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Bootstrap First with Services from London, Raise Money Later: Rich Waldron, CEO of Tray.io (Part 1)

Posted on Sunday, Jun 21st 2020

Rich is building an authentic tech company from London and while the company could have become a so-called Unicorn by loading up on liquidation preferences, they have chosen not to do so. Excellent story.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Rich Waldron: I was born in the UK in a place called Southampton, which is right down on the South Coast. It’s most famous claim to fame is where the Titanic set off from. I was born there 35 years ago.

Sramana Mitra: What about your education? Where did you study?

Rich Waldron: I studied locally. I went to university in Bournemouth which is just down the coast. It’s a reasonably well-known university. It has an excellent digital and engineering foundation to it. 

Sramana Mitra: What did you do after you finished that program?

Rich Waldron: It’s actually when I met one of my co-founders Alastair Russell who was at Southampton University. He was in Tim Berners-Lee’s website team doing research. I finished in 2006. The job market was pretty tough.

We spent the summer building some of our own ideas and trying to get a few different things off the ground. Ultimately I ended up becoming a product manager at a company not too far from where I grew up. I spent three years there. I got a crash course of what it’s like to be part of a really small team and what it’s like to manage an engineering culture.

Ultimately, I led a sales team. I had a pretty interesting purview into many different departments and scaling out different teams along the way.

Sramana Mitra: When did you start this company?

Rich Waldron: We started the company in 2012. However, the three of us started working together a couple of years before that. Myself and the CTO had been building products together for years. The area that we’re from in the UK just doesn’t have a technology scene. There isn’t a local investor network. Technology companies aren’t built there.

The three of us started the company in 2012 having spent a number of years running a web agency together as a way to fund some of our initial products. We used some of the proceeds from that to say, “Let’s build out an application.” We were particularly naive when we did it. 

Sramana Mitra: Let’s talk a little bit about those very early days. What you’re describing is a piece of methodology that we use in our accelerator that is very controversial. This is the notion of Bootstrapping with Services. In the classic Silicon Valley world, they don’t like this model.

We do. We’ve seen company after company become very successful following this. What you said that you were doing web development to fund your product development is something that we are big believers in. 

This segment is part 1 in the series : Bootstrap First with Services from London, Raise Money Later: Rich Waldron, CEO of Tray.io
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