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 year, and whether AI or rising haircut costs could disrupt the barber industry. EYL University: https://eyluniversity.com #EarnYourLeisure #Squire #SonnyAdams #DaveSalvant #StartupJourney #Fundraising #VentureCapital #BlackFounders #Entrepreneurship #TechStartups

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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 intense scrutiny. The duo also unpacks Oracle’s position as the fourth-largest cloud provider in the U.S., the spike in credit default swaps, and the impact of negative sentiment as the company’s massive investments raise eyebrows. Troy discusses how Oracle’s evolution—from enterprise software to subscriptions, to AI, and now cloud services—shows resilience, but also warns that market and government connections (like those with Larry Ellison) play a significant role in Oracle’s prospects. For anyone trying to navigate the choppy waters of tech stocks, this analysis offers historical insight, practical entry strategies, and candid takes on where Oracle might be heading next. Don’t miss out if you’re watching cloud stocks or considering Oracle for your portfolio. *Chapters Include:*

• Oracle’s Stock Pullback: Buy Now or Wait?
• Cloud Profitability: The Long Play for Investors
• Oracle vs. Amazon, Google, and Microsoft in the Cloud Race
• CAPEX and Margin Pressures Explained
• Market Sentiment & Credit Default Swaps: What Investors Should Know
• The Larry Ellison Factor: Government Ties & Future Outlook

*Drop a comment below:* Are you bullish or bearish on Oracle? Do you agree with Ian Dunlap’s price target or see a different opportunity? *Subscribe to Market Mondays for more sharp investing insights every week!* *#Oracle #CloudComputing #IanDunlap #TroyMillings #TechStocks #MarketMondays #Investing #OracleStock #LarryEllison #StockMarket*

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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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