Should I Stay or Should I Go?
“Should I stay or should I go?”
I've been asked for advice on that question a lot in 2024 by friends in the tech startup space.
It's a weird time for startups. There are a bunch of companies that raised monster growth rounds at wildly inflated valuations in the ZIRP era, and are now struggling along. Will they recover and become profitable, sustainable growth companies? How long will that journey take, and is there something interesting on the other side?
Meanwhile, action shifted to seed stage fundraising, but those same companies are finding Series A rounds much harder to come by. Once again, the question is time. How long will it take to breakthrough? How much time, as an employee, are you willing to invest?
No wonder so many people are asking "should I stay or should I go?"
It's also a question I've asked myself multiple times over the last twenty years. I answer it with four more questions, three required and one optional:
Am I growing?
This is not about career trajectory and certainly not about a title. Quite simply, am I developing new skills that (a) I find personally fulfilling or wildly interesting and/or (b) that will make me more valuable in the future?
Do I respect the people I work with?
Respect, not like. Liking my colleagues is always a bonus, and a delightful one. I've forged some of my most enduring friendships in the fire of the startup kiln. But, it's not a critical stay-or-go factor. It's a nice to have.
By respect, I mean believing that person is excellent at their craft. That they have some super power (or powers) that you're in awe of and wish you could emulate. It doesn't have to be a classic tech bro super power, like sleeping two hours a night or breaking into unexpected messianic monologues. It could be something like the ability to form deep human to human connections almost instantly. Or enthralling story telling skills. Or genius level depth of knowledge in the field the startup is operating in.
This applies 10x for founders. If you don't respect the founder, if they're not super powered in some way - leave.
Do I believe in the product?
Anyone who is bought into the company and its future will tell you to believe, and tell you why to believe, and that's infectious. But YOU have to believe. You can believe exactly the story that is being told, wholeheartedly, and that's good enough to stay. But ideally you also see something extra, something you could add to the product and its trajectory, that makes you deeply convicted that there is a winning outcome in the future.
Is there a realistic wealth creation opportunity on the horizon?
This is the optional one, simply because everyone relates to money and wealth differently. For some it is the thing, and for others it's just a by product. Everything in that range is all good.
For me, wealth creation always mattered, and still matters. One, because I derive a sense of security and freedom from having money that's deeply important to me (for reasons we don't need to dive into here). Two, because I think it makes startups way more fun, because you're essentially doing what you love while gambling with your time!
But gamble smart. What you stake when you join a startup in exchange for equity compensation is your time, of which you have a finite amount.
Sometimes the external macro environment shifts radically (exiting the ZIRP era, for example) and what was a smart gamble needs to be re-evaluated.
I would regularly reassess (at least annually, and at any major event - fundraising, external shock, etc) what I forecasted my equity to be worth, to see if the calculated bet still made sense. To do that with any reasonable accuracy, you typically need to know:
your share count and vesting schedule
fully diluted shares outstanding
total amount raised and liquidation preferences for investors
amount raised at last round, valuation, and top line revenue when raised (to get a rough multiple)
current industry revenue multiples
It's not an exact science by any means, but you can use those inputs to get a range of possible realistic outcomes for your shares, across different time horizons. For me, if most scenarios cleared my minimum wealth creation bar for that tour of duty, then good to go. If most scenarios fell below that, time to ask myself some hard questions.
Interestingly enough - these are the exact same questions you should be asking yourself when you're interviewing somewhere new! If you can't emphatically say yes to all these questions at the end of an interview process, ask more questions. If you can't get comfortable - if you're talking yourself into it or giving yourself a pass on one of these four questions - don't take the job.
Otherwise you'll soon find yourself asking again - should I stay or should I go?
