Latest / "the good work talk show" with mallory contois / the good work talk show | ep. 02 - molly graham

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the good work talk show | ep. 02 - molly graham · "the good work talk show" with mallory contois

• 0:00
  SPEAKER_01: What matters is the days, right?
• 0:01
  SPEAKER_01: What matters is the hours.
• 0:02
  SPEAKER_01: And if you're not excited about the days, then the job is not worth it.
• 0:07
  SPEAKER_01: Every single person in the world has the opportunity to give pieces of their job away.
• 0:12
  SPEAKER_01: What do you want people to think of you for?
• 0:13
  SPEAKER_01: You have to build that before you get opportunity.
• 0:16
  SPEAKER_01: You actually do often discover, like, hey, nobody should ever hire me to do this.
• 0:20
  SPEAKER_01: I know myself really well at this point in my life, but only because I have tried and succeeded and failed.
• 0:26
  SPEAKER_00: Today on Good Work, my guest is Molly Graham, who I am so excited is here.
• 0:31
  SPEAKER_00: She is the founder of Glue Club, a community for all those gluey type people that are keeping everybody's shit together at their companies.
• 0:37
  SPEAKER_00: She's also the author of an incredible essay called Give Away Your Legos, which is often referenced in management conversations.
• 0:44
  SPEAKER_00: And she has been at a number of incredible hyperscale high-growth companies, and so I'm so excited to hear all of those stories today.
• 0:51
  SPEAKER_00: So enjoy.
• 0:57
  SPEAKER_00: I'm Mallory Contoil, and this is Good Work.
• 1:03
  SPEAKER_00: Okay.
• 1:04
  SPEAKER_00: Welcome.
• 1:05
  SPEAKER_00: Very careful.
• 1:06
  SPEAKER_00: Welcome to Good Work.
• 1:07
  SPEAKER_00: Thank you.
• 1:08
  SPEAKER_00: Miss Molly Graham.
• 1:09
  SPEAKER_00: So excited to have you here.
• 1:12
  SPEAKER_00: Okay, so I've told you a little bit about what we do, but we're gonna do two sections.
• 1:16
  SPEAKER_00: We're gonna talk a little bit about how you got to where you are now, and then we're gonna spend a little bit of time just talking about like the concept of work in general.
• 1:24
  SPEAKER_00: Um and the goal is really just to sort of explore your journey.
• 1:28
  SPEAKER_00: And I think sometimes uh these get a little funny because you're probably used to talking less about yourself and more about like other things and other people, but like I really want to hear about like your your life and your career and your decisions and that kind of thing.
• 1:41
  SPEAKER_00: So cool.
• 1:42
  SPEAKER_01: Yeah.
• 1:43
  SPEAKER_00: Okay, we're gonna dive right in.
• 1:45
  SPEAKER_00: Um, the first question I always like to ask is I want to ask about your childhood and I want to ask what you were like as a kid.
• 1:51
  SPEAKER_00: Um, and I'm especially interested if there were any sort of um early influences, people, teachers, uh, I don't know, organizations that like maybe taught you some of the things that you are today.
• 2:05
  SPEAKER_00: But first, what were you like as a kid?
• 2:07
  SPEAKER_01: Yeah, well, I'm the I'm the fourth of four siblings.
• 2:10
  SPEAKER_01: Okay.
• 2:10
  SPEAKER_01: Um, so I think that's probably pretty definitive for me.
• 2:15
  SPEAKER_00: Um what do they say about the youngest?
• 2:17
  SPEAKER_01: Well, they say the youngest is really spoiled and also like has everything taken care of for them.
• 2:23
  SPEAKER_01: Sure.
• 2:23
  SPEAKER_01: And interestingly, I I'm sure I'm spoiled, but actually I'm the organized one in the family.
• 2:29
  SPEAKER_01: I'm the one that like organizes everybody else.
• 2:31
  SPEAKER_01: All of my siblings would agree with this.
• 2:32
  SPEAKER_01: Was that always true?
• 2:33
  SPEAKER_01: Um I mean, once you got to a certain age.
• 2:36
  SPEAKER_01: In high school, I was like stage managing plays.
• 2:39
  SPEAKER_01: Okay.
• 2:39
  SPEAKER_01: You know, my brother was the direct, he was an act, they were an actor and then a director, and I was the stage manager.
• 2:46
  SPEAKER_01: So I kind of think like stage manager is sort of like my personality, and eventually my professional career, more or less.
• 2:55
  SPEAKER_01: Um, so yeah, I don't know.
• 2:56
  SPEAKER_01: I think like uh probably being the fourth of four in a lot of ways, like made me that way.
• 3:03
  SPEAKER_01: Again, my the younger sister drew a very creative brother, and so I think that you often define yourself, I think, in opposition to like your siblings or whatever.
• 3:12
  SPEAKER_01: And so for me, he was creative, so I was like organized and buttoned up.
• 3:16
  SPEAKER_01: He also had a lot of conflict with my parents, and to some extent, like my parents were also they were married, but they got divorced when I was in my 20s, and so I definitely have like a peacemaker vibe.
• 3:30
  SPEAKER_01: Like, I've always been the one that wanted to like hold relationships together.
• 3:34
  SPEAKER_01: Yeah, and I think that was true probably even when I was younger.
• 3:38
  SPEAKER_01: Yeah.
• 3:39
  SPEAKER_01: Um, but when I think about like more formative uh experiences and parts of my life that I think probably have informed like my work, it actually is more like high school and college than it is childhood.
• 3:55
  SPEAKER_00: Yeah, okay, tell me about that.
• 3:57
  SPEAKER_01: It's so funny.
• 3:58
  SPEAKER_01: I was talking to someone the other day, so I did um in college, I did You went to Wesleyan.
• 4:03
  SPEAKER_01: I went to Wesleyan University, yes.
• 4:05
  SPEAKER_01: My um my siblings all went to very fancy colleges, like you know, Oxford and the University of Chicago and Columbia.
• 4:16
  SPEAKER_01: And I the only thing I knew when I was looking at college was I didn't want to go where any of them had gone.
• 4:21
  SPEAKER_01: And I I wanted to go somewhere that that felt uh like it would be open to a diversity of opinions.
• 4:28
  SPEAKER_01: Ended up at Wesleyan.
• 4:30
  SPEAKER_01: Um but I, you know, for me the most formative experiences I've had in my life have actually been experiential education.
• 4:36
  SPEAKER_01: Um, so in high school, I studied abroad my junior year in high school on a farm in Vermont.
• 4:43
  SPEAKER_01: I went to the mountain school.
• 4:44
  SPEAKER_01: Um my dad is from Winooski, so we've spent a bunch of time here.
• 4:47
  SPEAKER_01: Yeah, so the mountain school is in Wersher.
• 4:49
  SPEAKER_01: Okay.
• 4:49
  SPEAKER_01: Um and you live on a farm and you do chores every day.
• 4:52
  SPEAKER_01: You know, you birth lambs and you take care of the chickens and you work in the garden.
• 4:57
  SPEAKER_01: You also go to school and you do your AP classes and all that.
• 5:00
  SPEAKER_01: But it was like that was my first taste of like living an experience rather than just sitting in a classroom.
• 5:06
  SPEAKER_01: And then in college, uh, I guess the summer after my sophomore year.
• 5:11
  SPEAKER_01: My sister had done these mountaineering and sea kayaking courses with this school called Knowles, the National Outdoor Leadership School.
• 5:18
  SPEAKER_01: And I had visited her when she was working for them, and um, because she ended up working in some of their like facilities, and I was like, I hate hiking and I don't like the outdoors, but this looks really cool.
• 5:30
  SPEAKER_01: I it's funny.
• 5:31
  SPEAKER_00: I hate everything about like I maybe I should do it.
• 5:34
  SPEAKER_01: Well, it's funny because I was talking to somebody the other day who was like, Yeah, I looked at Knowles and then I was like, I don't think I'd be good at this, so I never did it.
• 5:39
  SPEAKER_01: And I was like, that's funny.
• 5:40
  SPEAKER_01: I looked at it and was like, I don't think I'll be good at this, why don't I try it?
• 5:43
  SPEAKER_01: Yeah, and and I was thinking about that the other day because this person told me that story of them choosing not to do it, and I was like, what on earth is it about me that made me be like, yeah, let's go do that thing that I think I might hate.
• 5:54
  SPEAKER_01: Yeah, you know, and um and I did Knowles, and the irony, I guess, of me is that I I did a I didn't do a one-month course, which is sort of their like iconic course, I did a three-month course.
• 6:05
  SPEAKER_01: And so I spent 75-if you're gonna do it.
• 6:08
  SPEAKER_01: I mean, I guess.
• 6:09
  SPEAKER_01: So I spent 75 days in Alaska, sea kayaking, backpacking, and mountaineering.
• 6:14
  SPEAKER_01: And by the end of it, they asked me if I wanted to be an instructor.
• 6:17
  SPEAKER_01: Yeah.
• 6:18
  SPEAKER_01: Um, and you know, that ended up being my job right out of college, but it was really, I don't know.
• 6:25
  SPEAKER_01: I mean, again, when I think of themes in my career, just like my life, a lot of it is like been doing things that I didn't think I could do, almost like to prove to myself that I could do them.
• 6:36
  SPEAKER_00: Yeah.
• 6:37
  SPEAKER_00: I was gonna ask if you put yourself back in that, in that moment where you were thinking that of like, I'm not gonna be good at this, but I'm gonna do it anyway.
• 6:44
  SPEAKER_00: Was there like a emotion that was it fear that you were motivated by?
• 6:48
  SPEAKER_00: Was it like you really wanted to prove something?
• 6:51
  SPEAKER_00: Like, and obviously when you're 18, yeah, a lot of times it you might not resonate with what you felt then, but I'm curious like what the driving force was.
• 7:00
  SPEAKER_01: Yeah, what showed up when you asked that question was I think it was curiosity.
• 7:05
  SPEAKER_01: I think there was a lot of fear.
• 7:08
  SPEAKER_01: Um, but for some reason I took that fear as a like, well, a lot of people do this, so like why not you?
• 7:16
  SPEAKER_01: Yeah.
• 7:17
  SPEAKER_01: You know?
• 7:17
  SPEAKER_01: Um instead of like, don't don't do it, you know?
• 7:21
  SPEAKER_01: Um so curiosity is is what shows up for me when you when you ask that.
• 7:25
  SPEAKER_00: Did you have influence from like parents or friends or something that like were they encouraging you?
• 7:31
  SPEAKER_00: Were they discouraging you from those types of like either in high school when you went to work on the in Vermont or like doing that?
• 7:37
  SPEAKER_00: Like, what were those influences like?
• 7:39
  SPEAKER_00: I mean, I think Are you just kind of making these decisions on your own?
• 7:42
  SPEAKER_01: I come from a very supportive family, you know, meaning I think my parents have always been like, we believe in you, what do you want to do?
• 7:50
  SPEAKER_01: And you know, I had worked every summer from the time I was 11.
• 7:53
  SPEAKER_01: 11 was like a being a camp counselor at like our cute neighborhood camp, but I had always had a job and I'd always, you know, um earned money every summer.
• 8:02
  SPEAKER_01: And one summer I had, you know, I was looking for a job and I was having a little bit of trouble finding it.
• 8:09
  SPEAKER_01: And my mom said to me, like, you know, you've always said you wanted to do nobles, why don't you just do that this summer?
• 8:14
  SPEAKER_01: Um, so I think there was always like a little bit of why don't you try things?
• 8:20
  SPEAKER_01: Um, but a lot of it honestly was me.
• 8:22
  SPEAKER_01: I mean, again, fourth of four.
• 8:23
  SPEAKER_01: I think my parents were like, whatever.
• 8:24
  SPEAKER_01: Yeah.
• 8:25
  SPEAKER_01: Like, there was not a lot of like, we're gonna try to control or mold you at, you know, when you're the fourth.
• 8:31
  SPEAKER_00: Yeah, yeah.
• 8:31
  SPEAKER_00: And I imagine you were also, you know, three kids had already gone through a bunch of options and you were like, Well, I don't want to do any of those.
• 8:37
  SPEAKER_00: So, like, you probably ended up in some weird, like outside areas.
• 8:41
  SPEAKER_01: Yeah, well, you sort of like half follow and half try to blaze your own trail, I think.
• 8:45
  SPEAKER_01: Well, at least I did.
• 8:46
  SPEAKER_01: Yeah, I don't know.
• 8:47
  SPEAKER_01: Like, I I went to the schools, you know, they went to until college.
• 8:51
  SPEAKER_01: Um, but I think, yeah, within that I was like, what is mine, you know, and what am I and who am I relative to like all their experiences.
• 8:59
  SPEAKER_01: Um Do you still find yourself thinking about that?
• 9:04
  SPEAKER_01: We're all so different now.
• 9:07
  SPEAKER_01: That no, not at all.
• 9:08
  SPEAKER_01: I mean, I think we all, you know, my brother is uh creative in Hollywood, my sister is a business person, you know, and a founder in her own right, and um, my older sister's an opera singer.
• 9:21
  SPEAKER_01: So, like, and now what do I do?
• 9:22
  SPEAKER_01: Who the hell knows?
• 9:23
  SPEAKER_01: But like, I think um, I think, you know, there has been a journey recently where I realized that I always thought my brother was the creative one, so I wasn't creative.
• 9:33
  SPEAKER_01: Oh, that's interesting.
• 9:34
  SPEAKER_01: So I had to go on a whole journey to like reconnect with like my creative side because I apparently like shut that person in a closet, you know, long ago.
• 9:42
  SPEAKER_01: Um, but mostly no, I think we've all we've all found ourselves, you know.
• 9:46
  SPEAKER_01: Yeah.
• 9:47
  SPEAKER_01: At some point it's your life and you're no one.
• 9:49
  SPEAKER_00: I'm an only child, so I'm always like very interested in sibling dynamics.
• 9:53
  SPEAKER_00: I think it's what our news is.
• 9:55
  SPEAKER_00: I'm like, I mean, listen, being an only child is a whole other experience.
• 9:58
  SPEAKER_00: Um conversation for another day.
• 10:00
  SPEAKER_00: But um, okay, so so you went to Wesleyan, you were studying uh, what do I have?
• 10:05
  SPEAKER_00: History and international relations.
• 10:06
  SPEAKER_00: Is that right?
• 10:07
  SPEAKER_01: Yeah, I studied um every kind of history that was not Europe and the US.
• 10:13
  SPEAKER_01: That was like we had three options US history, European history, or everywhere.
• 10:16
  SPEAKER_01: Everything else.
• 10:17
  SPEAKER_01: I was actually just offensive.
• 10:18
  SPEAKER_01: But I did everything else, and then I did uh yeah, international relations.
• 10:21
  SPEAKER_00: Okay, and that vibe kind of points towards like politics, academia, like generally went to Wesley and studied poly, like that's a certain uh path.
• 10:33
  SPEAKER_00: Was that the plan at that point?
• 10:35
  SPEAKER_00: Did you have a plan, or was that just sort of what you were attracted to at the time and found interesting?
• 10:40
  SPEAKER_01: Mallory, I've never had a plan.
• 10:42
  SPEAKER_01: Yeah, same.
• 10:43
  SPEAKER_00: I mean, I don't know that, especially I don't know that any like 18-year-old really does, but well, I think a lot of them think they do.
• 10:49
  SPEAKER_01: Well, I think they think they do.
• 10:50
  SPEAKER_01: Like I was talking to my um niece the other day, and she's in her early 20s, but I think that we had this conversation when she was 18, and she was like, I'm gonna be a physical therapist.
• 10:58
  SPEAKER_01: And I was like, cool, let's talk in four years.
• 11:00
  SPEAKER_01: Yeah, right, sure.
• 11:01
  SPEAKER_01: Yeah, so I I got really fascinated with um Sub-Saharan Africa in high school, and specifically got really obsessed with Rwanda um and really interested just in a bunch of different stories in Sub-Saharan Africa and Congo and stuff like that.
• 11:15
  SPEAKER_01: So my my junior year, um actually the one of the reasons why I picked Wesleyan was because I knew I wanted to study abroad.
• 11:20
  SPEAKER_01: Yeah.
• 11:21
  SPEAKER_01: And I um they really supported study abroad, which a lot of other colleges didn't at the time.
• 11:26
  SPEAKER_01: Um, and I knew I wanted to go to a French-speaking country because that was the language that I had taken, and um I knew I wanted to go to Africa.
• 11:33
  SPEAKER_01: And so there were actually only two options I could go to Benin or I could go to uh Cameroon.
• 11:39
  SPEAKER_01: And I spent half a year in Cameroon studying abroad my junior year, and then I um ended up writing a thesis.
• 11:47
  SPEAKER_01: I was supposed to go to Rwanda, but for a bunch of very sub-Saharan African reasons, I did not end up going to Rwanda, and I um ended up staying in Cameroon and spending another five months writing a thesis about Cameroon history.
• 12:00
  SPEAKER_01: Um and I think if you had asked me in college, like, what are you gonna be when you grow up, or like where are you gonna go, I would have told you that I was gonna be working for like NGOs, non-governmental organizations in in Africa.
• 12:15
  SPEAKER_01: Like I was gonna be somewhere in Sub-Saharan Africa trying to help out or whatever.
• 12:21
  SPEAKER_01: Better, yeah, make things better, help people um have opportunity.
• 12:25
  SPEAKER_01: And um, yeah, I that is not what I do.
• 12:28
  SPEAKER_01: Yeah, nor is it what I've done.
• 12:30
  SPEAKER_01: But I sort of hope that I'll get back to it at some point.
• 12:33
  SPEAKER_00: There are second, third, and fourth careers that we can all have.
• 12:35
  SPEAKER_01: I see that I see it in your future.
• 12:37
  SPEAKER_01: So my yeah, my mom has this concept of chapters, and I think there's a lot of different chapters in careers.
• 12:42
  SPEAKER_00: I'm a very big believer in seasons or chapters or whatever it is you want to call it.
• 12:46
  SPEAKER_00: Um okay, so let's talk about what you ended up doing, which is going into tech, starting at Google.
• 12:52
  SPEAKER_00: You were at the Center for Foreign Relations, Center for Foreign Relations in the United States.
• 12:56
  SPEAKER_00: Council, council.
• 12:57
  SPEAKER_00: I was like CFR.
• 12:58
  SPEAKER_00: Okay, council.
• 12:59
  SPEAKER_00: You ended up there and then you went to Google.
• 13:00
  SPEAKER_00: Can you talk me through the decisions that happened in that maybe two-year, three-year period?
• 13:06
  SPEAKER_01: Yeah, for sure.
• 13:06
  SPEAKER_01: So I worked as an instructor at Knowles for a year, um, leading trips in Patagonia, um, outdoor trips.
• 13:13
  SPEAKER_01: And then I don't even remember exactly what happened, but I was like, I want a job.
• 13:18
  SPEAKER_01: And I applied to one job at CFR.
• 13:21
  SPEAKER_01: And uh why that job?
• 13:23
  SPEAKER_01: So I it was really looking at sort of like my history, my background, like my um what I studied in college, and thinking the Council on Foreign Relations does a huge amount of policy work.
• 13:34
  SPEAKER_01: They basically try to influence um the foreign relations policy of the government by being a think tank.
• 13:40
  SPEAKER_01: And what a think tank does is basically hire really smart people and have them write, the, you know, speak, um go on shows uh to put ideas out there that then they hope will make it into like the policy of the government.
• 13:52
  SPEAKER_01: And so uh there was a job available for um their publications department, and they publish like a really famous magazine called Foreign Affairs, but they also publish all these like books and think pieces that are separate from foreign affairs, and so it was like all of that stuff.
• 14:06
  SPEAKER_01: And I was like, I know how to write, I good at writing.
• 14:09
  SPEAKER_01: So I uh learned how to copy edit in order to do their test and applied, and they uh the woman who ran the department picked my resume because I knew how to do CPR, and she thought I would be good at managing stress, and so which you know goes to show you never know if you are or are not qualified for a role and you should apply no matter what.
• 14:32
  SPEAKER_01: You should apply no matter what, and the reason why you'll get picked is well, I think it's also like always put the always put the weird on your resume, because like often that's what people like pulls you out of the stack, but um but yeah, so I I got that job.
• 14:45
  SPEAKER_01: I had to buy a suit to show up in New York at this like fancy think tank, and I had an amazing year and a half working with her and learning from her, and also sitting inside this crazy organization that um, you know, just so many fascinating people and events.
• 14:58
  SPEAKER_01: Um, but we were a book search partner to Google.
• 15:01
  SPEAKER_01: So, like hard to remember what Google was like back then, but like this is 2005-2006, where their you know mission was to organize the world's information and make it universally useful and accessible, and they had a goal to like you know index every book in the world and you know, foreign the council.
• 15:15
  SPEAKER_01: It still really rolls off your tongue.
• 15:16
  SPEAKER_01: Council on foreign relations, yeah, totally.
• 15:18
  SPEAKER_01: I mean, it was a great mission.
• 15:20
  SPEAKER_01: And um, oh so the Council on Foreign Relations has all this material, so they were partnered with Google, and our book search partner, you know, I would email with him and he came in to meet us at some point, and I, you know, we had the meeting and I walked him to the door and he looked at me and he said, Have you ever thought of working at Google?
• 15:35
  SPEAKER_01: And I was like, No, I was like, What is I was like, isn't that just like a white website with a box on it?
• 15:42
  SPEAKER_01: Like, do people work there?
• 15:43
  SPEAKER_01: You know, and I it was like I'm being overly simplistic because you know, it had just gone public a couple years earlier, and so like they had there had been a lot of stories about its culture and the bouncing balls and all that that they had people sitting on, and but I genuinely was like, no, I've never thought of it.
• 15:58
  SPEAKER_01: But then I just couldn't stop.
• 16:00
  SPEAKER_01: Like, I think he asked the question, and it like sometimes these things just like stick in your brain.
• 16:05
  SPEAKER_01: And I was like an earworm with music, totally, yeah.
• 16:08
  SPEAKER_01: And so I was like, okay, I'm gonna apply.
• 16:12
  SPEAKER_01: And I reached out to him and I said, I said, what should I apply for?
• 16:15
  SPEAKER_01: And he was like, girl, like find your own path.
• 16:17
  SPEAKER_01: Like, like you apply and then tell me, and I'll like put my name on your resume, you know.
• 16:23
  SPEAKER_01: Um, so I applied and he, you know, put his stamp on my resume, and I've never heard anything back.
• 16:29
  SPEAKER_01: And um, but the earworm was there, and so I started to like look around, and I had lunch with a friend uh who is a friend of my parents, but I knew her really well, and I said, you know, she was just asking me questions, and I was like, Oh yeah, like I got kind of interested in Google, and she was like, Oh, my friend just took a job there as the head of communications, and I was like, Oh, and she was like, Do you want me to introduce you to him?
• 16:48
  SPEAKER_01: And I was like, Yeah.
• 16:50
  SPEAKER_01: Yeah, and so she introduced me to him, and I ended up getting a job in the communications department a while later.
• 16:56
  SPEAKER_00: Um and you could have said no in that way, you could have said, like, oh no, no, no, don't worry about it.
• 16:59
  SPEAKER_00: But you were just, did that feel easy to just be like, oh yeah, or was that a moment where you were like, ooh, like I don't know.
• 17:05
  SPEAKER_01: I think it felt easy at the time because I really had gotten excited about working there and I had no idea how to get inside.
• 17:12
  SPEAKER_01: And um, yeah, so at the moment it, yeah, at the moment it felt easy.
• 17:19
  SPEAKER_01: But yeah.
• 17:20
  SPEAKER_00: Okay, and did you have so it's I heard a little bit of like you kind of knew what you were walking into, not totally, but like not at all.
• 17:27
  SPEAKER_00: What did you what what happened when you got into Google?
• 17:30
  SPEAKER_00: Like, what did you learn in the first 30, 60 days that you were just like, oh, okay, this is like what's happening?
• 17:35
  SPEAKER_01: Oh, it's funny.
• 17:36
  SPEAKER_01: I mean, uh that year is one of the things I call a Phoenix year, where you know, everybody, well, lots of people end up in these years where you kind of burn everything down in your life.
• 17:48
  SPEAKER_01: Um, so I was living in New York and I moved to Palo Alto, California.
• 17:53
  SPEAKER_01: I'd never been to California before.
• 17:55
  SPEAKER_01: I think I'd been to the San Francisco airport once.
• 17:57
  SPEAKER_01: Um and I my parents got divorced that year, and I also broke off like a really big long-term relationship that year.
• 18:04
  SPEAKER_01: So we just burnt all the things to the ground.
• 18:06
  SPEAKER_01: Yes.
• 18:06
  SPEAKER_01: Um, and yeah, I got to Google and I was super lucky because it was growing really fast.
• 18:12
  SPEAKER_01: And my department was like 25 people at the time, but they had hired 20 like folks just out of college.
• 18:20
  SPEAKER_01: Um, they were, you know, a year or two behind me, but like basically they hired me a set of friends.
• 18:26
  SPEAKER_01: And so we had this incredible um set of folks that just showed up and became, you know, I still have uh a lot of friends from that chapter because we all got to like show up and and grow up together at Google in that crazy period because we that department went from 25 people to 125 people in nine months.
• 18:45
  SPEAKER_00: Nothing like high growth trauma bonding.
• 18:47
  SPEAKER_00: Yeah, exactly.
• 18:48
  SPEAKER_01: I mean, at the time it all just felt fun, you know.
• 18:50
  SPEAKER_01: Um, but it was a fascinating chapter.
• 18:54
  SPEAKER_01: And I think I barely remember the first three months because it was such a um, it was such a tornado.
• 19:04
  SPEAKER_01: Yeah.
• 19:04
  SPEAKER_01: I mean, it was a professional tornado just in the like, what is this place and what's my job and all that, but it was also um, yeah, just like uh there was so much happening.
• 19:16
  SPEAKER_01: And I was working on the Google blogs at the time, so like every week it was like what are we announcing and writing all of that?
• 19:22
  SPEAKER_00: And yeah, yeah, yeah.
• 19:23
  SPEAKER_00: That's so cool.
• 19:24
  SPEAKER_00: And then you ended up at Facebook.
• 19:27
  SPEAKER_01: Yes, a year and a half later.
• 19:28
  SPEAKER_00: A year and a half later.
• 19:29
  SPEAKER_00: And I'm specifically I'm I'm interested in two things about that transition.
• 19:32
  SPEAKER_00: Why one did you why did you decide to leave Google and go to Facebook?
• 19:34
  SPEAKER_00: And then the second one is that transition you made in the middle of Facebook from comms to leading mobile, which from the outside looks bizarre.
• 19:42
  SPEAKER_00: From the inside, I'm sure there was rhyme and reason and a pattern.
• 19:45
  SPEAKER_00: But I'd I'd love to hear a little bit of of what that felt like for you.
• 19:49
  SPEAKER_01: Well, to be honest, like um one of the things you'll find and like very much the same story as like ending up at Google is like that was a happy accident following intuition, following something that just like felt right.
• 20:00
  SPEAKER_01: Yeah.
• 20:01
  SPEAKER_01: Um, halfway through my time in communications at Google, my it turned out that the head of communications was looking for a chief of staff, and I just said to his EA, hey, would he consider me?
• 20:11
  SPEAKER_01: Um, because I was like, I think I can help organize this shit.
• 20:13
  SPEAKER_01: Um you were already stage managing your six years.
• 20:17
  SPEAKER_01: These meetings are basically the same.
• 20:19
  SPEAKER_01: Like, let me make them better.
• 20:20
  SPEAKER_01: And um, so I worked for Elliot Shrig, who's the head of communications at Google, for a year, and then he left.
• 20:28
  SPEAKER_01: Um, he left and went to Facebook.
• 20:29
  SPEAKER_01: Um, he was one of Cheryl's best friends, so Cheryl Sandberg left and went to Facebook.
• 20:33
  SPEAKER_01: Six months later, Elliot left and followed her.
• 20:36
  SPEAKER_01: And as soon as he left, everyone looked at me and was like, Are you going to Facebook?
• 20:40
  SPEAKER_01: Um, and I I definitely remember being pretty sad and torn at the time because I didn't feel like I was done at Google, you know.
• 20:47
  SPEAKER_00: How long had you been there?
• 20:49
  SPEAKER_01: A year and a half, not very long.
• 20:50
  SPEAKER_01: Yeah.
• 20:50
  SPEAKER_01: Um, and but I but I looked around at Google.
• 20:53
  SPEAKER_01: I actually looked at the self-driving initiative.
• 20:55
  SPEAKER_01: Um, it's funny.
• 20:56
  SPEAKER_01: Uh, they were looking for a PM.
• 20:58
  SPEAKER_01: I talked to them.
• 20:58
  SPEAKER_01: I looked at like a job in Zurich working for the head of engineering there, and I looked at Facebook because I just wanted to follow Cheryl and Elliot.
• 21:06
  SPEAKER_01: Like I literally barely was a user of Facebook.
• 21:09
  SPEAKER_01: I did not understand anything about the company's mission or vision.
• 21:12
  SPEAKER_01: I just wanted to work for Cheryl and Elliot.
• 21:14
  SPEAKER_01: And so I applied to all three of those jobs and was having all these conversations, and I got, you know, got, I think, two offers.
• 21:22
  SPEAKER_01: One was in Zurich and one was at Facebook.
• 21:25
  SPEAKER_01: And I was talking to my therapist at the time, and she said, you know, I was so conflicted.
• 21:29
  SPEAKER_01: And she just said, I think you have the answer inside of you.
• 21:31
  SPEAKER_01: Why don't you just go listen for it?
• 21:33
  SPEAKER_01: And I like remember going home.
• 21:35
  SPEAKER_01: Classic therapist.
• 21:36
  SPEAKER_01: It was great.
• 21:36
  SPEAKER_01: I remember going home and sitting on my porch and having a beer, and I it just like outside out of me came, I just want to go to Facebook.
• 21:42
  SPEAKER_01: Like, I just want to go work for these people.
• 21:44
  SPEAKER_00: Yeah.
• 21:45
  SPEAKER_01: And I showed up on day one.
• 21:47
  SPEAKER_01: I I was in Elliott's, I was in the communications department initially, and I remember sitting through orientation listening to this guy, Chris Cox, who's still at Facebook today, talk about what they were planning, you know, what the vision of Facebook was.
• 21:59
  SPEAKER_01: And I remember being Like, wow, this place is really the ambition here is a lot bigger than I understood.
• 22:04
  SPEAKER_01: Like, I just like I mean it was smaller than MySpace at the time.
• 22:06
  SPEAKER_01: It had just taken an investment from Microsoft, and everybody was like, it's just gonna get bought by Microsoft.
• 22:11
  SPEAKER_01: And I came there thinking, I don't know, I'm just following these awesome people.
• 22:15
  SPEAKER_01: Um, so like no sense of the scope or scale that was coming.
• 22:19
  SPEAKER_01: Um, but I literally lasted three months in the communications department at Facebook.
• 22:24
  SPEAKER_01: Like I almost immediately was asked by Chris Cox, who was then the head of HR, to go into HR.
• 22:32
  SPEAKER_01: And, you know, again with the no plan, like he was like, hey, I'm, you know, we built these values.
• 22:38
  SPEAKER_01: I want someone to come help me figure out how to like scale them.
• 22:40
  SPEAKER_01: And I was like, okay, uh, sure, sounds fun.
• 22:43
  SPEAKER_01: And I told Elliot and he was like, okay.
• 22:45
  SPEAKER_00: Was it really that, like, people are gonna listen to this and be like, there's no way it was that easy in that like low friction?
• 22:51
  SPEAKER_00: Was it really that?
• 22:52
  SPEAKER_00: Like, I think what I'm trying to get at is sometimes you can follow your intuition and it actually is that easy.
• 22:58
  SPEAKER_00: Yeah.
• 22:59
  SPEAKER_00: I've had that experience, and then I've also had that experience where looking back, you're like, yeah, I think I just said yes, but then you think about it, and you're like, well, actually, like there were some people that were mad at me, and like there were a couple people that were stressed, and I was stressed, but then I made this decision.
• 23:10
  SPEAKER_00: Which one of those was it?
• 23:12
  SPEAKER_01: In the case of going to Facebook, it was very stressful.
• 23:15
  SPEAKER_01: Yeah.
• 23:16
  SPEAKER_01: Um, that was like one of my first big career decisions.
• 23:18
  SPEAKER_01: So I felt very I don't know.
• 23:20
  SPEAKER_01: It's like you have to learn how to make those decisions, and they feel very stressful the first bunch of times, and then you get used to the stress.
• 23:26
  SPEAKER_01: You just it feels familiar.
• 23:28
  SPEAKER_01: Um in the case of going from communications to HR, that was not stressful.
• 23:32
  SPEAKER_01: It was really easy.
• 23:33
  SPEAKER_01: And I no one was mad at me.
• 23:35
  SPEAKER_01: Like everyone was like, you should go do this.
• 23:37
  SPEAKER_01: And um, there were many odd, ironic things that happened.
• 23:41
  SPEAKER_01: Like basically, me going into HR prompted Chris to Mark was looking for a head of product, and Chris he had asked Chris like casually, and Chris was like, Let me just go make sure that Mark doesn't want me to be the head of product, and then he came back and he was like, Mark wants me to be the head of product, so like I'm gonna go over there.
• 23:56
  SPEAKER_01: But he was like Lori Gowler, who's the head who became the head of people at Facebook for 15 years, and she and I had started on the same day, so I already knew her.
• 24:03
  SPEAKER_01: He was like, She's gonna come in, and you can be her right hand, and I was like, Okay.
• 24:08
  SPEAKER_01: So I don't know, but I also think, and you probably remember this from your time at Pinterest, when you're in a company that's growing as fast as Facebook was at that time, these moves are very organic.
• 24:16
  SPEAKER_01: Like nobody really expects you to stay in the same place all that long because, like, and it's a very particular type of hypergrowth.
• 24:23
  SPEAKER_01: There's like, there's no growth, there's growth, and then there's true hypergrowth.
• 24:26
  SPEAKER_01: And Facebook was like hyper hyper growth.
• 24:29
  SPEAKER_01: I mean, we were adding 10 million users every month.
• 24:31
  SPEAKER_01: It was nuts, you know, at the time.
• 24:34
  SPEAKER_01: Um, and I uh so so it was very like fluid and organic, and and I just remembered thinking that as long as the problem was interesting, I didn't really care.
• 24:46
  SPEAKER_01: You know, and I so I I went into HR for two years and just really worked as Lori's kind of her right hand, but a lot of it was like, you know, external branding because she was a marketer, and so she wanted to think about like how we talked about who we were, you know, why why come work at Facebook and then um internal work around what was kind of called culture, but it ended up being like all the big systems.
• 25:08
  SPEAKER_01: So it was like performance and compensation and engagement and building all of that early stuff at Facebook.
• 25:15
  SPEAKER_01: Um, and and then I was doing that and I was perfectly happy.
• 25:20
  SPEAKER_01: And I planned to stay doing it until we went public.
• 25:24
  SPEAKER_01: Like I thought it would be really interesting to like be working in HR in this role when we went through that sort of what felt like a big transformation as a company.
• 25:31
  SPEAKER_01: And I had lunch one day with this guy named Schmoth, who's now very famous.
• 25:35
  SPEAKER_01: He's the guy that he's on the all-in podcast, all that.
• 25:38
  SPEAKER_01: But um, at the time he was running mobile and growth at Facebook, and he is a very he loves being controversial.
• 25:44
  SPEAKER_01: So he said to me, you know, what are you doing in HR?
• 25:47
  SPEAKER_01: It's so useless.
• 25:48
  SPEAKER_01: What a waste of your time.
• 25:50
  SPEAKER_01: Like you should come work for me.
• 25:51
  SPEAKER_01: And I was like, whatever, Schmoth.
• 25:53
  SPEAKER_01: Like, yeah.
• 25:54
  SPEAKER_01: And he was like, Do you want to come do this?
• 25:56
  SPEAKER_01: Like, do you want to come work on international growth?
• 25:57
  SPEAKER_01: Do you want to come, you know, do this other thing?
• 25:59
  SPEAKER_01: And I was like, No.
• 26:00
  SPEAKER_00: Why do you think it was that people kept tapping you for these opportunities?
• 26:05
  SPEAKER_01: So, you know, I thought a lot about that because um because that doesn't happen to everyone.
• 26:09
  SPEAKER_01: It doesn't happen to everyone, but I think there's basically two things.
• 26:12
  SPEAKER_01: Like, one is when you get inside a company, your job is to be useful.
• 26:16
  SPEAKER_01: Your job is to show up and figure out like what can I do that makes this place better, more successful.
• 26:20
  SPEAKER_01: And I think that was always just my orientation.
• 26:22
  SPEAKER_01: Like my first three months in communications, I sat in a meeting of 20 people organizing F8, which was like Facebook's big um conference every year, developer conference.
• 26:32
  SPEAKER_01: And there was like this whole like who's organizing the breakout sessions, and they were all like pointing their fingers at each other, and I was like, Do you want me to just organize them?
• 26:38
  SPEAKER_01: And so I, you know, I just ran all the breakout sessions for F8 that year.
• 26:42
  SPEAKER_01: And I think that vibe of just like, what can I do to help?
• 26:46
  SPEAKER_01: Like, not trying to get credit, not trying to be known for a thing, not trying to like be a thing, but just be like helpful.
• 26:52
  SPEAKER_01: I did that over and over and over again, and I think it served me really well because eventually, once you're someone that people know, like, oh, if I hand this to Molly, like it will get done.
• 27:00
  SPEAKER_01: Yeah.
• 27:00
  SPEAKER_01: Right.
• 27:00
  SPEAKER_01: If I hand this to Molly, she'll think it through, she'll, you know, she'll kind of handle it well.
• 27:03
  SPEAKER_01: Then they want to hand you more things, you know?
• 27:06
  SPEAKER_01: And um, so with in the case of like Chamath, I had basically Mark had come to me and Lori and said, we want to rewrite the company values.
• 27:13
  SPEAKER_01: And if initially we were like, no, like you can't write rewrite the company values, like that's not a thing.
• 27:18
  SPEAKER_01: And then it turns out he was CEO, so he can do whatever he wants.
• 27:21
  SPEAKER_01: But like also, it was a really interesting exercise because it turned out he really wanted to have a conversation with the company about like these values and like how they were evolving as we grew and and and sort of what needed to stay the same and what needed to change.
• 27:34
  SPEAKER_01: So I led that and Schmoth got very involved in it for a bunch of reasons.
• 27:38
  SPEAKER_01: And so I think he liked working with me.
• 27:40
  SPEAKER_01: I have no idea.
• 27:41
  SPEAKER_01: He's he's a mystery man.
• 27:42
  SPEAKER_01: Sure.
• 27:43
  SPEAKER_01: And so so I think then he sort of had an idea of like, ooh, I should like, he likes to collect people.
• 27:49
  SPEAKER_01: That's kind of one of his things.
• 27:50
  SPEAKER_01: And so I think any successful leaders, that's kind of their thing.
• 27:53
  SPEAKER_01: Yeah, totally.
• 27:54
  SPEAKER_01: So I think he was just collecting me.
• 27:55
  SPEAKER_01: Like, I don't I don't think he really cared what I did.
• 27:58
  SPEAKER_01: He just wanted me on his team, and um, which is nice.
• 28:01
  SPEAKER_00: Um, and so that that like building trust through being helpful over and over again, I think is kind of the the thing that got you into these positions.
• 28:10
  SPEAKER_01: It's the thing I tell people that sometimes is the missing piece.
• 28:14
  SPEAKER_01: Like you, you know, let's say, like a lot of times I talk to people that are like, I want, you know, I'm in HR and I want to be in operations or I'm in finance and I want to be, you know, whatever, in product.
• 28:24
  SPEAKER_01: I'm like, you don't, you don't get there by, you know, either A, applying cold into product when your whole background is finance, and and B, you don't get there like three months into the company, usually, particularly if it's not in hypergrowth.
• 28:35
  SPEAKER_01: You get there by like being exceptional in finance, figuring out how to be useful to people, and and figuring out sort of like what is the connective tissue between you and that other role.
• 28:44
  SPEAKER_01: Yeah.
• 28:45
  SPEAKER_01: And then eventually it becomes really obvious.
• 28:47
  SPEAKER_01: Like a lot of times you get offered jobs because you're already doing them, you know.
• 28:51
  SPEAKER_01: Um, and but I do think just in general, like so much of the most important fabric that you build early in a career is about people thinking, you know, they have a challenge, they're like, oh, I want this person for that challenge.
• 29:07
  SPEAKER_00: Who can I trust to solve this problem?
• 29:08
  SPEAKER_01: Yeah, I mean, that is life is so much, you know, careers are so much built out of relationships where somebody is presented with a problem and then they think of you.
• 29:16
  SPEAKER_01: Yep.
• 29:17
  SPEAKER_01: And so it's like, what do you want people to think of you for?
• 29:19
  SPEAKER_01: Yeah.
• 29:19
  SPEAKER_01: And a lot of you have to build that before you get opportunity.
• 29:22
  SPEAKER_01: Yeah.
• 29:23
  SPEAKER_01: And um, yeah, I think I did that at Facebook and at Google, you know, um, and that's really what presented these opportunities to me.
• 29:31
  SPEAKER_00: Yeah.
• 29:32
  SPEAKER_00: Okay.
• 29:33
  SPEAKER_00: So then you go on, you're COO, head of ops at a bunch of amazing companies, quick, quick, Quip, Quip, Chan Zuckerberg Initiative, Lambda School, and then you decide to go out on your own.
• 29:46
  SPEAKER_00: At what point did you we're gonna it feels funny to skip over all of that because that's incredible, all very impressive, but I'm curious actually at what point you decided you were done with corporate, or it was time to take a bet on yourself, or it was time to take a break.
• 29:59
  SPEAKER_00: Like, what did that look like?
• 30:00
  SPEAKER_00: Because I think a lot of people find themselves in that position sometimes where they're like, man, I don't know if corporate's serving me anymore.
• 30:07
  SPEAKER_00: What did that decision matrix look like for you?
• 30:10
  SPEAKER_01: Um, to be honest, like, so yeah, so I spent um 10 years sort of with my title as COO and um helping visionary people build their companies is probably how I would describe what I was doing.
• 30:23
  SPEAKER_01: And I think in the second or third iteration of that, I really realized that I wasn't learning as much anymore.
• 30:31
  SPEAKER_01: Um, it didn't necessarily initially have anything to do with like corporate or not corporate.
• 30:36
  SPEAKER_01: It was just like, oh, I've been doing this job, and learning is really important to me.
• 30:40
  SPEAKER_01: It's like definitely been a really big driving force in my career that I I like being on a learning curve like so steep that I'm terrified, and that's a very particular kind of learning.
• 30:51
  SPEAKER_01: And um there was this real moment when I got a call about a CEO job where I was like, you called the right person.
• 30:58
  SPEAKER_01: Like I would be fucking great at this job.
• 31:00
  SPEAKER_01: Like I'm like I this CEO is a very particular CEO.
• 31:04
  SPEAKER_01: I know how to handle this kind of crazy, brilliant, crazy.
• 31:09
  SPEAKER_01: And they all are.
• 31:10
  SPEAKER_01: And and I um I really think I'd be miserable taking this job.
• 31:15
  SPEAKER_01: So it was this interesting contrast of like, wow, I'm really good at this, I'm known for it, I'm getting the right calls, and I no longer think it is my work.
• 31:22
  SPEAKER_01: Um, and that was really hard for a bunch of reasons because I, you know, all of these jobs start to sound cooler and cooler, and you're like, everybody would think I was so awesome if I took this job.
• 31:34
  SPEAKER_01: And like, um, but I had to learn to kind of like quiet those egotistical voices and sort of realize that yeah, the the moment you posted on LinkedIn might be cool.
• 31:44
  SPEAKER_01: I call it a LinkedIn crush, right?
• 31:46
  SPEAKER_01: Like you're excited about saying that you had the job, but you're not excited about doing the job.
• 31:51
  SPEAKER_01: And for me, and I think for everyone in the world, like what matters is the days, right?
• 31:55
  SPEAKER_01: What matters is the hours.
• 31:57
  SPEAKER_01: And if you're not excited about the days, then the job is not worth it.
• 32:01
  SPEAKER_00: Yeah.
• 32:02
  SPEAKER_01: Um, so you know, for a bunch of reasons, I that actually led me on a okay, well, what does sound fun and what does sound interesting?
• 32:09
  SPEAKER_01: And I explored being a CEO.
• 32:10
  SPEAKER_01: I explored working at much bigger companies than I'd ever worked at, and you know, various things.
• 32:16
  SPEAKER_01: And I just realized that I didn't want to do any of that anymore.
• 32:19
  SPEAKER_01: What did that exploration look like?
• 32:20
  SPEAKER_00: Was it having conversations with people?
• 32:22
  SPEAKER_00: Was it I don't know.
• 32:23
  SPEAKER_00: Yeah.
• 32:24
  SPEAKER_01: It was just putting feel.
• 32:24
  SPEAKER_01: I mean, at this point, you know, I'm 15 or 20 years into my career, and I have a lot of friends, so I can just be like, hey, I'm thinking about this.
• 32:31
  SPEAKER_01: What do you think?
• 32:31
  SPEAKER_01: What do you you heard about?
• 32:32
  SPEAKER_01: Oh, you're a CEO, you took over someone else's company.
• 32:35
  SPEAKER_01: Like, what's that been like for you?
• 32:36
  SPEAKER_01: Like, and it let me have physical reactions to what you know, people you interview for stuff and you're like, I hate this, or I'm excited about this.
• 32:43
  SPEAKER_01: And so it's just, you know, putting feelers out.
• 32:46
  SPEAKER_01: And for me, it was basically developing a theory of like three paths.
• 32:49
  SPEAKER_01: It was like, do you want to be a CEO?
• 32:50
  SPEAKER_01: Do you want to, you know, take a big C-level job at some fancy company, or do you want to start your own thing and sort of slowly ruling those out.
• 32:58
  SPEAKER_01: And what happened to me was actually the thing that people say, which is like you shouldn't start something yourself unless you're you can't think of anything else you want to do.
• 33:06
  SPEAKER_01: And that's basically what happened where I just I was like, I don't want to be a I don't want to be a turnaround CEO for a bunch of reasons, and I um didn't want the C-level jobs anymore.
• 33:16
  SPEAKER_01: I was like, I think if somebody tries to give me a performance review, I'll rip their face off.
• 33:20
  SPEAKER_01: And um, yeah, so I was like, I think I gotta start something, and it it didn't start with a lot of energy, you know.
• 33:25
  SPEAKER_01: It started with just a like, okay, what are we doing, you know?
• 33:28
  SPEAKER_01: And and then it's, you know, for me, it's been a journey of like, what is that?
• 33:33
  SPEAKER_01: Um, but it wasn't like as conscious as like I'm leaving corporate.
• 33:38
  SPEAKER_01: It was like, I'm I this path is the only one that feels like it has any energy or learning behind it.
• 33:44
  SPEAKER_00: Yeah.
• 33:44
  SPEAKER_00: A huge thank you to my friends at Granola for sponsoring the Good Work Talk Show.
• 33:48
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• 33:57
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• 34:08
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• 34:15
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• 34:20
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• 34:22
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• 34:27
  SPEAKER_00: Cranola also has features for following up and for drafting to-do lists.
• 34:31
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• 34:36
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• 34:39
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• 34:45
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• 34:48
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• 34:52
  SPEAKER_00: Okay, granola's been listening to us.
• 34:54
  SPEAKER_00: I asked granola and it's been transcribing and taking notes.
• 34:57
  SPEAKER_00: I asked it what we should talk about next, what question I should ask you.
• 35:00
  SPEAKER_00: And its suggestion was uh, what made you realize that COO, CEO paths could be attractive but still wrong for you?
• 35:08
  SPEAKER_00: And I'm gonna expand on the question just a little bit because I know you said I would be miserable, but I'm curious how you like how you evaluated that tactically.
• 35:17
  SPEAKER_00: I'm thinking about people who are looking down a path of taking a new role.
• 35:20
  SPEAKER_00: Maybe it's changing companies, maybe it's taking a management role from an IC.
• 35:25
  SPEAKER_00: What are the like, what are the things that you think you should evaluate?
• 35:29
  SPEAKER_00: I I think this might be a good opportunity for your three-legged stool uh framework, but like, how do you evaluate happiness in a role, or how do you think people should decide whether or how do you how can they best predict whether they're going to be happy in a role?
• 35:45
  SPEAKER_01: Yeah, um, well, I'll give you the the example of sort of exploring being a CEO.
• 35:50
  SPEAKER_01: Um and in the case of that exploration, what I was actually exploring was like taking over somebody else's company, um, which is a very particular type of CEO role.
• 36:01
  SPEAKER_01: Um because the other option is to be a founder, right?
• 36:04
  SPEAKER_01: To build something yourself.
• 36:05
  SPEAKER_01: And um, so what I did was I basically reached out to a bunch of recruiters I knew that recruited for CEO roles and asked them sort of like what was available and what they had seen, and you know, these were friend friends that were recruiters, so it was like really easy to have a dialogue about what they saw in the market in terms of the opportunities, but also what they saw in terms of the qualities inside the role.
• 36:29
  SPEAKER_01: Um and it it just helped me realize that as one of my friends Sam Holy would say, uh, there's a reason why they're looking for a CEO.
• 36:38
  SPEAKER_01: And his point was like, companies that are doing really well don't look for CEOs.
• 36:43
  SPEAKER_01: Um they so so usually there's a problem um and you're there to fix it.
• 36:49
  SPEAKER_01: Um and then I also called, so like that was one thing he was saying, which was like, you're coming in to turnaround a company, you're coming in to fix a problem.
• 36:55
  SPEAKER_01: Like, are you interested in that work?
• 36:57
  SPEAKER_01: Um, and then I also called a bunch of friends that had taken CEO jobs just to ask, like, what they wish they'd known and what their days were like.
• 37:05
  SPEAKER_01: And um a lot of times these jobs show up, you know, because a private equity firm has bought a company and they're looking to place a CEO or something like that.
• 37:14
  SPEAKER_01: And it just taught me a lot about the dynamics that I might be buying into.
• 37:17
  SPEAKER_01: Um, and then I interviewed for some roles, um, had some conversations with boards that were thinking about looking for a CEO or that looking for a CEO.
• 37:24
  SPEAKER_01: And I basically realized two things.
• 37:26
  SPEAKER_01: Like one, it was gonna take a very long time to find one that I was excited about.
• 37:29
  SPEAKER_01: Like I was looking at like a three to five year search because it just they don't show up all that often.
• 37:34
  SPEAKER_01: It has to be a fit between you and the company and the role and the board and all these things.
• 37:39
  SPEAKER_01: Um and uh, and that basically I was probably walking into a turnaround, right?
• 37:45
  SPEAKER_01: I was probably walking into somebody took a shit all over everything, and like you have to like clean up the mess.
• 37:49
  SPEAKER_01: Yeah.
• 37:49
  SPEAKER_01: And which can be fun.
• 37:51
  SPEAKER_01: It is fun for some people, it's not fun for me.
• 37:53
  SPEAKER_01: I I've done it and I it was just not the work that I was excited to do.
• 37:57
  SPEAKER_01: Yeah.
• 37:58
  SPEAKER_01: But I have friends that fucking love that.
• 38:00
  SPEAKER_01: Would you have known that it wasn't the work you like if you hadn't done it before?
• 38:04
  SPEAKER_01: No, I think I I think I would have potentially been excited about it because it was something new.
• 38:09
  SPEAKER_01: In this case, I was like, I kind of did that.
• 38:11
  SPEAKER_01: Yeah.
• 38:12
  SPEAKER_01: And I didn't like it.
• 38:13
  SPEAKER_01: Um, or it just wasn't my strongest and greatest use.
• 38:16
  SPEAKER_01: Um and it just wasn't what I was looking forward to doing now, you know.
• 38:20
  SPEAKER_01: And again, learning is so important to me that I a lot of this is about like, what is it that you want to learn next, you know?
• 38:27
  SPEAKER_01: Um, but I think that that those conversations were uh incredibly helpful just in giving me a pretty quick sense that like this wasn't gonna be my path.
• 38:39
  SPEAKER_01: Um and you know, you mentioned the three-legged stool.
• 38:42
  SPEAKER_01: Interestingly, like that's a that is like a that was a metaphor that I came up with when I was at Quip, which is this um SaaS startup that I helped build.
• 38:52
  SPEAKER_01: It was uh trying to be kind of like doc like think of it as like Microsoft Office on your phone and tablet and all that, so like cross-device um collaboration.
• 39:01
  SPEAKER_01: And I actually took that job knowing that I wasn't super passionate about SaaS software.
• 39:06
  SPEAKER_01: Yeah.
• 39:06
  SPEAKER_01: Like I wasn't like, and productivity in the street.
• 39:07
  SPEAKER_01: So what you dreamed to work on?
• 39:09
  SPEAKER_01: Well, some people love productivity and can tell themselves a whole story about like making every company in the world more efficient makes something, you know, better.
• 39:15
  SPEAKER_01: Sure.
• 39:16
  SPEAKER_01: Um, but for me, I was like, you know, I'm taking this job because of the person that founded the company that I really want to work with, and I'm gonna and I'm excited to like work with members of this team.
• 39:25
  SPEAKER_01: Um, and I'm gonna learn a shit ton, like right, I've never built a startup from zero to one.
• 39:29
  SPEAKER_01: That was something I really wanted to learn how to do.
• 39:31
  SPEAKER_01: Um but I knew that that mission leg was wobbly.
• 39:35
  SPEAKER_01: Um, and so it was just a way for me to visualize like sort of uh the choice I was making in going there.
• 39:41
  SPEAKER_01: And I think, you know, it's funny, I I don't know that I've used the stool as much since, but I do feel like everybody has a couple pillars that are important to them in the work that they do.
• 39:50
  SPEAKER_01: Um, and I do I also think the pillars are different for everyone and they change over time.
• 39:53
  SPEAKER_01: What is important to you, you know, when you're 20, when you're early 30s, when you have a family, if you have one, you know, um in your 40s, 50s, 60s, like that changes.
• 40:03
  SPEAKER_01: Um, and I think that's surprising.
• 40:05
  SPEAKER_01: Like you sort of think there should be things that are consistent throughout your career.
• 40:09
  SPEAKER_01: But um, one of the most interesting things for me is like what I cared about, what impact I cared about, the things I cared about, um, has like really changed or deepened uh as I got into my 40s.
• 40:21
  SPEAKER_01: And I think this was right, you know, when I was deciding like, do I want to be CEO, all these things, like right around when I turned 40.
• 40:27
  SPEAKER_01: Um, and it really uh made me stop and think about like what is the work that I want to do in this next chapter.
• 40:34
  SPEAKER_00: Yeah.
• 40:35
  SPEAKER_00: I find a lot of people when they're faced with these decisions, they are looking for certainty that they are going to enjoy something, yeah, or certainty that they're going to be good at it.
• 40:45
  SPEAKER_00: And I think that's the reason I asked if you would have known if you hadn't done it previously, is like sometimes you have to do the thing to learn if you're gonna be good or not at it.
• 40:54
  SPEAKER_00: And if you end up not being good at it, that's okay, like that is an okay outcome, and actually a great outcome because now you know that that's not your zone of genius or it's not something that you enjoy.
• 41:04
  SPEAKER_00: Absolutely.
• 41:05
  SPEAKER_00: And then that allows you to get even more specific moving forward in your career.
• 41:09
  SPEAKER_01: Yeah, and I have this really this thing that has worked really well for me, which is constantly trying new things and constantly pushing myself to take risks that seem a little crazy because I'm so curious about what it is that I am uniquely good at.
• 41:27
  SPEAKER_01: And in in that, in that process, right, you take on these jobs that are sort of batch it, like nobody should have offered them to you.
• 41:35
  SPEAKER_01: You actually do often discover, like, hey, nobody should ever hire me to do this.
• 41:38
  SPEAKER_01: You know, like at my last job at Facebook, I was a product manager, and it was like, oh, everybody wants to be a product manager, maybe I should do that too.
• 41:44
  SPEAKER_01: And then I was like six months and I was like, you know what?
• 41:46
  SPEAKER_01: I should never be a product manager.
• 41:48
  SPEAKER_01: And now you know.
• 41:49
  SPEAKER_01: No, totally.
• 41:50
  SPEAKER_01: And it's it's it's actually really powerful to know those things because then when somebody describes a job to you and says, Hey, do you want to come do this?
• 41:56
  SPEAKER_01: Like I remember somebody tried to hire me to be the head of their data team.
• 42:00
  SPEAKER_01: And I was like, sure, you'd be fine.
• 42:03
  SPEAKER_01: No, I I actually know exactly what I would have been.
• 42:05
  SPEAKER_01: And I said this to him, I was like, listen, let me tell you what I'd be great at.
• 42:08
  SPEAKER_01: I will come in and take over your data team.
• 42:10
  SPEAKER_01: I will figure out what the hell this team is for.
• 42:13
  SPEAKER_01: Um, I will figure out what the sort of point of it is and the leader that you need to hire, and I will hire you that leader.
• 42:19
  SPEAKER_01: But I am the worst person in the fucking world to run a data team long term.
• 42:24
  SPEAKER_01: Um, and I think you only get like I know myself really well at this point in my life, but only because I have tried and succeeded and failed at so many different things that I know, like, yep, not me.
• 42:36
  SPEAKER_00: You know?
• 42:37
  SPEAKER_00: Being able to set those expectations up front also creates a ton of trust with the person who's hiring you.
• 42:42
  SPEAKER_00: Absolutely.
• 42:43
  SPEAKER_00: Like I'm in a similar place now where I know the thing, like there are things in my current job that I said to Lovable when I took the role that I was like, this is not, this piece is not my strength, and I'm gonna need to bring someone in to help me with this.
• 42:55
  SPEAKER_00: Yeah, totally.
• 42:55
  SPEAKER_00: And the fact that you can say that up front gives the person who's bringing you in so much confidence that, like, oh, okay, like they're not gonna try to muddle through this thing that they're not great at.
• 43:05
  SPEAKER_00: And so I think going through that curiosity process and really doing the research on yourself over 10, 20, 30 years is like one of the most powerful things you can do in setting yourself up for success in roles.
• 43:16
  SPEAKER_01: Yeah, and I also think that, you know, you often, you know, early in your career, I think a lot of times you ha you feel like you should have a target, like a title or something like that.
• 43:24
  SPEAKER_01: And like one of the most interesting things I've watched, both with myself and with friends, is it's like, oh, I don't want to be CMO.
• 43:30
  SPEAKER_01: I just wanted to.
• 43:31
  SPEAKER_00: Mine was COO at a Series A company.
• 43:33
  SPEAKER_00: The brand work.
• 43:33
  SPEAKER_00: Yeah, I got that.
• 43:34
  SPEAKER_00: Totally.
• 43:35
  SPEAKER_00: I was not good at it.
• 43:36
  SPEAKER_01: No, and it's like, yeah, like I I think actually knowing who you are and who you're not is one of the most powerful tools you can have in a career.
• 43:43
  SPEAKER_01: Yeah.
• 43:44
  SPEAKER_01: Um, but to get there, you have to both like do a lot of trying, right?
• 43:49
  SPEAKER_01: And then also you have to acknowledge that it it does change over time.
• 43:52
  SPEAKER_01: Because what you're great at, you what you're great at doesn't change, but what you love doing does.
• 43:56
  SPEAKER_00: Yes, absolutely.
• 43:57
  SPEAKER_00: You also have to get comfortable with failing or Or being medium.
• 44:01
  SPEAKER_00: Like that's another thing for me that I've had to get comfortable with is like sometimes you get into things and you're just like, I'm just okay at this.
• 44:08
  SPEAKER_00: Like I'm not exceptional.
• 44:09
  SPEAKER_00: I'm not bad at it.
• 44:10
  SPEAKER_00: But like I should only I be should be trying to optimize for the work that I'm exceptional at.
• 44:15
  SPEAKER_00: Absolutely.
• 44:15
  SPEAKER_00: Absolutely.
• 44:16
  SPEAKER_00: Um, okay, let's talk about give away your Legos.
• 44:18
  SPEAKER_00: Are you bored of talking about this yet?
• 44:20
  SPEAKER_00: Or is it like you're never bored of this?
• 44:22
  SPEAKER_00: Okay, great.
• 44:23
  SPEAKER_00: Well, so I'm specifically curious about it, and I'll make sure to link the article for folks, but I'm curious about it in this era of like there's far less stability in corporate roles.
• 44:33
  SPEAKER_00: Like people are much less confident in their in their status and their like with all the layoffs happening and things like this.
• 44:40
  SPEAKER_00: So the advice to give away your Legos and constantly kind of be firing yourself from things and giving your work away to other people feels pretty counterintuitive in a in an era where we want to sort of prove how helpful we are and how much we can do and and that kind of thing.
• 44:54
  SPEAKER_00: Has this advice, have you found yourself shifting at all in this era, or do you do you are you still in the same camp?
• 45:01
  SPEAKER_01: I have so many thoughts about this, but I would just say that like one of the things that frustrates me the most right now about the way the conversation is happening around AI is that everything is fear.
• 45:12
  SPEAKER_01: And, you know, just to use one of your examples, like all these layoffs that are happening, like I'm got enough friends and enough folks that I work with that are in all these companies that you hear the backstory of the layoff.
• 45:25
  SPEAKER_01: And AI might be what they're saying, but it's not why they're laying people off.
• 45:28
  SPEAKER_01: Right.
• 45:29
  SPEAKER_01: Like that is not actually what is happening right now.
• 45:31
  SPEAKER_01: It may someday, but like honestly, you see companies telling stories about hiring more people because of AI versus laying people off.
• 45:38
  SPEAKER_01: So I'll just express some frustration and anger around like what we really need right now with AI is a stance of curiosity and a stance of play.
• 45:48
  SPEAKER_01: Like, and you're, I mean, I think Lovable's got such a great brand around play.
• 45:52
  SPEAKER_01: Um, because AI, I think, can be such a powerful tool in people's journey uh to build companies.
• 46:03
  SPEAKER_01: And and the reason why I'm I'm kind of passionate about this is that there is a huge amount of change going on, but suddenly there's all this opportunity that didn't exist before.
• 46:11
  SPEAKER_01: Like after I published the Legos article, which was in 2013, like I thought I was talking only to the Facebooks of the world, right?
• 46:17
  SPEAKER_01: Only to the hyperscale companies.
• 46:19
  SPEAKER_01: And I got a lot of feedback at the time that, like, no, this was applicable to like companies that were growing at any rate.
• 46:25
  SPEAKER_01: So the interesting thing that's happening is that now actually every single person in the world has the opportunity to give pieces of their job away to robots, right?
• 46:35
  SPEAKER_01: Like instead of it being about like, well, my company's either hiring or not hiring, right?
• 46:39
  SPEAKER_01: And so you can either give your Legos away or not.
• 46:41
  SPEAKER_01: Like I often got that question, which is like, what if their head counts flat?
• 46:44
  SPEAKER_01: Like, who do I give my Legos to?
• 46:46
  SPEAKER_01: Now I'm like, you can give them, you can take the boring ass pieces of your job that are repetitive and you can delegate them to these robots that are that are gonna hopefully you'll teach them to do it well.
• 46:57
  SPEAKER_01: Um, but I think that because there is so much fear in the conversation, that feels like, am I giving my job to this robot and then I'm gone.
• 47:09
  SPEAKER_01: And I I think no one fucking knows what's gonna happen in the next five to ten years with AI, but like I have this somewhat strongly held belief that ultimately there will be more opportunity because of all this technology.
• 47:25
  SPEAKER_01: Um, and to me, the most important thing to do is to learn how it fits into your life and your work and learn how to use it as a springboard and a trampoline.
• 47:35
  SPEAKER_01: And that is about giving away your Legos, but to the robots.
• 47:39
  SPEAKER_01: Um and you know, if you automate yourself out of a job, like I think, like, what is the next job, right?
• 47:45
  SPEAKER_01: You you've automated all of that, you have all these hours in the day.
• 47:47
  SPEAKER_01: Either A, go have a great time with your day, or B, like that gives you the opportunity and the time to like play around with something else, you know.
• 47:54
  SPEAKER_01: Um and I don't mean to sound like a daisy-eyed optimist because I know that it's like scary and hard out there, but that's always been part of growth and change.
• 48:03
  SPEAKER_01: Um, and actually, what's been really crazy for me is that I think suddenly the Legos article is actually like more applicable to more companies around the world because every company is going through such change.
• 48:15
  SPEAKER_01: And sometimes I think what the Legos article actually did for people was just say, like, don't worry, this is normal and it's gonna be okay.
• 48:22
  SPEAKER_01: And I feel like more people kind of need to hear that these days, which is like, you should play with this technology, you should figure out what it does for you.
• 48:30
  SPEAKER_01: Don't listen to the people on X or LinkedIn or whatever.
• 48:34
  SPEAKER_01: Go figure it out for yourself because most of them don't know what the fuck they're talking about.
• 48:37
  SPEAKER_01: And it matters that you develop a relationship with it and you figure out how it's useful to you.
• 48:43
  SPEAKER_01: And that comes from a place of curiosity and play.
• 48:45
  SPEAKER_01: Um, and and if you believe, like on the other side of it, there will be this opportunity, that's where the Legos thing comes in, right?
• 48:52
  SPEAKER_01: That you you learn how to give away parts of you know what you've become known for or gotten really good at, and then it actually expands opportunity for you because you have time and space to take on something else.
• 49:04
  SPEAKER_00: Yeah, I think sometimes the hardest thing is knowing what you're going to expand into.
• 49:07
  SPEAKER_00: I think people are looking for again that certainty of like, okay, well, if I give my Legos away, then I'm gonna spend my time doing that.
• 49:13
  SPEAKER_00: And sometimes you have to clear the space and be comfortable with that void a little bit in order to sort of discover how you're gonna fill it.
• 49:21
  SPEAKER_00: Yeah.
• 49:22
  SPEAKER_00: We always fill our time, like we figure out ways to fill our days, I think.
• 49:26
  SPEAKER_01: And I wrote an article on my Substack a couple of months ago because someone really reminded me that one of the things I didn't do well in the Legos article was talk about the fact that it's hard.
• 49:35
  SPEAKER_01: Yeah.
• 49:35
  SPEAKER_01: That it's scary and there's a lot of grief and that there's a lot of fear, and like all of that is true, and you should still do it.
• 49:42
  SPEAKER_00: Yeah, yeah, yeah.
• 49:44
  SPEAKER_00: Okay.
• 49:44
  SPEAKER_00: Last question.
• 49:45
  SPEAKER_00: What does good work mean to you?
• 49:48
  SPEAKER_00: What do you think good work is?
• 49:50
  SPEAKER_00: No, no, I'm not, I'm not the interviewee.
• 49:54
  SPEAKER_01: To me, I would just say that that's an incredibly individual decision and and and journey.
• 50:02
  SPEAKER_01: Um, I think what it meant to me in my 20s is not what it means to me now.
• 50:06
  SPEAKER_01: And um, you know, I I think I spent a lot of my early career trying to prove myself to someone, and and also I think I spent a lot of time sort of fighting to be remembered, like fighting to do work that was so important that you know.
• 50:24
  SPEAKER_01: Yeah, you'd leave some sort of legacy behind.
• 50:26
  SPEAKER_01: And it and it took realizing that like that's not a thing, like that no one's gonna remember you, and that like, you know, you might you might impact people's lives for a minute, and that can be meaningful, but it it makes you really ask, like, what's the work that's meaningful to me?
• 50:41
  SPEAKER_01: What is the impact that I want to have today and in this hour and in this week?
• 50:46
  SPEAKER_01: Um, what's the thing that's gonna feed me on this journey, right?
• 50:49
  SPEAKER_01: Like, the journey is the point, not the destination.
• 50:52
  SPEAKER_01: And I'm spoken like someone that you know is in the middle of their life versus early on, but I think that takes time to learn and also means that like the work, the best work is the work that feeds you.
• 51:07
  SPEAKER_01: Because somebody um somebody just said to me, like, I can't remember the quote, but like, if the world was full of more alive people, the world would be better off.
• 51:16
  SPEAKER_01: So, like, what's the work that makes you come alive is actually the question.
• 51:20
  SPEAKER_01: Not like impact or you know, legacy or any of that.
• 51:24
  SPEAKER_01: It's just like, what do you want to fill your days with?
• 51:26
  SPEAKER_00: I love that.
• 51:27
  SPEAKER_00: That's so great.
• 51:27
  SPEAKER_00: Also, the journey is long.
• 51:29
  SPEAKER_00: Journey is fucking long, man.
• 51:30
  SPEAKER_00: Yeah.
• 51:30
  SPEAKER_01: So long.
• 51:31
  SPEAKER_01: No, a friend of mine came to Glue Club and said that.
• 51:33
  SPEAKER_01: He was like, careers are long, and it's really easy to forget that.
• 51:36
  SPEAKER_01: Yeah, particularly when you're having a dark moment, you know, you think this is the whole book.
• 51:41
  SPEAKER_01: And I, it's like what I always say is like, it feels like the whole book, it's usually just a chapter.
• 51:45
  SPEAKER_00: Yeah.
• 51:45
  SPEAKER_00: Amazing.
• 51:46
  SPEAKER_00: Well, thank you so much for being here.
• 51:48
  SPEAKER_00: Yeah.
• 51:48
  SPEAKER_00: This was awesome.
• 51:49
  SPEAKER_00: Thank you for having me.
• 51:50
  SPEAKER_00: So good.
• 51:50
  SPEAKER_00: This has been good work with Molly Graham.
• 51:53
  SPEAKER_00: And uh I think that's it.
• 51:56
  SPEAKER_00: Thanks.