Bootstrap First with Services from London, Raise Money Later: Rich Waldron, CEO of Tray.io (Part 4)

Rich Waldron: Deep down, we weren’t that passionate about solving email. Email wasn’t a thing we had a problem with. We were being pushed to think through how you want to spend the next 20 years of your life.

Some of the bad traits from Europe that we’d picked up is pitching ideas that we thought would get funded and would perhaps lead to a quick exit than being something that genuinely moved you.

As we were going through this process, we had this challenge where we were ourselves to the bone. In your heart, you know that it’s not the thing that you want to be doing. We were very honest with ourselves and said, “We have enough capital to pay the three of us. It will cover us for a year. If this is our shot, what do we want to do?”

We were just obsessed with this idea. How do you take complex data challenges and build an easier interface? Everything that we had ever done, we were obsessed with how APIs worked and what they opened up. Being able to empower people to take advantage of this and provide the facilities of an engineer was critical.

As we left that, we didn’t really have product-market fit. This is potentially controversial. A lot of the concepts of lean startups, we didn’t really follow. We had a clear idea of the thing that we wanted to exist and why we thought it was important. As we spoke to people, we recognized areas where our product would work for.

When you set out to build something that allows people to create a very complex integration, it’s pretty hard to build an MVP because you can’t ever drop data. The basic feature set that you need to have to be competitive or, at least, to have a conversation is pretty high.

There was a blind faith in us saying, “We’re just going to build this regardless of everything else.” That isn’t necessarily how I’d recommend people set out to build a company. Because we were so passionate about it, it was going to get our full dedication. 

Sramana Mitra: When did you get your first customer? I take it that you went back to London?

Rich Waldron: We did. We couldn’t raise money. We went back to London with our tails between our legs because if you can’t raise money, you also can’t get a visa. We went back to London and were able to raise a small round. We raised around $300,000. We hired two engineers. One of which is still in the company today.

We set about building this product. In the first year, it was all engineering work. We stayed extremely lean. In fact, we stayed like that for a very long time. We, however, started to win these POCs and we’d learn these skills from our websites.

We ended up winning an integration contract for a bank in Europe. We built a Salesforce integration on our framework and road tested how we’d handle some of the enterprise challenges that come with that.

Our first customer was a pretty large bank that was using us for a POC for some automation between the account services team and the sales organization.

Sramana Mitra: How did you find them? 

Rich Waldron: We found them through cold emailing people. We would look for people with integration on their title in LinkedIn. We looked for certain type of Ops people. We would hustle and send out emails until somebody picked it up.

We would offer to do this work for free. We’d say, “We’ll do these pieces for free.” Eventually we found someone who said, “I have this thing we’re trying to solve at the moment. You’re welcome to come and apply.” We supported that for two years.

It didn’t ultimately last as a long-term contract but we learned so much about some of the key things that we needed to have in our platform. The next thing that we did that worked really is, we were introduced to many different organizations. Venture capitalists would say, “Go meet this team and go see if you can solve some problems for them.”

We found that to be fascinating. All of these organizations had huge pains in their own sales cycles, and they were trying to sell their products. The end customer would say, “This needs to connect to our customers. It needs to pull data from this.” We ended up becoming this really nice way for them to solve what was a difficult challenge in their own process.

As a result, we began to pick up some great customers through this referral process. At every stage, we were learning more and more about the breadth of challenges in this space. We spent the best part of four and a half years purely focused on engineering and having this extremely scrappy culture.

We ended up having an extremely mature and robust platform. The go-to market came later. When it did, we just had this great synergy that worked well for us.

This segment is part 4 in the series : Bootstrap First with Services from London, Raise Money Later: Rich Waldron, CEO of Tray.io
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