The Art of Selling Online Courses

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Ben Settle has been selling online since 2002. He runs a physical print newsletter called Email Players, prices some of his books above a thousand dollars, and has a sales page that actively tries to talk you out of buying. Dominik sat down with him to find out why any of that works.

What came out of the conversation surprised me. Ben's whole approach to email is built around one idea: proximity. The more often you show up in someone's inbox, the more they trust you, the more they remember you, and eventually, the more they buy from you. He's been sending daily emails for years and makes no apologies for it. His argument against mailing twice a month is hard to argue with: if people don't remember who you are, they hit spam. And at that point, you've done it to yourself.

He also talks through something most course creators never consider: the difference between a buyer and a customer. A buyer purchases once. A customer makes a habit of buying from you. His whole business is built around creating the second kind, which is partly why his sales page tells unqualified people to leave.

There's also a genuinely interesting section on where he thinks the AI wave is heading, and why he thinks right now is actually the moment to double down on relationships rather than automation.

If you're emailing your list twice a month and wondering why sales feel inconsistent, this one is worth your time.

Check out Ben's work:
🌐 http://www.bensettle.com/

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Freddie Fernandez spent 31 years at Miami Fire Rescue, retiring as a deputy fire chief overseeing 14 stations, 150 people per shift, and 250 emergency calls a day. Then he built a course business. No ads. No launches. No algorithm. Just word of mouth, challenge coins in the mail, and a $925 product that has reached 500 agencies across 47 states.

Dominik sat down with Freddie to figure out how that actually works.

What came out of the conversation surprised me. Freddie started teaching at 22 by volunteering to cover a canceled class for 30 veteran firefighters, with less than 24 hours' notice, on a topic he hadn't fully mastered yet. That same instinct, just jump in and figure it out, runs through everything he's built since.

His product ladder is worth paying attention to. He walks people into the right package based on timeline and need, not price. He'll actively steer someone away from his most expensive option if it's not what they need. And he thinks that's exactly why customers keep coming back, and why they send their colleagues.

His take on discovery calls is something I've been thinking about since we recorded this. He spends the first part of every call asking questions, not pitching. He says if you listen first, you can sell later, but only what they actually asked for.

Freddie also talked about refilming his entire course library in 2023, ten years after the originals, because he felt the material was getting stale. That kind of honesty about your own product is rare.

I think you'll enjoy this one.

Check out Freddie's work:
🌐 https://www.fireassessmentcenterprep.com/
📸 https://www.instagram.com/fireassessmentcenterprep
▶️https://www.youtube.com/channel/UCiCoJql6gw_KGQ7ZIS4fHfQ

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Yogi Aaron built a retreat center in the Costa Rican jungle, wrote a book called Stop Stretching, and developed a method that says conventional yoga is actually hurting people. That contrarian position came from a personal crisis: in his mid-40s, after decades of aggressive stretching, he was told he needed spinal fusion surgery.

John sat down with Aaron to talk about how he turned that moment into a business — Blue Osa Yoga Retreat and Spa, a teacher training program he's scaling toward $500K a year, two books, a podcast, and an audience of over 160,000 on YouTube.

What made this conversation interesting was how candid Aaron was about what isn't working. He openly shared that around 80% of people who book sales calls don't show up. He talked about pulling back from online courses because he believes people want in-person experiences more than ever. And he made a pretty strong case that if you're going to spend money on ads, remarketing is where to put it, because some of his customers follow him for five years before booking.

There's a lot in here about long nurture cycles, hybrid course models, Facebook and Google ad strategy, and what it actually takes to run a location-based business around a contrarian idea. Aaron is thoughtful, funny, and genuinely not trying to be anyone else in his space.

I think you'll enjoy this one.

Check out Aaron's work:
🌐 https://www.yogiaaron.com/ & https://www.theyogi.club/ & https://www.blueosa.com/ 
📸 https://instagram.com/yogi_aaron 
▶️ https://www.youtube.com/@yogiaaron 

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Finbar Horgan spent nearly seven years playing solo acoustic gigs up to seven nights a week in Edinburgh before he ever tried to sell a coaching program. No studio setup. No microphone. Just his phone, a Zoom account, and a free School community he ran for four months without charging anyone a penny.

Dominik sat down with Finbar to talk through how he built the Pro Gig Academy from scratch, starting with zero audience and an 800-subscriber YouTube channel, and growing it to 5,000 community members and 19,000 people on his email list. They got into the real mechanics of it: how his funnel actually works, why most of his serious buyers never join the free community at all, what finally pushed him to quit gigging full-time and go all in on coaching, and why he set up a separate YouTube channel just for testimonials.

There's a moment in this conversation where Finbar talks about showing up on discovery calls and having people say, "You don't need to pitch me, when can we start?" He explains exactly how he got there, and it has nothing to do with clever sales scripts.

He's also refreshingly honest about what isn't working yet, including how uncomfortable he still finds selling through email and why he spent five months after his March launch not promoting anything at all.

I think you'll like this one.

Check out Finbar's work:
🌐 https://www.skool.com/@finbar-horgan-5856
📸 https://www.instagram.com/finbarhorganmusic/
▶️ https://www.youtube.com/c/FinbarHorgan

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Courtney once sold a Christmas tree on Facebook Marketplace. Eight months pregnant, dragging trees out of her photography studio, a stranger asked if she could learn photography. Courtney handed her a discount code, and walked away having sold a course. That story says everything about how she sells.

Dominik sat down with Courtney, a professional family photographer in Australia who runs two businesses side by side: Blury Photography, where she shoots newborns and families, and Mum Nostalgia, where she teaches moms to photograph their own kids. She has a signature course, a brand new mini course, a podcast, three lead magnets, and a welcome email sequence. She is also studying psychology, and has small children at home.

What makes Courtney's approach unusual is that she deliberately uses her in-person photography business to sell her online courses, and it works because the trust is already there. She talked about why that matters, how she structures her two courses at very different price points, and what happened when she first launched and spent money on ads expecting the students to roll in.

She also shared something I thought was refreshing: she genuinely does not believe passive income is passive. Her words on that are worth hearing directly.

I think you'll like this one.

Check out Courtney's work:
Instagram: www.instagram.com/mamastalgia
The Art of Childhood Podcast: https://open.spotify.com/show/2GSRPWsWlBqCxuPKcgwOsd
Snap Mini-Course (learn photography from your phone): www.mamastalgia.co/snap
Don’t Say Cheese (learn photography on your big girl camera): www.mamastalgia.co/dontsaycheese

Use code ONLINE30 for 30% off either course.

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Julie Posluns started with a dog that lunged at children and bit skateboarders. That sent her back to university to study behavioral ecology. Then a black kitten turned up at her back door, started joining the dog training sessions, and Cat School was born.

John sat down with Julie to trace the whole journey: from her first Instagram post about cat tricks catching fire on The Dodo, to building a YouTube channel with 88,000 subscribers, to creating a membership structured like an actual school with five grades, badges, and graduation.

What makes Julie's story different from most course creators is the physical product sitting at the center of her business. She sells a clicker training kit on Amazon, with a QR code inside that leads to a free course, which feeds into the paid membership. It started because she said yes to a conference booth with nothing to sell, ordered tools to a hotel room in the States, and showed up with brown paper bags. It grew from there.

Julie is genuinely candid in this one. She talks openly about the gap between her free course and her paid membership, why she's invested more in the product than the school lately, and the capacity problem she hasn't fully solved yet. She also goes deep on something most course creators never think about: how the science of animal training and the science of teaching humans are, in her words, exactly the same.

It's a warm, honest conversation and Julie is great. Hope you enjoy it as much as I did.

Check out Julie's work:
🌐 https://www.catschool.co
📸 http://instagram.com/cat.school
▶️ http://youtube.com/catschool

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Jessica Russo Scherr holds a Fulbright Award, teaches Visual Art at one of the best international schools in Frankfurt, and somehow alongside all of that has built a gel plate printmaking course business that took around 2,000 students through her courses after launching in November 2024. She had no idea what gel plate printing was three or four years ago.

I talked with Jessica about how she got there and what the business actually looks like day to day. She runs five course launches a year and near-weekly live webinars where up to a thousand people show up to watch her demonstrate for 45 minutes, before she makes a short pitch and opens the floor for questions. She told me the webinars are some of the steadiest income she has, and that even selling two courses in a session feels like time well spent.

We also got into something she was honest about: she went in thinking this would be passive income. It has not been. It has required real, sustained work. And yet she has no plans to leave her teaching job, partly because she loves it, partly because she has a seven-sink art studio in Frankfurt and that, apparently, is non-negotiable.

Toward the end we worked through her email list growth, where I think there is a significant gap between what she is doing now and what is possible, and brainstormed what a lead magnet could look like for her niche.

I think you'll like this one.

Check out Jessica's work:
🌐 https://www.bluelavaart.com/
📸 https://www.instagram.com/bluelavaart
▶️ TikTok: https://www.tiktok.com/@bluelavaart
▶️ YouTube:https://www.youtube.com/bluelavaart
🌐 Newsletter: https://www.bluelavaartacademy.com/newsletter-form

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Annelies Espeel spent over 20 years treating patients in Brussels as a Chinese medicine practitioner and acupuncturist. Then she built an online masterclass, started running Meta ads, and found herself breaking even almost immediately. No backend, no upsell, no guarantee on the page. Just a solid product and a funnel that was halfway there.

In this episode, I sat down with Annelies and walked through her entire setup live. We looked at her sales page together, and she is already doing a lot of things right. She leads with the customer's pain, she has testimonials, she has an order bump that is actually converting. But there were some clear gaps, and we got into all of them. Headline placement, button copy written in the first person, adding a transformation section, why bonuses work best when they answer specific objections, and what an upsell could do for her return on ad spend.

What I found refreshing about Annelies is how honest she was about the learning curve. She came from Chinese medicine, not marketing. She said it plainly: "I have content, I just didn't see the wall behind it." That is such a common place to be, and she is already further along than she thinks.

If you are at the stage where your funnel kind of works but you are not sure why it is not scaling, this one is worth your time.

Check out Annelies's work:
🌐 www.sparkleyourvitalenergy.com
🌐
📸 instagram.com/anneliesespeel
▶️ https://kayanova.eu/en/sparkle-your-vital-energy/

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Monica Froese built a multi-million dollar Pinterest ads course business, then shut it all down in a single conversation with her husband right after they signed the papers on their new house. That alone would make for a good episode. But Monica's story keeps going.

After pivoting to Empowered Business and launching her Digital Shop Experience to what she describes as her biggest launches ever, her marriage fell apart. She pulled back from the business, turned off her paid ads, and by 2024 her revenue had halved. Then in 2025 it halved again.

I talked with Monica about how she rebuilt from that. Not through a dramatic new launch or a big moment of inspiration, but through AI. Specifically, agentic AI. She talks about how tools like Claude, Fable 5, and MCPs allowed her to take back work she'd previously hired out, update a spreadsheet she'd been selling for ten years but never had time to improve, and relaunch a brand she'd been sitting on since 2013.

We also got into the lifetime updates problem, how she's rethinking course pricing as AI changes so fast, and the question she asks every new creator that stops them cold: what are you growing your audience for?

Monica is honest about the hard parts in a way that most people aren't. I think you'll get a lot out of this one.

Check out Monica's work:
🌐 https://monicafroese.com
🌐 https://www.skool.com/empowered-ai-collective/about 
📸 https://instagram.com/monica.froese 
▶️ Empowered Business Podcast® https://monicafroese.com/podcast 

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Chandeep Chhabra left his job as an investment banking analyst in December 2013 with no backup plan and one idea: that he could sell his spreadsheet skills. Over a decade later, he runs Goodly, a business built around teaching Excel and Power BI to data professionals, with 137,000 YouTube subscribers, over 19 million views, corporate training clients, a consulting agency, and a bestselling book on Power Query.

John sat down with Chandeep for what turned into a live audit of his business. Chandeep has roughly 350,000 YouTube views per month and an email list of about 26,000 people, but only around 500 new subscribers joining each month. John walked through exactly why that gap exists, what his opt-in pages are doing wrong, where the lead magnet link is buried in the video description, and what changes would get that number to 3,000 or 4,000 new subscribers a month.

They also got into Black Friday. Chandeep went from $20,000 to $60,000 in Black Friday revenue after adding webinars and a more structured email sequence. John connected him with his head of funnel strategy to take it further.

And then the conversation drifted somewhere unexpected: writing books. Chandeep is working on his second, and both he and John reflected on why it's so hard, why you should publish anyway, and why Chandeep thinks books are written for craft and authority rather than money.

It's a really honest conversation, and I think you'll enjoy it.

Check out Chandeep's work:
🌐 http://products.goodly.co.in
📸 https://www.linkedin.com/in/chandeepchhabra/
▶️ https://www.youtube.com/@GoodlyChandeep