The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Marketing/Content, Briefly
Content, Briefly artwork

Two Community Builders Compare Notes with Milly Tamati

Content, Briefly · 2026-05-06 · 40 min

0:00--:--

Key moments - from our scoring

Substance score

64 / 100

Five dimensions, 20 points each

Insight Density12 / 20
Originality13 / 20
Guest Caliber15 / 20
Specificity & Evidence11 / 20
Conversational Craft13 / 20

Milly Tamati built Generalist World, a professional Slack community for career generalists, from a personal need - feeling like an outsider with a nonlinear "Director of Miscellaneous" career path living on a remote Scottish island. The community has grown to hundreds of members across diverse roles (professors, founders, chief of staff roles, operations professionals, content marketers) in just three and a half years, yet maintains intimate culture through intentional design choices. The conversation with host Alex covers Tamati's counterintuitive decision to switch to lifetime memberships (eliminating churn, reducing ops overhead, and deepening long-term investment) supported by sponsorship revenue and a 60,000-subscriber newsletter funnel. She scales personalization through community guides (member volunteers who onboard new cohorts), a "Calm Community" doctrine that removes always-on expectations, and member-led programs like master classes and art meetups. The episode explores how communities fail when treating members like SaaS customers or forcing top-down KPIs, and how Tamati deliberately separated her personal brand from Generalist World's identity while acknowledging their complementary relationship.

Key takeaways

  • →Lifetime membership models remove churn-driven departures and deepen member investment, but require diversified revenue (sponsorships, newsletters) to sustain operations without recurring fees.
  • →Member-led communities at scale require founders to actively let go of control, trusting hired community staff (like Eja) and community guides to shape culture rather than imposing it top-down.
  • →Personalization at scale works through asymmetric effort - 90-second personalized videos per new member, community guides from previous cohorts, and explicit cultural documents (like 'Calm Community' principles) that combine written values with human onboarding.
  • →Communities succeed by solving belonging (a core human need) rather than treating membership as a product; generalists join because they feel different and don't fit traditional boxes, not because of feature lists.
  • →Hiring and programming from within the community first (staff, master class facilitators, program hosts) deepens member bonds and creates authentic programming that outsourcing cannot replicate.

Guests

Milly Tamati

Topics in this episode

Personal brandSlack communitiesGeneralist Worldmember-led communitylifetime membership modelCalm Community doctrinecommunity guidesmaster classessponsorshipsbelonging

Questions this episode answers

Why did Milly Tamati switch Generalist World to a lifetime membership model instead of recurring subscriptions?

She felt the worst part of Generalist World was losing people who didn't renew due to life changes (job loss, busyness, becoming a parent), which felt emotionally wrong for a professional friend group. Lifetime membership increases long-term skin in the game, reduces operations overhead, and was made viable by sponsorship revenue and a 60,000-subscriber newsletter funnel that continuously brings new members.

How does Generalist World onboard hundreds of diverse members (professors, founders, chief of staff roles, operations people) without losing them to choice paralysis?

Early cohorts received one-to-one calls (unsustainable past 100 members), then switched to personalized 90-second videos from Milly or her team. Now the community uses "guides" - 10 volunteer members from previous cohorts per new cohort - who co-create onboarding and teach explicit and implicit culture (values like the 'Calm Community' doctrine plus shared vibe) for the first month.

What is the 'Calm Community' doctrine in Generalist World?

It's an early document establishing that there's no expectation to always be on, life fluctuates, and members can tap out guilt-free when needed. It's paired with programming that offers multiple connection modes (not just typing in Slack) like art meetups and master classes so different personality types can engage.

How does Generalist World manage culture and belonging at scale when most members don't know each other?

Through member-led programming (community guides, master classes taught by members, art meetups), intentional onboarding that emphasizes care and welcome, and explicit cultural values like calmness and member-first hiring. Programming creates multiple ways to connect beyond text, deepening bonds organically.

What revenue model supports Generalist World's lifetime membership?

Sponsorships from companies wanting to reach generalists, plus a personal newsletter of 60,000+ subscribers that continuously funnels new potential members, reducing dependence on churned member replacements and allowing Milly to confidently remove recurring revenue pressure.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

12 / 20

The episode contains solid foundational insights about community building - the dangers of top-down structures, the importance of member-led initiatives, and the role of personal brand in bootstrapping communities. However, much of the conversation is exploratory and iterative rather than conclusive. While Millie shares genuine learnings (lifetime membership reducing churn, personalized onboarding at scale, removing recurring ops friction), these are presented conversationally without deep structural analysis or data. The discussion meanders through jobs, AI, and generalism without extracting novel frameworks that a community builder couldn't derive themselves.

I think one of the biggest lessons I've learned, both as a founder and a community builder, is the work that you have to do on yourself to be able to let go of control.
the worst part of Generalist World was when people didn't renew... Something felt wrong in my body when I was like people just disappear from the company Slack channel, and you're like, oh, we didn't get to say goodbye.

Originality

13 / 20

Millie's lifetime membership model and member-led community philosophy are genuinely counterintuitive and differentiated from the SaaS-ified community playbook. Her insight about community not being software, the 'calm community' document, and the focus on belonging over metrics are refreshing. However, the broader conversation recycling generalist vs. specialist debates and touching AI impact without depth limit originality. The job board idea (curation for non-linear roles) is incremental rather than novel.

I think communities fail because people treat them like a SaaS. They're not a SaaS. They're not software. They're people. They're humans.
the thesis to go for a lifetime... when you make something not recurring, then people become more invested.

Guest Caliber

15 / 20

Millie is a legitimate operator with 3.5+ years building a bootstrapped, profitable community of 700+ members with diversified revenue (sponsorships, events, jobs). She has real P&L accountability and makes non-obvious business decisions (lifetime model, member hiring, member-led programming). However, she is not a massive-scale practitioner (700 members is meaningful but not huge) and lacks enterprise community experience. The conversation treats her as a peer-explorer rather than an authority, which is honest but limits guest caliber relative to someone who has scaled to 50K+ members or institutional adoption.

I personally wanted to be a part of these people's journeys forever... I love hanging out with you guys. Like, this is so fun.
my entire team that I was mentioning have all been hired from the community. It's like it's just the coolest talent pool.

Specificity & Evidence

11 / 20

The episode includes helpful specifics: 700+ members, 60K newsletter subscribers, $20/month AI cost reference, personalized videos (90 seconds each), 10 community guides per cohort, sponsorship revenue enabling the lifetime model. However, it lacks hard metrics on core outcomes: no member retention rates post-lifetime, no revenue figures, no job board conversion or placement stats, no Slack engagement metrics, and vague claims like 'a million people' saw the job board without source or definition. The conversation stays in the realm of anecdote and intuition rather than grounding claims in measurable data.

we've turned on sponsorships for the first time. If I hadn't had that sponsorship revenue, I don't think I could have felt confident enough to turn on lifetime.
it's well over a million people that have seen it now... I think it's a million people that have seen it now.

Conversational Craft

13 / 20

Alex asks thoughtful follow-ups ('Why do people join?' 'What's your hypothesis on the blockers?') and creates space for Millie to go deep. He connects her insights back to his own Superpath challenges, making it a genuine peer conversation rather than an interview. However, he rarely pushes back or challenge claims: he accepts her characterization of curated job boards as less effective without probing evidence, doesn't dig into the sustainability of member-led ops at larger scales, and doesn't press on how the lifetime model affects growth incentives. The conversation is warm and authentic but lacks the intellectual friction that would elevate it to exceptional.

I'm curious, what makes Generalist World work?
What is the blocker right now? What's your hypothesis on the blockers to that happening?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

community61generalist37world35laughs24space23first21content20different17sure16generalists15jobs15members12building11didn11feel11value10

Episode notes

Alex sits down with Milly Tamati , founder of Generalist World , to talk about community building. Less about content, more about building community (with a little behind-the-scenes about where we may be headed with Superpath Pro) Milly lives on a Scottish island with fewer than 200 people and once held the title "Director of Miscellaneous." She built Generalist World on a hunch that magic might happen when generalists got in a room. Alex sat down with her for an in-person recording in New York for her take on what makes communities work, why switching to lifetime memberships was the scariest call she's made, and what Superpath should be doing differently. This episode is sponsored by uSERP . Mention Superpath when you book your strategy call at userp.io , and they'll add five bonus high-authority link placements to your first month on top of your package. Generalist World , Milly’s community Generalist World podcast The weird jobs board Follow Milly Tamati on LinkedIn Follow Alex Hilleary on LinkedIn

Full transcript

40 min

Transcribed and scored by The B2B Podcast Index.

[gentle music] Hey everyone, Alex here. Let me tell you about uSERP. That's U-S-E-R-P.io.

If you're a growth stage or public company and SEO isn't driving enough pipeline for you yet, or maybe you've hit a growth bottleneck, you need to talk to this crew. uSERP has spent 10 years helping some of the biggest SaaS, fintech, and healthcare brands in the world turn organic search into a legitimate customer acquisition engine, and now they're doing the same for AI search. We're talking companies like monday.com, Robinhood, CrowdStrike, Wiz, Binance, and dozens more that you've heard of, from Series A all the way to publicly traded.

And the results speak for themselves. They helped monday.com go from 600,000 to 1.2 million organic visits leading into their IPO.

They built hundreds of high-authority links and content assets for Earlybird, a fintech app driving over 20,000 acquired users before Earlybird was acquired by Acorns. And they've helped Onboard rank for 13,000 more keywords in their space, tripling their organic pipeline value in a single year. What makes uSERP different is they don't just publish content and hope for the best. They engineer content assets that rank and convert, backed by links on sites like HubSpot, Gartner, and G2.

Here's the deal for Superpath. Mention Superpath when you book your strategy call at U-S-E-R-P.io and they'll add five bonus high-authority link placements to your first month on top of your package. That's uSERP.

io. Hey everyone, Alex here with a little bit of a different episode this week. We are going to be talking about community building with Millie Thomady, the founder of Generalist World, a professional global Slack community for generalists. Millie is based on a remote island in Scotland, so when I learned she was gonna be in New York for the week, I nabbed her for this in-person conversation.

So less about content marketing this week, but still I think worth a tune in for a conversation about building and managing professional Slack communities, and it also comes with some behind-the-scenes conversation about ideas I have for the future of Superpath. Hope you enjoy. Great to have you here, Millie. Welcome to New York and welcome to Content Briefly.

Thank you. I am so excited to be here. Well, I just kinda wanna jump into it. This is gonna be a fun episode on community building.

I have looked up to Generalist World for a long time, and I think it's really cool what you're doing with your space. You know, we're both community builders. I think we see a lot of communities that fail. I'm curious, what makes Generalist World work?

Mm. I think you're right. I think when I first started building community, air quotes, it was my first one. I had never built community before Generalist World in, like, the, you know, commercial sense of, like, this is the business.

And I think that actually was one of the best things that could've happened to me because I didn't come in with any, like, preconceptions or, like, notions of, like, what should a community be? I've just kind of been going off, like, instinct and, like, literally looking at my own community. I live in a very small community of less than 200 people, and kinda taking the values and the behaviors and the way that community operates and kind of putting it into the Generalist World context.

And I think why a lot of communities fail is because they actually don't begin with the why. They begin with the... Well, it depends, right? And maybe it's a product community, and it's like you begin with, "Oh, how could this community make us money?"

Or, like, a top-down kind of forcing of how can we create this, like, you know, the KPI, the metric is like, "We have to have 500 ambassadors by November." And it's like that's actually- You can't, like, strong-arm community like that. It's an emerging process. And what is the why for Generalist World?

Mm. How would you describe... And has it changed over time? It actually hasn't really changed over time.

The reason for being is because I am a hardcore generalist, have been my whole career, and have always felt like a super odd duck. Didn't know where I fit. Didn't feel like I fit anywhere. I was, like, trying to fit into different communities, and I always felt like I had to put a mask on to be like, okay, 'cause I can wear the hat of, say, content or product or founders or female founders, whatever it might be, but I was like, "I just kinda wanna be, like, me, all of it."

And so the seed was that, yeah, I was living on this very remote island. I was job searching. I eventually got a job working for a tech startup, and they gave me the role Director of Miscellaneous, which in some respects was, like, the coolest thing to ever happen, but in, in others I was like, "Oh, I feel even more alone," because I don't know anyone else who has a job title Director of Miscellaneous who lives on an island with less than 200 people. Like, where are my people?

[laughs] And so the original why for Generalist World is what happens when we bring together people who have these nonlinear squiggly paths. My hunch was that magic might happen when you get generalists in a room, and I was like, and in the worst case I might make a couple of friends. So that was kind of the why. So I think one thing that's really interesting about Generalist World is it's very bottoms-up driven, and it probably comes out of kind of what drives you there, which is, like, bringing people together and then seeing what arises from that.

You know, you're several years into this at this point. What it- We said five or six, six years? Uh, so we started in October 2022, so like- Okay... three and a half, something like that.

Three and a- Oh, wow. I have [laughs] You've grown it so much [laughs] and in such a short amount of time. That's awesome. But in that time, how have you been able, as it's grown and scaled, to kind of keep that momentum?

'Cause I think one thing I talk to other community leaders out there, and it's something I'm thinking about a lot with Superpath too, it's like we have... We're at, like, such a fun number right now of we have about 320 pro members, which is like you kinda, you know the people in that space. Mm-hmm. Obviously-Generalist world has grown a ton, and I can imagine how the energy that you brought to it initially was like, "Hey, we're just bringing friends together."

Mm-hmm. "Like, we've got this awesome group of people." Now you're at the point where I'd imagine, like, a lot of people don't know a lot of the other people in that group. How do you build the momentum to keep that going, to keep that vibe alive when you have that, the kind of scale that you've had?

Yeah. It's a science and art- Yeah... is what I'm learning, and it's been a ongoing everyday series of experiments to be able to, like, keep this culture that we've created. And so when I look back at the beginning, 2022, it was very much me in the center- Mm-hmm...

being like I'm this kind of figurehead of, like, flying this flag. People were buying into, to be honest, my, like, abstract made-up idea- Yeah... of like, "Oh, I think we need a, a space for generalists." Yeah.

And as time goes by, I was then able to hire Eja, who runs our community. The space became kind of more her shape, and now it's really funny. It is really not either of our shapes. It is truly the shape of the members.

And the best thing we've ever done, and the thing that we will continue to do for the rest of Generalist World's history, is making it member-led. Mm-hmm. And, like, truly standing by that. I think a lot of people say like, "Oh yeah, we're like member-led," but then don't give people agency.

Mm-hmm. People don't actually feel like they have pathways to be able to create the things that they wanna create. Yeah. There's...

And we were talking about this before jumping on here, but that's kind of one of my big initiatives, and Superpath is trying to make this a little bit more of a member-led community and find the pathways to let people host. And, you know, we're exploring that with our, our spaces concept, where we have different members leading Slack channels. Mm-hmm. I'm curious, as you kind of look back at the journey of going from, hey, I started this space, to, like, letting, really elevating hosts and leaders within the space.

Like, any lessons that you've learned- Mm-hmm... along that pathway about, like, what makes that work really well? Yeah. [laughs] I, I think one of the biggest lessons I've learned, both as a founder and a community builder, is the work that you have to do on yourself- Yeah...

to be able to, like, let go of control. [laughs] I think that's honestly the big thing. At the beginning, it's like you get twitchy when you're like, "Oh, okay, this is my baby and I care about it so much," and I need to let go of that control and trust that the people- Yeah... I've brought in- That's not easy.

I mean, this is a- Yeah. [laughs]... it's a brand that you built that's very much, and we haven't talked about this, but tied to your personal brand. Mm-hmm.

You have, you know, huge social following that drives the whole Generalist World brand. Mm-hmm. And so what you're saying is, like, you're turning over a lot of what has become your identity to folks that you just, like, are giving control to and saying like, "Take this brand, hold it, and do something with it," [laughs] right? Like- Yeah.

It's something that I struggle with, to be honest, that, like, the line between what's Millie Thomatias' personal brand and what's Generalist World, and where does that all link. I think one thing I'm really strong on is that I actually try and I actively try to not make it my identity. Yeah. I think at first, I remember walking...

distinctly remember this moment of walking into a meetup in Lisbon, and someone ran up to me and they were like, "Are you Generalist Millie?" And I was like, "Oh, no." [laughs] "Oh, no. We're not going there."

Like, I... And it was funny, completely funny at the time. But a- again, the work as a founder and a community builder is to be like, "No, I'm Millie." Yeah.

And, like, the community is separate and Generalist World is separate. But they are, of course, linked, and they are, of course, adjacent and complementary. And, like, Generalist World simply wouldn't exist in the way that it does if I hadn't spent all this time and, like, effort putting into building this kind of personal brand. Yeah.

That's really interesting. I wanna shift gears a little bit to talk... You've got several, like, unique structures in Generalist World. One of them is that you've got a lifetime membership.

Mm-hmm. So folks pay at the beginning, and then you introduce them to this group. You're bringing them in right now in cohorts, and you've obviously got a group where there's a lot of things going on. Could you tell me a little bit about, one, the reason for your kind of lifetime structure, how you think about that, and then two, like, how do you onboard people to this...

I mean, first off, a space that is broad in its- Mm-hmm... concept [laughs] being generalist, right? Like, that's the whole thing. Like, there's so much going on.

People are coming from different angles. Like, I think about it from a content marketer standpoint, it's a hard enough challenge- Mm-hmm... to be like, how do we introduce content marketers, who very much understand these conversations that are happening [laughs] in Slack, to what's going on here? That's a hard challenge.

But, like, you're looking at like, hey, I'm coming at it from, like, I'm an operations person that's a generalist. I'm a mark- Mm-hmm. Like, you've got all this. How do you get them into the right spaces where they get the value out of it?

So those are a couple t- different questions there. Remind me of the first question. The first question was lifetime membership. Yes.

Okay. Rationale behind that. Let's start there- Yeah... 'cause that's kind of a spicy topic.

It's not the done thing, and this is also when you, back to your original question, why do communities fail, I think communities fail because people treat them like a SaaS. Mm-hmm. Mm-hmm. They're not a SaaS.

They're not software. Yeah. They're people. They're humans.

Yeah. And the sooner you can get away from treating them like this kind of product per se, then the deeper that community's gonna be and the more real and authentic it's gonna feel. So the lifetime membership was at, probably the most terrifying decision I've made. I think that's maybe when we first connected.

It was around that time. We did. We talked around that time. Yeah.

It was around that time. I was sweating and... But it was, talk about the, like, science and the art, it was the art part of community building where I felt it in my gut that that is what we needed to do. Mm-hmm.

The reason being we'd been running for maybe, like, what, two years at that time, maybe a bit less, and the worst part of Generalist World was when people didn't renew. Mm-hmm. And there's a zillion reasons why someone might not renew. Maybe they just lost their job.

Maybe, like, life's got busy. Maybe they had a baby. Like, life happens, and it felt wrong to me, and I use that word, like, quite intentionally. Something felt wrong in my body when I was like, "All right, well-"Get out.

Yeah. And because the community of Generalist World, it is a professional community, but really it's a big group of friends. Right. That's kind of the difference.

And because there's not just one archetype, it's actually probably a marketer's worst nightmare in terms of, like, we don't even have an ICP. The ICP is, like, generalist, you know, mid to senior. We have, you know, professors in Australia, and chief of staff in San Francisco, and founders in London, and everyone in between. And so the thesis to go for a lifetime, there was kind of a few things driving it.

The first is that I personally wanted to be a part of these people's journeys forever. Mm-hmm. That sounds intense, but I was like, "I love hanging out with you guys. Like, this is so fun.

I would love just this to be my, like my network of people." So from a selfish perspective, I was like, "I would love this to be a long-term thing." And my hunch was that when you make something not recurring, then people become more invested. They can, they can invest knowing that...

'Cause you know, let's say you and I are in a community- Mm-hmm... we've become really good friends, and then for whatever reason you churn. It's kind of like when someone gets laid off and, like, then they just disappear from, like- Mm... the company Slack channel, and you're like, "Oh, we didn't get to say goodbye."

And I was like, "I kind of wanna, like, completely remove that feeling." So if you're in there, it's like skin in the game over the long term, and everyone feels the same. The second big reason was ops. Tell you what, it's much easier just to have a lifetime membership.

Like- Oh, I bet. I- [laughs] yeah. As someone with a much smaller community, the amount of time you spend doing subscription ops is- Awful... wild.

Yeah. Yes. So for me, awful. Yeah.

Yeah. I'm much more on the, like, creative, chaotic- Mm... visionary side rather than, like, the nitty-gritty ops. And I'm kind of just trying to create this, like, business and company that I really love working in.

Sure. So I'm like, "Let's, like, reduce those, like, annoying ops as much as possible." And the third reason we were able to do lifetime, and the reason I decided the moment to do lifetime when we did, is because we had turned on sponsorships- Mm-hmm... for the first time.

If I hadn't had that sponsorship revenue, I don't think I could have, like, in, you know, in a responsible manner, felt confident enough to turn on lifetime. Yeah. I mean, I think as a community manager, the scary thing about that model is just not being able to have that guaranteed revenue to be able to support your community and the, like... You know, I know how many people I can hire part-time to help out with different things because there's a predictable revenue stream in there.

It's like- Sure... you know, here's our budget every month. Yep. And, and we see that growing, and that's awesome 'cause you can reinvest it into the community.

But, like, what you're doing is saying, "Okay, each cohort we've got to- Yeah... you know, bring in this many more people, and we've got to sign this many sponsors." But that's such a cool commitment that you've made to the- And to that point-... to the space...

I'm just kind of clicking to, this is another reason that it worked, is because if we didn't have our newsletter that was growing like wildfire, there's over, I think we're coming up to 60,000 subscribers now, I again wouldn't have felt so confident to do it. Right. But it's like we have this constant growth funnel coming from my personal brand, coming from the newsletter, that's constantly bringing in new potential members. Mm-hmm.

And so if we didn't have that, I also would've felt a bit shaky going to lifetime. Mm-hmm. That makes a lot of sense. So when it comes to bringing together all these different people who are joining for, I imagine, a wide variety...

You know, they're trying to find connection- Mm... but, like, your professor in Australia- Yeah... versus your chief of staff in New York, those are very different people. How do you introduce them to the community in a way that makes sense for them?

And then how do you, like, weave together these bonds- Mm... of people that are, you know, maybe from an identity perspective they consider themselves generalists, but you know, day to day they're working on very different things? Yeah. So for the first 100 members that I welcomed, I did a one-to-one call with them, and that was really tiring by, like, the 80th call- Yeah...

or 90th call. I was like, "Oh, my gosh." So that wasn't sustainable, but it was incredibly valuable. I got so much information about why someone is joining- Mm-hmm...

who these people are. For the next, say, 600 members- Why do people join? What's like... What was the biggest- Yeah.

I think why people join, the kind of the crux of it, is that because they feel really different. Mm-hmm. They feel really different. They feel like they don't actually belong anywhere.

They don't fit into any of the traditional boxes. And I think one of the things that community can really solve is, like, one of the oldest human feelings ever, and that's belonging. And I think belonging gets, like, thrown around a lot, but I think at our core, I know I can speak for myself, at my core, of course I wanna belong. Mm-hmm.

I wanna be a part of my group. I wanna be a part of my people. Because when I belong, that's when everything else unlocks. Mm-hmm.

Mm-hmm. So bringing these people together. Yes. Yes.

So the first hundred was a one-to-one. The next kind of 5 or 600 I kind of switched to an async- Mm... where I would just send people personalized videos, and it was amazing how much people appreciated that. Yeah.

Like, it would take me 90 seconds per video. I would sometimes do, you know, 100 videos plus per cohort, so it would still be- That's wild... pretty hardcore. And people would be like, "I can't believe this is not AI."

And now my team is sending the videos. So any time that there is an opportunity for us to do something that doesn't scale and that is personalized, I'm like, "Let's do that." Mm-hmm. Let's do that.

There's a few core things that I think make Generalist World really different, and particularly in the onboarding people feel that, is in those personalized videos, whether it's me or one of my team doing it, I'm like, "We need to talk about the calm community doc." Mm-hmm. It was the first, like, maybe one of the first five documents I ever wrote for Generalist World. And again, coming back to just, like, how do I wanna live?

Like, what is the space that I wanna create? I wrote this calm community document where it's like, "We are a calm community." What the heck does that mean? It means things like there is no expectation that you should always be on.

Like, I understand- Mm-hmm... that life fluctuates.When you need us, we're here. If you need to tap out for a bit, that's also okay.

So it's kind of these, like, principles of how to create a calm space. And now with our onboarding, because we a- are at a scale where it's just beyond what me and my very small team can do, we bring in community guides every cohort. So these are kinda like OG members. To be fair, not even OG.

Sometimes they were members from the previous cohort. Mm-hmm. And we'll ask, yeah, usually around 10 members, and we're like, "Do you wanna be a guide?" And the response is always just, like, the most heartwarming thing ever.

They're like, "What an honor." Like, "I would love to be a guide." And so for the first month, we all work together to be like, how do we create this space, and how do we introduce people and invite people into the space that we all love and we all value? And we can kinda teach them the culture.

And often the, a lot of the culture, some of it's written down- Mm-hmm... and is very explicit, but a lot of it isn't. A lot of it is just, like, a feeling. Yeah.

Little bit of, like, shared history and vibe- Mm-hmm... and yeah, that kinda thing. So having a, like... Not just being like, "Here's our culture.

Here is, like, the lore of our community [laughs] written down." Totally. That'd be like, not give the same impression as, like, an actual human, like, introducing you. [laughs] Yeah.

Totally. Yeah. And, like, think about it, right? Like, if I was to arrive in a community, and there's 10 people from that community who are, like, putting their hands up to welcome me, I'd be like, "Huh."

Like,, "They really care." So it's like a culture of calmness, but a also a deep culture of care. Mm-hmm. Switching gears a little bit to, like, the community product itself- Mm-hmm...

and, and the different programs that you run. So we've talked about, like, you have very member-led community. People propose things all the time. They're running things all over the place.

What is something that you're really excited about right now, a program that is either you're leading or a community member is leading right now that's going really well? Yeah. I think the... is probably our master classes is a really simple example, where for the first, like, two or three years, I overcomplicated it within an inch of its life- [laughs]...

where I was going and getting these external facilitators and paying these external facilitators. And then we were like, hang on, we have, like, the coolest talent- Mm-hmm... the most smart and interesting people right here within Generalist World. What if we just paid them?

Mm-hmm. And so now our, again, one of our values and our kinda core thesis is if we need to hire, we always look to the community first. Mm. And so my entire team that I was mentioning have all been hired from the community.

It's like it's just the coolest talent pool. And then same now with the master classes. And the master classes have a double-edged benefit in that the... Well, our members get paid, so great.

That's awesome. Love that. But then it's also a way for them to connect with other people in the community, so it, like, deepens bonds and... 'Cause I think when you have, you know, hundreds of thousands of people in a community, it is really hard to be like- Mm-hmm...

how do you make this space where people can actually genuinely connect? Not everyone is a typer. Mm-hmm. A lot of people aren't typers.

Mm-hmm. They don't wanna read, like, long walls of text. So a lot of our programming is having, like, a smorgasbord of ways that people can connect, like- Yeah... another example is one of our members was...

Yeah, he's, like, really into art and crafts. And so every Friday now, he's hosting, like, an art meetup, and anyone who's into that. And, like, it might be people who don't wanna go and, you know, interact in the AI or no-code or marketing kind of one, but they love art. Mm-hmm.

And they're like, "Actually, that could be how I find my way in." And I've seen this time and time again. You just need to give people a way in, and then they, then they can deepen into the community. I don't think you can force it.

Mm-hmm. Yeah, and I think that's kind of been one of these threads here, is talking about your ability to turn things over to the community and not try to, like, enforce this kinda top-down structure- Yeah... from yourself. How do you deal with the fact that you've got a global...

This is something that we've talked a lot about in Superpath, is like, we've got a global audience also. You're obviously doing in real life things now. You are doing live events. I think one of the things that we talk about, like, how can we better support folks in other time zones?

Like, we're probably 60% North American. It's just enough to be, like, hard to justify doing some of our live events in other time zones, but wanna find ways to support those folks. How do you manage this, like, you know, if you're investing more in real life things? And I know while you're here in New York, you're doing a whole lot of in real life events, and I'd imagine people in other cities are like, "You know, I wish she could do that," kind of like, "Come to my city- Totally...

and do this," sort of thing. How do you think about, like, how to support programs that serve a global audience? Yeah. And obviously, this is, like, you being in, in Scotland [laughs] and on a remote island, like, I'm sure very top of mind for you all the time.

Totally. I remember maybe, like, six months or a year into Generalist World having this, like, kind of regret that I didn't just start in one place. Mm-hmm. Because global is just hard.

Yes. Really, really, really hard to get right and to make everyone feel included. And because we're, you know, bootstrap, self-funded, I didn't have budget to be going and, like- Right... growing and hiring people all over the world.

So that was probably me six months in having a little panic of, like, "Oh, my gosh, how do I, like, accommodate and invite- Right... people into this?" Now we've kinda ridden the wave, and the, the audience is big enough that it's okay. And I think, again, like, it always comes back to member-led.

Mm-hmm. So you don't need that many people in a place to have the con- You just need a few, like, really effective, really excited, effective and excited members in that place to get something started there. Mm-hmm. What's something that you're really excited about right now generally as you look forward to, like, the next year of Generalist World- Yeah...

um, across anything that you're doing in the community? Yeah. I think one of the things I'm excited about is this piece of the puzzle which you and I connected on about a year ago, that I've, like, always been kind of dipping my toe in but never quite diving into the full pool of it, which is around jobs and recruitment. So, like, our bread and butter is community content events.

That is what we're known for. That is what we do so well. But this kinda missing piece of the puzzle has always been, like, okay, and then?How do we get more generalists making a fantastic living?

Okay, this is great because we haven't talked about this before, but this is- Yeah... a space that I'm thinking about a lot right now too. Yeah. So I'm excited to hear what you have to say about it.

So- You launched this new job board, right? Like- Yeah. This is- Uh, yeah... what this is...

So, like, I have avoided the job board, like, I don't know, world, like the plague, because I was convinced that they didn't work for generalists. Yeah. I was like, I think for the generalists, like, most people I know get jobs through network, they get jobs through- Right... warm...

The job gets created for them. Yeah. They don't, they didn't exist before. And I'll jump in with my context here too.

Yeah. So, like, I ran... So in my previous community, people operations job board, a curated job, like, exactly what you see all the time, right? Yeah.

And I think we were a little bit early to it, and that worked out in a great way, and that became, like, a huge source of, like, our newsletter signups and, you know, we spent some extra time on it making sure it was really good. We've obviously, in Superpath, also had a history of having a curated job board. There's a lot of those out there right now. Mm-hmm.

And as we rethink about our job board for Superpath, I'm kind of facing the same thing, where I'm like, first off, I don't think curated job boards are as effective as they were even three or four years ago. Sure. Because you have, you know, this crazy AI world where it's a messed up recruiting process. And people, you know, you talk to anybody that's actually looking for a job and they say, "Hey, like, if I don't get to this job in four hours, then it's useless."

Sure. And what's really helpful is these in-network connections. And so, as I think about this, I'm like, "I don't know if building a curated job board again is the right move." And so- Sure...

with that context, very excited to hear- Uh-huh... what you're learning along the way here. Yeah. And I agree.

This is a question that I'm playing in at the moment. So I guess to give the context, we have a newsletter. Mm-hmm. We send it twice a week.

On Fridays, it's a podcast at the Generalist World Pod. Check it out. And on Tuesdays, it's the job opportunities. And so the job opportunities newsletter has been going since, like, the beginning of GW, and it's just, like, 40 to 50 jobs- Mm-hmm...

that I find anywhere. Twitter, LinkedIn, like... And they're always a bit, they're generalist jobs. Yeah.

Um, and I've trained my algorithm to feed them to me- Mm-hmm... because I, I comment on every single one. And people are like, "Where are you finding these?" I'm like, "LinkedIn- [laughs] "...

just gives them to me now." Yeah. So it's funny, because it's one of those things that has been in front of me the whole time. But we spend all this time each week, you know, many hours curating and making this job newsletter really beautiful.

And I was like, "Huh, what if I just, like, made a version of it that's public?" Mm-hmm. Like, so we just have one database. Mm-hmm.

One goes to the newsletter, one goes to this job board. And I was in New Zealand. I'm from New Zealand, and I was at home over, like, December, January, February, and just, like, a Saturday morning and I was like, "Oh, Claude Code, like, it'd be kinda cool if, like, that could, like, build the job." I'm non-technical.

Mm-hmm. So it kinda seemed like a far off thing. And I was like, "Oh, but what kind of job board would it be?" I was like, it's just a job board for weird jobs.

Mm-hmm. And this is one of the many experiments of Generalist World, and this one went insane. Yeah. It went completely bananas.

I think it's well over a million people that have seen it now. And what this tells me is from the talent side- Mm-hmm... people are screaming out for jobs that are not so narrow, that are not so rigid, that are not putting them into this, like, box where they can't- Mm-hmm... be creative with.

And the gap that I'm seeing is organizations. I just wanna shake them. [laughs] Because I don't think it's in anyone's best interest. Sure, some jobs need to be highly specialized, and- Right...

that's awesome. We know how to do that. Right. That's not a problem.

The real opportunity that I think organizations are missing out on is that the world of work and online and- Mm-hmm... knowledge work is changing so fast, that when you can have people who come in and have these more fluid roles- Mm-hmm... and can, like, connect dots across teams and- Yeah... have more agency to, like, be the creators or the innovators, that's when you're really gonna be able to stay ahead of the curve.

Yeah. So the... What I'm hearing is, like, the problem that you think you're solving here is that you're connecting, like, generalists don't have a good way to find jobs that fit generalists. Like, unlike if I'm a content marketer, I'm searching con- Sure...

it's like, I mean, you can... I can search content marketing manager as well as you can [laughs] on LinkedIn. Sure. Right?

And so it's like, what value am I providing there? But your ability to curate these, like, jobs that are truly hiring for generalists- Mm-hmm... is solving that pain point of I'm a generalist, I want a job that allows me to, like, flex those things and doesn't force me into this. Yeah.

You are actually going out and finding those. Yeah. So the curation, I feel like that's actually the difference, where it's like if I'm curating content marketing jobs, it's like what value are we actually adding here versus, like, that is actually legitimately the problem to solve with your community. Yeah.

Yeah. That's a really interesting difference. And when I, like, as some of the examples of the jobs that I'm seeing, and I know I was just bagging on organizations not being, like, having these flexible jobs, but I am seeing every week more jobs being posted. And the keywords are kind of, like, unorthodox, non-linear.

Non-traditional is now- Yeah... the new, it's, like, the new thing people are looking for, these non-traditional paths. And, like, Stripe came out with this amazing one that they wanted. They called it, like, an unorthodox writer.

Mm-hmm. And they specifically in the job description were like, "We don't want someone that fits in a box. We want..." And I was like, oh, goody, like, we're moving in this direction.

Well, I have to imagine it's a really... Like, and we haven't... Somehow we've gone through this with barely talking about AI. Yeah.

[laughs] In any way, which is great, but, you know, I think you've mentioned Claude Code once, but, like, actually wild that we've made it this far. But I'd imagine that, I mean, something that we're seeing on our side, like, I'm working with content marketers, like, there's a lot of, like, we had a very-... clear, defined job for 15 years for- Mm... a content marketer, and that's changing overnight.

And like the jobs that we're seeing, I would say are probably more generalist or like more let's take a step back. Like- Yeah... what is a content marketer? Mm-hmm.

What does it mean to like build these content systems? I imagine that's gotta be a pretty good moment for generalists generally, like [laughs] Generalists generally. Generalists generally. [laughs] Say that 10 times fast.

I think so. Yeah. Like I think when I started GW a few years ago, it certainly was not as accepted or sexy- Yeah... to be like, "I have a non-linear path.

I don't fit in a box." It's like, "Oh, what's wrong with you?" Right. Like, no, you gotta climb the ladder.

You have to like squeeze yourself and what do you do? Right. Tell me what you do. Give me a two-word answer.

What I do think, and I am aware of my own bias and my own bubble, that it is changing, and I think the big... There was two big kind of crux moments, and the first one was COVID. Mm-hmm. Where everyone started questioning, "What the heck am I doing with my life?"

Right, right. And the second one is obviously AI. Right. When we're like, "Oh, I have 10,000 PhD level specialists in my pocket- Mm-hmm...

and it costs me $20 a month. Oh, what does that mean for how I work?" Mm-hmm. Yeah.

That's what... I mean, and this is like what we're seeing in our community as well is like we see a bigger movement towards generalism. Like we've got, you know, these content marketers that have, you know, backgrounds in writing and editing and content strategy, SEO, and it's interesting like even the people that are, you know, have stayed at the same company are being asked to do more generalist things. Mm.

And it's like now you've gotta be like figure out how to like wrangle AI building with these different tools, and also like even, even mediums. I mean, we're seeing... We have a community of a bunch of writers who are now being asked to do podcasts and video and- Soir... expand.

And I just think even from my perspective like it's a- Yeah... very cool time for generalists. I think it's al- also worth saying if you're a specialist listening, if you've spent- Yeah... like you know, 15, 20, 25 years of your life getting amazing at one thing, it's not the end of the road for you.

Because what a specialism, what an expertise can do is it can amplify the rest of your work. Yeah. I think, I think the danger is when you get so stuck in that box- Right... that you're not like, can't put your eyes up and see, oh, okay, like how, what else could I do here?

So I think if you have these expertise, if you have these specialisms, you're actually still in a great position- Yeah... um, if you can then also lean into the human skills, like adaptability, creativity- Totally... innovation- Yeah... all of these.

Judgment, discernment. So it's like, yeah, I mean, if I had a dollar- Mm-hmm... for every time someone pulled the specialist versus generalist- Yeah... argument on me, I'd have many, many dollars.

And my stance has always been the same, and that's like we need specialists. Yeah. And in fact, ironically, we have loads of specialists inside generalist world. Yeah.

Make it make sense. Which is why the ICP is always just like such a hard one to nail down. But like even myself right now, I'm specializing in community building. Mm-hmm.

100%. I'm spending all my days for the last four years becoming pretty damn good at it. Yes. But the reason that I still hardcore resonate with the generalism is 'cause maybe I'm not gonna do that forever.

Right. Right. It's for like a season. It's like a spike.

Yeah. I'm gonna like go really, really deep in community building, and I'll pop up. It's like then I became a, quote unquote, creator. And I was like, that wasn't part of the plan.

Right. Like, that's just a spike that has emerged. I resonate with that so much. Like that's, you know, my own career path is like I have specialized in different things at different points in my life.

Sure. And it is not a cohesive story. I'm like- Sure... broadly I've done go to market things, like sitting as a co-founder, like going really deep in the like HR tech People Ops world.

Yeah. Now in marketing, like- Sure... done sales. I've like, you know, just done like everything, and it's like in the given moment, like right now, similar to you, I'm thinking like I'm specializing in community building and running a small business.

Like that- Sure... is my focus. But like that might not be 10 years from now, [laughs] right? It probably won't be.

And that's very exciting to like have that space where you're full of other people like that. That's really cool. I wanna ask you a question here at the end of we've talked about both of our communities, so both on air and off air. [laughs] Do you have any advice for Superpath and what you think that- Mm...

we should be doing? Mm. Well, let me ask you this. What is your why?

I think our why right now for Superpath, and this is one of the early things I was trying to figure out as I jumped into this business six months ago, is, you know, why, if people join this, like what are we trying to accomplish here? And I think the big thing for our space is navigating the world of content marketing and careers in content marketing as it evolves rapidly right now, and making sure you're staying ahead and supporting each other. So it's a little bit of, you know, feeling like you've got a team of people- Mm...

who are also navigating this same like challenging environment with you, like staying ahead- Mm-hmm... um, and just like supporting each other. So, you know, for me personally, it's about I, I love just being able to work on a community product where the goal is to bring people together- Mm-hmm... uh, and like- Totally...

bring closeness. Like it, it comes from that same place. I think we have a maybe a bit of a more defined mission around like this moment in- Sure... AI and how it's changing this industry, and how we kind of continue to stay ahead.

So those are the big things that- Mm-hmm... I'm thinking about for this community. And so it's like how do I build the programs, how do I build this space to better deliver on the results of people feeling like they've got their people and that they're working ahead? And next question, so I get really good context, is what is the blocker right now?

What's your hypothesis on the blockers to that happening? Well, I'd say like, first off, I think-There are a lot of things that are going really well. We're growing, and I think we're delivering a, a really solid product. I think a few blockers, I mean, one is just, you know, resources constraints.

Mm-hmm. There's always, like, so much, and we talked a good bit about this, but so much I wanna be working on. Yeah. And you know, I'm...

Got an awesome team of contractors, but I'm also the only full-time person. There's only so much- I get it. [laughs]... I can do there.

And then also bringing new people into the space, I think we've also talked a lot about the energy that you've got in Generalist World, and I think we've got a space that's been around six years, and we kind of have people that understand it, that get it, they get a lot of value out of it. But really bringing new people into that space- Mm-hmm... and hitting them with the energy, that they feel the value- Mm... out of the gate, and, like, delivering on that value, I'd say that's probably a blocker for us- Okay, so two-...

right now. Yeah... two advice- Yeah... advices to begin.

The first is do less but better- Yeah... which is the advice I wish someone had shook me with at the beginning. And we were saying just as we walked into this co-working that, like, I mean, it's a blessing and a curse to have minds like ours. I think we kinda see the world quite similarly, where it's just like, "Opportunity."

Like, all the things we can do. And often... Well, what I found, it's a hard lesson I keep learning, is that it's often the obvious thing. Mm-hmm.

It's like I keep going in this full circle, and then I come back, and I'm like, "Oh, it's bringing generalists together. It's what I thought at day one." So they're kinda, uh, some things... And in terms of, like, bringing new people in, one of my favorite past times is to check.

So when a new member comes in, I will go and click on Beehiiv, and I will see how many emails that person has received. Sometimes it's hundreds. Sometimes it is hundreds of emails before they're like, "Aha, yes." Mm-hmm.

And so there is real value in being able to, like, step back and take the long-term view. Right. And be like, "Okay, community, it's not a SaaS." People take a long time to be like, "Is this the place for me?"

Right. And being, like, patient, being patient, that- Mm-hmm... to really attract the people that you want to attract and have them trust that this is the right space for them, it takes time to build. Yeah.

I think the other big thing I'm gonna take away from our conversations is, like, being more comfortable letting go of the structure and, like, handing- Mm... things over to the community. I think that's something that's, like, very scary, but I think that has, you know, as we've talked about, it been so much of the success recipe for you, is that everybody feels ownership over the community, and it's not- Yeah... your community and your structures, but it really is a communal effort to create and maintain the space.

Yeah. I think what Generalist World does very, very well is we create these shared values. And so as long as everyone is aligned on those, like, shared values, what the actual thing is, the, the how of how you get there, the actual programming, the actual events, whatever it might be, is neither here nor there, really. It's like as long as you have that underlying deep value alignment, the rest kind of takes care of itself.

Mm-hmm. Millie, thank you for coming on. Where can people find you? They can find me LinkedIn.

I'll be posting there every day. TikTok, Instagram, everywhere. Millie Thomady, I'm the only one. Awesome.

We'll share that in the show notes. Thanks so much. Thank you so much, Millie. Thanks, Alex.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • How to Build a Successful Paid Community with Jay ClouseGrowth In Reverse: Newsletter & Email Growth · on Slack communities87 / 100
  • From rep at ADP to CRO at Houzz with Tara Di-Cristo-SchmittOutbound Squad · on Personal brand69 / 100
  • Episode 95: Community as a Catalyst for Business GrowthTwinning Strategy · on sponsorships61 / 100
  • 996: What Will You Be Known For (That AI Can’t Replace) | Leadership StrategiesShameless Leadership · on Personal brand39 / 100
  • The Challenges a New Leader FacesTHE HR & LEADERSHIP PODCAST · on Personal brand34 / 100
  • Knowing When a Chapter Is Ending (Pausing this Podcast)Content Inc. - The Podcast · on Personal brand31 / 100

More from Content, Briefly

All episodes →
  • Beyond the Blog: B2B “research” is costing you your credibility with Tanaaz Khan71 / 100
  • We Are Worth More Than Our .md Files77 / 100
  • Brand mentions, backlinks, and AI search with Gordon Meagher85 / 100
  • Content Marketing from a Blank Canvas64 / 100
  • Be the one who actually cares about content75 / 100
Explore the best B2B Marketing podcasts →
All Content, Briefly episodes →