May 1, 2024 · 1h 3m · startup-ideas
This legend gave away 3 crazy cash-flowing business ideas
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Entrepreneur Jonathan Courtney joins host Greg Isenberg to pitch unconventional, cash-flowing startup concepts and share direct-response playbooks for building profitable, bootstrapped businesses.
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 22.5% of the talking time here. How this is scored →
Greg as informed peer 4.4 Guest teaching 3.9 Guest disagreement 1.7 Greg pushing back 1.8
speaking balance: gold is Greg, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 43:52 Jonathan forcefully rejects Greg's skepticism on masterminds
Jonathan cuts in with an explicit 'I disagree with you' when Greg dismisses high-ticket masterminds as overpriced hangouts, defending paid access to elite mentorship.
Hardest push from Greg ▶ 43:11 Greg challenges the legitimacy of paid mastermindsGreg questions the entire value proposition of paid mastermind communities, declaring he would never charge peers tens of thousands of dollars just to interact with him.
Biggest teaching moment ▶ 44:00 Jonathan details the math and ROI of paying for mentorshipJonathan breaks down how paying $36k to Sam Ovens and consulting Blake Lagrange immediately enabled a price increase from $3k to $9k, completely changing Greg's stance on the model.
Greg holds their own ▶ 31:13 Greg details retreat-driven user acquisition and niche dating appsGreg demonstrates insider knowledge by breaking down the market positioning of Feeld, Raya, and Beyond, explaining how physical retreats operate as the primary growth engine.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Greg as informed peer | Guest teaching | Guest disagreement | Greg pushing back | Why |
|---|---|---|---|---|---|---|
| Startup Idea #1: The AI-Powered Deep Brown Noise Sleep Device | 3 | 4 | 2 | 1 | Jonathan pitches an AI-driven deep brown noise sleep hardware device, explaining acoustics and acoustic masking. Greg engages constructively as a fellow sleep-tech enthusiast sharing his Eight Sleep scores. | |
| Hardware Aesthetics, Swedish Design, and Adult Engineering Strategy | 6 | 2 | 2 | 3 | Greg shares insights from Founders Inc about rapid AI hardware prototyping and references Teenage Engineering's aesthetic. He steers the banter toward competing directly with Teenage Engineering under the moniker Adult Engineering. | |
| Startup Idea #2: Sophisticated Male Pleasure Brands | 5 | 2 | 1 | 1 | Jonathan proposes premium, non-creepy male pleasure products akin to high-end design brands. Greg supports the thesis by drawing a parallel to how MedMen elevated cannabis retail into an Apple-like store experience. | |
| Startup Idea #3: Non-Spiritual Sex-Positive Retreats and Community | 6 | 2 | 1 | 1 | Jonathan identifies a market gap for non-spiritual, practical sex-positive retreats. Greg demonstrates domain expertise by introducing the Beyond app and explaining how private curated retreats function as high-conversion acquisition funnels. | |
| Startup Idea #4: Tackling Digital Addiction with Brick and Zero Frameworks | 4 | 4 | 1 | 1 | Jonathan highlights the hardware utility Brick and suggests combining physical friction with fasting app Zero's educational model for digital addiction. Greg prompts an explanation of Zero while validating his own daily Brick usage. | |
| The Direct-Response Playbook for Digital Detox | 4 | 5 | 1 | 1 | Jonathan outlines his bootstrap direct-response marketing blueprint: YouTube keyword research, remaking top-performing low-subscriber videos, lead funnels, and B2B corporate training. Greg agrees on the growing appeal of avoiding the VC treadmill. | |
| The Reality and ROI of High-Ticket Masterminds | 4 | 7 | 4 | 4 | Greg expresses skepticism toward paid high-ticket masterminds, calling the business model weird. Jonathan firmly pushes back, detailing how a $36k mastermind with Sam Ovens and consulting with Blake Lagrange generated millions by repositioning products. | |
| Direct Response Secrets: Russell Brunson and Automated Webinars | 3 | 6 | 2 | 2 | Greg probes why anyone should look past Russell Brunson's aggressive marketing reputation. Jonathan breaks down how automated webinar funnels from Expert Secrets generated $50k in 90 minutes and over $1M in year one. | |
| Bootstrapping Profitable Cash-Flow vs. Chasing Unicorns | 5 | 3 | 1 | 2 | Greg challenges Jonathan's self-deprecating description of running a mere 'small business,' emphasizing that high-margin multi-million-dollar cash flow is elite. Jonathan clarifies his focus on lifestyle operations over VC-backed exits. |
Statements from this episode (14)
Isenberg: 20VC recorded an episode with me that never aired
“That was the 20 VC podcast. Which I didn't, I wasn't, it didn't air, so.”
Courtney: AJ&Smart's top product generated up to $20M in revenue
“The most one of our products has ever made. We're just doing the calculations of it is like, 18 to twenty million dollars.”
Courtney: AJ&Smart charges 3x to 4x competitors for corporate facilitation training
“We just launched something which could not be more boring on paper. A facilitation in-person facilitation training, essentially for mainly for corporate employees. And we repackaged it in a way that no one else in the industry is doing it completely like at a …”
Courtney: Huge market opportunity for non-creepy male sex toys
“I genuinely think there's an entire market out there for sex toys. I don't know what pleasure self-pleasure devices for men that is like as big a thing as it is for women, but just not creepy and not weird”
Isenberg: MedMen succeeded by creating the Apple Store of cannabis
“The cannabis industry actually did a really good job of taking something that was like, Pretty like it was for stoners and stuff like that. And then in LA, there was this company called med men, which basically created like the apple for cannabis stores.”
Courtney: Huge market for retreats without spiritual or psychedelic elements
“I feel like there's a place in the market for looking at things which are usually mixed with psychedelics and usually mixed with meditation or yoga and removing those elements and making it more practical.”
Isenberg: Curated retreats drive strong user acquisition for community apps
“These retreats are actually a really good way for user acquisition and getting really be stoked about what you're doing.”
Courtney: Huge market for a digital detox brand paired with hardware
“I think there's a huge space in the market for a company to come along and be essentially the digital, you know, like the product zero for fasting, something like zero. But paired with something like Brick.”
Courtney: YouTube algorithm favors viral videos from low-subscriber channels
“If you find a video that has a lot of views, but very few subscribers, that's something that YouTube really likes. And so you want to remake that video essentially.”
Courtney: Product built in Sam Ovens' mastermind remains our top earner
“Previously I was in Sam Ovens Mastermind for three years. And Sam Ovens, maybe within the first or second day of being in the Mastermind changed literally. Like I joined in like, let's say on a Tuesday, the following Tuesday, I completely rethought everything …”
Courtney: Mastermind advice led AJ&Smart to triple product price and sell out
“The current mastermind I'm in is actually one of the members of the, of Sam ovens mastermind, a guy called Blake Lagrange and the product we just launched the full stack facilitator. We wanted to launch this for 3000 or 4000 euro or something like that. 1:30 m…”
Courtney: Russell Brunson's Atlas is the best mastermind for info products
“It's Russell Brunson's top level mastermind called Atlas. Only 15 people are in it. I don't think there's a better, again, we're talking about the info product space. We're talking about marketing. We're talking about direct response marketing and copywriting.”