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From 0 to 10: Starting a business by solving our own problems

Ben Congleton
August 7, 2019

This post is the second in our “From 0 to 10” anniversary series. You can read the series introduction here.

As we celebrate Olark’s 10-year anniversary this month, I’ve found myself retelling our origin story more and more frequently. I live in the heart of Silicon Valley, where the dominant business narrative is one of fly-and-die startups, so any story about a bootstrapped company with 10 years of stable history attracts a bit of attention. People naturally want to know how we got started, and where the idea for a simple, user-friendly live chat app came from.

The answer to the second question is that Olark grew out of a problem I had in my own small business — which, as it turns out, is a pretty good place to look for ideas.

Our story

In the 1990s, I ran a web hosting company with a few friends. We were all high school students, and given that we were in class for most of the business day, customer service was a challenge; none of us had the bandwidth to answer phone calls. Most of our internal communication was via tools like AIM, ICQ, and IRC (the predecessors to Facebook Messenger, Slack, and Google Chat), so we started looking for a similar product that would allow us to chat with our customers.

Original AIM, ICQ, and IRC icons. Graphic design has come a long way since the ‘90s!

Live chat existed in the ’90s, but almost all of the available tools were aimed at (and priced for) much bigger companies. There was only one real option for small to medium businesses, which we used to great effect; in fact, our responsiveness helped us grow the business to an impressive — for high school students — $150K+ in annual revenue. But after a few years, that tool was acquired by an enterprise software company, and the price increased.

Fast forward to 2006. I was working on my PhD at the University of Michigan and kicking around ideas for products to build on the side. In one of my School of Information seminars, we’d talked about Shoshana Zuboff’s work on disintermediation — the idea that the Internet will support a larger marketplace in which producers sell directly to buyers, without relying on middlemen. I found myself wondering how producers and buyers would communicate in such a market. What about live chat? Had anything changed in that market since the 1990s?

Grad school! This is me on my 23rd birthday — a little less wisdom, and a little more hair…

As it turned out, the answer was no. Enterprise live chat solutions were alive and well, but despite the explosion of small and medium Internet-based businesses, no one had built a live chat product aimed at small teams.

I knew that if I founded another small company, I would want a chat product to be part of our daily operations. I couldn’t find an existing solution — which I saw as an opportunity to build one. That led to the first version of Olark, our acceptance into YCombinator, and the launch of our first paid product in 2009. We used Olark to support Olark customers from day one, and our continuous dogfooding has helped us uncover more problems, create solutions, and build a version of live chat that’s specifically optimized (as well as priced) for small, nimble teams.

Throwback to 2009…the very first version of the Olark website.

What we learned

Many entrepreneurs are drawn to “big” external problems, and there’s good work to be done there, too. But if you’re itching to develop a new product, my advice is to start by reflecting on your own problems — regardless of how big or small they might seem — and taking time to think deeply about solutions. You’ll know exactly what success looks like, and you’ll work with greater empathy, creativity, and drive. In the best case, you’ll uncover an unsolved problem that many people are facing. At worst, you’ll make your own life and business better by finding or adapting an existing solution that works.

Many entrepreneurs are drawn to “big” external problems, and there’s good work to be done there, too. But if you’re itching to develop a new product, my advice is to start by reflecting on your own problems — regardless of how big or small they might seem — and taking time to think deeply about solutions.

In our case, it turned out that many small businesses had challenges communicating with their customers, and our simple solution became the foundation for a successful, sustainable business. But even if Olark had never developed into anything other than an internal tool, the process of creating the product would have helped us reflect, grow, and work a little more effectively. Working on your own problems will always move you forward.

Speaking of which — we’d love to hear about the problems you’re facing in your business. Are you dealing with a challenge that might inspire your team (or someone else’s) to innovate and create something new? If you’ve recently overcome a problem, could other small businesses benefit from your solution? Leave a comment on this post, or reach out on Twitter (@jaminben and @mjpizz) or LinkedIn (Ben and Matt), to share your ideas and start a conversation.

Stay tuned — in our next post, we’ll talk about sharing toiletries, creating company values, and other essential steps to building a thriving small business culture.