The Decision That Made Everyone Think He Was Crazy
In early 2019, Daniel Vassallo did something that made everyone question his sanity. He walked away from a $511,000 annual salary at Amazon.
Not because he was burned out. Not because he hated his job. Not because he'd been treated poorly.
He left because every promotion felt hollow within a week. Hitting $100K, then $200K, then $500K brought the same fleeting dopamine rush that wore off just as quickly. Chasing external validation was a treadmill that would never satisfy him.
"I would be delusional to think that earning $1M, or $10M would suddenly make it different," Vassallo wrote in his now-famous blog post.
For eight years at Amazon, he had been the model employee. He joined as an entry-level developer and rocketed up the ranks, earning two promotions in his first 3.5 years. A third promotion was practically guaranteed. His work-life balance was solid. His reputation was sterling. He was leading the most important project in his department's history.
By every conventional metric, he had won the game.
But winning didn't feel like winning anymore.
The Trap of Freedom Lost
What Vassallo discovered was something many high-achievers learn too late: success in a corporate structure comes with an invisible price tag.
In his early years at Amazon, motivation was off the charts. He worked with one other person on an internal tool with minimal oversight. They decided what to work on, how to do it, and when to ship. The freedom was intoxicating.
But as his career progressed, that freedom evaporated. More stakeholders meant more opinions. More responsibilities meant less autonomy. Complex politics replaced simple problems. He was always working on somebody else's terms.
The final straw wasn't a specific incident. It was a simple thought experiment: "What kind of work would I do if I had to do it forever?"
The answer wasn't what he was doing at Amazon.
So with $1 million in liquid savings, enough to fund five years of expenses, Vassallo took the leap. He quit with no concrete business plan, no safety net, and no guarantee of success.
What happened next would redefine how thousands of entrepreneurs think about building businesses.
The Philosophy That Changed Everything
Vassallo's first move after leaving Amazon was typical: he started building a SaaS product called Userbase, a tool for creating secure, encrypted web applications.
Six months in, reality hit. Despite a strong launch, Userbase was generating minimal revenue. His runway was limited. Anxiety spiked.
Most founders double down, burning through savings while hoping for a breakthrough. Vassallo did the opposite.
He reframed his goal from "build a billion-dollar company" to "remain self-employed." With that shift came a radical new strategy: small bets.
Instead of spending months building one ambitious project, create many small, quick projects with minimal time investment, low downside if they fail, high potential upside if they succeed, and the ability to stack on top of each other.
Think of it as venture capital applied to personal projects. VCs make many bets knowing one big winner can cover all the losses. Vassallo applied the same logic to his work.
His first small bet came from a simple observation: he'd spent years at Amazon working with AWS. Why not share what he knew?
In under a month, he wrote a 173-page ebook with former colleague Josh Pschorr called "The Good Parts of AWS." No fancy production. Just a straightforward brain dump of everything he'd learned.
He priced it at $65 and launched Christmas Day, 2019. Within 14 days, it made $45,000. Total earnings would eventually exceed $140,000 from over 7,800 sales.
The entire project took about 160 hours.
The $3.6 Million Exit
In April 2024, Gumroad approached Vassallo with an acquisition offer for Small Bets. They had already purchased 10% for $500,000 a year earlier. Now they wanted the remaining 90%.
The deal aligned perfectly with his philosophy: $3.6 million total, split evenly between cash and stock options vesting over five years. Vassallo continues running Small Bets for five years. If he quits early, he forfeits unvested options.
At an 8X profit multiple based on 2024 earnings, it was a solid exit. More importantly, he maintained control, stayed self-employed, and positioned himself to benefit if Gumroad grows further.
From walking away from $500K in 2019 to a $3.6M exit in 2024, all while maintaining the lifestyle freedom he had originally sought.
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Building the Portfolio
As Vassallo's Twitter following exploded from 150 to 24,000 followers in 14 months, people kept asking how he'd done it with zero marketing background.
So he created another small bet: a 100-minute video course called "Everyone Can Build a Twitter Audience." He announced it to his 880-person email list and Twitter followers. Four hours later, he'd sold 100 copies for $6,358. That course eventually generated over $310,000 from 13,000+ sales on just 16 hours of work.
In 2021, he launched a cohort-based course teaching the small bets philosophy. To skip tedious introductions, he set up a Discord server for participants. Something unexpected happened: the community became more valuable than the course itself. Members kept returning to share ideas, ask questions, and support each other's projects.
Vassallo pivoted reframing the offering from "course with community access" to "community membership with course included," switching to open enrollment with a one-time lifetime fee. The Small Bets community was born.
Results from November 2021 to October 2023: $824,409 in revenue, $601,895 in profit, 41 consecutive cash-flow positive months, and over 6,800 lifetime members building a thriving ecosystem together.
The Lessons That Matter
Vassallo's journey offers a masterclass in thinking differently about risk, value, and success:
Intrinsic motivation outlasts extrinsic rewards. Promotions feel good for a week. The work you'd do even if no one was watching never gets old.
Success is unpredictable, so control what you can. You can't predict which project will succeed. But you can control how much time you invest before finding out. Small bets limit downside while maintaining upside.
Freedom is worth more than money, to a point. Vassallo isn't anti-money. He saved aggressively and took calculated risks. But he understood that beyond a certain threshold, more money doesn't buy more happiness. More freedom does.
Credibility compounds. His AWS book worked because of eight years at Amazon. His Twitter course worked because he'd built a real audience. Each bet built on the previous ones.
Diversify before you need to. When Userbase stalled, Vassallo didn't panic. He added more bets to his portfolio, giving him options and removing the desperation that kills most solo ventures.
Community beats courses. His most valuable asset wasn't information products. It was the network of people helping each other implement what they'd learned.
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The Philosophy Lives On
Today, Vassallo continues running Small Bets under the Gumroad umbrella, helping thousands of entrepreneurs think in small bets rather than huge moonshots. His Twitter following has grown to over 160,000. His portfolio of products generates income with minimal ongoing effort.
He's not building the next unicorn startup. He's not trying to 10X his net worth every year. He's not working 80-hour weeks or raising venture capital.
He's doing work that matters to him, on his own terms, with the freedom to spend time with his family in Seattle.
Vassallo has shown thousands that there's an alternative to the "all-in on one big bet" approach. You don't need to risk everything to win. You just need to place many small, smart bets and let the winners compound.
In a world obsessed with unicorns and billion-dollar exits, he proved that sometimes the smartest move is to think smaller, bet often, and design your life around what actually makes you happy.
Not what makes investors happy. Not what impresses LinkedIn. Not what generates headlines.
What makes you happy.
That's the real fortune Vassallo walked away from Amazon to find. Six years later, it's clear he found it.
The Bottom Line
Vassallo didn't quit a $500K job to get rich. He quit to reclaim his freedom. By placing many small bets instead of one massive gamble, he built a portfolio worth millions while keeping his autonomy. You don't need a unicorn to win. You just need enough small wins to design the life you want.