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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

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Lindsay Müller built a Facebook group of 30,000 ukulele beginners without spending a single dollar on ads. She did it by showing up every day for five months, posting chord sheets, tutorials, and tips on a simple rotating schedule she made up herself. Then one day in January 2024, it just took off.

Dominik sat down with Lindsay to talk through exactly how she built that, and what she did with the audience once she had it. She walks through her posting system, how she turns free chord sheets into email signups, and why she deliberately teaches so much for free inside the group rather than gating it behind a paywall. Her logic is simple and it works.

There's also a really honest stretch of conversation about high-ticket offers. Lindsay is pretty much the only guest we've had who's looked at that whole world and said, that's just not for me, and then made a clear case for why it doesn't have to be. She's been at this for two and a half years, she's found something that works, and she's not pretending to have it all figured out.

Oh, and her children's song Grateful Heart just crossed a million streams on Spotify. She wrote it for a challenge and almost didn't record it. That story is worth hearing too.

I think you'll enjoy this one.

Check out Lindsay's work:
🌐 http://LindsayMuller.com/Ukulele
📸 http://instagram.com/ukelindsay
▶️ http://youtube.com/LindsayMuller

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Shelley and CJ Hitz have run the same low-ticket membership for over eleven years. That alone is worth paying attention to.

They built Christian Book Academy for Christian writers, people who want to finish and publish their books but keep getting stuck. The membership costs $49 a month. They have over 300 members. And they have had to figure out, the hard way, what actually keeps people paying month after month.

Dominik sat down with both of them to dig into the mechanics. They talked about how they get 20 to 25 new paying members from a virtual conference twice a year, with no ads, just speakers emailing their lists. They talked about progress pods, small accountability groups inside the membership that have become so valued that one member's pod literally paid her subscription so she could stay. They talked about why removing the countdown timer on their conference offer tanked sales. And they were honest about the moments they almost walked away.

There was also a moment I did not expect. They turned down a spot in a book that hit the USA Today bestseller list because the topic did not fit their brand. No hesitation. They would do it again.

If you run a membership, or you are thinking about starting one, this conversation gets into the real economics in a way most people do not talk about publicly. I think you will get a lot from it.

Check out Shelley and CJ's work:
🌐 https://www.trainingauthors.com/
📸 https://www.facebook.com/kingdomwriterspage/
▶️ https://www.youtube.com/@kingdomwriterstv/

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Alain Picard spent years saying no to teaching. He believed, genuinely believed, that those who can't do, teach. It took a recession, a pregnant wife, no commissions, and his German wife looking him in the eye and saying "you're burying your gifts in the ground" to change his mind.

That one conversation set off a chain of small yeses that eventually led to a membership community called Cultivate, three instructional art books, a YouTube channel, about 25,000 people on his email list, and a business built entirely around helping pastel artists transform.

Dominik sat down with Alain to pull apart how all of it actually happened. They talked about why "if you build it, they will come" is a lie for artists, how free YouTube content around simple questions like "what pastels should I buy" became his most powerful list-building tool, and how he structures Cultivate so that students enter through a signature course and stay for the community.

There was also a really good thread about what Alain calls the tyranny of the urgent, the idea that if you only ever respond to the small fires, you never build anything that matters. He's lived that tension for thirty years, and the way he describes it is worth your time.

If you're a course creator who feels like your identity is tangled up in your results, or you're stuck at a revenue plateau and not sure what to try next, this one is for you.

Check out Alain's work:
🌐 https://www.picardstudio.com/
📸 https://www.instagram.com/alainpicard/
▶️ https://www.youtube.com/channel/@UCWyF5CvAv8c0oP4M5gWBaFA

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Billy Seol built his coaching business from Reddit. Not ads, not a big launch, not a personal brand with a large following. He started by showing up where people were already suffering and saying something useful. That's the whole philosophy in miniature.

Dominik sat down with Billy, a Buddhist life coach and former software engineer, to pull apart some ideas that don't get much airtime in the online course world. Billy's central argument is that most people who say they want success actually don't, not because they're lazy, but because success is a black box. They've never defined what their inner experience of it would actually feel like. And so, unconsciously, they steer away from it. It's the same reason a smoker keeps saying they want to quit.

What stuck with Dominik in this one was the confrontation piece. Billy deliberately activates his clients emotionally during sessions, and then asks them to look at themselves in that state. His reasoning: the person who shows up when you're stressed, defensive, or triggered is the person running your business. If you never see that person clearly, your business keeps replicating their behavior.

They also got into resonance direction, Billy's way of thinking about marketing funnels as one continuous emotional throughline rather than disconnected pieces, and his practical advice for anyone who's plateaued: are you selling to the list you already have, or just watching it grow?

I think you'll get a lot out of this one.

Check out Billy's work:

🌐 http://julylifecoach.com

📸 https://instagram.com/july_lifecoach

▶️ https://www.youtube.com/@Julylifecoach

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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