Approaching a new industry as an outsider and as a team of one would be daunting for most founders. But Chen Amit, Founder and CEO of Tipalti, was a repeat entrepreneur building in a new arena. In the past 13 years, he has scaled Tipalti— a finance automation suite focusing on global payments and accounts payable—into one of the most highly valued privately-held fintech companies in the globe. With a valuation of $8.3B, Tipalti processes over $43B in payments annually. Chen shares why signing his third customer was his biggest signal of product-market fit, what playing poker taught him about taking calculated risks, and why he relearns his job every eighteen months.