scalable type – Cody Berman, the Massachusetts serial entrepreneur behind “Retire by 30,” says his sharpest lessons came from more than 30 side hustles—especially the ones that didn’t work. He credits scalable “type two” income streams for reaching financial independence in h
On a hot. hilly day in Australia. Cody Berman thought he’d found a side hustle that wouldn’t require staring at a computer. Within a month, he was delivering people’s food on a pink, single-speed bike—then watched his ratings slide. “Within the first month, I got two one-star reviews because I was sweating on people’s food,” he said.
That episode wasn’t a badge of courage. It was one of his clearest reminders that not every hustle is worth repeating—even when it sounds convenient in the moment.
Berman, now 30 and based in Massachusetts, has tried more than 30 side hustles. The serial entrepreneur, author of “Retire by 30,” and host of “The FI Show,” tells the story like someone who learned the hard way: start, test, fail quickly, then double down on what still pays later.
His first entrepreneurial venture was a disc golf manufacturing company he started with a friend at 19. The business wasn’t. he said. “a financial home run. ” but it taught him skills he kept using: “I learned how to market. how to network. how manufacturing works. how to talk to customers. build websites.”.
Over the next decade, Berman kept experimenting. He also had a brief stint in corporate life—about seven months in commercial real estate lending. He lived on side-hustle income during that period and saved his full salary, building a roughly $35,000 cushion. That safety net helped him quit corporate work and pursue entrepreneurship full time.
To sort what worked, Berman divides side hustles into four categories: trading time for money, scalable income streams, sharing-economy plays, and hybrid or agency-style businesses.
The biggest wins for him have been in the second category—scalable “type two” side hustles. For Berman. these are income streams that can continue after the initial work is done—what he described as “something that is going to pay me in perpetuity.” He named examples including a digital product. a blog post. a podcast episode. a YouTube video. or rental property.
Today, Berman’s top income driver is his digital product business, Gold City Ventures. It started with him selling Valentine’s Day-themed love coupons and notes on Etsy, then expanded into a template library and courses, including an E-Printables side hustle course.
Real estate became another major income stream. After experimenting with long-term rentals, Airbnbs, house hacking, flipping, and hard-money lending, Berman now focuses on real-estate syndications.
His third main income bucket is personal-finance education. It includes his podcast, social media, YouTube channel, and book.
But there’s a trade-off with the “type two” approach: it usually demands upfront time before income becomes meaningful. “You’re not going to start a YouTube channel or create a digital product today and make money with either of those things tomorrow. ” Berman said. “But in six months’ time, those things might start making serious income.”.
The part he doesn’t soften is how quickly some hustles can drain you.
Berman’s biggest flop paid about $2.30 an hour. It was filling out online surveys, which he called “awful.” “It was awful,” he said, adding that it was the biggest waste of time for him.
The Uber Eats delivery detour was less about low pay and more about the toll it took. Berman said the gig paid roughly $12 to $15 an hour, but the physical demand was brutal. His shifts “would only last so long until my legs gave out.” He had taken the job because he had free time and wanted to make money without sitting at a computer while living in Australia for six months. He bought the bike on Gumtree for about $25.
When the goal is faster money, Berman’s advice is to start elsewhere. He said the easiest way to get started is usually a “type one” side hustle: trading time for money.
Examples include freelance writing. video or podcast editing. website building. landscaping. driving for Uber. shopping for Instacart. or completing tasks on Taskrabbit. That’s also what helped him supplement his income early on: he said he needed time for his “type two” side hustles to season. so he supported himself with “type one stuff.”.
The main advantage, he said, is speed. “You could literally hop on Taskrabbit tomorrow and go do a couple of tasks, or hop on Instacart or drive Uber tomorrow,” he said. “And then whenever you’re done with it, you can just put it down.”
Berman stresses that there’s no universal “best side hustle.” The right fit depends on a person’s skills, personality, interests, and goals.
His closing advice is bluntly personal: lean into what you enjoy and avoid what you do not. “There is a side hustle for everyone,” he said. “You don’t have to do the ones that I did just because those worked for me.”
For readers watching the side-hustle conversation online, his story lands in the places that matter: the real timelines, the real hourly rates, and the uncomfortable truth that the biggest lessons often come from the hustle that fails first.
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