Being a Solo Founder of a 24x7 Hosted Web Application

There was a probably an easier way. Fortunately, it feels like we’re over the hump. Regardless, being a solo founder probably isn’t for everyone. I imagine it’s something like being a single parent. It’s not impossible, but it’s no cake walk. There’s really no such thing as “days off”. Some days are thrilling, and others are gut-wrenching. In the end, it’s worth it. Not easy. But worth it.

I should qualify what I’m calling being a “solo” founder. In the most technical sense of the word, I’m not a solo founder. I’ve had a fair amount of help. I’ve never had to really deal with our taxes, legal, or insurance matters. I’m involved with them but not responsible. Keith Jacobs, my business partner, handles most of that. However, for about four years now, I’ve been the only person in the trenches every day. Holidays. Weekends. It’s all a blur now, but if something went wrong or someone needed help, I was the one handling it. Even vacations weren’t really vacations.

Ironically, these days vacations are actually more stressful than being at home. Being out of town and away from the computer, I’m constantly aware of whether my devices are charged and how far I am from a reliable internet connection. I always keep a close eye on whether I have cell phone service. These things dominated my thoughts when I was out of town. I had stopped enjoying my time away because I was always worrying. That’s changed these days because even the worst days weren’t all that bad, and now I know that I can handle it.

Scheming & Jumping

The journey is likely the most interesting part. So lets start from the beginning. I had been scheming of ways to build Sifter since 2003. I was always sketching and wireframing ideas in my free time. From time to time, Keith and I would sit down with a spreadsheet and make up numbers about whether we could pull it off. However, with a consulting company of 20 to support, we never had the guts to try and make the transition happen. It wasn’t until 2008 until it became realistic, albeit under completely different circumstances.

Around the end of 2007, I had decided to just go ahead and build my little issue tracker for fun. I started tossing out some ideas on my blog, and before I knew it, some friends were encouraging me to try and build a business out of it all. Keith put up enough money to cover the cost of incorporating and few of other inevitable startup expenses, and I quit my job.

I had just recently paid off all of my credit cards. So, with about three months worth of financial cushion from my personal savings and impending freelance work, I could spend my extra time creating Sifter. It took eleven months working part-time on Sifter to design build and launch. I worked more than a few weekends, skipped out on some nice weather days at the lake and eventually finished development. During that time, I continued sharing my progress on our blog, and we built a modest following. By the time the launch rolled around, around 1,000 people had expressed an interest in Sifter.

We launched in December of 2008. By the end of the first month, we were bringing in $1,000 monthly and covering all of our expenses with just enough left over each month to put aside money for a rainy day. Now at this point, I wasn’t getting paid, but I was entirely responsible for a business that was expected to be open and available 24 hours a day and 7 days a week. Managing that and still working part-time to pay my bills is where things became hectic.

Balancing it All

The time period between launching and supporting me full-time was without a doubt the most challenging and exhausting experience of my life. Managing the application on top of a full or even part-time job isn’t impossible, but it’s not easy. Fortunately, there’s something exciting about working towards something that you care deeply about. It stopped feeling like work, and it just become a really long journey where every day was completely unpredictable.

It was during this time that I constantly questioned whether I was doing the right thing. I regularly turned to close friends about whether I had it in me or whether we should hire someone else to handle all of the day-to-day stuff while I got a normal job again. I explored all sorts of possible options looking for the approach that would yield the best results for our customers while ensuring that I didn’t go crazy.

The really challenging part was the constant struggle to maintain a healthy balance between work and life. In a past life, I completely neglected that balance, and it didn’t work. It makes things really easy in the short-term, but I’ve never found it to work well long-term. This time around, I made a simple promise to myself. I wasn’t going to let the business get in the way of living, and I definitely stayed true to that.

During an eighteen month period before Sifter was supporting me full-time, I moved, got engaged, planned a wedding and a honeymoon, got married, went on the honeymoon, got a puppy, bought a house, and then moved again into the new house. That’s in addition to launching and supporting Sifter while having a full-time job during half that time and a part-time job during the other half. Not too long after all that, my wife and were expecting our first child.

At every step of the way, there was a nagging feeling that I couldn’t take any of those steps until Sifter could support me full-time, but that would have meant putting everything on hold for at least a year, maybe two. Looking back now, that would have been the real mistake.

Lauren, my wife, has become a co-founder of sorts. She’s the one that has to put up with me checking email and responding to support requests in the middle of the night. When I’m driving, she regularly reads support emails to me and then types as I dictate the response to her. I give her a hard time about supporting me at times, but she’s played a significant role in enabling me to create Sifter.

She deals with the financial, emotional, and physical ups and downs of me pouring myself into something with no guarantee of success. She’s essentially going based on a promise that it won’t be this way forever. As someone who barely uses, and doesn’t really understand technology, she has placed a lot of faith in my promises despite how long of a journey it’s been.

Problems Don’t Wait for a Convenient Time

As if balancing everything day-to-day wasn’t enough, there’s always the occasional fire to put out as well. One afternoon, I discovered that someone was using our credit card processing to validate stolen credit card numbers. The individual was able to run a over a hundred card numbers before we were able to get some controls in place. With transaction fees, that came out to a couple of hundred dollars out of our pocket. Not much in the grand scheme of things, but the distraction of dealing with the fraud took its toll on my development time.

The next couple of weeks were a cat and mouse game where we locked it down a little more every few days as needed. We didn’t want to go all out and adversely affect legitimate customers, so we tightend it gradually. It wasn’t directly affecting our customers, so we didn’t want to let it get to the point where it would. It was just an ongoing distraction. One night during all of this, I was a groomsman in a friend’s wedding. The ceremony had just ended and the reception was about to start when the notifications started arriving. Ten more attempts by the fraudster.

It really wasn’t a big deal, but I let it ruin my night. At this point, I realized I’d have to go all out to lock it down, and I spent the rest of the night thinking through all of our options. Physically, I was still present, but mentally, I had completely checked out. That became a turning point for me. I recognized that things could and would go wrong at inconvenient times, but it was never anything that couldn’t be handled. These days, I generally do a better job of stepping back and deciding whether I need to respond immediately or if it can wait. If it can wait, I do my best to not let it bother me in the meantime. That’s easier said than done, though.

At first, being perpetually on call was stressful. I could have to drop everything and work at any moment, but I could also work anywhere, at any time, and any way that I desired. If I work a twelve hour day one day, I can pack it in early on the next. Once I learned to embrace the chaos, things changed dramatically. It was amazing.

These days, I wake up in the middle of night to answer support emails from customers around the world, and it’s actually kind of fun. Everyone tells me that it’s not necessary or healthy, but I’ve found that it works. Whether I work at 2am or 2pm, it really doesn’t matter. Learning to just go with the flow and adapt has literally changed everything. Now every day is an adventure, and it works. The only hard part is finding longer uninterrupted blocks of time for design and development.

The Full-time Milestone

After a tumultuous year of balancing outside work with Sifter, I finally decided that the only strategy that would save my sanity would be going full-time. That brought with it worries about health insurance combined with the fact that I’d need to take a 20% pay cut to make it work. Based on more recent offers, it turns out that it’s about a 40% paycut. The biggest lesson here was that learning to live below your means is a key enabler to starting a business.

This was the first time that money and financials became a concern. Had I been younger with fewer responsibilities, I probably wouldn’t have been thought twice about the risk. However our health insurance was dependent on my full-time employment and our mortgage wasn’t going anywhere. Combining a pay cut with paying for insurance and health care out of pocket makes for a pretty scary decision. It wasn’t made any easier by our thoughts of having our first child in the next year or so.

Once I was full-time, the next few months turned into one huge game of playing catchup. I had hoped that going full-time would be a dream come true, but all it meant was that I no longer had any distractions to take my mind off of just how much work I had to do. By early 2010, Sifter was in good shape, and we were wildly optimistic about the improvements that we had queued up. Then something completely took the wind out of my sails.

The Lowest Point

We had already begun talking about taking upgrading our infrastructure, and we were exploring the idea of moving hosts and improving our backups while simultaneously working on some significant improvements to the application. With the hopes of buying ourselves some time in order to delay the upgrades and tie up some loose ends, I decided to just upgrade up our virtual machine. I chose poorly.

The next morning when I was reviewing our performance, the increase hadn’t had much of an effect, and we made the decision to revert back to the original. At the time, all I was thinking about was the amount of downtime that it would cost us. A quick revert would just be a reboot, and we’d be down for less than a minute. Letting it ride and resizing downard later would mean 20-30 minutes of downtime. I chose the latter in order to minimize downtime. Within seconds of that decision, I realized it was a bad idea.

By reverting, we immediately lost all data that had been created on the new virtual machine overnight. It was about 11 hours worth. Fortunately, we were able to recover about 3 hours worth from our backups, but the remaining 8 hours of lost data during peak business hours for Europe still meant that some of our customers were seriously affected. I’ve never felt a sinking feeling like that before. My initial over-reaction was that our customers would leave in droves, and Sifter wouldn’t survive. Fortunately, that was far from the case.

We immediately went into recovery mode and were incredibly transparent about the mistake, the consequences, and our plans. We issued a month of credit to every affected customer and lost a fair amount of revenue as a result. I wasn’t concerned with the lost revenue, though. I was disappointed with myself. We have hundreds of customers and thousands of users that entrust their work to us, and I let them down. Over the next couple of days, I really learned just how wonderful and understanding customers can be. To the best of my knowledge, nobody cancelled as a direct result of the data loss, and most were very supportive.

Since then, we’ve dramatically improved our infrastructure. We have a dramatically improved backup system in place along with a much more scalable architecture. It was a painful lesson, but it’s a lesson that won’t be forgotten. More importantly, the result of the experience was that I’ve never been more excited or wanted to work harder for our customers. In the moment, it feels terrible, but we made it through. It’s true you know. What doesn’t kill you only makes you stronger.

These Days

Things have been much less dramatic in the last year. I’ve now been full-time for about two years, and we’re in a much better place both in terms of infrastructure and new development. I’d like to see us move a bit faster, but I also like growing at a stable rate. Fortunately, most of the behind-the-scenes work is done for a while. We can safely and quickly scale if we need to, we’re profitable, and we have some great improvements in the works.

If I had to, I’d definitely do it all over again, but if I could make one decision differently, we would have brought an additional developer on board as a founder from the beginning. Running a web app alone isn’t the best way to do things, but even under some of the most trying circumstances, it’s doable. Looking back at the last three years of working Sifter, I can honestly say that I’ve never been happier. It was a long road, but once I learned to enjoy the trip, it became much more enjoyable.