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.

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.

Serial Entrepreneur Bootstrapping Three PropTech Ventures: LuxuryProperty Founder Jason Hayes (Part 2)

Sramana Mitra: When you sold the company in 2007, what were the metrics?

Jason Hayes: The value of the entire portfolio was in the region of $200 million. Revenues were approximately 10% of that. There was probably about 70% loan to value. I sold it to a London hedge fund. I remained with the company for a couple of years in an advisory capacity. At the same time, I was busy building my second venture ,which was Propertyandhomes.com in California.

Serial Entrepreneur Bootstrapping Three PropTech Ventures: LuxuryProperty Founder Jason Hayes (Part 1)

Jason has worked at the cusp of real estate and digital marketing for 35 years and built three successful ventures. All of them are bootstrapped, organically grown, capital efficient businesses.

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?

Building a Generative AI Startup to $10M+ with a Virtual Team: Chris Lu, CEO of Copy.ai (Part 4)

Sramana Mitra: In terms of function, it was still operating as a UI to OpenAI.

Chris Lu: Right. The early models were not as easy to use compared to the models today. There was still a good amount of work required to get good results.

Sramana Mitra: With the timing of the development of OpenAI and ChatGPT, you were coming in to a window where all of that wasn’t developed and you were offering usability.

Building a Generative AI Startup to $10M+ with a Virtual Team: Chris Lu, CEO of Copy.ai (Part 3)

Sramana Mitra: What kind of conversion rates were you seeing from free to premium?

Chris Lu: We got a lot of people who are international and who aren’t able to pay $49 a month. If you filter it down to the core markets – US, Canada, Australia, UK – it looks like a normal SaaS conversion metric.

Building a Generative AI Startup to $10M+ with a Virtual Team: Chris Lu, CEO of Copy.ai (Part 2)

Sramana Mitra: What do you offer?

Chris Lu: When we first started, we were more of a copywriting app. We help write your email copy or sales copy. However, that has transformed over the years. Our entire vision has always been the business’ business. How do we become the product that helps your business assemble and run itself?

Building a Generative AI Startup to $10M+ with a Virtual Team: Chris Lu, CEO of Copy.ai (Part 1)

Chris and Paul have built a front-end to Open AI and a significant business with over $10M in revenue. Now, they’re broadening their product capability to business workflows. We also discuss ideas and opportunities for new entrepreneurs.

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?