What do Jeffrey Epstein, private equity-owned insurance, and AI have in common? Josh sits down with bestselling author, co-founder of the media company Puck, and financial journalist William D. Cohan to unpack the forces shaping today’s financial landscape. Bill breaks down the rise of Apollo Global Management, its connections to controversial figures, and the risks that come with firms like Athene controlling massive swaths of retirement assets.

They dig into the structural flaws in private equity-backed insurers, the dangers of borrowing short and lending long, and how rising interest rates could expose cracks in the system. Josh and Bill also explore how AI is reshaping investment banking and journalism, and why the debate over intellectual property, automation, and job security is just getting started.

Can't get enough of The Financial Quarterback? Click ‘Subscribe’ so you never miss a play. If you’re enjoying the show, leave a 5-star rating and drop a review—it helps keep the game going!

Check out Bill Cohan's work:

Power Failure: The Rise and Fall of an American Icon – Buy the book

Puck – puck.news

Are the markets flashing warning signs or presenting rare opportunities? Josh kicks off the show with a deep dive into the latest market turmoil, breaking down how volatility, interest rates, and global headlines are shaking investor confidence. He explores the power of strategic and tactical diversification, the importance of time in the market, and why even bear sentiment can point toward future gains.

Callers weigh in with questions on everything from recession-proof investments and 401(k) loans to the real value of bonds, annuities, and long-term planning. Josh also shares quick takes on China trade tensions, financial anxiety, and even the economics behind pop culture and politics.

Original Air Date: April 19th, 2025

Can't get enough of The Financial Quarterback? Click ‘Subscribe’ so you never miss a play. If you’re enjoying the show, leave a 5-star rating and drop a review—it helps keep the game going!

​Did Jerome Powell just shift the economic narrative? Josh reacts in real time to Powell’s April 15 remarks at the Economic Club of Chicago, breaking down his comments on inflation, tariffs, and the growing risks in private credit markets. He questions whether Powell’s outlook reflects neutral policy or political influence, especially in light of ongoing tension with former President Trump.​

Josh contrasts Powell’s inflation concerns with falling prices in areas like oil and groceries, challenges the Fed’s stance on tariffs, and examines the potential impact of unregulated private lending on future market stability. He also explores the growing friction between Powell and Trump, and what that could mean for future policy.​

Audio sourced from Powell’s April 15, 2025 speech at the Economic Club of Chicago: https://www.federalreserve.gov/newsevents/speech/powell20250416a.htm

​

Can't get enough of The Financial Quarterback? Click ‘Subscribe’ so you never miss a play. If you’re enjoying the show, leave a 5-star rating and drop a review—it helps keep the game going!

Are baseball stats the secret to smarter investing? Josh steps up to the plate with a fresh, fun take on personal finance through the lens of America’s favorite pastime. From on-base percentage to wins above replacement, he draws comparisons between your favorite stats and core financial strategies. Whether it’s knowing when to swing big or play it safe, Josh shows how the logic behind baseball’s most trusted numbers can help guide your money moves.

Then in 'Extra Points,' Josh unpacks what it means when private equity firms start buying stakes in your favorite team, like the recent move with the San Francisco Giants

Can't get enough of The Financial Quarterback? Click ‘Subscribe’ so you never miss a play. If you’re enjoying the show, leave a 5-star rating and drop a review—it helps keep the game going!

Is playing financial defense smarter than chasing big returns? Josh welcomes Curtis May, creator of Practical Wealth Advisors and host of the Practical Wealth Show, to explore why protecting assets and mastering financial fundamentals matter more than flashy investment tactics. They dive into Curtis's contrarian philosophy, challenging mainstream ideas like "buy term and invest the difference," and discuss how continuous education and clear financial principles help investors avoid costly mistakes.

Josh and Curtis also talk through the power of plugging financial leaks, the value of liquidity, and why investing in your own knowledge is the foundation for lasting wealth. Drawing inspiration from events like the Infinite Banking Think Tank, they unpack practical strategies designed to help fortify your financial future.

Can't get enough of The Financial Quarterback? Click ‘Subscribe’ so you never miss a play. If you’re enjoying the show, leave a 5-star rating and drop a review—it helps keep the game going!

Check out Curtis May:

Website: practicalwealthadvisors.com

Podcast: The Practical Wealth Show

How much should the Tooth Fairy leave under the pillow in 2025, and what does that tell us about the state of the economy? Josh dives into how inflation is creeping into even the smallest corners of American life, including the Tooth Fairy’s wallet. He breaks down the latest data on falling Tooth Fairy payouts, what it says about inflation, and how parents can turn these moments into financial lessons for their kids. Plus, he shares tips on using allowances to teach responsibility without letting kids fall into bad money habits. Then in 'Extra Points,' Josh weighs in on Southwest Airlines shaking up their free bag and open seating policy and how it could hit your travel budget.

Can't get enough of The Financial Quarterback? Click ‘Subscribe’ so you never miss a play. If you’re enjoying the show, leave a 5-star rating and drop a review—it helps keep the game going!

Is your financial plan more complicated than it needs to be? Josh sits down with Jon Luskin, CFP and board member at the John Bogle Center for Financial Literacy, to unpack why simplicity might be the most overlooked strategy in personal finance. Known for helping DIY investors cut through the noise, Jon shares why single-fund solutions like target date and balanced funds can go further than bloated portfolios filled with unnecessary holdings. They cover the foundations of smart financial planning, from term life and disability insurance to revocable living trusts and emergency letters. Jon explains how to protect yourself with the right insurance, how to avoid overthinking your portfolio, and why simplicity doesn’t mean sacrificing results. It means staying focused on what really matters.

Can't get enough of The Financial Quarterback? Click ‘Subscribe’ so you never miss a play. If you’re enjoying the show, leave a 5-star rating and drop a review—it helps keep the game going!

Why are eggs still so expensive—and will prices ever go back down? Josh breaks down why everyday goods like eggs, gas, and groceries cost so much more today. He looks at the real drivers behind inflation and how it’s hitting your wallet in ways you might not expect. Plus, Josh plays a round of "The Price Ain’t Right," comparing what key items cost in 1980 versus today to show just how far your dollar stretches. Then in 'Extra Points,' Josh weighs in on the state of tipping culture in America and how it’s adding to inflation pressures at the checkout counter.

Can't get enough of The Financial Quarterback? Click ‘Subscribe’ so you never miss a play. If you’re enjoying the show, leave a 5-star rating and drop a review—it helps keep the game going!

How do you build a retirement that’s financially secure and personally fulfilling? Josh sits down with retirement expert Fritz Gilbert, founder of The Retirement Manifesto and author of Keys to a Successful Retirement, to break down the financial and emotional side of life after work.

Fritz shares his own journey from corporate America to an early retirement in the Appalachian Mountains, where he now writes, volunteers, and helps others navigate the transition. He and Josh dive into strategies for managing market downturns, the importance of a diversified withdrawal plan, and why so many retirees underspend out of fear. They also tackle the psychology of retirement: how to stay engaged, find purpose, and avoid the common traps that can lead to financial and emotional stress.

Can't get enough of The Financial Quarterback? Click ‘Subscribe’ so you never miss a play. If you’re enjoying the show, leave a 5-star rating and drop a review—it helps keep the game going!

Are pensions a relic of the past? Josh dives into the rapid decline of pensions and what it means for retirement planning today. With companies slashing pension plans to cut costs and boost stock prices, workers are now forced to rely on 401(k)s and other personal savings. Josh breaks down why pensions are disappearing, the challenges facing public sector plans, and how retirees can build their own steady income streams. From annuities to dividend stocks and bonds, he explores ways to replace the security pensions once provided. Then in 'Extra Points,' Josh looks at the Boeing strike over pensions and what it reveals about the future of retirement benefits.

Can't get enough of The Financial Quarterback? Click ‘Subscribe’ so you never miss a play. If you’re enjoying the show, leave a 5-star rating and drop a review—it helps keep the game going!