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Best of Bootstrapping: How RainmakerForce CEO Mack Sundaram Bootstrapped Decisively to $5 Million+

Posted on Friday, Jun 14th

Mack has built a successful business optimized for autonomy and profitability. 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

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Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep (Part 1)

Posted on Tuesday, Jun 11th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  Ryan took a hobby project that he bootstrapped with a paycheck and managed to get into YCombinator. From there, he raised a $10M Series A from a top-tier Silicon Valley firm, Emergence Capital. Excellent execution thus far. Sramana Mitra: Let’s start from the very beginning of

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Best of Bootstrapping: How SmartBuyGlasses CEO David Menning Bootstrapped to $50 Million

Posted on Friday, May 31st

David has bootstrapped a global e-commerce venture from Hong Kong. Splendid execution! 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? David Menning: I grew up in Sydney. I’ve been educated in Australia. In my later years, I studied

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Bootstrapping From a Small Town in Denmark to $12 Million: Sebastian Petersen, CEO of TrendHim (Part 1)

Posted on Wednesday, May 29th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  What a wonderful story of an ecommerce company bootstrapping to $12 million from a small town called Horsens in Denmark. All 60 employees work out of Horsens currently. Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you

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Taking a Capital Efficient Company Public and Beyond: Medidata CEO Tarek Sherif (Part 1)

Posted on Monday, May 27th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  We’ve covered Medidata in TLHIT before. This time, we look at the entrepreneurial journey of this wonderful company. Sramana Mitra: Let’s start at the very beginning of the journey. Where are you from? Where were you born, raised, and in what kind of background? Tarek Sherif:

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Capital Efficient Entrepreneurship: Bongo CEO Josh Kamrath (Part 1)

Posted on Friday, May 24th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  Bongo has turned a ~$1M investment into $6M+ in annual revenue with a compelling growth projection in the next couple of years. Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born and raised? What kind of

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

Posted on Friday, May 24th

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.

Scaling a Robust Enterprise Software Company from Chicago: FourKites CEO Matthew Elenjickal (Part 1)

Posted on Monday, May 20th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  This is a terrific case study of smart execution on a complex domain by an entrepreneurial team. Read on ! Sramana Mitra: Let’s go back to the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background?

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