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The art of cold emails · The Generalist World Pod

• 0:00
  Hey, it's Millie, and welcome to the Generalist World Podcast. This is the podcast for people who have never fit into a box at work, and to be honest, we don't really want to.
• 0:09
  Every week, I chat with a new member of Generalist World, and I share their stories, their philosophies, their frameworks of how they are living their life and creating work that actually aligns with their generalist skill set.
• 0:22
  So if you are someone who has had a non-linear, squiggly career, this is the podcast for you. Olivia, I'm so excited to have you on the podcast.
• 0:30
  We have been in each other's, like, internet circles for many years, a very long time, and then we finally got to meet in person this year in Ohio, which was so cool. Crazy.
• 0:41
  Of all the freaking places in the world [laughs].
• 0:45
  [laughs] Um, so I know that you are just this absolute fountain of knowledge and experience, and I know that you do things a little bit differently, I think it's fair to say.
• 0:56
  So I'm hoping in this podcast episode today we can just, like... I'm kinda gonna, like, fire hose people. Fire. Love it. This is the, this is the theme of today.
• 1:06
  And so if you're listening, buckle up, cancel whatever else you're doing, come, sit down, focus, take notes, because this is going to be an excellent episode. I can feel it. Let's frame it for people. Let's frame it.
• 1:19
  So we know you're a squiggly careerist. You're a generalist. Give people a flavor. What kind of generalist are you? Oh, man. I didn't know I was a generalist.
• 1:30
  I mean, I guess I knew, but of course you and a lot of people who have followed the Generalist World movement really, like, let me define that, as I'm sure a lot of other guests on this podcast have said.
• 1:41
  I think it started even before the professional career arc began in, I don't know, high school and college. I studied finance and sustainability, already two very different things.
• 1:52
  And everyone was like, "Why both of those?" And it's like, "I don't know, 'cause I'm interested in both. Like, that, that makes sense to me." But I was always involved in startup things, hackathons.
• 2:03
  Like, that's what I really, like, was thriving for in high school and in college. People are surprised to hear sometimes that... I don't know if you're familiar with DECA.
• 2:11
  It's, like, this business organization that people in America go through in high school. And I was a poms cheerleader in the marching band.
• 2:19
  So I would, like, wear my marching band, like, doing my little thing, and then change into the poms uniform, and then, like, go run on the field and do the dance, and then, like, the next day be not in school because I was the state president for Illinois DECA, which is, like, the business organization for...
• 2:35
  So it just was always a little bit of a generalist, I think, even back then.
• 2:39
  But career-wise, I started my career in investment banking in New York City doing industrials M&A, which is timber, paper, and packaging companies trying to merge, refinance, all the things.
• 2:52
  Soon as I could, took the exit, joined Techstars, where I was the VC analyst but also working with programs. So what, what are we gonna take these amazing entrepreneurs through for 12 weeks?
• 3:05
  And from there, jumped into another startup where it was another program for founders. At the same time, though, was always doing something else on the side. Maybe that was an event planning side hustle.
• 3:17
  Um, I think at some point in...
• 3:19
  We were on a vacation in Mumbai for, like, three months between, between jobs or something, and I was like, "I'll do a marketing, um, go-to-market gig for a digital marketing company in Mumbai."
• 3:29
  So there I was on the train in Mumbai, like, going to this. I don't think I got paid for that, but it was really fun. And my mom was like, "We're supposed to be on vacation." I was like, "Yeah, but this was cool."
• 3:39
  So in between all that, started my own startup for a little bit, raised money for it. It was great. It was supposed to connect first-time founders to the right investors for them.
• 3:47
  It honestly kind of ended up turning into a little bit of a community platform. Go figure. Like, raised money for that.
• 3:52
  Decided I didn't actually want to maybe do that full time, but part of the reason was the founder program I was in at Launch House was in LA with a bunch of other founders, and they said, "Why don't you just join us instead?
• 4:05
  We also serve founders." So did that. Then I joined as a community manager for a media company. Never thought I would work at a media company.
• 4:13
  And just very quickly, I think it was, like, eight months in, landed up in the product seat. Uh, so now it was a very technical role all of a sudden, and just really leaned into that. So yeah, kind of all over the place.
• 4:23
  I also do agentic agent creation workflows for a mid-sized market research firm right now too. Yeah, really, really squiggly. Really generalist, I think. [laughs] Wow. And how do you decide what's next?
• 4:36
  So that is a very squiggly path. Is it that an opportunity just lands on your door and you evaluate it in the moment? Like, what...
• 4:44
  Talk me through your thought process of when you say heck yes to something and when you say no. Yeah, that's a great question. So I think it depends, like, what phase of my career I was in.
• 4:53
  So earlier on, it was a lot more me knocking on a lot of different doors. Even for banking, you know, I didn't make the decision based off of how many people are gonna know this bank.
• 5:04
  It's called Perella Weinberg Partners. If you're in finance, you probably are familiar, but otherwise you're like, "That's not Goldman Sachs. That's not JP Morgan. Like, I don't know what the heck this bank is."
• 5:13
  Made the decision based off of the people and who I was gonna get to work with and how interesting the deals were gonna be, and how much autonomy someone as an analyst would have to actually run the deal process.
• 5:25
  So really, really small teams versus maybe at a bigger bank it's, like, 20 people on a project, a lot of different red tape to get through, and at Perella it was, like, three people trying to get, like, a whatever, multimillion-dollar deal done, which was way more exciting.
• 5:38
  So I think that's kind of how I've always thought about what opportunities to go after. But no, I, I wish I could say they were always knocking on my door.
• 5:44
  I definitely feel like you have to, you have to create systems to knock on a lot of doors. That, I think, in, in high school, early college, I actually had a Airtable with every single person that I had ever met.
• 5:58
  Maybe that's a little psychotic, but it was like, "I thought you were interesting. I'm adding you to my list of people that I think are really interesting or someone I wanna stay connected to," and that has paid off.
• 6:08
  The RO- I mean, in spades. In spades, being able to have a system to remember, and not necessarily network.
• 6:14
  Like, I don't reach out to everybody every time, but if, like, someone had told me they really love Spider-Man and a new Spider-Man movie's coming out, I'm reaching out.
• 6:23
  I'm talking about the Spider-Man movie, even if it's been, you know, six months or so. So I think that's how I've been able to create some, some of the opportunities that I've gotten. Amazing.
• 6:33
  And when you are in a company, so there's, like, there's two threads, right?
• 6:38
  There's one where it's like, okay, I'm either seeking a new job or I've, I've, I've landed this new job, but you also have this kind of talent when you're within a company to create a role or to create, like, a step change for your career.
• 6:51
  So, like, talk us through that. It's the best when you feel... You don't even have to believe it, you just have to, like, think you can do it.
• 6:58
  Like, "I'm gonna join this company to maybe do this," but then carve your own path. So a couple of maybe examples. I think at Work Week, the job description was, like, partnersh- community partnerships.
• 7:10
  Honestly, I don't even think I fully read that job description.
• 7:13
  I just knew I wanted to work with Adam and that team, and I thought the company was really cool, and I saw the word community in there, and I was like, "That's good enough."
• 7:19
  Like, and then I just emailed him and said, "Here's what I would like to do at Work Week, what I think I know how to do really well, how I could help," et cetera.
• 7:28
  And so I don't know if that was actually the role they were hiring for, if they ju- like, literally did want to help their creators, like, build partnerships with other communities or other people.
• 7:39
  We ended up just launching communities for the creators there, and that was the role. But then once I was there, I, I did that, right? Like, two weeks in, I remember we launched our first community.
• 7:47
  It was a $3,000 annual membership for a heal- healthcare executive community. Two weeks in, we get a Slack ping of, you know, the Stripe payment going through, and Adam's like, "What is that?
• 7:58
  Like, did we just launch a new product? Like, what... " I was like, "Isn't that... [laughs] Wait, isn't that what you hired me to do? I thought that's what I was supposed to do here." And he was just like, "Already?"
• 8:06
  I'm like, "Yeah. Like, you guys had the baseline to do it." But because I also try to... I don't know, I like to, I... not nosy, but at a company, I feel like I do kind of keep an eye on, like, all the things going on.
• 8:18
  Like, is there an opportunity to do more? Like, "Oh, hey, we're having an event here, and then there's a podcast, and how do we, like, tie these things together? Where's the flywheel here?"
• 8:27
  And so I was like, "I think we need to build our own platform. Like, I think we need to just do this in-house. Can we do it?" But before I pitched that, I went to an Apple Store.
• 8:35
  I didn't have an iPad or, like, not a, not... I wasn't professionally a designer.
• 8:40
  Could Figma, but went to an iPad, like, drew all the wire frames for, like, the one of this community platform and was like, "We could build this."
• 8:47
  And, like, then could totally control the user's experience and, like, do exactly what we need to do to have a great outcome for the business, of course, but also for all the members and the creators.
• 8:58
  So I think you don't necessarily need to pitch, kind of like the VC process where you pitch, you wait for an answer, then maybe it happens. You, like, follow up, wait for an answer. Like, just go do the thing.
• 9:10
  I think sometimes you just have to be like, "I really wanna do this. I wanna see if we can do it." And the more you come to whoever is the ultimate decision-maker with, "Already have the plan." Like, "Here's the plan.
• 9:20
  I think we can really do this, and I know how to do this much of it, and here's where we're gonna need to bring in someone else," makes the decision to say yes a lot easier.
• 9:29
  And, you know, I think there's a little bit of a counter-narrative these days where you shouldn't do the job before you are compensated for it, have the title for it, and I understand where that's coming from.
• 9:39
  I think when you're earlier on in your career, though, having that, like, mindset might, you might actually miss out on opportunities.
• 9:47
  All, actually, most of the time, I just, I never had the job title or got paid to do the extra thing or things that I was doing. Even Techstars, it was an internship. It was, like, a really...
• 9:57
  It wasn't a high-paying job, and I was supposed to just be analyzing the, the founders coming through. And instead I said, "No, let me run the program, too, and also let's do a big event. Like, I'll do the event.
• 10:06
  Like, let me just, like, put it together. I'll make the intros, like, all the thing. I'll build the systems for it." And you just, you learn a lot. You get the next opportunity when it's available.
• 10:15
  And then sometimes if they don't realize how much else you're doing, you do have to say, like, "Hey, by the way, I'm been doing a product job for, like, eight months now.
• 10:22
  Do you think, do you think I could, like, officially just do the job and also maybe get comped for that job in addition to being the community manager for five communities? I don't know. What do you think?"
• 10:32
  And so yes, [laughs] it's like a give and take, and you should be aware of your own limits and stuff.
• 10:36
  But I don't know, just, just do the job, and more often than not, if you're doing it and it's good results, you just created your own role.
• 10:44
  Obsessed, and I feel like a fun fact should be about you, "Oh, yeah, I didn't have an iPad, so I went to the Apple Store." [laughs] They have them there.
• 10:53
  You can draw and stuff and then save the picture, send it to yourself. It's great. [laughs] It says a lot about your character in the best way possible, so I, I love that.
• 11:02
  I know that you're excellent at cold emails, and I know that you've got a framework that you say it's never failed you. I wonder, would you be open to sharing that framework? Sure.
• 11:12
  I actually just shared this with, um, another Generalist World community member. Um, I won't say his name for privacy, but he was like, "Oh my God, you can just do that?" I'm like, "You can just do that."
• 11:21
  So the framework is actually quite simple. I do think that it's less about what's actually in the email.
• 11:27
  That is important, but you actually start, like, months, maybe even years before that email's about to get sent, and it doesn't mean that you have to know that person one-on-one or you have to, like, already have their email or have a direct connection to them.
• 11:41
  But usually, if you're getting to a point where you want to even take the time to craft this email and send it, you've either kept up with that person on their socials or you've, like, seen...
• 11:52
  You, there's something you admire about them or their team or the business or the company, or maybe it's an opportunity that you've been seeing.
• 11:59
  Like, when I was trying to exit- Banking and go back into maybe sustainability, a, a venture f- firm that invested in green things. I was keeping up with that just as much as I was keeping up with Timber.
• 12:10
  So maybe you're already doing that on the side, in your ear- like nightly reading or whatever.
• 12:15
  But then there will be a moment where I think there's a job that's interesting, maybe there isn't actually one, but you really think that the company has an opportunity to do something cool, and that's when you, that's when you send the cold email.
• 12:26
  So I try, you know, I think you have, like, X number of cards. I try not to send the email when I actually don't have anything meaningful, legitimate, exciting to offer or say.
• 12:36
  Or if I think the opportunity's gonna come in, like, a few months, I'll just wait. Like, I don't need to be in your inbox yet.
• 12:42
  So maybe that's part one, is, like, knowing when to send it is just as important as what's in it. And then who to send it to. So again, you might not always have that direct connection.
• 12:52
  But I do think the warm intro is a little over-hyped. I do think it's underrated to just go cold and, again, write the, write, write a good email, but I don't think you need to have someone connect you every single time.
• 13:06
  But yeah, so w- the framework for the email. It's usually very short, because I know that people, these people are probably getting a lot of cold emails or a lot of sales pitches or whatever.
• 13:14
  So it's one sentence on, "Hey, I'm Olivia. Maybe you recognize me from somewhere." Maybe.
• 13:21
  And sometimes it's nothing and I'll just say, "Hey," but I'll link my LinkedIn in there so they can click it and just quickly get, like, a good picture. But then what...
• 13:30
  W- like, again, so much goes into the things before the cold emails. If they're clicking on my LinkedIn, I better have things on my LinkedIn that are relevant or gives them a good idea of who I am.
• 13:41
  And that doesn't mean, I don't even have a head cover photo, I think. It's just, like, the... Which I should change. But I don't have one. It's what are my last three posts?
• 13:49
  Like, is it gonna be something they can read and, and be like, "Oh, I, okay, I'm getting why maybe she reached out already." They come back to the email.
• 13:55
  Like, what's the user experience of that person reading that email is what I think about. Product lens really helps me think about that. Like, as they're going through the email, they're clicking on things.
• 14:03
  Maybe they're skipping, skimming this. So everything is user experience. [laughs] Maybe I should go back and, like, be a professional UX designer.
• 14:11
  I think there's so much magic in that and so much thought that goes into that. But even the email, the way it's formatted.
• 14:16
  So then they're coming to the next thing, what, like, what am I gonna do to help you, or what's the opportunity? So, "Hey, I think," for Work Week as an example, "you have an audience of X."
• 14:27
  So research has gone into this, right? You have an audience of 500,000 people across these six industries, so now they know, okay, she already knows what this business is about and how we make money.
• 14:36
  Like, I want them to understand that I understand your business model. And then I see an opportunity for X because X, Y, Z. Here's how I think I can help, and then it's bullet, bullet, bullet, bullet.
• 14:48
  And let me know if this is interesting to you. And there's two things I always add at the end. I give them options. Not everybody wants to hop on a call, okay? Not everybody has 10 minutes.
• 14:57
  Um, so e- if I am asking for a call, it's 10 minutes, but not to learn more, where you're telling me stuff.
• 15:03
  It's 10 minutes so I can walk you through this in more detail, share my plan, or let me know if you want more depth in any of this. So that's option two. I guess the third option is, or we can just chat async.
• 15:15
  If that founder or that person has seemed pretty informal online and they've somehow somewhere said, like, "The best relationships are over text," or something, I will drop my email, be like, "It's, it's easier to text me.
• 15:26
  Like, here you go. Here's my number." They don't always take you up on that. Sometimes they do. And that's actually what happened with Beehive. Tyler just texted me, which was great.
• 15:34
  Very easy to keep [laughs] that conversation going, right? So give them a couple options, and then leave it at that. That's it. Like, I'm not following up in two days, four days. I'll wait.
• 15:43
  I'll wait, I'll wait, I'll wait. And then I won't reply to that email necessarily. I'll find a different thing of theirs to reply to. So if they have a newsletter, I'll reply to their newsletter.
• 15:54
  Again, if there's something real I have to say. So for Tyler, I think it was he had written about, like, how it was frustrating for him to have to do so many one-on-ones, and my reply was literally one sentence.
• 16:07
  It was, "I don't do one-on-ones either. I think they're a waste of time. I don't need a manager. Like, I just wanna get the thing done. What do you think?" Like, that kind of thing.
• 16:14
  So if you have something real to say that adds on to the thing you already said before, helps multi-channel. That's, I guess that's marketing, right? Multi-channel touchpoint.
• 16:22
  So I don't know, I treat it almost like a founder. I, I am the founder for myself and my career. So that's the framework for the cold email. But a lot goes into it before, after, and during.
• 16:33
  I think the world of emails would be a lot better off if people took this approach. I- it's something I, I've noticed this week where, as you know, I've been, I've been going out to hire, and it went completely bananas.
• 16:45
  Mm-hmm. I think it was, like, nearly 300,000 people have seen the post, and so I've had a baptism of fire in emails. And I've got to see the real spectrum of email patterns, I think I would call it.
• 16:58
  And the vast, vast majority are not thinking of emails in terms of UX, in terms of like- [laughs]... oh, there's a real person reading this on the other side. Right, yeah.
• 17:08
  And this is probably gonna be a pretty horrible experience for them to... And you can just assume these days, if you're applying for a job, you can assume 500 other people are applying.
• 17:18
  Like, that can be a pretty fair assumption.
• 17:21
  And so I would really put myself in the shoes of being, like, the founder, the person on the other side reading it, to not only stand out in that email, but to build the relationship for next time.
• 17:32
  And I also, just as a side note, one of my favorite ways to get in touch with hard-to-reach people is to reply to their newsletter. It's so underrated. Like, I think
• 17:42
  people think that, like, newsletter writers are, are really, really busy, and they are. But I love it when someone replies directly- Right... to my newsletter. It's different than, like, a cold email.
• 17:52
  It, like, gives them joy, right? Like, "Oh, someone actually read this. Not only did they read it, they took the time to reply, so I know they really read it."
• 18:00
  Like, it's Make people ha- I mean, like, everything in product or no, you know, just in general, like, make someone, give them a reason to smile or laugh.
• 18:08
  And, like, what I really took away from that is how genuine your approach is, where you're not, like, it's not this, like, sequence that, like, follows up in two days, four days, six days.
• 18:16
  It's like, "Oh, can I actually add something here?" Which, like, if you, if you were in, in person, if you were in real life in a room with someone, you wouldn't just, like, go tapping on their shoulder- [laughs]...
• 18:27
  every, like, 10 minutes. Be like, "Oh, do, do you wanna- Yeah... do you wanna come talk to me now?" You'd be like, "Oh, I'm going for lunch. Now maybe it's a good time."
• 18:34
  So yeah, I think, oh, email, there, there's a lot of lessons for folks to learn, and hopefully that framework can give them a really solid starting point of how to write better cold emails and get better responses.
• 18:46
  Hope so. I think, you know, there is something to be said. There are people that just play the numbers game with, "I'm gonna send X number of emails." Mm. "And, like, the odds, the math, maths, where like- Yeah...
• 18:57
  1% of them are gonna reply to me." I, I think that's, I mean, personally, I think that's exhausting. I think you have to weigh the pros and cons of your reputation and your career. Yeah.
• 19:07
  And if you are doing that, the odds are you're probably not also, like, really thinking about how you're customizing it with Mail Merge. "Hey, Millie," like- Yeah... people know, like those are...
• 19:17
  I mean, email's been long and lo- around long enough now where it's super obvious to know when you're mail merging. Okay. We're gonna go into a segment. I'm just making this up as I go. There's gonna be a segment.
• 19:27
  Awesome. And the segment is around your four favorite frameworks. Four favorite frameworks, that could be a segment. That's catchy.
• 19:35
  So I'm gonna say a framework, and I want you to give me a 30-second to one-minute max spiel on why this matters to you, what you've learned, some kind of tip. S- Speak to this framework. Okay, sounds good. Okay.
• 19:50
  James, this is a good time to have pa, pa, pa, pa, like fireworks or something. Okay. Number one, your circumstances might be out of your control today, but they are not out of your control tomorrow. Oh, man.
• 20:03
  Yeah, I think, um, this one means a lot to me because I think I just am someone who believes that you control your out- the outcomes in your life.
• 20:10
  You control what happens tomorrow for yourself, and it's, it would, I think, you know, maybe someone who has, like, read my life story would be like, "It'd be so easy for her to just be like, 'Man, everything is, like, really fucking hard.'"
• 20:21
  And yeah, everything is just really hard, and I wasn't born into these certain circumstances or what- whatever.
• 20:27
  Like, there's always something for s- someone, I would say even, like, children of really famous people, like, sometimes could struggle with that. Like, "Oh, this is a disadvantage for me."
• 20:35
  And I just think, you know, you just have control over every single decision that you can make. And but you have to, like, genuinely believe that. Like, if you believe that- Mm...
• 20:44
  then I think if there's some, probably some science in psychology, some people say manifestation works for this reason. I probably believe that, too.
• 20:51
  I'm not really sitting there, like, manifesting every day, but I think that's still what's happening in my brain- Yeah... of like, "Nope, I, I'm, I wanna do this, and I'm gonna just go make it happen for myself."
• 21:01
  Yeah, I don't, I think that's why it matters to me so much 'cause it would, again, it would be very easy to just be like, "Mm, this is just, like, what was dealt to me," and I think that's the hardest way to live your life.
• 21:10
  Like, someone else made decisions for you and your circumstances? Oh, man, like, it's a tough pill for me to swallow. So that's why it matters so much to me.
• 21:17
  And I think, yeah, again, today, maybe you're s- you're where you're at, but do something today that makes tomorrow different. And you can make that in terms of literal days, hours, or years- Mm...
• 21:26
  um, of, and decades of your life. Love. Number two, send the freaking cold email. Oh my gosh. Well, we just talked about this. Yeah. [laughs] I think one thing about me is I am never really afraid to go up to anybody.
• 21:42
  Like, I think everyone is human.
• 21:43
  Like, if you put someone I super, super admire, I mean, like Jen Psaki, I don't know if, if you're familiar with her, but she's, you know, Jen Psaki's in the room, I'm just gonna go up to Jen Psaki.
• 21:52
  Again, I must have something to say to her, like something important. I'm not just gonna go there and be like, "I'm your biggest fan," and have nothing else to add. But there was a, a quick story here.
• 22:00
  We were at a mixer for my husband's residency class and all the attendings, like, all these, like, very accomplished doctors, and he was like, "Oh my God, that attending, she, like, really scares me, but she's so good at her job," and blah, blah, blah.
• 22:11
  I'm like, "Well, let's go talk to her." And he's like, "Absolutely not. We can't just go up to her." I'm like, "Okay, I'm gonna go up to her," so I do.
• 22:18
  And I just, like, have a perfectly normal conversation with her, I think about, like, gardening or something. And I could see him in the corner just, like, praying, like, "Oh my God, she's doing it.
• 22:26
  She's talking to this woman." I'm like, "She's just a wonderful woman who's really good at her job." Go up to anyone, talk to anyone. The, everyone is human. Mm.
• 22:34
  You don't have to be this, like, accomplished person to have a conversation with somebody. So send the cold email, same framework, in person or virtually. [laughs] I'm pumped.
• 22:44
  Okay, number three, there is always a third way. Yeah. Oh my God, you should have seen the things I went through for my wedding. I was like, "Oh, the vendor told me I can't? No, there's another way."
• 22:56
  Like, there's always a way. Let's think about, let's be creative. Let's brainstorm. Like, we have to DIY it? Okay, I guess we're gonna DIY it. Like, I just, I think this is true for career. This is true every day.
• 23:07
  As someone in the product seat, there is always a reason why the approach you wanna take is too hard, it's gonna take too long, require so much more research, all the things, and there just has to be, like, what's the MVP version of this?
• 23:19
  You can compromise that. Sometimes that's the right thing to do, but I think there's just... Wait, there's probably, someone's probably done something like this before. Like, what did they take?
• 23:28
  A good example, very tactical, apps. Every community wants a mobile app. Other platforms charge $15,000 to give you a mobile app, but there's the, there's a PWA, which is the sa- It has terrible branding.
• 23:40
  I'm gonna work on rebranding that for the, for everyone's sake. But it is an app. It does everything an app would do. Can we just launch with that? Mm.
• 23:47
  Like, can we still give people the, the f- what, why do they want the app? So I just, big believer in, there's not really ever a black and white or a one or two. There's always a plan C.
• 23:56
  And again, that kind of goes back to number one. If you're trying to change your circumstances, gotta, gotta find that third path to get there. Love. Okay, number four.
• 24:06
  In the course of a lifetime, what does it even matter? I love that one.
• 24:10
  That one has stuck with me since middle school, since when I read the book, I think it was Walk Two Moons, and that one quote from that book, like it's on my bookshelf, like it never, I never forget it, because I- it's so easy to go into, "Oh my God, what if this?"
• 24:22
  or, "What if that?"
• 24:23
  And all these things that can happen, and for people that like have a very strong internal monologue, it can be debilitating of just all the what if scenarios, and it's like, "Wait, this really doesn't matter."
• 24:35
  It also really helps when you're thinking of plan A, plan B, and plan C, like what can you give up to do the thing? So yeah, most things don't matter. There are very few irreversible decisions in your life.
• 24:46
  Probably the biggest one is like who you marry. I guess that's even reversible. Yeah. So you know what? Like [laughs] really in the course of a whole lifetime, like 80 years- It's so true.
• 24:54
  It's so true, and it's really liberating- So...
• 24:56
  when you actually can feel that and you're like, "Ah," it feels so important, and it feels like it's like the biggest thing in the world at the time, but even in like if you, even in like a year or six months or sometimes a week, you're like, "Oh, that wasn't that big of a deal.
• 25:11
  It was fine." Yeah. Okay. I am dying to hear your predictions. I wanna hear, what do you think is coming? Where do you think the world, specifically the world of work, what are your predictions for what's coming next?
• 25:25
  Okay. World of work, I think we're gonna see some really kooky titles, like amazingly weird titles that are coming, and examples, that's already kind of happening, like there's creative technologist.
• 25:36
  What a wonderful new title that is coming- Mm... in the workplace. Go-to-market engineering. I bet there's a community engineer. I mean, people already ha- that already existed, community architects, right? But like
• 25:48
  what a traditional title was, I think, is going out the window.
• 25:51
  Another example maybe I can give is the idea of a product designer versus an engineer versus a product person, like I think all three of those can start really melding and kind of being the same, and at, at Workweek we landed on builder.
• 26:04
  Like all of us are just builders. We can all kind of dip into each other's like fields a little more. I personally think that's so exciting. Um, you are not limited by, again, what your title is.
• 26:14
  You can now, it's like everyone's cool with everyone just like doing something a little more than what they were s- technically supposed to do in their scope of work.
• 26:21
  So excited for the really, really fun, cool new titles. Um, other predictions, okay, I, this one I'm surprised it hasn't already happened, but I do think almost everyone at work is gonna be required to create content.
• 26:36
  I think it's gonna be like the new keyboard.
• 26:38
  Everyone probably needs to know how to type or write a good email, and being able to create content, whatever the format, audio, video, newsletter, like whatever, I think every employee is maybe not gonna be like forcefully expected to, but I'm gonna, I think we'll see it more in the nice to have bullet points, the bonuses more and more.
• 26:58
  I love that.
• 26:59
  And I can imagine if someone is listening to this, and they are like either petrified or like repulsed by content where they're like, "I don't wanna make content," I would like frame it for them that as someone who makes a lot of content, it's just comms.
• 27:13
  You, you're just communicating, and you're doing it every day already.
• 27:17
  You're, every time you send a Slack message or an email, this is literally all content, and the skill of creating, to your point, I think is going to get even more and more valuable with AI like seeping into all areas.
• 27:34
  If you can create this like original, creative, clear content that like resonates and helps shift people, uh, and a really incredible skill to have.
• 27:44
  Another framework that I like to think about, 'cause it also petrifies me, is think of it like if I have something to teach, like I want more people to know this.
• 27:52
  An, an example is I really had, I was very passionate about helping young people understand their finances better because I had the background, but I wasn't really using it in work anymore, but I like thought it was important.
• 28:02
  So created a like adulting 101 course, and it was not exactly content, like I wasn't doing it on social media. It was like a webinar thing, but I did record them, and I guess I could've put it out.
• 28:13
  So it's more like you're probably already doing it somehow. Question is, do you think you wanna put it out? Would it ev- would it benefit you or someone else to do it? And yeah, you, you're right.
• 28:22
  Most people are probably already doing it. Yeah.
• 28:25
  It's actually a fantastic frame because I think when I speak to people who, who do want to create, but they're not really sure how to get started, they're at the blank page problem, and they think they have to be like a deep, deep expert to be able to even begin, to be able to even start.
• 28:40
  And to that I'd say like, you know, there's always someone who is one step behind you.
• 28:45
  There's always someone who is two steps behind you who would kill to have you share exactly where you are right now, because sometimes the gap between you and the actual expert, the one who's, has the deep expertise, it's so far that it's like unrelatable.
• 29:01
  So we need people at all stages of every kind of process and journey so that we can learn. Yeah. And forgetting that, I think, for me has like, I've missed opportunities- Mm...
• 29:11
  because I've forgotten that exact thing, where I really wanted to show someone like how to build a design system in Claude so all your stuff looks like yours and, but then I was like, "Oh, that's so 101."
• 29:23
  But then when I get on a call with a coworker, they're like, "Wait, how do I download the desktop app for Claude?" And I'm like, "Ugh," like I really could've started there. So yes, just do it. Totally.
• 29:34
  Okay, can we spend some time talking about Beehiiv? Yes. So I had the, um, biggest surprise when I was chatting with Beehiiv team.
• 29:43
  I do, well, I'm the biggest fan, have been doing lots of creator work and kind of partnership stuff with them, and then when I saw your name come up in community, I was like, "Wait, what have I missed?"
• 29:53
  [laughs] So like, can you take us back? What drew you in? What made you say, "Oh, that is what I wanna work on"? I guess selfishly for me, my, I, I, I'm very passionate.
• 30:04
  I care a lot about helping people connect to each other no matter where they live. There's a lot of studies, you will believe this too, like loneliness is a real thing. It's very vulnerable for people, et cetera.
• 30:15
  I mean, even Work Week, what drew me in there was, wait, we can make work a little more fun for a lot of people whose roles are very isolated? That sounds meaningful to me.
• 30:25
  And with Beehiiv, the opportunity was to do that, but for all kinds of people that are already bringing people together through their content.
• 30:35
  But now could we, like, give them the tools to help those people connect with each other? Like, selfishly, that's very exciting for me. So there was a, a moral thing there, but also the business opportunity, right?
• 30:45
  The why, why should Beehiiv do this?
• 30:47
  And it was becoming pretty clear to me as someone who had been reading Tyler's newsletter for a long time, Big Desk Energy, and just following, keeping up with Beehiiv, that they were launching all these products that to me felt very disconnected.
• 30:59
  Podcast, newsletter, this other thing, this other thing. I'm like, "Where's the home?" Like, how do we bring this all together?
• 31:04
  And again, user experience, how does someone's like, someone who's reading this creator's content keep up with all the stuff that's happening in their universe? Could it be in the form of a community?
• 31:15
  So that was the initial... I just, I, I thought there was an opportunity there, and I, I just saw it, and thankfully they were already considering it, so. And talk us through what is, what's your role?
• 31:26
  What do you get up to at Beehiiv? Yeah. The role is, technically the title is head of community. I've added another word at the end, head of community product, because Beehiiv actually already- Mm...
• 31:34
  has an amazing head of community for Beehiiv users. So head of community product, what that means is it's a new feature for Beehiiv. It is a product in and of itself.
• 31:45
  There are companies that their whole product is community, so I get to build that within the Beehiiv ecosystem. What's really fun about the role is, um, I get to kind of put my arms around the whole thing. So- Mm-hmm...
• 31:58
  what are we gonna, what, what feature are we gonna prioritize?
• 32:01
  And I actually do have direct tie with the engineering team that's building it and the designers that are designing it, and I get to make those really hard sometimes decisions of how to prioritize certain feature rollouts.
• 32:11
  But I've been a community manager for most of my career, so I feel like I understand the end user really, really well and their pain, and I also am fortunate enough to be a part of many communities as a member.
• 32:24
  So just being able to, like, connect the user experience to, wait, admin panel really, the admin controls and functionality really matters here.
• 32:32
  So both, like, understanding community management, being a community member, and then also just having ownership over this feature is fun.
• 32:42
  Another part of the role that is a little bit, I guess, not obvious is, like, the go-to market part of it. So I don't think I'm a go-to market engineer, but it's starting to happen, right?
• 32:52
  It's like, wait, how do we get people to find out about the features that we're launching? Like, what does adoption look like? I do keep track with that. What's the growth?
• 32:59
  Like, how many more people are launching a community? But it's never just about the numbers, and I get to decide what metrics matter.
• 33:05
  So one thing I kind of was pretty clear on is it doesn't matter how many communities launch. It probably matters
• 33:12
  in the first X number of days how many members did that community have, and then also what's the engagement contribution rate of those members within another time period.
• 33:23
  So the, the bar, I guess, is, is, like, quite high. We could have, I don't know, 10,000 communities launched, but if all of them have 600 members with 0% contribution, I have not done the job well.
• 33:35
  So hopefully that gives you a frame of we are, we care just as much about the success of people's communities and how it goes, not just building the feature. Yeah. I think that's so key.
• 33:45
  The metric is not just how many launch. It's like, okay, h- uh, how sustainable is... What, what i- what does this look like in one week, one month, one year? All right. Tricky question.
• 33:55
  Let's get into some, some saucy questions. Like, there, there's a lot of community products out there, so, like, why do you think that Beehiiv is, like, uniquely positioned to take this on? Oh, man. A few reasons.
• 34:07
  I think I've been at two community-focused startups, so their whole business model was a community, and neither of them are around today. So why is Beehiiv uniquely positioned?
• 34:17
  Because the creators on Beehiiv's platform, creators, publishers, even startup founders on there right now, they've already built this incredible audience. They are not starting from scratch.
• 34:27
  So they don't necessarily have to think about, "How am I gonna get more people to care about this community or want to give back to the community or build this with us?"
• 34:36
  They have an incredible, like, foundation, and now they get to architect on top of it. I think it's really, really hard to launch a community from, like, scratch. You c- It has been done. It's doable.
• 34:48
  It is just much harder. So I think it's, like, almost like a shortcut, a little gimme. Like, you guys are already doing it. You just have an amazing opportunity to build on top.
• 34:56
  So I think that's why they're uniquely positioned. The second is I think people underestimate how many tools a community manager is piecing together to provide a good experience to members.
• 35:06
  Like, I remember the days of Zapier, Airtable for the directory, like, Notion for the resource hub. Like, I've built all those things.
• 35:13
  I've done it multiple times, so I understand, like, what a community manager probably thinking about. People that are creators maybe who don't consider themselves community managers yet, like,
• 35:24
  we're trying to get them to skip that learning curve. You don't have to think about all that.
• 35:28
  We're just gonna try to build the tool where you don't feel like you need to add on another tool on top to really provide the experience. And number three, I think, is
• 35:37
  I am trying to build a little bit of an opinionated platform where we'll try to sometimes save you from yourself. So an example of this maybe is
• 35:48
  we know people want a lot of customization, but sometimes the branding colors aren't accessible. Like, they're not accessibility friendly. They don't look good on a certain device or whatever.
• 35:58
  So we'll, "Red flag, don't do it." Like, here are the options. Just, like, trust that we've thought through this a little bit. Or notifications. Like, let's by default have them all on. It's like, well, wait.
• 36:10
  If a member gets annoyed, they might unsubscribe from everything, including your newsletter, which is core to your current business model.
• 36:17
  So let's- we're gonna just launch with these many notifications to start, and then give users the control.
• 36:22
  So I think we're thinking about, you know, this product not just, like, build the feature to build the feature, add more and add more, but sometimes, like, almost restricting what we build so that the outcome for the community manager, builder, creator is actually as great as it can be without them having to become an expert in community management.
• 36:43
  Yeah, that would be, like, my next question. So, like, if I'm someone that has a newsletter, maybe it's on Beehiiv, maybe it's on Substack, maybe it's on Kit, could be anywhere, but I've got a newsletter. People love it.
• 36:54
  I've got something that exists. Who is, like, the best kind of person to opt in to then be like, "Oh, maybe I should have a community as well"?
• 37:03
  Like, should everyone with a newsletter also have a community, or what should people ask themselves in their mind before they jump in and say, "Yep, I'm gonna do the community thing"?
• 37:13
  That's a great question, and a lot of people have asked me that, so that's great, I can answer this thoughtfully. The first question I like to ask people is what are your business goals?
• 37:22
  Like, let's come back to the, the real world. People usually... If you're gonna start something new, you usually have to have an incentive to do it. Are you trying to grow your audience even more?
• 37:32
  Are you trying to monetize a new product or a stream? Are you trying to scale yourself? Like, there's usually one of those three reasons why you might want to launch. There's a fourth one, and it is purely because I,
• 37:45
  I am a natural community builder, like, I want to do this because I want to bring people together.
• 37:49
  And those people exist, too, but I'm assuming that's not the ma- the vast majority of creators who started creating content first. So if it's one of those four, like, probably a good thing to at least consider.
• 38:00
  Then I ask them, is there a through line or a thread between wh- what your audience cares about? And it can be B to B, it can be B to C. Let's take a fitness creator, for example.
• 38:12
  Is there something that's connecting all your, all your readers?
• 38:14
  But to answer that question, you usually have to take a few steps back, and you have to know your audience, and you know, you'd think, well, you'd be surprised.
• 38:21
  Like, a lot of creators are like, "I'm not actually sure, like, exactly who's reading my content. I just know that they're reading it."
• 38:27
  And it's like, well, let's start, let's go back a couple more steps and, like, launch a survey first so that when someone subscribes to your newsletter, they're getting redirected to, like, a four-question form.
• 38:36
  If they want to fill it out, great, but even if 30% fill it out, you have a little bit more of an idea. So is there something that connects all these people?
• 38:44
  The third thing I ask them is, "Are you comfortable getting off stage?" And I think that is probably the most, maybe the most important question, because for the first time maybe ever,
• 38:54
  you are not gonna be the person hitting publish or creating an opportunity for everyone else to consume.
• 39:00
  Someone else from your community might do that, and you, you just get to watch that happen, which to some, that is so exciting.
• 39:08
  To others, that is very terrifying, because their brand is so associated with whatever that creation happens with. Wait, other people can post? Yes, because that's what the community is gonna... That's community, right?
• 39:21
  Other people talking to each other without them getting value from you directly. Exciting for a lot of people, very scary for others.
• 39:27
  So are you in a place in your business, in your life right now, in your creator world where you're okay with them getting value from each other versus coming to you to get that value?
• 39:37
  And if the answer to that is yes, then all three of those things, then, like, it's time maybe to start a community and bring people together and scale yourself without you having to press publish and creating value every single time.
• 39:49
  Excellent answer.
• 39:51
  My last question on Beehiiv is, like, if I was to give you a community builder, I'm imagining, like, a wizard hat, and you get, like, a little wizard wand, and this wizard wand, when you, when you swish it, all of your community dreams come true.
• 40:07
  And then we fast-forward one year from now, what has happened on the Beehiiv platform? What is happening with the, with the people who are creating communities there? What's your wish? Okay.
• 40:19
  Um, my wish, it would be that there are so many more niche communities being launched, and not just launched, but, like, people are participating. So I would love to see, like, a big publisher have a community.
• 40:32
  Let's take a sports publisher, for example, and they have a community of people that are really into women's sports, and all of these people that have been going to Reddit or Twitter or wherever to, like, find the others who care about this, like, now feel like they have a home to go to to talk about the most exciting match of the season and feel that connection.
• 40:51
  But then there's also a gardening community where people in Cincinnati, Ohio, are talking about what's the best tomato plant for this exact specific location, and there are events happening that weren't gonna happen without this, because people have launched the communities, and the members are hosting these events.
• 41:10
  And there's a lot more intentional digital connection happening, but that translates and ripples into in-person connection, which is inevitable when you put people together in a digital space.
• 41:20
  One of the first questions people are, want to share or ask is, "I'm here. Who else is here?"
• 41:25
  Like, I wanna be able to see that turn into a lot more in-person connection, even though, yes, we're a software company, and yes, we're a digital product.
• 41:33
  But I think it can just be, like, the seed of something really cool. So I want everyone to have a fun place on the internet that they can go to that feels like they belong there, 100% belong there. Ah, I love it.
• 41:44
  Okay, I'm, uh, manifesting the, um, little, the community wizard hat for you. This has been so amazing. Is there anything that I haven't asked you that you really wish you had a chance to speak to?
• 41:56
  No, I think I've spoken to a lot of things. Maybe the last thing I'll say is just always keep shooting your shot. You are a very cool person. I think the other thing I'll say is, like, try to be someone who
• 42:09
  anyone can feel safe being themselves around. That really, really pays off in spades. Like, I think just, like, being completely non, not even judgmental, I don't know, just like, "Wait, that person is so different."
• 42:21
  Like, instead of immediately jumping to the judgment, it's like, wait, wait, that's cool. Like, why?
• 42:27
  Like, dig in a little bit more, be a little bit more curious, and I think whether you're a generalist or you believe you're a very sharp knife, quote, unquote, like, if you are a very sharp knife and you are seeing a lot of people who have all these different things, I think those people are about to be very valuable in the world and in the careers and all the things.
• 42:42
  But also, like, I bet you are also a little bit of a generalist, and it's worth just being that person that, like, tries to see the, the interesting, the curiosity part in someone else versus like, "That's different.
• 42:54
  I don't understand." I think communities let us, let us get there faster. Yeah. The world needs more of this. Alethea, you are amazing.
• 43:03
  Thank you so much for spending the last 40 minutes or so with us and sharing all of your knowledge.
• 43:09
  Um, we're gonna add all of your links so people can get in touch, and if anyone wants to come and chat anything about Beehiiv, your gals are here.
• 43:16
  We appreciate you so much at Beehiiv, and I appreciate you so much as someone who I've looked up to for so many years- Aw... um, have followed along. So thank you for building this community.
• 43:25
  I'm obsessed with it, obviously. Ah, amazing. That was so fun. This has been so good. Thank you for coming on.