Hail to the anti-serial entrepreneur
HubSpot CEO Brian Halligan was the kick-off keynote speaker for Underscore Venture’s second annual Core event yesterday. Brian’s brand of “funny, honest, and self-deprecating” was in full and attractive bloom. But the most refreshing part of Brian’s fireside chat was his claiming that, at age fifty and ten years into this venture, HubSpot is his job for life. Why did that make me smile? In today’s entrepreneurial culture we celebrate the quick wins; to build a business for the ages is unusual and special.
“Serial entrepreneurs” claim that identity with pride. That pattern of starting multiple ventures can yield a lot of wonderful learnings and outcomes, but it generally means moving through a bunch of serial failures. I’m not being judgy. Serial failures can teach a founder a whole host of lessons that lead to an ultimately solid and even spectacular business. But in terms of economic impact and job creation, a serial entrepreneur may just be a blip on the landscape—for a very long time. A founder who commits to sticking with their venture and seeing it through to becoming what Brian calls a “pillar company” is far more rare.
It’s not the least bit surprising that founders move on. People who create a company are not always the people who also want to build one. It takes guts and humility for a founder to cede the reigns when their interest or skills are outpaced by the business. On the flip side, sticking with it takes walking through the fallow periods of stasis or unexpected challenge or embarrassing failure. Brian says HubSpot has always been like “two steps forward and one step back.”
To stay the course, through all the hard and necessary personal and professional growth to scale as business and as a CEO—that is remarkable and excruciatingly difficult. (And at least when it comes to the difficulty part, I can relate.) When an audience member asked how Brian’s CEO job changed over the last ten years, he reached to his back pocket and pulled out a folded and dog-eared 30-page document that was the report from his recent 360 degree review. He admitted to having “high beta”–or great strengths equally matched by great weaknesses–and he was clearly using the internal feedback to get to the next level in his CEO role.
Kudos to Brian for being a role model. His public commitment gave me energy and it sent a signal to all the budding entrepreneurs in the room that the successful founder path need not be a “flip or flop” one. It can be enduring, sustaining, and long.
Jules Pieri 
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