Bootstrap First with Services from London, Raise Money Later: Rich Waldron, CEO of Tray.io (Part 2)

Sramana Mitra: Talk to me in a bit more granular form what was going on. What kind of web development were you doing? What was the product idea that you were noodling with and then building?

Rich Waldron: In hindsight, providing services alongside product development was really important. We got a crash course in having to manage our own finances.

As you go through venture rounds, having a grip on that and having experience on its challenges is good. I left my job about three years in. I did it in not particularly a smart way. I hadn’t saved up any cash. I probably had a month’s rent in the bank.

I had this burning desire to start building again and build something on my own. I teamed up with my co-founder and we set about winning some local web projects. We would build websites and web applications for local businesses without having any real experience on what we were doing.

We would go in and get on top of these big pitches. We ended up winning some pretty big logos. We had Krispy Kreme as a customer. We were trying to build up a few things. Number one was, we needed some capital to be able to cover our own personal runway.

Number two is, we needed more engineers and more designers. We had to do it ourselves. We had this web company. In hindsight, we didn’t really run it particularly well because we didn’t build the pipeline to win the next contract. It became a full-time challenging job to keep this running.

We shut it down and allowed the team that worked with us to carry on servicing the customers and take on the business as it were. When Alastair joined, the three of us moved to the local area. We sold Wellington boots out of the warehouse for the next 12 months as a way of having an income that would pay the bills and allow us to keep working.

We were the definition of bootstrapping. What that brought us was some thinking time to be able to focus on what we wanted to build and how we wanted to do it. We had this background process where we were selling Wellington boots on eBay. It was providing just enough for us to cover our rent. We were able to focus on what we were doing.

The company that we set up in the UK is called Plan.nr. The thinking here was that trying to arrange to do something in a group was extremely difficult. You would spend forever trying to decide on where you’re going to go, what you’re going to do.

We built this application for decision-making. You can send it out to your friends and family. It would allow you to create these multiple choice polls on an iOS app. In hindsight, we never stood a chance because we had no cash to put behind it. Building a consumer business is extremely difficult.

What we were trying to do is reduce these long email threads. It would get unwieldy. It was during the process of building this app that we decided to focus on how we could tackle this problem at the email level. That really was the beginning of Tray.

We built an API service that allowed you to write email rules that’s connected to your inbox and write these workflows so you could triage and act on emails as it came in based on the rules engine that you built. You’ll be able to connect into all these services and be able to manage the workload of what occurred during email. That was in 2012.

I was getting sick of picking out Wellington boots and taking them to the post office three times a week. We saw an opportunity to join an accelerator in London. The big draw for us was we would have access to Google’s campus. We felt that we would get three months where we could focus on the challenge that we’re trying to solve and build out a product.

We applied for that. We were, fortunately, accepted. We moved out to London and began building the product. As we went through that process, we were able to explore a little bit more and start to get some early traction going. 

This segment is part 2 in the series : Bootstrap First with Services from London, Raise Money Later: Rich Waldron, CEO of Tray.io
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