Building a Mid-Market Cyber Security Company from Utah: Peter Bookman, CEO of Guard Dog (Part 5)

Sramana Mitra: Not only that, it addresses my next question. The enterprise CISO right now is so overwhelmed. For a startup, to get an audience with an enterprise CISO has become almost impossible. There are the known players, but that’s about it. When it comes to the new players, they have to go through somebody. Mid-market doesn’t have that level of crowdedness.

Peter Bookman: Speaking specifically for cyber security, that ended up being what we drafted into. Listening is a very important skill. Always be quick to adapt. There was an interesting gap. Mid-market and small don’t tend to have CISO’s. They can’t afford them. I could go to the enterprise, but it’s uphill. They have a lot to manage.

Bootstrap First, Raise Money Later from Oregon: Paresh Patel, CEO of PayRange (Part 5)

Sramana Mitra: What happens next?

Paresh Patel: We started to prepare the company for scale. We had just received our Series A. We got $12 million in the bank. I first hired a COO and then a CFO. We opened up a new office. We messed up. We hired too fast and too big. Too many positions that didn’t really need to be hired for yet.

Sramana Mitra: Series A is more about how to build the product and how to sell the product.

Building a Mid-Market Cyber Security Company from Utah: Peter Bookman, CEO of Guard Dog (Part 4)

Sramana Mitra: Let’s come back to your story. Did Fusion-io go public?

Peter Bookman: It did. It was relatively smooth. A year and a half later, I left to start a virtual desktop company. That transacted again to another storage company Sandisk. I love listening to and solving a real problem. Whether we look at virtual private networks that are very prolific and common today as well as storage, they’re not in all of the cloud.

Sramana Mitra: What did you do after you left?

Bootstrap First, Raise Money Later from Oregon: Paresh Patel, CEO of PayRange (Part 4)

Sramana Mitra: The form factor of your product was that you would just clip it on a retail machine?

Paresh Patel: The design was remarkably simple. It almost works like a thumb drive. You just take the device and plug it into the machine. In three seconds, it could take that legacy machine and convert it into a modern mobile machine.

Sramana Mitra: A million and a half worth of orders were from how many customers?‘

Building a Mid-Market Cyber Security Company from Utah: Peter Bookman, CEO of Guard Dog (Part 3)

Sramana Mitra: In your case, the fact that you had a successful exit was helpful. Repeat founders always have an easier time raising money.

Peter Bookman: It does not hurt when your story can begin with, “I had a good horse and a good jockey. We won the race.” It does something else. You tend not to be alarmed, and you tend to be quite patient. It is fascinating that we got funding during that crisis.

Bootstrap First, Raise Money Later from Oregon: Paresh Patel, CEO of PayRange (Part 3)

Sramana Mitra: I’ve experienced the use case that you described. The gas station around the corner from me doesn’t have any digital payment option.

Paresh Patel: That was the problem. The machine only took cash.

Sramana Mitra: Do the gas station people attend these kinds of trade shows?‘

Building a Mid-Market Cyber Security Company from Utah: Peter Bookman, CEO of Guard Dog (Part 2)

Sramana Mitra: Did you work for SonicWall?

Peter Bookman: I did not. I transitioned out. I’m always excited about the next opportunity.

Sramana Mitra: What year was that?

Peter Bookman: 2001.

Bootstrap First, Raise Money Later from Oregon: Paresh Patel, CEO of PayRange (Part 2)

Sramana Mitra: What is your Ph.D. in?

Paresh Patel: It’s also in e-business and organization management.

Sramana Mitra: The vending machine company was yourself?

Paresh Patel: There were employees. We grew to about 25 employees.