Good Fortune: An Angel Investor Helps Entrepreneurs Soar

“The team, the team, the team.”

The famous words of legendary U-M football coach Bo Schembechler are inspirational not just in the arena of sports but also in the world of entrepreneurship.

“An entrepreneur can’t do everything themselves, so they need a team around them,” says Geoff Entress, ’98, a Seattle-based investor who has backed more than 125 companies in the last 15 years, including keyboard technology company Swype, casual game developer Big Fish Games, social media manager HootSuite, and many, many more. “If you can show that you’ve convinced other great people to come with you, you can convince investors.”

Entress has been listening to pitches and helping entrepreneurs get a leg up in the business world for most of his life; he started investing at a young age in partnership with his dad, an oral surgeon who, just before he retired, founded his own investment firm. Entress earned his undergraduate degree at Notre Dame, his MBA from the Tepper School of Business at Carnegie Mellon University, and his JD from Michigan before heading to Seattle.

Today, the Pittsburgh native is a venture partner with Voyager Capital, sits on the boards of 11 companies, and is what’s called an angel investor—that is, someone who provides personal capital to businesses trying to get off the ground. A recent article by geekwire.com called him “perhaps the best known professional angel in the Northwest.”

Success, Failure, and Making the World Better

Entress has made a successful career out of picking which companies have what it takes to succeed. And his work comprises much more than just opening his checkbook.

“The secret to getting into the best deals is to be a value-add investor. Serving on the board, doing introductions to customers or executive team members, going that extra step. Those activities take a lot of time. But that’s why you’re asked to be included in the best deals.”

A team of people must work well together for an investment to work, he says: establishing parameters of the investment, thinking through the pitfalls, and negotiating the details, which can take a while.

“When you’re meeting with entrepreneurs, you have to consider that you’ll be spending a lot of time with this person,” Entress says. “It’s a long-term relationship. You have to like this person. A main reason I won’t do a deal is because someone is a jerk. No way I’ll invest if I don’t like the person. If you don’t like the person, probably others won’t either.”

A successful entrepreneur has to be more than just likeable, however. “There’s always a different adjective about what an entrepreneur should be: courageous, confident, intelligent,” Entress says. But a big one on his list is convincing.

“They have to be passionate about what they’re doing, and they have to be visionary. They have to convince you as an investor that what you’re seeing is something that can make the world better, and that they’re the person who will go out and execute against that. They have to get you to believe in a quality idea, and that they can attract others to join along into this crazy thing that might not work.”

Entress predicts that maybe one out of 10 deals will hit it out of the park. He’s had a number of home runs in his life, but he’s had many big strikeouts, too—specifically companies he had the opportunity to invest in, but didn’t. This includes YouTube (he thought it was just “another video site”) and StubHub (a trusted source told him not to sink money into it).

“When you see several hundred or more deals per year, you’ll miss some for sure,” he admits. He also says there are cases in which the idea is sound, everyone works hard and does what they can, and the business still fails. He cites his own startup company, Urban Earth, a hip-hop music and culture site that sold digital music in the late 1990s. “It could have been big, but it was bad timing. We were caught up in the dotcom collapse, and Napster was out there making it untenable to sell digital music. You’re always going to miss some.”

Advice for the Next Generation

Entress shares his wealth of experiences and advice with the next generation of entrepreneurs by serving on the advisory boards of the Buerk Center for Entrepreneurship at the University of Washington, the Gigot Center for Entrepreneurship at Notre Dame, and the Donald H. Jones Center for Entrepreneurship at the Tepper School of Business at Carnegie Mellon University. 

Part of his goal is to encourage universities to take entrepreneurship out of the business school and spread it across disciplines—something the University of Michigan has done with programs at the Law School, the Ross School of Business, and the College of Engineering; start-up accelerators that assist students across campus; and more.

“It’s important to get all students exposed to entrepreneurship and to get classes offered to that end.”

But even for students at a school without access to an established entrepreneurial curriculum, he says there’s plenty that they can do. “Reach out to people across schools and meet others. Enter business plan competitions, and get involved. Start finding what appeals to you.”

For those interested in dipping their toes into the entrepreneurial waters, crowdfunding sites such as Kickstarter and IndieGogo can provide funding for an idea in the form of online donations. The platforms, Entress says, “work well for pre-sales of products [an entrepreneur] is going to make.” For his part, he’s not worried that the proliferation of funding sites, and people wanting donations for projects, will have a negative impact on entrepreneurship.

“A lot of our cultural heroes are entrepreneurs. I don’t know that we’ve tarnished the dream yet.”

Another piece of advice?

Go to law school.

He’s adamant about the importance of the skill set he gained from his time at Michigan Law. “I often get asked, ‘Hey, was it worth going to law school?’ I think law school is a phenomenal education. It changes the way you look at the world. I use the skills I learned at U-M every day.”