Milly Tamati has built one of the most impressive businesses built off the back of a newsletter that I’ve seen in a while.
After realizing the typical “job” roles didn’t match her experience and skills, she took it upon herself to create a community for people with squiggly careers.
And she’s built a multi-6-figure business in just 3.5 years, growing the Generalist World newsletter to over 40,000 subscribers.
How Milly Makes Money
Let’s dig into how Milly is earning money at this point, because an audience without revenue isn’t as exciting, is it?
Generalist World Community
Milly’s main product is the Generalist World community. It’s a robust Slack group with over 700 members who all identify as “generalists.”
In the early days, this was a freemium community, where you could access some of the community for free, or pay $99 for the year and get full access.
The community now costs a one-time fee of $950, and they open the doors to the community 3-4 times per year, adding around 100+ folks each time.
Their latest cohort brought in 120 members. At $950, that’s $114,000 from just that one cohort.
If you run that playbook 3 times a year, that’s $342k from the community alone.
Digital Products
Aside from the community, Milly and the team also sell 2 standalone products:
- The Positioning Guidebook (currently $50)
- Unboxed, which is a self-paced course (currently $275)
When you join the community, you get access to both of these as well, so it’s a nice first step for people to get into her ecosystem.
These are great upsells for people who sign up via her quiz, which we’ll get to in a bit.
Sponsorships
Since changing the community to be a lifetime acccess model, she’s decided to lean more into sponsorships and brand deals to fund the business.
Some of the recent brand partnerships she’s done have been with
Speaking
Milly has leaned in pretty hard to the speaking scene lately, something she’s been wanting to do for a while. This does bring in revenue, although it can be up and down.
Aside from bringing in revenue, speaking helps with brand awareness, building relationships, and
Other Revenue Streams
I did find some other revenue streams for the Generalist World, including:
- Milly being an advisor for a company call XIR
- Selling their own merch
- Affiliate marketing
- An upcoming book that’s being written
There might be a few others as well, but those were the main ones.
The Growth Timeline
The growth timeline with the Generalist World is one of my favorites. It’s proof of just how important building a sustainable foundation is before trying to “go viral” and have super fast growth.
It kind of reminds me of Packy McCormick, who was building his newsletter for over a year before cracking 1,000 subscribers. Now he’s grown to over 250k subscribers.
Similarly, Milly was building for 2 years before she hit 15k subscribers. And then in the last 8 months has exploded to over 40k subscribers using what she calls the “Elite newsletter flywheel.”
The Growth Levers of Generalist World
I think this deep dive could go on and on and on, because Milly has done and tried so many fun ways to grow her newsletter. But, I’d tried to pare them down to the most important, or the ones I think had immediate or lasting impact.
🔄 1. The “Elite” flywheel for newsletter growth. This one is juicy! It’s how Milly was able to add 27k email subscribers in just 8 months, after it taking over 2 years to hit her first 15k.
🛡️ 2. Building a defensible personal brand. This makes everything else work better. Milly leans hard into building a personal brand and why she thinks every founder should as well.
👷♀️ 3. Build in public. The days of building in public are far from over, and Milly shows us some great examples of how you can turn this into sponsorships and brand deals as well.
🧪 4. Experimentation. The name of the game with newsletters. Experimentation is one of the biggest pieces to Milly’s success building out her newsletter and community.
The Generalist World brand got started when Milly started to realize that some people had to have “squiggly” career paths like hers, but she didn’t know a ton of them. That’s when she turned to LinkedIn and started browsing around to find people who had similar journeys.
She started DMing people there to chat about this idea, and had around ten 1-on-1 conversations going. Over time it started to become too much, so she popped everyone into a Slack group and that really helped things take shape.
Instead of Milly having all of these conversations with the other person, they could now have conversations with one another as well.
And even though she didn’t realize it at the time, that was the start of a community that now has over 700 paying members, from dozens of countries, and became the start of a big piece of her life’s work.
But let’s get into how she grew that community and newsletter to over 40k email subscribers, and multiple 6-figures in revenue.
1. The “Elite Flywheel” for Newsletter Growth 🔄
This growth lever has been, by far, the most impactful on the growth of her newsletter. It’s generated over 30,000 new subscribers since its inception in 2024.
And 27,000 of those have some in the last 6 months.
It’s called the Generalist Quiz, and it all came about because Milly kept getting the same questions over and over from her audience: “I think I’m a Generalist, but I don’t really know if I am,” or “What kind of generalist am I?”
Milly decided to experiment and find a way to help solve this problem. She felt like there were 4 specific types of generalists, and knew this could naturally be super helpful for people as a quiz.
But doing quizzes well can be tough. So when a community member of hers named Ramiro, offered to help, she jumped at the chance. Ramiro is an organizational psychologist, a person with great experience figuring out how these things can look.
He spent time figuring out the logic and what questions would be best to ask her audience to determine which kind of generalist they are.
He built the quiz using a tool called ScoreApp, and Milly made the brilliant move of putting the quiz on a separate domain, generalistquiz.com.
Now, she uses this as her one and only lead magnet. It’s the link she shares everywhere. It’s in all of her social bios:
And she calls it out in videos, on podcasts, and whereever she can.
Milly launched the quiz in July 2024, and by July 2025 when she came into the GIR Pro community, the quiz had brought in 15,000 net new subscribers.
I say net new, because some of her current subscribers had already taken the quiz, so the overall number was around 23k, but 15k were new.
A Quick Note
Milly came into Growth In Reverse Pro earlier this year to share her strategy and talk about how others can do this as well. Including showing the backend of her TikTok analytics account, how she thought about the questions in the quiz, and much more. Milly is a gem.
This is just one of the recordings you get when you hop into GIR Pro – come join us!
And now, just 4 months later, the quiz has brought in over 30,000 subscribers.
For free. With zero ad spend. Okay, so how did she do that?
Now, Pair it With TikTok
Once Milly had this brilliant quiz that she created…she needed to find a way to promote it. Naturally, she went to TikTok.
I’m joking, that’s probably the last place I’d go. Except that I’ve also written a deep dive into Tori Dunlap, who’s had over a million people take her quiz, which she shares all the time on TikTok and Instagram.
At first, the growth was a little slower. But more recently, Milly has definitely hit her stride. She recently had a single video that added over 3,600 subscribers by itself.
1 video, 3,668 subscribers. Are you listening, yet? 🙂
Yes, go ahead and cringe, I did too for a while. But then I started digging in and realizing that these aren’t overprepared videos or really professional-looking. In reality, those things apparently hurt the performance of a TikTok video.
Take a look at some of the more recent videos she’s posted:
What do I see? Blurry screens, imperfect hair, just real-ness coming from all of these videos.
As a perfectionist, I love to see this. Because it means you can win, and probably have a better chance at winning, when you’re focused more on the message than how you look or how dirty your computer screen is.
Sure, it wasn’t like she posted one video and had a huge success on her hands. She’s posted 192 TikTok videos over the last 2 years.
But it wasn’t until her Generalist Quiz was built that she really started getting a meaningful amount of email subscribers from TikTok.
The Custom Domain
I’ve seen a lot of people using the quiz strategy, and it’s been pretty effective. But I can’t help but shake this realization that one of the reasons it’s worked so well is that she gave it its own domain.
This is extremely powerful for branding.
She’s able to show you the website in the video with the URL on screen, and say “go to generalistquiz.com” as reinforcement of where you can find the quiz.
It’s not like generalist.world/quiz, that redirects to another page – it’s generalistquiz.com. It definitely rolls off the tongue much more easily.
Plus, it’s a .com domain, which makes my marketing heart so happy.
If you’re going to go this route, I’d highly recommend buying a domain for ~$12 as it will be much more impactful, especially if you’re sharing it in videos or on podcasts.
Insanely Valuable Quiz
One of the other things that has led to so much success with this quiz is just how insanely valuable it is.
She said, “I think the world it’s drowning in actually not useful lead magnets.”
After people get their quiz results, they say things like “it’s spooky how accurate this is” or “wow, this is giving me language about who I am.” When you can hit on something that is so powerful people say things like that about it, you know you’re onto something.
And the best part of making an insanely valuable quiz, is that the results are so useful people are going to share it with others. That’s what really helps the flywheel keep spinning even when you’re not creating TikTok videos.
2. Build a “Defensible Personal Brand” 🛡️
Milly has a very professional view of using social media. While a lot of us (myself included) grumble about it, she sees it as a non-negotiable based on the kind of work she’s doing.
So much so that I think she’s convinced herself to love the process. 🙂
It’s going to be very hard to be a professional content creator without using these free tools that can help you grow your audience and drive email subscribers. Here is how she uses each platform.
She even lists this topic as one of the 4 things she loves talking about most:
Posting for 1,000 days in a row
Since she started the newsletter, Milly has posted on social media every day for more than 1,000 days. That’s a lot of posting.
And the best part? She has never scheduled a post on social media.
Buliding a defensible brand is something she knows it’s extremely important.
Why? Because she said every day people are getting laid off, and a personal brand is something people can’t take away from you. They can’t take away the followers, nor the relationships that having a personal brand helps you build.
It doesn’t hurt that she lives on a remote island that has a population of 171. She needs some sort of social outlet because of that.
TikTok
Milly uses TikTok as a place for experimentation. She admits that TikTok has ZERO loyalty for creators. A follower there is a true vanity metric because those people are not necessarily those who will see and continue to interact with your content.
She also said that while other platforms like LinkedIn will drive sales, TikTok will drive practically nothing. However, it’s a great place to get subscribers.
But this also means it’s a great place to experiment with short-form video, and see what’s working and resonating with her ideal subscriber.
The other benefit of creating short form videos? She said, “If I’m ever trying to market something, if I can’t turn it into a TikTok video, I don’t have the idea down. I don’t have my messaging or the positioning down.”
While it started as the place she was using to DM other people who had squiggly career paths, it turned into a place where she was bringing in email subscribers.
Some ways she says she’s grown her account to over 20k followers is through building in public. She says that 75% of her posts are about the company she’s building as she is building it. That keeps the audience in the plot of the story, vs seeing themselves as an outsider.
She noted that this builds deep trust – which makes sense. People want to feel part of something, so why not let them in?
As I mentioned, 75% of her posts are about the journey. The other 25% are a mix of selling something, posts aimed at getting engagement, or sponsored posts.
She feels like LinkedIn followers are like a larger group of friends. Whereas Tiktok has zero loyalty.
More recently, Milly realized that she had built up an audience of over 7,000 followers on Instagram without really trying. She was cross-posting her TikTok videos, but not really engaging or trying to build an audience over there.
Pretty cool.
She realized in the last few months that she might want to try and put some effort into building there, to help diversify social platforms even more. And maybe people on Instagram are a little more loyal than TikTok 🙂
3. Building in Public 👷♀️
Milly has never shied away from building this brand in public. From day one, she’s been posting about growth, what she’s working on, who she’s working with, and so much more.
The tweet above is from just a few months into this journey of building Generalist World. And you can see she’s already sharing numbers and being as transparent as possible.
This kind of thing brings people along for the ride, instead of you just shouting at them.
Or like this where she’s asking people to vote on what she should do to celebrate a specific growth milestone with the newsletter:
She’s just having fun with all of it and sharing progress along the way.
Relentless Tagging
Milly is very good about shamelessly tagging brands and software tools she’s using.
If Milly is talking about her newsletter, she tags Beehiiv. If she is talking about the quiz, she’ll tag ScoreApp and Zapier (the automation tool that links ScoreApp with Beehiiv).
This might seem like a small thing, but it leads to the social teams at those brands to end up engaging with the post, and getting their attention.
This helps a lot when you’re trying to start doing more sponsorships with these companies, as Milly is. When they see you already talking about them for free, they’re going to be more likely to think of you favorably when it comes time to spend sponsor money.
Be an Active Community Member
If you’re familiar with the Hustle newsletter, you’ve probably heard of their Trends community – or at least what it used to be.
Trends was an incredible place to go for business and startup ideas, share insights, and just have fun as a “nerdy” entrepreneur type person.
Well, I did some digging and found out that Milly was part of this community and was pretty active in there. She shared multiple business ideas from 2020 to 2022, when she finally shared about Generalist World in the Facebook group.
She also went ahead and posted this in the Entrepreneur Reddit community.
And she included a link to her stuff on Reddit – bold move Milly! 🙂
4. Experimentation 🧪
Alongside the build in public method, I found a number of fun experiments Milly has tried over the last 3-4 years while growing GW. She also calls out experimentation as one of the key growth levers that helped her get to 15k subscribers in 2 years:
Live Streaming a Product Hunt Launch
Milly said she didn’t love the “ick” feeling of how people normally launch products on Product Hunt. But, she knew there was a big upside if you get it right – subscribers, paying customers, etc.
So she wanted to try something a little bit different.
She decided that instead of sending a bunch of DMs and emails out, she was going to livestream the whole thing.
International Generalist Day
Over time, community members started telling Milly and her community leader that they were interested in doing local meetups. They started empowering certain members to host these and it started to take off pretty fast.
That morphed into what started as a joke in the community, “imagine we had a day for generalists.”
In 2024, they had the first annual International Generalists Day. There were 25 local hosts around the world.
Milly and the team also had the 2nd annual International Generalist Day this year. They thought 50 meetups would be the stretch goal. But it far exceeded their expectations.
I found over 87 events that were put together all around the world this year:
She told us on the Growth In Reverse podcast that over 3,000 people across 35 different countries came together to celebrate this day.
That’s wild.
A Podcast
Milly co-hosted a podcast for a year, from January to December of 2024. It was called Generally Curious, and they had generalists come on and share their stories.
That version of the podcast didn’t seem to work out super great, and they changed it up to be all members from the community.
If you couldn’t tell from this deep dive already, Milly is a big fan of flywheels.
This new version of the podcast, creates an amazing flywheel that drives more members for her community. Since she’s interviewing members, that member feels much more tied to the brand, they might share it with more friends, and then other people find the community, and they might decide to join.
This flywheel keeps spinning, and Milly doesn’t haven’t to work super hard to find new guests – they’re already in her community 🙂
There were many more experiments, but it’s fun to look at a few and see how she’s thinking about business. In short, it seems like “try stuff, break things, keep what works, and throw out what doesn’t” is the name of the game.
If you want to listen to our full episode with Milly, you can do so here:
Tool Stack
Because I think it’s always fun to see what tools someone has been using to build their business, here are a few I found:
- Beehiiv to write articles and send out her newsletter
- ScoreApp to build out the quiz for her “elite” flywheel
- Senja to capture testimonials
- Slack to run her community
- Butter as a Zoom alternative to run much more engaging meetings
- Notion as a catch-all for writing, organizing the business, etc.
- Gamma is a tool that helps build out presentations, slides, and websites
- Riverside for hosting her podcast(s)
- Zapier to automate and connect different software tools together
That’s it for this edition of the deep dive. If you enjoyed this, share it with a friend and tag me on social media. If someone shared this with you, subscribe to the Growth In Reverse newsletter to get more of these right to your inbox.
