Jake Gibson, former investment banker, entrepreneur / co-founder NerdWallet, angel investor, now VC founder Better Tomorrow Ventures, who crossed career paths with host Jason Henrichs 10+ years ago, have an honest discussion about the twists and turns of co-founding a boot-strapping start-up particularly when you are young, on to something and quickly have to figure everything out. After years of hard work and being all-in, tough decisions needed to be made as NerdWallet continued to grow quickly. Jake knew it was time to move on, but so hard to do. The arrival of twins and focus on strengths, honesty, lessons learned, and giving advice to others in similar situations, helped Jake figure his calling and path forward, and has enabled him to keep many ‘cards in his wallet’.