Best of Bootstrapping: Bootstrapped a Virtualization Services Company

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

Abacus Group Founder CEO Chris Grandi has significant domain knowledge in the hedge fund industry. When we spoke in 2015, he had self-financed a successful company offering to secure virtualization services to the segment with high service levels.

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

Chris Grandi: I was born and raised on the East Coast outside of Washington DC, and I grew up in suburban Maryland. For university, I went to the West Coast and attended UCLA. I then continued on to graduate work. I got my MBA from Harvard Business School. I moved out to San Francisco, California where I’ve been for approximately 20 years.

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Serial Entrepreneur Bootstrapping Three PropTech Ventures: LuxuryProperty Founder Jason Hayes (Part 6)

Sramana Mitra: What you’ve built is a vertical search engine that is specific to luxury real estate. That has its own meta tags and meta data. What is the AI part of it?

Jason Hayes: We do have some AI agents launching soon. We believe that we are going to be the first to do that. Certainly in the Middle East anyway. The AI we’re using is in the backend of the system. For our brokers who work for us, we have what we call the opportunity platform. That is an app that forms part of the CRM.

Serial Entrepreneur Bootstrapping Three PropTech Ventures: LuxuryProperty Founder Jason Hayes (Part 5)

Sramana Mitra: Let’s go to the Dubai business. Why Dubai?

Jason Hayes: Tax. We don’t pay tax over here. We enjoy the most incredible taxation over here. There is no income tax or capital gains tax. That was a big driver for me. I was hugely keen to go into the PropTech area. Dubai has the most enormous real estate market. It looked to be the most incredible place to do the property portal.

Best of Bootstrapping: Lessons Learned from Different Combinations of Bootstrapping

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

FairWarning Founder Kurt Long has tried different permutations and combinations of bootstrapping, several of them successfully. Listen to his perspective on each of those from when we spoke in 2015. FairWarning was acquired by Imprivata in 2018.

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

Kurt Long: I was raised in Clearwater, Florida. I grew up in Florida at a very special time where we enjoyed being outside and in the waters. As I grew up, I watched the Apollo missions and other NASA-based missions take off from the Kennedy Space Center, which is on the other coast but you could still see the launches. From a very early age, those made an impression on me that I wanted to participate in innovation and exploration. That’s something that has stayed with me through my whole career. As I went through high school and college, I held on to the dream and even wrote letters to Kennedy Space Center to ask about the Space Center and how it worked.

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Serial Entrepreneur Bootstrapping Three PropTech Ventures: LuxuryProperty Founder Jason Hayes (Part 4)

Sramana Mitra: One of the keys to building scalable businesses is to operate within guardrails. What you’re pointing out in deciding not to go for any kind of permit is a huge decision. It’s a smart decision. That allows you to move quickly. In the business that you did first versus this business, it’s a different model. Debt financing is the same, but you’re not building as much in the balance sheet.

Jason Hayes: That’s right.

Best of Bootstrapping: Bootstrapped with No Outside Financing to $300M

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

Faisal Husain, CEO of Synechron, is one of those rare entrepreneurs who managed to grow his business with no outside financing to significant scale when we spoke in 2015. We discuss his journey here.

Sramana Mitra: Let’s go to the very beginning of your story. Where are you from? Where were you born, raised, and in what kind of background?

Faisal Husain: My roots are from India, but I was actually born in West Africa in Nigeria. My parents had moved from India to Nigeria in search of jobs and they were in the education field. My father was a principal and my mother was a math teacher. While they were doing their jobs and building their careers in Nigeria, I was born there. I lived in Nigeria for 13 years. At that point, my parents decided to move back home to India. I was then home schooled for about three or four years, and then came to the United States.

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Serial Entrepreneur Bootstrapping Three PropTech Ventures: LuxuryProperty Founder Jason Hayes (Part 3)

Sramana Mitra: What segment were you going after? What kind of price?

Jason Hayes: I started by buying homes around the $300,000 mark. I was looking to go for volume and was trying to spread the risk. Sometimes, we would buy homes that were significantly cheaper and sometimes, we would buy homes that were significantly greater in value. For me, it was all about what the value proposition was.

Best of Bootstrapping: Bootstrapped from London, Scaled in the US

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

Alexandre Wentzo is the former CEO of Casewise, an enterprise software company that started in London and scaled in the US. The company was self-financed and did $24 Million in revenue when we spoke in 2015. Our discussion focuses on some of the nuances of starting an enterprise software company in Europe and scaling it in the US. Casewise was sold to Erwin in 2016. You can also listen to our podcast interview here and watch the roundtable interview here:

Sramana Mitra: Let’s start at the very beginning of your story. Tell us where you’re from, where you were born, raised, and in what kind of background.

Alexandre Wentzo: I was born outside of Paris in a little suburb. I come from a low social background. I would say that when I was around 13 years old, I started to set up my business. I used to check out every shop around my place. I started to offer brochures and create any marketing collaterals they needed and offered the complete package, from the design to the printing.

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