Product lessons from Cash App and Carbon Health on navigating heavily-regulated spaces

Ayo Omojola, VP of Product at Carbon Health, really knows how to speak our language. While at Square, he picked up the phrase "going unreasonably deep" from Brian Grassadonia, co-creator of the Cash App — and we thought this made for an excellent topic to explore when Omojola stopped by our virtual recording studio for our second-ever episode of In Depth.

Omojola has carved out a niche for himself in product spaces by navigating the often tangled web of heavily-regulated spaces. At Square, he co-created the popular Cash Card (that got people so jazzed that they started sharing their personalized cards on Twitter) and now at Carbon Health he's tackling the challenges of healthcare accessibility, including COVID-19 testing. He's also a former YC-backed founder and active angel investor.

When it comes to creating and launching a product that cuts through the noise, Omojola's got a whole host of wisdom for each step of the process — from zeroing in on your idea, digging into regulation complexities (even when you're not an expert), and collaborating with a team to bring it to life.

A quick aside here: For our inaugural In Depth episode with Lambda School's Molly Graham, we released the podcast episode first and published our long read on the Review a few days later. With our second episode we're trying something different by launching both the podcast episode and our signature-style profile article on the same day. 

No matter how you choose to consume, we think you'll find plenty of lessons from this product vet that will have you reaching for your notebook. What we loved about talking to Ayo is he's got plenty experiences to tap into — from spending (in his estimation) weeks worth of hours at credit card factories, to getting in headed debates about the Durbin Amendment with Square's legal team. But more importantly, he's quick to share the hard-won lessons that shaped each step along the way.

Here's a quick preview of the mountain of advice that's in store:

• Lesson #1: Carefully choose what to work on before you start grinding. "When it comes to a new idea, it’s so much more important to be certain, or as sure as possible, that the questions you’re answering are worth asking to begin with."
• Lesson #2: Find the opportunities where it's easy to stop — and keep going. "Always look for those opportunities where it’s easy to stop, where it gets tedious. That typically is a signal that somebody or a bunch of people just haven’t gotten deeper before."
• Lesson #3: Context is king. "You may save time upfront not taking the time to set context around what you’re trying to achieve, but you’ll more than add that time back on later when things get lost in translation."
• Lesson #4: Hire and manage with the goal of making yourself obsolete. “My first instinct was to believe that I was inefficient, because I got super busy and a bunch of stuff stopped getting done. I figured that I just had to get more efficient and I started trying all these productivity hacks. But looking back, the right answer would have been to replace myself everywhere as early as possible.".

Got some guests in mind you'd love to see us dive deep with? Drop us a line. Thanks, as always, for reading and listening.

-The Review editors

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