Sahil and his team at Gumroad have helped over 40,000 creators do more of what they love and have sent over $200,000,000 to creators and artists. This is an incredible achievement. So, when I read his February 2019 Medium Blog post entitled, “Reflecting on My Failure to Build a Billion-Dollar Company (It took years for me to realize my pursuit of growth was misguided from the start)” I knew it was time to get him on the show and share more.
I really appreciate Sahil detailing this journey. He had a personal epiphany around his own motivations as a Founder & CEO. And he walks through this and much more in this very candid interview.
Ok, Bob shares a TON of personal insights in this extended interview. The reason? You won’t find a lot of Founders who have scaled up their companies to nearly 15,000 customers and then IPO. He talks in detail about the following topics:
His 3 CEO stages that a Founder must transition to over the course of growth
How his team gave him challenging feedback and how that prompted him to change through these different stages
Unlearning things he had learned early on as a Founder, because they did not work leading a 500 person company
How he approached his board about leaving his CEO role
You’ve seen him on Shark Tank earning an investment from Mark Cuban. Shaan is an achieving machine. In addition to growing Prep Expert, Dr. Shaan Patel is also in residency for dermatology. And, he is a fountain of knowledge. In this interview, he explains the personal challenge he encountered with having his cousin working in the business. He shares some key advice about working with family and the value of professionalism in this candid interview.
Ethan is at the beginning of his Founder to CEO transition, but that doesn’t mean he lacks in wisdom. He is very insightful about the mindset you need to have when hiring and shares the mistake he made that he hopes you don’t make.