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Black Friday is the biggest revenue opportunity of the year for course creators, and the sellers who win it start planning in September. In this episode, John Ainsworth and Josip Bolina walk through the exact Black Friday playbook we use with our clients.

They cover why prep has to start in September, why Black Friday is the time to run your proven winner instead of testing new ideas, and how to build a dedicated offer for your best customers who already bought your main product. You'll also learn the two-promotion November strategy, how many emails to send and which types, and why the best offer beats the cheapest offer. Instead of slashing prices in half, a reverse discount that stacks bonuses on top of your existing product will usually make you more money. Plus: what to sell on Cyber Monday for the people who didn't buy, and the simple tracking setup you need.

In 2026, Black Friday is November 27 and Cyber Monday is November 30. Start now.

Want help with your Black Friday campaign? Email us:
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Nadia Mologova grew up in a mining town in southern Russia, spotted an art school at six years old while walking with her grandmother, and eventually made her way to Florence, Italy, where she founded her own accredited academy in 2009. She built the entire curriculum herself, from anatomy to composition to copying the old masters, and has spent 17 years passing on a method of classical art that most of the world had mostly forgotten.

John talked with Nadia about how the Florence Classical Arts Academy works today, with in-person students capped at 60 a year, online groups deliberately kept to 5 or 10 students, and a hybrid program that brings people to Florence to finish what they started online. The pricing, the hiring of professors, the challenge of giving individual feedback across 12 time zones, all of it came up.

What stood out was how clearly Nadia has thought through the tradeoff between scale and quality. She could take more students. She has chosen not to. That's not a marketing line for her, it's just how she thinks about the work. She also talked honestly about stepping back from day-to-day leadership, the weight of running something this complex alongside raising two children and pursuing her own art, including a recognition from the Olympic Committee in 2026.

If you're running a course business and thinking about how much individual support is the right amount to offer, this one gives you a lot to think about.

Check out Nadia's work:
🌐 https://www.artac.org
📸 https://www.instagram.com/nadyamolugova
▶️ https://www.youtube.com/c/FlorenceClassicalArtsAcademyart

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Louise Volschenk did her first bride's makeup at 14. She was charging the equivalent of about $10. By 16 she was teaching in salons. By 2013 she had turned her garage into an academy. Today she has nearly 100,000 followers, her own makeup product line, students flying in from other countries, and an online course she openly admits she has barely scratched the surface of.

Dominik sat down with Louise to trace the whole journey, from that garage studio in South Africa to a brand that is starting to reach people globally without really trying. What came through clearly is how much of Louise's business was built on personal connection, showing up as herself, talking to her audience, and being the face of what she built.

The moment that stuck with me most was when Louise described her email marketing, four newsletters a month, one per product or service area, and then said plainly that the online course is "income that I'm ignoring." Not said defensively, just honestly. She knows the opportunity is sitting there. She knows the course is already made. She just hasn't turned the tap on yet.

There's also a lot in here about what it actually takes to teach a skill well, why her students travel from other countries, what she'd tell her 14-year-old self, and why she thinks feeling stuck usually has more to do with watching other people than with your own work.

I think you'll enjoy this one.

Check out Louise's work:
🌐 https://www.halouw.co.za/
📸 https://www.instagram.com/louisevolschenk1/?hl=en
▶️ https://www.youtube.com/channel/UCART2AOrqc0y-k77k4M_U_Q

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Amanda Quinn built Canada's largest women's-only fitness company from a single bootcamp in a park in 2008. Then, a decade in, she and her co-founder Laura closed it down and started over, teaching other women to become certified health and nutrition coaches instead.

That decision turned into FitChicks Academy. In this episode, John sits down with Amanda to talk through how they actually built that, because the business model is more layered than it looks from the outside.

They get into her bonus strategy, which she thinks about in a way most course creators don't. Her paid and free workshops are converting at around 30% when people show up, and the bonuses are a big part of why. She also talks through a new $49 challenge funnel she's testing right now, built on the logic that getting someone to go from free to $49 is a very different ask than free to $3,000.

There's a good stretch on evergreen versus live funnels too. Amanda tried evergreen, found it was actually more work, and largely went back to live. But she has one certification that runs on a fixed monthly cycle and has converted consistently for two years, and she's not touching it.

She's also got bigger plans in motion: a self-coaching membership, a physical food product line, and a 1,000-person live event in 2027. It's a fun conversation with someone who's clearly been building for a long time and knows where she's going next.

Hope you enjoy it.

Check out Amanda's work:
🌐 https://fitchicksacademy.com/
📸 https://www.instagram.com/fitchicksacademy/

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Melissa Mae Dillon left her teaching job in 2022, shaved her head, got a pink and yellow mohawk, and started filming insurance exam prep videos on YouTube with zero editing. No fancy setup. No plan. One take, every time.

Her first year she made $126,000. Her courses now bring in $130,000 to $150,000 a month.

I sat down with Melissa to talk about how she built Insurance Exam Queen from nothing, but what I didn't expect was how little of the conversation would actually be about tactics. Melissa is clear that the most important thing she did to build her business was internal work, not funnels, not email sequences, not better lighting. She talks about hiring from guilt, creating offers from desperation and watching them attract desperate clients, and how she eventually figured out that the energy you're in when you build something leaves an imprint on everything that comes from it.

We did get into the practical side too. Her YouTube channel sits at 103,000 subscribers and drives almost all her top-of-funnel traffic. Her Facebook study group has 22,000 members who actively sell her course for her without being paid. She has 3,400 five-star reviews. And we walked through an eight-email welcome sequence together and worked out how it would fit her audience.

Melissa is one of those guests who makes you think differently about what the work actually is. I think you'll enjoy this one.

Check out Melissa's work:
🌐 https://melissamaedillon.com/
📸 https://www.facebook.com/melicious.pixie
▶️ https://www.youtube.com/@insuranceexamqueen

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Azhelle Wade spent years inside the toy industry, earning three patents, managing six brands at Toys R Us, and eventually reaching VP level. Then she walked away and started teaching complete strangers how to do what she used to do for a living.

Dominik sat down with Azhelle, known as The Toy Coach, to talk about how she built her audience from 20 podcast downloads per episode, how a chance meeting at an industry networking event sparked the whole thing, and what actually happened when TV appearances on NBC sent a flood of leads her way with no real funnel to catch them.

They get into the real business decisions too. How she used AI to role-play as her own ideal customer and audit her sales page, discovering she was trying to speak to too many different people at once. How she restructured Toy Creators Academy from a cohort model into a self-study program with a separate one-on-one offer. And how raising her price 2.5x turned around a period where she could not understand why nobody was buying.

There is also a student story in here that genuinely stopped me when I heard it. One of Azhelle's students, Samantha, came close to quitting after her factory fell through. Azhelle talked her back in. Samantha ended up on Dragon's Den and disclosed $465,000 in revenue last year, then told Azhelle the number was already higher.

It is a good one. I think you will enjoy it.

Check out Azhelle's work:
🌐 https://www.thetoycoach.com/
📸 https://www.instagram.com/thetoycoach
▶️ https://www.youtube.com/thetoycoach

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Nick Pezzopane spent 15 years doing motion graphics and animation for clients like Blizzard Entertainment and the History Channel. Then AI showed up, and instead of feeling threatened, he went deep. He taught himself to install and run open-source AI locally on his own machine, built custom setups for paying clients, and turned that knowledge into a course business called Pixel Pandorium Academy.

John sat down with Nick to dig into how he's building this from scratch, without a social following, using Meta ads as his primary traffic source. Nick's running one ad, spending around $1,000 to $1,500 a week, and has managed to break even on the front end while seeing roughly a 40% conversion rate on his $97 upsell. He's honest about what he got wrong with the ads early on and what he's still figuring out.

What made this conversation interesting was how clearly Nick thinks about the value he's delivering. His argument for running AI locally, cutting out subscription costs, removing censorship restrictions, and getting more raw processing power, is simple and compelling. You can feel how much he wants his students to actually succeed with this.

There's also a genuinely good moment near the end where Nick talks about waking up and realizing he's running a real business for the first time. It's the kind of thing that's easy to rush past, but worth sitting with.

I think you'll enjoy this one.

Check out Nick's work:
🌐 https://pixelpandorium.com
📸 https://www.instagram.com/pixel_pandorium/

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Simone, known as The Bearded Guitarist, spent over 15 years teaching private guitar lessons before he started posting on YouTube in 2020. He now has half a million followers across platforms. And until about a year ago, he had almost no idea how to actually sell anything.

That's the honest thing he said early in our conversation, and it set the tone for everything that followed. Simone has clearly put in the work since then. He's built out a sales page with a VSL, testimonials, bonuses, multiple guarantees, an order bump, and a post-checkout upsell. He launched a coaching program structured more like personal training than traditional lessons. He's grown his email list from around 1,200 to just over 4,000 in twelve months.

We went through his funnel together on screen, called out what he's doing well, and got into the specific things worth fixing: where to place the pain-agitation-solution section, why an eyebrow headline matters, and what's missing from his checkout page that's probably costing him sales.

The bigger conversation was about email. Simone is getting around 300 new subscribers a month right now. John thinks he can get that to 1,000 or more, and explains exactly how monthly email promotions, done the right way, become the engine that makes everything else work.

Simone is the kind of guest I really enjoy talking to. He's far enough along to have made real decisions and learned from them, and honest enough to say where he got it wrong. I think you'll enjoy this one.

Check out Simone's work:
🌐 http://thebeardedguitaristcourses.com
📸 https://www.instagram.com/its_thebeardedguitarist
▶️ https://www.youtube.com/@TheBeardedGuitarist

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Jessica Lackey has a Harvard MBA, worked at McKinsey, and spent years inside Nike watching the company chase scale until it broke. Now she runs a multi-six-figure business on a list of 2,000 people, more than one in ten of whom buys from her every year. And she built it that way on purpose.

Dominik sat down with Jessica to find out how that actually works. What came out of it was one of the more honest conversations we've had on this show about what the online course industry gets wrong and what it costs people who follow the standard playbook without questioning it.

Jessica talks about how she spent four years doing free monthly workshops without selling anything, how she personally emails everyone on her waitlist before a launch, and why she keeps her prices low on purpose so she never has to sell hard. She also gets into the moment she realized that most marketing advice isn't bad, it's just built for a different kind of business than the one most people are actually running.

There's a section about the pull she still feels toward bigger numbers and higher prices, and why she chooses not to go there even when she could. That part stuck with me. It's rare for someone to admit that so clearly.

She also shares two sharp pieces of advice: one for people who haven't launched yet, and one for people who've plateaued after two years. Both are worth hearing.

Check out Jessica's work:
🌐 https://www.deeperfoundations.com/
📸 https://www.linkedin.com/in/jessica-lackey/

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Leo Coelho trained as a doctor, worked in medicine for about a year, quit to become a digital nomad, tried translating, tried dropshipping, became a tour guide in Lisbon, and then the pandemic shut everything down overnight.

So he started making YouTube videos about the Portuguese language. Fifteen months later he had 100,000 subscribers. Today Portuguese with Leo is the biggest channel for learning European Portuguese as a foreign language, with 290,000 subscribers, 22 million views, and a course business doing low six figures a year at around 70% margins.

John sat down with Leo to talk through how he built all of this, and what he's working on next. They got into why Leo thinks YouTube consistency is overrated, how he keeps pulling in 1,500 new email subscribers a month without posting a video for nearly three months, and how his evergreen content does the lead generation work for him. Then the conversation shifted into something closer to a live strategy session, covering order bumps versus upsells, checkout page conversion, warm-up email sequences, and how to run promotions more often without burning out your audience.

Leo's got a clear north star, living and travelling on his own terms, and every business decision he makes runs through that filter first. That shapes everything about how he operates, and honestly it makes for a really interesting conversation.

Hope you enjoy it as much as I did.

Check out Leo's work:
🌐 https://www.portuguesewithleo.com
▶️ https://www.youtube.com/@PortugueseWithLeo