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4 big questions for aspiring entrepreneurs

After interviewing a bunch of founders, Renny McPherson — author, investor, entrepreneur — offers some pointers.

Donna and Rosy Khalife speak at the Surprise Ride debate watch party. (Photo by Tajha Chappellet-Lanier)

I’ve spent a lot of time interviewing entrepreneurs who are in the middle of building businesses, to better understand their motivations, concerns and paths to entrepreneurship.
I collected a number of lessons in interviews with 16 entrepreneurs for my book Entrepreneurs in the Midst: Stories from Founders, Creators, and Builders.
Here are four questions for any aspiring entrepreneur to ask as you launch your business.

Question 1: Does ‘The Why’ makes sense: Is your startup the culmination of purposeful thought and work?

  • Though Will Ackerly, cofounder and CTO of D.C.-based Virtru, started the company in 2012, he had been working since 2005 on making secure collaboration really easy. He and his brother John Ackerly, cofounder and CEO, started talking in 2008 about issues that Virtru now addresses. John comes from a policy perspective; dealing with privacy issues pre- and post-9/11. Will worked for the NSA.
  • Mike Baird, founder and CEO of Reston, Va.-based Avizia, officially incorporated Avizia in April of 2013. But the company itself had its roots long before that. “Many of us were at a company called Tandberg, a little Norwegian company that was the world leader in videoconferencing,” Baird said. After Cisco Systems acquired Tandberg five years ago, Baird took over the small group and spent three years working under Cisco’s corporate umbrella, “building the team, building some products and building something interesting,” he said. “But I saw a window of opportunity. We approached Cisco and negotiated a deal to spin this out as a new entity.” And thus, Avizia was born.

Question 2: How flexible are you? Are you willing to do the things you aren’t supposed to be good at?

  • Entrepreneurs who are succeeding are those who appreciate and do the things they aren’t “supposed” to be good at. As Dr. Glen Coppersmith, founder and CEO of Crownsville, Md.-based Qntfy, a mental health analytics company, said, “I strongly suspect that the vast majority of our time and effort is going to be figuring out what … works within mental health, and then at some point we will have to do some quant stuff and build things. But the vast majority of this problem is actually figuring out how the tech fits into the larger human system.” For a quantitative team full of tech know-how and advanced degrees, the empathy and selling are the tough parts that Glen has had to master as he builds a promising company.

Question 3: Are you in the right location to launch your business?

  • Many people have a kneejerk reaction about where to start certain types of companies, particularly tech companies. However, the type of talent pool in various cities can provide asymmetric value. For Ackerly, of Virtru, there was no question of what city is best to build his security technology company. He said, “When it comes particularly to security, I think D.C. has a huge advantage over anywhere else. There are a lot of companies here who have a lot of engineers who really understand their stuff.” The deep talent pool plus the difference in the competition and thus bidding up of compensation, has helped Virtru build a solution that is quietly growing rapidly away from the spotlight.

Question 4: Can you put the pieces of your background to work for you? 

  • Are you trying to run away from your past experiences that you are wearing the founder hat? Don’t. You need to use your background as a strategic enabler.
  • Baird, of Avizia, saw great companies renowned for their culture, like Southwest Airlines, up close as a management consultant. He made sure to over-index on culture and scalable management, which has allowed Avizia to grow quickly yet sustainably.
  • Donna Khalife, founder and CEO of downtown D.C.-based Surprise Ride, put both sides of her career to work as an entrepreneur. Donna was an investment banker right out of college for a few years. For the quantitative side of Surprise Ride, this is a necessity. Clearly, though, Donna relies on her time as an actress in Los Angeles for the aspects of her job that require her to be on stage — like pitching investors or strategic partners, or of course during her star turn on ABC’s Shark Tank.

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