Redefine Retirement with Ryan Wheless

Allied Wealth

The official Redefine Retirement podcast with Ryan Wheless. Hosted by Ryan Wheless, Founder of Allied Wealth, this show brings you conversations with the top minds in finance, healthcare, estate planning, and lifestyle design. From Social Security and smart investing to legacy planning and inflation protection, we cover the critical topics that shape a lasting retirement.

  1. 2D AGO

    Inside Legit Real Estate Business & Building a Passive Income Portfolio That Replaces Your Salary (w/ Eric Hughes)

    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, pivoting into corporate jet flying, then using a real estate license and mortgage company to fund his first investments before selling his entire portfolio in 2007 just ahead of the crash. The conversation dives deep into the mechanics of cash flow investing, including how to evaluate markets using cap rates and cash on cash returns, why lower priced markets like Memphis and Birmingham consistently outperform high cost coastal cities for yield, and why the 1% rent to purchase price rule matters when screening deals. Ryan and Eric explore the remote investing model and the critical role professional property management plays in making rental income truly passive, covering everything from tenant screening and eviction processes to maintenance systems and how to avoid being personally involved in day to day operations. They break down the full financial picture of rental property ownership including the powerful tax advantages of depreciation and how it can dramatically reduce the effective tax rate on rental income compared to W-2 earnings. The episode also covers how much capital someone needs to get started, why owning at least three to five properties helps smooth out the volatility of direct ownership, how to use equity from existing properties through cash out refinancing and HELOCs to fund future acquisitions, and why current interest rates — while higher than recent historic lows — still make leveraged real estate investing a compelling long term wealth building strategy. Eric closes by walking through exactly what his one on one coaching program looks like and how listeners can access his free resources and Rental Property Analyzer at rentalincomeadvisors.com. Subscribe to our YouTube Channel: ⁠⁠https://www.youtube.com/@alliedwealth Follow Allied Wealth on Instagram: https://www.instagram.com/allied_wealth/?hl=en Visit the Allied Wealth website to learn more: https://alliedwealth.com/ PRODUCED BY IRONCLAD

    59 min

  2. MAY 12

    How Two Average Incomes Built Enough to Retire Early and Travel the World - Robert & Jill’s Story

    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 TSA, which combined with his military time allowed him to retire at 60 with a federal pension. Jill spent 25 years in corporate marketing before pivoting after Covid to open a strength training studio for adults 45 and over before retiring from that as well. The couple shares how the idea was sparked by a river cruise invitation that felt too expensive, which led them to discover that long term international travel could actually cost less than maintaining their lifestyle in Palm Springs. They walk through the practical financial steps they took — working with a financial planner, mapping out their TSP and 401K savings, deciding to sell rather than rent their home and preserving a portion of the home sale proceeds as a contingency fund. Ryan and his guests dive deep into the importance of couples getting financially aligned, automating savings, avoiding lifestyle inflation and the liberating feeling of owning less. Robert and Jill also share their travel hacking strategies including booking long haul travel a year or more in advance, stacking travel credit card points and using the Trusted House Sitters platform to eliminate their biggest expense housing for hundreds of nights a year. The episode closes with a powerful message for anyone who feels stuck that financial freedom is more accessible than most people think, and that the first step is simply deciding what you want your life to look like and then working backwards to build a plan to get there. Subscribe to Robert & Jill’s YouTube Channel: https://www.youtube.com/@OurRetirementReinvented Subscribe to our YouTube Channel: ⁠⁠https://www.youtube.com/@alliedwealth Follow Allied Wealth on Instagram: https://www.instagram.com/allied_wealth/?hl=en Visit the Allied Wealth website to learn more: https://alliedwealth.com/ PRODUCED BY IRONCLAD

    44 min

  3. MAY 5

    Why 80% of Women Fire Their Financial Advisor After Their Husband Dies with Dr. Barb Provost

    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 husbands pass away. Barb breaks down the systemic financial disadvantages women face from the start, including the gender pay gap where women earn just $0.82 on the dollar, the pink tax that makes everyday products and services more expensive for women, and the career interruptions that come from caregiving and raising children. She explains why women are positioned to control an unprecedented share of American wealth over the next several years as the baby boomer generation ages and men statistically die first, with the average age of widowhood being just 59. The conversation gets deeply practical as Barb outlines what women actually want and need from a financial advisor — primarily to be heard, respected and included in the conversation rather than dismissed or talked over. Ryan shares several compelling real-life stories from his own practice including a widow who nearly drained her IRA to give her son $450,000 for a house, illustrating why having a trusted advisor who knows your values is so critical in vulnerable moments. Barb also reveals the alarming statistic that 70 to 80 percent of women leave their financial advisor within the first year of losing a spouse, and explains exactly why that happens and how advisors can prevent it. The episode closes with both Ryan and Barb emphasizing that women must get involved in their family finances now — not after a crisis — because the plan should already be in place long before it is ever needed. Subscribe to Dr. Barb’s YouTube Channel: https://www.youtube.com/@pursestringsco/featured Subscribe to our YouTube Channel: ⁠⁠https://www.youtube.com/@alliedwealth Follow Allied Wealth on Instagram: https://www.instagram.com/allied_wealth/?hl=en Visit the Allied Wealth website to learn more: https://alliedwealth.com/ PRODUCED BY IRONCLAD

    41 min

  4. APR 28

    The Couple Who Retired at 40 With No House, No Car, and No Regrets (w/ the Donegans)

    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 money to buy freedom rather than simply saving for future spending. They walk through their personal journey of aggressively cutting lifestyle inflation, downgrading cars, living in a small flat, and channeling the gap between income and expenses into global index funds until they hit their target number of 25 times their annual spending — a concept rooted in the 4% rule. Katie opens up about the guilt she initially felt about retiring so young while peers were still working, and how discovering the FIRE movement helped shift her mindset entirely. Ryan adds his own relatable story of selling off a lake house, boat, jet skis, and airplane to escape the stress of looking wealthy on paper while having little real financial security. The conversation also covers practical tools like monthly finance meetings, automating savings into hard-to-access accounts, the importance of not locking all your money in a 401K if you want to retire early, and riding out market downturns without panic selling. The episode wraps up with the Donegans sharing that since retiring, their invested wealth has grown from £1 million to £2.5 million, and that in 2024 they were awarded the British Empire Medal for their services to financial education through their completely free online course. Subscribe to Katie and Alan’s YouTube Channel: https://www.youtube.com/@rebeldonegans Subscribe to our YouTube Channel: ⁠⁠https://www.youtube.com/@alliedwealth Follow Allied Wealth on Instagram: https://www.instagram.com/allied_wealth/?hl=en Visit the Allied Wealth website to learn more: https://alliedwealth.com/ PRODUCED BY IRONCLAD

    56 min

  5. APR 21

    Broke 3 Months Into Marriage With $20 in the Bank – How We Retired Debt-Free on Below-Average Income

    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 housing, food, clothing, and transportation, cutting overspending (such as high rent and eating out), and adopting consistent habits like paying themselves first, automating savings, and working as a unified team with weekly accountability meetings. Through frugality, gamifying goals, using their "P.I.E." method (Plan, Implement, Evaluate) in 30-day challenges, avoiding debt, buying cheap reliable cars, and paying cash for homes and vehicles, they raised four boys debt-free, built wealth patiently, maxed out Roth IRAs, and eventually paid cash for their current home—all while refusing to say they were "stuck" and budgeting for fun through low-cost activities like walks and camping. Now semi-retired with a successful YouTube channel ("Under the Median") sharing frugal living tips, they emphasize that frugality isn't deprivation but reallocating money from less important areas to what truly matters, proving that small, consistent savings over time, combined with purpose-driven goals and a strong partnership, can lead to a joyful, abundant, debt-free retirement even on below-median income. The discussion also covers practical retirement math, the power of automation, engaging a financial planner early, and the importance of knowing your personal savings rate. Subscribe to our YouTube Channel: ⁠⁠https://www.youtube.com/@alliedwealth Follow Allied Wealth on Instagram: https://www.instagram.com/allied_wealth/?hl=en Visit the Allied Wealth website to learn more: https://alliedwealth.com/ PRODUCED BY IRONCLAD

    45 min

  6. APR 14

    Why Delaying Social Security Could Be Worth Hundreds of Thousands of Dollars (w/ Teresa Ghilarducci)

    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-yourself 401(k) system has failed the average worker — with most people entering retirement with a fraction of what they were supposed to have saved. The conversation digs into the dangers of financial plans built on overly optimistic market return assumptions, the psychological and physical toll of financial insecurity in old age, and why the idea of simply "working longer" is an unrealistic solution for most Americans given rampant age discrimination and involuntary job loss. Ryan and Teresa explore potential solutions, including the strategic use of annuities, the critical importance of delaying Social Security claims to maximize lifetime income, and a proposed Congressional bill that could help Americans access more fairly priced group annuities. Ryan also shares how his firm, Allied Wealth, approaches retirement planning by prioritizing predictable, guaranteed income streams over net worth accumulation, helping clients build financial stability that doesn't rise and fall with the stock market. The episode wraps with a discussion of Teresa's book "Work, Retire, Repeat," which challenges the narrative that working until you drop is either a realistic or dignified retirement strategy for most Americans. Visit Teresa’s website at: https://www.teresaghilarducci.org/ Subscribe to our YouTube Channel: ⁠⁠https://www.youtube.com/@alliedwealth Follow Allied Wealth on Instagram: https://www.instagram.com/allied_wealth/?hl=en Visit the Allied Wealth website to learn more: https://alliedwealth.com/ PRODUCED BY IRONCLAD

    29 min

  7. APR 7

    Tom Hegna: Put 20-40% of Portfolio Should Be in This or Risk Running Out of Money

    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% of the portfolio, supplemented by Social Security or pensions), rather than risking one's entire nest egg in the stock market where volatility can threaten daily lifestyle needs—much like how a working paycheck remained stable regardless of market swings. The conversation highlights how guaranteed income provides psychological confidence to spend freely on both necessities and enjoyments like travel or golf, combats sequence of returns risk, improves overall portfolio performance by allowing riskier growth assets to remain untouched during downturns, boosts happiness, and may even extend longevity by reducing stress. They explore the role of AI in enhancing (but not replacing) advisors, caution against chasing annuity "bonuses" or exotic indexes without understanding trade-offs like lower caps or longer surrender periods, and stress the value of personalized advice in navigating complex factors such as taxes, long-term care, IRMAA, and inflation. Tom shares his own strategy of building multiple streams of guaranteed income while maintaining growth investments, backed by research from sources like BlackRock and the Wall Street Journal showing the benefits of combining annuities with an optimized portfolio. Overall, the episode promotes following math and science over chasing returns, creating a "license to spend" for a more fulfilling and worry-free retirement. Visit Tom’s website at: https://tomhegna.com/ Subscribe to our YouTube Channel: ⁠⁠https://www.youtube.com/@alliedwealth Follow Allied Wealth on Instagram: https://www.instagram.com/allied_wealth/?hl=en Visit the Allied Wealth website to learn more: https://alliedwealth.com/ PRODUCED BY IRONCLAD

    31 min

  8. MAR 31

    Couple Plans to Move to Florida With $3M – But Their Advisor Revealed This Terrifying Truth

    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 taxes, and handle healthcare before Medicare. After building a detailed financial blueprint that included their asset breakdown (IRAs, 401(k), cash, life insurance, and a $1M primary home with a small mortgage), the team addressed downsizing and relocating to the Gulf Coast, bridged the healthcare gap until Medicare eligibility, incorporated $11,000 monthly after-tax expenses (growing at 3%), potential long-term care needs, and $20,000 annual travel goals during their “go-go” retirement years. The host emphasized shifting focus from average returns (their current portfolio at 7.6%) to risk via standard deviation (12.5%), illustrating how the portfolio could gain up to 20.1% in strong markets but lose nearly 30% in severe downturns—potentially devastating for the couple. By reallocating to reduce risk and slightly improve returns, the plan’s long-term success probability rose from a marginal 72% to a more comfortable 85%, allowing the couple to enjoy their retirement with confidence rather than fear of running out of money. The episode highlights how Allied Wealth’s planning process empowers clients to make informed decisions for a limitless retirement. Subscribe to our YouTube Channel: ⁠⁠https://www.youtube.com/@alliedwealth Follow Allied Wealth on Instagram: https://www.instagram.com/allied_wealth/?hl=en Visit the Allied Wealth website to learn more: https://alliedwealth.com/ PRODUCED BY IRONCLAD

    15 min
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2 Ratings

About

The official Redefine Retirement podcast with Ryan Wheless. Hosted by Ryan Wheless, Founder of Allied Wealth, this show brings you conversations with the top minds in finance, healthcare, estate planning, and lifestyle design. From Social Security and smart investing to legacy planning and inflation protection, we cover the critical topics that shape a lasting retirement.

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