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5 Things Raising Over $100 Million Taught Me About Bootstrapping
My Start as an Entrepreneur
I started my first company with a group of co-founders in 2001. It was one month after 9–11 and a year since the dot-com bubble had burst — and the economy was in the tank. Unlike today, young tech entrepreneurs were not in favor.
To go embark on an entrepreneurial journey, I decided to leave a high-paying management consulting job and invest my own money in a tech venture; having four young kids at home and a wonderful, supportive wife who worked as a teacher. My family and I live in Miami, which is not exactly a hub for tech companies or venture capitalists.
In short, I was terrified!
Up to that point, I had never pitched investors nor led a company. However, the venture was ambitious enough that it required a significant amount of capital. Through relentless pitch refinement and investor outreach, the team and I put together $2.5 million of angel investment in 2002. We later raised venture capital and grew the company successfully.
I then started my next venture, CareCloud, in 2009. We built one of the most complex multi-tenant SaaS products in existence at the time that delivers enterprise-class applications to serve healthcare providers in 50 different medical specialties across…
