Bootstrapping a Tech Company by an English Major: Kevin Groome, Founder of Pica9 (Part 6)

Sramana Mitra: What’s the next major inflection point?

Kevin Groome: The introduction of Campaign Drive. We kept on building the software and getting more of our legacy customers over to the SaaS platform, which was an enormous risk point. By 2014, we were able to say that we had 90% of our legacy customers on our new SaaS platform.

Sramana Mitra: When did that finish?

Bootstrapping a Tech Company by an English Major: Kevin Groome, Founder of Pica9 (Part 5)

Sramana Mitra: How many clients did you have in 2007?

Kevin Groome: Brands under management were 40. Billing relationships were probably 15.

Sramana Mitra: What kind of revenue level were you at?

Kevin Groome: We were at around $1.6 million in subscription revenue. We used to call ourselves an ASP.

Bootstraps First to $5M ARR, Raises $10M Later: Toucan Toco CEO Charles Miglietti (Part 4)

Sramana Mitra: What else is interesting in your strategy?

Charles Miglietti: What we are building right now. We are building a series of ready-to-use applications that will be plugged into existing systems. As we provide the very top layer of the visualization, we can build business applications that rely on any existing ERP or any existing system.

In terms of strategy, we have a vertical approach to target specific businesses that use a specific system.

Bootstrapping a Tech Company by an English Major: Kevin Groome, Founder of Pica9 (Part 4)

Sramana Mitra: How big was that deal with Marriott?

Kevin Groome: At that time, not that big. It was less than $100,000 a year. They are now our largest client. They spent probably $30 million with us.

Sramana Mitra: $100,000 for a small company year-over-year is not a small amount of money.

Bootstraps First to $5M ARR, Raises $10M Later: Toucan Toco CEO Charles Miglietti (Part 3)

Sramana Mitra: Once you hit this limit and you realized that you had to do something else, what did you do?

Charles Miglietti: We looked at our customer base. We identified the pattern in terms of persona and use case. We kept only the good ones – the ones that were repeatable.

Sramana Mitra: What did you decide to focus on at this point?

Bootstrapping a Tech Company by an English Major: Kevin Groome, Founder of Pica9 (Part 3)

Sramana Mitra: Let me start driving you towards the entrepreneur journey story. When you decided to launch this, who developed the software? How did you finance the software development and getting to a product?

The idea came from a particular client situation where you experienced this problem. You have an understanding of the pain point. But how did you get yourself off the ground?

Bootstraps First to $5M ARR, Raises $10M Later: Toucan Toco CEO Charles Miglietti (Part 2)

Sramana Mitra: Let’s talk about that journey. When did you start looking for customers? What did you have? Did you have an MVP?

Charles Miglietti: We sold the first pilot. There was no MVP. We built the MVP with our first customer. 

Sramana Mitra: What was the problem that you were solving for this customer?

Bootstrapping a Tech Company by an English Major: Kevin Groome, Founder of Pica9 (Part 2)

Sramana Mitra: How long did you stay in that advertising agency?

Kevin Groome: In 1998, I began to make a transition. There were two reasons why. One was we began to see that the advertising business was shifting. Even then, we could feel that the advertising industry’s old model, which was formed in the 60’s, was beginning to change.