In my work as an investor with Sequoia and Propeller, many CEOs pick my brain about the journey from startup founder to scaleup CEO.  It was inde

A Startup Founder To Scaleup CEO’s Journey from $0 to $25billion (Halliganism’s)

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2024-10-01 23:30:02

In my work as an investor with Sequoia and Propeller, many CEOs pick my brain about the journey from startup founder to scaleup CEO.  It was indeed a long strange trip, but one on which I learned a lot.  Here’s a list of Halliganism’s I picked up along the way that I hope will help some of you on that same journey.

Perspiration vs Inspiration: In startup mode, the CEO role is 90% perspiration and 10% inspiration. In scaleup mode, the CEO role is 10% perspiration and 90% inspiration. What worked in startup mode won’t necessarily work in scaleup mode—you’ll need to evolve.

1 back, 2 forward, 1 back, 2 forward: From the outside, HubSpot might seem like a smooth up-and-to-the-right story. It belies what actually goes on inside. The best way I’d describe HubSpot is two steps forward followed by one step back followed by two steps forward followed by one step back over and over. We never found that “silver bullet.” There was never one hire, one customer, one partner or one investor that moved us forward more than two steps. It’s a grind.

A perpetual state of constructive dissatisfaction: This is how one of my board members, Lorrie Norrington, described me once. I kind of liked it.

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