What if you could earn short-term rental yields without the short-term rental headaches? As major cities continue to regulate away 3-day stays, investors are shifting their focus to the “Goldilocks” of real estate: the midterm rental. Jeff Hurst, the CEO of Furnished Finder and former President of VRBO, joins us to explain why the 30-to-90-day…
I sat down with Ron Lieber, the New York Times “Your Money” columnist, to tackle one of the most stressful financial decisions any family faces: the cost of college. With headlines screaming about AI-driven job market disruptions and tuition hitting record highs, we’re digging into the math and the mindset shifts required to navigate higher…
Joe and I tackle questions about the complexities of early retirement at age 60 and the most efficient withdrawal strategies for lifelong security. This episode explores both the technical and psychological aspects of “spending down”—from balancing Social Security timing with your investment accounts to deciding if you should spend every last penny before you’re gone….
Caregiving is a massive responsibility that often falls on family members, usually as an unpaid role. For parents of children with autism, this doesn’t just mean managing the day-to-day, it means planning for a future that extends far beyond their own lives. Keith Wargo, the CEO of Autism Speaks, joins me to bridge the gap…
Joe and I are catching up in person to dive into a new set of listener questions. From navigating the complexities of the current real estate market to strategic tax planning for retirement, this episode explores both the technical and psychological aspects of building wealth. Whether you’re wondering how to handle a sudden windfall or…
Joe and I traveled to the campus of Texas A&M University-Texarkana for a very special live recording. We were joined by Jay Davis, the Executive Director of Financial and Entrepreneurship Engagement, to answer questions from an incredible audience of students. Whether you’re just starting your career or looking to “reset” your habits, this episode covers…
What do student loans, early retirement, and Airbnb have in common? They’re the three questions we’re tackling in today’s episode, and each one forces you to think about uncertainty, flexibility, and whether the “right” financial move on paper is actually the right move for your life. Joe and I answer three listener questions. KJ has…
Jon McNeill, the former President of Tesla and former COO of Lyft, discusses the intersection of innovation, leadership, and the future of technology. Jon shares behind-the-scenes stories of scaling two of the most disruptive companies in modern history and offers a masterclass on how to build “acceleration” into your own career and business ventures. We…
In this Q&A episode, Joe and I answer three listener questions that wrestle with the gap between plans and reality. Bringham is 23, recently awarded 100% VA disability ($4,300/month for life), and has mapped out a detailed 30-year plan: buy a house, have 2-3 kids, become a stay-at-home dad, return to work after they graduate,…
This month’s jobs report looks strong on the surface, with 178,000 jobs added and unemployment ticking down—but a closer look tells a more complicated story. When I compare it against other data like job openings and layoffs, it still points to a slower, low-hiring environment, raising the question: is this a real shift, or just…