Entrepreneurial Leaders are Contrarians at Heart

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 after raising money on KickStarter. The last is several years into bootstrapping a SAAS platform; his team has achieved product-market fit and is scaling. All of them said they’d been working 80+ hour weeks as they worked to grow their business. All four were incredibly hard workers, and they were all so smart.

Yet, even in our discussion, they approached things from wildly different perspectives. The founder of the 20-person software company, proclaimed “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% 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 (which 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. Essentially, they see opportunities that others have overlooked. They must balance the confidence to pursue those opportunities with the humility to learn about their market. They must be masters of change, because running a one-person show is different than running a 10-person show which is different than running a 100-person show.

When you see it in this light, it’s not surprising that the panelist whose company is pre-launch announced he would only create an absolutely perfect product and 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. Successful entrepreneurs learn when to be where.