Best of Bootstrapping: Bootstrapped and Pivoted from the US Midwest

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page.  Co-founder and CEO Paroon Chadha has bootstrapped Passageways from Indiana, now doing business as OnBoard based in Milwaukee, Wisconsin, and he wants to help other regional entrepreneurs succeed. Along the way, he has pivoted from licensed software to cloud software, and made other strategic decisions

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Best of Bootstrapping: Bootstrapping OnBoard from the US Midwest

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  Co-founder and CEO Paroon Chadha has bootstrapped Passageways from Indiana, now doing business as OnBoard based in Milwaukee, Wisconsin, and he wants to help other regional entrepreneurs succeed. Along the way, he has pivoted from licensed software to cloud software, and made other strategic decisions that

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Best of Bootstrapping: How Passageways CEO Paroon Chadha Bootstrapped from Indiana

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 decisions that helped his company become more successful. Read on to learn more on his moves.

Bootstrapping from Indiana: Passageways CEO Paroon Chadha (Part 7)

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

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Bootstrapping from Indiana: Passageways CEO Paroon Chadha (Part 6)

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

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Bootstrapping from Indiana: Passageways CEO Paroon Chadha (Part 5)

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

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Bootstrapping from Indiana: Passageways CEO Paroon Chadha (Part 4)

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

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Bootstrapping from Indiana: Passageways CEO Paroon Chadha (Part 3)

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

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