Most people answer that question with a spreadsheet in their head — weighing the risk of joining something that might not exist in eighteen months against the slim chance of a life-changing windfall. Both halves of that calculation are real. Both, I'll argue, are beside the point.
Start with the windfall, because it's the part everyone fixates on.
On its market debut a few weeks back, SpaceX was widely reported to have created some 4,400 millionaires overnight. The New York Times told the story of Trevor Hise, who joined SpaceX in 2011 — choosing it over what his parents saw as a more stable job at General Electric. Over twelve years there he accumulated more than 100,000 shares. By the June 2026 listing, at $135 a share, those holdings were worth roughly $13.5 million.
"The magnitude of this has been ridiculous," he told the Times.
He could contemplate stepping away barely a decade into his career.
The Odds, Soberly
Not all startup stories end this way.
The popular line that "90% of startups fail in the first year" is a myth. According to U.S. Bureau of Labor Statistics data, about 20% of businesses fail in their first year, just under half within five years, and roughly 65% within ten.
Better odds than the folklore suggests — but sobering all the same. And that's before we narrow from "all businesses" down to the far riskier subset of venture-style startups chasing outsized growth.
So while the possibility of striking it rich is real, the odds are against it — and it shouldn't be the reason you join.
Justin Kan, of Justin.tv fame, made exactly this point at a Y Combinator event years back. If a quick path to extraordinary wealth is what you're after, you probably should not join a startup.
What You Give Up
Startups are not havens of stability. If you want a perfectly tailored five-year career plan, you won't get it at a startup.
Nor are they perfectly curated workspaces. The sign on the door reading "nine-to-five" is usually just that — a sign on a door. Early employees work late, wear several hats, and figure things out as they go.
But here, in South Africa, the conventional wisdom needs a second look.
The advice to "play it safe" assumes there's a safe option to play — a stable job quietly waiting as the sensible default. For most South Africans, that assumption no longer holds.
Official unemployment sits at 32.7% — roughly one in three working-age adults who want a job can't find one. For those aged 15 to 34, it's closer to 46%.
A "stable" salaried position isn't the floor beneath the startup gamble. It's itself an increasingly scarce and uncertain prize.
That changes the calculation. When secure employment is abundant, joining a startup means trading safety for upside. But when the "stable" job may be a retrenchment letter away regardless of how loyally you serve, the safety you're protecting starts to look like a liability of its own.
Betting on a fixed salary in a shrinking job market is its own form of risk — just a quieter one.
So the question shifts. It's no longer "why take the risk of a startup?" but "given that risk is unavoidable, which kind actually builds something in you?"
Why You Should
Kan offers three reasons.
- You'll get handed work you have no business doing — and that's the point. At a big company, roles are gatekept; you earn the title before you do the job. At a startup, the job arrives first and you grow into it, because there's nobody else. Kan tells of an engineer who, within a year of joining Justin.tv, was running the entire backend of a top-100 website — a job he was, by Kan's own admission, completely unqualified for. That gap between what you're trusted with and what you've proven is where the steepest growth happens.
- A startup is the best on-ramp to building your own. If founding something is on your horizon, there's no better preparation than watching one get built — and broken — up close. You learn what fundraising really looks like, how decisions get made under pressure, where things quietly fall apart. And you end up surrounded by people who want what you want. As Kan relays it: you are the average of your five closest friends. Put yourself among builders, and you start to become one.
- A startup maximises your rate of learning. This is the one that matters most — and here's the part people miss: it holds whether the company soars or sinks. Kan points to the two co-founders of Cruise, the self-driving company GM bought for over a billion dollars. One learned on the way up, teaching himself to architect a system that became one of the largest bandwidth consumers in North America. The other learned on the way down — cutting his teeth negotiating the sale of a failing startup, lessons he'd later apply to a billion-dollar exit. Win or lose, you walk away with something that compounds.
Underneath all three is one idea. Kan closes with a line from YC's Paul Buchheit: it's not your y-intercept that matters, but your slope.
Where you start is largely luck. How fast you climb is the thing worth optimising for — and a startup, for all its chaos, is one of the steepest climbs you can choose. It is the same bet we make in building a craft for the AI age: the work outruns the title on purpose.
So should you join one?
If you want comfort, predictability, and a five-year plan — almost certainly not.
But if you're optimising for slope, for the rate at which you become more capable, then the chaos isn't a bug.
It's the whole reason to walk through the door.
That's the environment we're trying to build at Transformer Business Labs — a Talent Network of builders and operators for the ventures we launch this year, where the work outruns the title on purpose, and there's a sponsored path to Claude Certified Architect Foundations for those on live work with us. If your slope matters more to you than your starting point, we'd like to hear from you → transformer.africa/talent-network.
Sources: SpaceX figures via CNN and The New York Times ($135 IPO price, 12 June 2026; ~4,400 employee millionaires; Trevor Hise). Business failure rates via U.S. Bureau of Labor Statistics, Business Employment Dynamics (≈20% year 1, ≈49% year 5, 65.3% year 10). Unemployment data via Statistics South Africa, Quarterly Labour Force Survey Q1 2026 (official 32.7%; youth 15–34 at 45.8%). Justin Kan's talk: Y Combinator "Work at a Startup" Expo, 2018.