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Entrepreneur Journeys

Bootstrap First, Raise Money Later: Ben Hodson, CEO of JobNimbus (Part 1)

Posted on Thursday, Jul 22nd 2021
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Ben is a serial entrepreneur with a long experience in bootstrapping and fundraising. Read on to see how he has navigated his journey.

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 did you have?

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Featured Videos

Navigating Multiple Product Pivots: Jebbit CEO Tom Coburn (Part 1)

Posted on Wednesday, Jul 21st 2021
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Tom discusses a very important aspect of building a product company: pivots.

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?

Tom Coburn: I was born in a suburb outside of Boston, Massachusetts. It’s where the Boston Marathon starts. I grew up there and lived there all my life. I went to high school there at a local public high school. I ended up going to Boston College. I went there to study Biology and become a doctor. I ended up dropping out. I’d also picked up Theology as a double major. I was studying science and religion and ended up doing a marketing technology and data company instead.

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Building HubSpot to a Unicorn: Dharmesh Shah’s Amazing Entrepreneurial Journey (Part 1)

Posted on Friday, Jul 16th 2021
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Dharmesh discussed his entrepreneurial journey with candor, humility, and generosity. Wonderful conversation.

Sramana Mitra: We will start at the very beginning of your journey. Where did you grow up? What kind of upbringing and what kind of circumstances were you raised in? I know you come from a part of India that is particularly entrepreneurial.

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Bootstrapping for 30 Years: Dean Guida, CEO of Infragistics (Part 1)

Posted on Friday, Jul 9th 2021
5 Things I Wish Someone Told Me Before I Became CEO of Infragistics,” With Dean  Guida | by Carly Martinetti | Authority Magazine | Medium

Dean has a real passion for the elegance, simplicity, and beauty of software development. He has built a company celebrating these values.

Sramana Mitra: We will start at the beginning of your journey. Where are you from? Where were you born and raised?

Dean Guida: When I was six years old, my mom and dad got divorced. I moved to Miami, Florida. I saw how much my mom struggled to make money for us, When I was eight years old, I just wanted to work. I convinced the maintenance man in the apartment that I was living in to let me do his work. He would pay me off the books.

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How to Create a Monopoly in an Esoteric Niche: SteelCloud CEO Brian Hajost (Part 1)

Posted on Tuesday, Jun 8th 2021
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If you haven’t already, please study our free Bootstrapping course and the Investor Introductions page.

Everyone talks about BIG markets. Learn how to build a monopoly in a small market and, as a consequence, a strong defensible business.

Sramana Mitra: Let’s start at the beginning of your journey. Where were you born and raised? What kind of background did you have?

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Surviving Covid with a Bootstrapped Venture: Kristi Herold, CEO of JAM (Part 1)

Posted on Tuesday, May 4th 2021
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If you haven’t already, please study our free Bootstrapping course and the Investor Introductions page.

Kristi built a thriving bootstrapped business over twenty years until Covid hit. Read how she is surviving Covid.

Sramana Mitra: Let’s start at the beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

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From Solo Entrepreneur to Serial Exits: Shane Neman, CEO of EZ Texting (Part 1)

Posted on Wednesday, Apr 28th 2021
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If you haven’t already, please study our free Bootstrapping course and the Investor Introductions page.

Shane started as a solo entrepreneur and built two companies, bootstrapped both, and found successful exits for each.

Read on for more on his journey.

Sramana Mitra: Let’s start at the beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

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Bootstrapping Using Services from Atlanta: Avelead CEO Jawad Shaikh (Part 1)

Posted on Monday, Apr 5th 2021
Jawad Shaikh - Business Journals Leadership Trust

If you haven’t already, please study our free Bootstrapping course and the Investor Introductions page.

As usual, we love Bootstrapping Using Services case studies.

Sramana Mitra: Let’s start at the beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

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Best of Bootstrapping: Duda Co-founders Bootstrap with Paychecks

Posted on Monday, Mar 29th 2021

If you haven’t already, please study our free Bootstrapping course and the Investor Introductions page.

Itai Sadan is the Co-founder and CEO of Duda, a company that turns desktop websites into mobile sites. When we spoke in 2013, Itai had over 10 years of experience in business development, partner management, program management, and development. Prior to founding Duda (formerly DudaMobile), Itai was a director at SAP, where he managed the SAP Discovery System program and was in charge of relationships with IBM, HP, and Fujitsu.

Sramana: Itai, let’s start with the beginning of your personal journey. What is the story that paved the way for your entrepreneurial journey?

Itai Sadan: I was born and raised in Tel Aviv, Israel. I did have a six-year stint in South Africa, where our family lived for a while. I went to high school in Tel Aviv and met the person who is the co-founder and CTO of DudaMobile during my high school years. After high school I went to the army and served in the anti-terrorist school. After I completed my three-year army service, I traveled the world a little bit.

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Bootstrapping to $7 Million: Constellix CEO Steven Job (Part 1)

Posted on Thursday, Mar 11th 2021
Steven Job

If you haven’t already, please study our free Bootstrapping course and the Investor Introductions page.

Steven has built a lean company with 37 people and has scaled it to $7 million. Read on to learn how.

Sramana Mitra: Let’s start at the beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

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