Building a Mid-Market Cyber Security Company from Utah: Peter Bookman, CEO of Guard Dog (Part 1)

Peter is a startup veteran who is building a new Cyber Security company from Utah. The key insight to focus on in this story is how he found white space in the mid-market.

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?

Bootstrap First, Raise Money Later from Oregon: Paresh Patel, CEO of PayRange (Part 1)

Paresh did a superb job of validating in a bootstrapped mode and then raising significant venture capital. However, he made some mistakes after the fund raise. Eventually, he course-corrected and has built a wonderful business without further infusion of capital. Excellent case study!

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?‘

Bootstrapping by Piggybacking: Evenica CEO Sadek Ali (Part 6)

Sramana Mitra: If you tried to go into the Shopify marketplace with another e-commerce platform, that wouldn’t work. That was not an option. You were trying to build your own e-commerce platform.

Sadek Ali: Shopify is a long-tail play.

Sramana Mitra: Shopify, on many levels, is not the right marketplace for you.

Sadek Ali: Shopify and Shopify Plus are great products, but they’re not the best products for the mid-market.

Bootstrapping by Piggybacking: Evenica CEO Sadek Ali (Part 5)

Sramana Mitra: You had a diverse set of e-commerce platforms that were in that portfolio.

Sadek Ali: That’s correct. We didn’t really know what the platform was. I picked up technologies my entire life. If you understand how e-commerce works, then you know the operational side of it that they’re looking for. We did that and we said, “Let’s make sure our contracts are easy. Let’s make sure we have happy customers and let’s make sure we have a happy culture in this little group of three.”

They liked our hands-on approach and they liked being able to have an open and honest conversation about e-commerce. We got our three customers monetized right away. For two customers, it took us two years. We still had the contract for them, but they wouldn’t pay us a penny. We had to be persistent because we wanted that conversation with them.

Building a 2-sided Farm to Table Marketplace from Indiana: Nick Carter, CEO of Market Wagon (Part 5)

Nick Carter: We can prove a few things though. We had gross margin profitability. We’re not losing money on operations. We have been building a playbook for scale. We had practice with opening – what the regulatory problems are, how you find a space, who you need to recruit. They backed us with $5 million in the fall of 2020.

We raised even more in the summer of 2021 because the model that we had put together was based on variables that we really had no way of knowing how accurate they were. We finetuned it over the following six months. The money primarily went into customer acquisition. That and new geographies. Opening up a new geography doesn’t take a lot of capex. As I mentioned, we’re doing things very inexpensively without a warehouse. We do have to commit to about $100,000 in operating expenses and customer acquisition in order to get each hub up to a viability point.

Bootstrapping by Piggybacking: Evenica CEO Sadek Ali (Part 4)

Sramana Mitra: They replaced you as the CEO.

Sadek Ali: They tried to. I was the Founder and CTO. My business partner was the CEO. They hired a CEO.

Sramana Mitra: The business got replaced by their CEO.

Sadek Ali: Yes.

Sramana Mitra: That didn’t go well.

Building a 2-sided Farm to Table Marketplace from Indiana: Nick Carter, CEO of Market Wagon (Part 4)

Sramana Mitra: What happens when COVID strikes?

Nick Carter: Everything in our company is measured on week-over-week sales. I can remember my co-founder texting me one Sunday afternoon saying, “We had a nice week today.” The sales volume grew 600% in one week. It’s because everybody had to stay home. They needed delivery. The traditional supply chain could not keep up with the demand.

Bootstrapping by Piggybacking: Evenica CEO Sadek Ali (Part 3)

Sramana Mitra: You joined that other company, but you kept the software services that was going in parallel.

Sadek Ali: Correct. Then we ended the business when I went to New York. From there, I came home because I felt that I had enough experience to do my own raise with my own ideas. In this next company, I was doing crypto and all that stuff. I learned how to do a raise and had my biggest failure at that point. It was then that I finished my PhD.

Sramana Mitra: What didn’t work in crypto?