by Zach Clayton ’07

I hosted a panel this weekend with four great entrepreneurs who are at various stages of building a business. One is a former senior executive at a Fortune 50 company. Another works at the $5 billion “unicorn” Stripe, while another is launching his product shortly after raising money on KickStarter. The last is several years into bootstrapping a SAAS platform, and his team has achieved product-market fit and they’re now scaling.

All of them said they had been working 80+ hour weeks as they worked to grow their businesses.


They all were so smart. Yet even in our discussion they approached things from such different perspectives. The founder of the twenty person software company proclaimed that, “time is everything—you must only focus on one thing and apply all your time and energy to achieving it.” The entrepreneur from Stripe talked about how they were broadening their focus from payments to infrastructure—essentially trying many, many things.

Who was right? Both of them.

Entrepreneurship is about matching your resources (your capital, team, expertise) with your market (what customers want) and your moment (whether you are early or late). Sometimes you need to broaden your view. Arguably, 100 percent of failed businesses should have pivoted at some point prior to their failure. Other times you need to focus. I heard Joe Colopy of Bronto recently talk about the fact that his company (recently sold for $200 million) only started to get momentum when he dramatically narrowed the product vision.


I believe great entrepreneurs are contrarians at heart. They essentially see opportunities that others have overlooked. They must balance confidence to pursue the opportunity with humility to learn about their market. They must be masters of change, because running a one-person show is different than running a ten-person show which is different than running a hundred-person show.

From that lens, it is not surprising that the panelist whose company is pre-launch announced he would only create an absolutely perfect product and would accept nothing less. Meanwhile, I recall Jesse Lipson of ShareFile (which now has more than 500 employees) once coaching me that I had to let go of perfectionism if I was going to actually scale into the CEO role as Three Ships was growing. Again, who is right? Perhaps both are. The resources, market, and moment vary.

So perhaps the secret of great entrepreneurs is that they are capable of answering, “What is needed now?” They know their customer, they know their moment, and they know themselves.

They know when to be where.

Zach Clayton is the founder of Three Ships, a digital marketing company based in Raleigh, North Carolina. He wrote the post above after reflecting on his experience moderating a panel about entrepreneurship at the seventh triennial Morehead-Cain Alumni Forum.