Ask Why It Won’t Work, And Other Lessons For Building From 0 to 1

Rick Song is slightly obsessed with one exercise these days: pre-mortems, or the act of thinking through why a particular strategy, product idea, or candidate might not work out down the line.

This isn’t a typical focus area for founders. In our experience, they’re usually an optimistic bunch, the types who spend time dreaming up big ideas and figuring out how to run through the walls that may stand in their way — more the “move fast and break things” school of thought.

“As humans, we're often more wired to think about things procedurally. X causes Y causal things is just easier for us to work through. And as a result, we tend to think a lot more about the execution of something rather than the concept of it, or how the entire system works together,” says Song.

“But ‘Why would a customer not want this?’ is often a far more interesting question than why they would. When you're working on a product idea, it's really easy to confirmation bias yourself into believing it’s the optimal decision. But once you can also find the counterpoint, the scenario where you’re wrong, you can start teasing out when it would start to make sense — the point at which it will work.”

Song has had plenty of experience with making things work these last few years. Since co-founding Persona in 2018, the CEO has had his hands full with the intricacies of the 0 to 1 phase of company building. (Prior to that, Song spent five years at Square as an engineer and early team member at Square Capital.)

And as Song shared last week in TechCrunch, Persona is at a particularly interesting inflection point — they’ve raised a $50 million Series B and are looking to double their 50-person team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include some big logos like Square, Postmates, and Gusto.

In this exclusive interview, Song takes time to share what he’s learned on his company building journey so far, diving deep into how he brings the pre-mortem mindset to every aspect of running Persona.

Starting with recruiting, he shares the lessons he learned — and had to unlearn — from his time at Square. Next, we chatted about why Song believes it’s not about going down to first principles, but rather studying other companies to find unusual moves and experiment with different strategies and frameworks — of course, questioning why they might not fit your business along the way.

From the strategy behind Persona’s multi-product approach — including a candid discussion about the risks — to why his engineers sell, Song also shares a detailed look at his go-to-market thinking.

Thanks, as always, for reading and sharing!

-The Review editors

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