From the outside, Upwind Security looks like it’s had a smooth journey so far. Just four years in, the cloud security startup is now worth $1.5 billion, and boasts the likes of Siemens, Peloton, Roku, Wix, Nextdoor and Nubank among its clientele. But if you ask the company’s co-founder and CEO Amiram Shachar, the journey to get here was anything but certain. “Three years ago, we would spend hours asking ourselves if we were heading in the right direction, and 80% of the time, it felt like we