And 7 other takeaways from an expert digital marketer.
Olly Richards’ story reads like a masterclass in strategic positioning and authentic marketing.
But it didn’t start out that way. He was anything but an overnight success.
Olly was a broke jazz musician until the age of 28, when he decided to pivot from playing music for a living to teaching people to learn languages. He launched a blog called StoryLearning, and grew it to the point it’s now generated over $10 million in sales since its 2013 launch.
But it’s his latest project at OllyRichards.co that offers the most compelling lessons for creators and online entrepreneurs.
Let me explain.
The Google Doc That Started Everything
Two and a half years ago, Olly faced a familiar entrepreneur’s dilemma: “What’s next?”
StoryLearning had been successful to the point that Olly only has to work a few days per month “in” the business. So, he made a decision that would transform his business trajectory.
Instead of becoming another generic online business guru, he chose radical transparency.
“I was desperate to see people with other businesses like mine and understand how exactly they worked on the inside, but no one would ever talk about it,” Olly explains.
“So I thought, why don’t I just go full disclosure and write about how my whole business works?”
And that’s exactly what he did.
That thought turned into a 118-page Google Doc detailing every aspect of his multi-million dollar business: from email marketing systems to product ecosystems.
A Google Doc is far from flashy and borders on unimpressive. But that choice was intentional:
“The kind of people I’m aiming at, which are established business owners, they’ve seen it all before. They know when they’re being marketed to. They just want the information.”
From Free Content to $1.2 Million
The Google Doc itself wasn’t the money-maker. It was a 100% free, ungated lead magnet.
There were no sales pitches or links to buy anything inside of it.
You didn’t even have to enter your email address to access it at first. But the Doc was the foundation for how Olly planned to grow his personal brand and new business.
What this Google Doc case study did was earn Olly the credibility, authority, and trust required to eventually offer paid services for other digital entrepreneurs.
And that’s exactly what happened. Olly turned that Google Doc—indirectly—into $1.2m in business revenue. Remember, this business has nothing to do with his StoryLearning business. This is a venture he began in 2023.
Here’s how Olly transformed free content into 7-figure revenue:
The Revenue Breakdown
- 60% Mentorship/Coaching (~$720,000): High-touch, one-on-one work with entrepreneurs
- 20% Masterminds & Events (~$240,000): Including an exclusive annual mastermind for 8 people
- 20% Digital Products (~$240,000): Workshops and courses that scale without his direct time
The key to all this was positioning.
By sharing everything openly, Olly established himself as a trustworthy authority without the typical sales pressure.
“I didn’t advertise coaching at all. It was just people emailing me,” he notes. “I think because I got my positioning on point and managed to attract the right audience, people naturally started reaching out.”
The Self-Liquidating Flywheel
Perhaps the most brilliant aspect of Olly’s strategy is what he calls the “self-liquidating flywheel.” Here’s how it works:
- Spend on ads to generate leads ($5-10 per lead)
- Sell digital products ($50-100 workshops) to those leads
- Digital product sales cover ad costs (break-even or small profit)
- All coaching revenue becomes pure profit (no ad costs to recoup)
“I use digital products to cover all of the ad spend,” Olly explains.
“All of the 20,000+ leads I’ve got have been paid for through digital products, which means the million+ I made through mentorship and masterminds, I just get to keep.”
Fun fact: Growth In Reverse Pro members also get this course 100% free. Thanks Olly!
1. Newsletter Philosophy: Be the Trusted Friend
Olly’s approach to writing his newsletter is also worth paying attention to.
Instead of polished, templated newsletters, he advocates for raw authenticity:
“I see email as trying to be that trusted friend in the inbox. What does your friend do? They don’t send an email saying ‘Hey, I hope you’re doing well today. Here are three things I wanted to tell you.’ No, they just send a one-liner or something.”
His Newsletter Strategy:
- Frequency: 3-5 emails per week (aims for daily)
- Style: Stream of consciousness, very casual and raw
- Content: Whatever’s on his mind – from two sentences to massive essays
- Series approach: Serialized content with cliffhangers (like “How a Seven-Figure Business Dies”)
Olly’s pivot from publishing weekly, long-form essays to frequent casual emails was a huge unlock.
“Almost immediately since I started doing that, I started to get a lot more applications to work with me, a lot more product sales.”
As soon as he started publishing more frequently, he started seeing more sales. Go figure, right?
Consider this permission to experiment with a more-frequent-than-weekly edition.
The conventional newsletter approach is to publish weekly. And that makes sense because that feels more sustainable.
But Olly came up with a bulletproof content creation system that makes writing 3-5 newsletter editions per week simple.
2. The Bulletproof Content Creation System
Olly’s approach to generating newsletter content is bulletproof.
The key to making it work is in the first step: generating & collecting loads of ideas.
- Idea Collection: He uses a voice app called to capture ideas which “zaps” them them to a Trello board (currently 250+ ideas)
- Morning Writing Ritual: 30-60 minutes of writing time, creating 7-10 minute drafts
- Quantity Over Quality: Writes multiple drafts, picks the best ones to develop
- Multiple Touches: Comes back to emails multiple times rather than writing start-to-finish
“Great artists don’t just set out to write eight amazing songs. They write 20-30 songs and pick their favorite eight,” he explains.
Adopting Olly’s system above will ensure you never sit down at your keyboard to write without a list of ideas.
3. “Meta vs. Teaching” Content: A Critical Distinction
One of Olly’s most valuable insights involves the difference between “meta” content (the general “how” to do something) and “teaching” content (doing the actual thing):
“Most people are not systems thinkers. Maybe 10-20% of the population are systems thinkers. Most people just want you to teach them the thing.”
At Storylearning, Olly’s breakthrough came when he shifted from teaching “how to learn languages” to actually teaching specific languages step-by-step. This distinction can “unlock 80% more market” for many educators.
Maybe you’re writing a newsletter or publishing videos and stalling out on meta content. Consider applying the “teaching” approach and see what happens.
4. Standing Out in a Copycat World
Olly’s approach to differentiation is refreshingly simple:
“The easiest way to get noticed and provide value is to do the opposite of what everyone else is doing.”
His advice for creators struggling with algorithm-driven content:
- Know your numbers: Track which content actually converts, not just what gets views
- Focus on quality over vanity metrics: Often, lower-view content makes more money (he uses YouTube as an example, where some of his lowest-viewed content has converted the most traffic)
- Build relationships, not just audience: Email frequency and consistency matter more than perfection
You’ve heard the term “zig when they zag”. Being different can be a massive differentiator.
5. The AI Reality Check
Olly is not scared of AI, but he quickly realized the immense value in his decade-plus of knowledge and experience in the online world than ever before.
And that thinking is aligned with his decision to start a personal brand business.
“In a world where the value of information has gone to zero, who do you go to when you want to learn something? The person that you know, like, and trust. That’s where brand comes in.”
He advocates for the 10-80-10 principle when it comes to AI and content creation:
- 10% input: You engineer the prompt and provide direction
- 80% execution: AI does the heavy lifting
- 10% finishing: You add nuance, check for errors, make it your own
Olly even created a course about writing smarter & faster emails with AI:
6. Critical Mistakes Most Creators Make—and the Best Solution
Olly identifies a pretty massive problem in the creator economy: “There’s been a real decline in basic knowledge of internet marketing best practices.”
Some of the most common mistakes he’s seen include:
- Not using email effectively (or at all)
- Never taking copywriting courses
- Terrible landing pages with no testing
- No email automations or follow-up sequences
- Missing backend offers for existing customers
Olly’s solution?
“Learn copywriting. To be a good copywriter means understanding all elements of the business – customer journey, avatar, pricing, offer, front-end, back-end.”
7. The Foundation That Matters
One of Olly’s most dire warnings from our chat was against building businesses without proper foundations.
He mentions a “well-known creator” who announced in 2024 that they were running one final cohort of their course before shutting it down for good.
And this wasn’t just a small, solopreneur—it was a million-dollar business. The failure was, in Olly’s eyes, that they lacked the basic business fundamentals when external conditions changed.
“Those businesses that have the fundamentals are going to be able to adapt. The ones who don’t know their numbers, don’t understand how their businesses work from a structural perspective, are going to struggle.”
The Big “So What”
Olly Richards’ success isn’t just about one viral Google Doc—despite the opportunities it’s brought him.
It’s about strategic positioning, radical transparency, and building a business with proper fundamentals (trust, credibility, authority, and revenue-generating flywheels, to name a few).
In a world of templated content and algorithm-chasing, his approach proves that authenticity and business fundamentals still win.
Want to see Olly’s complete business breakdown? Check out his case study at ollyrichards.co – it’s all free and includes the 118-page Google Doc that started everything.
