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Entrepreneur Journeys

Successful Pivot from B-to-C to B-to-B: Inkling CEO Matt MacInnis (Part 1)

Posted on Monday, Jan 16th 2017

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Here’s another pivot story. Note: pivots are very expensive to do in VC timeline and cap tables. Matt discusses how damaging the ownership structure has been. Worth understanding the ramifications.

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?

Matt MacInnis: I’m from Nova Scotia, Canada. I’m from a small island in the northeast, 300 miles to the nearest airport. My mom was a school teacher and my dad was a factory worker. We had a pretty good upbringing up there. It was a little bit cold in the winter. I ended up getting into Harvard somehow from that little town. We had to find a way to make that work. My parents, very graciously, gave their retirement savings to make that work. >>>

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Bootstrapping With a Paycheck to TechStars: Nevin Shetty, CEO of Blueprint Registry (Part 1)

Posted on Monday, Jan 16th 2017

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In a previous story, we showed you how Jas Grewal bootstrapped his company CareSkore with a paycheck and then got into YCombinator with a validated business. In this story, we show you the same strategy as executed by Nevin Shetty to get into TechStars.

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?

Nevin Shetty: I was born in Alabama but the first memory I have is of Saudi Arabia. I spent five years in Saudi Arabia. My dad is an aeronautical engineer. I grew up in an American compound in Riyadh and had an amazing childhood. Growing up, I remember my mom teaching English to some of the Saudi princes. >>>

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Managing a Successful Pivot from B-to-C to B-to-B: Jifiti Co-Founder and CMO Shaul Weisband (Part 1)

Posted on Monday, Jan 9th 2017

Jifiti started life as a B-to-C gift-giving service. That didn’t work. Read how they maneuvered their way to a successful B-to-B business.

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

Shaul Weisband: I was born the United States. I moved with my family, when I was seven, to Israel. Israel is pretty much where I was raised and went to school. That’s where I founded our company Jifiti at the end of 2011. Our development and operations teams are still there. Our US office is based in Columbus. That is where I relocated with my business partner around four years ago to head our local offices here in the US and focus on our business development and marketing. >>>

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Raising Funding on AngelList: Contactually CEO Zvi Band (Part 1)

Posted on Monday, Jan 2nd 2017

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Zvi has raised several rounds of financing on AngelList in the process of building Contactually. Among other things, his experience with the platform is interesting in this interview.

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

Zvi Band: I was born in Boston. I was mainly raised on the West Coast. Then my family moved to the DC area to follow my father’s career. I’ve been now a DC resident for the past 15 years. I would qualify myself as a builder. As a kid, I always had Legos in my hands. Legos turned into software and software turned into companies. >>>

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Building a Fast Growing FinTech Company from Utah: MX CEO Ryan Caldwell (Part 1)

Posted on Monday, Jan 2nd 2017

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Ryan self-financed, with some seed money, a FinTech company selling to small financial institutions. Today, the company has delivered 185% y-o-y growth for five consecutive years.

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?

Ryan Caldwell: I was born in Berlin, Germany. My father was a lawyer in the military. He was stationed in Germany at that time. My older brother and I were both born in Germany.

Sramana Mitra: What did you do for college? >>>

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Building a Big Data Venture: Hiro Yoshikawa, CEO of Treasure Data (Part 1)

Posted on Monday, Dec 19th 2016

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A very interesting story of a big data infrastructure management startup.

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?

Hiro Yoshikawa: I am a native Japanese. I was born in Tokyo in 1978 and was raised on the outskirts. Even when I was a very small kid, I loved literature. Mostly, I like Japanese novels like Murakami. Do you know Murakami?

Sramana Mitra: I do. Were you reading in Japanese or in English? >>>

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Diamond Auctions Online: Benny De-Kalo, CEO of Worthy.com (Part 1)

Posted on Monday, Dec 12th 2016

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I recently had dinner in Berlin with Alex and Suzi Zache, founders of Auctionata, an online auction house that has scaled to over $150 million in revenue. You can refresh that story here. Here’s another online auction story that is scaling nicely as well, specifically in diamond auctions. The company is at over $50 million in revenue.

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?

Benny De-Kalo: I was born in Tel Aviv, Israel. I moved to New York after the military service, which is mandatory in Israel. I went to school in New York and >>>

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Bootstrapping to $15 Million in Three Years: Connatix CEO David Kashak (Part 1)

Posted on Monday, Dec 5th 2016

Extraordinarily tight, disciplined strategy and execution has enabled David to build a tremendously fast growth company with a small team. A lot to learn!

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 Kashak: I was born in Israel. I grew up in Israel and studied engineering at Tel Aviv University. After studying, I started as a programmer in a cyber security company in Israel. At one point, they offered to relocate me to New York. That offer was very interesting because I wanted to get more exposure to business. I moved to New York. >>>

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Bootstrapping Using Services: James Kane, CEO of RWS (Part 1)

Posted on Monday, Nov 28th 2016

We’re big believers in Bootstrapping Using Services, as you know. Here’s yet another story of an entrepreneur who has scaled to over $10 million in revenue using the method.

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?

James Kane: I grew up in a very small town in far northern New York. It’s a college town of about 2,000 people. My father was a university professor. He taught Mechanical Engineering at Clarkson University. >>>

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Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper (Part 1)

Posted on Monday, Nov 28th 2016

Dan Stewart is a 1M1M entrepreneur. Read how he has navigated his way to an inflection point that has brought him to the cusp of 4x growth in 2017.

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?

Dan Stewart: My family moved around quite a lot as I was growing up. I rarely stayed in a school for more than a year. That took me from West Virginia and Chicago, down to Florida. >>>

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