Today's guest is Sukhinder Singh Cassidy. For more than 25 years, she’s been a leading tech entrepreneur and CEO who’s grown, scaled, and advised for companies like StubHub, Google, Amazon, and more. She’s currently the Founder and Chairman of theBoardlist, a talent marketplace focused on putting diverse leaders into key executive positions -- and also serves on the board of directors at Urban Outfitters and Upstart.

She just wrote a new book called, Choose Possibility: Take Risks and Thrive (Even When You Fail), where she shares the most valuable lessons she’s learned over her years of experience in leadership roles at some of Silicon Valley’s most well-known companies.

In this episode Lewis and Sukhinder discuss the life-changing lessons Sukhinder learned from her father, why most businesses fail and how to make sure your business isn’t one of them, why we all need to change our mindset around failure & risk taking, and what to do instead, the best ways to start building wealth today, what Sukhinder considers the most rewarding experiences she’s had over the course of her career, and so much more!