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.

Bootstraps First to $5M ARR, Raises $10M Later: Toucan Toco CEO Charles Miglietti (Part 1)

French entrepreneur Charles Miglietti tells the story of how he has bootstrapped first to $5M and then closed a $10M round recently.

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 a Tech Company by an English Major: Kevin Groome, Founder of Pica9 (Part 1)

Kevin has done an excellent job of bootstrapping his tech company without a tech background.

Inspiring story for many in his shoes.

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 a Marketplace: Sardor Umrdinov, CEO of Home Alliance (Part 4)

Sramana Mitra: Between 2016 and 2019, what are other strategic points that we should discuss in this interview?

Sardor Umrdinov: From the beginning, I would probably start with more structure till you reach the first $5 million to $10 million. After $10 million, it’s harder to scale if you don’t have the structure in place. The same thing goes for leadership.