My First Million Podcast: "Giving Founders Brutally Honest Feedback"

Hosts: Sam Parr, Shaan Puri
Date: September 3, 2025

Overview

In this episode, Sam and Shaan dive deep into the art of honest feedback for founders, dissecting common entrepreneurial traps, brainstorming new business ideas, and exploring emerging trends in education and nostalgia-driven products. They sprinkle in personal stories, practical frameworks, and actionable insights—always with their signature mix of brutal honesty, humor, and energy.

Key Discussion Points & Insights

1. Common Traps for Founders: The Utah Emissions Startup

• Sam recounts a lunch with blue-collar founders running a mobile emissions ("smog check at your house") business. He identifies three major pitfalls most founders fall into:
  • Writing Off Growth Channels Prematurely
    • The founders dismissed Google Ads, claiming “it didn’t work,” but upon probing, Sam discovers they never tracked data or truly iterated on it.
    • Quote:
      “It’s like, damn, you have written off what’s probably the most obvious growth channel with this internal narrative of we tried that, it didn't work… I'm very skeptical of now.”
      (Sam, 03:57)
    • Sam’s framework: Write down exactly what you tried, what happened, and interrogate your own answers using a “Socratic” self-interview in a Google Doc.
      “Writing is sort of like an exposing function. Writing forces clear thinking.” (Sam, 07:39)
  • Not Dogfooding Your Own Product
    • Always mystery shop your own service (or use tools like Usertesting.com). Sam spot-checks their Google presence and website—they’re not clear on their value prop and lack reviews.
    • Quote:
      “Face the pain. Most entrepreneurs don’t actually face the pain. The problem is most likely right there on your site in your core flow… You’re just not clear enough, not compelling enough, or not visible enough.” (Sam, 10:59)
    • Story: Sam’s mom became a tester at Usertesting, made $100K from stock, now enjoys retirement from these digital side hustles.
  • Scaling Before Nailing
    • The founders ask if they should expand to more counties or fix their core funnel.
    • Advice:
      “Make the system work and then replicate it… Typically, if one path feels less painful, it’s usually the wrong one.” (Sam, 11:59)
    • Heuristic: If two options seem equal but one feels easier, beware—it’s likely “pain avoidance,” not true strategy.

2. The Decision-Making Muscle

• Invest in your judgment:

  • Writing and self-questioning expose cognitive biases and force clarity.
  • Impacts of state-of-mind: Sam notes how being sick, tired, or unwell can drastically reduce decision quality.
    • Quote:
      “Dude, making decisions when you’re sick… is probably, I don’t know, five times worse… it’s not a good time to be making good decisions.” (Sam, 14:15)
  • Recommended tool: Regularly step back and analyze what really works for your own decision-making.

• On learning (and mis-learning) from failure:

  • Shaan shares the importance of asking if you’ve actually learned the right lesson from an experience.
    • Quote:
      “‘Are you sure that’s the right lesson you should take away from this situation? Did you learn the right thing?’… Most people… didn’t really learn. Or if they learned, they learned the wrong lesson.” (Shaan, 18:25–19:05)

3. Business Opportunities & Trends

A. Physical Print: The Return of the Zine-Newsletter

• The Onion's Print Comeback:
  • Added 50K print subscribers in a year ($6m/year revenue)—proving nostalgia and physical media’s enduring appeal.
• Opportunity: High-end, deliberately “homemade” or “punk rock” print newsletters for high-net-worth individuals or tech execs.
  • Sam describes his “info-diet binder”: Personalized, curated printouts of the best essays, letters, and science articles sent monthly.
  • Quote:
    “Magazines are incredibly interesting... I would call it a newsletter, not a magazine. Literally on white paper, stapled together with like 10 or 20 sheets and put into an envelope.” (Sam, 25:43)
  • Possible MFM Product: A physical curation of their best content, insights, and recommendations for $1,000 a year.

B. Nostalgia & “Old School” Experiences

• Milk Delivery Services: (Oberweis Dairy case)
  • Shaan pitches a comeback for glass-bottle milk delivery, targeting millennials’ nostalgia and focus on premium, local foods.
  • Sam is skeptical of the logistics but bullish on premium niches (“rich, high-quality dairy” as a brand).

C. Purple Cows & Differentiation

• The metaphor of runners doing marathons in blue jeans—a “purple cow” moment, or standing out by doing something remarkable/different.
  • Quote:
    “If you split test everything… you end up with pornhub… At some point, you need to take a stand and you want to be different.” (Sam & Shaan, 21:02)

Alt-Schooling, AI, and the End of Standardized Education

Alpha School & AI-Powered Personal Education

• Who’s Joe Lamont?
  • Software billionaire, Trilogy Software founder, now invested $1B into Alpha School, a radical Austin K-12 school.
• Theory: The world's greatest achievers had intense, personalized early mentorship—not broad, generalized schooling.
• Practices:
  • Only 2 hours/day on AI-mediated iPad learning, yielding twice the knowledge of traditional school.
  • Rest of the day: “life skill” workshops, public speaking, entrepreneurship, outdoor challenges.
  • Quote:
    “The idea is… any kid with a tablet can have a tutor fully designing custom lesson plans… perfectly tailored to their level.” (Sam, 43:43)
  • Learning science: True mastery = 90%+ comprehension, not passing with a “C”. AI lets you test, remediate, and accelerate individually.
• Examples:
  • Second graders training (step-by-step) to run a 5K under 35 minutes—all succeeded.
• Technology:
  • Custom app (“Time Back”) with always-on camera and “waste meter” to monitor engagement.
• Sam: “I believe… someone is finally going to build a system that’s vastly better than school. This is the best bet I’ve seen.” (Sam, 54:51)

Contrasting Philosophies: Nature School & Sports Academies

• Shaan’s take: Not all will want AI school—many parents seek the opposite (nature schools, less tech, more life experience).
• Sam’s brother-in-law’s “Grind Academy”:
  • Private Vegas school combining homeschool-style academics with intensive athletic training (IMG Academy for middle-schoolers).
  • Early cohort: 40 kids at $5–7K/year (growing to $20K/year).
  • Quote:
    “He just got tired of… school was too slow, too boring, and not relevant to what's going on in the world today.” (Sam, 62:55)

Reflections on Changing Education & Social Upheaval

• Shaan: Modern high school is radically different from the past; today’s kids face pressures (tech addiction, social media, AI) that parents can barely comprehend.
• Sam: As an immigrant, his parents couldn’t relate to his upbringing—so adapting and experimenting is inevitable.
• Advice:
  • “The current system is so bad, the risk of trying something new is low. None of these choices are permanent and you can always switch if it doesn’t work out.” (Sam, 66:52)

Notable Quotes & Time Stamps

• “I’m very skeptical of ‘it didn’t work’… so few people truly try things to the point where they got a definitive answer.” (Sam, 03:57)
• “Writing is sort of like an exposing function. Writing forces clear thinking.” (Sam, 07:39)
• “Most entrepreneurs don’t actually face the pain… it’s right there on your site.” (Sam, 10:59)
• “A smart man does first what a dumb man does last.” (Shaan quoting Munger, 12:33)
• “Dude, making decisions when you’re sick… is five times worse.” (Sam, 14:15)
• “Are you sure that’s the right lesson? Did you learn the right thing?” (Shaan, 18:25)
• “If you split test everything, you end up with pornhub… At some point you need to take a stand.” (Sam & Shaan, 21:02)
• “Magazines are so interesting… I would call it a newsletter… white paper, stapled together… in an envelope.” (Sam, 25:43)
• “The idea is… any kid with a tablet can have a tutor designing custom lessons… perfectly tailored.” (Sam, 43:43)
• “I believe that they're going to be able to do this. I believe that if someone with a billion dollars and a 300-person AI lab is working on this, something will change.” (Sam, 54:51)
• “Current school experience is pretty dissatisfying… so the risk of trying something new is low.” (Sam, 66:52)

Important Timestamps

• [02:32] The Emissions Startup & Growth Traps
• [03:57] Unpacking “It didn’t work” with Google Ads
• [10:59] Dogfooding and Usertesting.com anecdote
• [12:33] Munger quote: “A smart man does first what a dumb man does last.”
• [19:05] Learning the right lesson from failure
• [21:02] The “purple cow” analogy and the pitfalls of endless A/B testing
• [25:43] Business idea: physical, high-priced zine-newsletter
• [31:33] Milk delivery and nostalgia-based businesses
• [43:23] Bloom's Two Sigma problem & individual tutoring with AI
• [52:12] Mentava app: teaching kids to read with digital mastery tracking
• [54:51] Alpha School as a scalable, radical improvement on traditional education
• [62:55] Private athletic/academic “Grind Academy” in Las Vegas
• [66:52] The logic of trying alternatives to the status quo in education

Memorable Moments

• Sam’s mom’s $100K retirement from becoming an early Usertesting.com participant.
• Debate on the wisdom of scaling before fixing your funnel—with references to painful real-world missteps.
• Brainstorming a “white paper, stapled newsletter” as an ultra-premium curation product.
• Detailed, first-hand explanations of cutting-edge education models—both tech-forward (AI) and “back-to-roots” (nature/sports).
• Personal schooling stories—Catholic nuns, scheduled high school fights, and moving to rich-kid schools in Beijing.
• A gentle existential panic about how to parent in a world changing faster than anyone can keep up.

Tone & Style

Sam and Shaan are candid, playful, and thoughtful—never shying away from calling out BS or sharing their own failings. Their banter weaves personal anecdotes with frameworks and theory, making even their brainstorming sessions highly actionable for listeners.

If you're a founder, operator, parent, or just hungry for fresh business and life ideas, this episode is a goldmine of practical wisdom and thought-provoking experiments in entrepreneurship and education.