Infinite Loops Episode 286: Jay Yang — The Power of Permissionless Action

Host: Jim O'Shaughnessy
Guest: Jay Yang
Date: October 16, 2025
Theme: Harnessing Agency and the Power of Permissionless Action for Personal and Professional Growth

Overview

In this invigorating episode, Jim O'Shaughnessy sits down with Jay Yang, a writer, entrepreneur, and advocate for “permissionless action.” The conversation centers on what it really means to take initiative without waiting for external validation, how to reprogram your mental operating system for agency and persistence, and practical tactics for breaking through self-imposed and societal barriers. They also dive into the implications of AI on creativity and opportunity, and touch on the importance of curiosity, clarity, and working in public.

Key Discussion Points & Insights

The Philosophy of Permissionless Action

• Jay’s Backstory:

  • At 16, Jay cold-emailed Tyler Denk (Beehiiv CEO) with a specific plan, which secured him an internship ([01:53]).
  • At 17, he sent a 19-page app audit to Noah Kagan, ultimately leading campaigns that helped get "Million Dollar Weekend" on the NYT bestseller list.
  • His book "You Can Just Do the Power of Permissionless Actions" was inspired by stacking small, bold moves ([03:39]).

• Main Idea:

  • Success isn’t handed to you; you must create your own opportunities by doing the work up front.
  • “Preparation beats bravado… there is no speed limit. Ask yourself, ‘what’s stopping me from going faster?’” – Jay Yang ([05:07]).

• Host’s Perspective:

  • Most people are conditioned by the “reigning ideas” of their era, following conventional paths. Jim shares his own entrepreneurial start as bucking this tradition ([06:07]).

Overcoming Limiting Beliefs and Societal Conditioning

• On Agency and Internal Programming:

  • “When you say, it’s easy for you to say, you’re placing your own agency onto the other person... Who wrote the mental software that's running through your mind?” – Jay ([11:08]).
  • Emphasizes rewriting negative scripts and taking responsibility for self-talk:
    • “The angry man lives in an angry world. The happy man lives in a happy world.” – Jim ([12:29])

• Concrete Strategies for Building Agency:

  • Start small: “Confidence doesn’t come from shouting affirmations in the mirror, but giving yourself an undeniable stack of proof that you are who you say you are.” – Jay quoting Alex Hormozi ([13:52])
  • Accumulate “small wins” to rewire beliefs.

• Inputs vs Outputs:

  • High-agency people focus on the actual results (outputs), while low-agency people focus on effort (inputs):
    • “The only true test of intelligence is whether you get what you want out of life.” – Jay referencing Naval ([17:43]).

Failure as Feedback and The Pre/Post-Fall Mentality

• Reframing Failure:

  • “Failure isn’t the opposite of success. It’s the road to success... The only true failure is quitting because you got discouraged.” – Jay ([20:16])
  • Failure becomes feedback and writing fodder.

• Pre-Fall vs Post-Fall:

  • “Pre-fall is when you’re full of piss and vinegar... Post-fall is after you’ve gotten hammered by reality and learned humility.” – Jim ([21:05])
  • Jay: “How you respond is what truly makes who you become. Character isn't tested when things are easy, it’s tested when things are hard.” ([23:27])

Obsession, Persistence, and Curiosity

• Throughlines Among High-Achievers:
  • “Obsession isn’t what you want to do. Obsession is what you can’t not do.” – Jay ([28:43])
  • Cites Kobe Bryant, Sam Walton, Dyson, Edison – all were deeply obsessed and persistent.
  • “Curiosity is like magic.” – Jim ([31:10])
  • Working with intensely curious people from different domains yields serendipitous collaboration ([33:29]).

Permissionless Action in the Age of AI

• AI as a Tool, Not a Threat:

  • “I use AI... probably more than I talk to humans on most workdays.” – Jay ([38:20])
  • AI enables exponential leverage; it's the humans who embrace tools that win.
  • Analogy: Using AI is like using a calculator—still your thinking, just more leverage ([38:33], [43:45]).

• Jim’s Frustration at AI Skeptics:

  • “Would you have preferred Michelangelo didn't have paint and brushes?... Every tool has its positive and negatives.” ([39:53])

• Cultural Resistance:

  • “Humans conflate things that are hard for things that are good... Busy isn’t better.” – Jay ([43:45])
  • Exponential > linear thinking is key.

Breakthrough Tactics: The TAG Method for Outreach

• Jay’s Repeatable Playbook: ([57:53]–[60:55])

  • Target: Choose someone one or two steps ahead, not the unreachable guru.
  • Audit: Deep research on their work, problems, and goals.
  • Gift: Deliver something valuable for free, showing initiative and lowering friction for a yes.
  • “Here, I made this for you. If you like it, let’s work together. If not, no harm, no foul.”

• Host’s Application:

  • OSV now hires everyone as a consultant first, to see the “movie” of their work style over time.

Noise vs Signal in the Era of AI Overload

• Finding the Right Mentors:

  • “Not: ‘Did this person achieve what I want to achieve?’ but: ‘Did they help others like me do it, many times?’” – Jay ([51:37])
  • The best teachers are often not the most visible or charismatic, but the “operators who have been quietly compounding experience in the dark.” ([54:28])

• “Find Tenzig Norgay, not just Edmund Hillary.” – Jim ([55:50])

• Work in Public Ethos:

  • Share your journey as a guide, not a guru; it builds serendipity and unexpected opportunities ([56:18], [75:50]).

Clarity, Motivation, and North Stars

• Clarity Unlocks Action:

  • “People don’t lack motivation, they lack clarity... It’s hard to get what you want if you don’t know what you want.” ([67:34])

• Jay’s North Star (and Anti-Goals):

  • “A fit body, a calm mind, a house full of love, meaningful work, and enough wealth not to worry about it.” ([69:57])
  • Also clear about what he doesn’t want: stress, isolation, meaningless busy work.

• Quoting Viktor Frankl:

  • “You can deal with almost any ‘what’ if you know why.” ([72:21])

Real-Life Upsides of Working in Public

• Jay’s latest opportunity at Acquisite came directly from his online writing ([75:50]).
• Countless friendships, collaborations, and serendipitous events.

Notable Quotes

• “Preparation beats bravado… there is no speed limit. Ask yourself, ‘what’s stopping me from going faster?’” – Jay ([05:07])
• “Who wrote the mental software that's running through your mind?” – Jay ([11:08])
• “Confidence doesn’t come from shouting affirmations in the mirror, but from giving yourself an undeniable stack of proof that you are who you say you are.” – Jay quoting Alex Hormozi ([13:52])
• “Failure isn’t the opposite of success. It’s the road to success.” – Jay ([20:16])
• “Obsession isn’t what you want to do. Obsession is what you can’t not do.” – Jay ([28:43])
• “I use AI... probably more than I talk to humans on most workdays.” – Jay ([38:20])
• “High agency people think in exponentials.” – Jay ([48:09])
• “Clarity trumps motivation.” – Jim ([67:34])
• “People don’t lack motivation, they lack clarity.” – Jay ([67:34])
• “You can just do things.” – Jay ([82:00])
• “Define your North Star.” – Jay ([82:00])

Memorable Moments & Timestamps

• [05:07] — Jay: “There is no speed limit... Ask yourself, ‘what’s stopping me from going faster?’”
• [13:52] — Jay on confidence and small wins (“undeniable stack of proof”)
• [20:16] — Jay: “Failure isn’t the opposite of success. It’s the road to success.”
• [28:43] — Jay on obsession: “Obsession is what you can’t not do.”
• [38:20] — Jay: “I use AI... probably more than I talk to humans on most workdays.”
• [43:45] — Jay: “Just because you’re working harder doesn’t mean you’re morally superior.”
• [57:53] — Jay describes the TAG method for permissionless outreach.
• [67:34] — Jay: “People don’t lack motivation, they lack clarity.”
• [69:57] — Jay’s five-part North Star.
• [82:00] — Jay’s “Emperor of the World” inceptions: “You can just do things” and “Define your North Star.”
• [75:50] — Unexpected upsides of working in public: landing his current role at Acquisite.
• [78:40] — “Descend into hell to create heaven.” – a teaser for Jay’s second book.

Actionable Takeaways

• Adopt Permissionless Action: Don’t wait for permission or a tap on the shoulder—do the work up front, show empathy, and make it as easy as possible for others to say yes.
• Reprogram Your Mental OS: Question your defaults. Are your thoughts and beliefs your own, or did someone else write them?
• Start Small, Then Stack Wins: Build confidence and agency by accumulating small, undeniable victories.
• Embrace and Leverage Tools (AI): Use exponential technologies early and often; being purist about the medium is just self-limiting.
• Work in Public: Sharing your process or journey leads to serendipitous connections and unexpected opportunities.
• Seek Out Real Guides, Not Gurus: The best help often comes from experienced operators and those a step or two ahead, not the loudest voices.
• Clarity Over Motivation: Knowing your North Star (“why”) unlocks sustainable action; anti-goals also bring focus.
• Persistence + Obsession: Consistent effort, married to genuine obsession, is the root of high agency and extraordinary achievement.

Where to Find Jay Yang

• Twitter/All Socials: @JYangInspires
• Newsletter: jminspires.beehiv.com

Closing Wisdom (Jay’s Emperor-for-a-Day Edict):

1. “You can just do things.”
2. “Define your North Star.”
   ([82:00])

Recommended for anyone wanting to:

• Rewire their approach to opportunity,
• Cut through societal or self-imposed barriers,
• Harness AI as leverage,
• Upgrade their “HumanOS”—and define, then pursue, a life of agency and fulfillment.