Payne Points of Wealth

From Yale Law to Barbershop Tech | Ep. 226

In this episode of Payne Points of Wealth, we sit down with Songe LaRon, a dynamic New York City tech entrepreneur, Co-Founder and CEO of SQUIRE Technologies—the world’s leading all-in-one barbershop business management system. Songe shares his remarkable journey from growing up in Manhattan with artist parents, to earning a J.D. from Yale, practicing law at a top firm, and ultimately making the leap from a more certain future in corporate America to launch a tech company that’s transforming an entire industry.   We explore how his upbringing shaped his relationship with money, the entrepreneurial spark that led to founding SQUIRE in 2015, and the challenges of breaking into tech without a technical background. Songe reveals how he and his team scaled SQUIRE to serve over 32,000 professionals across three continents, raised nearly $150M in funding, and built a culture of innovation that now integrates AI to revolutionize barbershop operations.   This episode is packed with insights on funding a startup, lessons from running an actual barbershop, personal wealth philosophies, and the mindset required to turn an idea into an industry leader. Plus, Songe shares his thoughts on the future of AI in business and the importance of resilience in entrepreneurship.

The Investing Dilemma: Why Chasing AI Could Derail Your Wealth

Is the AI Bubble Finally Here??? The Roundtable We Needed In episode 225 of the Payne Points of Wealth, Ryan, Bob, and Chris tackle one of the most fundamental—and often overlooked—principles of investing: diversification. Why do so many investors ignore this simple rule and chase the hottest trends like AI stocks? We break down the psychology behind FOMO, the dangers of over-concentration, and why rebalancing your portfolio is one of the hardest—but most important—moves you can make. You’ll hear real-world examples, including a financial autopsy of a couple in early retirement who were unknowingly taking on massive risk. Plus, we share why protecting what you’ve built matters more than chasing the next big thing and how being “approximately correct” beats being “precisely wrong” every time. If you want to avoid costly mistakes and build true financial independence, this episode is a must-listen!

How a 25-Year-Old Immigrant’s Startup is Changing U.S. Immigration

In this week’s episode, Ryan, Chris, and Courtney sit down with Mihailo Bozic, a dynamic 25-year-old entrepreneur whose journey from Australia to New York City embodies the classic immigrant founder story. With Serbian roots and a background in Finance and Economics from the University of Western Australia, Mihailo has already launched two impactful startups tackling real-world problems. From his first venture Envited, a social media app revolutionizing student event planning, to his current company Migrate Mate [https://migratemate.co/], a job board helping immigrants find visa-sponsored roles in the U.S., Mihailo shares how he bootstrapped his way to $500K ARR in just three months and built a community of over 16,000 job seekers. We dive into: * The challenges of startup funding and scaling * How viral LinkedIn marketing helped Migrate Mate explode * Building a 15M+ follower base from a meme page * Lessons from pitching to VCs as an immigrant founder Given the uncertainty surrounding today’s labor market, the rapid rise of artificial intelligence, evolving U.S. immigration policies, and the shifting landscape of American entrepreneurship, this episode offers timely and thought-provoking insights into the state of the modern U.S. economy. Whether you’re an investor, an aspiring entrepreneur, an immigrant chasing opportunity, or simply someone who loves a good hustle story—this conversation is packed with inspiration, practical wisdom, and real-world perspective.

Is the AI Bubble Finally Here??? The Roundtable We Needed

All right, all right, all right—this week, it’s just the Payne Capital crew, no guests, no filters, just real talk. After a string of great interviews, we’re bringing it back to the roundtable to tackle the question everyone’s asking: Are we in an artificial intelligence bubble? Bob dives into market history and draws parallels to the tech boom of the '90s. Courtney shares what Wall Street strategists are saying and why the AI narrative is dominating every segment. Chris gives us the pulse from clients—some are all-in on AI, others are bracing for a crash. Ryan calls out the all-or-nothing mindset and why predicting the top is a fool’s game. We also dissect a real financial plan in our Financial Autopsy segment, helping a couple in their late 60s shift from aggressive growth to income-focused investing—without triggering massive tax bills. From margin debt mania to gold’s surprise rally, from diversification myths to emotional investing traps, this episode is packed with insights, laughs, and actionable advice.   Tune in to hear:   ✅ Are we in 1995 or 1999? Bob reads the market tea leaves. ✅ Why diversification still matters—even if AI is hot. ✅ How to avoid living by the sword and dying by the sword in your portfolio. ✅ The emotional toll of bear markets and how to prepare before they hit. ✅ A real-life case study on reducing risk, increasing income, and optimizing for taxes. Don’t miss this one—because when the tide goes out, you’ll want to be wearing the right financial swimwear.

The Human Edge in a Tech-Driven Economy

In this week’s episode of the Payne Points of Wealth, Bob, Ryan, and Chris sit down with Sara Uy, the dynamic 28-year-old founder of SellingSara, a New York-based sales training program. Together, they unpack the shifting landscape of the job market, the rise of AI in hiring, and why soft skills and emotional intelligence are more valuable than ever. Sara shares her firsthand insights into Gen Z’s job search struggles, the disconnect between employer expectations and hiring realities, and why Artificial Intelligence still can’t replace human intelligence—especially in sales. From cold calling in the age of call screening to what makes a top-performing salesperson, this episode delivers sharp insights, humor, and a front-line perspective on how AI is reshaping today’s labor market—and why human skills still matter more than ever.