My First Million

$10M Business ideas w/ The Most Interesting Guy In Tech

The hosts talk with investor and entrepreneur Shiel about housing affordability policies like a proposed 50-year mortgage, several AI-enabled business ideas for service industries, and health and longevity trends including peptides and EMS training. He shares his personal journey using surrogacy, the business opportunities and constraints in that space, and observations about prediction markets and San Francisco tech culture. They close with his contrarian view that most books are a waste of time compared to podcasts and his practice of emailing CEOs directly when brand experiences go wrong.

Nov 26, 2025

How a $200 Doorbell Became a $4B Business

The hosts interview Ring founder Jamie Sibanoff about building the smart doorbell company, navigating a near-fatal lawsuit with ADT during acquisition negotiations, and ultimately selling to Amazon for $1.15 billion. Jamie explains his problem-first invention philosophy, hiring and leadership approach, and why he sees Ring as a mission-driven company focused on making neighborhoods safer. He also describes his 'snowball' method for developing ideas, his obsession with solving the global bug problem, and his long-term project revitalizing the small town of LaBelle, Missouri.

Nov 24, 2025

We react to Bill Ackman's advice to young men

Two co-hosts discuss Bill Ackman's formal pickup line "May I meet you?" and share their own dating and pickup line stories before pivoting into examples of bold young entrepreneurs building "man-on-the-street" content businesses. They then dive into the origin story of MTV and its creative leadership, using it to explore the importance of planting a clear strategic flag, underestimating upside, and taking simple ideas very seriously. The conversation broadens into creative careers in animation, the power of curiosity and observational sensitivity in comedy, investing, and AI, and ends with a Jerry Seinfeld quote on proportion and knowing when to stop.

Nov 20, 2025

How fortnite made me a millionaire

Sean walks through roughly a decade of business attempts-from a sushi restaurant and wristband dropshipping to a biotech venture and a series of social and messaging apps-before finally finding success with a high school Fortnite esports league that was acquired by Twitch. He then explains how his approach to project selection, learning, and risk changed, leading to a streak of more straightforward wins and a portfolio doing tens of millions in revenue. The conversation shifts into money, defining "enough," the idea of a second mountain focused on creative work and meaning rather than more wealth, and ends with a light segment about Halloween, parenting, and family traditions.

Nov 19, 2025

Every Business I Tried Before Making My First Million

Sam walks through roughly ten different companies and side projects he tried before making his first million at around age 31, sharing how much money each made and what he learned from them. The conversation covers early hustles like flipping sports equipment, running a hot dog stand, selling white whiskey online, organizing an Anti-MBA book club, building a roommate-matching app, launching niche products like poison ivy treatment, and eventually creating The Hustle and this podcast. Along the way, Sam and Sean discuss developing money-making skills, scrappiness, project selection, risk reduction, and how entrepreneurship is largely about enduring uncertainty and fear over many years.

Nov 17, 2025

How Alex Hormozi Gets Other People To Build His $100M+ Empire

The host and Alex discuss how to think about talent, hiring, and leadership, including frameworks for diagnosing employee performance issues and prioritizing intelligence and small skill gaps in recruiting. They explore the evolution from operator to 'collector of people,' the importance of pattern recognition in building teams, and how to identify true partners versus employees. The conversation broadens into trade-offs between work and life, patience versus speed, the role of networks and alternative education, copywriting and persuasion, and Alex's current reflections on mortality, happiness, and redefining his priorities beyond business.

Nov 14, 2025

I Did Nothing For 2 Weeks. It Made Me Better At Everything.

Two co-hosts catch up after one has a new baby and the other returns from his grandfather's funeral, leading into honest reflections on paternity leave, men's emotional experience with newborns, and how much time off is actually useful. They explore Aristotle's concept of flourishing, the value of leisure and dedicated thinking time, and how engineered rest and movement can produce creative breakthroughs, tying into one host's project to write concise "one-hour" books and the discipline required for deep work. The conversation then shifts to Paul Graham's framework for procrastination, the transformative power of a parent or grandparent instilling belief in a child, immigrant family stories, the modern scarcity of belonging versus information abundance, and a fast-growing group travel company that builds community and reduces loneliness.

Nov 12, 2025

I Ranked the Best & WORST Businesses to Start Before 2026 | Andrew Wilkinson

The host and Andrew Wilkinson play a "tier list" game ranking different business models by their median successful outcome, lifestyle impact, upside, and difficulty, drawing heavily on Andrew's two decades of experience running agencies, buying companies, and managing capital. They discuss models such as MLMs, freelancing, agencies, SaaS, marketplaces, restaurants, content creation, real estate, hedge funds, angel investing, and buying local "sweaty" businesses, while also unpacking how Tiny was built and why its stock chart can be misleading. In the second half, they shift to psychological themes like the courage to be disliked, identity boxes, contrarian thinking, and designing a career around work you enjoy doing thousands of times rather than chasing labels or external approval.

Nov 7, 2025

The High School Dropout Who Made $2B & Bought an NBA Team

Ryan Smith describes his journey from a 1.9 GPA high school dropout to building Qualtrics from his family basement into a multi‑billion‑dollar company and later becoming an NBA team owner. He recounts being effectively forced out of school, surviving a precarious stint in Seoul as a teen English teacher, founding Qualtrics with his father during a cancer scare, and eventually turning down a $500 million acquisition offer before raising major venture capital and selling the company. He also reflects on focus, long‑term thinking, buying the Utah Jazz, and his personal frameworks for parenting and career decisions.

Nov 5, 2025

I asked Cathie Wood the question no one else will

The host interviews investor Cathie Wood about her career trajectory from early service jobs through studying under Art Laffer and breaking into Capital Group, emphasizing how she used technology and hustle to add value. Wood explains ARK's research structure, open-research philosophy, and how her team uses volatility and rebalancing to manage high-conviction positions like Tesla. She addresses performance criticisms, lessons from the COVID boom and subsequent drawdown, discusses incentive structures in finance and venture capital, and lays out her views on AI, Tesla, robo‑taxis, humanoid robots, and the future economics of transportation.

Oct 30, 2025

Masterclass: How to go from founder to CEO (without imploding)

Sam and Sean discuss how a startup's growth is constrained by the founder's psychology and development as a leader, especially after the brute-force phase ends around a few million in revenue. They contrast abdicating versus properly delegating, share concrete management frameworks (like RACI and feedback methods), and talk about building culture through real, lived values rather than slogans. In the second half, they examine how repeat founders exploit their edge talents by running the same proven playbook in similar industries, highlighting multiple examples of entrepreneurs who "speedrun" the same business model to build multiple large companies.

Oct 28, 2025

5 AI Tools I'd Use to Make $1M (w/o employees, capital, or time)

Sam and Greg walk through a series of AI-powered tools and workflows that they personally use to boost productivity, create content, and make better business and financial decisions. They demonstrate concrete use cases for deepfake-style video generation, AI-first web browsing, voice dictation, AI spreadsheets, TikTok automation, and automated job applications, while also touching on the risks and ethical concerns around scams, spam, and brain-rotting content. The conversation balances excitement about arbitrage opportunities for people going from zero to one with unease about how pervasive and manipulative AI-generated content could become.

Oct 21, 2025

How to live an asymmetric life

The host outlines five "guaranteed" ways to live a miserable life-avoiding deep friendships, remaining indecisive, neglecting goals and tracking, constantly switching projects, and trying to beat the stock market by picking individual stocks-and then explains how doing the opposite leads to a happier, more successful life. He uses philosophical ideas, psychological experiments, personal stories, and financial data to illustrate how close relationships, decisive action, clear goals, long-term focus, and simple index-fund investing compound over time. The episode concludes with a concise recap of the five positive behaviors listeners should adopt.

Oct 17, 2025

How two straight guys bought Grindr and made $2B

The hosts interview two entrepreneurs and operators who led the acquisition of Grindr from its Chinese owner under a forced divestiture and then took it public for a $2 billion valuation. They explain Grindr's origin, why U.S. regulators forced the sale, how homophobia and perceived risks created a buyer's opportunity, and the operational turnaround they executed across talent, tech, product, trust and safety, and monetization. The conversation broadens into how they approach private equity deals vs. startups, the use of leverage and risk reduction, opportunities and disruption in AI, crypto, and healthcare, and reflections on long careers in tech, investing, and choosing the right partners.

Oct 13, 2025

5 App Ideas for ChatGPT's New App Store ft. Greg Isenberg

The host and Greg Isenberg discuss OpenAI's new ChatGPT app store and the significant opportunity it creates for entrepreneurs to build apps that live inside ChatGPT. They explain how in-chat app discovery works, show examples like design and real estate tools, and brainstorm specific app concepts including an AI tax assistant, a healthcare concierge, a meme generator, an "AI Grandma" advisor, and a credit score repair utility.

Oct 10, 2025

Brainstorming $100M Ideas with the $1B+ King of Brands

The hosts interview consumer brand entrepreneur Eric Ryan about how he repeatedly reinvents everyday product categories like soap, vitamins, and bandages into large, culturally resonant brands. Ryan explains his simple but disciplined model for spotting category white space, stealing inspiration from distant industries and geographies, and balancing familiarity with novelty, then applies that thinking in a live brainstorming session for new $100M+ brand ideas. He also discusses the challenges of execution, leadership, and funding, including a recent failed retail jewelry venture and his current shift toward incubating brands and investing via a new consumer fund.

Oct 8, 2025

$50M Poker Pro Shares His Best Advice For Founders

Poker pro Daniel Negreanu joins the hosts to explore the parallels between high-stakes poker and entrepreneurship, including reading people, managing risk, and handling emotional swings. He describes how he developed his observational skills, his early ups and downs in Las Vegas, and his philosophy on bankroll management and when to take big risks. The conversation broadens into emotional intelligence, personal responsibility, learning from rock bottom moments, and the importance of continually updating one's mental "software" to stay world-class in any field.

Oct 6, 2025

The App That'll Be Bigger Than TikTok

The hosts discuss OpenAI's new Sora app for AI-generated video, exploring its onboarding flow, social mechanics, and why it may be more powerful than TikTok as a multiplayer AI experience. They broaden the conversation to AI as a super app (including ChatGPT's Pulse), concerns about OpenAI's growing power, and how AI will reshape content creation, education, therapy, and addiction support. The episode also covers the rise of micro sports betting and prediction markets, new businesses tackling gambling addiction with AI, and the extreme personal data logging practices of Shopify CEO Tobi Lütke alongside their own approaches to life-logging and memory capture with tools like Meta smart glasses.

Oct 3, 2025

The Hospitality Principles That Build Billion-Dollar Startups

The host interviews restaurateur and author Will Gudera about the philosophy and practice of "unreasonable hospitality" that helped his restaurant Eleven Madison become a top destination. They discuss how small, highly personal gestures can matter more than perfect execution, how to build a culture of rigorous feedback and care, and how to operationalize hospitality through roles like the "Dreamweaver" and systems such as one-size-fits-all, one-size-fits-some, and one-size-fits-one experiences. The conversation also explores applications in other industries, the economics of restaurants, and the broader pursuit of excellence in life and business.

Sep 30, 2025

He turned a broke team into a billion dollars

The hosts profile Jesse Cole and the Savannah Bananas, tracing how he transformed a struggling summer-league baseball operation into a massively in-demand entertainment phenomenon. They describe his decade of experiments with the Gastonia Grizzlies, the all‑in risk he and his wife took to launch the Savannah Bananas, and the fan‑first innovations that led to Banana Ball and a huge touring live show business. Along the way they draw parallels to MrBeast, Steve Jobs, Will Guidara, Dan Porter, Monster Jam, and Feld Entertainment to explore strategy, hospitality, showmanship, and building AI‑proof live experiences.

Sep 26, 2025

How to Get Rich (without luck, talent or a trust fund)

The host lays out four "rules of money" that he used to go from being broke in his twenties to making his first million by 30 and later building a net worth of $30 million. He explains how to pick and master one of four core money-making skills, convert that skill into equity via code, content, or capital instead of renting out time, adopt a long-term perspective that is impatient with action but patient with results, and deliberately move closer to ambitious peers and industry hubs to accelerate progress. Throughout, he illustrates the rules with concrete examples from his own life and from figures like Mr. Biso, Warren Buffett, Steve Jobs, Elon Musk, Alex Ramosi, and Steve Martin.

Sep 24, 2025

The Side Hustle King: 11 Easy Businesses Anyone Can Start

The hosts bring back their "side hustle king" guest Chris to share a series of concrete, small-business and side-hustle ideas ranging from seasonal porch pumpkin decorating and backyard sport courts to in-ground trampolines, male "dollhouse" building kits, liquidation arbitrage, and mobile fuel delivery. They discuss how these seemingly simple service and niche product ideas generate substantial revenue, how Chris validates demand with short-form content and paid ads, and how he structures operations with subcontractors and partners. Later, Chris describes his RV park investments, his interest in AI automation services for small businesses, and his plans for an AI-enabled QuickBooks competitor.

Sep 22, 2025

How To Turn $100K into $4,000,000 with Distressed Investing

The hosts interview a distressed investor named Tom who specializes in buying bankruptcy claims, especially in crypto-related cases like Mt. Gox and FTX, and walk through how his niche works. He explains the "stake and sizzle" approach to finding situations with both downside protection and significant upside optionality, details the hustling and legal knowledge required to trade claims, and shares stories from early crypto bankruptcies and his own investing background. Later, he candidly discusses a controversial Delaware receivership case that resulted in fines and a settlement, and closes with core investing philosophies and a reading list for learning more about distressed and value investing.

Sep 19, 2025