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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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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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Bootstrapping From a Small Town in Denmark to $12 Million: Sebastian Peterson, 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 Peterson: 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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Scaling a Robust Enterprise Software Company from Chicago: FourKites CEO Matthew Elenjickal (Part 1)

Posted on Monday, May 20th 2019

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?

Matthew Elenjickal: I was born in the south of India in a state called Kerala. I did my undergrad in Chennai and then moved here to Chicago for grad school. I went to Northwestern and took Industrial Engineering and Management Science. It’s a two-year program.

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Bootstrapping a Niche E-Commerce Company: Modded Euros CEO Sean Dawes (Part 1)

Posted on Monday, May 13th 2019

This conversation is a comprehensive discussion on how to bootstrap a niche e-commerce venture with a lean team and effective use of inventory financing.

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?

Sean Dawes: I was born and raised in Philadelphia. I haven’t gone too far away from my hometown as my company is based out of West Chester, Pennsylvania, which is 20 or 30 minutes outside of Philadelphia.

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Building an Online Travel Company From Barcelona: Guillermo Gaspart, CEO of ByHours (Part 1)

Posted on Thursday, May 2nd 2019

European startups are fast gaining maturity. ByHours is a venture-funded company growing steadily and expanding globally. Read on for a wonderful story.

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?

Guillermo Gaspart: I was born here in Barcelona, Spain 40 years ago and am married with three kids. I’m the fourth generation of a hotel family business from Spain. My great grandfather was one of the founders of the first hotel groups here in Spain.

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Building a New Insurance Company From Scratch: Clearcover CEO Kyle Nakatsuji (Part 1)

Posted on Thursday, Apr 25th 2019

The insurance industry is archaic and offers much room for re-engineering. Kyle discusses how he is going about it.

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?

Kyle Nakatsuji: I was born in Milwaukee, Wisconsin. I was born and raised in the Midwest. I went to undergrad at a college in Wisconsin and then got a law degree and an MBA at the University of Wisconsin-Madison.

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