For as much discussion there is around venture capital funding and massive fundraising rounds, the simple fact is that many small businesses are bootstrapped. Founders decided to take a risk and invest their own capital into making their business dreams come true. However, the road from a bootstrapped business to one that is making millions in annual recurring revenue isn’t an easy one. Often, there are daunting obstacles and roadblocks that can make it seem almost impossible.
To learn more about making that transition from bootstrapping to millions in annual recurring revenue, we spoke with Amir Reiter. Amir is the founder and CEO of CloudTask. CloudTask is a company that provides teams of outsourced sales, outsourced customer success, and outsourced customer support experts. While initially bootstrapped, Reiter grew CloudTask to a five million dollar per year business.

In his discussion with Dubb founder Ruben Dua, Amir touched on topics like his origin story, how he was able to scale and generate recurring revenue while bootstrapping, the biggest problem in sales outsourcing, and the truth about inbound versus outbound sales. We’re certain that you’ll enjoy this fascinating conversation.