My First Million

Two successful entrepreneurs share their biggest early mistakes, career advice, and wish-list business ideas in a mailbag episode

with Jesse Itzler

Jesse Itzler shares his three-step system for planning an intentional year: getting light, closing out the previous year, and choosing one year-defining challenge (misogi).

with Alex Hormozi

Alex Hormozi breaks down his frameworks for hiring A+ talent, scaling businesses through people collection, and defining reality with precise language.

with Ryan Smith

A behind-the-scenes look at billionaire NBA owner Ryan Smith's approach to business, basketball, and building across multiple domains.

with Greg

A practical walkthrough of 6 AI tools that can automate business workflows, content creation, and productivity tasks for solo entrepreneurs.

with Eric Ryan

Eric Ryan reveals his systematic approach to creating billion-dollar brands by finding cultural shifts in boring categories and applying single, powerful changes.

with Daniel Negreanu

World-class poker pro Daniel Negreanu shares how mastering emotional intelligence, reading people, and handling adversity translates from poker to business success.

with Will Guerrero

How unreasonable hospitality principles from the world's best restaurant can transform any business through systematic attention to forgotten touchpoints.

How Jesse Cole turned a broke minor league baseball team into a billion-dollar entertainment empire by making baseball fun through relentless fan-first innovation.

with Chris

A serial entrepreneur shares 10+ profitable business ideas from porch pumpkins to RV parks, revealing how to spot opportunities and scale quickly.

with Chris Voss

Former FBI hostage negotiator Chris Voss reveals how tactical empathy, trust-building, and making others feel heard creates better business deals than leverage or compromise.

with Dharmesh Shah

HubSpot's billionaire founder explains how SEO is dying and reveals AEO (Answer Engine Optimization) as the new marketing frontier while sharing his philosophy of treating business like a video game.

with Dan Porter

Dan Porter explains how he built viral brands by listening to culture, moving fast, and turning weaknesses into positioning advantages.

with Hayes Barnard

A day-in-the-life experience with billionaire Hayes Barnard exploring his anti-routine philosophy through morning breathwork, cold water plunges, and the practice of doing something new every day.

with Tim Ferriss

Tim Ferriss discusses his evolution from productivity optimization to post-economic living, current health research obsessions, and predicted shift toward analog human experiences.

with Howie (Airtable Founder)

Airtable founder Howie shares seven AI business ideas he'd pursue if starting over, from avatar commerce to AI news aggregation.

with Chris

Chris makes $8,000 daily from multiple side hustles by finding simple, overlooked local businesses and using math-based approaches rather than traditional focus strategies.

with Jason Lemkin

SaaS veteran Jason Lemkin shares insights from building an AI clone of himself that had 50,000 conversations, revealing how AI is fundamentally disrupting software businesses and creating new opportunities for relentless founders.

with Logan Ury

Dating is a systematic skill like business - most people fail because they don't try on the things that matter, not because the game is impossible.

with Ankur Nagpal

A tech founder who sold for $250M shares tax optimization strategies and business ideas across health, food, travel, and sports

with Blake Scholl

How a computer science dropout taught himself aerospace engineering and raised $5 billion in preorders for supersonic jets by applying first principles thinking to obvious problems hiding in plain sight.

Car dealerships can make athletes billionaires, AI marketplaces need better imagination, and someone raised $1.5M for live sperm racing competitions.

with David Senra

Anti-business billionaires like Jobs, Dyson, and Chouinard succeed through extreme disagreeableness, product obsession, total control retention, and treating their companies as family heirlooms rather than assets to sell.

A parable about happiness mastery through controlling focus, state, and story

with Alex Lieberman, Austin Rief

Three newsletter founders share revenue numbers, growth tactics, and lessons from building and selling $100M+ newsletter businesses

with Zach Yagari

18-year-old high schooler Zach built a $24M ARR AI calorie-tracking app by combining coding skills with TikTok marketing mastery.

with Brent Beshore

Private equity operator shares contrarian investment philosophy using no debt, 30-year holds, and deep personality assessment to build $350M+ revenue portfolio.

with Nick Bilton

Investigative journalist Nick Bilton reveals Silicon Valley's hidden stories through obsessive research and explains why the official narratives are usually fabricated.

with Sean

Inside look at how billionaires think, work, and live differently through a 48-hour immersive experience

A deep dive into the $450M Muscle Milk success story, distressed asset investing, and decision-making frameworks for entrepreneurs.

with Sheel Mohnot

Serial entrepreneur Sheel Mohnot shares five $10M+ business ideas while discussing his adventurous approach to life and business building

From Christmas tree kingpins making millions in NYC to health startups getting massive traction, exploring seasonal businesses and the shifting culture around preventative health

Revenge, identity wounds, and childhood trauma are the most underrated predictors of entrepreneurial success

Three deceptively simple blue-collar businesses with brilliant marketing that you'll wish you'd thought of first.

with Ryan Peterson

Flexport CEO Ryan Peterson shares contrarian wisdom on wealth creation, the power of competing with dumb competition, and how to build defensible businesses from public data arbitrages.

with Tommy Potter (University of Michigan), Austin (UIUC), Jonah (Meet Your Class), Shar (Metapo), Nathan (Milu), Austin Majors (Brothers Nuts), Tour Team (Michigan), Adva (Pathet)

College entrepreneurs from Michigan and UIUC pitch their startups in a Shark Tank format, covering everything from university enrollment software to AI dubbing to sprouted nuts.

Seven unconventional business ideas focusing on high-touch services, from luxury matchmaking to door-to-door tech support, emphasizing sales skills over technical complexity.

with Nick Gray

A systematic approach to hosting $100 parties that builds social status by creating meaningful connections through name tags, structured introductions, and value-additive conversations.

Deep dive into the HBO documentary claiming to unmask Bitcoin creator Satoshi Nakamoto as Peter Todd, plus Bitcoin's mainstream adoption journey.

The wild story of tech billionaire Mike Lynch who stayed at Sam's dad's Airbnb while on house arrest, plus lessons on authentic content creation and business strategy.

From viral pickup lines to $300K/month park interviews, exploring how unconventional hustlers build empires by taking simple ideas seriously.

with Anne Mahlum

Anne Mahlum built a $1M nonprofit helping homeless individuals through running, then bootstrapped SolidCore Pilates from $175k savings to a $300M+ exit in 9 years.

Two podcast hosts dissect their recent fight to extract relationship wisdom, discovering that conflict resolution is a learnable skill.

A systematic framework for creating high-value offers by maximizing dream outcome and perceived likelihood while minimizing time delay and effort/sacrifice.

Everyone needs someone who believes in them more than they believe in themselves - it's not about advice or money, it's about belief that fuels you until your evidence catches up.

An built Solidcore from a $175k investment into a $250M sale by creating a premium Pilates studio with exceptional unit economics and word-of-mouth growth.

A mom-focused Q&A community could capture massive value by serving the opposite need to AI - trusted human wisdom from a like-minded demographic.

An exploration of why jingles dominated 90s marketing, how prediction betting platforms work, and the ethics of whale-based monetization in games and gambling.

with Kevin Van Trump

Kevin Van Trump built a $20M+ agricultural newsletter business by combining trading expertise with farming knowledge, serving a highly specific niche at premium pricing.

with Craig Fuller

Craig Fuller built a $60M media empire by acquiring undervalued magazines and turning them into commerce platforms for enthusiast audiences.

Video is becoming the native language of the internet, with cinematic-style content creators disrupting traditional media and marketing through high-production, scripted content that outperforms raw, authentic approaches.

with Kevin Espiritu

Kevin Espiritu built Epic Gardening from a $450/month hobby blog to a $45M/year media-to-commerce empire through strategic acquisitions and audience monetization.

with Gary Vaynerchuk

Gary Vaynerchuk shares his frameworks for identifying winning investments, managing risk, and day-trading attention across platforms.

with Shaan Puri, Sam Parr

Shaan and Sam dissect the $52M Shepherd acquisition while revealing the audience co-founder playbook and the psychological traps that keep entrepreneurs stuck at familiar income levels.

with Scott Galloway

Scott Galloway breaks down his brutal but practical wealth-building philosophy: follow talent not passion, work your ass off early, diversify everything, and use America's unique tolerance for failure.

A deep dive into Hunt Brothers Pizza's $540M gas station empire, GeoGuesser's pandemic boom to $21M, and viral content strategies.

with Jeremy Giffon

Jeremy Giffon shares specific business opportunities from audience co-founder models to regulatory compliance plays, plus contrarian takes on holding companies and wealth psychology.

A deep dive into the mindsets, habits, and philosophies of ultra-successful entrepreneurs in Austin, revealing patterns of focus, curiosity, and strategic thinking.

with Steph Smith

Steph Smith reveals data-driven trends and business opportunities in hearing loss, drone delivery, psychedelics, labor shortages, and biomimicry innovation.

Vertical SaaS exits, content marketing strategies, and platform inflection opportunities with examples of Follow-up Boss ($500M), Brian Johnson ($20M day one), and OpenAI App Store timing.

with Ankur Nagpal

A $250M exit founder breaks down legal tax strategies that business owners use to keep more of their money, from QSBS stacking to solo 401ks.

Two entrepreneurs brainstorm ridiculous business ideas while drinking sparkling water, ranging from habit bootcamps to AI influencers to divorce resorts.

with Sam Parr

Sean shares insights from Camp MFM, revealing MrBeast's billion-dollar mindset and unconventional business practices that set outliers apart from typical entrepreneurs.

A SaaS founder starts a neighborhood trash company after getting frustrated with poor service, while the hosts explore alternatives to New Year's resolutions and discuss community monetization strategies.

Nine counterintuitive principles for building an authentic audience from zero, focusing on quality over quantity and systematic improvement.

with Preston Holland

Craig Fuller built a $50M/year magazine roll-up that uses content to sell high-value products to niche audiences.

Year-end awards covering crazy people met, investment wins/losses, unsexy businesses that crush it, content recommendations, and predictions for the future.

Two podcast hosts dissect their year of 100M+ views and share hard-won lessons about consistency, negotiation, tax planning, and the psychology of never having enough.

with Ali Abdaal

Ali Abdaal shares how he scaled from $227 to millions in revenue through strategic course creation, productivity frameworks, and treating content creation like a real business.

A deep dive into how Plunge went from zero to $100M in cold therapy sales, plus opportunities in supplement testing and short-form content platforms.

with Nick Mowbray

How two naive brothers went from selling hot air balloons door-to-door to building a $2B+ manufacturing empire by automating everything and never losing money again.

A play-by-play analysis of Sam Altman's shocking OpenAI firing and Microsoft's masterful acquisition of the entire team within 48 hours.

with Patrick Campbell

Patrick Campbell shares his systematic approach to finding business ideas through trend analysis, pricing optimization, and product remixing frameworks.

with Moiz Ali

Native deodorant founder Moiz Ali shares how he manages his $100M+ portfolio in a Google Sheet and reveals business ideas from real estate stock markets to Shopify app arbitrage.

with Craig Clemens

Master class on the seven psychological hijacks used to sell over $1 billion in products, from creating daily habits to hijacking human rebellion instincts.

A rapid-fire presentation of 10 specific AI business opportunities ranging from practical applications to transformative agent-based productivity systems.

Shaan dissects Linda Yaccarino's disastrous Code Conference interview, exposing poor preparation, defensive communication, and corporate BS in real-time.

with Kevin Ryan

Billionaire serial entrepreneur Kevin Ryan reveals his systematic approach to building $20B+ companies through deep industry research, 10-year trend betting, and the studio model.

with Mark Manson

Mark Manson shares his evolution from pickup artist to bestselling author to YouTube creator, revealing the psychology behind viral content and male role models.

A deep dive into copywriting scams, newsletter growth tactics, dating app innovations, and predictions about what will seem barbaric in the future

Observations from a week in LA reveal networking strategies, wealth psychology, and business insights through little big details.

Sam Parr shares his 6-step methodology for finding million-dollar business ideas through systematic research of demand, audience, leaders, shortcomings, business models, and unsolved problems.

Sam reveals his conservative $10M+ investment portfolio split between index funds, treasuries, and private investments while sharing lessons on emotional investing mistakes and wealth preservation strategies.

Two podcast hosts discuss the Musk-Zuckerberg cage match, share investment lessons from Beehive, and explore the concept of building a 'Total Man' movement around masculine identity.

A comprehensive playbook for selling your startup based on real M&A experience, covering psychology, buyer mapping, positioning, and negotiation tactics.

with Rob Dyrdek

Rob Dyrdek built $350M in wealth in 5 years through venture creation, real estate, and entertainment deals while developing a systematic approach to human optimization.

Three unconventional businesses that succeeded through niche focus, authentic execution, and contrarian market positioning.

with Andrew Wilkinson

Live Q&A revealing the real origin story of MFM, investment lessons, community building psychology, and Andrew's wealth-to-purpose journey

Sean and Sam explore profitable small businesses from play spaces to sample sales while dissecting Vice Media's spectacular rise and fall through founder Shane Smith's wild showmanship.

A masterclass in tax optimization, business analysis, and viral mechanics from wealthy people's film financing schemes to Harvard's $50B tax-free empire.

Sean Puri shares his battle-tested pitch deck template that he's used to raise millions, walking through each slide with a real insomnia app example.

with Ben Levy

How a quilting company bought an entire town and turned it into a themed tourist destination, plus lessons on networking, authentic communication, and spotting business opportunities.

with Anthony Pompliano

Pomp breaks down his 8-figure media empire, why he ditched advertising to own products, and his philosophy on finding young contrarian talent.

A news reaction episode covering Elon's public firing of a disabled employee, money-happiness research, and various tech/culture topics.

with Ken

A former Wall Street trader turned endurance athlete shares how he overcame addiction and reinvented himself through extreme physical and mental discipline.

Hosts analyze current events including Jake Paul's boxing loss, Andrew Tate's detention, COVID lab leak theory validation, and critique tech buzzwords while sharing personal philosophies on wealth, legacy, and platform adoption.

Deep dive into Bernard Arnault's luxury empire strategy, modern internet business relationships, and frameworks for evaluating high performers.

COVID created massive opportunities for those who pivoted quickly, while most people either missed the window or got stuck in analysis paralysis.

Tech news reactions covering Meta's stock surge, NFT success stories, weird product launches, and scammer exposés.

Three fundamental shifts for building wealth: work smart not hard, get close to money, and swing hard at fat pitches.