Podcast Summary: My First Million – "Brainstorming $100M AI-Proof Businesses"
Host: Sam Parr & Shaan Puri (HubSpot Media)
Date: August 26, 2025
Episode Overview
In this episode, Sam and Shaan brainstorm business ideas that are "AI-proof"—opportunities rooted in physical, social, and deeply human needs that technology and AI are unlikely to disrupt soon. The conversation revolves around social clubs, real estate, and products that lean deliberately “anti-tech,” exploring business models thriving on human connection and presence. Through lively banter, personal stories, and market research, they consider what makes businesses sustainable as society becomes increasingly digital.
Key Discussion Points and Insights
1. The Country Club & Modern Social Clubs
- [00:17-04:50]
- Shaan introduces the idea: Traditional country clubs, despite appearing old-fashioned, are lucrative and "AI-proof." He details country club economics—initiation fees, monthly dues, break-even F&B operations—all leading to a $20–25M ARR for a single club.
- Quote (Shaan, 02:02): “You pay something like $7,500 just to initiate, just to get your foot in the door... That’s not even the dues.”
- The value is access, status, and community—intangibles difficult for tech to replace.
- Examples cited: Soho House (recently taken private at $2.7B), The Battery in San Francisco.
- Shaan introduces the idea: Traditional country clubs, despite appearing old-fashioned, are lucrative and "AI-proof." He details country club economics—initiation fees, monthly dues, break-even F&B operations—all leading to a $20–25M ARR for a single club.
2. Operational Complexity & Risks of Physical Business
- [06:01-07:55]
- Sam pushes back: Hospitality and real estate are operationally intensive; online-first communities (like his company, Hampton) shouldn't always jump into physical space.
- Quote (Sam, 06:01): “My main business is creating wonderful core groups where people talk. And then this business…is hospitality and real estate.”
- References Chief (a women-focused executive club) that struggled due to real estate drag on finances.
- Sam pushes back: Hospitality and real estate are operationally intensive; online-first communities (like his company, Hampton) shouldn't always jump into physical space.
3. The Boom in Niche, Experiential Work/Social Clubs
- [06:51-10:03]
- Sam notes a surge of these hybrid spaces—work, social, community—especially among Gen Z and Millennials. Examples include:
- Zero Bond (NYC exclusive social club for 20-somethings)
- The Malin (boutique, design-focused coworking for “hot freelancers”)
- The Lighthouse (creator-focused coworking in L.A. doing 8-figures in its first year)
- New House (work/social hub for creatives)
- The ability to scale “cool” is difficult, but scaling utility (coworking) works well.
- Sam notes a surge of these hybrid spaces—work, social, community—especially among Gen Z and Millennials. Examples include:
4. AI-Proof Real Estate: Clubs for Families and Pet Owners
- [11:07-14:40]
- Beginning Clubhouse in Brooklyn: A “Soho House for families with kids”—tapping unmet parent needs.
- Live/Work/Play for Pet Owners in Denver: Pet amenities (dog parks, grooming, dog-walking) justify charging 30-40% more rent.
- Quote (Shaan, 13:43): “All real estate is just a question of can you buy it where everybody thinks it’s worth X...but you can do 1.3x, 1.2x, if you do that…You’ve increased the value of the building maybe by $10–12 million…”
5. The Value of Community: "Join or Die"
- [17:06-19:18]
- Sam references Bowling Alone: Declining club participation correlates with drops in social trust, voter turnout, and well-being.
- Possible club marketing tagline: “Join or Die”—emphasizing that real-world social connection is essential to health and happiness.
- Quote (Sam, 18:58): “...as AI and digital gets more popular, you crave human interaction more than ever, and you will literally live longer if you have a community...”
- Shaan finds the tagline “a little aggressive”: “Didn’t do it for me, but I’m sure there’s others who will like it.” (19:25)
- Sam references Bowling Alone: Declining club participation correlates with drops in social trust, voter turnout, and well-being.
6. Yondr: $300M Anti-Phone Pouch Business
- [20:32-26:12]
- Yondr (pouch that locks away phones at events to foster presence). Used at comedy shows, concerts (origin: Dave Chappelle), and now in schools.
- Quote (Shaan, 22:00): “Anytime the pendulum swings too far in one direction, it creates demand for the opposite.”
- 70%+ of revenue now from schools to enforce phone-free environments.
- Mixed emotional responses: anxiety, rage, but also recognizing its benefits.
- Quote (Sam, 25:01): “I feel rage and anxiety because I can’t get to my phone... Which means I need to use it more than I thought.”
- Yondr (pouch that locks away phones at events to foster presence). Used at comedy shows, concerts (origin: Dave Chappelle), and now in schools.
7. MFM’s “Phone Fast” Challenge
- [26:58-33:32]
- They propose a podcast listener challenge: 12-hour or 24-hour “phone fast”—no screens, no conversation, just solitude.
- Quote (Sam, 27:58): “I would bet my life that you can’t do that.”
- Observations on how difficult it is to focus deeply without digital distraction and the rare rewards of that focus.
- They propose a podcast listener challenge: 12-hour or 24-hour “phone fast”—no screens, no conversation, just solitude.
8. Daily Creative/Focus Habits
- [32:25-34:54]
- Both hosts share rituals for maintaining their creative and business productivity: “morning pages” before any input, dedicated phoneless time, carve out space for flow.
- Quote (Shaan, 32:13): “The biggest thing for me isn’t just the focus, it’s being pre-input to any Slack, Twitter, email, nothing...”
9. Compound Effect of Small Daily Actions
- [36:16-41:43]
- Sam is inspired by Robert Caro’s daily “1,000 words” routine, documented as a grid of strict writing discipline leading to an epic biography (The Power Broker).
- Quote (Sam, 39:08): “…greatness comes from a very simple process of 1,000 words every single day... that is a very bite-sized way of looking at an epic project.”
- Similar Steve Martin “banjo story”—commit to 40 years, not daily perfection.
- Sam is inspired by Robert Caro’s daily “1,000 words” routine, documented as a grid of strict writing discipline leading to an epic biography (The Power Broker).
- [41:43-46:47]
- Discussion on "impatience with action, patience with results"—the mental model of holding two extremes at once for success and sanity.
10. Dialectics: Holding Opposing Truths
- [43:48-46:47]
- Reference to dialectics—embracing contradictions (e.g., be both impatient and patient, generalist and specialist, legacy-builder and present-focused).
- Quote (Shaan, 44:49): “The wisest stance will incorporate both of the opposites within itself.”
- Reference to dialectics—embracing contradictions (e.g., be both impatient and patient, generalist and specialist, legacy-builder and present-focused).
11. Personal Learning & Curiosity as Renaissance Practice
- [48:17-54:09]
- Sam describes his "semesters" of obsession—delving deeply into new interests (recently: NYC architecture and beauty) and physically exploring, talking to experts.
- Quote (Sam, 50:08): “I tend to find something that interests me, and then I’ll create a semester around it... I immerse myself, and then I go out and talk to people about it.”
- Shaan: Embraces the joy and productivity of following curiosity, but admits to more scattered, improvisational research.
- Sam describes his "semesters" of obsession—delving deeply into new interests (recently: NYC architecture and beauty) and physically exploring, talking to experts.
Notable Quotes & Memorable Moments
-
On Social Club Economics:
“2,000 members times, let’s call it 10 grand a year… a $20 million annual recurring revenue business.” — Shaan [03:24] -
On Pendulum Swings in Society:
“Anytime the pendulum swings too far in one direction, it creates demand for the opposite.” — Shaan [22:00] -
On the “Phone Fast” Challenge:
“You can’t bring your phone or have a conversation with someone... I would bet my life that you can’t do that.” — Sam [27:33] -
On the Value of Small Actions:
“Greatness comes from a very simple process of 1,000 words every single day.” — Sam [39:08] -
On Holding Opposites:
“The wisest stance will incorporate both of the opposites within itself.” — Shaan [44:49]
Timestamps for Important Segments
| Timestamp | Segment | | ----------- | ------------------------------------------------------ | | 00:17 | Country club as $20M+ ARR AI-proof business | | 06:01 | Physical v. digital businesses: operational pitfalls | | 07:56 | Niche coworking/social club boom (Malin, Lighthouse) | | 11:07 | Opportunities in family/pet-oriented real estate | | 17:06 | Decline of clubs, rise of loneliness (“Join or Die”) | | 20:32 | Yondr: The $300M anti-phone pouch business | | 26:58 | MFM’s “Phone Fast” challenge (12/24 hours) | | 32:25 | Creative/phoneless focus habits | | 36:16 | Robert Caro’s daily 1,000-word method | | 41:43 | Steve Martin’s 40-year banjo story, patience/impatience| | 43:48 | Dialectics: Embracing contradictions to succeed | | 48:17 | Sam’s deep-dive curiosity “semesters” |
Flow and Tone
The episode maintains the classic energetic, bantering, and self-aware MFM style—balancing irreverent humor, business analysis, and personal anecdotes. It’s rich with pragmatic advice and examples, but never takes itself too seriously.
Summary
Sam and Shaan use the “AI-proof” lens to spotlight business opportunities anchored in physical experiences, community, and the human need for analog moments—even as society digitizes. They unpack how the renewed popularity of social clubs, hybrid coworking spaces, and anti-tech products like Yondr offer lessons for entrepreneurs seeking robust, resilient business models. The episode blends practical business insights with deeper reflections on focus, motivation, and human connection, embodying the spirit of “My First Million” at its best.