In March 2023, there was a run on Silicon Valley Bank that erupted over 24 hours. Founders scrambled to get their money out and into a secondary bank account. Some founders didn't have a secondary bank account (bad idea). My friends were in that group. They were in NY when they found out, and had to get their money while they waited for the new account to spin up. What did they do? They went ATM-to-ATM, and — I shit you not — flew back with duffel bags full of cash.
This struck me as… insane? Is that even legal? What if someone stole the money? It's one thing to say to your investors that you lost their money because there was a run on the bank trusted by all startups. It's a whole other thing to say you were flying with duffel bags of cash.
A few months before that, my team (a small startup) was gearing up for a launch. I felt we were too slow and too fast at the same time. The team was pulling nights and weekends and yet we were nowhere near the milestones we wanted to reach. When I met a second-time founder friend, I shared my situation. I asked him how he deals with balancing burnout and shipping at the pace he needed for his startup.
He looked at me like I landed from mars: “Burnout? You worry about burnout after you reach product/market fit.” I felt like an idiot.
This was my first company. As these examples piled over the months, it felt like I was hanging out with a different breed when talking to successful founders. They were street cats: they had a healthy disregard for what’s considered reasonable, they didn’t care at all for creature comforts, and their only concern was the survival of their business.
I, myself, was a house cat.
I spent over a decade in big tech companies before starting my own company. In BigCo you must be civilized. You have to cooperate well, play the politics. You have to be ambitious and drive hard, but not too hard, or you will be considered hard to work with. You have to stay in your lane, work with your functions, manage up, submit TPS reports, and invest in perception management.
What you're getting done is important, of course, but how you're getting it done is equally important. You have to look pretty when you're doing it, otherwise you're toast.
This is house cat territory. Sure, they have to get the occasional rat, but above all they have to be pleasing to the eye, not pee on the floor, and some things will be beneath them.
My de-domestication
Over time, I got in the habit of noticing my house cat behaviors. I was hesitant to assert my point to the designer (“restricts autonomy”). I was reluctant to get into the details in marketing (“what do I know about marketing?”). It took me a month to make an offer (lest there be a mistake), by which point the candidate took another offer. Above all, I winced a little bit every time I pushed the team past their limits. I course-corrected the best I could and often thought “what would a street cat do here?”.
Here's what I figured out so far about the two species:
To a street cat "having bias for action" sounds like "having thirst for water": a tautology too obvious to think about as a special trait.
I make this sound like a dichotomy because it makes it a more fun reading. In reality, most of us are a mix that represents our mix of experiences. Personally, after four years on the street, I still feel like there’s a lot of house left in me.
A street cat in the house
I'll finish with a former manager of mine, we'll call him Nikesh. Nikesh's company was recently acquired, and he joined our BigCo as a Director with the desire to make a big impact.
After our intro meeting, three things were clear to me:
He's absolutely brilliant,
He gets shit done, and
He's in for a world of pain
In his third week, Nikesh picked three battles, one with the design organization, one with a sister team, and one with legal. He was technically right in each one of them, but he was quickly getting a reputation as a bull in a china shop. I tried to gently nudge towards picking his battles— maybe he could start with one, get some wins under his belt, and then continue with the others. He shrugged me off.
As brilliant, dedicated and high-integrity as he was, Nikesh found himself out of the org in three months, and out of the company within six months. Just as the street cat behavior is adaptive for the street, house cat behavior is adaptive for the house: nobody likes a cat marking their territory in their kitchen.
Can’t learn by reading
This lens was helpful in identifying behaviors, and later on, pinpointing candidates that exhibit those tendencies. It accelerated my learning of street cat habits. It also retroactively explained some of the “street cat in the house” behavior that puzzled me during my time at Big Tech.
Being a product manager was a good preparation for being a startup founder. But The Mom Test and Inspired didn’t tell me about duffel bags full of cash. The Hard Thing about Hard Things gave a taste of street cat life, but reading it didn’t prepare me for it — any more than watching Saving Private Ryan would prepare me for trench war. To get street cat skills, the street is where you need to go.
Special thanks to Alejandro with whom we came up with this analogy on a drunken night and Mac, Daniella, Yuval and Murali who read early drafts with helpful comments!
—Iz
Too house for the streets and too street for the house 😆