Hey bootstrappers,

If you work a day job, chances are it’s not making you happy. 

Gallup reports that job unhappiness is at an all-time high, and 60 percent of global workers feel detached from their jobs. 

The causes and possible remedies behind this statistic are manifold, and I won’t go into them here. Instead, I want to share advice from founders who ditched their day jobs and found purpose through entrepreneurship. 

Perhaps their stories will inspire you to start a business, go all-in on your side gig, or check in on your team’s mental health.

Wherever you are on the path towards your career goals, good luck, and remember to save time for the things that make you happy (probably not money).

Chris Roper

Managing Editor

These Founders Turned Bart Simpson from Class Clown to Teacher’s Pet with a SaaS That’s Changing Education

Alexander Deeb was tired of coding other people’s products and wanted to build his own – one that elated him just as much as when teachers rolled out the TV cart in high school.

After watching his business negotiations professor use a clip from The Office to illustrate a point in class, an idea struck Alexander. What if he created a searchable database for movie and TV clips that teachers could use to liven up their lessons? Wouldn’t that make learning fun?

With help from cofounder Joyce Ang, Alexander spoke to teachers to gauge their interest. If he could categorize clips, teachers wouldn’t waste time trawling the web for relevant content, and that’s when he built ClassHook, a SaaS video database for teaching school kids.

“I didn’t want to be an engineer full-time. I wanted to work on products and solutions that help people rather than always being the builder. I’m passionate about helping people learn through media that’s not traditionally seen as anything more than recreational.”

Wins 👍

1. Using machine learning to automate clip hunting. Hunting for educational content was time-consuming, so the cofounders collaborated with MIT to automate the search.

2. Pulling videos from an existing library. Alexander and Joyce use YouTube, a public video sharing platform, exclusively to avoid copyright disputes and legal challenges.

3. Targeting districts, not teachers. Teacher salaries leave little room for the ClassHook subscription, so the cofounders targeted school districts instead.

Challenges 🤔

1. Product demos. The first few demos went poorly despite positive feedback because Alexander didn’t know how to sell. Now he’s sales-trained and closing.

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A Boring Yet Necessary Fix to Microsoft Azure DevOps Makes This Founder a Quarter Million in Revenue Every Year

Courtenay Farquharson was an Azure engineer dreaming of a lifestyle business that would free his time – and then he noticed something odd about enterprise code. It was never backed up.

Courtenay’s hands were tied when a client asked him to back up some code on Azure. No applications for it existed, despite Azure running DevOps hosting services for some of the largest companies in the world. Was this Courtenay’s opportunity to leave the rat race?

The founder built a basic backup system, Backrightup, and then posted it on the Azure forums. People had been asking for backup tools for ages, so the post was insanely popular. It even resulted in Courtenay’s first enterprise client – an Australiant telecoms giant.

“This company controls most of the landlines and internet infrastructure in Australia. They came to me about two days later and asked about the tool – but I was nowhere near ready to serve a customer that big. I told them I had the solution, but I needed to get back to them.”

Wins 👍

1. Building a self-serve web portal to validate the idea. With a big fish already on the hook, Courtenay tested demand with a simple web portal and instantly got signups.

2. Applying past SEO experience to Backrightup. Courtenay’s previous ecommerce experience had taught him how to rank for keywords and obtain backlinks.

3. Building something low maintenance but essential. A self-proclaimed indie hacker, Courtenay builds tools that make enough money that he can spend more time with his family.

Challenges 🤔

1. Figuring out how much to charge. That first enterprise client was a surprise to Courtenay and he stalled the contract to work out how to monetize his tool.

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Unfulfilled Despite a Dream Job at Google, This Bay Area Founder Built a Startup to Cure His Malaise

Despite a successful career at Google, Eric Winters felt that his life lacked meaning. He later realized it wasn’t passions he lacked but a community in which to enjoy them.

Eric’s day job brought him close to entrepreneurs – so close he wanted their lives for himself. Outside of Google, he tried various activities to see what motivated him, from pulling lonely backflips to training for the NFL Combine. But what he really wanted was a community.

After joining a bunch of groups he found the experience wanting. Although he eventually found some he liked, the trial-and-error process was discouraging, and he wanted to improve that experience with Heylo, an app fostering connections within shared interest groups.

“Going to one of these online meet-ups for the first time is terrible. It always looked like everyone was having a great time, and then I’d show up and stand awkwardly to the side. Even worse was when I’d show up and no one was there. I knew this was hard for other people too.”

Wins 👍

1. Changing the company name. Originally called Piccup, Eric and his cofounder heard from an early customer that it sounded like a dating app.

2. Cultivating connections outside of groups. Members can connect with each other on other shared interests via profiles, events, and chat messaging.

3. Focusing on making group leaders’ lives easier. Heylo handles member payments, freeing up group leaders to create memorable experiences within their groups.

Challenges 🤔

1. The pandemic. Just as Heylo monetized, the pandemic suspended all but a few groups. Eric and Brandon took a financial hit to stick with them but are now bigger than ever.

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