Karl Jacob pitched his startup LoanSnap to Richard Bransonduring a kiteboarding trip and walked away with the billionaire's backing for its $8 million Series A in 2018. Jacob was an early advisor to Facebook, and says his experience working in the early days of social networking reinforced his belief in taking bigger risks and bigger failures. According to Jacob, founders and investors need to be more comfortable with failure and more patient with teams trying to unseat massive entrenched industries. Visit BusinessInsider.com for more stories. Karl Jacob was riding high.