Redefine Retirement with Ryan Wheless

In this episode of Redefine Retirement, host Ryan Wheless sits down with Doug Nordman, author of The Military Guide to Financial Independence and Retirement , to share how military members can achieve lasting financial independence by leveraging their unique benefits, maintaining a high savings rate, and building the resilience to weather any market storm. Purchase Doug Nordman’s latest book: http...

On this episode of Redefine Retirement, Ryan sits down with Jeremy Keil, known online as "Mr. Retirement," to break down his five step process for turning retirement savings into lasting income. They dig into the biggest mistakes people make with their 401(k)s, why Roth conversions should be spread over multiple years rather than done all at once, and how the often misunderstood 4% rule...

In this episode of Redefine Retirement, host Ryan Wheless sits down with Fritz Gilbert early retiree, FIRE movement advocate, and founder of The Retirement Manifesto blog to explore what it truly takes to build a fulfilling retirement that goes far beyond the numbers. Fritz shares his personal journey of retiring at 55, the emotional and psychological challenges he did not anticipate, and his fram...

In this episode of Redefine Retirement, host Ryan Wheless walks through a real-world retirement planning case study for a couple, who have $1.8 million saved and want to retire at ages 60 and 61 while spending $8,000 a month plus $10,000 a year on travel. Rather than starting with the numbers, Ryan emphasizes that a fulfilling retirement begins with defining how you want to spend your time, who yo...

In this episode of Redefine Retirement, host Ryan Wheless sits down with Kristy and Bryce — the husband and wife team behind Millennial Revolution and the book Quit Like a Millionaire — for one of the most genuinely eye opening conversations the show has produced on what financial independence actually looks like when you pursue it with intention and without following the conventional script. Kris...

In this episode of Redefine Retirement, host Ryan Wheless sits down with Laura Phillips, a licensed reverse mortgage specialist with over 25 years of experience in real estate lending across Colorado, for a conversation that dismantles virtually every negative assumption most people carry about reverse mortgages. Laura starts by breaking down the basics — a reverse mortgage is simply a financial t...

In this episode of Redefine Retirement, host Ryan Wheless sits down with Eric Hughes, founder of Rental Income Advisors, who left his corporate career at 39 by building a portfolio of cash-flowing rental properties and now coaches others to do the same. Ryan walks through his own unconventional path into real estate — starting as a flight instructor after 9/11 disrupted the aviation industry, pivo...

In this episode of Redefine Retirement, host Ryan Wheless sits down with Robert and Jill, the couple behind the YouTube channel Retirement Reinvented, who made the bold decision to sell their home, two cars and virtually everything they owned to travel the world full time in retirement. Robert brings a background of military service including a year in Baghdad, followed by nearly 18 years with the...

In this episode of Redefine Retirement, host Ryan Wheless sits down with Dr. Barb Provost, founder of Purse Strings, for a candid and eye-opening conversation about women and wealth. Ryan opens by sharing how he personally sought out Barb's expertise because he witnesses firsthand — after more than 20 years in the financial advisory business — how often women are left unprepared when their hus...

In this episode of the Redefine Retirement podcast, host Ryan Wheless sits down with British couple Alan and Katie Donegan, founders of Rebel Finance School, who achieved financial independence in their early 40s and retired in 2019. The Donegans break down their straightforward approach to building wealth, centered around what they call the "freedom rate" — the idea of investing your mo...

In this episode of Redefine Retirement, host Ryan Wheless interviews Hope and Larry, a couple who transformed their financial future after discovering they were flat broke just three months into marriage, with only $20 left until the next paycheck. Starting on modest incomes (around minimum wage), they took charge by tracking every expense, creating a bare-bones budget focused on essentials like h...

In this episode of Redefine Retirement, host Ryan Wheless sits down with renowned labor economist and retirement security expert Teresa Ghilarducci to discuss the alarming state of retirement in America today. Teresa paints a sobering picture of how today's retirees are actually worse off than their parents and grandparents, largely because the shift from traditional pensions to the do-it-your...

In this episode of Redefine Retirement, host Ryan Wheless welcomes back retirement expert Tom Hegna to discuss a smarter, more secure approach to retirement planning that contrasts sharply with traditional Wall Street strategies. They emphasize the importance of first securing a reliable "paycheck" in retirement through guaranteed lifetime income products like annuities (ideally 20-40% o...

In this episode of Redefine Retirement hosted by Ryan Wheless powered by Allied Wealth, the discussion focuses on a real client case study of a couple (ages 60 and 57) with approximately $3.143 million in net worth who approached the team with common retirement concerns: whether they had saved enough, could afford to retire, travel extensively, move to Florida, optimize Social Security, manage tax...

In this episode of Redefine Retirement, host Ryan Wheless shares his personal journey from a troubled youth to discovering purpose through aviation, navigating industry crashes post-9/11 and the 2008 financial crisis, and ultimately founding his wealth management firm to guide clients toward financial security and fulfillment. Joined by happiness strategist Monique Rhodes, the conversation shifts...

In this episode of Redefine Retirement hosted by Ryan Wheless of Allied Wealth, guest Rob Slovak, an attorney specializing in complex business divorces, joins to discuss protecting business partnerships—especially relevant for retirement planning when exiting or transitioning ownership. The conversation emphasizes that many partnerships begin with good intentions but loose documentation, leading t...

In this episode of the Redefine Retirement podcast, hosted by Ryan Wheless and featuring guest Anqi (Angie) Chen, Associate Director of Savings and Household Finance at Boston College's Center for Retirement Research, the discussion centers on America's ongoing retirement preparedness challenges. Chen explains the National Retirement Risk Index (NRRI), which, based on the latest 2022 data...

In this eye-opening episode of Redefine Retirement, host Ryan Wheless sits down with Dan Buettner Jr., Executive Vice President and Chief Development Officer at Blue Zones, to unpack the science of longevity and what it really takes to thrive—not just survive—in retirement. Drawing from decades of global research identifying the "Power 9" habits of the world's longest-living people,...

In this episode of Redefine Retirement, host Ryan Wheless sits down with Dr. Richard P. Himmer, a longtime financial professional and author of Your Encore Years: The Psychology of Retirement , to explore the often-overlooked emotional and psychological dimensions of retirement planning. Himmer argues that true wealth isn’t just about dollars—it’s about having “enough” in relationships, purpose, i...

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, o...

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 al...

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, historica...

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...

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 reti...

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 avera...