Big Bets | Jack Danger
A ‘Big Bet’ is a rapid push into a new market space, typically championed by an executive and led by experienced engineers. While the term ‘bet’ suggests a risk, these initiatives often fail and come with hidden costs, like draining morale and neglecting other key products.
I witnessed multiple big bets at Square and had the misfortune of being part of a couple. I worked on the Square Wallet team, which was Square’s first attempt to create a B2C product. Later, I got picked to implement the doomed “Square 275” feature where we charged merchants a flat fee for unlimited credit card processing. Both were big bets mandated by the CEO, bypassing the best practices of product research.
I saw the same pattern at Gusto1 when we tried to expand from B2B into B2C with features that employees would appreciate. My CTO once asked me to lead “Modern Bank”, a flexible payment schedule for employees. I recognized the signs of a big bet and politely declined, exaggerating how much I was needed in my current role.
This is a terrible project to lead. Sure, you might get lucky. More likely you’re about to spend a lot of company money failing directly in front of your executives on something they’re convinved can only fail if the execution sucks. Which is you.
