. It may not seem like much money right now, but it’s pretty impressive to make $ 20 a week selling apps while still in high school.

Q: Would you still be an entrepreneur if you never learned to code??

A: “I’m not sure it happened to me that it was a reasonable career path unless I had firsthand experience that distributing software online was relatively easy.”

Hip advice

Due to the complexity of the search function, Adam’s background in programming was an important aspect of the company’s construction and growth from the beginning. When asked how entrepreneurs can find a technology co-founder, Adam replied, “The best way to find a technology co-founder is to become one yourself.” He went on to explain that even having a “passing acquaintance” with programming would help to start and build the credibility and knowledge needed to hire other programmers.

Adam’s initiatives came from an interest or pain that he wanted to solve. Asking aspiring young entrepreneurs for his advice, Adam recommends, “Make sure you have a firm belief in what you are working on. Our conviction came from our personal experience with the problem we were trying to solve. The firm belief of other people comes from the fact that they are excited about a big income opportunity and they know the market well. I have never seen an entrepreneur who has succeeded in trying only one idea for which there is no excitement or reason for them to invest deeply. There needs to be some basis for why this is being done, why it is exciting for entrepreneurs, or why it is not worth spending time on. ”

Listen to the full interview with Adam Goldstein below.

Additional interview highlights

What are the biggest risks you face when starting hipmunk? “Risk of failure.”

– From his experience with the debating team, Adam learned “how to speak slowly and clearly in front of a group of people.”

The importance of communicating clearly as CEO: “At first, when I was adjusting from college to management, I didn’t fully understand how employees could reason (explain). My style was just that See this debate and where we end up. When you are managing people; If you say something like, “What is it?” It’s called “Hey, Adam wants us to do this.” It makes sense to distinguish between these things when talking to people. “

– Adam talks about writing his first book at the age of 16 and the importance of writing.

Hip Future: After recently launching a partnership with Yahoo! Travel and Yelp, HipMonk are now working on new features and continuing to innovate in their search features and processes.

Listen to the full interview here:


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