If Michael Jordan were an entrepreneur

Tripit and Hotwire co-founder Gregg Brockway: The basketball star's attitude is the right one

You read about Gregg Brockway's lessons learned in the "Does an entrepreneur need an MBA?" series. Now watch and listen to him elaborate more about the lessons he's learned. And, this entrepreneur has learned a lot, given what he's been through: a startup failure as well as taking a startup from the beginning all the way to a successful M&A exit.

What makes a great entrepreneur?

"There's three things to be successful," he said. "A differentiated vision... second, a great team, and a grim determination to power through." Importantly, entrepreneurs have to realize that the "entrepreneurship" game isn't an individual sport. "Talent wins games; team wins championships," said Gregg, quoting former basketball star Michael Jordan.

Gregg is a two-time entrepreneur, having founded Hotwire (sold to IAC for $650 million), and most-recently Tripit (raised $13 million in venture funding). Gregg became an entrepreneur after first having a stint as an investment banker. He felt constantly pulled to enter the operational side of a company, as opposed to just the advisory work that’s done as a banker. 

While Gregg had a great success, and appears to be on his second, he did have a failure. This is often a right of passage for many great entrepreneurs. 

Gregg joined a garage startup in the late 90's.

Unfortunately, or fortunately, that startup failed. "Ultimately, we lost all the money, including a decent chunk of my own," he said.

What are Gregg's biggest lessons from that failure? In a nutshell: The importance of leadership; the importance of a differentiated product and not a me-too product in a crowded space. And, the importance of creating options (something Kevin Hartz, CEO and co-founder of Eventbrite said in his Lessons Learned segment).

An entrepreneur needs to focus on "a lof of different ways to win," he said. One way to do that is to not be totally dependent on one customer or partner.