My Portfolio Career Architecture [#100]

100+ newsletter editions in, it's time for a review: how it started, how it's going, and how it's going to go. Read this if you also want to have a portfolio career.

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Welcome to newsletter #100!

What started out as a simple accountability mechanism for writing, now has turned into the centerpiece for my very own portfolio career.

A lot of you here are curious how to build one too, I suppose. So today, I wanted to break down how I got to this point, how I’m currently structuring my portfolio career, and what the plans for the future are.

I wish a lot of people had documented their journeys so I could learn from them. So I’m doing it myself, in the hopes that someone in the future will have a slightly better career for the sake of it.

Let’s dive in. ⬇️

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How it started

December 2022. I’m happily employed full-time, running International Expansion for an EdTech scale-up … but feel like something’s missing.

Flow.

I hadn’t been in a proper flow state in ages. My workdays were fragmented, at Lacrosse practice, I’d never fully get into it because I had to keep too many tabs open as team captain, and outside of those two things, I didn’t really find it.

I asked myself: “when was the last time I was properly in the zone?”

The first three instances that came to mind were all doing the same thing: writing. I hated sitting down to write, I hated writing the first couple lines, but loved the feeling that came after. And I loved the end result.

It felt a bit like cardio training: putting on your running shoes sucks, starting the run is equally terrible, but 20 mins in, it starts becoming pleasant.

I needed an accountability mechanism. In training, committing to others that you’ll be there works like a charm. So why not use the same for my writing?

Cool. Set up a Substack, announced on LinkedIn that I’m launching a bi-weekly newsletter, committed to 8 editions of it, imported the 87 subscribers I had collected from my previous blog, and started writing the first edition between Christmas and New Year’s.

At the time, I had no idea what I wanted the newsletter to be about. I called it “International Generalist”, because I was doing a lot of international things and considered myself a generalist. (Yes, really. 😂)

Early editions were a mix of random insights and thoughts I’d dug up on the internet or otherwise came to my mind; not nearly as structured as it is today.

There was no grand plan, no scope, just this:

And a commitment to write eight of them.

Taking action taught me more than overthinking the premise of the newsletter ever could have. Hell, I still don’t really have a proper brand name for this newsletter. Or a properly defined premise.

That doesn’t matter; what matters is just doing the thing.

Writing was joyful. Subscribers kept growing. After 8 editions, I had no intention of quitting. And just kept writing. Started posting on LinkedIn, mostly because I was frustrated few people were actually reading my content. That somewhat worked, but not super well.

One year later, I decided to invest – and joined the Un-Ignorable Challenge, a cohort-based course that helps you write, well, un-ignorable content.

There, I professionalized a lot of my presence: properly defining what I wanna write about, editing taglines, learning all about social media posting. My LinkedIn presence took off, and with that, new subscribers came in.

I started becoming more interested in the Creator Economy. Bought Justin Welsh’s ContentOS. And started dreaming about selling digital products one day.

A one-man show that makes >1M in profits yearly, just by selling books and courses? Sounded fantastic at the time. But for that, I needed a much bigger audience.

I got stuck there for a while. In the meantime, I had left my job (not because my newsletter was so successful, but because I simply had outgrown the company or the company had outgrown me). Took a sabbatical. And suddenly, had very few things to talk about – because I wasn’t doing things worth talking about.

This, generally, is a big problem with the creator economy. People become so obsessed with growing their audience that at some point, the only thing they can talk about is how to grow their audience.

They record an online course on content creation that teaches you how to make money by creating online courses full-time – but if that’s all you do, the only thing you can talk about is content creation.

An endless pyramid scheme.

And I needed to break the cycle. By doing something meaningful in life. Something worth writing about.

I was entering my solopreneur phase, the first phase of the three steps to Multipreneurship.

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The Solopreneur Phase

Ever since first encountering the creator economy, I’ve thought about having a digital product. And since I hate it when people talk about something, yet never follow through, I knew I had create one. It’s hard to make money online when you have no way for people to give you money.

I asked a few friends: “what’s something I’m exceptionally good at?”

The answers painted a clear picture (also, a bit, to my surprise): personal productivity. To put it with Patrick’s words:

Interesting. So I sat down, broke down all the things I do in order to get the most out of my time, realized that it’s way more than I thought, wrote an outline, created frameworks, formalized systems, and wrote scripts.

Eventually, I recorded the entire thing and did a first beta run.

Got some harsh, constructive feedback (special thanks for David, Philip, Flora here). Recorded v2. Started writing a launch sequence over 10 editions. Designed and tested a landing page.

And on October 15th, 2024, I launched the entire thing.

Man, that was an interesting experience. I hit “publish”on the launch email, and went on a date. During it, I kept refreshing my email … to see orders coming in (!!!).

Let me tell you: when those first order confirmations hit and you see revenue in your Stripe dashboard … that just hits different.

It’s the ultimate empowerment as entrepreneur: it proves that YOU have the capability to create something people are willing to pay money for. I finally had my proof that I can, in fact, make money with digital products.

To be honest, the launch was … okay. It didn’t generate the >500k other creators brag about. But it also wasn’t terrible. It did bring in some revenue, but most importantly, it gave me confidence.

That I can actually do all this.

And that was enough.

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Speaking of the online course: it’s called Personal Productivity OS – and contains 17 systems, digested in less than 3 hours, that will save you up to four hours per day. No s**t. I use those techniques daily, and when I don’t, I notice the effect immediately.

I’m running a Cyber Monday sale until the end of the week: 49% off.

(Why the odd number? I launched the course with the promise that it’ll never be this cheap again. I tend to stick to my promises. So it’s gonna have to be 49% instead of 50%.)

If you don’t see any effect from applying the techniques & systems within 30 days, email me and I’ll give you a full refund, no questions asked.

Use the code HELLYEAH49 at checkout.

Get Personal Productivity OS today for 49% off

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The Entrepreneur Phase

With that out of the way, it was time to found a company. The digital product existed, but I also couldn’t bear it anymore to talk about personal productivity. I had my solopreneur thing now; the next step on the ladder to multipreneurship was to found an actual company.

That company turned out to be Generalyst, and since you’re subscribed to this newsletter, there’s a high chance you know exactly what it does.

What’s more interesting is the impact the company launch had on this newsletter:

The first spike you see is the launch of Personal Productivity OS. Apparently, people thought it was interesting to see what this launch looks like.

The second, bigger spike - and the continuous growth - was the launch of Generalyst.

On Nov 6th, I was in Edinburgh, sipping steaming hot filter coffee. I turned to Damian, the friend I was there with, and said: “I think it’s time.”

I hit “publish” on the LinkedIn launch post, set a job ad live, closed my laptop, and went to the pub for a few pints.

The next morning, Generalyst had >50 applications. And approximately 40 new subscribers. Holy s**t.

It seemed to be working.

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How it’s going

Fast forward one year, and here’s the current state of affairs in the portfolio career.

1. Generalyst is the main thing. The company now pays me a modest salary, makes a few placements every month, and is now ready to add a few more people besides Cesca (Founder’s Associate).
2. Personal Productivity OS makes a sale here and there, nothing crazy, but it’s a nice subsidy.
3. I intentionally don’t monetize the newsletter (except for the occasional affiliate link; there’s one in this newsletter, maybe you can find it).
4. I want as many people in the target group to read it as possible; if I put up paywalls, that won’t happen. Money can be made elsewhere. That doesn’t mean I never will, but for now, that’s the philosophy.
5. I also do some one-off consulting here and there (mostly on international expansion), which brings in some money and provides a welcome change of pace.

It’s not always easy:

• I could make more money working in any of the positions I’m placing with Generalyst.
• The concept of “days off” doesn’t really exist anymore. (I’m writing these lines on a bus ride through Northern Patagonia, on and off while chatting with an elderly Argentine gentleman.)
• A lot of things inside the business break if I don’t pay attention, and I’m a huge bottleneck.

Every now and then, doubt creeps in.

• Am I doing the right thing?
• Am I growing at all?
• Am I surrounding myself with the right people?
• Is this business really gonna work, or be made obsolete by AI?
• Should I say yes to some of those opportunities around me?

And every now and then, joy creeps in, too.

• Holy s**t, I can literally just do things.
• Holy s**t, more than one thousand people read my writing every week.
• Holy s**t, I’m actually making an impact here.
• Holy s**t, I can run my business from a different continent without skipping a beat.

This gives me confidence.

Because confidence, in the end, is just a series of proof points that you can do something.

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How it's gonna go

The biggest danger in a portfolio career is a complete loss of focus. Since you can do many different things, and design your career accordingly, you can technically say yes to any given idea.

But if you say yes to everything, you also say no to doing anything particularly well.

The best tradeoff I’ve found so far is a time allocation stolen from Google:

• 70% of time on the main thing (ie., Generalyst)
• 20% of time on a proven side thing (ie., content, digital products)
• 10% of time on a completely new thing

For now, I’ve created a job for myself with Generalyst. It pays the bills, but I also need to allocate 40+ hours every week to run the company.

Short-term, therefore, the first objective will be to turn my job into a proper business – with the right people in place so that it can run itself eventually. This also includes line extension and geographical expansion.

On the side, I’m working on professionalizing my content production. Writing works, newsletter and LinkedIn are covered. But I feel like the message that the future belongs to generalists needs to be spread across more channels. Mostly, video.

Given that I’m not very good at this entire video thing (it requires a lot of attention to detail, which isn’t a strength of mine), I’ll need some help here. To build systems, and do run the content ops.

(If you’re into that kind of thing, do reach out.)

I also have a few ideas for new digital products: there’s a book floating around somewhere (don’t wanna talk to much about it, as talking publicly about a goal decreases your chances of reaching that goal), smaller online courses (30-45min), email series, things like that. But they take up the minority of the time.

The ideal picture I’m working towards looks like this:

Content is at the core. All my businesses drive followers / subscribers to the content channels, with the newsletter being the core of the entire thing. In return, the newsletter funnels leads towards the different businesses.

All of this creates a flywheel effect that grows the audience, and subsequently the other portfolio businesses.

A concrete example:

• A candidate applies to Generalyst
• They begin reading the newsletter and eventually buy Personal Productivity OS
• They find a job via Generalyst
• They get promoted six months in, and need to hire someone to replace them
• So they approach Generalyst to hire with them
• I release a new online course
• They had a great learning experience, so of course they’ll buy that one too
• I launch a new business, catering towards a similar target group
• Guess who’s gonna be customer number one

There’s a bunch of combinations here, but you get the idea.

The Multipreneur Phase

Eventually, this will turn into a machine that allows for easy creation of new businesses: with leads generated by content, A+ talent funneled into the new business via Generalyst, etc.

And that’s exactly what I’m aiming for: I know myself well enough to know that 3-4 years into one topic, I’ll get bored, and wanna do something new. This construct allows me to do exactly that: to launch new businesses with a much higher chance of success than just doing so sequentially.

I have a few ideas, but … that’s for a different day.

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This is how a simple decision at the end of 2022 turned into the cornerstone of an empire, built for years to come.

It all started with a single email.

If there’s one thing you take away from this: you can do this, too. If you don’t know what to do, taking action is always better than not taking action. Doesn’t matter if it’s right or wrong, but that action is gonna show you the next step.

Your portfolio career is likely gonna look very different. That’s good. That’s the entire point of building one: so you can build something that works for you.

Build the life that you want, not that others want you to live.

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Asks

• If you’ve been struggling to be productive, consider buying Personal Productivity OS. HELLYEAH49 gets you 49% off at checkout. If you hate it, I’ll refund you, no questions asked. Just email me.
• I’m hiring a social media intern in December or January. Here’s the job – if you know someone that’d be a perfect fit, let me know.
• What could a portfolio career look like for you? I’m super curious – email me, and I’ll share my thoughts.

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Happy Monday. Have a great week – let’s finish 2025 strong.

LFG. 🔥

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