Killing It! – Leaving the Hero Complex of Foundership Behind, with Shamir Karkal, CEO of Sila

What happens when entrepreneurs have to face down the most difficult decision there is — knowing when it’s time to sell, shut down, or exit?  In this special crossover series, Alex joins Breaking Banks’ Jason Henrichs for candid conversations with fintech leaders who have experienced the loss of their company. This week, Alex and Jason talk with Shamir Karkal, CEO of Sila and former Co-Founder of Simple, which was acquired by BBVA in 2014.   From the early days and pain points of launching Simple to the eventual dismantlement of it by PNC in 2020, Shamir describes his journey of “wandering through the wilderness” and finding his sense of identity and place in the world again. Is the founder mentality only for the young? Shamir reflects on how his hero complex and founder mentality have evolved into a more holistic approach as he enters his 40s.    Sign up for Alex’s Fintech Takes newsletter for the latest insightful analysis on fintech trends, along with a heaping pile of pop culture references and copious footnotes. Every Monday and Thursday: https://workweek.com/brand/fintech-takes/   And for more exclusive insider content, don’t forget to check out my YouTube page.   Check Out Breaking Banks: Apple: https://podcasts.apple.com/us/podcast/breaking-banks/id641357669  Spotify: https://open.spotify.com/show/4mhqSxyBCHZ1wTQwXlAvCG?si=2964cce20998440e  Follow Jason:  LinkedIn: https://www.linkedin.com/in/jasonhenrichs/   Follow Shamir: LinkedIn: https://www.linkedin.com/in/shamirkarkal/   Follow Brent:  LinkedIn: https://www.linkedin.com/in/brentfree/   Follow Alex:  YouTube: https://www.youtube.com/channel/UCJgfH47QEwbQmkQlz1V9rQA/videos LinkedIn: https://www.linkedin.com/in/alexhjohnson Twitter: https://www.twitter.com/AlexH_Johnson