Milly is runing a paid online community for generalists from a tiny Scottish island. Her group, Generalist World, has 500 paid members and she has successfully grown the business whilst far away from any tech hub.
I chatted to Milly about why generalists are the future, how to foster a real sense of community, her tips for hiring and marketing and what it's like working from a remote, Scottish island of 200 people.
Check out the interview on the High Signal podcast:
Or watch it in full on YouTube:
Here's a transcript of our chat (lightly edited so it's a quicker read)
What is Generalist World?
It's a bunch of different things. Mainly we look at them as tools, tools or community for people who have these non-linear pathes, or squiggly career is kind of the, the cool way of saying it now. Basically, people who have this very broad skillset, we help them build better careers.
And often those careers look a little bit unconventional. They haven't followed the traditional straight line. And so there's no blueprint for how to navigate that. And so we bring people together. The community was our first and main and is our core kind of product. Which has become kind of famous. It's been called a cult quite a few times, I think lovingly. I think it's a joke, but you know I guess you never really know for sure. And so, yeah, we, we have the community which is, has around 650 members now from folks all across the globe. And it is just a really wonderful pocket of the internet.
It's my favorite place to hang out. We have loads of content. We try and just like pump out as much free, valuable content as we can. So that's everything from LinkedIn to essays to tech talks to, we have a podcast keeps me on my toes and yeah, very recently we have started to move more into the education space.
So we're releasing a course and we're working with universities to kind of turn that course into more like targeted for students as well. And all around this idea. That careers are changing. You're not going to do the same career forever. It just isn't how the world works anymore, especially with AI taking over everything.
So who's preparing you for that and who teaches you how to like stack your skills and translate your value and tell your story and build that confidence. And we think we're the people to do that.
What led you to create Generalist World in the first place?
I'm a generalist but I had no language for that. I just thought I was a weirdo all-rounder for the last eight or nine years. I've been building companies, either my own or I've been like that kind of first, you know, first or second employee, very, very early on in the team.
And so I would just naturally always wore all the different hats. And again, I didn't have the language. I would just call myself like an all rounder. I didn't even care about the title. I was like, I don't care as long as I'm like doing work that lights me up and that excites me. Like I'm good. And it was when I was working my last role, I had a contract role working with a mental health tech company based in Singapore called Bravely.
And I was their 'Director of Miscellaneous' like generalist 101. That was my contractor title. And it just got me thinking like. One, what a weird title. And two, is there anyone else with a weird title like this? And like, what are they calling themselves? How do they talk? Because I had no idea. Like my CV was like, a train wreck.
I was like, I don't know how to sell that to like a traditional organization. And so, yeah, it started with a question of like, Oh, I heard this word generalist, but I'm pretty sure everyone thinks that's a bad thing. I disagree. I think it's a really good thing. I think it's like a really, really valuable skillset. What happens if I try and bring one other person or two other people or five other people. And then before you know it, you've got a network of over 60,000.
So what's it like running a business from a tiny Scottish island compared to SF or London?
One of my favorite fun facts about the island that I live on is the landmass. The size is actually a similar size to Manhattan. The difference being we have 200 people living here and Manhattan has how many millions. So I always like to laugh at.
It's all relative, right? I started generalist world on this island. And so I haven't actually known it from any other place. So it's actually just normal. And I would say that starting it from here and building it from here for the past two and a half, coming up to three years has really informed how the business runs - it has community at the heart of it.
I've learned everything about community from living in a community of 191 people. It has definitely a calm element to it. So it's definitely not the Silicon Valley hustle culture of ‘grow at all costs’.
I have my moments, you know, where I see these big meetups in New York and SF and I'm like, “Oh, hot dang, that'd be kind of cool.” Where I live, people are like, if they introduced me it's, “this is Millie and she does something on the computer.” No one has any idea, no clue what I do.
And that's fine. It definitely gives me a little bit of separation. There's definitely times when I am envious of having that connection of people really close by. But, with the internet, I open my laptop and I am like, there's too many people, if anything. I can't wait to close it at the end of the day and just go back to my peaceful, quiet life.
So if it weren't for the internet, if it weren't for LinkedIn, Twitter, we wouldn't be connecting right now, right. Then sure. It would be, it would be really, really quite isolating and quite difficult. But because I have the internet and because I have, I mean, I think it's not that far people laugh at the extent that I travel to get to my nearest cities.
What are your thoughts on having space for specialists and generalists?
I think it's essential. I think we absolutely 100 percent need specialists. Like there are times when I would like a specialist working on this with me. And in fact there's a few examples. So within Generalist World, we ironically have people who on paper are hardcore specialists.
Like they've got like their PHD, they are deep in the specialized world, yet they have self-opted into Generalist World. And for the first year, I was like, I don't understand what this is all about. And I've come to realize that being a generalist, it is a bit of an identity, but it's also just how you approach the world.
So like these deep specialists with their PhDs and they're like, you know, 10-15 years of like specialized domain expertise. It's more so about how they approach their career. Maybe they've gone from academia to tech to product to entrepreneurship. They have like, they've skipped, they've leapt. They haven't stayed on that one path.
And that's actually what makes them really special when they have all these different intersections and different like lenses to view the world. That's when they can solve really, really cool problems. So that's kind of one example. And then the other example is our team. Yeah. We have a very small team, as you said, we're bootstrapped.
So we always have to be very careful about how much money we're spending on everything, particularly on stuff. So we've got a small team of five and they are all generalists and that can actually be problematic because. Obviously we're like, sometimes you've got to go deep on things. And so how we get about that, how we get around that is our team of generalists is kind of like the foundation between us.
We have wildly broad range of skills that we can almost touch everything. And when we need a specialist. We just hire them. We just like bring them in for, sometimes it is amazing what happens when you bring a specialist in for an hour and you're like, you are, you're a top, top, top expert at this. And like, we'll pay top, top, top money for that.
Like if it, if it accelerates us, if it gets us ahead, you know, a month, two month, three month of us trying to figure it out. I'm so happy to pay for that expertise, but as a like default, we've designed the company to be the foundation as generalists. And then we just kind of tap into specialist expertise as and when we need it.
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