Humans are remarkably great at revisionist history. Business is no exception. When I discuss a startup or growth company’s future prospects, my crystal ball is typically cloudy. And it’s cloudier the closer I am to the operations and execution of the organization. It’s easier to prognosticate positively about a competitor when you only see their good press and growth rates from the outside.

Patrick Collison once said at a Stripe all-hands, “We live our self-doubt.”

On the inside, the likelihood of negative events feels higher than positive ones. This is probably because negative events occur easily through inertia and complacency while positive breaks require tremendous effort to inflect the business.

Looking forward, it feels like we as employees are the Time Variance Authority working to ensure that the timeline of the company stays on the best, predictable path. We work to cleave branches that threaten to destabilize our trajectory.

Retrospectively, the timeline followed feels self-evident. All the branches that could have been are cleaved and the narrative is set. Of course we ended up here, that’s where we are.

This comes up from time-to-time with former coworkers from Duo Security. Cisco acquired Duo in 2018 for $2.35B. This was undeniably a great result.

One of the former Duo executives likes to quip along the lines of “Yes, and we could have done a lot better if we had been more disciplined.”

I’m not so sure about that. It’s hard to know prospectively which ideas may lead to the next $100M in ARR. And I’ve been skeptical of enough ideas that do so to remain skeptical of my own predictive abilities.

Conversely, there were a lot of paths that might have been worse than the result Duo arrived at. Nation state adversaries were constantly trying to breach Duo and compromise customers’ authentication systems. Attacker luck or a simple error like an employee getting phished may have led to this. For a security company whose sole purpose is protecting customers, that’s game over and would decimate the company’s value.

About a year before the Cisco acquisition Duo was in the process of being acquired by another MegaCorp for just under $1B. A signed term sheet and everything. Just before close, the acquirer pulled out. It felt devastating at the time, like we’d peaked. Duo instead raised $70M and just 12 months later was acquired for >2x those terms. Not a bad ROI for a year’s time.

There’s a reason that one of Stripe’s Operating Principles was once: We Haven’t Won Yet.

It’s easy to revise the narrative of what occurred; fortune telling forward is far more fraught with peril.

Avoid complacency and stay diligent.