The Portfolio Career

How I make money

Quick note before we start. This is the first in a series of essays where I’m getting back into writing about business. I’ve been quiet on it for a while, mostly heads down building and learning behind the scenes. But I’ve missed this. So, welcome back, and enjoy.

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“So what do you actually do?”

I get some version of this question a few times a week. And for a long time, I didn’t have a good answer.

Am I an entrepreneur? An author? A ghostwriter? An influencer? Some mix of all four?

It used to bug me. I like clear definitions.

How do you explain that you get paid to... be yourself?

But recently, I’ve come to see it as a gift. I don’t want to be one thing.

I call this a portfolio career. And for the first time, I’m going to explain what it is and how you can build one.

If you want to get paid to follow your curiosity, earn from your mind instead of your time, and build a life around fun, freedom, and fulfillment… this essay is for you.

The Default Path

For most of my life, the path laid out before me was: Go to college. Get a business degree. Probably go into finance (since it paid the best). Climb the ladder for a decade or two.

And then, maybe, once I had enough money and experience, start something of my own.

Don’t get me wrong, there’s nothing wrong with that path. But it bugged me that it was all reliant on the idea of “someday.”

Someday you’ll have enough saved. Someday you’ll have the freedom. Someday you’ll do the work you love.

But “someday” is never promised. In fact, tomorrow’s never promised.

So I asked myself, why not start now?

The Myth

Tying all of your income to a single employer is one of the riskiest things you can do. And a lot of people are learning that the hard way right now.

I have friends who got laid off this year. Smart, hardworking people who are struggling to find opportunities. And it’s not because they’re not putting in the effort.

It’s just that they spent years as one small cog in someone else’s machine.

When their job disappeared, they had nothing that was theirs. They didn’t have an audience or a skill set the market wanted, so they had to start over from scratch.

A portfolio career is a hedge against that. When your income comes from many different places, no single loss can wipe you out (and it usually pays better than a safe job).

What’s a Portfolio Career?

A portfolio career is building an audience and monetizing it in many different ways.

You get good at a skill. You build a following around that skill. Then you turn that attention into income streams that stack on top of each other.

Those streams can be almost anything: services, sponsorships, ad revenue, digital products, software, books, speaking, investing, joint ventures with friends.

For me, it’s a boutique copywriting studio, writing cohorts, advising and investing in creator startups, YouTube, and books.

But the part I love the most isn’t the money. It’s the freedom.

Most people get a job and then fit their life into whatever hours and location it demands.

With a portfolio career, you flip that. You ask, “How do I want my days to go?” and then build income around your answer.

I call this daily wealth.

The 3 Principles of a Portfolio Career

1. Distribution is everything.

Your distribution is the business. Your life is the marketing.

Without an audience, you don’t have a portfolio career. You have a list of hobbies.

The audience is what becomes clients, customers, readers, and investment opportunities. I’ve grown a following of over half a million people, and almost every client I’ve landed came inbound from it.

I do very little outreach. The only cold outreach I do is for the handful of specific people I really want to work with.

Your life is the marketing in a literal way, too. The more interesting and fulfilling your life is, the more you have to say, and the better your content gets.

How happy you are with your life turns out to be a decent leading indicator of how good your marketing is.

2. Profit over hype.

In business, I care about two things: cash flow and longevity. How much money is hitting my bank account, and how long I can keep doing this.

Everything else is noise.

I don’t care about your valuation. I don’t care how much you raised. I don’t even care that much about revenue.

Those numbers make for good tweets but bad businesses.

3. Concentrate, then diversify.

When people hear “multiple income streams,” they try to start 5 things at once. A newsletter and a podcast and a course and an agency and a fund, all in the same month.

Then they wonder why all 5 are stuck at zero.

If you try to do everything well, you’ll do nothing well.

So you don’t start diversified. You concentrate, then you diversify.

Pick one skill. Build one audience. Land on one offer that makes real money.

Right now my short-form content system is dialed in. I have posts scheduled into early 2027. That baseline is handled, which frees me to put my energy into YouTube, promoting my book, and a few other ventures.

Each new project has a partner or a lead running it day to day, so I get to steer the ship instead of row it.

And when a new opportunity shows up (it will), I run it through 3 questions:

Fun: if this took twice the time and paid half as much, would I still want to do it?

Freedom: what am I saying no to by saying yes to this?

Fulfillment: am I helping people, and am I enjoying the work?

How to Do It Well

If I were starting again, this is the path I’d follow…

1. Pick a high-income online skill.

Online, so you can do it from anywhere in the world. High-income, so you’re building on something the market is actively paying for.

Copywriting, marketing, design, coding, editing, sales.

If you build on a skill with thin demand, you’ll fight for scraps. Pick something people already spend money to get help with.

2. Build an audience around it.

Start publishing what you’re learning as you learn it. This is your distribution.

It grows slower than you want and faster than you think.

3. Craft an offer.

When you package your skill into something you sell, play with 3 levers: speed, risk, and ease.

Help people get results faster, with less effort, and with less risk of it not working.

Get good at those 3 and the offer starts selling itself.

4. Stack skills, one at a time.

When I started, I could write a decent tweet and edit a simple video. Clients paid me $500 to $2,000 a month to run their social media. Useful, but a commodity. Anyone could do it.

So I got better. I learned psychology, branding, and how to write content that performed. That took me to $3,000 to $5,000 a month.

Then I went deeper into marketing: offers, funnels, email, landing pages, paid ads. Now I wasn’t just growing someone’s social media. I was growing their business.

That’s a $20,000 a month service.

Each skill on its own was ordinary. Stacked together, they made me hard to replace. In 4 years I went from $500 a month to $20,000 a month. A 40x, without ever being the best in the world at any single one of them.

You don’t need to be #1 at one thing. You need to be great at a few things that combine into something rare.

5. Keep going.

I know, I know. Booooring.

But a portfolio career (just like any career) takes time to compound. Just because you don’t see progress doesn’t mean you’re not progressing.

One last thing you should know before you start.

When you run a portfolio career, you’re your own boss. Which sounds great until you realize it means you have to be a good employee to yourself.

Nobody makes you show up. Nobody sets your hours. Nobody notices if you spend the whole day “researching” on YouTube.

You have to build your own structure, hold your own deadlines, and do the boring work when no part of you feels like it.

Managing yourself is the skill almost nobody has starting out. It’s also the reason I don’t think jobs are bad.

A job is a great place to learn how to work. How to show up on time, hit deadlines, carry real responsibility, deal with people you didn’t choose.

I just think a job should have a purpose beyond the paycheck. Use it to build the skills and the discipline you’ll need on your own.

We’re Early

We are living in a golden age for entrepreneurship. It has never been simpler to make a good living from work you care about.

Entrepreneur comes from the French entreprendre: to undertake. To take something on and bring it to life.

You don’t have to raise a bazillion dollars or hire a big team or start a restaurant to be one.

You can carve out a small corner of the internet, become known for one thing, and build a career that nobody can lay you off from.

Until next week,

Jay “Concentrate, Then Diversify” Yang

Ps. I believe one of the few career slingshots that still exists is finding someone who’s already living the life you want and getting as close to them as you can.

Almost everything good in my career traces back to the decision to find people ahead of me, make myself useful to them, and learn things I could have never learned otherwise.

If you’re thinking “that sounds great, but where do I begin?”, that’s what my new book is about. Work With The Best is my cookbook for creating your own opportunities:

• How to write a cold email that gets replies

• How to structure a pitch someone can’t ignore

• How to create value for people ahead of you

• How to get on their radar

• How to build a network from nothing

It’s everything I’ve learned in the last 5 years of building. You can grab your copy: https://www.kickstarter.com/projects/jayyanginspires/work-with-the-best