Earn Your Leisure

Tommy Duncan grew up in the healthcare industry, with his partners owning the only black-owned hospital in Detroit. After they fell on hard times and lost the business, he became an entrepreneur in the health space. He moved up the ladder quickly in the field and sold his first company in his 20s for $1.5 million. Years later, he sold his second healthcare company for $120 million. Most recently, he made news by starting a low-cost-subscription healthcare company called Jetdoc. Rick Ross is a main investor in the company, investing over one million dollars into the venture. He has also been a public advocate for the revolutionary business model. On episode 155, Tommy broke down the trillion dollar healthcare industry, and he explained the process of selling his company for over $100 million. He also detailed the angles of government contracting that can make entrepreneurs rich, and he outlined a plan to decrease health expenses by helping the homeless. #healthcare #jetdoc #rickross #tommyduncan EYL University

In this video, we discuss the benefits of leasing a car. We also discuss buying a new car vs buying a used car and how to get the best deal when purchasing a car. #cars #leasing #usedcar Full Interview:    • LEASING VS BUYING A CAR  See omnystudio.com/listener for privacy information.

In this video, we discuss the dangers of the middle class mindset and how it can prevent you from achieving success. If you want to achieve great things in life, you need to break out of the middle class mindset and start thinking like an entrepreneur. Watch this video to learn more!See omnystudio.com/listener for privacy information.

In this clip Floyd Mayweather talks about Gervonta "Tank" Davis' desire to leave Mayweather Promotions. #gervontadavis #floydmayweather #boxing Link to Full Episode:    • Floyd Mayweather on His Plans to Buy an NB...   EYL University: https://www.eyluniversity.com Monthly Investment Deal: https://www.earnyourleisure.com/pages...See omnystudio.com/listener for privacy information.

In this insightful Market Mondays clip, Rashad Bilal, Ian Dunlap, and Troy Millings break down Netflix’s strategy and the latest shake-ups in the streaming and media industries. The hosts debate whether Netflix can reclaim $100+ per share and if it’s still a top buy for long-term investors—even as seismic changes hit Paramount and major players like Larry Ellison double down on media investments. The conversation kicks off with Rashad Bilal sharing why Netflix’s push into live events, like big fight nights and sports, is building a new moat around its business—transforming them into this generation’s version of cable. Ian Dunlap reinforces the bullish outlook, reminding investors that while big year-over-year gains might slow, Netflix is still one of the best-run companies in media. The hosts urge viewers to get comfortable with longer holding periods, noting that industry giants are playing 20- to 30-year games while everyday investors sometimes focus way too much on 3- to

Are you ready for 2026? In this Market Mondays clip, Rashad Bilal, Ian Dunlap, and Troy Millings dive deep into the biggest mistakes investors might make in the upcoming year—and how to avoid them. Whether you’re just starting your investment journey or looking to refine your strategy, this discussion delivers blunt, practical advice to help you prepare for seismic changes ahead. Ian Dunlap emphasizes the importance of accumulating shares, knowing your “freedom number,” and tuning out distracting online noise. He highlights how top entrepreneurs—like Magic Johnson and Gary Vee—are doubling down because the financial landscape is about to shift. Ian’s no-nonsense approach: find a way to acquire at least 2,000–3,000 shares and stay focused! Troy Millings warns against “gossip trading”—making investment decisions based on hearsay or hype, rather than solid research. He stresses the danger of treating your brokerage account like a gambling app, and

In this clip Storm Leroy talks about the keys to build generational wealth through opening up a trust. #trust #generationalwealth #lifeinsuranceSee omnystudio.com/listener for privacy information.

In this clip from EYL, Rashad Bilal, Troy Millings, and Dave Salvant have a candid conversation about the realities of launching, scaling, and valuing SQUIRE—the revolutionary platform transforming the barbershop industry. Dave Salvant breaks down the challenges and successes of marketing SQUIRE to both Black and non-Black barbershops, revealing how preconceived notions and internal biases initially influenced their outreach strategies. He shares insightful lessons about how he and his team discovered their approach resonated widely, and how direct, authentic engagement can break stereotypes. The discussion delves deep into the nuts and bolts of business growth. Dave details the journey from personally pitching barbershops to building a repeatable, scalable business model and an executive team capable of taking SQUIRE to new heights. He emphasizes the importance of doing the unscalable things at first—rolling up their sleeves and knocking on doors—before building the processes for true scale

In today’s Earn Your Leisure episode, Mark Saint‑Julien (chatgpt://generic-entity?number=0) breaks down the real truth about investing in real estate across Africa. He explains how he first entered the market, why cash is still king in many African countries due to limited trust in banks, and how investors can avoid common scams. The conversation dives into the three essential land contracts everyone must understand, why cities like Dakar are seeing rising prices with steady demand, and how access to reliable information remains one of the biggest barriers for investors.   Mark also highlights where everyday investors can find real opportunities as Africa’s middle class rapidly expands. From the biggest mistakes people make when investing on the continent to realistic cost-of-living insights—like living comfortably in Ivory Coast on $1,500 a month—this episode puts numbers and context behind the hype. The discussion closes with a look at why six-figure earners have outsized purcha

Get ready for an honest, no-nonsense look at the future of the financial markets! In this insightful Market Mondays clip, Rashad Bilal, Ian Dunlap, and Troy Millings break down what’s on the horizon for 2026 and beyond—and how you can put yourself in the best position to benefit. Ian Dunlap sets the tone by predicting a tumultuous year ahead but with a positive ending in 2026, urging viewers to focus on *asset accumulation*. Whether you believe in Bitcoin, Microstrategy, index funds, or even dreaming about SpaceX, now is the time to become an “asset hoarder.” The key message? Deploy your capital into assets with conviction rather than waiting for the perfect moment! Troy Millings adds optimism, emphasizing major “catalyst events” like continued spending from tech giants such as Amazon, Meta, Microsoft, and Google. According to Troy, deregulation in AI and infrastructure spending will be a key theme, helping both technology and financial sectors. He predicts further gains fo

In this insightful clip from "Black Out with Ian & Rashad," hosts Rashad Bilal and Ian Dunlap dive deep into the important—yet often misunderstood—topic of year-end tipping. Responding to a listener question, they break down who should be on your tip list during the holiday season, how much you should give, and why showing appreciation to those who make your life easier is essential. Rashad shares common scenarios, highlighting everyone from sanitation workers, teachers, and valets, to barbers, school bus drivers, and even your building’s concierge. Ian provides real-life examples from his own life, pointing out the value of tipping your cleaning crew, building staff, and even the mailman. The duo discusses the nuances of tipping based on the service received, relationships built over the year, and the importance of recognizing excellent customer service. They also tackle those awkward gray areas: Is it necessary to tip your child’s high school teacher, or does it stop at preschool

In this insightful clip from Market Mondays, hosts Rashad Bilal and Ian Dunlap dive into one of the most important lessons for traders and investors: the dangers of chasing fast wins and why true wealth is built with discipline and patience. Ian shares his futures trading tip of the week, reflecting on lessons from the recent trading tournament and highlighting the importance of letting trades “breathe” and strategically planning entries on volatile market days like when Powell speaks or economic reports drop. Rashad and Ian also explore the blurred lines between trading and sports wagering, referencing Robinhood’s innovative approach and how more traders are entering the world of in-game contract trading. The conversation turns critical as they unpack mistakes young investors often make—especially when trying to score fast gains in meme stocks or speculative sectors like NFTs. Ian warns that while hitting a quick win may seem rewarding, it often breeds poor discipline and risky habits

In this Market Mondays clip, Rashad Bilal, Troy Millings, and Ian Dunlap break down the hottest crypto-related stocks and ETFs in today's market. The team dives deep into the strengths and weaknesses of Coinbase, IBIT (iShares Bitcoin Trust), and MicroStrategy—three major ways investors can get exposure to cryptocurrency through the stock market. Rashad starts the conversation by identifying each asset: Coinbase is the go-to platform for buying cryptocurrency, IBIT follows the price of Bitcoin as an ETF (backed by industry giant BlackRock), and MicroStrategy is a company that’s become synonymous with Bitcoin holdings—practically turning into a Bitcoin treasury. Ian highlights the importance of analyzing risk versus reward. He points out that while MicroStrategy once claimed the top spot due to its bold Bitcoin accumulation, current threats and volatility push it to the bottom of his ranking. Coinbase, with its strong leadership and lower perceived risk, gets his vote for number one. IBIT sit

This week on Earn Your Leisure, we sit down with Sonny Adams and Dave Salvant, the co-founders of Squire, to break down how they built a barbershop tech platform into a $750 million company. They share how they met, landed their first customers, and built their first product without deep technical skills — including why they gave Squire away for three years before ever charging. The conversation dives into the realities of fundraising, from relying on angel investors to survive, taking 60 meetings to secure one VC, and how an $8 million Series A helped unlock massive growth. Sonny and Dave also explain the role Y Combinator played, the strings attached to outside capital, ownership dilution, and what investors truly expect when they invest. We also explore how Squire scaled to 32,000 barbers and 10 million customers, what their $750M valuation actually means, and the challenges of being two Black founders raising capital. Plus, we discuss Squire’s marketing strategy, deploying $100 million in one

In this Market Mondays clip, Ian Dunlap and Troy Millings dive into Oracle’s latest stock pullback and tackle the burning question: Is now the right time to buy Oracle shares? The conversation breaks down everything investors need to know—including the timing of Oracle’s cloud profitability, the challenges of CAPEX spending, and the shift in market sentiment. Ian Dunlap emphasizes patience, advising investors to wait until Oracle dips closer to $160 before considering an entry point. He highlights how the overall market environment has shifted, urging viewers not to expect every tech company to produce Nvidia-like returns. Troy Millings adds depth by dissecting the nature of cloud profitability, noting that significant returns are often “future dated”—it took Amazon and Google years to generate meaningful profits in their cloud divisions. He draws comparisons to Microsoft’s Azure, explaining that Oracle is following a proven path, even as it faces margin pressure and

In this clip legendary musician and entrepreneur Ryan Leslie breaks down how he made $2 million off an independent album that only sold 17,000 copies. #RyanLeslie #independentartist #musicbusiness Full Episode:    • Ryan Leslie discuses tech, text management...   EYL University: https://www.eyluniversity.com EYL University 40% off Annual Tuition Code: EARNERSSee omnystudio.com/listener for privacy information.

In this insightful clip, Vlad Tenev, co-founder and CEO of Robinhood, sits down with Rashad Bilal to discuss the rapidly evolving world of crypto, the transformative potential of bitcoin, and how Robinhood is pioneering innovative prediction markets. Vlad explores the next decade of crypto, emphasizing its role in making high-quality U.S. financial tools accessible globally. He highlights how stablecoins, especially US dollar-based ones, have brought financial stability to people in countries with unreliable banking systems and unstable currencies. According to Vlad, the future lies in extending this access—with crypto and tokenization enabling users anywhere to invest in U.S. stocks and other global assets, leveling the financial playing field. When Rashad asks about bitcoin specifically, Vlad acknowledges its unique status and enduring influence, even as he remains bullish on the broader crypto ecosystem rather than being a “bitcoin maxi.” Vlad shares his thoughts on price predictions, not

In this exclusive Market Mondays clip, Rashad Bilal and Troy Millings welcome back Caleb Silver, editor in chief of Investopedia, to break down one of the biggest stories shaking up the entertainment and financial worlds: Netflix’s potential $72 billion acquisition of Warner Brothers’ streaming assets. Was this deal ever real? And what does it mean for the power dynamics of streaming giants? Caleb Silver explains exactly what a monopoly is, tracing its history from the era of the railroads and the origin of U.S. antitrust laws to today’s streaming wars. The trio discusses how monopolies work, why the government steps in with antitrust policies, and how proximity to political power plays a bigger role in the stock market than ever before. You’ll get expert insights into: Why "Assets over Liabilities" is more than just a hoodie slogan—it's the ultimate metric in the current market. How and why the Federal Trade Commission cracks down on monopolies. The real meaning behind antitrus

In this clip from Market Mondays, hosts Rashad Bilal and Troy Millings sit down with financial analyst Caleb Silver to break down the current economic landscape and what lies ahead for 2026. The conversation starts with a historic event—the cancellation of the American jobs report—and what it signals for business journalists, policymakers, and everyday investors. Caleb Silver explains why, despite the anxiety over inflation and consumer confidence being at lows reminiscent of the Great Financial Crisis, the U.S. economy is in better shape than most people feel. The clip dives into key data points like updated unemployment rates, wage growth, and the impact of underreported layoffs and AI-driven changes in the job market. The discussion pivots to stock market trends, especially the dominance of the "Mag 7" mega-cap tech stocks. Troy Millings asks the crucial question: If the Mag 7’s run slows, can the rest of the S&P 500 pick up the slack? Caleb Silver provides deep insights into what bre

In this week’s episode of Earn Your Leisure, we sit down with Robinhood CEO Vlad Tenev for one of the most important conversations of the year. Fresh off a historic run that tripled Robinhood’s stock price, Vlad opens up about his proudest moment of 2025, the biggest misconceptions about the platform, and why he believes the retail investor is now the sophisticated investor. We also dive deep into the future of artificial intelligence, the evolution of predictive markets, the role of crypto in global access, and Robinhood’s mission to build a complete financial ecosystem. Vlad breaks down how AI is creating opportunity—not eliminating it—why he doesn’t believe we’re in an AI bubble, and how their new “Legend” model has transformed productivity at scale. From billion-dollar opportunities to the new Treasury-backed $1,000 investment accounts for every child born in the U.S., this episode is packed with insights on investing, innovation, and the future of fin