How I Lost Twenty Bucks and Changed My Life

By Rajiv B. (TSB Co-Founder)

During the run up to the 2016 election, I saw a number of stories about Donald Trump that made me cringe. The clincher came on October 7, 2016 following the release of the Access Hollywood tape when Trump was recorded making very denigrating remarks about women. There's no way, I thought, this guy is going to become President. Over my life, I can count on one hand the number of times I've made a bet with money. So sure was I that there was no way the America I knew would elect Trump, that I bet a MAGA hat-sporting old-timer in my office twenty bucks that Trump would lose.

Well, I lost a lot more th