How Two Friends Built a $750 Million Barber Tech Company

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 #TechStartupsSee omnystudio.com/listener for privacy information.

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*See omnystudio.com/listener for privacy information.

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, noting the surprises in bitcoin’s journey and its deep-rooted prominence among enthusiasts. The conversation then pivots to Robinhood’s innovative prediction markets, where Vlad explains how Robinhood has quickly become a leader. From just one contract about the presidential election to over 1,500 diverse contracts, prediction markets have become the company’s fastest-growing business segment. These markets not only cover politics but also expand into sports and emerging fields like AI model performance, drawing in traders and market participants from traditional finance backgrounds. Vlad breaks down how prediction markets differ from traditional sports betting—enabling live, dynamic trading as events unfold, thus introducing a new "wagering" experience. This disrupts conventional betting and offers users a way to trade based on real-time market information, making sports betting companies reconsider their strategies. From AI to sports and elections, prediction markets are changing how information is shared and traded. Vlad predicts these markets will become a new, valuable source of crowd-sourced intelligence, enabling individuals to leverage their unique insights and move beyond conventional wisdom. Don’t miss this dynamic conversation about the intersection of technology, finance, and the future of trading. Vlad Tenev explains why Robinhood is defining a new wave of innovation—making global finance accessible and reimagining prediction markets for everyday traders. *Hashtags:* #Crypto #Bitcoin #Robinhood #VladTenev #PredictionMarkets #Stablecoins #Investing #FinanceInnovation #Tokenization #AI #SportsBetting #GlobalFinance #EYL #RashadBilal #FutureOfFinanceSee omnystudio.com/listener for privacy information.

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 antitrust cases and how they protect consumers and competitors. The surprising influence of presidential administrations in shaping business deals and market outcomes. What the Netflix x Warner Brothers mega-deal could signal for the future of entertainment and investing. Whether you’re a budding investor, an industry insider, or just a fan of Market Mondays’ fresh takes, this clip offers a crash course in market mechanics, business strategy, and why your proximity to power could make or break your portfolio. Drop your thoughts in the comments and don’t forget to hit subscribe for all the latest Market Mondays insights! *Hashtags:* #MarketMondays #Investing #Netflix #Monopoly #Antitrust #WarnerBros #StreamingWars #AssetsOverLiabilities #CalebSilver #FinancialEducation #Stocks #BusinessNewsSee omnystudio.com/listener for privacy information.

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 breadth in the market really looks like, highlighting why recent rallies in healthcare, financials, and commodities matter for investors seeking diversification. Walmart’s shift to the Nasdaq and its surprising outperformance versus other tech giants is put under the spotlight. Caleb Silver explains why Walmart's move is strategic, aiming for a spot among elite growth stocks and inclusion in popular indices. Looking ahead, the clip identifies where opportunities may exist for investors going into 2026, including sector rotation, the resurgence of healthcare and biotech, and the importance of looking at undervalued mid- and small-cap stocks. Caleb Silver explains the difference between small, mid, large, and mega-cap companies, and how those categories affect investment strategies in a world dominated by trillion-dollar giants. If you want to understand where the U.S. market, consumer sentiment, and investor behavior are heading, this clip is packed with actionable analysis. Plus, get a behind-the-scenes glimpse of what investors and financial researchers are really looking up as we close out the year. *Hashtags:* #MarketMondays #CalebSilver #EconomicOutlook #2026Forecast #StockMarket #Investing #Walmart #Mag7 #MidCapStocks #SmallCapStocks #FinancialAnalysis #ConsumerConfidence #Inflation #JobMarket #SectorRotation #WallStreet #Nasdaq #S&P500 #BullMarket #InvestopediaSee omnystudio.com/listener for privacy information.

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 finance. Whether you’re a trader, entrepreneur, or long-term investor, this is a conversation you don’t want to miss. #EarnYourLeisure #VladTenev #Robinhood #Investing #ArtificialIntelligence #Crypto #PredictiveMarkets #MarketMondays #FinancialEducation #WealthBuildingSee omnystudio.com/listener for privacy information.

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” and urges viewers to always be ready to act when markets present powerful opportunities. Ian also advises investors and traders to hunt for the next big sector winner – naming quantum computing as a future disruptor and encouraging in-depth research to find groundbreaking companies for 2027 and beyond. Troy Millings echoes the importance of sticking to a disciplined plan, especially in times of market downtrends. He points out how ETFs and index funds soared for those who maintained their investments, and shares personal stories about leveraging ETF positions for significant gains in the semiconductor space. Troy’s experience with trades like XOXL and understanding the impact of ETF splits adds practical value for anyone looking to navigate stock and options trades with confidence. This clip also tackles the lessons learned from short market pullbacks, such as the November 5% dip, and how the uncertainty in sectors like AI technology can turn into profitable opportunities for those prepared to act. Plus, the team shares candid moments about overcoming losing trades and remaining steadfast in their long-term investment strategies. Whether you’re a beginner or a seasoned investor, this Market Mondays discussion will help you identify common mistakes, strategize for future wins, and learn from top minds in finance. Watch now to level up your investment approach, discover which sectors to watch, and take advantage of hidden market moments! *#MarketMondays #InvestingMistakes #StockMarket #ETFs #OptionsTrading #QuantumComputing #FinancialEducation #IanDunlap #RashadBilal #TroyMillings #InvestingTips #StockMarketNews #AIStocks #ETFInvesting #FinanceYouTube*See omnystudio.com/listener for privacy information.

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’s competitiveness fosters both opportunity and challenge for residents, investors, and entrepreneurs. The conversation uncovers the structures behind property transactions in Dubai – including mortgages, off-plan purchases with developer payment terms, and even crypto payments. Rashad Bilal raises important questions about the sustainability of rapid growth in cities like Dubai and New York, especially regarding wealth gaps and affordable housing. Ahmed Ben Chaibah responds by painting a picture of Dubai as a “layered onion” where luxury and affordability exist side by side. We also explore Ahmed Ben Chaibah’s intentional personal branding, his collaborations, and why authenticity matters in business. You'll hear how he built and manages nine businesses and 91 investments, staying involved through tightly focused, efficient meetings. Plus, discover why Dubai’s license plate culture has become a striking symbol of wealth, with single-digit plates selling for millions. Get practical insights into business operations, branding, and life in Dubai, straight from one of the region’s most dynamic entrepreneurs. *Highlights:* Explosive growth of real estate in Dubai and its implications How Dubai’s property system works (mortgages, payment terms, crypto) The balance of wealth and affordability in Dubai Entrepreneurial routines and time management The intentionality behind personal branding The fascinating world of Dubai’s luxury license plates Whether you’re interested in investing in Dubai, scaling your own ventures, or building a strong personal brand, this clip is full of actionable advice and eye-opening stories. *Hashtags:* #DubaiRealEstate #AhmedBenChaibah #EYL #InvestInDubai #PersonalBranding #Entrepreneurship #PropertyInvestment #BusinessGrowth #LuxuryLifestyle #TimeManagement #WealthMindsetSee omnystudio.com/listener for privacy information.

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 work goals (not just sales goals), transitioning out of your 9-to-5, and the importance of persistence—especially when facing rejection. He outlines his “life cycle of a good idea,” touching on excitement, evolution, engagement, and expansion, and how to carry momentum through each stage. Troy challenges David on the fine line between persistence and annoyance in sales, sparking a real conversation about how to overcome the fear of selling and why most people are conditioned to say "no" first. Hear how David converted sales after the second or even third "no"—and how his coaching clients have unlocked new income just by increasing their daily sales asks. Perfect for aspiring entrepreneurs and anyone ready to make their side hustle their main gig, this clip delivers actionable steps you can start using today. From building consistency to tracking your actual work instead of just the outcomes, David and Troy break down the real formulas behind hitting $250K a year selling any product. Don't miss this inspiration-packed conversation! **Key topics covered:**  - How to set daily work goals for reliable results  - Why persistence and overcoming “no” matters in sales  - The true process for transitioning out of your day job  - The “life cycle” stages of every business idea  - Breaking down sales fear and building resilience  - Why tracking your outreach matters more than tracking revenue **Hashtags:**  #Entrepreneurship #SalesStrategy #SideHustle #SmallBusiness #Persistence #DavidShands #TroyMillings #BusinessMindset #BlackOutPodcast #SuccessTips #HowToSell #WorkSmart #DailyHabits 👇 Watch, learn, and start building your $250K journey today!See omnystudio.com/listener for privacy information.