I have been in the cybersecurity industry for more than 20 years now. I have founded, operated, and exited several cybersecurity startups. I also advised, invested in, and even acquired a handful. Despite successful outcomes, my experience has left me perhaps a little jaded. Are we winning the battle? When I log into my various web accounts, I am so often reminded that my password had been stolen, sometimes alongside with my personal information. Even major financial institutions and government agencies have suffered a similar fate. Cybersecurity is broken, and here is why.