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Bootstrap First with Services from London, Raise Money Later: Rich Waldron, CEO of Tray.io (Part 3)

Posted on Tuesday, Jun 23rd 2020

Rich Waldron: There was one person who really liked us. The reason was, as a team, there is a clear CTO, a business person, and a product/CEO type. We had an interesting balance of skill sets. We were technically savvy. We were able to produce and build the things that we wanted to.

Even if our idea wasn’t necessarily in the right ballpark, we had real determination and a scrappy culture about us. They liked the fact that we weren’t prepared to quit. We kept plowing on.

As we came off the accelerator, we ended up on a well-known podcast that had picked up some interest in San Francisco. We had a funding round lined up with a pretty well-known investor who tragically passed away before the deal was complete. We had committed to moving to San Francisco as a result.

Our funding round fell through and we were facing really dire consequences. We spent the best part of the year without a salary ourselves. That incurred a fair amount of personal debt. Another option was to join a second accelerator in San Francisco which gave us a fair bit more capital so that we could make last at least 12 months. We finally went over to San Francisco. 

Sramana Mitra: When was this?

Rich Waldron: 2012. It was a busy year. We did three months and then we had the summer when it all started to explode. Then we moved to San Francisco in October and borrowed the money from my grandparents for our flights. We hopped on a plane and booked for three days in a hotel. That was a huge turning point for us.

The accelerator provided us with a great deal of value on two things. One is, it was less focused on heavy mentorship. It allowed us to do custom development and develop ourselves. It brought in really high-caliber people that could help with specific challenges like finding customers, pricing, or thinking about product-market fit.

It was during the accelerator that I’ve been writing all of this script that was powering the backend of our idea. Every action that a customer took, there was a script that was supporting us in the background.

We had a script which looped through everybody that ever signed up to this product. It did a comparison with the Angellist API. It looked to see if the person who would sign up was an infrastructure investor. It would then output that to a CSV. It built an automailer and try to arrange meetings.

That was the point when we realize that if we were to expand the vision of what we were doing and move it beyond email, this infrastructure play would be very interesting if we could empower people that were technically savvy to create what have now become workflows.

Many of the original aspects of our vision came through over the next eight years. We were just fortunate with how the world moved on.

Sramana Mitra: To respond to what you said about the accelerator that you were working with, we emphasize product-market fit. We emphasize a lot on strategy and positioning. How do you go about acquiring customers? How do you go about finding early adopters?

Talk to me about who were the early adopters of your concept and how did you find them?

Rich Waldron: There are two ways I’d respond to that. First, I completely agree that it is and should be the focus. It was our focus while we were on the accelerator. We set ourselves a target of doing 20 or 30 customer interviews a week.

We tried to keep a very open mind about all of the information that we had coming in. To our credit, the thing that we did well is that we were very open to change. We weren’t hell-bent on a specific idea. We were trying to learn every time we were engaging with people. 

This segment is part 3 in the series : Bootstrap First with Services from London, Raise Money Later: Rich Waldron, CEO of Tray.io
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