Top 5 Famous Businesses that Started as Side Hustles

Top 5 Famous Businesses that Started as Side Hustles

From garages to basements and spare bedrooms, a phenomenal number of big businesses expanded from humble origins. Many were not even the sole focus of their owners – they were the product of a second job, project, or side-hustle.

Some 1 in 3 people across Western Europe and America are involved in some form of side hustle.

Given some of these entrepreneurs who turned their side hustles into massive businesses, the side-hustlers of today are in good company.

Here are 5 famous businesses that started as side hustles.

1: Udemy

 Top 5 Famous Businesses that Started as Side Hustles


The Udemy founder Eren Bali was working as a freelance web developer in the early and mid-2000s when he laid the groundwork for his virtual learning platform side-hustle which would later become Udemy. Eren Bali moved his base of operations to Silicon Valley where he’d meet Oktay Caglar and Gagan Biyan to launch Udemy in 2010 with minimal funding.

The team was declined funding 30-times by investors who remain skeptical that the business had the potential to take off. The site quickly developed once launched and was valued at some $2 billion by 2020. It’s safe to say that they no longer struggle to receive funding – the platform has received some $200 million in total to date!

2: Apple

Long before the phrase ‘side hustle’ had been conceived, Steve Jobs, then an employee at Atari, was building his first ‘Apple I’ computer with Steve Wozniak.

They used Atari components in this first prototype home computer and pitched the idea to their boss Nolan Bushnell with a request of $50,000 in return for third ownership of that first Apple I computer. He declined. The rest, as they say, is history.


 Top 5 Famous Businesses that Started as Side Hustles

The Apple 1 Computer


In recent interviews, Bushnell says he doesn’t regret his decision – he had no interest in home computers at the time and says his life would have not have been the same if he was ‘uber, uber rich’.

3: Craigslist

A 90s-era side hustle, Craigslist literally started with an email sent by founder Craig Newark to some 10 to 12 people to alert them of events taking place across San Francisco. This innocent and seemingly benign motive expanded once it spread through word-of-mouth and more and more people asked to be added to the email list.

The events and alerts covered by Craiglist then expanded – Craiglists moved from a mailing list to a website. It was advertising revenue that helped monetize Craigslist, turning it into a multi-billion dollar company with remarkably low overheads.

Craig Newark stalled on the site’s development in the late 90s whilst others encouraged him to dedicate more time to it. It’s now highly successful – Craiglist’s rudimentary and utilitarian vibes have become a hallmark of the site’s practicality.

 Top 5 Famous Businesses that Started as Side Hustles


It’s also worth mentioning that Newark was 42 when he first created Craiglist – proof the side hustles aren’t confined to the younger generations.

4: Under Armour


Kevin Plank, a college footballer in the 90s, was not a fan of the then-primitive sportswear that sweated up and stuck to you on the field. Through the 90s, his side hustle was the development of synthetic sportswear that repelled sweat, later to become Under Armour.

The year was 1996 when Plank, armed with just $15,000 cash, some fabric, and a small space in his grandmother’s basement, developed his first prototypes that he marketed by sending directly to players in the NFL.

Under Armour took off from there and is now one of the world’s most famous gym and sportswear brands.

5: Yankee Candle


A true story of candlelit business romance, Yankee Candle started with literally one candle made from crayon wax, a present that sixteen-year-old Mike Kittredge made for his mother in 1969. A neighbor saw the candle and requested that Kittredge sell her one.

That small stake was reinvested, and with the assistance of two high-school friends, Kittredge managed to scale up his production to anyone in the neighborhood.

A true side-hustle, Yankee Candle was funded by Kittredge’s part-time job. He sold the company for a remarkable $500 million in 1998.

My mother in law loves to sew.

A few years ago she asked me how to set up an online store.

She wanted to sell fancy throw pillows she was making.

I gave her very basic steps. Enough to get started (I don't know much about ecom).

A few weeks later she showed me her site. It

Everyone wants “yes.”

But they don’t wanna pay the price.

100 Nos is the price of one yes.

You can get as many as yeses as you damn well please as long as you’re willing to pay the price.

I was sad to learn that Charlie Munger died today at age 99.

What a life.

He would likely roll his eyes and argue that none of us should be too surprised, based on the actuarial tables, but we’ve lost one of the 20th century’s greatest investors and businessmen.

Chris and I

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