When to Stop Bootstrapping and Raise Convertible Debt - Dan Street

In Chapter 9 of 20 of his 2011 Capture Your Flag interview, software entrepreneur and Loku founder and CEO Dan Street shares his excitement about raising a $600K convertible debt financing round for his business after funding the business by bootstrapping. Seeing a need to grow and compensate staff, he decides to raise outside capital after building a team up to eight people. Street reflects that bootstrapping was appropriate given his situation, and that it was a fundamental enabler in developing his vision for Loku. Street is the founder and CEO of Loku (previously named Borrowed Sugar) which develops Internet software to strengthen local communities. Previously, Street worked in private equity at Kohlberg, Kravis, and Roberts (KKR) and management consulting at Bain & Co. He earned a BA in music and business from Rice University.