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Billion Dollar Unicorns

1Mby1M Entrepreneur Bootstrapping an AI Deep Learning Venture to over $5M ARR: Bharath Gaddam, CEO of Data Poem (Part 1)

Posted on Monday, Jul 7th 2025

It is always thrilling for me to listen to 1Mby1M entrepreneurs achieving great things. This interview capture’s Bharath’s 6-year journey of bootstrapping to over $5M ARR. At this point, I am fairly confident that Data Poem can blitzscale to become a legitimate Unicorn. Not fluff, not fumes, clear, concrete ROI-driven revenue growth that is set up for repeatability and velocity. 

This is a text book case study of the 1Mby1M Bootstrap first, raise money to Blitzscale later philosophy. I have no doubt that VCs are going to salivate to get into this rocket.

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Building a Legitimate, Profitable FinTech Unicorn Using AI: Cynthia Chen, Founder of Kikoff (Part 5)

Posted on Friday, Jul 4th 2025

Sramana Mitra: How much did you raise in your first round?

Cynthia Chen: First round was $2.5 million.

Sramana Mitra: What milestone did that get you to?

Cynthia Chen: It got me to tens of thousands of active users.

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Scaling to $500M in Revenue: ModMed CEO Daniel Cane (Part 1)

Posted on Friday, Nov 15th 2024

I first spoke with Dan a decade back. Here is the story. This conversation offers insights on his scaling strategy with ModMed.

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Building a Bootstrapped Unicorn from India: Rajesh Jain, Founder of Netcore Cloud (Part 7)

Posted on Monday, Aug 12th 2024

Sramana Mitra: If you study Adobe’s product strategy, it’s basically a MarTech rollout. You can do the MarTech rollout. Given where we are, if you focus on companies that have more of an AI nuance to really build a cutting edge MarTech AI rollout, I think you have a very interesting opportunity in front of you.

Rajesh Jain: There is one more dimension to this. Compared to AdTech, MarTech has sort of been the poor cousin. About $500 billion is being spent on AdTech for new customer acquisition and existing customer reacquisition. Half of that money is basically being wasted on wrong acquisitions and reacquisition.

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Building a Bootstrapped Unicorn from India: Rajesh Jain, Founder of Netcore Cloud (Part 6)

Posted on Sunday, Aug 11th 2024

Sramana Mitra: Can you double click down on your three acquisitions and talk a bit more about how you price these deals? If you’re using stock, then how do you price yourself and calculate how you price the valuations of these acquisitions? Talk about the philosophy and the mechanics of doing these deals as a bootstrapped company.

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Building a Bootstrapped Unicorn from India: Rajesh Jain, Founder of Netcore Cloud (Part 5)

Posted on Saturday, Aug 10th 2024

Sramana Mitra: So this is happening 2015 onwards?

Rajesh Jain: So 2015 onwards, we did the international story and the marketing automation stack. I think we made a mistake on the marketing automation side. Now when I look back in hindsight, I think we focused more on the web and missed out on the app revolution.

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Building a Bootstrapped Unicorn from India: Rajesh Jain, Founder of Netcore Cloud (Part 1)

Posted on Tuesday, Aug 6th 2024

Rajesh Jain has built a Bootstrapped Unicorn from India. This is an important case study for all the bootstrapped entrepreneurs out there looking for inspiration and methodology to scale.

Sramana Mitra: Alright, Rajesh, let’s start at the very beginning of your journey. Where are you from, where were you born, raised, what kind of background?

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The Startup Velocity Question: Is it the Market?

Posted on Monday, Apr 15th 2024

Entrepreneurs often bet on markets that are yet to develop.

Good entrepreneurs often create new markets. Steve Jobs CREATED the smartphone market.

VCs bet on such bets.

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