Paroon Chadha: There is a nuanced point that I’m trying to make here. I love Chris like a brother. He has worked with me for 10 years. I don’t think there will be another person who’ll ever be smarter than him. At the same time, what we needed at that time was not something we
Sramana Mitra: It sounds like when you did the cloud strategy, you almost did it with a different product. Even though the technology was the same, the positioning was quite different. The board technology was for the cloud software. Paroon Chadha: As an organization, we made the jump from being a Windows company to a
Paroon Chadha: We started to see some cross-pollination. We were pulling some leads that we didn’t really plan for. It was a little bit organic. We needed to move out of financial because the financial sector was stalling. We found ourselves selling in hospitals with some success. Then we ran into a very interesting founder
Paroon Chadha: If one has to learn a business, you’d rather start out from where your foundation is good. Raising capital and accelerating based on your balance sheet is a thing you can do anytime. If you have a solid core business, it’ll happen. The reverse of that is not possible. If you fund your
Sramana Mitra: This was 150 users through that credit union customer? Paroon Chadha: Yes. Sramana Mitra: You had one anchor customer and you had a software that was receiving feedback from the beginning. Paroon Chadha: Chris was writing code, and I was out selling. We didn’t fear anything at that time. I wish I could
Paroon Chadha: You are never going to be surrounded by so many super smart and super open people in your life. When you’re at school, there are a lot of engineers and computer scientists. There are a lot of people who are good at math. You can pretty much come up with any idea and
Paroon has bootstrapped Passageways from Indiana and wants to help other Indiana entrepreneurs succeed. Along the way, he has pivoted from licensed software to cloud software, and made other strategic decision that helped his company become more successful. Read on to learn more on his moves. Sramana Mitra: Let’s go to the very beginning of
Sramana Mitra: I’ll tell you exactly what happened in your case. You did a Bootstrap First, Raise Money Later strategy. You were going out to raise Series A with $2 million in revenue. You went out to raise Series B with close to $10 million in revenue. These are funding situations where a company that