Kieran Drew spent three years eliminating every hour of time-for-money work from his online writing business.
He invented a metric to track his leverage and published the number every month.
When profitable revenue streams dragged it in the wrong direction, he killed them.
He was willing to sit through through back-to-back months of lost revenue so he could push the number higher.
By late 2024, his writing business had crossed seven figures, and he had finally hit the leverage target he’d set two years earlier.
Then he launched a one-to-one coaching program and filled every spot in two days.
He was choosing the exact type of work he’d spent three years measuring his way out of, and he was loving it.
What looked like a massive compromise was in fact an evolution, and it all started with a dentist’s chair, a podcast during COVID, and eighteen months of earning nothing.
Bad Jokes, a Broken Neck, and a Thousand Followers
Prior to 2020, Kieran Drew was a dentist working fifty hours, six days a week for a decade.
The pay was good, but he felt trapped by the ten years and six figures he’d invested in becoming one.
He later described the feeling on a podcast: listening to creative people talk about their work and thinking, “Oh God, I’m in the wrong career, but there’s literally nothing you can do.”
His plan was to suck it up and double down. Specialize, take a second job, and get enough money together to retire in ten or fifteen years and try something else.
Like a bad gambler pushing more chips onto the table.
Then COVID hit, and for the first time in years, his calendar was empty.
A friend sent him Naval Ravikant’s podcast on permissionless leverage, the idea that you could build assets that earned while you slept without needing anyone’s approval to start.
Naval’s advice was to pursue your curiosity and Drew’s first instinct was comedy.
He started writing jokes in his spare time, figuring that making people laugh would be a brilliant job.
It didn’t stick. But the writing did.
He started publishing on Twitter in September 2020.
He’d been studying copywriting on the side during his last months in the clinic, and now he was putting it to work publicly.
Advice, personal stories, observations about writing and thinking.
He later described the experience simply: “I quickly fell in love. Writing is the most beautiful skill in the world. It improves how you think. It improves how you see the world.”
A year in, he had 1,000 followers. The writing had sharpened his thinking and taught him how to hold attention, but it hadn’t produced a dollar.
In August 2021, he joined Ship 30 for 30, a writing cohort built around a single challenge: publish something every day for a month.
The structure pushed volume, and volume surfaced what resonated.
On August 21st, he published a thread about something he’d never fully processed. He’d been diagnosed with a brain tumor and a broken neck at sixteen.
The story went viral and took him from 1,000 to 3,000 followers overnight.
Two weeks later, he quit dentistry.
Over the months that followed, he picked up 7,000 new followers and 600 email subscribers.
People were watching his writing grow an audience on social media and wanted to learn how to do the same thing.
He leaned into it, creating free video courses and detailed breakdowns of tweet hooks that taught the skill he was demonstrating in real time.
His first paying client handed him $500 for ten hours of coaching.
From there, the playbook looked like every other creator business coming up at the time.
Group coaching at $3,000 to $6,000 per person. A community at $20 a month with a $200 upsell for one-to-one access. He even had newsletter sponsorships at $250 per ad.
Revenue was growing, but unfortunately, so were the hours.
He’d left a career where he had been trading time for money, and suddenly found himself building another business doing exactly the same thing.
The job title had changed, but the structure hadn’t.
Two Loss Months and a Number That Said Keep Going
By January 2023, Drew looked at his numbers and could see what had happened.
Forty-three percent of his income was coming from low-leverage work.
Coaching and consulting, where every hour of the day he was required to be front and centre. The business was growing, but not in the way he wanted.
So he built a metric.
He called it the Freedom Metre. One number that tracked the percentage of his income coming from scalable, leveraged assets versus time-traded work.
He published it every month in his newsletter, right alongside his revenue and expenses. And he set a target: ninety percent high leverage.
Then he did something with it that most creators would never consider.
He killed his coaching businesses.
Revenue dropped eighty percent. His net income for July 2023 was $2,198.43.
He wrote about it publicly on his blog. “I’ve made a loss two months in a row now. But I’m happy because as a dentist, if my income plummeted, I’d have shit the bed.”
So revenue was down, but the Freedom Metre was moving in the right direction, and for Drew, that was the number that mattered.
What he was building during those months of lost revenue was a course called High Impact Writing.
He tested the material with a beta group of six people over three months, kept what worked, and cut what didn’t.
The course taught writing for social media as a business skill, priced at $397. Everything he’d spent three years doing publicly, packaged into a system.
By this point, Drew had over 30,000 email subscribers.
He’d been seeding the course through his newsletter for six months before it went on sale.
The audience had watched him build a following through writing and many of them wanted the same result.
The first launch brought in $140,000 in four days. A second launch four months later did $180,000 in another four days.
Eighty percent of the sales came through email, from a list that was roughly one-tenth the size of his social media following.
He added Magnetic Emails at $497, teaching the skill behind those same emails that were driving the bulk of his revenue.
A welcome sequence for new subscribers started generating automated income alongside the launches.
The Freedom Metre kept climbing.
Alongside these newly created courses, he was also running a subscription product called the Magnetic Content Masterclass.
It earned thousands of dollars a month on roughly five hours of work. He killed it. Called it “an average opportunity masquerading as great” and shut it down.
By late 2024, Drew published a special edition of his business report. Total revenue had hit $920,000. He’d been above ninety percent high leverage for a full year.
The metric had done exactly what he’d built it to do.
The Rule He Built The Business On And Then Broke
In October 2025, Drew turned around and wrote something in his monthly memo that would have been unthinkable two years earlier.
“I’ve realised that setting yourself rules reflects a lack of trust in the moment. You should not let your past dictate your present.”
He did what he’d spent three years actively moving away from, and launched one-to-one coaching called the Partnership Program. Spots sold out in two days.
He was doing lower-leverage work again, and according to his own memo, he was loving it.
Freedom, it turned out, wasn’t a percentage on a spreadsheet.
When Drew was coaching in 2022, it was his primary income. He needed those hours to pay the bills.
By late 2025, automated sequences were generating revenue while he traveled through South America writing a book.
His courses were selling through evergreen email systems.
Coaching, in that context, meant something completely different.
He chose his clients. He capped the spots. He structured the work around his writing schedule.
The income was welcome, but it wasn’t required.
The Freedom Metre got him out of the dentist’s chair.
What he found on the other side was bigger than any number could track: the ability to wake up and decide what his day looked like, whether that was writing a book or getting on a call with someone he wanted to work with.
What a Dentist’s Spreadsheet Can Teach You About Building Freedom
Drew had a decade of dental savings behind him when he made his biggest bets.
He could absorb eighteen months of earning nothing.
He could stomach consecutive loss months while building a course.
Most creators reading this can’t torch their income and wait for a flagship product to land.
The principle still holds, but the execution looks different.
If you’re building a creator business alongside a job or with revenue you can’t afford to lose, the leverage base gets built in the margins.
Automated email sequences. A product you can sell while you sleep. Systems that generate income without requiring your presence.
You build those alongside the time-traded work, not instead of it.
The ratio is what matters.
Track it. Watch it shift. Even moving from ten percent leveraged income to thirty percent changes what’s possible.
Which leads to the deeper lesson from Drew’s story.
He didn’t track followers or revenue as his north star. He tracked the one number that reflected what he actually wanted: time that belonged to him.
Most creators measure their business by how much it earns.
Drew measured his by how much of his time it consumed. That single decision shaped everything that followed, because you optimize for whatever you measure.
The question worth asking is what one number would tell you whether you’re building freedom or building a job.
If you don’t have an answer, your business is probably growing in whatever direction gets the most attention, and that may not be the direction you actually want.
There’s one more thing that only shows up at the end of Drew’s story.
Drew built a system, followed it with discipline for three years, and then gave himself permission to outgrow it.
The goal he set at forty-three percent leverage wasn’t wrong. It was scaffolding. It did its job and he moved on.
If you set a target for your business today, hold it tightly enough to make hard decisions by it, but loosely enough that you can recognize when the destination has changed.
The whole point of building leverage is to create options.
It would be a waste to arrive there and discover you’ve locked yourself into a new set of rules.