Top Investing Mistakes to Avoid in 2026

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 why discipline, education, and conviction matter more than ever. Troy recommends starting small, truly understanding the businesses you invest in, and building knowledge for long-term success. Rashad Bilal brings a practical blueprint, sharing 10 essential steps every investor should follow in 2026: Create a budget using popular apps like YNAB, Monarch Money, or Rocket Money Set up systematic monthly investing (dollar cost averaging) Maximize retirement contributions for tax benefits Regularly review and update all beneficiaries Commit to continuous education by watching one documentary a week and reading one book every 60 days Map out actionable, accountable goals based on the “12 Week Year” strategy The crew agrees: the biggest investor mistake is not having a clear plan and the discipline to stick to it. If you want to set yourself up for real financial success in 2026, this conversation is your actionable guide! 👇 Drop your freedom number for 2026 in the comments and let us know what steps you’re taking to lock in your future. *Be sure to subscribe for more Market Mondays insights on wealth-building and financial mastery!* #MarketMondays #Investing2026 #MoneyMistakes #FinancialFreedom #RashadBilal #IanDunlap #TroyMillings #WealthBuilding #PersonalFinance #StockMarket #InvestmentTips #FinancialPlanningSee omnystudio.com/listener for privacy information.

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. For entrepreneurs and anyone fascinated by startups, Dave explains the meaning behind SQUIRE’s incredible $750 million valuation in clear, understandable terms. Listeners get an inside look at how investors determine value, the formulas behind equity stakes, and the significance of creating a diverse team with ownership in the company. Dave and Rashad discuss the evolution of the company’s ownership table, the benefits and drawbacks of equity dilution, and why keeping control is just as vital as raising capital. With over 32,000 barbershops and millions of clients in their ecosystem, this conversation is packed with honest advice, motivation, and the real business insights you won’t get elsewhere. *Key Highlights:* How Dave Salvant and SQUIRE confronted and overcame biases in marketing to different communities The evolution from direct sales to scalable processes in the barbershop industry Real talk about company valuation, investor relationships, and how much a startup is really worth Strategies for building wealth in diverse communities through equity and ownership The unique challenges and wins in the journey from hands-on founder to scaling a business with a multi-million dollar market cap If you want motivation and insider knowledge on what it really takes to launch, scale, and retain control of a high-growth tech company, this is the clip for you! *#SQUIRE #BarbershopBusiness #Startups #BusinessGrowth #Entrepreneurship #Valuation #EYL #WealthBuilding #DiversityInTech*See omnystudio.com/listener for privacy information.

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 purchasing power in Africa, the surprising reality that most travel within Africa is by Africans themselves, and which countries currently offer the best real estate buying opportunities.   #EarnYourLeisure #AfricaInvesting #AfricanRealEstate #DiasporaInvesting #GlobalWealth #RealEstateEducation #InvestInAfrica #FinancialLiteracy #WealthBuilding #EmergingMarketsSee omnystudio.com/listener for privacy information.

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 for the S&P 500 and highlights that although volatility and possible downturns may appear towards the end of the year, the outlook remains strong—especially for those who stay focused, prepared, and ready to buy during market pullbacks. The trio also discusses the importance of focusing on decade-long investment horizons versus getting caught up in short-term fluctuations. The lesson is clear: building real, generational wealth requires patience and the discipline to invest, even when the market looks shaky. You’ll also hear sharp insights into the risks of market gatekeeping, venture capital exclusivity, and the power of preparation—plus why every downturn is actually a buying opportunity for the informed investor. *Key takeaways from this Market Mondays clip:* 2026 will likely bring volatility and possibly a market free fall, but long-term winners will use it as an accumulation year. Focus on building your portfolio with quality assets—don’t waste time waiting for perfect conditions. Expect increased spending in tech and infrastructure, deregulation benefits (especially in AI), and more tailwinds for growth. Don’t get distracted by crash predictions—stay focused on a 10-year investment plan. Downturns are opportunities for those who are prepared with cash and a strategy. Whether you’re new to investing or a seasoned market participant, these insights will help you ride out the coming turbulence and come out stronger. Listen in for practical advice and proven strategies from some of the sharpest financial minds. If you found this clip valuable, hit the like button, share your thoughts in the comments, and subscribe to Market Mondays for more wealth-building conversations! *Hashtags:* #MarketMondays #Investing2026 #LongTermWealth #AssetAccumulation #FinancialFreedom #TechStocks #Finance #StockMarket #InvestingTips #SP500 #Bitcoin #AIinvestingSee omnystudio.com/listener for privacy information.

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? What if the service was subpar? Both hosts agree that monetary gifts should go hand-in-hand with outstanding service and positive energy—but getting the etiquette right can sometimes confuse even the most well-meaning among us. Whether you live in a home or apartment, rely on daily or weekly help, or simply want to ensure you’re not missing an important gesture, this clip is packed with practical tips, etiquette reminders, and candid stories about why tipping matters—not just for gratitude, but for better service in the future. Ready to level up your holiday tipping game and show some love to those who support you all year long? Rashad Bilal and Ian Dunlap have you covered! *Hashtags:* #TippingEtiquette #HolidayTipping #YearEndGifts #ServiceWorkers #BlackOutPodcast #IanDunlap #RashadBilal #Gratitude #PodcastClip #LifeAdvice #BetterService #SupportYourCommunity #Appreciation #CustomerService #MonetaryGiftsSee omnystudio.com/listener for privacy information.

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, with most quick successes not repeating themselves in the markets. Rashad reinforces the pitfalls of following hype or hearsay without understanding companies or their industries, and both stress why relying on others for entry and exit signals is dangerous. Drawing on Warren Buffett’s philosophy, Rashad recalls a conversation with Jeff Bezos about the power of getting “rich slow”—and why this tried and true method remains unpopular despite its proven results. The key takeaway? While chasing overnight success is tempting, patience, discipline, and a solid plan will always outperform reckless speculation in the long run. *Key points in this clip:* Why you must let your trades breathe and use longer targets strategically How sports wagering platforms like Robinhood are attracting futures traders The biggest mistakes young investors make, from chasing meme stocks to lack of market discipline Why fast money often leads to long-term losses The timeless wisdom of building wealth slowly instead of seeking quick wins *Learn practical wisdom from Rashad Bilal and Ian Dunlap on becoming a smarter, more disciplined investor—because sometimes the slow road is the fastest way to lasting wealth.* #MarketMondays #TradingTips #Investing #WealthBuilding #IanDunlap #RashadBilal #StockMarket #FuturesTrading #Robinhood #Discipline #FinancialFreedom #GetRichSlow #MemeStocks #NFTs #LongTermInvesting #SportsWageringSee omnystudio.com/listener for privacy information.

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 sits in the middle—reliable, but not quite on the same level as investment giants like Vanguard or BlackRock. Rashad pushes back, arguing IBIT deserves the top spot. He stresses the unprecedented security of a product backed by BlackRock, the largest asset manager ever. In his view, if you really believe in Bitcoin’s growth potential, IBIT offers the purest 1:1 exposure, removing the variables that platforms like Coinbase face during earnings reports or market downturns. Troy shares his perspective, agreeing IBIT is the best option for investors wanting direct bitcoin exposure. He explains that owning IBIT is not exactly the same as holding Bitcoin yourself, but it provides a simple route to gain exposure through a fund structure. Coinbase, meanwhile, earns revenue from transaction and subscription fees, making it a strong but somewhat cyclical contender. The trio concludes by ranking the three: IBIT first for its direct and secure Bitcoin exposure, Coinbase second for its business model, and MicroStrategy third due to its current risk factors. Throughout, they also briefly address their broader crypto confidence, with Rashad sharing that Bitcoin and Ethereum are the only coins he’s truly bullish on for the long term. If you're wondering how to get started with crypto investing—or want to understand which publicly traded options might suit your strategy—this clip is packed with insights, debates, and expert perspectives. *Hashtags:* #CryptoStocks #Coinbase #MicroStrategy #IBIT #BitcoinETF #MarketMondays #Investing #CryptoInvesting #StockMarket #BlackRock #BitcoinSee omnystudio.com/listener for privacy information.

This week on Earn Your Leisure, we sit down with Songe LaRon 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. Songe 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 #SongeLaRon #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.