Josh Jalinski has been a Five Star Wealth Manager for the last five years in a row! He was named as an Advisor of the Year by Senior Market Advisor magazine.* He has also been selected for the Top of the Million Dollar Round Table, an association of financial professionals.
Ep 49 - Building a Retirement Paycheck That Lasts
How do you turn your retirement savings into a steady paycheck? Josh guides us through the shift from building wealth to making it last. From dynamic withdrawal strategies to tax-smart income planning, he lays out how inflation, healthcare costs, and market volatility can impact your financial future—and what you can do to stay protected. Then in 'Extra Points,' Josh answers a listener question about navigating retirement with limited savings.
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FROM THE ARCHIVES: Ed Slott Breaks Down the Roth IRA Loophole Billionaires Use
Are you making costly mistakes with your IRA? Josh revisits a conversation with Ed Slott, one of the country’s top IRA and retirement tax experts. Known as America’s IRA Expert, Ed has built a career helping people avoid costly tax mistakes when managing their retirement savings. With retirement planning constantly evolving, his insights remain as relevant today as ever, especially with ongoing tax policy debates and the increasing importance of Roth IRAs.
Josh and Ed break down the tax traps hiding in traditional retirement accounts, why Roth IRAs can be a game-changer, and how permanent life insurance might be the most underrated financial tool in retirement planning. They also touch on real-world examples—like Peter Thiel’s massive Roth IRA—showing just how powerful tax-free strategies can be when used correctly.
Original Air Date: September 4th, 2021
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Ep 48 - Could an Annuity Be Your Retirement Game-Changer?
Annuities—love them or hate them, they’re everywhere in retirement planning. Josh breaks down exactly what annuities are, how they work, and whether they actually make sense for your financial future. From fixed to variable to indexed annuities, he covers the different types, how insurance companies use them, and the key factors to watch out for—like fees, surrender charges, and payout structures. He also digs into why annuities can feel like a pension and whether they’re the right fit for retirement security or just another sales pitch.
Then in 'Extra Points,' Josh looks at the classic lottery winner dilemma—should you take the lump sum or the annuity payout? He lays out the numbers, the risks, and why the right choice depends on more than just the jackpot size.
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How Politics and the Economy Collide—And What It Means for You w/ Charles Wheelan (Naked Economics)
What happens when politics and economics collide? Josh sits down with Charles Wheelan, economist, Dartmouth professor, and author of the best-selling Naked Economics series, to explore the financial and political forces shaping our world. From ranked choice voting to the realities of inflation, global risks, and government spending, Charles breaks down why these issues matter and how they affect everything from your investments to your daily life.
Josh and Charles get into the push for political reform, the challenges of balancing capitalism and democracy, and why some economic myths just won’t die. They also take a detour into Charles’ experiences traveling the world, how different cultures handle money, and what his time in the Amazon taught him about life and economics.
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Ep 47 - How to Avoid Costly Tax Errors and Maximize Deductions
How can small business owners make the most of their tax deductions? Josh continues with his small business tax series, focusing on the crucial topic of deductions and the mistakes entrepreneurs need to avoid. From home office write-offs to maximizing tax credits, he unpacks strategies to help reduce taxable income while staying compliant. Josh also highlights the importance of accurate record-keeping and shares practical tips to simplify tax prep and sidestep common errors.
Then in 'Extra Points,' the team discusses Taylor Swift’s Eras Tour and its surprising impact on small businesses, sparking a debate about the intersection of culture and commerce.
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Beating the IRS at Their Own Game w/ Dan Pilla (Pilla Tax)
What’s your best defense against the IRS? Josh brings back renowned tax litigation expert Dan Pilla to uncover strategies for navigating today’s complex tax landscape. As the head of Pilla Tax and author of 14 books on tax-related issues, Dan shares his decades of experience fighting and winning cases against the IRS. Together, they dive into expiring provisions of the Tax Cuts and Jobs Act, rising IRS audits, and how small business owners and individuals can protect themselves with proper documentation and smart planning.
Josh and Dan break down home office and mileage deductions, year-end tax-saving strategies, and common pitfalls that could trigger IRS scrutiny. They also explore how to navigate disputes with the IRS, from wage levies to appeals, and the importance of staying proactive with your tax strategy.
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Ep 46 - Structuring Your Small Business to Save on Taxes
How should small business owners navigate the maze of taxes? It's tax prep month on The Financial Quarterback Podcast, and Josh begins by laying out the groundwork for small business tax management. From picking the right structure—LLC or S Corp—to the critical role of keeping accurate records, he unpacks what entrepreneurs need to know before deductions and strategies take center stage in the next episode. Along the way, Josh explores key tax categories like income and self-employment taxes and emphasizes the value of hiring a trustworthy financial team to avoid costly mistakes.
Then in 'Extra Points,' Josh shares his thoughts on Netflix’s decision to build a $900 million studio in New Jersey. What does this mean for small businesses in the area? And how do these massive tax breaks stack up against what everyday entrepreneurs face?
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The Most Overlooked Tax Breaks for Small Businesses w/ Mark Kohler
What’s the cost of procrastinating on your taxes? Josh explores this with CPA, attorney, and financial strategist Mark J. Kohler, host of The Main Street Business Podcast. Known for helping entrepreneurs and families navigate tax, legal, and wealth-building strategies, Mark breaks down actionable tips like leveraging S Corporations, family board meetings, and Roth IRAs for kids, while sharing his expertise on year-end tax moves and financial planning essentials.
Together, Josh and Mark dig into why S Corporations can be a game-changer for cutting self-employment taxes, how to turn family board meetings into tax deductions, and ways to use Roth IRAs for your kids to save now and build their financial future. The two also cover year-end moves like buying vehicles or equipment for bonus depreciation, leveraging HSAs for tax benefits, and making sense of crypto taxation as it continues to evolve.
Check out more from Mark Kohler on his website and his educational platform for small business owners.
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Ep 45 - Surviving Inflation and Competition as a Small Business Owner
What does it take to build and sustain a thriving small business in today’s economy? Josh breaks down the challenges small business owners face, from inflation and competition to tax strategies and cash flow management. Drawing from his own experience as a young entrepreneur, he lays out actionable steps to create a strong financial foundation for your business and navigate the complexities of running a company in a competitive market.
Then in 'Extra Points,' the conversation turns to Starbucks and its recent struggles in maintaining its foothold as a giant in the coffee world. Josh and the team examine what’s going wrong for the company and what small businesses can learn from their missteps.
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How Popular Gurus Are Failing Investors w/ David McKnight
What’s the real cost of following mainstream financial gurus? Josh brings back bestselling author David McKnight to unpack his latest book, The Guru Gap: How America’s Financial Gurus Are Leading You Astray, and How to Get Back on Track. They dissect "advice" from popular figures like Dave Ramsey and Suze Orman, highlighting why their broad strategies might not work for everyone—and what you can do instead.
Josh and David dig into nuanced financial strategies, including Roth conversions, annuities, and life insurance, explaining how these tools can help mitigate longevity risk and take advantage of current tax laws. They also discuss how Trump-era tax cuts impact Roth planning and why personalized advice beats generic rules of thumb every time. Plus, the two bond over the joys and challenges of raising seven kids each.
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