Courtland Allen discusses restoring an old productivity app to its former glory and generating a healthy monthly income to boot.

What is Taskforce?

Taskforce is a plugin for Gmail and Google Apps users who need to get real work done from their inboxes. It lets you convert emails into tasks, set reminders, add due dates, assign them to others, and check them off when complete, all without leaving your inbox.

With Taskforce, it's easy for you to see all the work in your inbox at a glance, and difficult for you to make costly mistakes like forgetting to respond to an email from a client.

How did you get started?

Taskforce existed before I ever heard about it. It was a joint project between Niccolo Pantucci and Alex MacCaw, two entrepreneurs from the UK. I was living in Boston at the time, fresh out of school, but I moved to SF in hopes of either joining a startup or starting a company of my own.

I ended up meeting Nic on Hacker News. Alex had left to do other things, so Nic was looking for a co-founder. We got into Y Combinator in early 2011 and worked on Taskforce for a year or so before pivoting into another project. But we never did shut down Taskforce. It sort of ran itself, so we left it alone.

Nic and I eventually went our separate ways (mid 2014), and I bought the rights to Taskforce. By that time, it had become quite buggy and unreliable, and its monthly revenue had declined drastically. However, I had an emotional attachment to the app, and people were still writing articles about it and signing up for it, so I really wanted to build it into something that lots of people would find useful.

Where did you find the time and funding to work?

By the time I started working on Taskforce again in 2014, I was pretty close to broke. The very first thing I did was to start looking for contract jobs, so I could make money while also having the time and flexibility to devote to Taskforce on the side. I knew that I'd never find the time to work on Taskforce if I had a full-time job.

Luckily, I'm a developer living in San Francisco, so it was very easy for me to find exactly what I was looking for. I spent probably two years contracting, while simultaneously working on Taskforce between 10-20 hours a week. I wasn't very consistent — sometimes a month or two would go by with me getting very little done.

Eventually, I saved up enough money from contracting to quit and work on Taskforce full-time.

How did you handle marketing and growth?

When Nic and I first started working together in 2011, we launched Taskforce on TechCrunch (YC helped a lot with this) and got a huge wave of signups. At least 10,000 or so. We always regretted launching so big so early, because Taskforce wasn't in great shape as a product at that time, and the vast majority of signups didn't stick around.

After that, we did zero marketing and grew completely through word of mouth. Lots of people blogged about Taskforce over the years, and that's continued to drive traffic to this day.

Even when I took over the app 3 years later, Taskforce was still getting a few signups a week off the back of this earlier press and continued blogging. As I've worked on the app and improved it, the number has risen to and leveled off at about 50 signups/week on average.

How did you deal with incorporating and other legal issues?

We incorporated as part of joining Y Combinator back in 2011. They took care of all of the important details. Today, Taskforce is owned by an LLC I formed on my own.

How did you monetize? What was your revenue?

When we first launched Taskforce, it was completely free. Our goal was just to get as many users as possible. When that didn't work out as planned, we decided to charge $5/mo for access to premium features. This was in the summer of 2011.

Most people told us that that was too high, and that people didn't pay for web apps (especially not browser extensions), but we did it anyway. It turned out to be a surprising success. We made over $2000 in our first month. That was the peak.

Years later, after coming back to the app and rewriting it from scratch, I raised prices to $7/month (or $60/year) and eliminated the free tier entirely. New signups get a week to try the product before being asked to pay. This resulted in a pretty significant uptick in the conversion rate: from <1% to almost 4%. Revenue is on the rise for practically the first time ever, but it's still under $1000/mo, because there are only about 200 signups/mo at this point.

What have been your biggest challenges, fears, and mistakes?

BY FAR my biggest mistake with Taskforce has been marketing. I love coding. I love sitting down to bang out new features. But since rebuilding the app, I've had an exceptionally hard time motivating myself to start marketing it. As a result, not that many people signup. Despite having a pretty solid conversion rate and lots of happy customers, revenue isn't nearly what it could be.

The biggest challenge has been retention. It's not easy to keep people coming back and making tasks. I've found that teams stick around much more than individuals, and professionals stick around much more than people who use Taskforce for personal responsibilities. I think it's partly because it's hard to find the motivation to maintain a task list unless some outside factor (e.g. your co-workers) forces your hand.

What tools, apps, resources, skills, techniques, and habits were most useful to you?

I'm somewhat of a jack-of-all-trades programmer. I'm pretty good at aesthetic design, UX design, front-end programming, back-end programming, and server stuff. This has been both a blessing and a curse. The blessing is that I can pretty much code anything that Taskforce needs. The curse is that it'd probably be much cheaper/faster/easier for me to delegate some tasks to others.

The most useful thing I've done has consistently been to charge more aggressively. Charging more money and limiting the free plan has always and instantly moved the needle in a positive direction for Taskforce.

What is Taskforce's tech stack?

I use Ember.js, Ruby on Rails, nginx, and AWS (S3, EC2, RDS, Route 53). I can't recommend Ember.js enough for people building ambitious single-page web applications.

What's your advice for hackers setting out to be their own boss?

One of the biggest challenges is maintaining motivation. It's pretty likely that you'll pour hours/weeks/months into your project without any significant immediate returns. The idea that you're wasting your time will certainly enter your mind at some point. Find something that motivates you and boosts your optimism, then turn to that when times are tough. For me, that's always been DHH's talk at Startup School '08.

Also, go out and talk to people! If you're a hacker like me who loves to code, it's easy to fall into the trap of convincing yourself that the most important thing you can do at any given time is to code up some feature. But that time is almost always better spent in conversation with (potential) users, learning from them, selling to them, and watching them use what you've made. The longer you go without course-correcting by interacting with customers, the further off course you will drift. And that will appear to you as, "Why aren't people using/paying for my product?"

Where can we learn more about you and Taskforce?

Follow me on Twitter (@csallen), or visit Taskforce at https://www.taskforceapp.com.

I'm also on the Indie Hackers forum, so you can ask me a question below:

Subscribe for new interviews every week! 🤗

Courtland here! I regularly interview the indie hackers behind profitable apps and side projects like Taskforce. Enter your email below, and I'll send you new interviews when they're out. Feel free to unsubscribe whenever you want.

Share this interview:

Loading comments...