Earn Your Leisure

Sonny Adams and Dave Salvant, the dynamic duo behind Squire, a cutting-edge barber-tech platform, share their incredible journey of building a $750 million company. They dive into their early days, overcoming technical hurdles, and why they offered their services for free initially. Fundraising insights reveal the challenges black founders face, while their focus on community and AI innovation showcases their unique market position. The conversation also touches on the impact of COVID on their growth and how they plan to empower barbers everywhere.

In this discussion, market commentator Ian Dunlap shares insights on Oracle’s stock pullback and whether it’s a good time to invest. He advises waiting for a price drop to around $160 before buying. Ian cautions that the current market won’t deliver Nvidia-level returns. Troy Millings highlights the delayed nature of cloud profitability and compares Oracle's journey to that of giants like AWS and Google. They also examine Oracle's position as the fourth-largest U.S. cloud provider and the potential impact of its political connections, especially regarding Larry Ellison.

Ryan Leslie, a music producer and entrepreneur known for his innovative approach to fan engagement, reveals how he generated $2 million from an album that only sold 17,000 copies. He discusses his unique strategy of using text messaging to connect with fans, converting inquiries into sales effectively. Ryan emphasizes the value of understanding fan data for successful touring and highlights why he prefers digital products for their scalability. He also shares insights on building deep relationships with niche audiences, showcasing how passion can lead to substantial wealth.

Vlad Tenev, co-founder and CEO of Robinhood, discusses the future of crypto, emphasizing its global impact and the importance of tokenization. He highlights how stablecoins provide financial stability in developing countries and shares insights on the evolving role of Bitcoin within the broader crypto landscape. Vlad also introduces Robinhood's rapid rise in prediction markets, revealing how they’ve expanded from one contract to over 1,500, covering diverse fields from politics to AI, all while encouraging crowd intelligence in trading.

Caleb Silver, Editor in Chief of Investopedia and a finance commentator, dives into the implications of Netflix's rumored $72 billion acquisition of Warner Bros. He uncovers the dynamics of monopolies, tracing their roots from railroads to today's streaming wars. Caleb explains the role of the FTC in antitrust enforcement and how political power influences major deals. The conversation highlights why understanding 'Assets over Liabilities' is crucial for investors and what this mega-deal could mean for the future of the entertainment landscape.

Caleb Silver, a renowned financial journalist and market analyst, joins to dissect the economic landscape heading into 2026. He covers the implications of the canceled jobs report and contrasts low consumer confidence with steady unemployment and wage growth. Silver highlights the dominance of the 'Mag 7' tech stocks and questions if other sectors can bolster the market. He also discusses Walmart's strategic move to Nasdaq and explores emerging opportunities in healthcare, financials, and mid-caps as the economic tide shifts.

Vlad Tenev, Co-founder and CEO of Robinhood, shares exciting insights from his journey in reshaping retail investing. He discusses why retail investors are now more sophisticated and the role of AI in enhancing productivity while creating new job opportunities. Vlad reveals a bold initiative to provide U.S. newborns with $1,000 investment accounts, exploring its potential impact. He also reflects on the future of crypto, the rise of prediction markets, and how Robinhood aims to democratize finance for everyone.

Explore the most critical investing mistakes of the year, including missed opportunities during April's market surge. Learn about the significance of sticking to a disciplined investment plan, especially in downturns. Delve into the benefits of ETFs and index funds, backed by real-life success stories in the semiconductor sector. Discover how to leverage market pullbacks for smart buys and keep an eye on future disruptors like quantum computing. Gain insights on risk management and the importance of having exit strategies to navigate challenging trades.

Ahmed Ben Chaibah, an entrepreneurial powerhouse in Dubai's real estate scene, shares insights on the city's remarkable property market. He reveals staggering yearly growth rates of 30-40%, as well as the dynamics of villa rental prices. The discussion touches on unique property transaction methods, including crypto payments. Ahmed addresses sustainability and wealth gaps, describing Dubai as a layered economy where luxury meets affordability. He also shares his booming businesses and the impact of intentional branding. Finally, the allure of Dubai's luxury license plates as status symbols adds a fascinating twist.

David Shands, an entrepreneur and sales coach, shares his inspiring journey from the Cheesecake Factory to a six-figure T-shirt business. He reveals effective strategies for turning 'off days' into $100 paydays and the importance of setting practical work goals over just revenue targets. David emphasizes the 'life cycle of a good idea,' which includes stages like excitement and expansion. They discuss overcoming rejection in sales, highlighting how persistence can change a 'no' into a 'yes'. This conversation is packed with actionable insights for aspiring entrepreneurs.