The Startup That Never Started: Lessons from .Mail

.Mail (I'm going to use DotMail here, for easier reading) was an email app concept I originally came up with and designed in 2010. DotMail never saw the light of the day. It never launched and it would haunt me for many years to come.

This is the full story, from where DotMail began to how it failed before it even got off the ground. Looking back, there wasn't a single reason for its failure, but many. Many lessons I've learned that I would like to share with you.

The DotMail story begins around early 2010. It was one of those ideas sleeping in my notes for a while, but I never knew what to do with it. It was just one idea one of many, roughly formulated and sitting there, waiting to happen.

Working on my design consulting business during the day I’d grown frustrated with how much time I spent wasting on email, so I was naturally looking for a fix. Over that year and the next, I spent a fair amount of time talking with friends and colleagues about their email habits, taking notes and adding them to my DotMail concept.

The more I talked about emails, the more I learned how many struggled with the way email worked (or didn’t work) at the time. I also learned that everybody had their own little hacks to make their email client work for them. At the time there wasn’t much happening in the email apps space. The most popular one (and my own favorite) besides Apple Mail, Gmail, Outlook and Thunderbird was Sparrow for Mac, launched by a small team in France in 2011. There were a few others such as Postbox, but they weren’t really solving it for me either, most of them were cluttered and feature packed with things no one needed.

The deeper I went down the email hole, the more I got fired up about DotMail. I needed to do something about it because the idea kept itching me. I was fully aware that designing a concept for an email client is one thing, but developing it and working through the technical hassles was another, and I certainly couldn’t do it myself. The idea had to be simple if I wanted to get anything done at all. So I worked through some concepts and ended up sharing my favorite one with some thoughts on my website. It was a fulfilling compromise: I could work on the fun stuff, sharing my thoughts and findings with no intention of ever building it. It was a nice little challenge for me.

After much procrastination and many experiments I finally put something together I liked. I decided to publish a case study on my website that outlined the idea of the DotMail concept. You can see the original case study I published here. I remember it was around midnight that day and I didn’t think much of it; I just hit publish, shared it on Twitter and Facebook with my friends and went to bed. I felt good and was happy it was now out of my way.

The next morning I woke up to dozens of emails, tweets and Facebook comments. My little DotMail concept got shared way beyond my usual circle and I couldn’t believe it. Over the next 24 hours, hundreds of emails and more tweets rolled in not only with feedback, but with people asking me when the app was going to launch, despite me never mentioning anything about launching this app for real. It was a theoretical concept after all.

I was speechless, and quite nervous. Could I actually launch this app? What should I do with all this feedback? I never planned to work on DotMail beyond this concept, but suddenly other people were excited about it. As you can imagine, that made me excited as well.

So I did what everyone would probably do: I considered the possibility of making DotMail come to life. The pressure was on me anyway, and I could make use of the newfound exposure. Within hours that day I registered a domain and launched a little landing page with an email sign-up. For me it was more of a test to see how many people would sign up and consider using (and paying) for DotMail. It all still felt pretty unreal and rushed to me, but I wanted to measure the interest in a more meaningful way.

A couple days went by and thousands of people signed up to the DotMail email list. FastCompany wrote an article about it titled "A Simple Idea That Could Revolutionize Email And Save You Time." Many other online magazines and blogs showed interest and I couldn’t sit still from the anxiety mixed with excitement. Over the course of the following three months, more than 100,000 people signed up for the app. It was pretty clear. People wanted DotMail.

I sat down and tried to think about my next steps. Is this really what I want to do? Should I hire a developer and see how far we can go? After reading more into the details of email protocols and the technicalities behind it, I quickly realized I needed to look for help first, and maybe not even build this all myself.

My first thought was to reach out to the people at Sparrow. While it was a fairly basic email client, I enjoyed using Sparrow and thought there might be potential for a collaboration. I reached out to Dom, the founder, around mid 2012 and pitched him the idea of DotMail. I asked if there was any chance of working together and making parts of DotMail become reality on an already solid email client foundation. Because if you think about it, building an email client means you first have to build the foundation that any other email client already has. The majority of your effort will be spent laying the groundwork, doing the "boring" work and building the fundamentals that everyone takes for granted since many years (aka sending, drafting, receiving and displaying emails, which may sound simple, but is a nightmare in reality).

To my surprise, Dom got back to me and we connected via Skype. At the time, the Sparrow team was quite busy with the launch of their upcoming iPad app so we delayed our phone call until a bit later with a promise to stay in touch. I didn’t have high expectations, but it was worth a shot. But just two weeks later I got a short message telling me there was unfortunately no possibility of a collaboration in the future. They didn't provide any specific reasoning, but it didn't take long for me to figure out what happened. Just a day later, tech news announced that the Sparrow team got acquired by Google to work on Gmail. Sparrow, my favorite email client, was essentially dead. Google and the Sparrow team weren’t planning to continue Sparrow.

Now that Sparrow was gone, the interest in DotMail increased. I had to do something about it and quickly started looking for a partner and developer who could join the team. As you can imagine, that wasn’t an easy task in itself. I wasn't just looking for a developer, I essentially had to find someone who was ready to commit with me as a partner. I needed someone who would invest their own time and money, who knew their way around front-end development for MacOSX, including the ins and outs of email protocols, and could build the engine. Finding all of that in one person would need a small miracle.

With all the press around the acquisition of Sparrow and my email concept, the email space finally woke up. Within months, dozens of other email client concepts popped up promising to solve your problems. Suddenly it seemed trendy to work on email clients. One of the more promising ones was called Mailbox, which was announced in early 2013 but sadly focused only on iOS. Mailbox had an interesting approach that I really liked. On top of it, Mailbox was hugely successful with its announcement and more than a million people signed up with the hope to see Mailbox launch a couple months later.

To me, Mailbox seemed like a new opportunity, especially because it was developed by a company called Orchestra which also developed a successful productivity app earlier in 2011. Orchestra had the funds and the talent to really make it happen. So as I'd done with Sparrow, I reached out to Gentry, one of the co-founders of Mailbox.

Gentry was one of the nicest people I've had the chance to meet in my career. He was open to a conversation without any promises and we exchanged a couple emails. However, the timing was unfortunate as it was exactly when Mailbox was preparing for their launch in early 2013. Gentry was busy dealing with Mailbox and getting it off the ground. I understood that talking about a Mailbox desktop client was just way too early. We promised to stay in touch while exchanging a couple more messages to see how we could eventually work together in the future.

Two months later, Mailbox got acquired by Dropbox, which planned to release a desktop version of Mailbox sometime in the near future. And while there were talks of me potentially joining the Mailbox or Dropbox team, I knew that DotMail wasn't going to happen. (Dropbox eventually shut down Mailbox in 2015, saying they were unable to “fundamentally fix email.")  I continued my search for a partner and developer, but I was thankful so far to have met so many talented people like Gentry in the process.

After almost two years I was never able to find a partner who stuck around long enough to make it work. I ended up working with three different people who eventually dropped out due to the workload and technical challenges. While we did get some prototypes off the ground, even after years of work we were still miles away from having anything close to a public alpha version.

The only comforting thing in these years was that 99% of all the other new email client concepts that got announced also never saw the light of the day. It helped to know this shit is hard and I wasn't the only one struggling with it. Secretly I was hoping that any promising new email client would get off the ground, but none of them survived, at least at the time.

In the end we failed horribly. It wasn't a matter of whether email could be fixed — that's beside the point. It came down to reasons much easier to understand in retrospect.

Underestimating the task at hand

Sadly, with every attempt at this project, we completely underestimated the technical challenges at hand. As I depended on my technical counterpart, I had to rely on their knowledge and estimates. What happened was that due to our initial excitement, most estimates were completely wrong. Ultimately, the developers I worked with slowly faded out and gave up. It was as much my fault as theirs; I failed at managing expectations and doing reality checks more often. And I don't blame them. The technology behind email is daunting and the end never seemed to be in sight.

The need for a more formal partnership

With all developers I made partners, there was a lack of commitment. Even when doing 50/50 partnerships, it was always a hit or miss. Even more so if these partnerships were with people I hadn't known or worked with before.

It’s why good hiring often takes a long time and why it is so important. If there is no existing trust, you need to trust the process of hiring and take your time. My mistake was that I did not take my time, but went with the first people who showed enough excitement to work on DotMail. As you can imagine, their excitement wore off quite quickly when the real work began. In the end I felt like I was constantly running after someone when we should have been equally committed. DotMail taught me a lot about hiring and firing, and my failure was that I didn’t do both. I didn’t hire properly and I didn’t fire fast enough. I was just wasting my time and theirs.

DotMail showed me that unless you've known someone for many years and have established trust in your relationship, you need a more formal working agreement that protects both parties — otherwise someone is getting fucked over.

My commitment was lacking as well, at least mentally.

Another reason DotMail failed was that over time, I only gave it a certain percentage of my attention. As my decision was to bootstrap DotMail and not take on external funding, I knew that both me and my partner needed to work on this in our spare time to finance it and make it work. But ultimately I never gave DotMail the attention it deserved, which leads me to my next point:

I simply didn’t love DotMail as much as I should have.

It took me a long time to understand why DotMail didn’t get the attention it deserved. I was initially fired up about the concept. I was excited to think about the challenges and I enjoyed sharing my findings with other people. Following all the exposure and feedback, I felt more of an obligation to work on DotMail, but in reality I was never truly excited about making an email client my full-time job. Sure, I loved the challenge of thinking about it here and there, but I wasn’t madly in love with the intricacies of email technology.

In the end, this lack of passion impacted everything about DotMail. It's not that I was lazy, I was still putting in hundreds of hours of work and I was determined to get it done, but I was treating it as a side project not fully worth the risk. I never considered going 100% in on DotMail and investing all my time in it. I simply had commitment issues due to a lack of love for the type of product itself. I loved DotMail, but I didn’t love the idea of working on emails for the rest of my life.

All I had was a rudimentary version running on my computer, a manifestation of false hope.

All of this wasn't apparent at first, but I later knew that if I had really loved DotMail I would have tried many more times. I would have tried even harder to find the right partner. I certainly would have taken bigger risks, especially financially.

After a couple years of failing and pushing DotMail in front of me, we never achieved anything worth shipping. I grew tired of finding new people, motivating my partners (and myself) and wasting my time on it. I had to make a decision and either shut it down, or fully commit and give it one last chance.

About two years after the initial concept, I wrote a blog post about my decision. DotMail was dead, but was it ever alive? All I had was a rudimentary version running on my computer, a manifestation of false hope.

_____

Fast forward three more years and, still unsatisfied with email clients out there but now with much more experience under my belt, I gave it one last try. A promising developer and friend of a friend reached out to me and said he could and want do it, and that he would be able to commit a couple days a week to work on it. I was pumped, but we didn’t tell anyone about it. I wanted to spare myself the disappointment of publicly failing again.

We discussed the details, made a plan and got to work. Expectations were clear: We would both work on it on the side but we would keep a strict timeline, including regular check-ins every week. We knew it may take longer to finish, but now we had structure. We took my designs from 2011 and completely redesigned and refined them. I’m sharing a couple of them right here, for the first time.

We now had fresh motivation, we had a plan, we had designs we were excited about and more importantly, I could feel the potential. We stripped down the app to its core and planned out a realistic MLP (minimum lovable product) that we could launch within 10-12 months to family and friends. Nothing fancy, just something simple that runs purely on the Gmail API.

.Mail is back. Or maybe not.

But we failed, again. The excitement wore off after a couple months. My partner lost motivation and eventually dropped out of the project. I was mad and disappointed. Not at him, but at myself. I fucked up and I hated myself for it. I should have known better after all these years.

However, it was easier this time; no one knew we had secretly started working on DotMail again, so I didn’t have to apologize to anyone but myself. It took me only one night to sleep on it and I knew what I had to do.

Fuck it. Fuck DotMail.*

*But also thank you, I’ve learned so many things from you.

___

This was my (shortened) story of DotMail, the startup that never started. DotMail is only one of many projects I worked on that never saw the light of the day. Looking at all my projects, more than 50% never make it to the final stage. Dozens more, prototypes and sometimes even almost finished products, die on my hard drive. All of them have their own story. And despite the tears and anger, they were all worth it. They’re all failures that taught me a lesson or two.

You can still see the original concept here. And the updated version here.

Thank you for reading,
Tobias

P.S. I'd like to thank everyone who ever worked with me on DotMail. Even if we did not succeed, I'm thankful for the time you invested and the trust you gave the project. Thanks to my crew at les Avignons, Matthias for helping me with the DotMail landing page, Robert, Michael, Lu, Mike, Juergen and everyone I've bored over the years with my DotMail conversations. THANK YOU!