Mirror Mirror on the Wall, Who’s the Fairest Co-founder of them all?

It was 2007 — with a freshly inked business degree hanging proudly on my wall, an empty 600 square-foot office space surrounding me, and a stack of resumes 3 inches thick, I sat back in my gray telescopic chair, fumbling through the first dozen resumes, each one looking identical to the last; “Lead Developer”, “Experienced Developer”, “Advanced Developer”, a singular resounding thought echoed in my mind, “How the hell am I going to find my guy?” 

Every leader I’d ever read about, or heard speak, always said “Hire the best people”, “Every company boils down to their people, hire A+ people because A+ people will eventually hire A people, and A people will eventually hire A- people”, they’d forewarn, as if there was some letter grade posted on the front of every resume.

Well, what does that even look like? There must be some imaginary ranking system that measures one person against the rest and labels them an “A+” I thought, right? As I continued flipping through the stack of resumes, they seemed to blend into one; one big confusing decision to make. I needed a Technical Co-Founder, and I needed my A+ hire, but the process was entirely overwhelming for a 22-year old.

When I eventually interviewed Terry, the lead developer that I hired to build the Beta website for WorldMusicLink, he not only looked different from me, he sounded different from the rest. Sure we were over 50 years apart in age, me 22, him in his mid 70s, but that wasn’t what made us different.

Terry had over five decades in the corporate world. He had battle-scars from startups gone belly-up. He had seen the promise land that startups yearn to conquer, and in most cases, had never reached. That knowledge — of failure — was invaluable to me. For failure, was my single greatest fear. Terry had developed a calm in the face of uncertainty, of startup insolvency, and had learned to persevere despite past failed attempts at success. I had no such comprehension of what the battle would truly look like, as I had only read about it in books, listened to successful entrepreneurs boast of their triumphs, yet I knew that I needed to surround myself with a technical co-founding team member who had tasted defeat, and had battled on. He would not make the same mistakes twice. He would not run away at the first sign of a missed paycheck. Terry still had faith in dreamers like myself — to change the world with our ideas. Yet he also possessed a priceless knowledge of the arduous journey ahead. I hired Terry for his technical skills, but moreover, his battle-tested wisdom.

If you want another ‘you’ on your team, then look into a mirror and keep dreaming. People who are just like us — they dream like us, they think like us, they act like us, they work like us, they have the same skills as us — work up to a certain point. These kinds of people are really attractive early on in a startup (around ideation and launch), because there’s no conflict of opinion, they’re on the same page with your ideas, and they work well in developing the initial product. But, that’s where they stop functioning so well it turns out.

If you’re like me, you hate conflict and love when people agree with you. The big issue with that is, if you are pursuing something worth pursuing, you need both someone who can see the dream, but also challenge you and push back at various stages of the game. You need someone who has some overlap in skills so you can systematically execute on goals, but also someone who has complimentary skills that ripen over time and can become the Ying to your startup Yang.

Reid Hoffman, Co-founder of LinkedIn® and Partner at Greylock, says “[Early on] Startups need Generalists” — people who can wear all of the hats, as the needs crop up. “[As the company scales], Specialists are needed”. That’s why a Technically minded Co-founder and a Generalist Marketing/Managerial Type work well together in a founding team on a software startup. That’s why a seasoned Chef and a Creative Manager work well to launch new Restaurants. That’s why a creative, introverted Designer works well with an extroverted, passionate Operationalist.

You need complimentary, not replicative skillsets in a Cofounder. Someone who pushes back when you ardently press forward. A specialist when the micro needs fixing. A generalist when the macro demands a pivot. And, an ethically-driven leader no matter what the situation calls for. Easy to find? Hardly. Worth the wait for the right fit? Definitely.