Bootstrapping a Tech Company by an English Major: Kevin Groome, Founder of Pica9 (Part 7)

Sramana Mitra: I’d like to cover this CEO transition, which is always a tricky thing to do. For founders to let go and bring on a new CEO is a tricky transition. How did you do it? What wisdom do you have to offer for people who are trying to do that?

Kevin Groome: Let go of the suspicion that you’re irrelevant. For so many years, I felt like Pica9 was my fourth child and the most troubling of them all. Letting go of that and letting the organization stand on its own two feet can’t happen if I’m constantly doubting itself. Trust is huge – the trust in the whole organization.

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?

Best of Bootstrapping: From a Small Town to $12 Million

What a wonderful story of an ecommerce company bootstrapping to $12 million from a small town called Horsens in Denmark. All of the 60 employees working under TrendHim CEO Sebastian Petersen work out of Horsens currently.

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?

Sebastian Petersen: I’m from Denmark. I would say I had a pretty ordinary background. Both my parents were working in the public sector. I’ve always had an entrepreneurial spirit together with one of my best buddies growing up. We were always together.

We knew when we were 15 that we wanted to build something on our own. I tried different things when I was young. That’s how I started. I went to a regular high school. I thought I was going to be an engineer. I quickly found out that’s not what I wanted to do.

>>>

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?