The Art of Selling Online Courses

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Iwona Podlasińska picked up a camera in 2014 to photograph her own kids. Ten years later, she's run workshops in 17 countries, was named the most followed photographer on Flickr in 2017, and has thousands of students learning her distinctive dreamy, light-filled portrait style. John sat down with her to hear how that actually happened, and what running that kind of business really looks like day to day.

What came through most clearly was how honest Iwona is about the gaps. She knows she has a large, loyal audience across Facebook, Instagram, and YouTube. She knows she has products people want, from in-person workshops priced up to $1,000 a ticket to courses, presets, and overlays. But the bit in the middle, converting that audience into consistent revenue, is the part she's still working out. Her email marketing hasn't been performing and she's not entirely sure why. Her organic social reach, which has always driven workshop bookings, is starting to get harder. And she's thinking seriously about what she offers after someone has already done a workshop.

She also talked about something that doesn't come up enough in these conversations: the value of cooperation. Partnering with hosts, organizations, and other platforms has consistently widened her audience, even when it meant sharing the income. That's a trade-off she's made deliberately, and it's worked.

This one's a little different from our usual episodes. Iwona isn't sitting on a polished system. She's a world-class photographer figuring out the business side in real time, and that makes it a genuinely interesting conversation. I think you'll enjoy it.

Check out Iwona's work:
🌐 https://iwonapodlasinska.com
📸 https://www.instagram.com/iwonapodlasinska
▶️ https://www.youtube.com/@iwonapodlasinska

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Rosalie E'Silva spent years at CNN, NBC, Al Jazeera, and Bloomberg telling other people's stories. The whole time, she was keeping a secret: she'd been having out-of-body experiences since childhood and had never told anyone.

In 2024, she left broadcast journalism to teach Yoga Nidra for astral projection. She now has over 150,000 YouTube subscribers, more than 20 million views, and a course community whose students are so engaged they meet on Zoom and Discord without her, multiple times a week, just because they want to.

I sat down with Rosalie to talk about how she built this from scratch, starting with a video she almost deleted. They got into what astral projection actually is, why people seek it out, and what it does to someone who experiences it firsthand. Rosalie has a real gift for making something that sounds wildly esoteric feel completely accessible.

They also got practical. Rosalie's YouTube channel is bringing in around 207,000 views a month, but her email list sits at just over 1,500 people. I walked through exactly what I'd change, from where to place the lead magnet in meditation videos, to using her existing tracks as a tripwire offer, to what a simple value ladder could look like for her business.

It's a genuinely unusual conversation, part business strategy, part window into a world most people have never heard of. I think you'll enjoy it.

Check out Rosalie's work:
🌐 http://rosalieesilva.com
▶️ http://www.youtube.com/@RosalieYoga

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Jim Cockrum has been doing this for 24 years, and he still texted three coaching students personally this week just to check in.

That detail tells you a lot about how Jim runs his business. He's the founder of Proven Amazon Course, host of Silent Sales Machine Radio, and the author of a book that's been read by over a million people. His funnel starts at $7 and goes to $7,000, he's coached more than 7,000 students, and his Facebook community has 80,000 members. But the thing that struck me most in this conversation wasn't the scale. It was how much of his success comes down to a philosophy most people resist: give everything away for free.

We talked through his entire funnel, from how he spends $50–$90 to acquire a $7 customer and recoups it within 30–90 days, to why he says there's nothing behind his paywall except time and relationship. He told me about a real estate client who fired him for suggesting free, then called back months later when the paid version flopped. And he shared the Death Wish Coffee story, where a single email blast outperformed a Super Bowl commercial in sales.

We also got into email list hygiene, why he maintains 40% open rates by scrubbing non-clickers, and why he thinks getting people onto a screen is the most underrated move in any funnel.

Jim is sharp, generous with what he knows, and genuinely fun to talk to. I think you'll enjoy this one.

Check out Jim's work:
🌐 https://www.silentjim.com/
📸 https://www.instagram.com/jimcockrum/?hl=en
▶️ https://www.youtube.com/c/silentjimdotcom

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Elsa runs Peace of French, a YouTube channel with hundreds of thousands of subscribers, and she built the whole thing again in Hebrew. Every day, companies email her offering money to promote their language apps. She says no almost every time.

Dominik sat down with Elsa to find out why, and what he got was a really clear-eyed conversation about what it actually means to run a course business rather than an influencer operation. Elsa started teaching French to her partner, found YouTube, and built from there, filming on a bad phone with no microphone until she hit 100,000 subscribers.

What I found most interesting was her thinking on trust in the age of AI. She isn't panicking. She thinks the creators who've built real relationships with their audiences have something AI can't replicate, and she's been quietly building that kind of connection by sharing her everyday life alongside her lessons.

She also talked through her quiz funnel, why she's cautious about over-discounting, how she deliberately prunes her email list, and what happened when she closed her membership and repackaged it as a one-time product. That last part is worth listening to if you have an offer that's plateaued.

She's honest about what's hard too, including the real cost of running two businesses at once and waiting two full years before starting her email list.

Check out Elsa's work:
🌐 https://www.pieceoffrench.com/
▶️ https://www.youtube.com/@UCVzyfpNuFF4ENY8zNTIW7ug

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Victor Damasio grew up selling newspapers on the Rio subway and working pub crawls to pay his way through law school. 
Today he has 729,000 Instagram followers in Brazil, nearly a quarter of a million YouTube subscribers, and a mastermind he charges $20,000 to join. This conversation is about what he figured out in between.

I sat down with Victor to talk about one specific idea: why course creators who already have an audience and existing clients are leaving serious money on the table by not having a high-ticket offer. Victor's argument is simple and hard to argue with. If someone in your audience would pay ten times more to get closer access to you, and you never give them the chance to do that, you're treating all your clients the same when they're not.

Victor walks through his four-question application process, what he calls the Spartan method, which flips the usual sales dynamic. Instead of you pitching someone, they apply to work with you. He explains exactly what to ask, what good answers look like, how to run a 20-minute vetting call, and why saying no to the wrong clients is something they'll actually thank you for.

There's also a genuinely useful analogy involving Qatar Airways business class that I haven't been able to stop thinking about since we recorded this.

Victor is just starting to build his English-language audience, so if you want to reach him while he's still responding personally to messages, now's the time.

Hope you enjoy this one as much as I did.

Check out Victor's work:
🌐 https://www.victordamasio.com/eng-us
📸 https://www.instagram.com/victordamasio/
▶️ https://www.youtube.com/channel/UCEF03nN_kI6RKznPRw9x7MQ

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Mark Wales has had a career that is genuinely hard to believe. Sixteen years in the Australian Army, four tours of Afghanistan with the SAS, an MBA from Wharton, a stint at McKinsey, and then he won Australian Survivor. Now he is building an online course business around leadership and resilience, and he emailed John to say he had been studying the podcast and was ready to build his funnel.

What made this conversation so good is that Mark is right in the middle of it. The course is built, the YouTube channel has 1.8 million lifetime views, and the goal is $5,000 AUD a month in revenue. But the email list is at 1,300. So John walks through exactly what needs to change, from where to place lead magnet CTAs in videos, to the 1% opt-in benchmark Mark should be hitting, to how many offers he needs to make consistent monthly revenue.

There is also a genuinely fun stretch where they figure out how to turn Mark's keynote speaking appearances into a lead generation machine, including an idea involving shipping his new book to every attendee who signs up that Mark reckons could hit a ninety percent conversion rate.

Mark saw the potential of online courses back in 2017 when he was project managing course builds at McKinsey. It took him a few more years to put all the pieces together. You can feel in this conversation that the pieces are finally there.

I think you'll enjoy this one.

Check out Mark's work:
📖 Mark's New Book, Mission Ready: https://www.panmacmillan.com.au/9781761902796/
🌐 LinkedIn: https://www.linkedin.com/in/mark-wales/
📸 Instagram: https://www.instagram.com/mark.a.wales/?hl=en
▶️ YouTube: https://www.youtube.com/@mark-wales

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Alicia Katz Pollock built something most course creators never think to build. She took QuickBooks training, a topic most people assume is dry and functional, and turned it into a tiered membership with over 50 courses, live community calls, a coaching program, five books, a podcast, and CPE accreditation that accounting firms actually require their staff to complete.

Dominik sat down with Alicia to trace how that happened. She started with a single beginner bootcamp, then kept adding courses every time a client asked about something new. Banking feeds, reconciliation, payroll, sales tax. Eventually she had enough that selling them one at a time felt expensive for the buyer, so she built a membership instead.

One thing Alicia said that stuck with Dominik: she fully expected members to stay one year and then leave once they'd worked through the curriculum. That didn't happen. People have been in the community for years, and when she asked why, the answer wasn't the 50 courses. It was the twice-monthly round-robin calls where members bring their real client problems and work through them together.

There's also a fascinating section on the four years she spent earning NASBA accreditation for CPE credits, what it took, and how it eventually opened the door to selling seats directly to accounting firms.

Alicia is honest, specific, and genuinely fun to listen to. I think you'll enjoy this one.

Check out Alicia's work:
🌐 https://royalwise.com/

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Milo Andreo built one of the biggest piano teaching businesses on the internet in Portuguese. Over a million subscribers, 26,000 students, a full course platform with a community, a music library, the works. Then he decided to do it all again, in English, from scratch.

Two years in, his English channel Easy Fast Piano is already past 170,000 subscribers and 10,000 students. And he's running both at the same time, producing videos in two languages every single week.

I had a great conversation with Milo about what that actually looks like. We got into his lead magnet system, where he creates a free PDF for every single video he publishes, which is now bringing in around 10,000 new email subscribers every month. We also talked about the difference between translating a business and actually adapting it, because Milo learned the hard way that the Brazilian market and the English-speaking market are not the same thing, even if the teaching content is identical.

Milo also shared how he's using AI across pretty much every part of his business and personal life right now. His answer when I asked where he'd found it helpful was just, "Everything. You name it, I'm using."

We also got into survey strategy, segmenting email lists by musical goals, and why long-form YouTube content converts to course buyers in a way that nothing else really matches.

I think you'll enjoy this one.

Check out Milo's work:
🌐 http://www.miloandreo.com
📸 http://instagram.com/@miloandreo
▶️ http://youtube.com/@miloandreo

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Lauren Bateman has 650,000 YouTube subscribers, nearly 900 videos, and over 58 million views teaching guitar to older beginners. She also survived cancer at 16, quit a pharmaceutical job in her twenties, opened a brick-and-mortar music school, and now runs the online side of her business with a small team of VAs and an editor. There is a lot going on.

What I loved about this conversation was how clearly Lauren has thought about the trade-offs in her business. She knows exactly why she will not do high-ticket coaching, exactly what kind of life she is trying to protect, and exactly what kind of teaching lights her up. Not many course creators at her level are this honest about what they want and what they are willing to give up to get it.

We also got into some real tactical detail. Lauren has two different sales pages with different headlines for different traffic sources, and she has the A/B testing data to explain why. I walked through what I think she could do to significantly increase revenue from her YouTube traffic, and she was genuinely open to testing it. The back-and-forth on email list strategy, lead magnets, and conversion rates was one of the more practical exchanges we have had on the show in a while.

And then there is the personal side, which surprised me a bit. Lauren said she has spent 20 years working toward a specific goal, and she has reached it. Now she is working with a coach to figure out what comes next. That part of the conversation stuck with me.

I think you will enjoy this one.

Check out Lauren's work:
🌐 https://www.laurenbateman.com/
📸 https://www.instagram.com/thelaurenbateman/
▶️ https://www.youtube.com/LaurenBateman

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Gabriel lost his job. While applying for new ones and getting rejected, he started teaching Spanish online and writing short stories for his students. The feedback was so good he thought, why not share this with the world?

Eighteen months later, his site Fluent with Stories is pulling in 250,000 visitors a month through SEO, adding close to 2,000 new email subscribers every month, and his debut A1 Spanish course launched to testimonials most creators would genuinely envy. And he's been taking it seriously for all of five months.

I sat down with Gabriel to talk through how he built all of this, what's driving the SEO traffic, how Amazon KDP became an unexpected lead generation engine, and where the gaps still are in his funnel. We also got into the tripwire conversation, single vs double opt-in, and why his sales page is missing the one section that could make a real difference to conversions.

Gabriel is one of those guests where you're just rooting for him the whole way through. He's humble, he listens to his audience, he builds what they ask for, and he has a genuinely different product in a very crowded niche. The bit where he talks about his readers begging to support him before the course even existed, that one stuck with me.

If you're early in building your course business and wondering whether the fundamentals actually work, this one is for you. I think you'll really enjoy it.

Check out Gabriel's work:
🌐 http://www.fluentwithstories.com