Oct 20, 2025 · 42m · startup-ideas
Make $1M+ in 2026 with this Trend (IRL is back)
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Host Greg Isenberg and entrepreneur Jonathan Courtney discuss how founders can build seven-figure businesses by capitalizing on anti-trends, specifically using high-ticket in-person masterminds and physical products to build competitive moats against AI saturation.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Greg holds 18.2% of the talking time here. How this is scored →
Greg as informed peer 4.4 Guest teaching 6.0 Guest disagreement 1.6 Greg pushing back 1.7
speaking balance: gold is Greg, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:38 Jonathan self-deprecatingly rejects YouTube conventional norms
Jonathan dismisses typical YouTube optimization playbooks, joking that his own channel is a complete disaster because he refuses to follow standard video trends.
Hardest push from Greg ▶ 12:48 Greg halts Jonathan on contradicting his own in-person ruleGreg immediately stops Jonathan's explanation when Jonathan says to make events 'exclusively virtual,' forcing him to clarify that he meant strictly in-person.
Biggest teaching moment ▶ 30:45 Jonathan explains the psychology of physical artifacts over free PDFsJonathan breaks down how physical binders command thousands of dollars in value because unread digital PDFs get dismissed as low-value AI commodities.
Greg holds their own ▶ 15:36 Greg outlines the flywheel of IRL communities funding softwareGreg demonstrates his startup expertise by connecting in-person community building directly into an efficient cash engine to fund and distribute software products.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Greg as informed peer | Guest teaching | Guest disagreement | Greg pushing back | Why |
|---|---|---|---|---|---|---|
| The Anti-Trend: Capitalizing on In-Person Experiences Amidst Digital Fatigue | 4 | 6 | 1 | 1 | Greg sets the framing based on his social media post on digital fatigue, while Jonathan educates on his real-world pivot from $6k virtual certifications to $15k in-person events that sold out immediately. The dynamic is highly collaborative with Jonathan delivering deep tactical examples. | |
| The Saturation of Digital Communities and the Shift to Physical Moats | 5 | 4 | 2 | 2 | Greg provides structure by synthesizing how online communities became saturated like mobile apps, and Jonathan agrees while highlighting how in-person creates an unassailable moat. The tone remains humorous and collegial. | |
| Case Study: Designing and Selling Out Summer Camp Masterminds | 4 | 6 | 2 | 3 | Jonathan breaks down his Summer Camp mastermind playbook, detailing how removing digital/recordings created genuine scarcity and generated $6,800 ticket sales. Greg interjects to clarify points when Jonathan accidentally misspeaks about virtual versus in-person formats. | |
| Using In-Person Gatherings as Brand Catalysts and Software Funnels | 5 | 6 | 1 | 2 | Greg suggests using IRL communities to fund software and SaaS, which Jonathan validates with ClickFunnels and Tony Robbins case studies before walking through renting an entire Italian village. Greg pushes for the specific mechanics of selling out without relying solely on huge followings. | |
| The Execution Playbook: Direct Outreach, Tangible Targets, and Trust | 4 | 7 | 2 | 1 | Jonathan lays out his direct DM outreach process for filling events before financial commitment and demonstrates how low-audience creators can easily monetize. Greg listens as Jonathan breaks down the legitimacy and aspirational anchor provided by physical events. | |
| Physical Artifacts in the AI Age: Hormozi Playbooks and Tangible Value | 5 | 7 | 2 | 1 | Jonathan uses Alex Hormozi's physical playbook folder as an artifact to explain why tangible media commands premium pricing in the AI era. Greg connects this back to the broader macro anti-AI thesis. | |
| Structuring a Greg Isenberg IRL Mastermind and Risk-Free Guarantees | 4 | 6 | 1 | 2 | Jonathan pitches Greg on running his own high-ticket intimate mastermind and explains how he uses a Tony Robbins-style 100% money-back guarantee without refunds. Greg engages constructively on pricing and potential locations. |
Statements from this episode (18)
Courtney: Doing the exact opposite of AI trends is a massive opportunity
“I think that there's a massive opportunity or lots of massive opportunities to take a look at what's happening in the AI space, the social media space, the content space, just go the opposite way. And you're going to find that a lot of people want exactly that…”
Courtney shifts profitable digital products to hard-to-scale in-person experiences
“Over the last year, I've been moving a lot of the digital elements of my company, which are very profitable and scalable because they're digital to a much less easy to do in person version of these products.”
Courtney sold out three $14,300 in-person certifications immediately post-COVID
“Two years ago after COVID, I had the feeling people would want to come back in person. I had the feeling that that would also help us stand out because no one else was doing it. Everyone was still doing remote. And so we released a version of the certification…”
Isenberg: 'A community for that' is the new 'an app for that'
“Basically XYZ community for that is the new app for that.”
Courtney predicts in-person revenue will surpass online revenue by 2026
“But I think that that's going to change within the next two years and they're going to flip.”
Courtney sold 30 tickets at $6,800 for his mastermind event
“Charged 6800 per ticket and sold 30 tickets. So this was a, and those are the easiest 30 tickets I've ever sold in my life for anything, even though it's a lot more expensive than maybe what the others were charging for the digital version of it. And so I ran …”
Courtney: Inherent physical scarcity makes in-person events easier to market
“In person events actually have a limited amount of tickets. And so it's way easier to create a true sense of urgency and scarcity because it just is inherent to in person. And so these things are just so much easier to build campaigns around.”
Courtney calls industry conferences a money sink compared to boutique events
“I think conferences are generally like a money sink. Like I please do not think I'm talking about conferences. I'm really not. Conferences are like a completely separate thing”
Courtney launched a $6,000 subscription bundled with a five-day annual meetup
“We also launched a new product a couple of days ago, which also has this thing called campfire where once per year, we all meet up in person for five days. And that was never naturally part of our product. So it's a virtual product. Which has a one, a 12 month…”
Courtney: ClickFunnels uses in-person events to fund and sell software
“This is what click funnels do. They run these events and the goal of the, these events is to fund their software that they then sell to more people at the events. And it's like this very circular thing.”
AJ&Smart sold out an Italian retreat in two days at $7,800
“I announced this and people, it sold out in like two days. The tickets were like 7800 dollars because it was so expensive to rent out the space.”
Courtney: 1,000 podcast listeners can fill two high-ticket annual retreats
“I only have like 1000 people or 1000 to 2000 people listening to my podcast. And all my podcast is the only audience for the people coming to my other in-person events. And still I can fill, you know, one to two, 35 people events per year and add a high ticket…”
Courtney: Physical curation gains massive value as ChatGPT commoditizes digital knowledge
“And also, especially now that you can essentially generate all of that stuff on ChatGPT and knowledge is becoming less and less valuable. The ability to have something curated for you physically, in my opinion, is becoming more and more valuable.”
Courtney paid $5,000 just for Alex Hormozi's physical playbook folder
“I spent 5000 dollars only for this folder.”
Isenberg: Best paths to $1M are GPT wrappers or IRL masterminds
“If I was trying to make my first million dollars right now, I'd either build some GPT wrapper, or I'd build this.”