Side hustles are often sold as quick wins — easy money you can make in your spare time.
In reality, they’re usually messier. Some ideas flop, some bring in a little extra cash, and a few grow into something much bigger than expected — even replacing a full-time career.
So what separates the ones that work from the ones that don’t? Business Insider has spoken to dozens of experienced side hustlers to understand how they got started and what helped them scale.
Below, meet five entrepreneurs whose paths look very different. We asked them to get candid about what it actually takes to turn a side hustle into something lucrative, and for their best and hardest-won lessons for success.
Here’s what they told us.
1. Don’t believe the hype — test and verify
Tom Blake, 29, started experimenting with side hustles in college for a simple reason: He needed to pay his bills. In the years since, he’s tried more than 100 of them — everything from AI website generation to crypto reward programs to paid shopping.
“Many just didn’t work as advertised,” he told reporter Elle Hardy. The frustration led him to start a blog documenting his side hustle tests — which he eventually turned into a content business that generated over $1 million before he sold it.
Along the way, he learned to treat side hustles like trial and error — and to do careful research before committing time or money.
“Before trying anything, I always recommend reading reviews and checking forums as part of basic due diligence. If someone online is promising massive hourly earnings with no downside, that’s a red flag,” he said.
Read which side hustles Blake found the most lucrative and low-lift.
2. Focus on more evergreen ideas instead of trends
Michael Strahl, 41, has also tried many side hustles. The gig he found most profitable for minimal effort is one he squeezes in around both a full-time job as a lineman and his family life as a husband and dad of two.
“My full-time job keeps me on call 24/7,” he told reporter Kaila Yu. “If a storm comes through, I have to be out there in the middle of the night working on fiber optic lines and putting networks back together. This Amazon side hustle is mostly accomplished in the evening, outside family and work time.”
Strahl spends about 20 hours a month filming shoppable videos — reviews of products sold on Amazon — and makes around $10,000 a month in revenue, focusing on quality over quantity or trends.
“I believe I get better results with fewer videos because I create high-quality, evergreen content — content that could still be generating views and sales five or 10 years from now — rather than focusing on viral, temporary trends. My videos are not overly produced or cinematic, but they’re highly detailed and include product B-roll,” he said.
Read more of Strah’s advice for making consistent money on Amazon.
3. Use your age and experience to your advantage
After years in finance, including at JP Morgan and Goldman Sachs, Cassindy Chao never felt she thrived. She started matchmaking as a side hustle first, before quitting finance at 54 and turning her side work into a full-time career.
While doing so, she found that her age and life experience were assets, helping her better understand clients and build trust.
“One of the biggest fears around ageism is becoming irrelevant or out of touch, but that hasn’t been my experience,” she told Business Insider’s Joshua Nelken-Zitser. “The younger people I work with teach me about things like SEO and PR, and in return, I share the perspective and wisdom I’ve gained over the years.”
“I feel 100% more fulfilled than I did in my previous career, and it will remain sustainable as I age,” she said.
Read more about how Chao grew her matchmaking side hustle through word of mouth.
4. Build something that’s easy for you to create — and use tools to grow it
For Joey Coffin, founder of the lifestyle brand Vacation Darts, everything started with a simple idea that naturally resonated with him.
“Do something you actually love and believe in, and that will translate well,” he told BI’s Robin Madell.
Coffin built the brand while working full-time, turning an inside joke into a six-figure business. He relied on organic social media, direct outreach, and AI tools to build momentum — even messaging influencers who engaged with his content.
By staying authentic and using available tools strategically, he was able to scale his side hustle into a full-time venture.
Read how Coffin grew his side hustle to $112,000 in revenue.
5. Say yes before you feel ready
Kit Huffman’s side hustle began in an unlikely place: living out of her car during a gap year.
At 22, she was writing LinkedIn posts for small clients when she landed a ghostwriting opportunity for the CEO of a global bank — despite having no formal credentials.
“They didn’t know I was a dyslexic 22-year-old without a college degree who was living out of her car,” she wrote in an essay for Business Insider.
Huffman took the opportunity anyway and learned on the fly. That decision helped launch her career in ghostwriting and eventually led her to start her own agency.
Her success showcases how opportunities often come before you feel fully prepared — and how a leap of faith can pay off.
Read how Huffman started a ghostwriting career from her car.
Got a side hustle story to share? Contact this editor, Debbie Strong, at [email protected].
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