October 20, 2016

Gimlet 23: Shadowed Qualities

by StartUp

Background show artwork for StartUp

The Story This week, Alex receives feedback about his job performance from his co-workers, friends, and family. Some of it is good, some less so. But there is something else that comes up during the review process that shocks him. We explore what happens when you unpack your emotional baggage—or someone unpacks it for you—and you realize the unexpected effect that it has been having on your team. In this final Gimlet-focused episode of season four, we take a raw and intimate look at a defining moment in the trajectory of a CEO. 


The Facts David Herman mixed the episode. Our theme song was written and performed by 

Mark Phillips. The special ad music, Microliters, was written and performed by Build Buildings. Our logo was designed by Elias Stein. Additional music from Bobby Lord, Takstar, and Hotmoms.gov.   

Where to Listen


ALEX: Hello and welcome to Startup, the podcast about what it’s really like to start a business. For the first couple of episodes this season, we’ve been talking about Gimlet, the company that produces this podcast you’re listening to, and many more. And we’ve been talking about growth. How it’s awesome, but also scary, and hard to manage. And I’m going to say right up front, today’s episode might be one of the most personal stories I’ve ever done. And I’m actually a little scared about putting it out there. But, the truth is, I went through something, and I learned a lot from it. I learned a lot about myself, and I learned a lot about what makes a business function well. And so, I’m sharing it with you. The whole thing started, here:


JERRY: Tell me… How are you guys doing, and what would you like to talk through today?


ALEX: This is a man named Jerry Colonna. Jerry is what they call an executive coach. And this is the beginning of a session he’s doing with me and Matt. Matt and I started seeing Jerry at the advice of one of our investors, a guy named Troy Carter who founded a firm called CCV, Cross Culture Ventures. And Troy encourages every founder CCV invests in to get an executive coach from the very beginning. Troy told us that a lot of founders are in the same position as Matt and I, running organizations for the first time. And having an executive coach on board from the beginning can help navigate the questions, and decisions and conflicts that inevitably arise. It was some of the best advice we’ve ever gotten. Jerry might be familiar by the way—he made an appearance in Startup season two, when he helped the founders we were following work through some issues they were having. And he has an impressive pedigree. He founded the venture firm Flatiron partners in the mid 90’s, with legendary investor, Fred Wilson. After that he helped run the private equity arm of JP Morgan Chase. He’s seen hundreds of companies at all different levels of development. So he can help talk through nuts and bolts issues like how to manage a sales team. And how to structure a funding round. But what he’s really good at, and why firms like Etsy and Soundcloud seek him out as a coach, and why he’s been given the moniker, the CEO whisperer, is that he’s really good at talking about feelings. A lot of what Matt and I talk about with Jerry are the kinds of touchy feely things you might discuss in therapy. And that’s because, according to Jerry, the health of Gimlet depends on me and Matt fully understanding ourselves. Especially our blind spots: our weaknesses, vulnerabilities, the parts of ourselves we’re afraid to look at, that we dislike, that we try to ignore.


JERRY: If you’re not conscious or aware through what I often refer to as a radical self-inquiry? The culture that gets created around you is going to reflect pretty much your worst character traits. Your shadowed qualities as a leader. The parts of youself that you want to push off to the side.


ALEX: Jerry sees it all the time. A founder with anger issues, who’s always blowing up at people, or reacting in ways he can’t control, will unintentionally create an angry or abusive culture. A founder who’s conflict averse, on the other hand, will create a quiet, but bitter and back-stabbing environment.


JERRY: I will tell you that the organizations that I have worked with that have been the most difficult culturally, have been the organizations that have been most, um, determined to repress the negative aspects of their own behavior. Their own individual leadership behavior and drive those behaviors underground only to have it pop up in politics and in nastiness. And we don’t even see it coming. So those are the things that terrify me. If you’re not consciously, intentionally creating your culture, a culture is going to get created around you, or despite you.


ALEX: In other words, one of the most beneficial things we as founders can do for the long-term health of Gimlet, is to deal with our own emotional baggage. Haul it out in the light, rummage through it. Take a hard look at what’s inside. And I did that. And I was shocked by what I found. And that’s what I’m talking about, on today’s episode. Quick warning, there’s a little bit of cursing that comes along with that.


ALEX: Alright, so this is my, um… This is the 360 report on me.



ALEX: In the summer of 2016, Jerry’s company, Reboot, conducted something called a 360 review on me and Matt. The idea of a 360 review is to give as full a picture as possible into how someone is performing on the job, and what they need to do to get better.The way it works: Someone from Jerry’s team asked me and Matt a set of questions designed to get us talking about our strengths and weaknesses. Then they ask a bunch of people around us the same set of questions. Jerry and his team compile the results, and present them to us in a long, detailed report. Which I shared with my wife Nazanin right after I received it. The report started by listing all the people they’d talked to about me:


ALEX: The respondents included 2 investment board members, 7 members of the Gimlet Media Team, and 3 personal friends/family members.

NAZANIN: Who are your personal friends?

ALEX: I don't remember.

NAZANIN: Who do I count as?

ALEX: I don't know that either.


ALEX: Based on your current observations—and these were the questions that were asked—based on your current observations and dealings with Alex, how would you say he contributes to the success of Gimlet Media? What does Alex do that prevents Gimlet Media from running as successful as it could?


ALEX: The report’s authors summarize and draw out themes from the interviews, and they also include key quotes that have been anonymized. And of course, they start with the good stuff.


ALEX: Alex has been considerate about what I am passionate about, he is genuinely interested in those he works with.

NAZANIN: This one is really… I think this one is—

ALEX: People feel like they can go to him and talk to him about whatever problem they are having. He's really good at not reacting to things defensively and I think Alex has gotten really good at hearing people and listening to them and letting them get out what they need to get out and then talking to them without reacting.

NAZANIN: Yeah. I agree with that.

ALEX: A lot of people came to work at Gimlet for and with Alex. He is good at mobilizing people, he is good at addressing people's concerns and still staying on track. Alex inspires people to do their best, infectious enthusiasm is his greatest strength. He’s really supportive. Blah blah blah.

NAZANIN: That’s all of it—that’s all… That’s great.

ALEX: That’s all good.

NAZANIN: It’s all good.

ALEX: Okay. Areas for improvement slash growth.


ALEX: Otherwise known as weaknesses. There were plenty of them. The report pointed out my tendency towards quote blind optimism, which can get in my way when it comes making a hard assessment about something happening in the company. Also, I don’t manage my time well, and I overcommit to things.


ALEX: Key quotes on overcommitment. He tends to underestimate the time and resources necessary to build something. Yep. Constantly running late? Yeah, yeah, yeah, I know. Sometimes I'm at a meeting or gathering with him and I can tell he's not really there. Did you say that?

NAZANIN: I may have but I don't remember. I don't think I would say, "or gathering with him," “sometimes I’m gathering with him.” But I agree with that person. I'm with that person.

ALEX: Uh huh...

NAZANIN: Sometimes I'm in a meeting, sometimes I'm in my life,

ALEX: Right

NAZANIN: Like right now, when you're not listening to what I'm saying.

ALEX: Right, I'm not listening to what you were saying, what were you saying? Sorry I was reading more quotes about myself.

NAZANIN: Nothing.

ALEX: Seriously, what'd you say.

NAZANIN: It was just…

ALEX: I'll just listen back to the tape.



ALEX: Another area of weakness my reviewers pointed out: My engagement on the business side of Gimlet. From the report: Quote. It is clear that Matt is well versed in business management and there is great chemistry between the two of you. Still your reviewers suggest there is an opportunity for you to engage with larger issues. This may require a shift from being in the problem-solving role you have taken on with editorial projects. So the way things stand at Gimlet right now, there is a pretty clear division of labor between me and Matt. Matt’s overseeing sales, budgets, operations. I’m overseeing the new shows we’re developing. And overseeing that is super time consuming. Just, as an example, take one of the new shows we just launched, Heavyweight, hosted by Jonathan Goldstein. Each episode of that new show involved multiple, multi-hour edits. Where Jonathan would come in with a script, his tape all lined up. He’d do a live read of his story, playing the tape off his computer. And then we—he and I, and another editor and his producers—would puzzle through the sections that weren’t working. Move stuff around. Change the writing. Most edits take at least two hours. Often more. And the edit is just one part of the process. There are lots of other parts, which take equally as much time. There are story meetings. There are mix reviews. Just sitting and talking through a story with someone. All to make one episode, in a multi-episode season of one new show. We’re launching six new shows. If you looked at my calendar, here’s a random and typical Friday. It’s booked solid with me working on stories. There’s a two-hour edit in the morning. A two-hour mix session in the afternoon, where we review music and sound design on one of the shows we’re launching. And then another three-hour edit after that. And that’s pretty typical. I have other stuff. Budget reviews. Board meetings. But the vast majority of my time is taken up by this creative/editorial puzzle solving. And for now, this probably makes sense. Because at the company, I’m probably the most experienced person at doing this. It is, after all, what I spent the last 15 years of my life doing. And right now, the best thing we can do as a company is launch really good shows. So, if I’m helping that, I’m helping Gimlet. But the review pointed out that there is the tension between what I should be doing for Gimlet now, and what my role should be in the future, if we want Gimlet to continue to grow and thrive. It pointed this out in a section called “upcoming challenges.”


ALEX: Upcoming challenges, areas critical to future success. Two themes emerged when reviewers were asked to identify your greatest challenges going forward, scaling and foresight.

NAZANIN: That's what I said.

ALEX: Scaling?

NAZANIN: Mm-hmm.

ALEX: Your reviewers believe your current management style does not naturally translate to a larger team. They see tension between being intimately involved with the editorial process and managing a growing team. Moving forward, they see this as a challenge you're likely to face. Several of your reviewers sympathize with you as they do not see a simple solution to this issue.


ALEX: In other words, my calendar can’t continue to look the way it does now. Because, when I’m spending my day running from one edit to another, diving deep into the weeds of individual stories and shows, I can’t pull back my focus and look at the company as a whole. Which, as CEO, is my job. My job is not to make the shows. My job is to make the company that makes the shows. And as we learned last episode, at least some of the producers I’ve entrusted to make those shows don’t feel adequately supported by that company. And if that’s happening now, just imagine what it’s gonna be like when we’re bigger. In other words, I need to be thinking more about the big picture, What should GImlet’s priorities be in 2017. What about other revenue streams besides advertising. We probably do need to build an app. Who does it? How do we pay for it? I need to be working on what the review calls, quote, increasing my foresight:


ALEX: Increasing your foresight would recognize the need to meet with a team member whom you have not seen in some time or perhaps initiating a strategic decision with your team. Foresight is also a potential counterbalance to the blind optimism. Right. These questions may support your self-inquiry. Have I paused to take all available information into consideration? With this decision am I thinking through the long term impact of each option? Am I regularly setting time aside to  think strategically about issues at hand? No. What morning and evening routines will support me in being more prepared for the meetings I have scheduled each day?


NAZANIN: Yeah. I don’t know. What do you think? What do you think? Like, what…

ALEX: I don't know. Something about this just makes me ... Really emotional. And I don't know why.

NAZANIN: Do you think it’s like your flaws are more transparent than you thought they were?

ALEX: No I think… No, I don't think it's that. I think it's, um... It's just, um … What morning and evening routines will support me in being more prepared for the meetings I have scheduled each day, is like… I’m not disciplined, in that way. Like, it's clear that I have to get good at certain things that I'm not good at. And it makes me worried that I will have to become a kind of person that I’m not, and I’m not sure I wanna be? I guess, basically, all these things are like… The thing that's not reflected is that I love what I'm doing right now and I love being involved in all these things, it's really fun. And it feels like that is, it's really fun to be really good at something. And that's what I feel like I am right now. And I feel like a little bit what's being told is you have to stop doing the thing that you love and you're good at and get good at something else. You know?


ALEX: I don’t know why I’m crying about this. I don’t know. I don’t know.

NAZANIN: Yeah, why are you crying?

ALEX: I don’t know!

NAZANIN: Well, can I just… What did you think the 360 review process was going to be like?

ALEX: No, I mean, I knew it was going to be intense. I thought it was going to be more intense, I thought there was going to be more stuff. There's really nothing here. It's just like… It’s just like… So I was like sitting with Zach and Mark and Matthew in the studio for like four hours today trying to puzzle through just finessing and sort of, like, thinking through how this first episode of their first show is going to sound. And like… That's good for the company, this show has the potential to be one of the biggest hits that we launch. I don't think it's a bad use of my time and I am the best person to be doing that at the company. So I think strategically it all makes sense right now. But like, the other thing that is not reflected here is that I love doing it. It’s the thing that I've worked my whole life to get really good at it. That's the thing I feel I'm going to have to give up, you know? I need to move away from something that I've got really, really good at to something I'm not nearly as good at which is, uh, coming up with morning and evening routines to support me being more prepared for meetings I have scheduled each day.

NAZANIN: I mean, I think that’s bullshit though.

ALEX: It’s not bullshit. That is not bullshit. I have thought that. I have had that exact thought many times. I need to be better at this, it's not bullshit. It's what I need to do, I do need to do that.


ALEX: And that is where I left it with Nazanin that night. A couple minutes later we turned off the recorder and went to bed. But later, I would find that there was something larger behind my reaction to that sentence. Something larger that involved my shadowed qualities as a leader. That’s coming up, after the break.






ALEX: Welcome back. So, after I got my results back from my 360 review, I got in a video conference with Jerry, to talk it all through.


JERRY: Hey, how are you?

ALEX: I’m good, I’m good. How are you?

JERRY: I’m good. Good! It’s been a while.

ALEX: I told him the whole story of my strange reaction to that one line.

ALEX: But then I started crying talking to Nazanin about it. And I think it was… Let me just pull it up here. “What morning and evening routines will support me for being more prepared for the meetings I have scheduled each day?"

JERRY: And you read that line last night and were crying?

ALEX: And I read that line last night and I started crying and Nazanin was like What the fuck are you... There's nothing to cry about here! It was like she honestly she was like, "I think you're feeling a feel that I don't get it because from my perspective you obviously need to keep doing that in the company, that's the thing that you're really good at. And I don’t know. But I think it was just… Partly it was just like… um, I don't know what it was about.


ALEX: So, perhaps obviously for a man who’s so interested in unpacking emotional baggage, Jerry found it very interesting that this one innocuous sentence had caused such an emotional reaction. And so he started probing. Asking about it. And I’ve been in therapy before. Off and on. I’ve always found it helpful. But I’ve never really had what is typically called a breakthrough. But talking to Jerry, in that studio on that video conference, I did. And I’m now going to play you, what happened. It was weird. And intense. And it started with Jerry and I talking through the feelings that that sentence called up in my while I was reading it.


ALEX: There’s I think there's also an element of feeling trapped in that statement to me that I have to... I have to give up a—clearly I say 'give-up' all the time—there's something about that statement that means I'm going to give something up? I guess, giving up a freedom.

JERRY: Right. Alex, it's not all fun and games.

ALEX: Right, I gotta grow up.

JERRY: You gotta grow up, Alex.

ALEX: Yeah, I think that's what it is.

JERRY: Right.

ALEX: Yeah.

JERRY: I gotta grow up.

JERRY: What are you remembering?

ALEX: Just, I've never wanted to grow up. I think it's been like a... I've been a persistently late bloomer my whole life. Yeah, I think there are certain things about my life certain things about my life that I don't... You know, we rent, we don't own a house. There are certain ways in which I'm looking at myself and I'm like, Wow, I'm 50. And I don't have...

JERRY: You're not a grown-up.

ALEX: I'm not a grown-up. Yeah.

JERRY: Does the word "shame" have any resonance?

ALEX: Not... It doesn't feel like... I don't think so. I think "fear" probably has more resonance than "shame."

JERRY: What is there to be afraid of being a grown up or having to grow up? Oh, is it perhaps giving up something?

ALEX: It feels like taking on, like… It becomes more real. It becomes a lot more responsibility. And less fun.

JERRY: And less fun.

ALEX: Less free.

JERRY: Less free. Was your father free?

ALEX: Um... He was. He was very free. In certain ways. In that he never, I think, took on all the responsibilities of adulthood, you know? How did you know that, Jerry? Um... yeah.

JERRY: How did your mother feel about your father not necessarily taking on all the responsibilities of adulthood.

ALEX: Frustrated. And like... But also took care of it.

JERRY: Reluctantly, maybe resentfully.

ALEX: Yeah.

JERRY: Did you see the conflict between the two of them?

ALEX: It never got voiced.

JERRY: It never got voiced. What did it feel like inside, that she was saying. If you could imagine her words, what would they be?

ALEX: You know, I want you to get up off the couch and help think about this stuff.

JERRY: Help think about what stuff? The long-term strategy?

ALEX: Yeah, like help think about the money and help think about the... What would she want him to think about?

JERRY: Where are we going as a family?

ALEX: Think about, yeah, us as a family. Not think about just yourself.

JERRY: Do you hear the echoes?

ALEX: Yeah.

JERRY: I want you to be the CEO of this family." "I don't want to give up my freedom and flexibility." It's time that you grow up. you have to take on all the responsibilities. "But if I take on all the responsibilities then I won't have any fun. So I'm gonna stay in this conflict." And this is, when I talk about understanding our shadow and understanding ourselves, this is what I'm talking about. It's like, what are the constructs that are going on here? Is there anything that you wanna say as we’ve sort of talked through some of this at this point.

ALEX: No I- I think… No I—it’s just striking how when you went back to my parents and my family, like, how resonant that was? And it's just made me think of other things about my-- my family. You know, my dad started a company. My dad was an entrepreneur. And I never, before I started this company, I never ever would have described him that way. Never ever. My mom started an organization. It wasn't a company but it was an organization within the city of Cincinnati, she worked, she was a public employee, but she started this whole, you know, public employee assistance program. She started it, she got the grants for it; she went back to school to get her degree to do it. She did the whole thing. Ran in independently sort of within the city. Was the boss of it. So, she was an entrepreneur, too. Never would have described her that way. And I don't even know—they never used that word. They never talked about how they're business people or the importance of entrepreneurship or anything like that. Um, and then starting this company was the first time I ever even put all of that stuff together. Isn't that curious? I don't know. I don't know what to make of that. But it feels suspect in some way.

JERRY: Oh, it's really fascinating and what's really interesting is their reluctance to use terms like, “I'm a business person, I'm an entrepreneur, I'm a CEO.”

ALEX: Yeah. My dad was a partner in the company. It was 70 people, at its height.

JERRY: Which, your father's?

ALEX: My father's, yeah.

JERRY: Ok, so what role did he play?

ALEX: I don't know what his actual role was. He was a partner—he was a founding partner. It was called Wolf Blumberg Crowtey. Like, he was the name, in the thing.

JERRY: And what did they do?

ALEX: It was an advertising agency.

JERRY: So, what was his... Was he, like, the creative side?

ALEX: Yeah yeah yeah.

JERRY: And so how did he balance... So, he probably had other partners, perhaps, who were more interested in the business side of things.

ALEX: Yeah, Dale. My dad was, like, client-facing. He was the Don Draper, basically, of the whole thing. Um. And um, yeah. Built it, but then didn't... But got increasingly frustrated and then finally left under circumstances—like, left. And they bought him out. So, left with a big chunk of money.

JERRY: And what did he do?

ALEX: Uh, smoked a lot of pot and frittered it away.

JERRY: Look at that.

ALEX: Yeah. I did a story about—

JERRY: Look how emotional you just got. You did a story about him?

ALEX: On TAL. Yeah. Where I talked to him about it. Yeah.

JERRY: The feeling I have right now is that you loved your dad.

ALEX: Yeah, I still do. I mean, yeah.

JERRY: And I think you love your mother.

ALEX: Yeah.

JERRY: Which one was right?

ALEX: Um, I think my mom was right. I think my dad definitely privileged his own wants and desires over those of the family. But he's also a lot of fun. And he's like, you know, and he was incredibly creative and interesting and brought a lot of magic into our family, you know?

JERRY: What is a good man, Alex?

ALEX: I mean, a good man is somebody... I think a good man is somebody who doesn't... who doesn't let their fear control them. I think sometimes that my dad, that's ultimately what my dad did. It wasn't selfishness necessarily, we all have selfish tendencies. But I think he also... The thing that I've tried to do is try to... Like, I think he was afraid of looking at himself directly and sort of, like, acknowledging some of these things.

JERRY: Are you a good man?

ALEX: I am.

JERRY: I wanted to point out to you that what are you doing right now? You're looking at yourself. And it's painful, and it's hard.

ALEX: Yeah.

JERRY: There is a moment in time where we grow past our parents. And you can relate to this because you're both a parent and a son. We want our children to exceed us.

ALEX: Yeah. And my dad, like, I mean, you know, he's just over the moon proud of me, I mean, and he always has been. Um. I definitely want that for my kids, too. Yeah, it's just I mean it's surprisingly emotional. But I think that's also partly why this is an emotional conversation for me. Because I realize that there are these tendencies that we share and I think it's scary. It is scary to think, like, Oh man, could I be self-sabotaging in some way that I'm not aware of, just like my dad?

JERRY: Uh-huh. I'm gonna read you a quote. Bear with me, Jung said something like: Until we make the unconscious conscious, we will be dictated to by it and call it fate.

ALEX: Right. Woah. Why is that making me so upset?

JERRY: Perhaps it's that word "fate." I'm fated to end up like my father. I have to work hard not to end up like my father. But I don't want to become my mother. Resentful.

ALEX: I don't want Matt to become my mother.

JERRY: I don't want Matt to become my mother. Until we make the unconscious conscious. You know that that's what you're doing, right now. You’re already growing past, and doing exactly what your parents want you to do. Which is to grow past them. The same wish you have for your children. Exceed me. Exceed me. Stand on my shoulders and reach higher than I can. Right. So, maybe this is why you cried last night?


ALEX: Two years ago, if someone had told me that starting Gimlet would one day lead to me sobbing in a studio about the patterns of my parent’s marriage, it would have seemed insane.

I didn’t realize those patterns were in me, ready to come out. I have a lot of that 360 review to absorb still. A lot of changes I need to make. I can still feel the urge to retreat into what I know best—the editing and story stuff—and outsource those thorny questions about long-term strategy to Matt. But before this session, I hadn’t known about that behavior. Now I do. And it’s not until you know a thing that you can move past it. That’s part of growing up.


I want to give a  big thank you to my parents. I played the session with Jerry for them before this episode aired. And they’ve also gone through a lot of changes: My dad got sober. They’ve said a lot of things to each other that they hadn’t when I was younger. And just imagine listening as your adult child critiques your performance as a parent in therapy, imagine listening in on that. And now imagine he makes that session public for the world to hear. I wanna say, Mom and Dad, sure you guys had issues, who doesn’t? But the vast majority most of what I got from you is good. I wouldn’t be where I am today without you. I love you a whole lot.


Today’s episode of StartUp was produced by Stevie Lane and Simone Polanen.

It was edited by me, Peter Clowney, Molly Messick, Bruce Wallace, Kaitlin Roberts, Lisa Chow, and Luke Malone. Mark Phillips wrote and performed our theme song. Build Buildings wrote and performed our special ad music. Original scoring by the talented Bobby Lord. Additional music from Takstar and, of course, the band with the greatest band name ever Hot Moms Dot Gov. David Herman mixed the episode. 


To subscribe to the podcast, go to iTunes, or check out the Gimlet Media website: GimletMedia.com. You can follow us on Twitter @podcaststartup.


By the way. Jerry Colonna. He also has a podcast. It’s called The Reboot Podcast, and you can go subscribe to that in iTunes as well. Check it out.


That’s it. Thanks for listening. We’ll see you in two weeks, when we return with the second part of this season. Lisa Chow will be back in the hosting chair, talking about a pretty amazing startup, and a pretty amazing founder. Strap yourselves in. It’s gonna be a good one. We’ll see you next time, on the next episode of StartUp.


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