Osprey Security Founder Rohit Anabheri had effectively used the Bootstrapping Using Services technique to bootstrap an AI-Powered Enterprise Security venture to mid eight figure revenues when we spoke in 2023. In that process, he had turned down offers for venture capital. Sramana Mitra: Let’s start by introducing our audience to yourself and then we’ll come
Sramana Mitra: What is your funding strategy? We talked about the $2.2 million round. What else have you done since then? Rich Waldron: We’ve raised a total of $109 million now. We raised a $5 million bridge to a Series A. In 2016, we raised our Series A which was $14 million in March of
Sramana Mitra: Talk to me about your go-to market strategy. What has worked? What turned out to be the repeatable customer acquisition strategy? Rich Waldron: For a long time, we were relying on partner referrals. To this day, they still make up a healthy portion of our go-to market. To really stand on your own
Sramana Mitra: By the time you raised money, what did you have? Rich Waldron: We raised a $2.2 million round in December of 2014. That was the first institutional check. Prior to that, we had some capital from the accelerators and we raised a small angel round off the back of that. Sramana Mitra: How
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
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
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
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