How I Flipped a Side Hustle for $100k in College

I’ve read my fair share of business books—probably hundreds. And while they’re full of valuable lessons, I’ve always found that nothing beats learning by doing. It’s a cliché, I know, but think about learning to ride a bike. No one gives you a manual on balance; you just get on and figure it out, collecting a few skinned knees along the way. It’s one thing to be told what to do, but it’s another thing entirely to internalize it through your own experience.

So, why am I writing this? Because I want to share my story, from being a broke college student to selling my first business for a life-changing amount of money. My hope is that by seeing my mistakes, my wins, and the rollercoaster of emotions that comes with building a company, you can absorb some of these lessons as your own. I don’t want you to make the same errors I did, but I also don’t want your great ideas to gather dust. This story is proof that anyone can build something valuable, and it often starts when you decide to .

Most of my journey has been in the Software-as-a-Service (SaaS) world, but the core principles apply to almost anything. In my experience, a successful startup just needs to do three things right: solve a real problem, create a viable business model, and tell a compelling story. If you’re missing one of these, you might make a little money, but you’ll never truly scale.

The First Hustles

My entrepreneurial journey didn’t begin with a grand vision. It started with a series of while I was supposed to be studying. While my friends were out surfing or at skateparks, I was usually glued to my computer screen, brainstorming my next venture.

One of my earliest ideas came from the game . The game has its own economy built on digital gold, which players buy with real money to get better gear faster. It got me thinking: what if I could connect the retailers selling this digital gold with the players who wanted to buy it? Back in 2008, Google Ads were dirt cheap, so I built a simple website that pulled in buyers and sent them to a retailer, earning me an affiliate commission. It was a great , netting me about $2,500 a month at its peak. But when Google Ads prices shot up from twenty cents a click to several dollars, my margins evaporated. It was a valuable lesson in not building your house on someone else’s land.

Later, while studying at CSU Chico State and living on a diet of instant ramen, I built a job board called PhoneFreelancer. Being broke meant I didn't have much seed money, so I bought a pre-built website script for a few hundred dollars and customized it. The site was simple: businesses posted mobile app ideas, and developers bid on the projects. I took a 5% commission. This was my main focus when I was as a student. I spent that entire summer promoting it, lurking in forums and comment sections to find users. It was tedious work, but because it was my own business, I loved it. Eventually, the hard work paid off. The App Store was just taking off, and businesses were desperate to get in on the action. PhoneFreelancer became the go-to place, and at its height, it was generating around $5,000 a month—a fortune for me at the time.

The $100,000 Offer That Changed Everything

One day in 2009, I got an email from a man named Vladimir who wanted to buy PhoneFreelancer. His offer was $100,000. I read the email at least twenty times, completely in disbelief. It was more money than I had ever imagined seeing.

But something more valuable than the money was pushing me to sell. I had noticed a pattern on my own job board. Businesses, especially restaurants, were all asking for the same basic app features: menus, coupons, contact info, and reservations. Developers were charging them anywhere from $50,000 to $100,000 to build these apps from scratch, even though they were essentially just reskinning the same code.

That’s when the lightbulb went off. What if I created a template for these common apps? I could sell it on a subscription model, making it affordable for even the smallest businesses. I couldn’t believe no one was doing it already. It felt like a massive, gaping hole in the market. The $100,000 offer felt like a sign from the universe. It was the seed money I needed for my next, and much bigger, idea. This was my chance to build a truly .

Building the Next Big Thing

After I sold PhoneFreelancer, the reality of having that much money in my bank account was strange. I bought myself a $500 watch and took my friends out, but I mostly felt a sense of panic as graduation approached. The idea of a traditional job—office politics, climbing a corporate ladder—felt like the death of my autonomy.

So, I decided to go all-in on my new idea, which I called Bizness Apps. I took $10,000 of the money from the sale to build a prototype. My girlfriend (now my wife), Michelle, was understandably nervous. It was a huge chunk of my savings for an unproven idea. But she trusted me. With her support, I moved forward. The first prototype was a mess—ugly, buggy, and with limited features. But it was a start. It was my minimum viable product.

My "launch strategy" was just cold calling every local business I could find. It was brutal. Most of the time, I couldn't even get past the gatekeeper. I quickly learned that I had to stop talking about the technology and start talking about the results: more customers through coupons, interactive menus, and happy hour promotions. When I framed it as a way for them to compete with national chains for a fraction of the cost, they started listening. My first customer was the marketing manager for the campus gym. Seeing the app I built advertised on their TVs a few weeks later was an incredible feeling. That initial grind reinforced how important it is to love what you do. by yourself is tough, and without that passion, it’s easy to give up.

The Turning Point

Bizness Apps was a profitable , but I was hungry for more. I had about 70 customers and was making a few thousand dollars a month, but I knew cold calling wasn't one of those that would get me to the next level. I needed to grow faster.

I decided to enter the annual CSU Chico State Entrepreneurial Contest. I’d competed before with PhoneFreelancer but never won first place. This time felt different. I wasn't just seeking validation; I was pitching to a room full of local business owners and potential investors. During my presentation, instead of just talking about my idea, I built a mobile app for the contest right there on stage in five minutes. I showed them my real revenue charts and customer growth.

When I finished, I asked if there were any questions. For the first time, there was complete silence. The judges just stared, wide-eyed. I had stunned them. It was one of the proudest moments of my life. After the contest, one of my mentors, Peter Strauss, pulled me aside. He was blown away and introduced me to his friend, Christian Friedland, a seasoned entrepreneur. That introduction marked the beginning of the next chapter—the moment my project began its journey from a company, with the potential to become a . We still had to solve the scalability problem, but for the first time, I wasn't going to have to do it alone.