It's a weird little backwater we're in if the only perceived risk in starting a company is reputational. Most companies fail. The risk is financial. The people you see founding companies "again and again and again" generally fall into two categories:
(1) people who have never founded anything successful and have nothing obvious to lose, and
(2) people who have already succeeded (like Calacanis) for whom the risk is any the myriad of other things they could have been doing to make money during that time period.
(1) people who have never founded anything successful and have nothing obvious to lose, and
(2) people who have already succeeded (like Calacanis) for whom the risk is any the myriad of other things they could have been doing to make money during that time period.