🔴 A 6-figure creator business from a remote island

Every job is five jobs, and AI is taking four of them. Companies are smaller. There's a level of uncertainty in the labor market; specialization can feel risky — generalists can fill the gaps.

From this insight comes Generalist World, a community founded by today's guest Milly Tamati, generating six figures a year with over 600 paying members and 30,000 newsletter subscribers.

In this episode:

— Natalia Pérez-González, Assistant Editor

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It was 2022, and Milly Tamati was living on a remote island in the Atlantic with a population of just 191, wondering how to keep her career alive in one of the most isolated places in Europe.

The job market was still recalibrating after a global pandemic and any listings she found felt too narrow — every role demanded deep specialization. She'd always been the person who worked across disciplines, filling gaps between teams, functions, and titles.

So she started reaching out to CEOs directly, pitching herself as a multi-faceted asset. In those conversations, she realized these companies already had people like her — essential team members who didn’t fit standard job descriptions but held everything together — they just didn’t know what to call them.

She stopped pitching herself and created the platform she always wished existed: Generalist World — a newsletter and Slack community for multi-disciplinary professionals who didn't fit traditional job categories. She priced the first membership cohort at $150/year and strangers on the internet began to join.

Over the next three years, she tested prices ranging from $150 to $1,350, eventually announcing a shift to a $950 lifetime membership model just four months ago. That one-time cost is strategic — given the low cost of living on her remote island, it gave her the freedom to grow sustainably, without chasing hypergrowth or outside funding.

The model also eliminates churn: there’s no recurring payment to cancel, and there's no need for members to re-evaluate whether it’s “worth it” each month. Milly captures full value upfront, and members get permanent access with no expiration. With 600 paid community members to date, the model has generated a six-figure business, supported by a lean team of two full-time workers (now including a full-time community manager) and a few contractors. She pays herself just £12,500 a year, choosing to reinvest most of the revenue into improving the member experience.

But the root of her strategy — and most important factor in her success — is in building what she calls a “defensible personal brand.”

She’s posted nearly every day on LinkedIn for over 1,000 consecutive workdays, each post reinforcing the same message: generalists are valuable, employable, and essential. Her brand story, the messaging she delivers on every podcast, panel, and written post, all tie back to the core thesis of Generalist World, and lay out its purpose clearly and efficiently.

That kind of repetition — message discipline — builds trust over time and makes her brand resilient across platform shifts and economic downturns. It also powers her growth flywheel: her LinkedIn drives loyalty, her TikTok drives reach, and a lead magnet quiz captures interest from both platforms, converting social traffic into subscribers.

Built by a community member, the quiz — What Kind of Generalist Are You? — has been taken 30,000+ times and converted 20,000+ newsletter subscribers, mostly from TikTok. (Find a breakdown below in today’s Steal This Tactic section). Once members convert to her paid community, they find a Slack space that mixes meme threads with deep career discussions, with folks organizing local meetups from Copenhagen to New York.

Every new member gets a personal video welcome from Milly — a founder practice she refuses to automate. Programming ranges from weekly job boards to masterclasses with "hard-to-access" experts and large-scale events like the Summer School of Generalist Skills, sponsored by brands like Notion and Canva.

Landing Notion as a sponsor was a milestone; Milly pursued the partnership for two years, reaching out through four different contacts. The collaboration was a hit for all parties, and Notion renewed its sponsorship for another quarter — proof that persistence, positioning, and genuine product affinity can open doors.

It’s a mindset that’s shaped a sustainable, value-driven community. As major tech leaders increasingly recognize the value of generalists, Milly's early bet on naming, nurturing, and forming a profitable ecosystem around this professional identity is proving prescient. She’s created an entire community for people whose strength lies in their ability to adapt, connect, and operate across disciplines — all vital traits of essential employees, but also in today’s most successful creators.

A few things that stuck with me as I listened through this week’s conversation:

Connect with Milly on LinkedIn.
Subscribe to Generalist World and find out “What Kind of Generalist Are You?”

The Generalist World quiz has captured over 30,000 leads in just over a year by appealing to its core audience’s desire to understand their place and value in an uncertain labor market. It’s a simple lesson in driving newsletter sign-ups; don’t overthink it.

Milly’s quiz addresses a genuine pain point. Her audience needed language for experiences they'd lived but couldn't articulate.

Rameel Sheikh, a former Spotlight guest, employed a similar approach with "What's your Operator Style?" — a Myers-Briggs-style personality quiz sent in his onboarding email that converted 23% of recipients, generating over 1,300 responses in one four-week span. Both creators recognized that their audiences were struggling with questions about professional identity.

The key tactical insight: your quiz should diagnose something your audience suspects about themselves but do not have the language to articulate. Start by identifying the unspoken questions your audience asks, for example:

Then build your quiz around providing that clarity. Each question should contribute to the diagnosis while feeling relevant to daily experience. Milly outsourced quiz creation to specialists rather than building a basic version herself, recognizing it as an asset worth investing in.

Make sharing feel like an expression of identity, and create quiz outcomes that people want to share on LinkedIn or Instagram Stories. (Adobe did this well earlier this year with their “creative types” quiz).

People love sharing unique or rare results, and when someone gets a result that resonates, they want to broadcast it. Make broadcasting as easy as possible.

Milly directs all social traffic to her quiz, giving it pride of place in her links-in-bio — it’s her top conversion tool. This creates a more compelling call-to-action than your typical newsletter sign-up link, starting new relationships with immediate value delivery.

The quiz isn’t just a lead capture tool, though; when done strategically, it also functions as a research asset. Milly uses results to understand audience composition, tailor content for different generalist types, and identify potential community members. It captures leads and provides demographic insights that inform product development and content strategy.

The tactical play: segment your email list by quiz results, then create targeted content for each type. “Connectors” might receive networking strategies, while “Systems Thinkers” get process optimization tips. And you get a better-engaged, more deeply-trusting audience.

Use this data to guide product development. If 40% of your audience identifies with a particular type, consider creating a premium offer tailored to that segment. Track which types convert to paid products at the highest rates — this tells you not just who your audience is, but who your best customers are likely to be.