Bootstrapping an AI-Powered Security Startup to $10M+ in Revenue: Osprey Security CEO Rohit Anabheri (Part 4)

Sramana Mitra: These two customers that you were able to place the MVPs into pilots with, how long did it take you to turn them into paying customers?

Rohit Anabheri: About three to six months. They wanted to ensure the stability of the platform.

Sramana Mitra: What is the average deal size?

Rohit Anabheri: Six figures.

Bootstrapping an AI-Powered Security Startup to $10M+ in Revenue: Osprey Security CEO Rohit Anabheri (Part 3)

Sramana Mitra: How long did it take you, and what was the trajectory? How many customers did you work with in the beginning? As you started to productize, what was the timeline?

Rohit Anabheri: The first year is always a struggle. It was completely bootstrapped by me and my co-founder.

Bootstrapping an AI-Powered Security Startup to $10M+ in Revenue: Osprey Security CEO Rohit Anabheri (Part 2)

Sramana Mitra: Did you have a customer with whom you validated this with?

Rohit Anabheri: This has been my mantra. Find your customer. Know their problems and fix their problems. We did it very organically. We knew what the gaps were. Then what we did is documented them and went to the people to validate.

Sramana Mitra: Who are these people?

Bootstrapping an AI-Powered Security Startup to $10M+ in Revenue: Osprey Security CEO Rohit Anabheri (Part 1)

Rohit has effectively used the Bootstrapping Using Services technique to bootstrap an AI-Powered Enterprise Security venture to mid eight figure revenues. In that process, he has turned down offers for Venture Capital. I believe, in Artificial Intelligence and Machine Learning, currently, Bootstrapping Using Services is one of the best ways to find problems to solve and build successful companies.

Non-Technical Founders Building a Venture Scale SaaS Company: Sendoso CEO Braydan Young (Part 5)

Sramana Mitra: When you made that decision to bring in an enterprise, you were feeling this tension. Did you add to enterprise customers?

Braydan Young: We added.

Sramana Mitra: I thought that’s what you would be doing. People want more enterprise customers.

Braydan Young: We looked at churn. We could look and see who’s doing the sending in the platform. Mid-market enterprises were consistent senders. They would send all the time. You can close SMB faster, but they can’t influence your roadmap.

Non-Technical Founders Building a Venture Scale SaaS Company: Sendoso CEO Braydan Young (Part 4)

Sramana Mitra: The reality is that you were in revenue when you went out to raise. That makes things a lot simpler. The fact that you spent a year fine-tuning your model to the point where you were a recurring revenue-generating business makes raising money a lot simpler.

Braydan Young: The one thing going against us was that we were both salespeople. A lot of the questions were about our technical co-founder.

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Non-Technical Founders Building a Venture Scale SaaS Company: Sendoso CEO Braydan Young (Part 3)

Sramana Mitra: To me, calling sounds like a mistake.

Braydan Young: Yes. It would have been way better to have a marketing campaign or have a landing page. The knowledge I had was only coming from sales back then. It was brute force.

Sramana Mitra: Unless there is a substantial deal size of at least $10,000 or so, calling doesn’t really work.