Discussing Imposter Syndrome with Jerry Colonna and Semil Shah

From episode 46 of the Reboot Podcast: Hitting A Wall

In Episode 46 of the Reboot Podcast, Jerry is joined by guest investor Semil Shah. Semil Shah has done remarkably well as a one-man shop, but is wrestling with the challenges of growing his business and being with his growing family of 5 — while continuing to grow himself. Adding to those challenges, there’s also a sneaky voice for him, one that can drive him and also hold him back, one that is saying to him: “You don’t belong here, yet.” This voice, one most — if not all — entrepeneur-humans struggle with is the voice of imposter syndrome. Following is a select excerpt from the episode :

Jerry Colonna: I can’t recall the last time we talked about the imposter syndrome, but are you familiar with that?

Semil Shah: Yes, I know the first time you were mentioning that, is in the long podcast you did with Jason

Jerry Colonna: That’s right.

Semil Shah: — maybe two years ago.

Jerry Colonna: Yes.

Semil Shah: Sure. I had heard of it before, what’s sort of sad is, I didn’t know who you were and I wrote about your conversation with Jason, and someone said, “How can this person not know who Jerry Colonna is?” I looked up ‘imposter syndrome’ I never heard that before.

Jerry Colonna: So, here you go, this is a version of it. It’s epidemic in our society and sometimes, it does something really powerfully supportive for us. It keeps us humble. Sometimes, it gets so out of control and that’s when it actually flips into the imposter syndrome. It actually starts to diminish us, and it keeps us from realizing the fullest potential that we have. Now, you spending time with this aspect and becoming friendly with this aspect of your personality, now, I’m going to slip out of coach mode right now, and go into a little bit of a mentor mode. You slipping out of this or spending time with this can be super-helpful for you as an investor. You want to know why? You better say yes.

Semil Shah: Sure, yes.

Jerry Colonna: Because all of the entrepreneurs that you are looking to invest in suffer from this as well. Yesterday, I did a workshop for Techstars in Boulder, and I talked about some of the challenges of being a founder. I had a bulleted list, and one of the bulleted items was ‘The sensation of being utterly incompetent.’ Everybody laughed and everybody cried and everybody looked at it and realized they all had that same feeling. The concomitant fear is that people are going to figure it out. So, you keep telling me over and over again, just to make sure that I make no mistake about it, that you don’t have a background in technology, that you are not really it, do you hear it?

Semil Shah: Yes.

Jerry Colonna: What you are trying to do ward off again is me looking at you and saying, how can you not know who Jerry Colonna is? How can you not know who this — how could you not know this fact or this thing?

Semil Shah: Part of it is also just what I have observed in the venture capital world is that because there is a lot of competition and most people are differentiated and they are selling a commodity, that it’s easier to deposition other people.

Jerry Colonna: Yes.

Semil Shah: I heard a lot of feedback that I had no idea existed about me, from people when I was reference checked. That was just a huge, eye-opening thing of like, oh my God, now there’s these people who have collected pretty granular feedback on me that I would have no access to it — it’s in a vault somewhere.

Jerry Colonna: Right, which again contributes to the paranoia.

Semil Shah: Yes, it’s a little bit of paranoia; I feel like I act and behave online as I do offline, and so I’m consistent and so I don’t worry day to day about that. I think if someone doesn’t like it or doesn’t like me, that’s fine, I try to be pretty fair. It’s funny, I’m looking this up on Wikipedia now, and there is a section called ‘Writing therapy in imposter syndrome, allows a person to organize their thoughts in writing.’

Jerry Colonna: And you are laughing because you are think you do that; don’t you?

Semil Shah: Oh yes; actually I sat down — like I had lunch with Fred, I remember, a year ago, and we had a lunch and he asked me, “Why do you write?” He was like, I can tell you why I write. He’s like, it just helps me clarify things and this is a thing I do in the morning and Yoga and blah-blah-blah and he said, why do you write? I said, “Man, I have so many thoughts moving around in my head, that if I don’t get them out, I’ll go insane.” So it kind of keeps me — it gives me a framework and a structure within which to organize all the new information that I’m processing.

Jerry Colonna: I think that is super-helpful and super-important. I want to take you back though, to this notion of the way people — what did you call it, deposition?

Semil Shah: Deposition.

Jerry Colonna: Yes, so if you take a moment, can you hear the middle school-like atmosphere you are talking about?

Semil Shah: Oh yes.

Jerry Colonna: That’s like a kind of a consequence of the competitive aspect and how it antagonizes some core insecurities? So, here’s another insight: every one of your entrepreneurs feel the same thing. They are all worried about how they are being positioned vis-a-vis either the competition or sometimes not even the competition directly in the market, but the competition in terms of mind share. So, when they come to our bootcamp, and they come on the shows, part of what they are dealing with — this is the main point I want you to hold on to.

The experience that you are having is very similar to the experience that people are looking for your investment are having. If you really want to be an effective investor, stay connected to those feelings because that will turn you into an incredibly supportive investor.

Semil Shah: I feel that when I’m with entrepreneurs or when I’m dealing with an issue and I talk to them in a certain way, or talk with them in a certain way, and I get that feedback from them and they are like, ‘oh’ because it’s not the same thing that we are doing but it is the same feelings.

Jerry Colonna: Yes, exactly.

Semil Shah: So that does make a little bit of a difference in at least those kind of intense conversations.

Jerry Colonna: Exactly, that’s exactly right. As a director, once you have made an investment, as you slip into that role of being the chief conciliary, you get to draw on the emotional experience that you have had, or feeling somewhat excluded, of feeling somewhat less than, a feeling perhaps you are out of your depth, trying to make sure people understand that, worrying about — from a paranoid stance, worrying about what people are thinking about you.

As you feel all those things? My encouragement to you would be to stay connected to those feelings as you work with the entrepreneurs, because what the entrepreneurs need more than anything else is that kind of support. Then when you give them advice appropriate from a board member, you are giving them an advice within the context of a larger understanding of their journey.

Listen to the full episode: