The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.
Episode 46 // August 22, 2016
Semil Shah has done remarkably well as a one-man shop with his investment firm, Haystack. But he is now wrestling with the challenges of growing his business while continuing to grow himself. How does he want to approach the next 5 years? And how does he develop the skills to get there? Adding to those challenges, there’s also a sneaky voice that speaks to him, one that can drive him and but also hold him back. A voice that is saying to him: “You don’t belong here, yet.” We all have a version of that voice, often referred to as impostor syndrome. The opportunity for all of us lies in how we choose to be with that voice.
Jerry and Semil explore that voice, and how shifting his relationship with it can help him be a better man and a better investor – the very things it and he are after.
Top Quotes:
“As the clock ticks, I get squeezed on the personal end and on the working end.” – Semil Shah
“Structurally, the biggest lesson I have learned is that the people who traditionally invest into funds want to write big checks.” – Semil Shah
“The only way to accept a big check and return a bigger check is by taking ownership in a company.” – Semil Shah
“We went from a household of three to five in a matter of a weekend.” – Semil Shah
“I have spent a lot of time getting to meet LP’s over the last couple of years, hoping that the success of the first two funds would translate into some larger commitments. I had to learn a hard lesson that there are either some things structurally in the environment (or in how I am presenting myself) that is not connecting with these people, and it is happening repeatedly.” – Semil Shah
“In the future, I will have to spend more time building relationships and being even more open about what I want to do and why.” – Semil Shah
“I feel like I have to constantly prove that I can identify and get into good companies.” – Semil Shah
“If you take sleeping six hours per night, dealing with kids in the mornings and evenings, trying to serve the people you’ve already committed to, and then trying to evaluate the people you want to bring into your circle, you have to start saying ‘no’ to a lot more people that I would have said ‘yes’ to in the past.” – Semil Shah
“There are a lot of people who are trying to invest, it’s pretty crazy to invest early, and there really is no barrier to do it.” – Semil Shah
“I don’t come from the world of technology. I don’t come from the world of finance. I don’t know this stuff. I am picking it up as I go along.” – Semil Shah
“I have so many thoughts moving around my head that I would go insane if I didn’t get them out.” – Semil Shah
“The experience you are having is very similar to the experience that the people who are looking for your investment are having.” – Jerry Colonna
