Welcome to the Early Retirement Roadmap podcast, your audio guide to preparing for and thriving in early retirement! If you’re dreaming of retiring early but feeling overwhelmed about where to start, or if you’re already retired and looking to make the most of your freedom, you’re in the right place. I’m your host Mike Upland, and I successfully retired at 55. Through this podcast, I share my personal early retirement journey—the victories, the challenges, and all the essential lessons I’ve ...
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Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)
Ari Taublieb, CFP®, MBA
Ari Taublieb is a CERTIFIED FINANCIAL PLANNER™ and Vice President of Root Financial Partners. Ari Taublieb, CFP®, MBA specializes in helping people navigate an early retirement. I get it...retirement sounds overwhelming (an early retirement may sound particularly overwhelming)! Does it just feel like there's so much to consider and you just want to make sure you're doing everything you can to set yourself up right? If I may ask...why do YOU want to retire early? Do you want to travel? Have y ...
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This show is created for anybody interested in being financially free and understanding the benefits of generating passive income through long-term investing. The common goal is to reach your time-freedom point (ASAP) and no longer have to exchange time for money. If you find yourself craving early retirement, seeking answers, struggling to take that first step, or just look for new information, you need to tune in! Join Axel and special guests as they discuss many different success strategi ...
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Life after college graduation is never easy, especially when you're broke. As I go through my journey, I'm bringing some of the dopest creatives in the New York City with me. Join us as we drop knowledge on how to barely survive...and if this all goes according to plan, we'll all be set for Early Retirement.
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On Apartment Investing For Early Retirement, we sit down with accomplished investors, leaders, and industry experts in the world of multifamily real estate. We discuss how to capitalize on the vast opportunity that apartment investing presents to build wealth and help you achieve your financial goals.
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Ep 479- Does Mentorship matter in Investing?
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6:12In this episode, Axel discusses the missed opportunities he had and now shares how you can take advantage of experts in your chosen field of investing, or even in life. Enjoy! Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com/iwg-strategy BOOK IS OUT! Grab Your Copy and learn how to get your …
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How Much Do You REALLY Need to Retire on $10K a Month?
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16:28Want to retire on $10K a month? This episode shows exactly how much you need saved in 2025 and beyond—factoring in taxes, healthcare, inflation, Social Security, and investment risk. We’ll break down what it really takes to sustain $10,000 in monthly retirement income spending —whether you're aiming for early retirement, following the 4% rule (and …
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How To Pay 0% Taxes On $120k+ Of Retirement Income
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15:46Tax gain harvesting is one of the most underused but powerful strategies available to early retirees and those pursuing financial independence. In this episode, we explore how it works, who it's best suited for, and how it can help reduce long-term tax liability. Unlike tax loss harvesting, which involves selling investments at a loss to offset gai…
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High-margin, Low-complexity Businesses | Franchise Expert
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30:08Cliff Nonnenmacher has owned and operated various franchise businesses, including Cartridge World, Personal Training Institute, PuroClean, and Maid Right, as well as non-franchise companies. He has also developed well-known domestic and international brands like Four Seasons Sunrooms, Contours Express, Island Fin Poke, and Krak Boba. [00:00-05:09] …
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In this episode, Axel talks about an investment opportunity that isn't familiar to many. Enjoy Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com/iwg-strategy BOOK IS OUT! Grab Your Copy and learn how to get your feet wet in real estate investing…
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Ep 476 - How to Invest with High Mortgage Interest Rates?
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7:59In this episode, let's discuss seizing the opportunity with high mortgage interest rates. Let's invest IDEALLY - enjoy! *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https:…
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This Is What Financial Planning Really Changes
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18:25What does it really mean to change someone’s life through financial advice? While we’re not saving lives like doctors, the impact we have on our clients’ futures can be just as meaningful. Often, it’s not about the numbers—it’s about helping someone move forward when fear is holding them back. We’ve seen it firsthand. Like the dentist who had every…
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SHOULD WE BE THE BANK rather than a landlord? | Notes investing vs Real estate investing
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36:49We interviewed Eddie Speed, America's most experienced note buyer and owner of Colonial Funding Group LLC. He brings over four decades of expertise and 50,000+ closed note deals to Deal-Maker Richmond. As a pioneering force in the note buying industry, Eddie specializes in helping real estate investors and property owners unlock hidden value in the…
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Will ACA Subsidies Disappear After 2025? What You NEED to Know!
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6:00⚠️ Are ACA subsidies really going away after 2025? If you're planning to retire early or already living off your investments, this could impact your healthcare costs in a big way. In this episode, I explain exactly what's happening with ACA subsidies in 2026—what's expiring, what's staying, and how you can still qualify for financial help through s…
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Ep 474-Investment Properties IDEAL for Remote Work
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7:38After Covid, #remotework has been the ideal work situation. Implementing this to long-term investing, in this episode, let's talk about investment properties best suited for remote work buyers *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** G…
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Why $1.5M Is Enough To Retire If You Want To Spend Like This
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15:21You don’t need $2 to $3 million to retire unless your lifestyle truly requires it. In this episode, we break down why your retirement number should be built around your personal spending needs, not a one-size-fits-all benchmark. With a well-diversified $1.5 million portfolio, many retirees can support $60,000 to $75,000 per year in spending, especi…
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Episode 473 - Pacasco luxury vacation home fractional ownership
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7:56DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com/iwg-strategy BOOK IS OUT! Grab Your Copy and learn how to get your feet wet in real estate investing…
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If You’re in Your 40s, 50s, or 60s: 25 Life Lessons from 70+ Year-Olds
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11:50If you're in your 40s, 50s, or 60s, listen to this! In this podcast, I share 25 life lessons from people over 70 — timeless wisdom for navigating midlife, retirement planning, relationships, purpose, and happiness. These life lessons are based on the powerful research of Dr. Karl Pillemer, author of 30 Lessons for Living, who interviewed over 1,000…
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How Your Kids Can Derail Your Retirement (Unless You Plan for It)
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7:37Many early retirees forget to factor in their adult children when planning retirement. From weddings and tuition to ongoing support, the financial impact can be substantial—especially when you no longer have a paycheck coming in. In this episode, I’ll walk you through how to plan for potential financial support, set healthy boundaries, and protect …
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Explore Tokenized Real Estate with CEO of REtokens | Real estate expert
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36:46Tyler Vinson is pioneering the future of real estate investing. As the CEO of REtokens, the platform is already recognized as one of Proptech Outlook’s Top 10 Commercial Real Estate Solutions Providers for 2024. *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal *…
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Episode 471 - Understanding Property tax Assessment and Appeals process
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8:21DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com/iwg-strategy BOOK IS OUT! Grab Your Copy and learn how to get your feet wet in real estate investing…
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5 Expenses To Cut to Reach Financial Independence (and 3 NOT to)
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21:03Retiring early doesn’t mean cutting out everything you love, it means being intentional about what truly adds value to your life. In this episode of Root Talks, we take a closer look at the spending choices that can either delay or accelerate your path to early retirement. We explore which tradeoffs are worth making, where small changes can have a …
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Episode 470- Relationship between employment ratres and housing demand
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7:47In this episode, Axel will summarize how you can take advantage of employment rates when looking at investment properties. *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at htt…
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Ready to Retire? Here's How to Tell Your Company │ Root Talks
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24:32In this episode, Ari and James explore the emotional and practical sides of retiring—specifically, how to have the conversation that officially ends your career. Whether you're months away or years out, this discussion tackles the fear, hesitation, and freedom that come with telling your boss you're done. You'll hear real stories from Root Collecti…
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How Jeff Made 7 Figure Exits in just 7 years | Shortcuts to Financial Freedom
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37:38In this episode, it was an honor to interview Jeff Kikel is an Entrepreneur, Author, and Podcaster. Starting off as a shy introvert, Jeff went on to become a successful financial advisor. After 20 years and 7 failed attempts at starting side hustles, Jeff left the corporate world and formed his first two successful businesses in 2015. This led to s…
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Claim Social Security at 62, 67, or 70? The Answer May Surprise You!
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9:45Should you claim Social Security early, wait until full retirement age, or delay until 70? In this podcast, we walk through a real retirement case study and run the numbers to show how your claiming age affects your investments, taxes, and even your health insurance premiums. 📊 See why delaying may not always be the best choice—and how opportunity …
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Episode 468 - How Inflation affects Real Estate Investments
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8:47In this episode, let's use this strategy of using inflation for investing. *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com/iwg-strategy BOOK IS OUT! Grab …
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The 4% Rule: Is It Still the Key to Early Retirement in 2025?
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19:12The 4% withdrawal rule does not apply to early retirees since it's based on a 30-year timeline, not the 40+ years needed for early retirement. Guyton's guardrails approach offers a better alternative, allowing for 5.2-5.6% withdrawal rates by adapting spending based on market performance. • Guardrails approach uses flexible withdrawal rates that in…
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Episode 467 - Impact of Global Events on Local Property Markets
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9:20We talked about neighborhood as a factor when looking for investment properties... what about global events? Find out more on this episode. *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly n…
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How Early Retirees Can Pay WAY Less for Health Insurance!
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12:46Want to pay WAY less for health insurance in early retirement? This follow-up to my previous very popular video (link below in watch next) shows how smart retirees legally slash ACA premiums by strategically managing their income. You'll learn how MAGI impacts subsidies, and see real scenarios using Healthcare.gov. Don’t overpay for healthcare—plan…
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Here's 5 Portfolio Changes To Create More Income In Retirement
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18:38Building a retirement income strategy involves more than selecting dividend-paying stocks. A focus on total return — which includes both growth and income — can offer a more comprehensive approach for long-term planning. • Relying solely on dividend-paying stocks may reduce portfolio diversification and growth potential • Total return (income + gro…
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Episode 466 - Creating a Compelling Property Description
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7:04Want to sell your property faster? In this episode, Axel will share what investors look for... Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com/iwg-strategy BOOK IS OUT! Grab Your Copy and learn how to get your feet wet in real estate investing…
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How to Maximize Your Insurance Claims? From $3K to $600K Claims ff. Andy Gurczak
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28:13A client had his business burn to the ground and was originally quoted $3,000 by his insurance company. With Andy Gurczak's help, he received over $600,000 and was able to properly rebuild and restart his business - enjoy and listen to his strategy. Andy is the Founder of AllCity Adjusting, a licensed public adjusting firm with a focus on making su…
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The Surprising Regrets of Wealthy Retirees | Root Talks
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16:05Retired with millions—but full of regret? In this episode of Root Talks, James and Ari share the real stories no one talks about: wealthy retirees who did everything “right” financially but still feel like they missed out. From sacrificing health and relationships for more savings, to realizing too late that they were planning for someone else’s ve…
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Retirement Stats That’ll Make You Rethink Working Another Year
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7:07Is working longer really worth it? In this episode, I break down 3 retirement stats and insights that could completely change the way you think about work, wealth, and health in retirement. If you're planning for early retirement, these numbers might just shift your whole retirement strategy. Here's what you'll learn: • Why 63.9 years is a critical…
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Why The Biggest Risk To Retiring Early Is Not What You Think
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14:06Even when the financial plan indicates you're on track, many people experience anxiety—especially between ages 50 and 65, before traditional retirement benefits begin. This episode explores ways to prepare for that critical transition with clarity and confidence. • One of the most impactful retirement risks is withdrawing too much from your portfol…
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Episode 463 - Understanding Economic Indicators That Influence Real Estate
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8:32Go back to the basics with this episode! *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com/iwg-strategy BOOK IS OUT! Grab Your Copy and learn how to get you…
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An EASIER Way to Look for Property Investment | Cash Flow Property
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31:37Tapan Trevedi created (and patented) the S.E.C.R.R.E.T.S method to evaluate an address for real estate investors. When applied correctly, a real estate investor can CONFIDENTLY make the decision whether to invest in an address or not - Let's talk about it in this episode! *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free cours…
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Why You’re Closer to Early Retirement Than You Think
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8:44Are you wondering why it feels like everyone else is retiring early — and you're not? In this episode of Early Retirement Roadmap, we uncover the real reasons people delay early retirement, even when they have enough saved. Learn how to avoid the "one more year syndrome," stop chasing unrealistic retirement numbers, and discover 5 proven strategies…
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Episode 461 - The Impact of 3D Printing on Future Housing
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7:43We see lots of cools things 3D Printing can do on social media - how does it impact the future of housing? *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com…
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Avoid These 6 Common Mistakes When Retiring Early
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17:00In this episode, Ari explores six common oversights in early retirement planning that can create unnecessary stress and limit flexibility in the long run. • Not establishing a taxable brokerage account to access funds before traditional retirement age • Overlooking healthcare planning, including available subsidies, which may impact retirement timi…
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Episode 459-Analyzing Housing Supply and Demand Dynamics
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10:14Discover what every investor should know before making their next move - enjoy *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com/iwg-strategy BOOK IS OUT! G…
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Root Talks: Spend Your Way to a Happier Retirement: 5 Pillars of Better Spending
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18:08Many great savers struggle to switch gears once they retire—unsure how to spend with confidence after decades of discipline. James and Ari reflect on the mindset shift from saving to spending, exploring how to use money and time more intentionally to create a meaningful life now, not just someday. Prompted by a thoughtful comment from a Root Collec…
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Tax-Free Income through Alternative Assets with Amir Baluch | Real estate expert
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39:41Dr. Amir Baluch, MD, is a best-selling author and contributor to Forbes. His insights on wealth-building have been featured in major outlets like Entrepreneur, Yahoo! Finance, and Business Insider, further solidifying his reputation as a trusted financial strategist. WHY LISTEN TO OUR INTERVIEW WITH AMIR: [00:00-11:58] Medicine to Investment [11:59…
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Episode 458- The Role of Smart Home Technology in Energy Efficiency
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5:44Home tech isn’t just convenient—it cuts energy costs, boosts property value, and helps investors stay ahead of the curve. Listen for more *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly new…
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Why More People Are Retiring Early Today Than Ever Before
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14:59More Americans than ever before are retiring early due to seven key factors reshaping our approach to work and retirement planning. • COVID-19 accelerated early retirements with 2.6 million more people retiring during the pandemic than expected • Average retirement age dropped from 64 in 2019 to 62 in 2022, one of the sharpest declines in decades •…
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The $12,900 Health Insurance Loophole for Early Retirees!
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11:19What if you could save over $12,000 a year on healthcare—just by choosing the right account to withdraw from to fund your retirement? In this episode, I (early retiree and tax-planning nerd) break down the smartest way to structure your income before age 65 to maximize your ACA subsidy. You’ll learn why your taxable brokerage account might be your …
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Episode 457-How Drones Are Changing Property Inspections
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6:29Listen how drones are transforming property inspections by giving investors a faster, safer, and smarter view—no matter where the property is located *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy an…
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Leverage Generational Wealth and 10X Results with Nicky Billou
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28:13Nicky Billou is the #1 International Best Selling Author of the book: Finish Line ThinkingTM: How to Think and Win Like a Champion, and more. He is an advisor and confidante to some of the most successful and dynamic entrepreneurs in Canada - and the founder of eCircle Academy where he runs a yearlong Mastermind & Educational program working with e…
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5 Retirement Regrets You’ll Want to Avoid
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6:40If you’re planning for retirement — or already enjoying your golden years — this episode is a must-listen. Dive into the five most common financial regrets retirees face, drawing from personal experience, hard-earned lessons, and recent data. From not saving early enough to underestimating healthcare costs, I break down how you can sidestep these p…
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Episode 455-Eco-Friendly Home Renovations: Cost-Effective Strategies
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10:08Trying to cut down on cost? *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com/iwg-strategy BOOK IS OUT! Grab Your Copy and learn how to get your feet wet in…
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4 Tax Strategies To Consider This Year
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16:28Tax strategy is the most overlooked aspect of financial planning, yet it could save you thousands over your lifetime by minimizing your total tax burden rather than just focusing on this year's bill. • Roth conversions let you pay taxes at potentially lower rates now to avoid higher taxes later in life • Asset location matters – keep growth investm…
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Episode 454-Building a Personal Brand as a Real Estate Agent
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4:58As an investor, I was able to connect with awesome real estate agents... these are what they did. *** DON'T KNOW WHERE TO START WITH FRANCHISING? Grab Bob Bernotas' free course for a limited time only at edu.franchisewithbob.com/ideal Any questions? *** Grab my 10k/month passive income strategy and weekly newsletters at https://tinyurl.com/iwg-stra…
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Root Talks: How Does The Advisory Team Structure Work at Root?
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23:50What actually happens when you work with a financial advisor? At Root Financial, we've built a carefully structured team model to ensure every client gets consistent, exceptional service regardless of which advisor they're paired with. Unlike products (think identical Honda Civics or iPhones at any retailer), financial advice is inherently personal…
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Buy and Sell 20 to 30 Properties/month with this Scalable System | Real Estate Expert Interview
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31:44Chris Prefontaine is the Chairman and Founder of Smart Real Estate Coach®, a 4x best-selling author, a Forbes Business Council Member and a 3-time Inc 5000 Honoree for Fastest Growing Company and hosts the Smart Real Estate Coach ® Podcast, which ranks in the top 0.5% globally. WHY LISTEN TO THIS INTERVIEW: [00:00-05:18] Not just a family business …
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