Latest / "the good work talk show" with mallory contois / the good work talk show | ep. 07 - emily kramer

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the good work talk show | ep. 07 - emily kramer · "the good work talk show" with mallory contois

• 0:00
  SPEAKER_00: Can we go back to when you were a kid?
• 0:02
  SPEAKER_00: I Sure.
• 0:03
  SPEAKER_00: Really?
• 0:04
  SPEAKER_00: I was not an entrepreneur at five.
• 0:06
  SPEAKER_00: My advice to other people is like go narrower.
• 0:08
  SPEAKER_00: Whether you're starting advising or starting a newsletter is like have a niche.
• 0:12
  SPEAKER_00: Because it needs to be when someone thinks of something, they think of you.
• 0:16
  SPEAKER_00: People are always like, oh, I need to stay the full four years to vest all my options.
• 0:19
  SPEAKER_00: Like, actually, no.
• 0:20
  SPEAKER_00: How do you calculate risk?
• 0:21
  SPEAKER_00: I don't know, like what seems risky to other people's seams risky to be.
• 0:25
  SPEAKER_01: Today on Good Work, my guest is Emily Kramer.
• 0:28
  SPEAKER_01: She is an absolutely legendary marketing leader who created early marketing teams at Asana, at Carta, at Astro, and now she writes an incredible newsletter called Market One with over 80,000 readers.
• 0:39
  SPEAKER_01: I am extremely excited to talk to her today about her decision to move away from operating into teaching and writing and creating.
• 0:47
  SPEAKER_01: Very curious what that transition has been like for her.
• 0:50
  SPEAKER_01: I want to ask her about the reality of building a newsletter business.
• 0:54
  SPEAKER_01: I'm excited to ask her about how embracing change and taking debts on herself have influenced her career.
• 1:00
  SPEAKER_01: If you've thought about starting a newsletter, if you've thought about expanding into new revenue streams or a portfolio career, I think you're really gonna enjoy this conversation.
• 1:12
  SPEAKER_01: I'm Mallory Contois, and this is good work.
• 1:17
  SPEAKER_01: Somebody's gonna fall into a pool one of these days.
• 1:19
  SPEAKER_01: I hope so.
• 1:21
  SPEAKER_01: Okay, Emily Kramer, welcome to Good Work.
• 1:23
  SPEAKER_01: Thanks for having me.
• 1:24
  SPEAKER_01: Thank you for being here.
• 1:25
  SPEAKER_01: Poolside.
• 1:25
  SPEAKER_01: Poolside.
• 1:26
  SPEAKER_01: Can't see the pool.
• 1:27
  SPEAKER_01: Can't see the pool, but trust me.
• 1:28
  SPEAKER_01: But I'm looking at one.
• 1:29
  SPEAKER_01: It's here.
• 1:30
  SPEAKER_01: Um okay.
• 1:32
  SPEAKER_01: A helpful place to start for the audience, I think, is um tell us about like a a week.
• 1:38
  SPEAKER_01: So, like, what did you do in the past week?
• 1:40
  SPEAKER_01: What does a week in your work life look like?
• 1:42
  SPEAKER_01: And not an average week, because I know that's impossible.
• 1:44
  SPEAKER_01: But we're not gonna take last week.
• 1:45
  SPEAKER_01: Last week I was under the weather.
• 1:48
  SPEAKER_01: There's a lot of coughing.
• 1:49
  SPEAKER_00: Yeah, which happens to me.
• 1:51
  SPEAKER_00: Um a typical week, it like highly depends if it's like a newsletter week or a not newsletter week.
• 1:56
  SPEAKER_00: Yeah.
• 1:57
  SPEAKER_00: Because I do them twice a month.
• 1:59
  SPEAKER_00: And so if it's a newsletter week, it's like I'm really I'm uh need a deadline to get things done, but I'm like an 11th hour person, so it's a lot of like stress and swirl, and like I'm gonna get to get this out, and then sometimes I don't, and like, you know, it's it's like a different week.
• 2:14
  SPEAKER_00: It's very focused on like getting this big thing moral.
• 2:17
  SPEAKER_00: And then yeah, and I try to like not have other things going on.
• 2:20
  SPEAKER_00: Of course, other things pop up.
• 2:22
  SPEAKER_00: Yeah.
• 2:22
  SPEAKER_00: So I like advise a number of people and I have to respond to them or have some meetings, but for the most part, like dialed in on that.
• 2:28
  SPEAKER_00: And then the other weeks are a little chiller, and I like do everything else that's everything else.
• 2:35
  SPEAKER_00: I don't know.
• 2:36
  SPEAKER_00: I catch up on like usually I'm like working on something new or doing some sort of like project related to everything I do, or like right now I'm building out a lot of like clawed code skills for our MCP server, and so like working on that stuff, or I don't know, like whatever it might be.
• 2:51
  SPEAKER_00: There's always something there, like working on a podcast last year is the case, or um, just whatever other project I have in the works, or just like you know, writing a bunch of sponsor copy and getting that done, or like writing a bunch of LinkedIn posts that I have to do and like getting those teed up.
• 3:04
  SPEAKER_00: I do more of that in theory than in practice.
• 3:08
  SPEAKER_00: I have like 25 LinkedIn posts teed up.
• 3:10
  SPEAKER_00: No, I don't.
• 3:12
  SPEAKER_00: I'm kind of adjusting time person, but in my mind I'm doing that.
• 3:14
  SPEAKER_00: And yeah, I also try to like concentrate meetings into certain days.
• 3:18
  SPEAKER_00: So I try to concentrate my meetings on Tuesdays, like for advising, it doesn't always work that way.
• 3:23
  SPEAKER_00: Yeah.
• 3:23
  SPEAKER_01: And have like um later in the week to be very like open, but as far as work goes for you, your uh revenue streams, like what are you what are your revenue streams right now?
• 3:35
  SPEAKER_01: Just in case you sound like my accountant.
• 3:37
  SPEAKER_00: Well, you know, we're getting straight to the money here.
• 3:40
  SPEAKER_00: Um yeah, my revenue stream.
• 3:43
  SPEAKER_00: Nobody's ever asked me that this way, except for maybe my accountant, and he's like, how do we classify these things?
• 3:48
  SPEAKER_00: Um real QuickBooks codes.
• 3:49
  SPEAKER_00: My yeah, my revenue streams are um I my newsletter on Substack has paid subscribers, so that's one revenue stream.
• 3:58
  SPEAKER_00: I also have sponsors for my newsletter, so three sponsors, uh a newsletter, so that's another revenue stream.
• 4:04
  SPEAKER_00: Yep.
• 4:05
  SPEAKER_00: Um I also do some sponsored posts on LinkedIn, but always for companies that I love and actually use, of course.
• 4:11
  SPEAKER_00: But actually, but actually well vetted.
• 4:14
  SPEAKER_00: Um, so that's another one.
• 4:15
  SPEAKER_00: Um, so just like sponsorships.
• 4:17
  SPEAKER_00: Also do like events and things like that that often have sponsors as well.
• 4:20
  SPEAKER_00: So I guess I should just say like I went to one of your dinners recently.
• 4:23
  SPEAKER_00: It was delightful.
• 4:24
  SPEAKER_00: Revenue is what I should say, but sponsorships.
• 4:26
  SPEAKER_00: Um, and I kind of try to concentrate those to a few companies as well.
• 4:30
  SPEAKER_00: I work really closely with Profound, I love their products, I work really closely with Framer, I love their products.
• 4:34
  SPEAKER_00: I won't name any competitors to granola, I am a granola user.
• 4:38
  SPEAKER_00: Um, but I have you know some bigger partnerships as well.
• 4:41
  SPEAKER_00: And then I um what else do we do?
• 4:43
  SPEAKER_00: Oh, I advise.
• 4:44
  SPEAKER_00: Yep.
• 4:45
  SPEAKER_00: And I have invested in a bunch of companies as well.
• 4:48
  SPEAKER_00: That's less of a revenue stream and more of a maybe someday you'll get like a chunk at a time.
• 4:51
  SPEAKER_00: Yes.
• 4:51
  SPEAKER_00: Um we'll we'll get to the fund.
• 4:53
  SPEAKER_00: And then I've taught some courses on Maven.
• 4:55
  SPEAKER_00: Um that's an occasional revenue stream, so I'll add some things in.
• 4:59
  SPEAKER_00: But I think that's true portfolio career.
• 5:01
  SPEAKER_00: I think that's it.
• 5:02
  SPEAKER_00: Yeah.
• 5:03
  SPEAKER_01: Yeah, there's probably one more floating around.
• 5:05
  SPEAKER_00: Yeah, I'll do like a workshop here and there kind of thing with a company, and we're gonna do more of those with like getting marketing teams comfortable with AI.
• 5:11
  SPEAKER_00: But yes, truly like a bunch of revenue streams.
• 5:14
  SPEAKER_00: Um, yeah, that's kind of, I think by design, advising's really lumpy.
• 5:18
  SPEAKER_00: Yeah, so when I was just advising, I felt that.
• 5:22
  SPEAKER_00: And so having like that newsletter that's pretty consistent and predict predictable is really useful, and like it's not as like predictable as ARR, but like it kind of is.
• 5:30
  SPEAKER_00: Yeah, kind of recurs.
• 5:32
  SPEAKER_00: It's a literal subscription, yeah.
• 5:33
  SPEAKER_00: Well, the subscriptions actually recur, and then the sponsors, like I just know that I'm gonna have this.
• 5:39
  SPEAKER_00: If I write this many newsletters, I'll have this many sponsors.
• 5:41
  SPEAKER_00: So it's pretty predictable now.
• 5:42
  SPEAKER_01: Okay, so now that we're grounded in kind of how you're spending your time now.
• 5:44
  SPEAKER_01: In my reality, in your reality, we're grounded in our reality right now.
• 5:49
  SPEAKER_01: Can we go back to when you were a kid?
• 5:51
  SPEAKER_01: I sure really not to therapy you.
• 5:54
  SPEAKER_00: Were my revenue streams when I was five?
• 5:56
  SPEAKER_00: I didn't have any revenue stuff.
• 5:57
  SPEAKER_00: Were you thinking about revenue streams?
• 5:59
  SPEAKER_00: I I was not an entrepreneur at five.
• 6:00
  SPEAKER_01: Okay, this is sort of where I'm going.
• 6:02
  SPEAKER_01: I'm curious what you were like as a kid.
• 6:04
  SPEAKER_01: Like, what were I feel like we all when we look back at ourselves as kids or we listen to the stories people told us about ourselves?
• 6:10
  SPEAKER_01: Like, what were your inclinations?
• 6:12
  SPEAKER_01: Like, what did you like doing?
• 6:13
  SPEAKER_01: What were you like?
• 6:14
  SPEAKER_01: What kind of like environment did you grow up in?
• 6:16
  SPEAKER_01: Anything that feels relevant.
• 6:18
  SPEAKER_00: Yeah, well, I was mostly like a math kid, which I really liked math.
• 6:22
  SPEAKER_00: Yeah.
• 6:22
  SPEAKER_00: So as like a young kid, I would like do math in the corner.
• 6:25
  SPEAKER_00: Did you do like math leads and stuff?
• 6:26
  SPEAKER_00: Not like that.
• 6:27
  SPEAKER_00: More like even like I went to I went to a Montessori kindergarten and I was just like doing like multiplication in the corner.
• 6:33
  SPEAKER_00: Because it was fun.
• 6:34
  SPEAKER_00: Because it was fun.
• 6:35
  SPEAKER_00: Um so it's very much like very mathy, which is funny now because I like write as my job, but I still think of myself as more mathy than writing.
• 6:42
  SPEAKER_00: Um, and so that was very much like what I was good at in school.
• 6:47
  SPEAKER_00: And then I don't know, I was like a pretty like well-rounded kid, otherwise, did a lot of like played like every sport, did like every activity, um, moved around a lot, went to a bunch of schools, went to five elementary schools, moved in the middle of elementary school, moved again in the middle of high school.
• 7:02
  SPEAKER_00: So a lot of like change, meeting new people.
• 7:04
  SPEAKER_00: So I think I kind of got pretty adaptable in many situations and like was able to like how did you do in those in those changes as a kid?
• 7:11
  SPEAKER_00: Um, I was always like really scared about it, but it usually worked out.
• 7:14
  SPEAKER_00: Like I didn't end up friendless in any situation.
• 7:16
  SPEAKER_00: And sometimes in certain situations, people were like excited to have someone new come in.
• 7:20
  SPEAKER_00: And so that was uh I felt really welcomed when I moved in the middle of high school, with which a lot of people probably don't.
• 7:25
  SPEAKER_00: And so in the end, I kind of got like two groups of friends, and I was really angry at my parents about it for a really long time, but it probably was for the best.
• 7:32
  SPEAKER_00: So yeah, moved around a lot, was it was you know, did well in school, played basketball for a while.
• 7:38
  SPEAKER_00: Nothing really that remarkable.
• 7:39
  SPEAKER_00: Yeah.
• 7:40
  SPEAKER_01: Do you feel like moving that much like adapted you to risk a little bit earlier on or like getting comfortable and ambiguously?
• 7:47
  SPEAKER_00: I'm like not afraid of change, actually, to the point where I think I like love change and I love to keep things different, and I can't like just stay in one lane or do one thing.
• 7:54
  SPEAKER_00: And I'm also like, you know, I can like make friends as an adult and like those things where like you know, a lot of people are stuck in like their high school or their college friend group, like that's not me at all.
• 8:03
  SPEAKER_00: And it comes from comes from going to all the schools and being in all those situations.
• 8:07
  SPEAKER_00: So, in some ways, like don't recommend it for children, but in other ways, like it was great.
• 8:12
  SPEAKER_00: Yeah, it really depends on the case.
• 8:13
  SPEAKER_00: I also went to summer camp my whole life, and that was a whole huge part of my childhood, and it's actually remained somewhat a part of my adulthood.
• 8:18
  SPEAKER_00: Um I went to summer camp, yeah, to New Hampshire.
• 8:21
  SPEAKER_00: So I went to summer camp from the time I was 11.
• 8:24
  SPEAKER_00: Um, and then I worked there through early college and went like all summer, starting as like a young teen.
• 8:29
  SPEAKER_00: Um, and so because I moved around a lot, those were like consistent friends.
• 8:32
  SPEAKER_00: And then my I when I started working at Asana, I got my Asana job um as head of marketing at Asana, not through like some grand connection or like a VC or whatever it was.
• 8:44
  SPEAKER_00: I got it from one of my campers who was a recruiting coordinator at the time.
• 8:47
  SPEAKER_00: So Kelsey introed me into Asana, and that's how that happened.
• 8:50
  SPEAKER_00: And then she eventually moved to my team, um, moved on to the marketing team from recruiting.
• 8:55
  SPEAKER_00: So like my camper was now my direct report, which is just you never know where those connections are gonna come from.
• 9:00
  SPEAKER_00: But it came from camp.
• 9:01
  SPEAKER_00: Um, and now I yeah, I spend summers on the lake where I went to camp now.
• 9:04
  SPEAKER_00: So uh I I my friends still run it and I like you know spend some time there and yeah, so like can't like very much like a camp person.
• 9:12
  SPEAKER_00: What was it about camp that you feel like you were drawn to or why why?
• 9:16
  SPEAKER_00: I think just like the independence and like I don't know, it was on an island on a lake, felt cool, like it's it had a very like independence feel, and and I didn't I didn't have any other like consistency, yeah.
• 9:28
  SPEAKER_00: And I loved being outside and loved being on the water and like doing water sports and all that stuff.
• 9:31
  SPEAKER_00: So it was just kind of campy out here.
• 9:34
  SPEAKER_00: Yeah, I mean there's water, it was like we're camped.
• 9:36
  SPEAKER_00: No, I just like loved being in the water and swimming and like sailing, and I like windsurfed and water skied and the whole nine.
• 9:42
  SPEAKER_00: Like I loved it, it was great.
• 9:43
  SPEAKER_00: Yeah, yeah.
• 9:43
  SPEAKER_00: And it was like the same people always, and the same people still run it, so it's just like very consistent.
• 9:48
  SPEAKER_00: So yeah, I just loved it, and I loved like being able to go do my thing and kind of have this like secret life every summer.
• 9:53
  SPEAKER_01: Yeah, okay, cool.
• 9:54
  SPEAKER_01: Yeah, and then you went to college.
• 9:56
  SPEAKER_01: I did, and you double majored, is my research right?
• 10:00
  SPEAKER_00: Yeah, I double majored.
• 10:01
  SPEAKER_00: I went to two colleges.
• 10:02
  SPEAKER_00: I went to Boston University my freshman year.
• 10:04
  SPEAKER_00: Okay.
• 10:05
  SPEAKER_00: I wanted to go to Tufts, which is like a liberal arts school in Boston.
• 10:08
  SPEAKER_00: I didn't get in, and I went to BU and um I didn't like it, it was huge.
• 10:15
  SPEAKER_00: Um, and I transferred to Tufts the next year.
• 10:18
  SPEAKER_00: Okay.
• 10:19
  SPEAKER_00: Which wasn't always the plan.
• 10:20
  SPEAKER_00: Like I wasn't like, oh, I'll go here and I'll transfer, but that's what happened.
• 10:22
  SPEAKER_00: And so I went to two colleges.
• 10:24
  SPEAKER_00: Um just you know, continuing the trend that I was mad at my parents for.
• 10:28
  SPEAKER_00: I was like, oh, now I'll choose to go to two.
• 10:30
  SPEAKER_00: So I went to two high schools and two colleges, and you know.
• 10:33
  SPEAKER_00: Uh but anyway, uh, yeah, I double majored in art history and economics.
• 10:37
  SPEAKER_00: I think originally when I went to BU, I think I declared a double major in math and econ, which like I am not that mathy.
• 10:43
  SPEAKER_00: Yeah, that's that was intense.
• 10:45
  SPEAKER_00: I was not, I'm not actually that mathy.
• 10:47
  SPEAKER_00: And so my mom's an artist, she's a stained glass artist.
• 10:50
  SPEAKER_00: So I've always like been around art and creativity and all of that stuff.
• 10:55
  SPEAKER_00: My dad's a software engineer, like an OG software engineer.
• 10:58
  SPEAKER_01: You and I grew up in a similar dynamic where my mom um is very artistic and was always in the arts, photography, and painting, and thinking my dad's a doctor.
• 11:06
  SPEAKER_00: So like very much the like a similar arts and the science.
• 11:10
  SPEAKER_00: Yeah, for sure.
• 11:11
  SPEAKER_00: There definitely is like a opposites thing going on there.
• 11:13
  SPEAKER_00: And so I have both, I've always felt like creative, but also very mathy, but more emphasis on the math as a kid, and I think more emphasis on the creativity as I've gotten older.
• 11:21
  SPEAKER_00: Yeah.
• 11:22
  SPEAKER_00: But um, yeah, I was a double major.
• 11:23
  SPEAKER_00: I don't really know why.
• 11:24
  SPEAKER_00: It's a weird combination, art history and economics, but that's just what I did.
• 11:28
  SPEAKER_00: I think I like um I'm very I'm a very competitive person, maybe that's obvious, and a very like driven and sort of focused person.
• 11:35
  SPEAKER_00: And so I like to like have a lane and then like do the lanes.
• 11:38
  SPEAKER_00: So for me, rather than taking like a million courses, it was like have two lanes.
• 11:42
  SPEAKER_00: Two very clear, distinct, uh, yeah, like not messy lanes.
• 11:45
  SPEAKER_00: Like they were very separate from each other.
• 11:47
  SPEAKER_00: Right.
• 11:48
  SPEAKER_00: And like just rather than like, you know, taking a bunch of classes or whatever, I just kind of like took those classes.
• 11:53
  SPEAKER_00: Yeah.
• 11:53
  SPEAKER_01: I also worked at a video store in college, which is a fun fact.
• 11:55
  SPEAKER_01: No, we were just talking about video stores yesterday.
• 11:58
  SPEAKER_01: We because Blockbuster came up.
• 11:59
  SPEAKER_01: Okay.
• 12:00
  SPEAKER_00: I worked at Hollywood Video, a competitor.
• 12:02
  SPEAKER_00: It was just the one that was closest to college.
• 12:03
  SPEAKER_00: But I worked there one summer when I was just like living on campus, and then I stayed working there through the year.
• 12:08
  SPEAKER_00: Um, and I worked like a lot.
• 12:09
  SPEAKER_00: I just like I liked working there, and I was one of those people that like didn't really, you know, study that much.
• 12:15
  SPEAKER_00: And so I just worked a lot at the video store, and it was the end of an era.
• 12:19
  SPEAKER_00: Like it was the last time, probably in college, people can say I worked in a video store, and people still came in.
• 12:24
  SPEAKER_00: Um, and there was like repeat customers, and we talk about movies, and it was awesome.
• 12:28
  SPEAKER_01: Do you feel like there was anything when you were kid through college that was like, oh, you're probably gonna be an entrepreneur one day?
• 12:34
  SPEAKER_00: Like, did you my dad is an entrepreneur?
• 12:36
  SPEAKER_00: So my dad had started a number of software companies, a couple with his brother.
• 12:40
  SPEAKER_00: I moved to Florida when I was eight, and that was because his friend had started a company down there and he was going to like help him out.
• 12:45
  SPEAKER_00: And so my dad was like in that world.
• 12:47
  SPEAKER_00: I didn't really understand what my dad did.
• 12:49
  SPEAKER_00: I obviously like didn't really ask the questions, but like I probably didn't realize exactly what he did until I went to college or maybe even later.
• 12:55
  SPEAKER_00: And then, you know, you kind of realize that that's just part of you or whatever.
• 13:00
  SPEAKER_00: But yeah, so my dad, my dad started a number of companies, and so I guess it just was a you know, I think you got normalized.
• 13:08
  SPEAKER_00: It was a normalized thing, and I think I've always been, you know, the type A sort of like leader in a group, so it and and wanting to go my own path and don't love authority.
• 13:18
  SPEAKER_00: So it all makes sense.
• 13:20
  SPEAKER_00: I can I can relate, you know?
• 13:21
  SPEAKER_01: Totally.
• 13:22
  SPEAKER_01: Okay, so um we get out of college, we get into being like adults, um still still working on that.
• 13:28
  SPEAKER_01: Still working on that, both of us.
• 13:29
  SPEAKER_01: Um, but in those first years, you got into like media and and ads and things like that.
• 13:34
  SPEAKER_00: Yeah, I worked at the ad agency.
• 13:36
  SPEAKER_00: I mean, I just moved to San Francisco without a job.
• 13:37
  SPEAKER_00: Everyone was moving to New York, just wanted to like do something different.
• 13:41
  SPEAKER_00: Is that can we um pause on that?
• 13:43
  SPEAKER_01: Why did you move to San Francisco without like what walk me through that decision compared to I'm sure your all your peers were going with a job?
• 13:52
  SPEAKER_00: Yeah, um, not necessarily with a job, but just to New York.
• 13:56
  SPEAKER_00: Sure.
• 13:56
  SPEAKER_00: And I don't know, I was just trying to like figure out what I wanted to do.
• 13:59
  SPEAKER_00: I was like interviewing at some jobs out in San Francisco.
• 14:03
  SPEAKER_00: You had grown up on the East Coast, yeah, in Florida and New Jersey and Pennsylvania and then in New England in the summer.
• 14:08
  SPEAKER_00: Um, and so like the whole, the whole East Coast, um, very different parts of it.
• 14:12
  SPEAKER_00: But I had like been to California like once, and I don't know, I guess I just said like seen TV shows that I like kind of in San Francisco.
• 14:20
  SPEAKER_00: I don't know, I just like kind of wanted to live in San Francisco, kind of wanted to do something different.
• 14:23
  SPEAKER_00: Yeah.
• 14:23
  SPEAKER_00: Um, I moved a lot as a kid, so I wasn't afraid to like move and be somewhere else.
• 14:27
  SPEAKER_00: So I was like, oh, I'll apply to some jobs here and apply to some jobs in New York.
• 14:31
  SPEAKER_00: I like interviewed at a couple of record labels in New York.
• 14:33
  SPEAKER_00: That's what I wanted to do.
• 14:34
  SPEAKER_00: It was like work in music, and then I found out that you made like like you couldn't live in New York on what you make as an assistant at a record label.
• 14:40
  SPEAKER_00: Yeah.
• 14:40
  SPEAKER_00: So I like kind of changed course a little bit.
• 14:43
  SPEAKER_00: And um, my friend had a spot in his apartment, my friend from college.
• 14:46
  SPEAKER_00: It was like, come live here until you don't, you know, until you don't find something, find something, whatever.
• 14:51
  SPEAKER_00: So I lived there for a few months and then found another place.
• 14:53
  SPEAKER_00: But all that's to say is like it was 2006, it's a while ago now, 20 years ago.
• 14:57
  SPEAKER_00: It was much easier to just like find something, I feel like.
• 14:59
  SPEAKER_00: Sure.
• 15:00
  SPEAKER_00: And rent and stuff in San Francisco was a lot cheaper.
• 15:02
  SPEAKER_00: So it was like more.
• 15:03
  SPEAKER_00: I think about that now.
• 15:04
  SPEAKER_00: It's so much harder to take those risks in cities.
• 15:06
  SPEAKER_01: Yeah.
• 15:06
  SPEAKER_00: I think in like any major city, honestly, but especially the Bay, New York, LA.
• 15:10
  SPEAKER_00: Right.
• 15:10
  SPEAKER_00: Um, so yeah, I just and then I just was interviewing for a bunch of jobs, and I got this job at an advertising agency, um, doing like media planning and buying, which is what you would think of as like growth marketing essentially.
• 15:21
  SPEAKER_00: Yeah.
• 15:21
  SPEAKER_00: Um, for like all sorts of Microsoft um, you know, things.
• 15:27
  SPEAKER_00: Microsoft says a ton of things.
• 15:28
  SPEAKER_00: Yeah.
• 15:28
  SPEAKER_00: And so then I eventually ended up working on Zune, which is what I wanted to work on, which was their like MP3 player, the competitors.
• 15:34
  SPEAKER_00: C-U-N-E.
• 15:35
  SPEAKER_00: Yeah, it's a competitor to an iPod.
• 15:37
  SPEAKER_00: Yeah.
• 15:37
  SPEAKER_00: Or was.
• 15:38
  SPEAKER_00: And it was actually kind of ahead of its time.
• 15:40
  SPEAKER_00: Like you could like peer-to-peer share songs.
• 15:42
  SPEAKER_00: Like it was cool.
• 15:45
  SPEAKER_00: I don't know.
• 15:46
  SPEAKER_00: So, but we also do some really cool things.
• 15:48
  SPEAKER_00: So I was like buying ad spots in like um magazines and online and like billboards and radio and cinema.
• 15:55
  SPEAKER_00: So it was really cool.
• 15:56
  SPEAKER_00: We had huge budgets, all these music publications and stuff like that.
• 15:59
  SPEAKER_00: So it's great because I love live music and love that world.
• 16:02
  SPEAKER_00: And so um, yeah, that's what I did.
• 16:04
  SPEAKER_00: And then I went to business school for some unknown reason.
• 16:06
  SPEAKER_00: I was gonna ask you about your decision to go to business school.
• 16:09
  SPEAKER_00: I don't know.
• 16:10
  SPEAKER_00: You don't know.
• 16:10
  SPEAKER_00: Um no, I mean I do know, right?
• 16:12
  SPEAKER_00: Like you grow up for me.
• 16:13
  SPEAKER_00: I grew up in an environment where you know everyone goes to college and almost everyone that I went to college with goes to grad school.
• 16:21
  SPEAKER_00: It's just kind of like that world.
• 16:23
  SPEAKER_00: Yep.
• 16:23
  SPEAKER_00: And you got into Harvard.
• 16:26
  SPEAKER_00: And I got into Harvard, and that felt like you go if you get in.
• 16:29
  SPEAKER_00: Yep.
• 16:30
  SPEAKER_00: Actually, I applied to a number of places.
• 16:31
  SPEAKER_00: I actually didn't apply to any to Berkeley or Stanford, even though I was out here.
• 16:35
  SPEAKER_00: I thought I wanted to go back to the East Coast, and I thought it would be like a way to do that in some ways.
• 16:39
  SPEAKER_00: I applied to like seven schools.
• 16:40
  SPEAKER_00: I did not get into most of them, but got into Harvard and said, okay, I guess I'll go.
• 16:44
  SPEAKER_00: And then I actually thought about leaving after the first year.
• 16:47
  SPEAKER_00: Um, because I just really didn't like it.
• 16:49
  SPEAKER_00: Yeah.
• 16:50
  SPEAKER_00: Um what didn't you like about it?
• 16:51
  SPEAKER_00: It was like a monoculture.
• 16:53
  SPEAKER_00: A lot of the people that I met from business school are much more interesting now, like now that they're in their own world, like years later.
• 16:58
  SPEAKER_00: But there's just something about I'm very type A.
• 17:00
  SPEAKER_00: I don't necessarily like to be around everyone else that's like that.
• 17:04
  SPEAKER_01: Um is a lot of high achieving people in the world.
• 17:06
  SPEAKER_00: Yeah, yeah, and just like a lot of people that were, if not a lot of creativity in the way that I like it either.
• 17:11
  SPEAKER_00: Like it just wasn't, you know, I felt like very I went in 2009 and the 2008 like um crash, financial crash happened.
• 17:20
  SPEAKER_00: So it was a lot of like disgruntled i bankers in my class who were like, we'll ride it out.
• 17:23
  SPEAKER_00: Famously the most fun year out.
• 17:25
  SPEAKER_00: Yeah, I don't think people think about things like that.
• 17:26
  SPEAKER_00: Like when you go to college or when you go to business school or when you go to grad school or when you start working can play such a like massive role.
• 17:33
  SPEAKER_00: Yeah.
• 17:33
  SPEAKER_00: Like literally, what year can play such a massive role in your experience?
• 17:37
  SPEAKER_00: How things shake out.
• 17:38
  SPEAKER_00: I mean, I guess maybe that's obvious, but maybe it's not.
• 17:40
  SPEAKER_00: I don't know.
• 17:41
  SPEAKER_01: I think when you look at people's arcs, it's hard to we don't always do the work to like contextualize them.
• 17:46
  SPEAKER_01: So I think it's helpful to add that.
• 17:48
  SPEAKER_00: Like graduating college now would be so different than graduating college in 2006.
• 17:52
  SPEAKER_00: It'd be like, oh my god, my career's what is my career gonna be?
• 17:55
  SPEAKER_00: What is a career?
• 17:55
  SPEAKER_00: What is career?
• 17:56
  SPEAKER_00: Which is what is what we're doing here, really.
• 17:58
  SPEAKER_00: What am I doing?
• 17:59
  SPEAKER_00: And you know, that didn't didn't feel that way.
• 18:01
  SPEAKER_01: I've heard you mention a couple of times things along the lines of like I wanted to do something different.
• 18:05
  SPEAKER_01: I like having creative people around.
• 18:07
  SPEAKER_01: Like, do you feel like you have a desire to mix things up or to do things differently from other people?
• 18:14
  SPEAKER_01: Like, is that part of your psyche?
• 18:16
  SPEAKER_01: Yeah, yeah.
• 18:17
  SPEAKER_01: Do you know where that comes from?
• 18:18
  SPEAKER_01: This is like therapy.
• 18:20
  SPEAKER_01: It's yeah.
• 18:21
  SPEAKER_01: Welcome.
• 18:22
  SPEAKER_00: Like, is that a problem?
• 18:23
  SPEAKER_01: You can l yeah.
• 18:24
  SPEAKER_01: I mean, listen, all voluntary.
• 18:26
  SPEAKER_00: Um, no, I don't feel I don't feel violated.
• 18:29
  SPEAKER_00: Do you feel trapped?
• 18:29
  SPEAKER_00: No, I don't feel trapped or violated.
• 18:31
  SPEAKER_00: I'm comfortable with therapy.
• 18:32
  SPEAKER_00: I just like, does anybody care?
• 18:34
  SPEAKER_00: Yeah, they care.
• 18:35
  SPEAKER_00: Okay, so what was the question?
• 18:37
  SPEAKER_00: How am I feeling right now?
• 18:38
  SPEAKER_00: Um great.
• 18:39
  SPEAKER_01: Are you relaxed, chill?
• 18:40
  SPEAKER_01: No, um, I was asking you where that comes from, your desire to sort of do things differently from other people, or um, like is it just an instinct?
• 18:49
  SPEAKER_00: Natural born renegade.
• 18:51
  SPEAKER_00: Yeah, I mean, maybe.
• 18:52
  SPEAKER_00: No, I don't, I I don't know.
• 18:54
  SPEAKER_00: Maybe it is because I was like always like a I don't know how much of it has to do with like always being sort of like a new kid, so like purposely then standing out almost like I don't know.
• 19:04
  SPEAKER_00: Maybe it's just like my mother is like very outgoing and like kind of on our own.
• 19:09
  SPEAKER_00: Yeah, I don't I I don't know, but I've always I've always kind of been that way.
• 19:12
  SPEAKER_01: Yeah, okay, cool.
• 19:12
  SPEAKER_00: Like wanting to fit in just enough.
• 19:14
  SPEAKER_00: Right, but but not totally.
• 19:15
  SPEAKER_01: Yeah, right, right, right.
• 19:17
  SPEAKER_01: Okay.
• 19:17
  SPEAKER_00: And so when you get out of I mean, we could probably really psychoanalyze that, and I certainly have with all of the moving, but we'll stop there.
• 19:23
  SPEAKER_01: That's for the episode two.
• 19:25
  SPEAKER_01: That's yeah, that's for free outtakes.
• 19:27
  SPEAKER_01: Like I start bawling.
• 19:28
  SPEAKER_01: That's a director's cut.
• 19:30
  SPEAKER_01: Jump into the pool.
• 19:31
  SPEAKER_01: Um okay, so we leave business school, and now you are.
• 19:35
  SPEAKER_01: Do you go directly to Asana after?
• 19:37
  SPEAKER_00: No, I went to a company called Ticketfly, which um that's right, ultimately got acquired by Pandora and then Eventbrite, but it was like a Ticketmaster competitor.
• 19:45
  SPEAKER_00: Okay.
• 19:45
  SPEAKER_00: Actually founded by people who had sold another company to Ticketmaster.
• 19:47
  SPEAKER_01: So we're still in the music, like, yeah, I love my music.
• 19:50
  SPEAKER_00: I can't play music at all.
• 19:51
  SPEAKER_00: I'm like not musical at all, but I just like love going.
• 19:53
  SPEAKER_00: I've always I worked at a radio station and a record label in college, in addition to the video store in the summer.
• 19:59
  SPEAKER_00: Um, so like always just wanted to be in music and entertainment.
• 20:04
  SPEAKER_00: Um, and then didn't want to do that anymore, really.
• 20:07
  SPEAKER_01: Well, I was gonna say the the left turn to Asana.
• 20:10
  SPEAKER_00: Yeah, it's not exactly giving creative industry.
• 20:12
  SPEAKER_00: No, it's definitely well, people that started Asana might argue differently.
• 20:16
  SPEAKER_00: It's enabling anybody.
• 20:17
  SPEAKER_00: Right.
• 20:18
  SPEAKER_00: Um but uh Were you ready for a change?
• 20:22
  SPEAKER_00: I well so took it fly as like a proper tech company, like standard like VCs and building a platform for you know venues and promoters to use, just like kind of a very different audience than selling into other tech companies.
• 20:32
  SPEAKER_00: Yeah.
• 20:33
  SPEAKER_00: Like send selling into like, you know, thousand-person standing room only, like music venues across the country.
• 20:38
  SPEAKER_00: Pretty different audience than like other than Asana's audience.
• 20:41
  SPEAKER_00: Some crossover.
• 20:42
  SPEAKER_00: Some some, sure.
• 20:43
  SPEAKER_00: But um, it just seemed like a really good opportunity to Asana.
• 20:46
  SPEAKER_00: Like, I mean, Asana was started by Facebook co-founders.
• 20:48
  SPEAKER_00: Uh, we were using the product actually at Tickfly.
• 20:50
  SPEAKER_00: I could kind of see it starting to take off.
• 20:52
  SPEAKER_00: I would be the 35th employee, and it just seemed like and like be building on marketing just seemed like a great opportunity.
• 20:58
  SPEAKER_00: So it wasn't like now it's time to go completely B2B.
• 21:00
  SPEAKER_00: Yeah.
• 21:01
  SPEAKER_00: Like that wasn't none, it wasn't really planned.
• 21:03
  SPEAKER_00: It was a good opportunity.
• 21:05
  SPEAKER_01: Did it feel, did you like the pivot to a different industry?
• 21:08
  SPEAKER_01: Like, was that or did you find yourself missing like consumer?
• 21:12
  SPEAKER_00: Um I mean, there's definitely been a lot of moments in my career where I'm like, wow, maybe I should have just stayed in the because that was like more, you know, it was two, it was two-sided at Ticketfly.
• 21:20
  SPEAKER_00: We we helped some venue sell tickets when we were selling to the venues, but it felt it felt uh both consumer and B2B.
• 21:27
  SPEAKER_00: Um there's definitely been times where I wish I'd just like stayed in consumer.
• 21:31
  SPEAKER_00: Because that Asana really kicked off your the whole rest of your career.
• 21:37
  SPEAKER_00: I mean a lot of like PLG stuff, but yeah, I I it was not on purpose.
• 21:41
  SPEAKER_00: If I could go back in time, you can't you can't be like, oh, I would change this because like I'm you know doing interesting things now.
• 21:47
  SPEAKER_00: But uh yeah, I accidentally stumbled into B2B.
• 21:50
  SPEAKER_00: Like that was not the plan.
• 21:51
  SPEAKER_00: Like B2B Tech wasn't the plan.
• 21:53
  SPEAKER_01: If you ask Claude, it summarized you as one of the most prolific B2B first marketers of all time.
• 21:58
  SPEAKER_01: So you've really
• 22:03
  SPEAKER_00: Yeah.
• 22:03
  SPEAKER_00: I mean, I I was the first or second, like first-ish B2B marketer four times.
• 22:09
  SPEAKER_00: Yeah.
• 22:10
  SPEAKER_00: Um including Tickfly, which was mostly B2B.
• 22:13
  SPEAKER_00: Right.
• 22:13
  SPEAKER_00: Um, but yeah, I it was not on purpose.
• 22:15
  SPEAKER_00: Yeah.
• 22:16
  SPEAKER_01: Okay.
• 22:16
  SPEAKER_01: And well, a lot of things aren't.
• 22:18
  SPEAKER_01: Um, okay, so I'm really curious about your decision to leave Asana and go to Astro.
• 22:23
  SPEAKER_00: Yeah.
• 22:23
  SPEAKER_01: Because there, you know, Asana was going great, presumably.
• 22:26
  SPEAKER_00: I've been in Asana for almost four years.
• 22:28
  SPEAKER_00: They gave you a six-week sabbatical at three years, which was amazing.
• 22:31
  SPEAKER_00: Wow.
• 22:31
  SPEAKER_00: Asana had like, everyone had a really long tenure.
• 22:34
  SPEAKER_00: Some of the people I hired were there for like eight years.
• 22:36
  SPEAKER_00: Yeah.
• 22:36
  SPEAKER_00: Number of people.
• 22:37
  SPEAKER_00: Which is really long.
• 22:38
  SPEAKER_00: People are still there for the time that from the time I was there and I left like almost 10 years ago.
• 22:43
  SPEAKER_00: I'm still very close with the group of Asana Marketing, the Asana marketing team who I hired.
• 22:48
  SPEAKER_00: They're all like my very close friends.
• 22:49
  SPEAKER_00: Yeah.
• 22:50
  SPEAKER_00: Um, I just was ready for something different.
• 22:52
  SPEAKER_00: I think you the company had grown really fast.
• 22:55
  SPEAKER_00: I was leading marketing.
• 22:56
  SPEAKER_00: I I think I like thought that I might get layered.
• 22:59
  SPEAKER_00: It wasn't like said that I was gonna be layered, but I kind of saw the company scaling.
• 23:02
  SPEAKER_00: I've never done this before.
• 23:04
  SPEAKER_00: Like, what's gonna happen here?
• 23:05
  SPEAKER_00: Like leadership changes.
• 23:06
  SPEAKER_00: Just felt like it's time to just like do something else.
• 23:08
  SPEAKER_00: Yeah.
• 23:09
  SPEAKER_00: And I really thought I wanted to start a company at that point, but I was too afraid.
• 23:12
  SPEAKER_00: And so I was like, oh, I'll go to like this.
• 23:14
  SPEAKER_00: Was a lot of the decisions I made.
• 23:16
  SPEAKER_00: Like business school, I was like, maybe I'll start a company.
• 23:18
  SPEAKER_00: This is a good path.
• 23:18
  SPEAKER_00: Like, that is not a good path if you want to start a company.
• 23:21
  SPEAKER_00: Sure.
• 23:21
  SPEAKER_00: Unless you go into business school with the idea and like take that time and those.
• 23:24
  SPEAKER_01: So you thought maybe I want to start a company as early as like when you went to business school school.
• 23:28
  SPEAKER_01: When I went into business, yes, for sure.
• 23:29
  SPEAKER_01: And so you were kind of navigating the best path.
• 23:31
  SPEAKER_00: And then and then I was like, oh, I'll go to a really early stage startup and like lead marketing and like support and some other like opsy things.
• 23:38
  SPEAKER_01: Did that decision feel scary to you at the time, leaving Asana?
• 23:42
  SPEAKER_01: Or were was it pretty?
• 23:43
  SPEAKER_00: It felt sad because like it was.
• 23:45
  SPEAKER_00: I mean, Asana had like a great culture.
• 23:47
  SPEAKER_00: Like we had like meal.
• 23:49
  SPEAKER_00: You were comfortable and happy.
• 23:50
  SPEAKER_00: They were like my friends, and they still are, yeah, many years on.
• 23:52
  SPEAKER_00: Those are like my really close friends.
• 23:54
  SPEAKER_00: Um and so it felt sad in that way, but it felt like it was time to do something different.
• 23:59
  SPEAKER_00: Okay.
• 24:00
  SPEAKER_00: Um and and you chose a very so you chose this small company, like and it was also in collaboration.
• 24:05
  SPEAKER_00: So it was actually like it was AI for email.
• 24:07
  SPEAKER_00: So I was trying to do like, I don't know, fixer, like super fixer is like an AI product for email now.
• 24:13
  SPEAKER_00: People use like superhuman.
• 24:14
  SPEAKER_00: It was, but it was way too early.
• 24:16
  SPEAKER_00: Yeah.
• 24:16
  SPEAKER_00: Um, and I got acquired by Slack before their series B, but I helped them raise their series A.
• 24:20
  SPEAKER_00: I was in the fundraising conversations, like that was really interesting.
• 24:23
  SPEAKER_00: I met like a lot of great investors through that process.
• 24:25
  SPEAKER_00: I met like Aileen Lee through that process and like a bunch of interesting people that I still keep in touch with.
• 24:30
  SPEAKER_00: And so being that early like got me involved in those in those things.
• 24:35
  SPEAKER_00: And so that's kind of why I did it.
• 24:37
  SPEAKER_00: Okay.
• 24:37
  SPEAKER_00: And they were repeat founders.
• 24:39
  SPEAKER_01: Right.
• 24:40
  SPEAKER_01: So it's in you were you were sort of you had enough confidence in the bet that you were making.
• 24:44
  SPEAKER_00: They were repeat founders like in the email space.
• 24:46
  SPEAKER_00: So they knew how to navigate.
• 24:48
  SPEAKER_00: And we were like a little too early for what we were doing, but you know, built a bunch on with Slack, and that's eventually what they who they got acquired by.
• 24:55
  SPEAKER_00: And you were there for about two years.
• 24:57
  SPEAKER_00: Two years.
• 24:58
  SPEAKER_00: And then we went to Carta.
• 24:59
  SPEAKER_00: And then I went to Carta.
• 25:00
  SPEAKER_00: Yes.
• 25:01
  SPEAKER_00: Which was, yeah.
• 25:02
  SPEAKER_00: And how big was Carta when you joined?
• 25:03
  SPEAKER_00: Um, it was like 300 people.
• 25:05
  SPEAKER_00: Okay.
• 25:05
  SPEAKER_00: It was big, big for me, but they didn't have any marketing.
• 25:07
  SPEAKER_00: So they had a number of false starts.
• 25:09
  SPEAKER_00: They had like one person sort of doing like some demand gen stuff, but I think reporting into sales, they had like no marketing ops.
• 25:15
  SPEAKER_00: They had a couple of rev ops, people they just hired, and they had a bunch of people on the sales team.
• 25:20
  SPEAKER_00: Like okay.
• 25:21
  SPEAKER_00: So it was a very sell sales-led.
• 25:23
  SPEAKER_00: And yes, there was just nothing, they had just changed their name from eShares to Carta.
• 25:27
  SPEAKER_00: There had been no like real marketing around.
• 25:28
  SPEAKER_00: Oh, I forgot about eShares.
• 25:29
  SPEAKER_00: So there's a lot of like brand confusion, and I liked building marketing teams.
• 25:32
  SPEAKER_00: I'd done it three times, and so I was like, oh, this will be great.
• 25:35
  SPEAKER_00: Best of both worlds.
• 25:36
  SPEAKER_00: Like all of this money, not all of this, but like, you know, they have revenue.
• 25:40
  SPEAKER_00: Yep.
• 25:41
  SPEAKER_00: They have um funding.
• 25:43
  SPEAKER_00: Yeah.
• 25:44
  SPEAKER_00: And like I can build a marketing team, but like kind of at scale.
• 25:46
  SPEAKER_00: So I grew that team really fast um to like 25 people in just a little over a year.
• 25:53
  SPEAKER_00: Um, as the company grew really, really fast when I was there.
• 25:56
  SPEAKER_00: Um and yeah, just a different setting for building out, building out marketing.
• 26:01
  SPEAKER_00: Yep.
• 26:01
  SPEAKER_00: Um, and like very B2B.
• 26:03
  SPEAKER_00: So that was like the most sales-led thing I'd done by like far.
• 26:06
  SPEAKER_01: Yeah.
• 26:06
  SPEAKER_01: Um when we were zooming out this much, it feels very fast.
• 26:09
  SPEAKER_01: Like it's like, oh, I went to this company and then I went to this company and this company.
• 26:13
  SPEAKER_01: Uh uh, the reality is there were like you were there for four years, two.
• 26:17
  SPEAKER_00: I was at Astro for almost two, I was at Carta for almost two.
• 26:20
  SPEAKER_00: Yeah, okay.
• 26:21
  SPEAKER_00: And so how much like I wouldn't look at my resume and say that's a job bouncer, but some people might.
• 26:26
  SPEAKER_01: No, I'm curious more about whether it felt like you were taking risks by moving, or if you were taking these bets, or if it felt like, oh, my time, like I've I've sort of done my time and now I'm moving on.
• 26:38
  SPEAKER_00: I like I like I like change.
• 26:40
  SPEAKER_00: And so I I don't like things to stay the same.
• 26:42
  SPEAKER_00: Like you we talked about the revenue streams.
• 26:44
  SPEAKER_00: I like to have a bunch of things going on.
• 26:46
  SPEAKER_00: I get bored easily, I like seek it out.
• 26:49
  SPEAKER_00: Um, I'm married to someone who's like exactly the opposite, yeah, hates change.
• 26:53
  SPEAKER_00: Um, and like switching jobs feels like this Herculean thing, which is totally valid.
• 26:58
  SPEAKER_00: Yeah.
• 26:59
  SPEAKER_00: Um, but for me and and her parents like had the same job for 30 years, so it makes sense.
• 27:04
  SPEAKER_00: And my dad had a million jobs when I was a kid.
• 27:06
  SPEAKER_00: So it just felt I I kind of also feel like if you're getting equity in startups, and now that I've been like a VC as well and an investor, people are always like, Oh, I need to stay the full four years to vest all my options.
• 27:16
  SPEAKER_00: Like, actually, no, like you it's so much can happen, so much can change.
• 27:21
  SPEAKER_00: You can have so much money on paper, and I've had that happen too, where a company's been valued at a ton of money and now it's not, and who knows what's happening with it.
• 27:28
  SPEAKER_00: And actually having portf or equity in a bunch of companies and having sort of a portfolio for yourself is actually better.
• 27:37
  SPEAKER_00: And so I kind of started to see it that way, and I also just started to see like, well, if I'm not like learning or finding this interesting anymore, like just move on.
• 27:46
  SPEAKER_01: Yeah.
• 27:46
  SPEAKER_01: And so we know your relationship to change.
• 27:49
  SPEAKER_01: What is your relationship to risk?
• 27:50
  SPEAKER_01: Like, how do you think about those things?
• 27:52
  SPEAKER_01: Like, how do you calculate risk?
• 27:54
  SPEAKER_01: How do you think about like I don't know, like that?
• 27:57
  SPEAKER_00: What seems risky to other people seems risky to me.
• 27:59
  SPEAKER_01: Okay.
• 28:00
  SPEAKER_01: Do you acknowledge that other people would think that things that you have done are risky?
• 28:05
  SPEAKER_00: Recently.
• 28:05
  SPEAKER_00: More recently.
• 28:06
  SPEAKER_01: You mean you acknowledge that recently for their whole career or only the things that you've recently done?
• 28:12
  SPEAKER_00: No, meaning like I never thought about any of it as really that risky until I filed a lawsuit, and that was definitely risky.
• 28:18
  unknown: Sure.
• 28:19
  SPEAKER_01: And yeah, until I And then did that just bring risk into a higher profile for you and maybe gave you a little bit more like attention to it?
• 28:27
  SPEAKER_01: Or like what changed when you did that with your relationship to risk?
• 28:31
  SPEAKER_00: Did it make you more risk averse?
• 28:33
  SPEAKER_00: No, not at all.
• 28:34
  SPEAKER_00: No, no, not at all.
• 28:35
  SPEAKER_00: I guess it just made people were like, whoa, what a risk.
• 28:38
  SPEAKER_00: Like people literally, oh, you're so brave.
• 28:40
  SPEAKER_00: And I'm like, really?
• 28:41
  SPEAKER_00: I just I just have to do this.
• 28:42
  SPEAKER_00: Yeah.
• 28:43
  SPEAKER_00: This this was not right, what occurred.
• 28:45
  SPEAKER_00: Like this was unlawful.
• 28:46
  SPEAKER_00: Like, I have to file this lawsuit.
• 28:47
  SPEAKER_00: I have no other choice.
• 28:48
  SPEAKER_00: Yeah.
• 28:49
  SPEAKER_00: And so I think, uh, yeah, but people are like, you know, again, what a risk taker.
• 28:54
  SPEAKER_00: And then you're like, oh, maybe I am.
• 28:56
  SPEAKER_01: Yeah.
• 28:56
  SPEAKER_01: So risk isn't actually the highest thing that you're thinking about.
• 28:59
  SPEAKER_01: It's it's all the other things.
• 29:01
  SPEAKER_01: Let's live life, like, let's be risky, not really.
• 29:03
  SPEAKER_00: You're not risk for the sake of risk.
• 29:04
  SPEAKER_01: No.
• 29:05
  SPEAKER_01: But it you find yourself in situations in which sometimes.
• 29:07
  SPEAKER_00: But I guess I live a risky life.
• 29:09
  SPEAKER_00: I don't know.
• 29:10
  SPEAKER_01: Okay.
• 29:11
  SPEAKER_00: Therapy again.
• 29:12
  SPEAKER_01: Yes, therapy again.
• 29:13
  SPEAKER_01: I apologize.
• 29:14
  SPEAKER_00: No, it's all good.
• 29:15
  SPEAKER_00: All right.
• 29:15
  SPEAKER_00: So I mean, you can tell who the adrenaline junkies are because we all have a lot of tattoos.
• 29:20
  SPEAKER_01: You have them too.
• 29:21
  SPEAKER_01: You're right.
• 29:22
  SPEAKER_01: Do you like adrenaline?
• 29:23
  SPEAKER_01: You're not wrong.
• 29:23
  SPEAKER_01: So it's funny, I actually don't, I'm not like a jump off a cliff adrenaline person.
• 29:28
  SPEAKER_01: Okay.
• 29:29
  SPEAKER_01: But I do like to like fucking feel something.
• 29:31
  SPEAKER_01: Yeah.
• 29:31
  SPEAKER_01: Yeah.
• 29:32
  SPEAKER_01: So I do think that like entrepreneurship, I think um, again, I very much resonate with a lot of what you're saying, which is like things that seem risky to other people just seem interesting to me.
• 29:43
  SPEAKER_01: Right.
• 29:43
  SPEAKER_00: Like I don't think of them as risky.
• 29:45
  SPEAKER_01: I'm gonna learn something, but so much of that is also our privilege and having like amazing networks and communities and support systems and like like we are able to privilege in this whole system.
• 29:54
  SPEAKER_01: We're able to be so much riskier than so many people, which I'm so so grateful for.
• 29:58
  SPEAKER_01: But um, I totally we're very similar in that way.
• 30:01
  SPEAKER_00: Yeah.
• 30:01
  SPEAKER_00: And there's so much like luck and all of these things that allows you to be able to take some of these risks.
• 30:05
  SPEAKER_01: Yeah.
• 30:06
  SPEAKER_01: And I want to move on to the, and I'm so sorry.
• 30:09
  SPEAKER_01: Is it um I don't think you ever resolved this for me at the dinner we were at?
• 30:12
  SPEAKER_01: Is it MKT1 or Marketing One?
• 30:15
  SPEAKER_01: It's Market One.
• 30:16
  SPEAKER_01: Market One.
• 30:17
  SPEAKER_01: Maybe.
• 30:18
  SPEAKER_01: All right, we'll go with Market One for the name.
• 30:20
  SPEAKER_00: No, it's a it's a name.
• 30:21
  SPEAKER_00: It's a name.
• 30:22
  SPEAKER_00: It's not, it was like a working title for me and my old business partner when we were advising.
• 30:26
  SPEAKER_00: It wasn't intended to be a newsletter.
• 30:27
  SPEAKER_00: It was like, it was supposed to stand for like marketing one.
• 30:32
  SPEAKER_00: We didn't know how to say it.
• 30:33
  SPEAKER_00: And then everyone else called it market one, so it's market one now.
• 30:35
  SPEAKER_00: Cool.
• 30:36
  SPEAKER_00: Um who needs vowels?
• 30:38
  SPEAKER_00: Market no one.
• 30:39
  SPEAKER_00: There's a no, you do need vowels.
• 30:41
  SPEAKER_00: It was very much a COVID name.
• 30:42
  SPEAKER_00: I started going places after COVID and had to say it out loud.
• 30:44
  SPEAKER_00: Like we I started advising companies in 2020.
• 30:47
  SPEAKER_00: And people are like, what?
• 30:49
  SPEAKER_00: MKT Byrne?
• 30:51
  SPEAKER_01: Okay, so I want to talk about that, but before we get there, I want to talk a tiny bit about the work that you did at Carta, which led up to that lawsuit, which is the the um equity inequality step.
• 31:02
  SPEAKER_01: Was that something that you so you were leading marketing there at the time?
• 31:05
  SPEAKER_01: Was that a was that your idea to do that type of work?
• 31:09
  SPEAKER_00: No, we had a bunch of data at CARDA.
• 31:11
  SPEAKER_00: So um, you know, a bunch of just and they're still doing this today.
• 31:15
  SPEAKER_00: They're publishing a lot of like data in aggregate about the state of startups, and and we had a bunch of data, and it was actually like a group of um women angel investors who came to the CEO of Carta and said, Hey, can we do this study with you?
• 31:26
  SPEAKER_00: We've been trying to access this data on the gap in equity, like the salary gap between um between genders.
• 31:33
  SPEAKER_00: Yeah.
• 31:34
  SPEAKER_00: Um, and what what data did you have?
• 31:36
  SPEAKER_00: Can we do this?
• 31:37
  SPEAKER_00: And um I kind of said, Oh, I'll run with this.
• 31:41
  SPEAKER_01: Did that feel did that feel like a bet or a risk?
• 31:44
  SPEAKER_00: Yeah, no, that it seemed like a good opportunity.
• 31:46
  SPEAKER_00: Like we're trying to put ourselves on the map.
• 31:47
  SPEAKER_00: We hadn't gotten a lot of press.
• 31:48
  SPEAKER_00: Like this, it was a very calculated bet.
• 31:50
  SPEAKER_00: Like, yeah, we hadn't gotten a lot of press in the past because we didn't have marketing.
• 31:53
  SPEAKER_00: Yeah, we changed our name.
• 31:55
  SPEAKER_00: We wanted to show size and scale, and you can do that really well when you have all this data.
• 31:59
  SPEAKER_00: And it seemed like a good cause, like explaining how equity works and also explaining the differences in in who gets what.
• 32:07
  SPEAKER_00: And so I felt really like like it was an important thing, and also was good marketing.
• 32:12
  SPEAKER_00: Yeah.
• 32:13
  SPEAKER_00: Um, so it was a good thing to do, was great marketing.
• 32:16
  SPEAKER_00: Rarely do those things come together where you can like put something out that makes people kind of think differently about compensation and all of that, and have it be also great for the company.
• 32:25
  SPEAKER_00: And so it's just a good opportunity in that way.
• 32:28
  SPEAKER_00: And then it was my decision to like make that a bigger thing the next year and do more of these, do another study.
• 32:33
  SPEAKER_00: So we did two studies.
• 32:35
  SPEAKER_00: I it was in a bunch of publications.
• 32:37
  SPEAKER_00: Um, and yeah, just highlighted there's a huge gap in equity, like there is in salary, not surprise, not surprisingly.
• 32:42
  SPEAKER_00: Yeah, yeah, yeah.
• 32:43
  SPEAKER_01: Now let's talk about your decision to start your own thing.
• 32:46
  SPEAKER_01: Yeah, for sure.
• 32:47
  SPEAKER_01: Tell me where you were at mentally and like what the first pieces of it were.
• 32:54
  SPEAKER_01: Like, what were the first kind of actions you took?
• 32:56
  SPEAKER_00: How did you come up with the idea?
• 32:57
  SPEAKER_00: I don't think I ever decided to do my own thing, it just sort of happened.
• 33:01
  SPEAKER_00: So I left Carta, I filed a lawsuit that was fairly public, that went on for a number of years and was then resolved a few weeks before trial.
• 33:12
  SPEAKER_00: Um, and so I had that going on.
• 33:15
  SPEAKER_00: I also had um pretty soon into, I guess a year into leaving Carta, I was diagnosed with lymphoma as well.
• 33:24
  SPEAKER_00: And so I had um major health issue and was gonna need chemo and immunotherapy for six months and this lawsuit.
• 33:32
  SPEAKER_00: And so I couldn't really like.
• 33:34
  SPEAKER_00: What year are we in right now?
• 33:36
  SPEAKER_00: What year?
• 33:36
  SPEAKER_00: 1975.
• 33:38
  SPEAKER_00: No, uh, we're in 2021.
• 33:40
  SPEAKER_00: 2020, 2021.
• 33:42
  SPEAKER_00: Um, so it's like COVID.
• 33:43
  SPEAKER_01: This is around when you and I met.
• 33:44
  SPEAKER_00: Yeah, yeah.
• 33:45
  SPEAKER_00: It was COVID.
• 33:46
  SPEAKER_00: I was doing like, yeah, Angel Track stuff.
• 33:48
  SPEAKER_00: Yep.
• 33:48
  SPEAKER_00: We met through Angel Track, first round Angel Track.
• 33:50
  SPEAKER_00: Yeah.
• 33:50
  SPEAKER_00: So I was doing um so I originally was like, I'm gonna take some time off.
• 33:55
  SPEAKER_00: This carto experience led me to need to take some time off.
• 33:57
  SPEAKER_00: And I have this lawsuit.
• 33:59
  SPEAKER_00: I don't know how long this is gonna be or what this is gonna require of me, but like I'm gonna just advise companies for a while in marketing, built four marketing teams, let's figure out what's next.
• 34:07
  SPEAKER_00: So I started doing that with my friend Kathleen, who co-founded Market One with me.
• 34:10
  SPEAKER_00: That's when we had this like working title for our advising group to like make an LLC, and that's where it came from.
• 34:16
  SPEAKER_00: And we just started advising companies together, and things just kind of went from there.
• 34:20
  SPEAKER_00: And then literally six months later is when I found out I had cancer.
• 34:24
  SPEAKER_00: Um, and so I couldn't really get another job at that time.
• 34:28
  SPEAKER_00: Yeah.
• 34:29
  SPEAKER_00: Um, originally, actually, when I left Carta, I thought I was gonna start like a venture back company.
• 34:33
  SPEAKER_00: I was working with a friend of mine on some ideas.
• 34:34
  SPEAKER_00: Some of them were compensation related, some of them weren't.
• 34:37
  SPEAKER_00: And we were working through like a number of them, nothing felt quite right.
• 34:41
  SPEAKER_00: And then the fun came much later.
• 34:43
  SPEAKER_00: And the newsletter was I don't know.
• 34:45
  SPEAKER_00: I think the newsletter maybe started a year after I started advising, maybe like nine months.
• 34:50
  SPEAKER_00: Very casually.
• 34:51
  SPEAKER_00: I was sick of talking to sick of saying the same thing all the time.
• 34:54
  SPEAKER_00: Yeah.
• 34:54
  SPEAKER_00: Especially I was working with a lot of early stage founders.
• 34:57
  SPEAKER_00: Or to directly to people.
• 34:58
  SPEAKER_00: Direct talking to founders.
• 34:59
  SPEAKER_00: I was working with a lot of early stage founders, so it was like, who's your first marketing hire?
• 35:02
  SPEAKER_00: Or like, how do you organize this team?
• 35:04
  SPEAKER_00: Or like basic things.
• 35:05
  SPEAKER_00: Almost like your FAQs.
• 35:07
  SPEAKER_00: Yeah.
• 35:07
  SPEAKER_00: And so that's what it was at first.
• 35:08
  SPEAKER_00: It was just like, what are the FAQs?
• 35:10
  SPEAKER_00: And so the first one was about org charts, and it did really well.
• 35:12
  SPEAKER_00: Yeah.
• 35:13
  SPEAKER_00: Um, still does really well.
• 35:14
  SPEAKER_00: Substack?
• 35:15
  SPEAKER_00: I started on Substack.
• 35:16
  SPEAKER_00: Yeah, so you've always been on Substack.
• 35:17
  SPEAKER_00: And and it was like ear I wouldn't say it's like early days in Substack, but like most platforms, there's a time to start where you can grow a lot faster.
• 35:24
  SPEAKER_00: Like if you try to grow on LinkedIn now, it's so much harder, or Substack.
• 35:28
  SPEAKER_00: Yep.
• 35:28
  SPEAKER_00: I started on LinkedIn a little late.
• 35:30
  SPEAKER_00: I started on Substack, I think exactly at the right time.
• 35:32
  SPEAKER_00: Yeah.
• 35:32
  SPEAKER_00: Um, and so yeah, I just started writing very sporadically.
• 35:36
  SPEAKER_00: It was like quarterly, then it was like twice a month.
• 35:38
  SPEAKER_00: It was just very So it wasn't like, hey, I'm gonna build a newsletter business.
• 35:41
  SPEAKER_00: It was a No, I didn't even know what that really looked like.
• 35:44
  SPEAKER_00: Yeah.
• 35:45
  SPEAKER_00: And so I yeah, it was just like, oh, I'm gonna I'm advising, I'm gonna do this, I'm gonna write.
• 35:48
  SPEAKER_00: I and we didn't have paid subscribers or sponsors for a very long time.
• 35:52
  SPEAKER_00: It was just a way to get advising clients.
• 35:54
  SPEAKER_00: I thought of it as like lead gen, like a funnel.
• 35:56
  SPEAKER_00: Like content marketing.
• 35:57
  SPEAKER_00: Yeah.
• 35:58
  SPEAKER_00: Yeah.
• 35:58
  SPEAKER_00: And so I thought of it that way.
• 35:59
  SPEAKER_00: It wasn't I didn't think of it as a revenue stream for a long time.
• 36:02
  SPEAKER_00: But then it just kind of like happened.
• 36:03
  SPEAKER_00: So again, none of this was like very planned at all.
• 36:05
  SPEAKER_00: Yeah.
• 36:05
  SPEAKER_01: And how much of you deciding to be a good thing?
• 36:07
  SPEAKER_01: Which is probably an annoying thing to say when people are like, no, that's a real success and it wasn't planned.
• 36:11
  SPEAKER_01: But like, no, but I think what it shows is an int a like willingness to follow the follow the pull of certain things.
• 36:18
  SPEAKER_01: Like when certain things start to kind of feel like they have momentum or there's like positive.
• 36:23
  SPEAKER_01: Like I imagine that you just you saw the other newsletters starting to kind of take off.
• 36:27
  SPEAKER_00: Because this was like I knew Lenny through Angel Chalk as well, and I saw his newsletter taking off.
• 36:33
  SPEAKER_00: I mean, his is at a big pretty big scale already.
• 36:34
  SPEAKER_00: But starting like 22, 2023 were like when a lot of those big newsletters started to grow.
• 36:39
  SPEAKER_00: Oh yeah, it was about that time.
• 36:40
  SPEAKER_00: Yeah.
• 36:41
  SPEAKER_00: So you had examples.
• 36:42
  SPEAKER_00: And it was going, people liked it, so I just like kept going.
• 36:44
  SPEAKER_00: And then I was like, let's do this on a cadence.
• 36:46
  SPEAKER_00: And then I don't remember if I think we turned on paid subscribers before we turned on sponsors, but I actually don't know.
• 36:51
  SPEAKER_01: Yeah.
• 36:51
  SPEAKER_01: Do you remember ever feeling any sort of way about the idea of being a creator?
• 36:56
  SPEAKER_01: Do you currently feel any type of way about being a creator?
• 37:00
  SPEAKER_00: Um less so now.
• 37:01
  SPEAKER_00: Yeah.
• 37:02
  SPEAKER_00: But like there are moments, it's more so like out in tech, it's fine.
• 37:05
  SPEAKER_00: It's like, sure, oh, I'm a creator, or like a joking, like, oh, I'm like a, you know, I'm like, is that how you if somebody asks to what you do?
• 37:11
  SPEAKER_00: No, I say like have a substack or like write a newsletter.
• 37:14
  SPEAKER_00: Yeah.
• 37:14
  SPEAKER_00: It's it's this is this is gonna sound pretentious, so maybe we're gonna have to cut this out, or maybe we're gonna delete it in.
• 37:19
  SPEAKER_00: It's the same kind of thing when people are like, Did you go to grad school?
• 37:22
  SPEAKER_00: And you're like, oh in Boston.
• 37:24
  SPEAKER_00: Yeah, if you say like in Boston, then people are gonna be like, Did you go to Harvard?
• 37:28
  SPEAKER_00: And you're like, Yes, and you sound like a douchebag.
• 37:30
  SPEAKER_00: And then if you say, Oh, I went to Harvard Business School, like right out the gate, they're gonna you sound there's just really Yeah, sure.
• 37:35
  SPEAKER_01: You're like, oh but so so do you ever umbrella it or bucket it into something like, oh, I'm a creator or I'm I or do you do you stay very like I'm gonna be.
• 37:45
  SPEAKER_01: I usually just say like I have a newsletter and I advise companies.
• 37:47
  SPEAKER_00: It depends on who I'm talking to, right?
• 37:49
  SPEAKER_00: Yeah, but it's funny, like outside of tech, like my partner doesn't work in tech at all, and nor do a lot of her friends or even some of my friends are uh like when I'm in New Hampshire in the summer and I'm like talking to like you know, someone random from New Hampshire.
• 38:04
  SPEAKER_00: And they have they don't even understand what I mean when I say like startup.
• 38:07
  SPEAKER_00: Or like newsletter.
• 38:08
  SPEAKER_00: Do they get newsletter?
• 38:09
  SPEAKER_00: I mean, but they're like, what?
• 38:12
  SPEAKER_00: I'm like, I have a Substack, like are my brother and sister-in-law that work in this world, and they're like, You have a newsletter, what?
• 38:17
  SPEAKER_00: Like, they've never looked at it, I don't think.
• 38:19
  SPEAKER_00: That's very funny.
• 38:20
  SPEAKER_00: So I don't know.
• 38:21
  SPEAKER_00: I guess I just a nice balance to like get away from the tech industry for a minute.
• 38:24
  SPEAKER_00: Yeah, yeah.
• 38:25
  SPEAKER_00: Is it one of the reasons you do it?
• 38:26
  SPEAKER_00: I like really need to be, it's like a great thing that I'm like not married to someone that works in tech.
• 38:31
  SPEAKER_00: I think for some people that works really well, and people start companies together in the wife is in MRI tech?
• 38:36
  SPEAKER_00: She is ultrasound, the scenography.
• 38:39
  SPEAKER_00: Okay.
• 38:39
  SPEAKER_00: Um just totally different.
• 38:42
  SPEAKER_00: It's actually funny, she's doing some like AI data labeling for an ultrasound tech company right now that like is married, it's like a connection that I had.
• 38:50
  SPEAKER_00: So she's like contributing to the future of her demise.
• 38:53
  SPEAKER_01: Oh no, tough.
• 38:55
  SPEAKER_01: Um, okay, so if somebody, a lot of folks that are watching this probably aspire to maybe some portion of your work or like some version of what you do.
• 39:04
  SPEAKER_01: Is there what are what would you say that they should be doing right now if if this is something they're interested in doing?
• 39:11
  SPEAKER_00: Yeah.
• 39:12
  SPEAKER_00: I think it's harder than it looks.
• 39:15
  SPEAKER_00: Yes.
• 39:15
  SPEAKER_00: I think most things might be harder than it looks like.
• 39:17
  SPEAKER_00: I think that is actually a universal truth that most things are harder than they look.
• 39:20
  SPEAKER_00: Um, I think it seems like everyone I know, including myself, that has a newsletter, I mean maybe not everyone, but like puts a lot of time.
• 39:29
  SPEAKER_00: Like it's a it's a lot of time.
• 39:31
  SPEAKER_01: Yeah.
• 39:31
  SPEAKER_00: Um, like I've done a few or done two posts with Lenny.
• 39:34
  SPEAKER_00: Like he puts a ton of time into every newsletter.
• 39:36
  SPEAKER_00: Like it's not just like spit now.
• 39:39
  SPEAKER_00: Yeah.
• 39:39
  SPEAKER_00: Like they're research.
• 39:40
  SPEAKER_00: Like mine are very research.
• 39:41
  SPEAKER_00: They take uh like 40 hours and you still write 40 hours.
• 39:45
  SPEAKER_00: You write the whole thing yourself.
• 39:46
  SPEAKER_00: I write them.
• 39:47
  SPEAKER_00: Yes.
• 39:47
  SPEAKER_00: It's me.
• 39:48
  SPEAKER_00: I human.
• 39:48
  SPEAKER_00: I've tried to human brain.
• 39:50
  SPEAKER_00: I have two people that work for me work with me part-time or halftime.
• 39:53
  SPEAKER_00: Yeah.
• 39:53
  SPEAKER_00: Um, one really helps with all the partnership sponsorships shit sponsorship sponsors shit, they'll love that.
• 39:58
  SPEAKER_00: Sponsorship stuff.
• 40:00
  SPEAKER_00: And the other, Hallie, helps me with um a lot of like the paid subscriber stuff we're doing around AI and our MCP server and building, but I do that stuff too, and with editing.
• 40:09
  SPEAKER_00: Yeah.
• 40:10
  SPEAKER_00: And so, yeah, but I do the bulk of my writing myself, believe it or not.
• 40:15
  SPEAKER_01: So if somebody wants to have a newsletter, they want to be uh in a knowledge influencer, they want to build an audience, what should they be doing?
• 40:24
  SPEAKER_00: Well, I don't know.
• 40:24
  SPEAKER_00: Um, I mean, I think you have to find a lane.
• 40:28
  SPEAKER_00: I think I I'm not a great example of this because my newsletter is about like B2B marketing in general, but it's not about all of marketing.
• 40:34
  SPEAKER_00: It's about B2B marketing at startups.
• 40:36
  SPEAKER_00: I very much think of like a growth stage marketing leader when I'm writing it.
• 40:40
  SPEAKER_00: Like I'm thinking of like a series C.
• 40:41
  SPEAKER_00: So you have like a persona in mind.
• 40:43
  SPEAKER_00: Yeah, it's like a series B, series C head of marketing, which happens to be the people that I advise.
• 40:46
  SPEAKER_00: I also advise, I advise heads of marketing now more than founders that are at growth stage companies.
• 40:53
  SPEAKER_00: Um, and so I'm thinking of those people.
• 40:56
  SPEAKER_01: Yeah.
• 40:57
  SPEAKER_00: Um, and but my advice to other people is like go narrower.
• 41:01
  SPEAKER_00: Um, like if whether you're starting advising or starting a newsletter, is like have a niche.
• 41:06
  SPEAKER_00: Um, like if it's in marketing, like pick a lane.
• 41:10
  SPEAKER_00: Um, because it needs to be when someone thinks of something, they think of you.
• 41:14
  SPEAKER_00: Yeah, yeah.
• 41:14
  SPEAKER_00: And if they're just thinking of marketing, like they're probably not gonna think of you.
• 41:17
  SPEAKER_00: Sure.
• 41:17
  SPEAKER_00: Or if they're just thinking of like name another category, sales, they're not gonna think of you.
• 41:22
  SPEAKER_00: Yeah.
• 41:22
  SPEAKER_00: And so you've got to start with, well, what might they think of you?
• 41:26
  SPEAKER_00: Yeah.
• 41:26
  SPEAKER_00: Um, so you've got to, it's like with startups, like it's very hard to go really horizontal at the beginning.
• 41:31
  SPEAKER_00: Like I lived it at Asana.
• 41:32
  SPEAKER_00: Like having a niche and knowing exactly who you're going after is easier, and then you can expand from there if you want to, or just go deep in that niche.
• 41:38
  SPEAKER_00: Yeah.
• 41:39
  SPEAKER_01: A huge thank you to my friends at Granola for sponsoring the Good Works Talk Show.
• 41:42
  SPEAKER_01: I started using Granola as just a note taker, but now I use it for every type of meeting and conversation, from quick check-ins to creative collaborations and everything in between.
• 41:52
  SPEAKER_01: Granola is an AI notepad that transcribes meetings, whether online or in person, and it creates amazing summaries that you can chat with and you can ask follow-up questions to well after the meeting is over.
• 42:02
  SPEAKER_01: As a busy person with a full-time job and a couple of side projects, I truly couldn't keep track of all of it without granola.
• 42:09
  SPEAKER_01: It helps me stay focused and stay present while still capturing all the details and the important to-dos in the background.
• 42:14
  SPEAKER_01: I even used it on all of these episodes, so you'll be able to check the notes for each show and chat with them just like you were sitting here with us.
• 42:21
  SPEAKER_01: Granola also has features for following up and for drafting to-do lists.
• 42:26
  SPEAKER_01: It definitely saves me from dropping balls and it helps me do what I say I'll do.
• 42:30
  SPEAKER_01: The best way to check it out is to try it in your next meeting.
• 42:33
  SPEAKER_01: To read the summary of today's show and chat with that summary, you can visit granola.ai slash goodwork.
• 42:39
  SPEAKER_01: And if you're a new granola user, you'll get three months free.
• 42:42
  SPEAKER_01: Again, that's granola.ai slash goodwork.
• 42:46
  SPEAKER_01: All right, and now we're gonna ask Granola to ask you a question.
• 42:49
  SPEAKER_00: Oh.
• 42:50
  SPEAKER_00: Turn it over to the machine.
• 42:51
  SPEAKER_01: Turn it over.
• 42:52
  SPEAKER_01: Only a little bit.
• 42:53
  SPEAKER_01: Okay.
• 42:54
  SPEAKER_01: What's a piece of marketing advice you used to give that you no longer believe?
• 42:59
  SPEAKER_00: Oh.
• 43:01
  SPEAKER_00: Oh.
• 43:02
  SPEAKER_00: Complicated question.
• 43:03
  SPEAKER_00: Nuanced question, granola.
• 43:05
  SPEAKER_00: Um I used to give the advice that like a long time, so a long time ago, my advice was like when you're picking a company in manners that like it can be successful and like they can win, you know, if assuming you're doing this for some sort of financial gain or career gain, um, the sort of world we often are, or like you have to love the product and you have to, you know, get along with the founders.
• 43:28
  SPEAKER_00: And I think now my advice for like marketing leaders is like, you gotta love the founders.
• 43:35
  SPEAKER_00: And uh if the product you don't love it, does the audience love it?
• 43:40
  SPEAKER_00: Like that matters.
• 43:41
  SPEAKER_00: It matters that people like the product and it's a good product.
• 43:43
  SPEAKER_00: It matters that you think that you can win.
• 43:45
  SPEAKER_00: But both of those things can be true.
• 43:47
  SPEAKER_00: And if you don't feel like you bond with the founder and like want them to win, and that they value marketing and value you, like, don't work there, like point blank.
• 43:57
  SPEAKER_00: Um so I think that like.
• 44:00
  SPEAKER_00: You have to make I think people are like, oh, it'll be fine.
• 44:03
  SPEAKER_00: Like with this kind of awkward interview, but it's this just you know, founders don't get marketing.
• 44:08
  SPEAKER_00: It's like you have to feel like they value marketing.
• 44:11
  SPEAKER_00: And so I think I used to just have that in like a list of things.
• 44:14
  SPEAKER_00: Maybe this is a cop-out, and now it's like the thing.
• 44:16
  SPEAKER_00: The thing.
• 44:16
  SPEAKER_00: Like you've got to be.
• 44:17
  SPEAKER_00: Is that at any size?
• 44:19
  SPEAKER_00: Any stage.
• 44:20
  SPEAKER_00: In a marketing leadership role, that's at any stage.
• 44:22
  SPEAKER_00: Like you have to like understand, like we in that case, maybe it's like the whole exec team, but like you have to know how that feels.
• 44:30
  SPEAKER_00: Um, and I consider myself very much like a marketer's marketer.
• 44:34
  SPEAKER_00: Like, I'm so much better at managing marketers than I am at like managing relationships with other teams, and I recognize that about myself.
• 44:41
  SPEAKER_00: But I, you know, I I wish I'd spent more time working on those relationships or getting better at that piece too.
• 44:47
  SPEAKER_00: And I'd wish I'd spent more time really like thinking about the founders that I was working with.
• 44:53
  SPEAKER_00: Yeah.
• 44:53
  SPEAKER_00: Great.
• 44:54
  SPEAKER_00: I worked with some great founders, not that's not to say, but well, thank you for that, Grenola.
• 44:58
  SPEAKER_01: Is that is that good advice?
• 44:59
  SPEAKER_01: That was great.
• 45:00
  SPEAKER_01: I yes, I think it it also that was good advice then, and it's good advice now, it's just different advice.
• 45:05
  SPEAKER_01: The times have changed.
• 45:07
  SPEAKER_01: Times have changed.
• 45:08
  SPEAKER_01: Okay.
• 45:09
  SPEAKER_01: I think this is the last question.
• 45:11
  SPEAKER_01: When you think about work, what are you like, what do you try to get out of work now?
• 45:16
  SPEAKER_01: Like, what are what is work to you?
• 45:19
  SPEAKER_01: Oh God.
• 45:20
  SPEAKER_00: This is also like therapy.
• 45:22
  SPEAKER_00: Um, I work too much.
• 45:25
  SPEAKER_00: I'm a workaholic, for sure.
• 45:27
  SPEAKER_00: Um, and it's worse when I work for myself.
• 45:29
  SPEAKER_00: So I work more now than I ever did.
• 45:30
  SPEAKER_00: I think a lot of people are like, oh, do you work like 30 hours a week?
• 45:33
  SPEAKER_00: I'm like, absolutely not.
• 45:34
  SPEAKER_00: Yeah.
• 45:34
  SPEAKER_00: Um, that was like kind of the intention when I started.
• 45:37
  SPEAKER_00: You could, but it wouldn't you wouldn't perform to the level that you do.
• 45:40
  SPEAKER_00: I if I were just doing a newsletter, I could do that.
• 45:45
  SPEAKER_00: Um, if I was just advising, I could definitely do that.
• 45:48
  SPEAKER_00: I can't do the newsletter without advising people.
• 45:51
  SPEAKER_00: Like it wouldn't be in the weeds enough.
• 45:53
  SPEAKER_00: Um I could definitely advise people if I didn't have the newsletter, but for a long time that's, and maybe still that's how I got advice.
• 45:59
  SPEAKER_00: So they they work well with each other.
• 46:02
  SPEAKER_00: Also for like the the revenue lumpiness, you know, they work together well.
• 46:07
  SPEAKER_00: And so I have to do both of those things.
• 46:09
  SPEAKER_00: So so I could, but I just choose to do other things.
• 46:12
  SPEAKER_00: I choose to be like, oh, I'm gonna like go big on like we're literally like building out AI tools, we're building out almost like an AI marketing product right now, essentially.
• 46:20
  SPEAKER_00: And so like I always want to be going and doing something new there.
• 46:23
  SPEAKER_00: That's what keeps it interesting.
• 46:24
  SPEAKER_00: I had a fund um a few years back.
• 46:26
  SPEAKER_00: Um, I mean, we're still invested in these companies, but I raised a fund with my um former business partner, Kathleen, and we invested in 35 companies, like didn't have to do that too.
• 46:35
  SPEAKER_00: And I wanted to refocus um and decided not to do a second fund.
• 46:41
  SPEAKER_00: Um and so is work a tool.
• 46:43
  SPEAKER_00: I'm not answering your question.
• 46:44
  SPEAKER_01: That's okay.
• 46:45
  SPEAKER_01: Like, yeah, tell me what what what do you want to get at?
• 46:48
  SPEAKER_01: Like, what do you use work for?
• 46:49
  SPEAKER_01: Is work a tool for learning?
• 46:51
  SPEAKER_01: Is it a tool for influence?
• 46:52
  SPEAKER_01: Is it a tool for money?
• 46:53
  SPEAKER_01: Like, what what do you what are your priorities for work?
• 46:56
  SPEAKER_00: For money for sure.
• 46:57
  SPEAKER_00: Like, you know, I mean, obviously.
• 47:00
  SPEAKER_00: Yeah.
• 47:00
  SPEAKER_00: Um, but I think for me, I need to find something like intellectually interesting.
• 47:05
  SPEAKER_00: And so I need to find it like I get bored, like I said.
• 47:08
  SPEAKER_00: We're back to the change.
• 47:09
  SPEAKER_00: Get it, I just get bored.
• 47:11
  SPEAKER_00: Yeah.
• 47:11
  SPEAKER_00: And so it needs to feel interesting and new.
• 47:12
  SPEAKER_00: So that's why I'm always like layering on new things, or like changing up the composition of what I do, or like going deep in somewhere, something new.
• 47:18
  SPEAKER_00: So it has to feel like new and interesting.
• 47:20
  SPEAKER_00: And so I've been able to like reinvent like this.
• 47:22
  SPEAKER_00: Is the longest job I've ever had by like a lot.
• 47:24
  SPEAKER_00: Yeah.
• 47:24
  SPEAKER_00: I've been doing this for almost six years.
• 47:26
  SPEAKER_00: This has been many jobs in one.
• 47:27
  SPEAKER_00: But it's been so many jobs, it has so many iterations.
• 47:30
  SPEAKER_00: It doesn't feel the same one year to the next or six months to the next.
• 47:33
  SPEAKER_00: It's very been very different.
• 47:35
  SPEAKER_00: Yep.
• 47:36
  SPEAKER_00: And so that's like really important to me, I think, to just keep it interesting.
• 47:39
  SPEAKER_00: And then also, like, I want like freedom and flexibility now in my career.
• 47:42
  SPEAKER_00: And that's like, I think for a while I thought I just like wanted to be the CMO at like the biggest company I could get to.
• 47:49
  SPEAKER_00: Yeah.
• 47:49
  SPEAKER_00: That became not a thing somewhere along the way.
• 47:54
  SPEAKER_00: And it just became a thing that I wanted to like have freedom and flexibility um in my career while also like, you know, being able to still have a career or whatever that is.
• 48:03
  SPEAKER_00: And so that's like my priority now.
• 48:06
  SPEAKER_00: All that said, I work all the time, so I don't know why I'm optimizing for freedom and flexibility, but I still feel like I have it.
• 48:12
  SPEAKER_01: Well, now you have that to take to therapy.
• 48:14
  SPEAKER_01: There's so many things I need to take to therapy here.
• 48:17
  SPEAKER_00: Um whoa.
• 48:18
  SPEAKER_00: You should follow up.
• 48:19
  SPEAKER_00: You should have like over there in the other side of your yard, like a post-therapy session.
• 48:24
  SPEAKER_00: I'll check in with you in two months.
• 48:26
  SPEAKER_00: People that go to Burning Man and then have to come home and like do decompression.
• 48:31
  SPEAKER_01: I think you need that.
• 48:32
  SPEAKER_01: Okay, amazing.
• 48:33
  SPEAKER_01: Well, thank you so much for bearing with me through the therapy.
• 48:36
  SPEAKER_01: Yeah, this is great.
• 48:37
  SPEAKER_01: I thanks.
• 48:38
  SPEAKER_01: I really appreciate it, and um, this has been good work.