Calling Startup Cornerman

“Float like a butterfly, Sting like a bee, your hands can’t hit, what your eyes can’t see.”

—Drew “Bundini” Brown

Muhammad Ali’s most famous quotation was not authored by the champ himself. Rather, the memorably iconic description was penned by his long-time cornerman Drew Brown — his coach, trainer, advisor, and therapist. He wipes off sweat and cleans up blood. He offers simple advice for the next bruising round of competition. Often cornermen are former fighters. Many coaches once played the sports they now teach.

That’s why I became, to my knowledge, the first professor of Internet history. I wanted to coach and teach future entrepreneurs. I didn’t complete a PHD to earn my right to teach. I started a bunch of companies and had an uninterrupted front row seat to the rise of the digital revolution. But I was lonely as a CEO and longed for a cornerman. Later, in preparing my syllabus on Internet history, I learned that Google’s founders had their own cornerman.

The late Bill Campbell, once the chairman of Intuit, rolled up his sleeves in Google’s C-Suite during the aughts. The Googlers called him coach because Campbell had once coached the Columbia University Football Team. Brian Chesky (CEO AirBnB) has created a particularly powerful reciprocal mentorship with John Donahoe (CEO Ebay). Both Google and AirBnB were dramatically scaling by the times their coaching relationships began. They had achieved the holy grail of startup survival that Mark Andreessen has coined “product/market fit” defined as measurable, sustainable organic growth. As Mark observed, there are two key early stages for startups. Before Product/Market Fit and Growth. Each stage has challenges related to prioritization, focus, personnel decisions, fundraising, and board management. It’s a lonely process and it’s good to have a cornerman.

Exceptional venture capitalists work hard to play this role and some find ways to be enormously helpful. But for the most part investors, must by nature of the job be much more macro-economically focused. They build portfolios, manage limited partners, and invest considerable energy sourcing and evaluating investments. There are structural reasons why investors struggle to be cornermen.

  • Investors are helpful recruiters, but it’s extremely unusual for them to get in the trenches on a day to day basis. Time constraints do not allow it. . Two case study exceptions to this rule would be John Doerr at Go Computing and Roelof Botha at YouTube, but I suspect even those men would say these were rare events over the course of their careers.
  • Union Square Ventures has a deservedly very fine reputation. But incentives between individual CEOs and firms are not perfectly aligned. As an example, I’m certain the entire USV partnership wants Code Academy to be enormously successful, but if Diwolla, Etsy, Kickstarter, Meetup, or Kik can be the next unicorn, their business model remains intact. They can afford the occasional Hashable or
  • Firms spread resources across many companies because they manage portfolios as an asset class. Entrepreneurs build and operate businesses. Sometimes investors have to invest more time with their winners and that makes it hard to be a good cornerman to the whole portfolio.
  • Few venture capitalists have been CEOs or operating executives. That’s the principal reason Mark Andreessen and Ben Horowitz can reinvent the venture model by staffing their firm so differently. Bill Gurley, Mary Meeker, and Fred Wilson, 3 of my intellectual heroes of the digital age have deeply influenced how I think about the tech industry and Internet history, but they never ran startups. Reid Hoffman, Mark Suster, Chris Dixon, Josh Kopelman, and Jeff Bussgang, are different from most of their colleagues within their own firms. Many people don’t remember that Vinod Khosla co-founded Sun Microsystems, long before his hall of fame venture capital career.

I’ve been a decent Internet executive with four exits, two failures, and 2 still TBD. My tenure as an Internet CEO reminds me Oakland A’s General Manager Billy Beane’s playing career. Beane, the hero of Michael LewisMoneyball, was an accomplished 5-tool athlete. But the second baseman never quite lived up to expectations as a baseball all-star. He was a good, not great major league player. His most impressive achievements blossomed later when when he discovered a new method of identifying and nurturing baseball talent. Today he remains the exceptional general manager and CEO of the Oakland Athletics. I was a decent CEO, but nowhere close to LinkedIn and Paypal MVP Reid Hoffman — the digital revolution’s Willie Mays.

Running startups is brutally difficult. Challenges abound and board members (corporate or advisory) don’t have the available time to roll up their sleeves. Cornermen whiteboard, sell, cheerlead, debate, cajole, and do whatever they can to help companies.

As an industry, we can do more to support the entrepreneurs who are changing the world. We can do even more to be in their corners.