25 Successful Side Hustle Ideas and the Entrepreneurs Who Started Them

Believe it or not, some of the world’s most successful businesses started out simply as side hustle ideas.

And the entrepreneurs behind these apps, products and services you use are exactly like you—they’re not superhuman.

They started their pursuit towards finding the right side hustle idea as nothing more than unsatisfied employees, consultants, freelancers, students and even couples.

Now they’ve turned what used to be a side hustle idea into a full-time income. And on occasion, multi-billion dollar companies.

Today’s guest post comes to you from my friend Anatoly Kvitnisky, Founder at BlastoffCode where he coaches entrepreneurs (without a tech background) who want to go from side hustle idea to profitable business in a matter of weeks—not months or years.

Here he is delivering a keynote presentation last week on behalf of Trulioo, the leading global identity verification service, where he’s still the VP of Growth (yes, he still has a day job).

I met Anatoly last year while I was teaching a class about how to find a profitable side hustle idea here at General Assembly in San Francisco.

We quickly bonded over how similar our work is and since then, we’ve stayed in touch. He’s made a ton of progress helping other entrepreneurs build momentum with validating their side hustle ideas.

Enough from me, let’s get into Anatoly’s guest post.

…

Here’s Anatoly…

In this post, we’re going to take a look at how 25 entrepreneurs grew their side hustle ideas into companies that have now earned more than $1,000,000.

We’re going shatter some of the most recycled, out-dated and bad business advice like, don’t start a company with your life partner, and don’t sell your time for money.

We’ll reaffirm valuable words of wisdom like, solve your own problems, that have helped these successful entrepreneurs go from side hustle idea to million dollar business.

Most importantly, these stories are meant to inspire you to take action.

 

25 Side Hustle Ideas and the Entrepreneurs Who Started Them

1. Dharmesh Shah, HubSpot CTO and Founder.

In between selling his first startup and founding his current one, Dharmesh started a blog. A funny thing happened, OnStartups blew up! In his own words “a tiny blog with no budget generated more traffic than companies with professional marketing teams.” Roughly 7 months later, armed with lessons learned from blogging, Dharmesh co-founded HubSpot as just a side hustle idea. Today, HubSpot is publicly traded and is worth roughly $2B. Hopefully all the bloggers reading this have similar outcomes from their own blogging experience!

2. Ryan Hoover, Founder and CEO of Product Hunt.

Ryan spent roughly 4 years after college working closely with founders of startups before founding Product Hunt. Product Hunt curates top products, which are mostly tech, for people to discover every day. Sound complicated to make? In the beginning, he kept it as simple as possible: he created a group on Linkydink, came up with a clever blog post idea which he published and promoted on his Twitter account and then emailed his contacts. Product Hunt had 170 users while it was just a side hustle idea, long before Ryan ever built an actual platform for it. From these humble beginnings, the company was recently acquired by Angellist for an estimated $20 million.

3. Alon and Adi Tatarko, Founders of Houzz.

As a married tech entrepreneur, this side hustle idea (and story) strikes a special chord for me. Can you count the times you heard the startup advice to not start a company with your wife, husband or life partner? Alon and Adi Tatarko are doing their best to put this one to bed. Starting a multi billion dollar company helps the cause. Houzz was started from the couple’s kitchen table while both Alon and Adi were gainfully employed in tech and finance, respectively. Due to their frustration with the home remodeling process, they launched Houzz to help themselves. It’s wasn’t fame and riches from the beginning, the couple bootstrapped the company for 18 months while keeping their day jobs. 8 years later, Houzz is valued at over $2 billion.

4. Benjamin Kapelushnik aka Benjamin Kickz, 16 year old sneaker reseller.

Know anyone who makes over a million in sales per year and still lives with their parents? Or a side hustler who is just 16 years old? Now you do: Benjamin Kickz. He started reselling limited edition and hard to get sneakers in 5th grade as a side hustle idea and is now doing over a million in sales at age 16. Did you know that the sneaker resell industry is a billion dollar industry? News to me too. The best part about Benjamin is he does it for the love of the game: “I do it, in general, to keep the shoe, not to make money on it.”

5. Steve Wozniak, Apple co-Founder.

Creating a list of side hustle ideas and not including Apple would be blasphemy. Yes, Apple was also Steve Jobs’ (who’s featured multiple times in my article about motivational quotes) side hustle while he worked at Atari. But Wozniak’s story will resonate with more side hustlers. He worked at Hewlett-Packard making calculators while creating the first Apple computer at night. The funny part is he was happy and loyal working at Hewlett-Packard in the mid-70s.

He even offered them the designs for the first Apple computer. 5 times. For free. Ever had one your projects declined at your job? Not that anyone needs a history lesson of what happened in the 40 years since, but Apple is the largest company (by market cap) in the world today. Apple would go on to create the iPhone, which allowed thousands of entrepreneurs to come along and create ancillary side hustle businesses to support that ecosystem—like starting a phone case business.

6. Sal Khan, Founder of Khan Academy.

What started as just tutoring his cousins, Sal Khan got the following feedback: his cousins preferred seeing him online than in person (thanks?). With that insight, he began creating 10 minute YouTube clips on subjects ranging from biology to art all while being employed as a hedge fund analyst. With no plan nor business model, he launched Khan Academy to provide a free world class education to anyone as a side hustle idea at first. Since then, he’s written a book and his lessons are being used to teach children around the world. Something tells me this will work out ok for Sal.

7. Bo Fishback, CEO of Zaarly.

Do you have that outgoing friend who’s always convincing you to do something you never thought you’d do? Skydive maybe? Backpack across Europe? Go out on a school night? Start a company perhaps? Bo Fishback can thank Eric Koester for convincing him to get on a flight to LA for Startup Weekend. Bo was working at Kauffman Foundation’s Kauffman Labs before starting Zaarly as a side hustle idea, a marketplace for local service providers, just 1 week after the startup event. To be fair, sometimes these outgoing friends don’t always make the best decisions for you. But, over $15 million in funding later for Zaarly, I’d bet Bo is glad he listened to Eric. Bo did make Eric his COO after all.

8. Andrew Mason, Groupon Founder.

Another entrepreneur with humble beginnings. In 2006, Andrew Mason was doing contract work building databases. Super exciting, I know. In 2007, he started a company, The Point, with his employer’s blessing and backing as a side hustle idea. 2 years into the company, Andrew accidentally stumbled on the group buying craze that led to Groupon. Groupon’s founding story feels like entrepreneurial inception: side hustle within a side hustle. Groupon eventually IPO’d and made Andrew a billionaire in the process.

9. Chris Wanstrath, CEO and Co-Founder of GitHub.

“It all started with a domain, a cheap slice from Slicehost, and some stock art.” Before GitHub became the billion dollar company it is today, Chris and his co-Founder, PJ Hyett, took on contract work while Tom Preston-Werner, the 3rd co-Founder, held a full-time job. Together, they worked on GitHub on nights and weekends as a side hustle idea. As a way to motivate themselves, they set monthly goals that determined their paychecks. What a concept! With close to 20 million users and hundreds of millions in venture capital raised to date, surprised this productivity and motivation hack isn’t getting more love and attention given how well it worked with GitHub in its early days.

10. Naval Ravikant, CEO of AngelList.

Naval Ravikant, one of the most respected entrepreneurs and investors in Silicon Valley, wanted to share his insight on fundraising. So he taught himself how to start a blog and called it Venture Hacks—which he partnered with another entrepreneur, Babak Nivi, on as just a side hustle idea. He did this while still running his startup, Vast. The second iteration of his fundraising cause was when Naval began connecting vetted entrepreneurs to his rolodex of investors. This is what prompted him to build a social network for investors and startups, Angellist. Well on his way to disrupting how capital is raised with Angellist, his template to starting a company from a side hustle blog is one many can learn from.

11. Tommy Griffith, started ClickMinded and CourseMinded.

A guy making 6 figures on his side hustle idea and still working at a day job? Too. Much. Hustle. Tommy Griffith knows a thing or 2 about SEO after doing it for PayPal and currently for Airbnb. He took his expertise and began teaching in-person 1 day seminars. After demand increased across the country, he started an online course. 3 years after working on ClickMinded, it crossed the 6-figure mark. Looks like Tommy Griffith can’t stop, won’t stop as he recently launched CourseMinded.

12. Moshe Hogeg, Founder of Yo.

Who ever said CEOs can’t pursue side hustle ideas? That’s exactly how Yo, the silly simple messaging app, got started. Moshe Hogeg, Yo’s Founder, was running another technology company, Mobli, while launching Yo. Yes, Mobli made ‘serious technology,’ as Moshe called it. Maybe Joker was right, seriousness is in fact overrated if the opposite approach lands Yo millions of users and millions in funding.

13. Rob Kalin, Founder and former CEO of Etsy.

You’re right if you think starting a freelance business can be a long and difficult journey to freedom [in Braveheart voice]. But that shouldn’t stop anyone from doing it as a side hustle idea, since it could lead to a healthy boost in your income as well as new connections and relationships (especially if you have a solid freelance proposal and freelance contract). Ask Rob Kalin, the Founder of Etsy. After college, Rob built websites on a freelance basis. One of the side hustle ideas he took on was a forum for crafters. This may or may not have inspired Rob and his Co-Founders to start Etsy, the publicly traded marketplace for crafters to sell their creations.

14. Fabio Federici, CEO of Skry (formerly Coinalytics).

Coding for fun at nights, dropping out of an MBA program to start a bitcoin company, and leaving his home country to try to make it in Silicon Valley. This is what entrepreneurial dreams are made of. Fabio Federici was pursuing his MBA in Switzerland when he was introduced to Bitcoin. Instead of putting together research papers and powerpoints like most MBAs are inclined to do, he began building his side hustle idea, Coinalytics (which later became Skry). A trip to San Francisco led to a stint in 500startups for his company and later a million dollar funding round. Fabio, you are an inspiration for MBA student side hustlers everywhere!

15. Jeff Sheldon, CEO of Ugmonk.

Designer by day, t-shirt and brand Founder by night. For 2 years, Jeff wore both hats. Only after some traction did he take the full-time plunge into his brand. Now with sales in the millions and shipping to over 60 countries, Jeff can claim a side hustle idea win and one of the sweetest workstations ever. Jeff is also proving you can run a company from anywhere (leveraging online business tools like team communications platforms, the best CRMs for small business, project management tools and the like), starting Ugmonk in Vermont and now leading it in Downingtown, Pennsylvania.

16. Ramit Sethi, Founder of I Will Teach You to be Rich.

One of best blogger success stories, Ramit Sethi turned his personal finance blog (with a not spammy sounding URL) into a best-selling business book, multiple online business courses and even in-person conferences. Persistence does pay off on the internet, as it took him 9 years to get to where he is today. Patience really pays off too, as Ramit ran the blog for over 2 years as a side hustle idea before ever trying to learn how to make money blogging through the digital products he now sells. Outspoken as he is, Ramit preaches that running his own lifestyle business beats the days he used to work at venture backed startups and it’s a major step up from just building a freelance business around work from home jobs.

17. Sahil Lavingia, CEO of Gumroad.

It takes serious cahunas, for both girls and boys, to leave Pinterest before your stock vests. But when you believe in your business idea as much as Sahil Lavingia believed in Gumroad, it seemed like a no brainer. While still working at Pinterest as a designer, he realized it was actually tough to sell digital products on the internet. He tweeted his idea to get validation and then got to work on his side hustle idea with the goal of making eCommerce easier to navigate. After being employed at Pinterest for about 10 months, he left to pursue Gumroad full-time. And yes, Sahil sells his own creations on his site.

18. Ben Earley, Co-Founder of Paul Evans.

Who finds mens square toe shoes a turn on? You know, the ones you see at every corporate office? If you do, just skip the rest of this one and scroll down to the 18th story. Ben Earley did not find those tired shoes attractive and thought to do something about it. He cofounded Paul Evans, a men’s shoe brand as just a side hustle idea. Though his shoe company was doing well into 6 figures of revenue just 2 years in, Ben still kept his Wall Street job. He did commit full-time to his side hustle in 2014. Keep fighting the good fight Ben!

19. Adam Neumann, WeWork Co-Founder and CEO.

Welp, this one hasn’t been able to stand the test of time. Still a million-dollar idea though? Apparently so (according to their investors). From baby clothing company to leasing co-working space? Can’t make this stuff up if you tried. But this is exactly how Adam Neumann, another entrepreneur starting on a side hustle idea, watched his story play out. When Adam saw that the office building he was in had vacant room, he started a startup co-working space while still running Egg Baby. This was 2008. In 2010, he officially started a business named WeWork, which has raised into the billions of venture capital and has expanded into more than 23 cities across the globe. Hear, hear side hustlers!

20. Gagan Biyani, CEO of Udemy.

How many happy IT consultants do you know? Me neither. No wonder Gagan Biyani started working on a side hustle idea that eventually became Udemy, while working at the consulting firm Accenture full-time. He even went through a part-time incubator, Founders Institute, to help. And help it has: Udemy boasts 42,000 courses and has raised over $170 million to date.

21. Kevin Plank, CEO of Under Armor.

Raise your hand if you’ve ever heard a college student say “I would totally start X if only I had money.” Not having tons of money didn’t stop Kevin Plank, the CEO and Founder of Under Armor. As a college student, he was able to save $20,000 by selling t-shirts (of course) at concerts. To start Under Armor, Kevin also racked up $40,000 in credit card debt. But he was able to see his side hustle idea through for Under Armor apparel all at the age of 24. Today, you could say it was worth it for Kevin as Under Armor does nearly $2B in sales and also backs the bay area’s favorite athlete, Stephen Curry.

22. Kevin Systrom, CEO and Founder of Instagram.

Don’t how to code? Learn. Have a job but also a side hustle idea you want to launch? Do it at night. Kevin Systrom is the ultimate side hustler! Not only did he level up the skills he lacked, he also didn’t let his full-time job stop him from launching his app, Burbn. Though you most likely never heard of that one, you probably know of and use what Burbn became: Instagram, which was acquired by Facebook for $1 Billion. Not bad for something that started as just a side hustle idea.

23. Phanindra Sama, Co-Founder of redBus.

Happily employed at Texas Instruments for over 2 years, you can call Phanindra Sama an accidental entrepreneur. What inspired him to start working on his side hustle idea is what’s inspired many entrepreneurs: a problem they personally felt. For Phanindra, it was his inability to get a bus ticket during Diwali of 2005. This led to him starting redBus with 2 of his college classmates. Even with early success, Phanindra still had some fears: “The initial hurdle was to move out of our comfort zone. We were very pampered at our respective jobs and we were shielded from the tough world outside.” Luckily for him, and all bus commuters in India, he did go on to work on redBus full-time and sold it 7 years later for $101m.

24. Alan Schaaf, CEO and Founder of Imgur.

Athens, Ohio the mecca of startups! Ok maybe not, but that is where Imgur’s side hustle idea (and story) begins. Alan Schaaf started Imgur as a side hustle idea from his college dorm room at Ohio University. He didn’t work on it full-time until after graduating. His motivation for starting Imgur was quite simple: all other image hosting sites at the time sucked and often didn’t work well on social sites like reddit. Alan seems full of knowledge bombs after bootstrapping his side hustle idea and later raising a $40m funding round but my favorite quote of his is “The only money I’ve ever invested personally into the service was the $7 for the initial domain name. We’ve always been profitable.” I hope this is true for your side hustle idea too.

25. Joel Gascoigne, CEO and Founder of Buffer.

Joel worked on starting a few startups before Buffer with minimum success. Then he had an entrepreneurial revelation via Eric Reiss: validate your business idea before building. Buffer was born in Joel’s bedroom in 2010 from just working on it on nights and weekends while running another startup. Buffer started with a simple premise, to schedule tweets, and has gone on to achieve at $13m annual run rate. We can all learn from the way Joel launched Buffer from a simple 2-page website as nothing more than just a side hustle idea, and how it’s grown into one of the leading social media tool startups of today.

As promised, we’ve seen everyone from consultants to college students launch successful side hustle ideas. Some of the common lessons that come up multiple times from these 25 entrepreneurs:

•   Many businesses start from blogs
•   Many businesses start from email lists
•   Share your idea early and often to validate
•   Solving your own pain points is the most common path to side hustle success
•   Service businesses are not bad side hustles and often lead to new products

I hope you are as inspired from these side hustle ideas and the stories behind them, as I was. With that, I’m off to work on my own side hustle idea!

What’d I miss?

Know of any companies that started as just side hustle ideas?

Share with us in the comments below!