Earn Your Leisure

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 fu...

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 w...

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: EARNERS

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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...

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 exactl...

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 infla...

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 artifici...

In this insightful Market Mondays clip, Rashad Bilal, Ian Dunlap, and Troy Millings break down the most critical investing mistakes of the year and share powerful lessons for smarter investing going forward. Ian Dunlap highlights the missed opportunities during the market’s April run, emphasizing how not deploying capital during that crucial window was one of the biggest blunders. He reflects on the rare “guaranteed win...

In this clip from EYL, Rashad Bilal sits down with Ahmed Ben Chaibah to dive deep into Dubai’s booming real estate market, innovative investment strategies, and the power of personal branding. Ahmed Ben Chaibah shares his perspective on the unstoppable growth of the UAE property market, revealing year-on-year increases of up to 30% or even 40%. He recounts stories of skyrocketing villa rental prices and highlights how Dubai&r...

In this powerful clip from "EYL," David Shands sits down with Troy Millings to share his journey from working at the Cheesecake Factory to building a six-figure business selling T-shirts. David breaks down the essential mindset shifts and tactical strategies he used to turn his "off days" into $100 paydays, eventually quitting his job and scaling up his entrepreneurial dream.

You'll hear David’s advice on setting practical wo...

In this Market Mondays clip, Rashad Bilal, Ian Dunlap, and Troy Millings dive deep into Apple’s stunning market performance, silencing rumors about its decline and revealing why it’s still a top pick for smart investors. As the broader market shows volatility, Apple hits a 52-week high, positioning itself once again as a “safe haven” alongside tech giants like Microsoft and Google. Ian Dunlap explains why th...

Welcome to another insightful Market Mondays clip! In this dynamic conversation, Rashad Bilal, Ian Dunlap, and Troy Millings dive deep into Elon Musk's approach to investing and building wealth, discussing why the world's richest person chooses to focus on his own companies instead of diversifying into the stock market. The group reflects on Musk's revelation that, if he were to invest in stocks, his picks would be Google and Nvidi...

In this insightful clip from Market Mondays, Rashad Bilal and Ian Dunlap dive deep into the psychological side of trading and investing. Ian Dunlap shares his trading tip of the week, advising futures traders to manage fear, embrace bigger risks, and strategically increase the size of their trades for bigger rewards. He recommends going for 33 contracts on the S&P 500 and targeting 42 ticks, which can potentially result in sign...

In this episode of Earn Your Leisure, we sit down with Ahmed Ben Chaibah, the visionary founder of Aqua Fun, to break down why Dubai is becoming the #1 city in the world for entrepreneurs, investors, and anyone who wants true financial freedom.

We talk about how Ahmed built the world’s largest inflatable waterpark, scaled to 780 employees across 34 locations, and grew an audience of 100K without spending a dollar on ad...

In today's digital age, the internet is flooded with an endless stream of content waiting to be consumed. However, not everything you come across online serves your well-being or personal growth. This eye-opening episode delves into the detrimental effects that certain online content can have on your life, mental health, and overall productivity. From mindlessly scrolling through social media to watching negative news or being hook...

In this Market Mondays clip, Rashad Bilal and Ian Dunlap dive deep into the recent struggles of Novo Nordisk and explain why the stock’s steep drop isn’t an opportunity to buy. They break down Novo’s missed Alzheimer’s drug, compare Novo's margins and performance to Eli Lilly, and discuss the key issues behind GLP-1 drugs that have led to Novo’s downfall. Rashad Bilal likens the Novo-Lilly rivalry to M...

In this clip Robert Smith explained the broadband issue for HBCUs, student loans, and his solution. #robertsmith #morehouse #studentloans Link to Full Episode:    • Robert Smith on Being The Richest Black Am...   EYL University: https://www.eyluniversity.com Monthly Investment Deal: https://www.earnyourleisure.com/pages...

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In this Market Mondays clip, hosts Troy Millings, Rashad Bilal, and Ian Dunlap dive into the true driving force behind the AI revolution: ENERGY. While everyone is buzzing about artificial intelligence and GPUs, they break down why none of that matters without sufficient power to keep massive data centers running. Rashad Bilal starts the conversation by highlighting the often-overlooked opportunity in energy, emphasizing that the f...