Founders Journey

People who have started companies without leaving their jobs

People who hedged their bets by starting companies while still working a day job. It’s more common than people think. The archetype of “quit everything, burn the boats, and go all in” is more myth than rule. Here are some well-known examples:

1. Steve Wozniak (Apple)

He was still working at Hewlett-Packard when he and Steve Jobs were building the first Apple computers. Woz even tried to convince HP to take the design before Apple became Apple.

2. Larry Page and Sergey Brin (Google)

They were PhD students at Stanford—effectively working their “day job” as researchers—when they built the first version of the search engine (called BackRub). They later took a leave of absence once the company took off.

3. Craig Newmark (Craigslist)

He was a software engineer at IBM and later Charles Schwab. Craigslist started as a side project email list in 1995 before it grew into a full-time business.

4. Sara Blakely (Spanx)

She was selling fax machines door-to-door when she came up with the idea for Spanx. She worked nights and weekends on her prototype before launching.

5. Pierre Omidyar (eBay)

He wrote the first code for what became eBay while working as a software engineer at General Magic. For a while, it was just a “hobby project” on the side.

6. Phil Knight (Nike)

He started Blue Ribbon Sports (the precursor to Nike) while working as an accountant at PwC and then as a professor. For years, he balanced both before Nike became big enough to be full-time.

7. Stewart Butterfield (Flickr, Slack)

Flickr began as a side project while he and his team were working on an online game. Later, Slack was also spun out from a failing game project while still managing the old company.

Principle here:

Early-stage entrepreneurship often looks less like “jumping off a cliff” and more like “running two parallel tracks until one is clearly the better bet.” It de-risks the venture, gives financial stability, and lets ideas mature without existential pressure.

Some venture capitalists even encourage founders to not quit their jobs too early, because desperation can kill creativity.

1. Dropbox – Drew Houston & Arash Ferdowsi

Drew was a MIT grad working as a software engineer and Arash was still a student when they started building Dropbox. Drew hacked on the prototype nights/weekends while consulting to pay bills.

2. Instagram – Kevin Systrom

He was working at Nextstop (a travel startup later acquired by Facebook) while developing the app that became Instagram. Only after he secured seed funding did he leave his job to go full-time.

3. GitHub – Chris Wanstrath, PJ Hyett, Tom Preston-Werner

All three had day jobs as developers and were working on GitHub as a side project. They met on weekends in coffee shops to build it before leaving their companies once the traction exploded.

4. WhatsApp – Jan Koum & Brian Acton

Koum was still doing contract work while building the first versions of WhatsApp. Acton had just left Yahoo but was still consulting when they started scaling.

5. Product Hunt – Ryan Hoover

Initially a side project launched as an email list while he was working at PlayHaven. Only later did he raise money and make it a full-time company.

6. Canva – Melanie Perkins & Cliff Obrecht

They started “Fusion Books” (the predecessor to Canva) while Melanie was a university student and also teaching design software on the side. They ran Canva in the early days without quitting other gigs.

7. Calm – Michael Acton Smith & Alex Tew

Tew (also creator of the Million Dollar Homepage) was working on other projects and consulting when Calm started as a meditation side app before becoming a billion-dollar business.

8. Zapier – Wade Foster, Bryan Helmig, Mike Knoop

They famously built Zapier while holding down day jobs. They worked evenings and weekends, then applied to Y Combinator—only quitting after they got accepted.

Pattern in modern tech startups:

• Prototype first, job second. Founders validate ideas and get initial adoption before burning bridges.
• Trigger to quit: usually when there’s outside funding, customer traction, or a clear growth inflection.
• Why it works today: Cloud infra, no need for upfront servers, and open-source tools make it easy to build real products as side projects.

This makes the “side-hustle → company” path even more viable now than in the Steve Jobs era.

India-specific cases

1. Zerodha – Nithin & Nikhil Kamath

Nithin was working as a sub-broker and trading on the side while experimenting with low-cost brokerage ideas. He built Zerodha in parallel before leaving to focus full-time.

2. Flipkart – Sachin & Binny Bansal

Both were at Amazon India when they began tinkering with an online bookstore idea. They started Flipkart in 2007, running operations out of their apartment before finally quitting Amazon.

3. Freshworks – Girish Mathrubootham

Girish was working at Zoho when he came up with the idea for Freshdesk (later Freshworks) after being frustrated with poor customer service. He started building it while still employed and quit once seed funding was secured.

4. Razorpay – Harshil Mathur & Shashank Kumar

Both were working engineers (Shashank at Schlumberger, Harshil at Microsoft) when they started hacking Razorpay as a side project. They only quit once they got into Y Combinator.

5. Oyo Rooms – Ritesh Agarwal

Oyo began as Oravel Stays, which Ritesh was experimenting with while still technically a student and working on other hustles. He pivoted and scaled Oyo later after securing funding.

6. CarDekho – Amit & Anurag Jain

They were running their family business while tinkering with CarDekho after visiting the 2008 Auto Expo. They coded it on nights/weekends before going full-time.

7. RedBus – Phanindra Sama

He was a senior design engineer at Texas Instruments when he started RedBus after facing trouble booking a bus ticket. For a while, it ran as a side project with his cofounders still employed.

8. Urban Company – Abhiraj Bhal, Varun Khaitan, Raghav Chandra

They started it (then called UrbanClap) while juggling jobs/other commitments, scaling slowly before making it full-time once they raised external capital.