A successor for Steve Jobs?

By Chris Combette

 “Sculley believed in keeping people happy and worrying about relationships. Steve didn’t give a shit about that. But he did care about the product in a way that Sculley never could, and he was able to avoid having too many bozos working at Apple by insulting anyone who wasn’t an A player”

        Allan Alcorn, former co-worker of Steve Jobs at Atari

“Rough-edged”, “immature”, “management by character assassination”: all described Steve Jobs’ management style in his biography. As we went through the Cloudflare case, detailing the stories of burned-out employees giving up some of the most sought after equity in Silicon Valley only weeks before vesting, I couldn’t help think about the most famous visionary genius in recent history: Steve Jobs. With its tremendous initial success (30 000 new users a day, etc…), huge market opportunity, innovative products, Cloudflare seems to be on the same track as early stage Apple. But the resemblance is even more striking when studying the impact of their respective founders on the company cultures.

We don't have a lot of process at Apple, but that's one of the few things we do just to all stay on the same page”[1] used to say Steve Jobs. With his blatant disregard for processes or even the HR department, Matthew Prince sounds like he is reading from an early stage-Apple management textbook. Additionally, with a polarizing personality, a passion for his product / company and an exclusive focus on his company (recall his quote: “Not having time for friends and loved ones is no big deal for me, because I don’t have any”?), Matthew Prince further resembles young Jobs. One might ask the question: will he survive CloudFlare’s scaling phase or will he suffer a Jobs-like destiny when he was forced out of Apple by John Sculley?

As a startup begins scaling, management and the board need to move away from the lack of organization that made their success at the beginning. Indeed, while reactivity and short leadtimes to pivot, adapt and change are key before the product-market fit milestone, a larger organization requires accountability and thus specialization. With that usually come, organizational charts and associated processes that Matthew seems to refuse. I am surprised that Cloudflare’s board does not encourage Matthew and Michelle to anticipate these organizational needs rather than letting them wait for errors to force them to do it later down the road.

In addition, with a growing organization, founders’ equation requires satisfying a larger number of variables: more employees, more investors with larger investments at risk, more customers, etc…While finding the perfect fit for all of these parties might have been feasible at a small scale, it is almost impossible after a while if the founder is too polarizing. As long as CloudFlare is following a smooth hockey stick growth, Matthew shouldn’t worry too much about his role. However, every road bump on the road might shed more light on his management practices and increase likelihood of a replacement. Although visionary and brilliant at product design, failing to adapt his management practices, organization and processes is a risky bet for Matthew Prince. If Steve Jobs got replaced, it can also happen to him…



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