How bootstrapping as a solo founder made me skilled in every area of my business

In 2005, I was a young twenty-something living a comfortable life in New York, working my first developer job out of college. It was a media company, and I liked the job — and the steady pay. Being a tinkerer at heart, I always had side projects, but I never considered quitting my job until I came up with the idea for Jotform.

I had a front-row seat to the frustrations of building online forms at my day job. I understood the frustration and knew there had to be a simpler way to do it.

So, armed with an idea — and trembling faith — I took the leap and left my comfortable job. I had no cofounders, no team, no skills beyond coding, and no funding. And today, Jotform is a thriving platform with over 25 million users and a team of over 650 employees across eight global offices.

Here’s how I learned everything I needed to know.

Building from the Ground Up

The first few months of Jotform I was primarily focused on building the product. But being bootstrapped, I was quickly pushed out of my comfort zone and into the nitty-gritty of the business. Having no team to delegate tasks to, I had to roll my sleeves and learn every part of the business myself.

This hands-on approach was a blessing because it gave me a unique and comprehensive understanding of how each part of the business operates. Here are some examples.

Developing the product

Coding was the one skill I had coming into this journey, but that didn’t mean it was easy. Building something people love goes beyond the technical aspects of the product. I had to learn empathy and how to stay ahead of users’ needs.

During that first year of Jotform when it was just me, I spent countless hours tweaking features, refining the user interface, and ensuring Jotform was intuitive and easy to use. Because I was so involved, I had first-hand knowledge of how users interacted with the product and what improvements were needed. Those were very special times.

Managing the project

Product management was the natural progression from coding. Prioritization was something I had to master quickly and on the fly. A particular incident from Jotform’s first year comes to mind.

In the middle of implementing a feature requested by several users, I started getting numerous bug reports. I wasn't sure which to focus on and felt compelled to handle the feature and the fixes simultaneously. It was a nightmare.

This taught me the importance of effective prioritization. I understood quickly that this wasn’t just about writing code; it was about writing the right code at the right time.

Building a user community

Early on at Jotform, I built a forum on the website where users could post comments, share issues, and ask questions. I spent so much time there and treated those first customers like family. I personally responded to their posts and implemented their suggestions in real-time.

This direct interaction was incredibly enlightening; nothing could have better helped me grasp the needs of our users or created a more devoted community.

Marketing and growing the business

While product management wasn't too out of my comfort zone, marketing was. But, being bootstrapped and alone, I didn’t have much choice but to learn.

Not knowing where to begin, I read all the marketing books and blog posts I could get my hands on, especially ones that were about lean startup ideas. I applied everything I was learning right away: I developed and executed campaigns, wrote blog posts, and engaged with users on forums.

Each effort was an experiment that gave me valuable insights that shaped my strategy. I still remember how exciting it was when my first blog post went viral and my first ads brought in new users. These events showed me that my hard work was paying off and taught me the importance of storytelling and building a brand that resonates with people.

Getting my head around accounting

At the start of this journey, I had no idea how to make a budget, handle money, or deal with cash flow. But, like with everything else, I read everything I could find on the subject and slowly learned.

Over time, all my hard work paid off, and I was able to do all my accounting work. I could make budgets, keep track of spending, and handle cash flow like a pro. Doing these tasks myself gave me a good idea of our finances, which helped me make smart choices that would protect Jotform's future. This also helped me get ready to oversee the accounting team as our business grew.

Mastering HR

With the growth of Jotform came a new challenge — HR. It took me a while to get the hang of it, but interestingly, all the hands-on experience I gained from working in different areas of the business proved invaluable.

Because I had done each of these jobs myself, I knew exactly what each position required. I could easily identify candidates who not only had the necessary skills but also fit our culture and shared our vision. It would have taken me much longer to develop this skill if bootstrapping hadn’t forced me to wear all those different hats.

Making the most of doing everything

Wearing — and learning — multiple hats is baked into being indie. It’ll happen no matter what. But there are ways to squeeze more out of it.

Here are some practical tips that have worked for me:

• Embrace continuous learning: Read books, take online classes, listen to podcasts, or attend workshops. Whatever works for you as long as you’re learning. The growth of your business is directly linked to your own personal growth.
• Go slow and learn each aspect of your business: Spend some time on each part until you're good at it, then move on to the next one. Wait to hire until you really understand the role — even if you can.
• Leverage customer interaction: Go to where your customers are. Social media is especially good for this. You can also try forums and emails. Talk to them and listen. It’s the best way to learn what they actually need.
• Stay organized and focused: Bootstrapping a business can often feel like drinking from a fire hose. To avoid drowning, use tools like Trello or Asana to manage tasks and deadlines. Prioritize tasks that have the most significant impact on your business and ignore the noise.
• Know when to hire: I know I just spent this entire article talking about the importance of doing everything yourself, but that's only for a time. A time will come when your baby becomes a teenager, and you need to trust it to be around others without your hawk-eye supervision. When it’s time to hire, do it. Don’t wait too long.
• Take care of yourself: This is the most important thing on the list. Don’t pay attention to hustle culture unless you want to burn out or develop a stroke in your forties. Sleep. Move your body. Eat food your grandmother approves of. Drink lots of water, and get some sunshine. Your business will be better for it.

A journey worth every step

As Maya Angelou wrote, "Wouldn't take nothing for my journey now." I couldn't agree more. This journey has been filled with more intrinsic and extrinsic rewards than I could have ever dreamed of all those years ago. Bootstrapping Jotform transformed not only the company but also me. It has molded me into someone my younger self would be proud of.

Beyond the confidence that comes with deep and extensive experience, bootstrapping Jotform introduced me to some of my closest friends. It brought me closer to our users and helped me build a company culture where people are happy to come to work every day.

In the end, it didn’t just bring me outward success; it brought me a deep sense of fulfillment and a lot of happiness. And really, isn’t that what it’s all about?