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Entrepreneur Journeys

Building Two Open-Source Startups in a Row: Sysdig CEO Loris Degioanni (Part 1)

Posted on Tuesday, Jul 9th 2019


Loris has specialized expertise in building Open Source companies. Read how he has done it twice.

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?

Loris Degioanni: As you can tell from my accent, I wasn’t born in the United States. I was born in Italy. I was born in a unique part of Italy. I was raised in a little town called Menaggio in one of the mountain valleys connecting Northern Italy and Southern France.

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Building Businesses in Aftermarket Designer Merchandise: ShopWorn CEO Richard Birnbaum (Part 1)

Posted on Friday, Jul 5th 2019


Richard has built several business in the “shopworn” designer merchandise segment. Learn more about the business through his journey.

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?

Richard Birnbaum: I grew up in Brooklyn, New York. I was born into a family of merchants. My father taught me at a young age that everything is about value. Even when we’d go to a diner as a kid, he couldn’t go on raving enough about what a great deal it is they’re offering us. He’d say, “We get a salad. We got Jell-O for dessert.” He instilled in me, at an early age, that it’s all about value and giving the customer a great deal.

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Best of Bootstrapping: How FormAssembly CEO Bootstrapped a Virtual Company with a Paycheck

Posted on Friday, Jun 21st 2019

Cedric’s story is a textbook case study of the kind of entrepreneur we want to see emerge and grow in every corner of the world: a solo entrepreneur who is a developer and a product guy capable of getting to validation while holding onto a day job. Today, FormAssembly CEO Cedric Savarese has almost 50 employees spread around the world, and while it maintains a small office of fewer than 10 people in Indiana, the bulk of the company has scaled as a virtual workforce. Excellent model, and I encourage aspiring entrepreneurs to read this carefully.

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?

Cedric Savarese: I was born in France and expatriated to the US. I grew up in a small town not so far from Paris.

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

Posted on Friday, Jun 14th 2019

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 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.

We’re a middle class family from India. There was a lot of support and pressure for doing well in education. I appreciate my parents for doing that, but there was always the push to find something that you really like to do. I still remember my parents telling me many times as a child that I’ve got to find something.

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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 2019

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 your journey. Where are you from? Where were you born and raised? What kind of background?

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

Posted on Friday, May 31st 2019

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 at universities overseas both in Canada and Japan for a little while. It was this time when I was abroad spending time in different countries that I was exposed to different business models, cultures, and people.

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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 2019

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 born, raised, and in what kind of background?

Sebastian Petersen: I’m from Denmark. I would say I had a pretty ordinary background. Both my parents were working in the public sector. I’ve always had an entrepreneurial spirit together with one of my best buddies growing up. We were always together.

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

Posted on Monday, May 27th 2019

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: What you’d hear in my journey is a great example of the American dream. I was born in Cairo, Egypt. My mother is German and my father is Egyptian. He was a criminologist.

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

Posted on Friday, May 24th 2019


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 background? 

Josh Kamrath: I was born in Phoenix, Arizona. I lived there until I was 12. Then my family moved to Colorado, which I consider my home. I grew up there and went to college at Colorado State University where I met my wife Josie. She’s from California. I graduated a year ahead of her.

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

Posted on Friday, May 24th 2019

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.

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