InIn this live, I’m joined by Ayodeji Awosika, or Ayo.
I wanted to have him on because his story is a pretty extraordinary example of what can happen when you figure out what you’re good at and turn it into revenue.
FROM $147 TO $10K MONTHS
In his mid-20s, Ayo was a college dropout with a felony conviction, working 12-hour shifts at an electronics factory for about $10 an hour.
He quit after six weeks. Around that period, he has said he was flat broke with just $147 to his name.
He eventually got a job managing a video store, moved into marketing and started writing online.
And then he kept writing.
That decision eventually led him to Medium, where he became the highest-earning writer on the platform for six months in a row and earned at least $10,000 a month for 19 consecutive months.
What makes his story especially interesting to me is what he did next.
He used the audience and expertise he built through writing to create books, courses, a writing community, consulting, coaching and other offers.
Those businesses went on to generate hundreds of thousands of dollars beyond what he earned directly from writing. He eventually left his job to write full-time and says the business he built from his skills and interests has now generated more than $2 million.
Today he writes Monetize Your Mind on Substack and teaches other people how to turn what they know into income.
So when Ayo talks about whether you can actually make money writing online, he has quite a bit of evidence.
FROM AN EIGHT-FIGURE BUSINESS TO STARTING OVER
My story starts at almost the opposite place.
By 30, I had pretty much everything I thought I was supposed to want. I was CMO and co-owner of an eight-figure creative agency, married with three kids, living in San Francisco and making very good money. I’d been working in marketing since I was 20 and assumed I had my career pretty well figured out.
Then at 38, my life blew up.
I got divorced, sold my shares in the agency and liquidated assets. Suddenly I had to figure out how to support myself and my family again, so I did the obvious thing: I tried to get a job.
I hired three career coaches, rewrote my résumé, fixed my LinkedIn profile, networked constantly and applied for more than 200 jobs over two years.
Meanwhile, I was raising four kids, watching my savings disappear and eventually accumulating debt.
So I started making money with what I already knew how to do.
Over the next several years, I tried consulting, services, coaching, courses, communities, digital products and content. I’ve tried 12 different revenue streams and made six pretty major pivots.
Some made a lot of money. Some were complete duds. A few taught me that making good money from something doesn’t mean you want to spend your life doing it.
That’s really where FU Money came from.
I know what it feels like to make a lot of money and still have a life that depends on continuing to work a certain way. I also know what it feels like to suddenly lose most of your financial options.
Now I’m much more interested in helping people build income they have more control over: more than one way to earn, things they own, and assets that can keep producing value after the original work is done.
Which is one reason I wanted to talk to Ayo.
Our stories started in very different places and eventually led us to something similar: figuring out how to take a skill we were good at and build a profitable business around it.
WHEN YOUR MAIN PLATFORM CHANGES THE RULES
Ayo and I had something else in common.
We both spent years putting most of our time and effort into one platform, got very good at it, built large audiences and were rewarded for it.
For Ayo, that platform was Medium.
At his peak, he was the highest-earning writer on Medium for six months straight and getting between 500,000 and one million views a month. For 19 consecutive months, he earned at least $10,000 a month directly from the platform.
He eventually grew to around 120,000 followers and says he made close to $500,000 from Medium altogether.
But Ayo did something smart while all of this was working.
He started building an email list early.
While Medium was sending him traffic, he was also using lead magnets to move readers onto a list he owned. Eventually that list grew into the tens of thousands. He was also writing books and starting to build products.
That turned out to be pretty good timing.
Medium changed how stories were distributed and how writers were paid. Ayo eventually saw his Medium income drop by about 80%.
By then, he had other things to sell and an audience he could reach somewhere else.
My main platform was LinkedIn.
I was part of LinkedIn’s creator program and was named a LinkedIn Top Voice three years in a row. That brought more visibility, credibility and opportunities. I grew my audience to more than 77,000 followers, and at my peak it wasn’t unusual for a post to reach 50,000 to 100,000 people.
That visibility turned into money too. It helped lead to six-figure brand deals, clients and other business opportunities.
So focusing heavily on one platform worked extremely well for both of us.
Then LinkedIn changed too.
Back in 2018, LinkedIn openly said its biggest creators were getting a disproportionate share of attention. It changed the feed and shifted about 8% of the engagement going to the top 0.1% of creators toward the bottom 98%.
And the feed has kept changing ever since.
By 2025, the drop in reach was hard to miss. An analysis of 3 million LinkedIn posts found that median reach had fallen by more than 47% in a single year.
I eventually did my own deep dive into LinkedIn’s newer algorithm because I wanted to understand what had changed.
DIFFERENT ORIGINS, SAME DESTINATION: SUBSTACK
That’s part of what brought me to Substack.
LinkedIn had been very good to me. I built a large audience there, found clients, landed opportunities and saw firsthand how much writing online could change a business.
I had no intention of leaving. I still don’t.
But I had become very aware of how much of my visibility and business depended on decisions I had absolutely no control over.
One week a post could reach 50,000 or 100,000 people. The next week, something just as good could reach a fraction of that.
I didn’t want so much riding on one platform.
So I started exploring Substack.
Part of the appeal was simple: if someone subscribed, I had a much better chance of reaching them again.
I also wanted to see what would happen if writing became part of the business itself instead of mainly being how I marketed everything else.
Ayo had already gone through his own version of this with Medium.
Medium didn’t disappear. LinkedIn didn’t suddenly become useless. We had both simply reached the point where it made sense to build beyond the platform that helped us get there.
When too much of your income, audience or business depends on one company deciding to keep showing your work, you have less control than you think.
If you’re trying to build more income and become less dependent on one employer, client or platform, that’s exactly what I write about here.
THE 33,000-SUBSCRIBER PROBLEM
Despite coming from different worlds and different platforms, there’s one thing Ayo and I agree on 100%.
If your goal is to build a profitable solo business, relying on Substack subscriptions alone is a very hard way to do it.
Ayo explained it in terms of volume.
Say you charge $10 a month and want to make $10,000 a month. You need 1,000 paying subscribers.
Using Ayo’s assumption of a 3% free-to-paid conversion rate, you’d need roughly 33,000 free subscribers to get there.
That is a hell of a lot of people.
And first you have to find them.
You have to write consistently, publish Notes, promote your work, collaborate, build relationships and keep growing month after month.
Can it work? Obviously. There are people making very good money from paid subscriptions.
Ayo’s point, and mine, is that people seriously underestimate the volume required.
He told me he’s seen Substack accounts with 30,000 subscribers and massively viral posts making around $1,000 a month.
His description of what went wrong was perfect:
They built the attention infrastructure without the business infrastructure underneath it.
And before the diehard writers come for us, neither of us is saying you shouldn’t have a paid tier.
Ayo literally said, “Keep your paid tier. It’s fine.”
If your dream is to write all day and you’re delighted that people will pay you to do it, fantastic. Life does not have to be one giant ROI calculation.
But if you came here because you want to build a serious source of income, you should understand the math before deciding subscriptions are going to get you there.
YOU DON’T NEED 30,000 SUBSCRIBERS. YOU NEED AN OFFER.
Ayo told me about a woman with just 67 Substack subscribers.
She had a higher-priced offer. She networked, collaborated, sent DMs and actually talked to people.
She signed clients.
Meanwhile, someone else can spend years building an audience of 30,000 people and still struggle to turn all that attention into meaningful income.
I think a lot of creators have the order backwards. They assume they need to build the audience first and figure out the business later.
So they keep writing, posting Notes and celebrating every new subscriber, while the question of what anyone might eventually pay them for gets pushed further down the road.
Ayo has spent years working with creators and sees this repeatedly. Growing the audience won’t magically tell you whether you have something people will buy.
His advice is to test much earlier.
He has created programs by writing the sales page before building the program. If enough people were willing to put down a deposit, he built it.
You don’t have to start with a $3,000 or $5,000 offer either.
Offer a consulting call. Put together a workshop. Create a small product around something people already ask you about. Describe it, put a price on it and see what happens.
You’ll learn a lot faster from someone pulling out a credit card than from another thousand people clicking Subscribe.
And please don’t sit around waiting for people to magically reach out and ask how they can give you money.
If you want to build a business, eventually you have to make an offer.
SO, CAN YOU ACTUALLY MAKE MONEY WRITING ONLINE?
Absolutely.
Ayo found writing almost by accident, went all in on Medium and eventually became the highest-earning writer on the platform.
I spent decades in marketing, built my audience on LinkedIn and came to Substack much later because I wanted writing itself to become a bigger part of my business.
We arrived here through completely different routes and ended up agreeing on quite a lot.
Writing can create attention, credibility, relationships and opportunities. A platform can completely change your career. Ayo is living proof of that.
But a large audience on its own can still make very little money.
Ayo earned hundreds of thousands of dollars directly from Medium and still kept building. He created an email list, books, courses, a community, coaching and consulting. So when Medium changed, he still had a business.
That’s probably the biggest thing I took away from our conversation.
Take advantage of the platform while it’s working. Become excellent at it. Build the audience and enjoy the opportunities that come with it.
Then build something you control around that attention.
Because 30,000 subscribers who never buy anything can be worth considerably less to your business than 67 people who actually need what you know.
Ayo’s story obviously doesn’t mean everyone who starts writing with $147 in the bank is going to build a $2 million business.
It does show what can happen when you find a skill that fits you, get very good at it, and then figure out more than one way to make money from it.
WANT MORE?
If you want to read more from Ayodeji, go find Monetize Your Mind on Substack.
I especially recommend his story about going from $147 in his bank account to building a business that has generated more than $2 million. There’s a lot more to his story than we could possibly cover here.
And thanks to everyone who joined us live. This conversation could easily have gone another hour.
Thank you Shannon D. Smith , Claire Machado, Dennis Njuguna, Cynthia | Intuitively Wealthy, Cristina Segatto, and many others for tuning into my live video with Ayodeji! Join me for my next live video in the app.
