Best of Bootstrapping: Bootstrapped Decisively to Over $5M

RainmakerForce CRO Mack Sundaram had built a successful business optimized for autonomy and profitability when we spoke in 2018, and the company was acquired in 2023. Excellent navigation!

Sramana Mitra: Let’s go to the very beginning of your journey. Tell us where you’re from. Where did you grow up? Where were you born and raised?

Mack Sundaram: I was born in South India in a village near Chennai. I spent some time of my childhood in Chennai and Pondicherry. I later went to school in New Delhi. Since then, I moved over to the United States where I had an opportunity to pursue a doctoral degree in Economics. That’s where the transition happened.

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Best of Bootstrapping: Bootstrapped a Cybersecurity Venture with a Paycheck

Christian Geyer convinced the board of his employer to let him incubate a cybersecurity startup idea as a division of the company with an express intent of spinning it off. Now, ACTFORE has been spun out, doing almost $20M in bootstrapped annual revenue, and may soon find a lucrative exit. This is a phenomenal story for entrepreneurs considering the Bootstrapping with a Paycheck route.

Sramana Mitra: All right, Christian, let’s start at the very beginning of your journey. Where are you from? Where were you born, raised? What kind of background?

Christian Geyer: Well, I was born and raised in Reston, Virginia. I’m almost what I would consider a homebody. So, I’ve pretty much lived in Reston, Virginia. The only time I left was for college. I’m very centrally focused on family. My business is in Reston, Virginia, just a few miles from my actual childhood home and my current home.

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Seedstrapping to Exit

In 1Mby1M, we like Seedstrapping to Exit. An example would be Adya’s acquisition by Qualys. Adya raised a small seed round. I introduced them to Philippe Courtot, CEO of Qualys. Qualys acquired Adya.

For our Seed Capital series of podcasts, I’ve interviewed hundreds of investors, especially micro-VCs and angels who play an important role in the early-stage game. 

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Best of Bootstrapping: VC-Funded Venture After Bootstrapping to Exit

A very effective way to dance the entrepreneurial Waltz is to do a bootstrapped company first, sell it, and then do another venture with a more ambitious agenda. From 2021, Jeremy Swift’s journey as Co-founder and CEO of Cordial is a great case study of this method.

Sramana Mitra: Let’s go to the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Jeremy Swift: I was born in Beaverton, Oregon. Most people know about Beaverton because of Nike. It’s a small suburb outside of Portland. I grew up in what I would consider a small middle class family. Both my parents were a rare breed and especially different from the path that I’ve taken in my life. The first job they got out of college is the same job that they retired with 40 plus years later.

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We Like Bootstrapping to Exit

This week, we’re discussing how the Age of AI is also the golden age of Bootstrapping, and also of Solo Entrepreneurship. Yes, you CAN and SHOULD bootstrap with a Paycheck. Yes, you CAN and SHOULD bootstrap to an Exit.

Are you trying to do a startup as a SOLO entrepreneur? Your time has come.

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Bootstrapping a High Growth Cyber Security Venture with a Paycheck: Christian Geyer, CEO of ACTFORE (Part 7)

Sramana Mitra: So you have a bootstrapped company that is looking to go bootstrapping to exit straight away. Now, what is the ideal acquirer for this business? Is it a private equity firm?

Bootstrapping a High Growth Cyber Security Venture with a Paycheck: Christian Geyer, CEO of ACTFORE (Part 5)

Sramana Mitra: Wow. So, by this time you have spun out into a separate entity?

Christian Geyer: Not yet.

Sramana Mitra: Not yet. So, this $18.3 million is happening within, as a subdivision of the original company. Okay, and you’re probably making a lot more money than the original company, right?

Bootstrapping a High Growth Cyber Security Venture with a Paycheck: Christian Geyer, CEO of ACTFORE (Part 4)

Sramana Mitra: How much did get paid by this customer that gave you the first use case?

Christian Geyer: I believe it was $300,000.

Sramana Mitra: And this $300,000 came into the original company?