Brandeis International Business School

017: Ordinary People Solve Extraordinary Problems

And so can you

Jon Hayes is the founder and CEO of RewardStock, a travel startup that helps travelers book trips with frequent flyer miles and travel rewards points instead of cash.

Before becoming an entrepreneur, Jon was a Wall Street investment banker with eight years of mergers and acquisitions experience at Citigroup. But then, he left Wall Street to launch his first startup RewardStock, which was featured on Shark Tank, where Jon secured an investment from the influential investor Mark Cuban.

From the Dorm Room

When Jon started his college career at Princeton, he was on a very different career path. He thought he’d be pre-med or pre-law, but then he took an economics class and fell in love with the concept of analyzing incentives.

He started researching what people did when they graduated from college with a degree in Economics, and the two big career paths for Princeton graduates were management consulting and investment banking. He started networking like crazy, became president of Princeton’s business society and got an internship that eventually led to a job offer.

So right after graduating, Jon jumped feet first into the world of Wall Street.

To the Boardroom

When Jon started as an investment banker, he was a single guy in Manhattan who had plenty of time to focus on trying to making a good impression at his job. So, it didn't bother him to work the crazy hours that investment banking requires. But eight years is a long time to work on Wall Street, and most of his peers left after a year or two.

To give you some perspective on the kind of hours and stress Jon was under, he was once working on a deal that had to be revised with only three days notice. He did a week’s worth of work in less than three days, working in the office without sleep. He ate two meals over that entire three-day period.

For a while, he really did enjoy all of the stress and high-pressure, and took pride in being able to do something that many others couldn’t. But after he got married and, with that, got new priorities, the Wall Street lifestyle started becoming too much.

It was actually on their honeymoon that Jon first thought of the idea for RewardStock. They went on this amazing honeymoon where they flew first class to the Maldives and stayed for eight nights in a top-of-the-line, over-the-water villa. The resale cost of that travel would have been more than $40,000 if they had paid cash, but because they had figured out reward strategies, it only cost them $200 in taxes and fees.

“So, not only did we have this amazing first-class honeymoon, but I also kind of came away from that experience feeling like this was something that I wanted to make sure I got every time I traveled... But, also, something I thought many people in the country want to do.” This was something that anyone could do – it wasn’t a connection or family member that hooked him up – it was just planning out a strategy and executing it. The hardest part was the planning, but that was a problem they could solve for people.

The Entrepreneurial Edge

Every week, we highlight one piece of advice for aspiring, struggling, and successful-but-want-to-be-even-more-successful entrepreneurs:

Early in Jon’s academic and professional career, he had an epiphany: Everything that is being done in the world is being done by a person that is as human as anyone else, and has all the flaws of everyone else – and yet, many people figure out ways to do things that are extraordinary.

One of his mentors put this in the context of banking, saying you don't have to look around the room for someone to give you approval or permission to solve a problem. You don't have to defer to someone just because they're more senior than you. If you have confidence in yourself – you know you're in your position for a reason and you know you're a smart individual – then you can come up with new solutions to problems and do things that are extraordinary, too.

“If there is a a deal to be had, why not you? Why shouldn't you be the one to bring that deal for the company? Or if there's a problem to be solved, why not you? Why shouldn't you be the one to come up with that solution?”


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