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Top 10 Best Side Hustles That Became Empires

Every empire starts somewhere small. This list rounds up 10 famous side hustles — from a college student's computer in a garage to a door-to-door salesperson cutting the feet off pantyhose — that quietly grew into billion-dollar businesses. Vote for the origin story that inspires you most, and share the list with a friend who's still tinkering on their weekend project.

2026122 viewsJul 13, 2026 Updated Oct 3, 2026

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#1
Apple
The Apple I remains the most iconic side-hustle origin story on this list, starting as Steve Wozniak's hobby project for his computer club and evolving into a $3 trillion empire with Steve Jobs' salesmanship. Assembled in a Los Altos garage in 1976, the first 200 units sold at $666.66 each, generating $133,332 in initial revenue. Unlike Spanx and Under Armour, which began with single products aimed at niche markets, Apple's early personal computer directly created the consumer electronics category. This explains why Amazon took 4 years to reach its first $1 million, while Apple hit $1 million in sales within its first year. The hand-built circuit boards were crude, but the vision disrupted mainframe computing.
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#2
Amazon
Amazon's side hustle from Jeff Bezos's Seattle garage in 1994 outperforms Apple in scalability, transforming from a books-only online store into a $1.7 trillion logistics and cloud-computing titan. Bezos personally drove packages in his Chevy Blazer to the post office, yet within 30 days of launch in July 1995, Amazon sold books to all 50 U.S. states and 45 countries—a customer reach 30% faster than the average e-commerce startup. The early focus on customer obsession, not profit, led to a 2,300% increase in sales from 1996 to 1997. By comparison, Under Armour took 5 years to reach $10 million in revenue, while Amazon surpassed $1 billion in sales by 1998.
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#3
Spanx
Spanx began when Sara Blakely cut the feet off pantyhose while working as a door-to-door fax machine salesperson, investing just $5,000 of her savings to create a shapewear category that now generates over $400 million annually. Blakely's prototype—footless pantyhose with a reinforced waistband—solved a tangible problem for women without any existing market research. This makes Spanx 50% more cost-efficient than #2 Amazon's initial book inventory investment, since Blakely manufactured the first 1,000 units with only $5,000. By 2000, Oprah Winfrey named Spanx a "Favorite Thing," driving first-year sales to $8 million—a growth rate 3x faster than #4 Under Armour's debut year revenue.
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#4
Under Armour
Under Armour started when Kevin Plank sewed moisture-wicking shirts in his grandmother's basement while playing college football, selling them from his car trunk to teammates in 1996. Plank's targeting of athletes led to $17,000 in sales the first year and $10 million by 2000, a trajectory comparable to the average apparel startup's 10-year path compressed into 4. By 2014, Under Armour reached $3 billion in annual revenue, proving that basement-sewn side hustles can challenge industry giants like Nike.
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#5
Craigslist
Craigslist became a classifieds empire by gutting the newspaper industry, starting as a 1995 email list from Craig Newmark's personal hobby. The site grew organically to over 80 million monthly users in the U.S. by 2023, generating an estimated $1 billion in annual revenue with fewer than 50 employees. Its free postings in most categories disrupted traditional classifieds, which charged up to $50 per ad in major papers. The platform's simplicity and lack of venture capital funding allowed it to dominate without external pressure, a stark contrast to the high-burn startups on this list.
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#6
Yankee Candle
Yankee Candle started from a high school side hustle in 1969 when Michael Kittredge melted crayons to create a Christmas gift for his mother, which neighbors wanted to buy. The company grew to $1.75 billion in sales by 2022, with over 500 retail stores and a dominant 35% share of the U.S. candle market. The brand's seasonal collections, selling over 200 million candles annually, turned a homemade gift into a global empire.
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#7
Airbnb
Airbnb transformed home-sharing into a $100 billion empire after Brian Chesky and Joe Gebbia rented air mattresses in their San Francisco apartment during a 2008 design conference. The platform now lists over 7 million properties globally and generated $8.4 billion in revenue in 2022, growing 40% faster than the traditional hotel industry. Its user base exploded because it undercut hotels by an average of 30% per night, while offering unique stays impossible for chains. The company's pandemic recovery, with bookings surging 50% in 2021, proved its resilience over physical retail ventures like Yankee Candle.
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#8
Dell Technologies
Dell Technologies turned a dorm-room PC upgrade business into a $90 billion technology giant, with Michael Dell selling custom computers from his University of Texas room in 1984. The direct-to-consumer model cut out retailers, reducing costs by 20% compared to rivals like IBM, and fueled revenue growth to $5 million in its first year. By 2023, Dell held a 16% share of the global PC market, shipping over 50 million units annually.
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#9
Gymshark
Ben Francis started screen-printing gym T-shirts from his parents' garage in Birmingham while working as a Pizza Hut delivery driver, building a $1.3 billion fitness apparel brand by age 28.
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#10
Mailchimp
Ben Chestnut and Dan Kurzius built an email marketing tool as a side project for their web design agency in 2001, bootstrapping it for 20 years before selling to Intuit for $12 billion.
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Frequently Asked Questions About Side Hustles That Became Empires

What is a side hustle? A side hustle is a small project or business someone runs alongside a day job, school, or other main commitment — often in evenings or weekends.

Can a side hustle really become an empire? Yes. This list shows 10 examples of side projects that grew into globally recognized companies worth billions of dollars.

What do these side-hustle empires have in common? They all started small, solved a problem their founders cared about, and grew through word of mouth before becoming mainstream brands.

Which side hustle on this list is the most famous? That is up to you — scroll up and vote for the origin story you find most inspiring.

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Frequently asked questions

What is the first step to turning a side hustle into an empire?

Start by validating your idea with real customers while keeping your main job to minimize financial risk, then reinvest early profits into scaling operations.

Can any side hustle become a large business?

Not all, but side hustles that solve a widespread, recurring problem and have a clear path to scalability—such as software, direct-to-consumer products, or service-based models—stand the best chance of growing into an empire.

How much time should I commit to a side hustle to see significant growth?

Expect to dedicate 10–15 hours per week initially, increasing to 30+ hours as you automate or outsource tasks and demand grows.

Should I quit my day job to focus on a side hustle full-time?

Only quit after your side hustle consistently generates at least as much income as your salary and you have a 3–6 month financial cushion to cover business expenses.

How can I scale a side hustle without a large upfront investment?

Use lean methods like dropshipping, print-on-demand, or freelance platforms to start; reinvest profits into automation tools, outsourcing, and paid advertising once you have proven demand.