In this episode of Redefine Retirement, host Ryan Wheless powered by Allied Wealth, Ryan explores a major 2025 regulatory change that has opened access to the previously exclusive world of private equity and private credit for everyday investors. He explains how these private markets - historically dominated by the ultra-wealthy - have outperformed the S&P 500 by over 5% annually since 1988, offering higher returns with significantly lower volatility due to less frequent repricing, active operational improvements by funds, and a focus on middle-market companies. Using examples like private equity roll-ups of veterinary practices and private credit lending to fill the void left by tightened bank regulations post-2008, Ryan highlights perpetual fund structures that provide ongoing income (e.g., 9-10% yields), partial liquidity, and lower entry points. He stresses the potential for a balanced portfolio (e.g., one-third public markets, one-third private markets, one-third non-market assets) to reduce risk more effectively than chasing higher returns alone, urging listeners to discuss these opportunities with their advisors as they could help solve America's retirement crisis.

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In this episode of Redefine Retirement, host Ryan Wheless interviews Ashton Applewhite, a leading anti-ageism advocate and author of This Chair Rocks: A Manifesto Against Ageism. Applewhite defines ageism as prejudice or discrimination based on age—often assuming someone is "too old" or "too young" for tasks, roles, or relationships—and stresses that it affects people across all life stages, not just older adults. She explains how internalized ageism (self-limiting beliefs like "I'm too old for that") stems from a youth-obsessed culture that profits from fear of aging, while also perpetuating ableism and gender biases. Challenging stereotypes, she highlights the diversity of aging experiences—older people become more varied, not uniform—and argues for reframing aging as a natural, multifaceted journey with real benefits like wisdom and resilience, rather than inevitable decline. The discussion ties directly to retirement, exploring workplace discrimination, identity shifts post-career, fears of becoming a "burden," the value of interdependence over rigid self-reliance, and the need for inclusive narratives that portray vibrant, purposeful later life—ultimately empowering listeners to reject ageist tropes and embrace aging with curiosity and agency.

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The "best of" episode of the Redefine Retirement podcast, hosted by Ryan Wheless, features insights from prominent guests Ed Slott (IRA/tax expert), Karsten Jeske (early retirement blogger known as Big Ern), and Mark Henry (financial advisor and Alloy Wealth founder). The discussion centers on the looming "retirement savings time bomb" driven by massive national debt, historically low tax rates that are unlikely to stay that way, and trillions in tax-deferred accounts (like IRAs and 401(k)s) that the government will eventually tax heavily. Ed Slott stresses converting to Roth IRAs now to lock in current low rates as "tax insurance," even if rates don't rise immediately, while explaining Roth rules (including the five-year holding periods, penalty-free access to contributions, and why conversions are best for long-term, post-59½ use). Karsten Jeske highlights the U.S.'s relatively favorable tax environment compared to places like Germany, advising balanced Roth conversions to avoid overdoing it and waste low-bracket opportunities, while aiming to equalize marginal rates throughout retirement, fill lower brackets strategically (e.g., pre-Social Security), and manage RMDs to prevent bracket creep or excess distributions. Mark Henry emphasizes the critical need for a guaranteed, written income plan that accounts for inflation, market volatility, widowhood challenges (like the "widow's tax" from lost spousal income, higher household costs, and unexpected expenses), gray divorce risks, and ensuring both spouses understand the plan to avoid leaving a surviving partner unprepared. Overall, the episode urges proactive tax optimization, Roth strategies, and holistic planning beyond mere asset allocation to achieve a confident, abundant retirement free from uncertainty.

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In this episode of Redefine Retirement, host Ryan Wheless welcomes Jean Chatzky, CEO of HerMoney and bestselling author, to discuss the massive intergenerational wealth transfer underway in America, where women—due to longer lifespans—are poised to control the majority of household wealth in the coming years. They explore the key differences in how women approach money compared to men, with women prioritizing safety and security, often holding too much cash and entering investments later, yet frequently outperforming men through disciplined buy-and-hold strategies. The conversation delves into systemic challenges like the gender pay gap and “pink tax,” the tax pitfalls widows face, the critical need for both spouses to be actively involved in financial planning, and practical advice for women of all ages—from automatic saving habits for younger generations to building a secure “forever paycheck” in retirement through guaranteed income sources. Ultimately, Jean empowers women to overcome hesitation, ask questions, and take control of their financial futures with confidence and simplicity.

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In this episode of the Redefine Retirement podcast, host Ryan Wheless welcomes renowned behavioral economist Dan Ariely to explore why humans are predictably irrational when it comes to money and retirement planning. Ariely explains that our brains evolved for short-term survival, not long-term investing or understanding compound interest, leading most people to delay saving and underestimate retirement needs—often aiming for just 70% of pre-retirement income when ideal lifestyles actually require 140% or more. He highlights how modern temptations and lack of immediate rewards make saving feel invisible and unrewarding, while spending gets instant gratification, and stresses the importance of starting early, reviewing past spending for regrets, and adding personal/family rewards to make delayed gratification motivating. The conversation also touches on the psychological challenges of retirement—losing purpose, identity tied to work, and social networks—urging listeners to prepare 2–3 years in advance with new hobbies, friends, and part-time pursuits to avoid isolation and maintain mental sharpness in a longer lifespan.

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In this episode of the Redefine Retirement podcast, host Ryan Wheless welcomes wealth strategist and tax attorney Rebecca Walser to challenge conventional retirement planning wisdom. Walser argues that the 401(k), originally designed in the late 1970s as an executive retention tool amid 70% tax rates, became America's default retirement vehicle by accident—never mathematically tested for average workers—and has contributed to a massive $17–$25 trillion savings gap and impending tax crisis as baby boomers retire. With current rates historically low and future middle-class taxes potentially soaring to the mid-60s per CBO projections, she warns against over-relying on pre-tax accounts and urges shifting to Roth options, mega backdoor strategies, and "buyout" plans while rates are favorable. The discussion also covers rising market volatility fueled by retail 401(k) inflows and AI-driven concentration, emphasizing the need to pair risk-on growth investments with risk-off protection to survive inevitable downturns without derailing retirement lifestyles.

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In this episode of the Redefine Retirement podcast, host Ryan Wheless CEO of Allied Wealth takes a straightforward Q&A approach to address the most frequent questions potential and current clients ask via social media, YouTube, and direct outreach. He breaks down the firm's fee structure (typically 0.75%–2%, averaging 1.25%), emphasizing that fees must deliver clear value through tax planning, risk reduction, and enhanced returns across public, private equity/credit, and non-market investments. Wheless explains why "Are you a fiduciary?" is an outdated question in today's independent advisory landscape, stresses that no client gets "passed off" regardless of asset level, and details the comprehensive wealth management services—including investment consulting, advanced tax/estate planning, wealth transfer/protection, and relationship management with CPAs and attorneys—that set Allied Wealth apart from traditional broker-dealers. The episode wraps with an open invitation for listeners to submit more questions and reach out for personalized guidance.

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In this episode of the Redefine Retirement podcast, host Ryan Wheless engages in a wide-ranging conversation with Jamie Hopkins, a highly credentialed retirement planning expert (attorney, CFP, MBA, RICP co-creator, and more) who now leads a major trust company managing $93 billion in assets under administration. Hopkins discusses his background in retirement income education, including his role in developing the RICP designation focused on distribution strategies, annuities, long-term care, and tax planning, as well as his current work providing corporate trustee services (primarily via Delaware and Nevada trusts) for high-net-worth clients, law firms, and RIAs. The duo touches on family life and travel with young children, then shifts to post-election tax landscape—highlighting the likely extension of TCJA provisions, small business benefits, and ongoing concerns like Social Security solvency and national debt. Hopkins promotes his new visually oriented book Your Retirement Sketchbook, critiques over-reliance on Monte Carlo success/failure metrics in favor of adaptive “guardrails” planning, endorses annuities for liability-matched essential income flooring, and advocates rising equity glide paths plus private market diversification for smoother volatility in retirement portfolios. The episode wraps with praise for evolving private equity access and a call for more dynamic, client-centered retirement conversations.

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In this engaging episode of the Redefine Retirement podcast, host Ryan Wheless sits down with Annie Duke, a former world-champion poker player turned cognitive psychologist, delivering a masterclass on why even the most well-intentioned investors repeatedly sabotage their own retirement plans. The core problem is that our brains treat “future us” like a stranger, so in moments of panic (a 30% market drop, a scary headline), the present-self hijacks the wheel and wrecks decades of planning. Her solution is to do the hard work while everyone is calm: guide clients through vivid pre-mortem and pre-parade exercises (“Imagine it’s a year from now and you’re broke—why?” / “Imagine you crushed it while your friends panicked—why?”), let the clients generate their own answers and pre-commitments (so they actually own the plan), and reframe disciplined behavior as a rare, elite identity (“You’re one of the few who doesn’t sell at the bottom”). The result is far fewer emotional blow-ups, far less panic-selling at market lows, and retirees who actually get to live the life they spent decades saving for instead of watching it evaporate because they couldn’t resist checking the ticker on a bad day.

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In this engaging episode of the Redefine Retirement podcast, host Ryan Wheless sits down with retirement policy expert and former Social Security deputy commissioner Jason Fichtner to tackle the biggest retirement fears head-on: running out of money and making the wrong Social Security decision. They dismantle the outdated “breakeven analysis” that pushes most people to claim benefits at 62, showing how delaying to 70 (especially when one spouse is younger) maximizes lifetime income, survivor benefits, and inflation-protected payments — while humorously noting that the real way to “stick it to the government” is to live long and collect bigger checks. The conversation shifts to replacing vanished pensions in today’s 401(k) world, with both strongly advocating protected lifetime income through annuities as an essential “tool in the toolbox” (not a four-letter word), using bridge strategies, bucketing, and a simple 50/30/20 allocation (equities/bonds/guaranteed income) to cover essentials no matter what markets, inflation, or sequence-of-returns risk throw at you. They address Social Security’s 2033–34 trust-fund depletion (yes, benefits will still be there, likely with a gradual ~20% reduction), offer a clever deferred-annuity “insurance policy” against cuts, and highlight behavioral insights — people with guaranteed income sleep through crashes, spend more confidently in retirement, and avoid panic-selling at market bottoms. Packed with actionable reframes, myth-busting, and real hope, it’s a masterclass in building a paycheck-for-life that lets retirees actually enjoy the retirement they worked decades to earn.

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