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Originally published by @EXM7777 on X. Tech Twitter preserves the original source alongside this readable edition.
Before you dive in
• Discover how Jack Zhang built Airwallex into an $8B company without quitting his job first—proof that side hustle success requires patience, not desperation.
Best for builders who want practical takeaways. 7 min read.
everyone tells you to quit your job and go all in on your idea...
but i know a guy who built an $8 billion company while keeping a corporate job at first, and then running a coffee import business
the conventional wisdom about side hustles is completely backwards
people think you need to choose between stability and success, that you need to burn the boats, that total commitment is the only path forward
that's not how wealth gets built
Jack Zhang worked as a bank engineer while importing olive oil from Italy, reselling phone cases, flipping real estate, and running trading algorithms on the side
by 29 he had $10 million in the bank and still hadn't quit his job
the company that became Airwallex didn't start because he wanted to be an entrepreneur
it started because his coffee shop couldn't send money overseas without getting blocked for three weeks straight, and he asked himself a simple question: why can't money move as fast as data?
everything you're hearing about “going all in” is killing your chances of building something generational
the problem with desperation
commitment and stupidity look the same from the outside
when you quit your job to build, you lose cash flow to fund experiments, industry knowledge and connections, the ability to take calculated risks, and mental clarity because desperation absolutely kills good decision-making
Jack had ONE thing for him: he worked at a bank while building a payment company, which meant he understood the infrastructure from the inside, saw the problems that billion-dollar companies couldn't fix, and had the runway to experiment without panic
Steve Jobs didn't quit Reed College and immediately start Apple
he dropped out, spent 18 months traveling India, worked at Atari, sat in on calligraphy classes, and let ideas simmer while he still had income
the side hustle isn't your backup plan, it's your testing ground
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Naval put it this way: “Arm yourself with specific knowledge, accountability, and leverage. The internet has massively broadened the possible space of careers. Most people haven't figured this out yet.”
that specific knowledge comes from working where you can see problems worth solving
the framework
stack advantages, don't split focus
your day job should feed your side hustle, not compete with it
Jack worked in banking which meant he understood cross-border payments better than anyone trying to break in from the outside
and we’re not talking about “work-life balance” here, we’re talking about strategic positioning where your job becomes your unfair advantage instead of your enemy
you're getting paid to learn what you need to know
people think they need to quit to focus, but that's the wrong mindset because you need to work where you can learn what’s important
run multiple small bets
Jack didn't pick one idea and go all in
he ran trading algorithms, imported Italian olive oil, resold phone cases, flipped real estate
some stayed small, others failed completely
each one taught him something about customer acquisition, international logistics, where payment processing breaks down, and what problems are expensive enough that people will pay to solve them
then one day his coffee shop tried to send money overseas, the payment got blocked for three weeks, and that's when the real idea showed up
he didn't start Airwallex because he read a trend report
he started it because he was personally pissed off at a real problem
Elon Musk sold Zip2 for $307 million, started X.com (an online bank that merged with Confinity and became PayPal), got ousted as CEO but walked away with $180 million when eBay bought it, then used that money to start SpaceX and invest in Tesla
he didn't bet everything on one idea, he stacked wins and kept moving
wait for the real problem
the best businesses don't come from “I think people might want this”
they come from “I'm paying for this broken solution and I hate it”
Jack wasn't trying to be an entrepreneur, he was trying to fix something that cost him time and money
when you've felt the pain yourself, you know exactly what the problem is, how much it costs, what a real solution looks like, and whether people will pay for it
stop looking for business ideas
start paying attention to what's costing you money
build while you have resources
Stripe offered to acquire Airwallex for $1.2 billion when they only had $2M in revenue
that's a 600x multiple, and Jack would've made over $2 billion personally
the team said no
Patrick Collison told him something during their conversations: “I'm building Stripe for the next 20, 30, 40 years”
Jack realized that's what he wanted too
you can only make that decision when you're not desperate, when you have runway, when you're not bleeding cash because you quit your job too early
patience is a superpower, but you need income to afford it
the near-death moments
it wasn't smooth
Jack and his team almost died three times building Airwallex
in 2016, they signed a term sheet with a VC who called back one week later to say “I don't think this algorithm thing will work, we're pulling out” and they almost ran out of money completely
external funding creates external timelines, and when someone else controls your runway, they control your decisions
in 2017, they raised a Series A from Mastercard and Tencent, built the entire product specifically for them, and when they launched those companies delivered less than 1% of what they promised
don't build your business on someone else's promises because your revenue needs to come from customers who pay, not partnerships that might scale
in 2020, they were closing their Series D when COVID hit and the US stock market crashed 30% in a single week
their revenue dropped 40% overnight as tuition customers and travel customers vanished
they stopped “almost dying” after 2021
from there, revenue went from $100M ARR to $1B ARR in just four years as they grew their teams, moved into North America and Europe, and turned their infrastructure into software
why did they survive?
they had built the foundation properly from the beginning with multiple revenue streams, global infrastructure, patient capital, and Jack never had to make desperate decisions because he always had options
what this means for you
you're not Jack Zhang
you probably won't build an $8 billion company
but the pattern is exactly the same: keep your income while you build, stack knowledge and advantages from your day job, run multiple small experiments, wait for the real painful problem to reveal itself, and build with patience instead of desperation
the side hustle that becomes millions isn't the one you force, it's the one that solves a problem you're willing to spend years fixing
Jack spent ten years barely posting online, head down building in silence
investors would ask why he didn't tell people what he was building, and his answer was simple: “in Australia, you keep your head down and let the work speak for itself”
being invisible has a price though, because recruiting is harder, customers don't know you exist, and competitors with half your scale get ten times the attention
Airwallex is changing how money moves across borders, processing over $235B in payments annually, and making it possible for businesses to operate globally without the friction that used to kill international expansion
but the product was already built and the revenue was already there before they needed visibility to scale
the people making millions from side hustles aren't the ones shouting about it on day one
they're the ones quietly stacking advantages, learning from their day job, running small experiments, waiting for the problem worth solving, and then building for decades instead of quarters
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