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Early Retirement Roadmap

Mike Upland

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每周
 
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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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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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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show series
 
ACA MAGI explained: how to calculate and manage Modified Adjusted Gross Income (MAGI) for Affordable Care Act (ACA) subsidies—step-by-step, with a free MAGI calculator to lower premiums and maximize premium tax credits/subsidies. In this episode, we calculate ACA MAGI step-by-step using a real early-retiree scenario and show you how to keep ACA pre…
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Retirement anxiety does not discriminate based on wealth. Even multi-million-dollar portfolios are not immune to the fear of running out of money. This creates one of retirement’s greatest paradoxes: having enough but feeling like you don’t. When clients hear they can safely spend $150,000 a year in retirement, many hesitate. They remember their fi…
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I never thought you could earn from somebody else’s settlements. But our guest today, Patrick Grimes, introduced us to another (“unique”, I would say) #alternativeinvestment that isn’t mainstream yet. Episode Deep Dive with Action Plan: https://tinyurl.com/ep-joe-tegtmeyer Episode Highlights: [00:00:00-00:02:06] From Tesla to Real Estate [00:02:07-…
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The only episode to update you on 🎙️ #TeslaRobotaxi #SpaceX #TechRevolution Episode Deep Dive with Action Plan: https://tinyurl.com/ep-joe-tegtmeyer Watch on YT: https://youtu.be/EvGv7PyI35w As Tesla’s Driverless Robotaxi takes Austin by storm, we invited one of the number one sources of Tesla’s cutting-edge developments, Joe Tegtmeyer, on the show…
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What makes you trust someone with your financial future? In this episode of Root Talks, James and Ari unpack the powerful role of intuition in building lasting relationships with financial advisors, business partners, and even loved ones. They explain how what we call a gut feeling is actually condensed pattern recognition, your brain quietly scann…
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Episode Deep Dive with Action Plan: https://idealwealthgrower.substack.com/p/how-to-become-a-multifamily-millionaire Don’t miss out on this special episode with guest Mike Morowski. He brings over 30 years of real estate investment experience, having overseen transactions exceeding $450 million! We deepdive into which steps to skip when investing i…
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Are you working longer than you need to because of a retirement planning mistake? One of the biggest misconceptions is assuming you will spend the same amount every year in retirement. The reality is different, and understanding it could change when you retire. Experts call it the retirement smile. In your “go-go years” (65–75), spending is highest…
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Anyone can achieve financial freedom with modest assets (e.g., $ 300,000 at 50% returns covers a $ 100,000 salary), focusing on high-yield diversification. We invited economist, Johannes Bhakdi, who predicts massive asset growth and shares strategies for 50% annual returns via Tesla, Nvidia, real estate, and more - enjoy! Watch on YT: https://youtu…
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This is NOT just another rags-to-riches story of a dishwasher building One Wealth Advisors to $1.2B AUM… This episode is a deep dive into: - Fostering loving, drama-free team cultures that thrived even during COVID -Why job loss fears are OVERBLOWN -Why retirement might NOT BE THE DREAM that we’re sold to. 🌟Don’t miss this deep dive—enjoy! Guest Da…
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Roth conversions vs. ACA subsidies is the early retirement dilemma no one talks about. If you’re planning for early retirement, you need to know how Roth IRA conversions can raise your MAGI and cost you ACA health insurance subsidies before Medicare. In this episode, I’ll break down the trade-off, show you real examples, and share strategies to bal…
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Struggling to get your spouse involved in retirement planning? You are not alone. Many financially-minded partners lose their spouse’s attention by jumping straight into 401(k) allocations or tax strategies. The result is glazed eyes and little engagement. This approach works differently. Start with powerful, open-ended questions that spark curiosi…
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Brian White discusses EVs, batteries, solar, and engineering daily on his channel @futureaza. So it’s an honor to talk about his insights on: * Tesla Investing and Diversification * Global EV Market and Competition * Invest more in Autonomous Trucking and Semis: * AI, Abundance, and Future Society and more… Watch on YouTube: https://youtu.be/CEfe17…
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What happens when growth changes a company? We’ve all seen it—your favorite restaurant expands and suddenly the quality slips. The connection feels lost. But does growing always mean losing what made you special? At Root, we think about growth differently. We use “anti-goals” to define what we never want to become, with checks in place so expansion…
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Meet our first guest Olympian on the show! David Flores Wilson, CFA, CFP®, CEPA®, CM&AA, is a Managing Partner at Sincerus Advisory. His financial guidance has appeared on CNBC, Yahoo! Finance, the New York Times, US News & World Report, and InvestmentNews. Episode Deepdive: *** Start taking action right NOW! 🔥 Need help creating an LLC in the US h…
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Think you know how much people save for retirement? The median American over 65 has just $100,000 saved, yet the average household spends $57,000 a year in retirement, with $20,000 going to housing alone. The math doesn’t work. At Root Financial, most clients retire with $2–3M and plan to spend $100K–$200K annually. That’s not about bragging. It’s …
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Watch via video: https://youtu.be/nga08mEfscM Kristina God’s Online Writing School community helped me monetize my newsletter in just 5 months - so I am honored to invite this expert on my show! We talked about Side Hustle Success, Work-Life Balance as a Mompreneur, Monetizing Writing Online, Substack’s Power Over Social Media, Inspiration and Mind…
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If You’ve Been Telling Yourself: ✅ ✅ “I want to invest smarter, but I don’t know where to start.”✅ “I’m worried a market crash will wipe out my savings.”✅ “I don’t know how to reduce my taxes like the wealthy do.” Then this is your episode because Mark reveals how to invest like an American dynasty, focusing on safety, security, and tax savings. Ma…
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Early retirement at 55 comes with financial and lifestyle challenges most people don’t expect. In this video, I share 5 things I wish I knew before retiring early, including lessons on retirement planning, healthcare costs, spending habits, and mindset shifts that can make or break your retirement years. Retiring early isn’t just about saving enoug…
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Early retirement is about more than money Science shows there are compelling reasons to retire sooner than most people think. The UK’s Whitehall 2 study found that retiring at 60 lowers the risk of chronic disease by 32 percent compared to working longer. Harvard research reveals that close relationships, not wealth or titles, are the strongest pre…
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After listening to him for many years, I'm honored to have Herbert Ong of ⁨@BrighterwithHerbert⁩ on the show! Other than being a T$LA investor, he has also founded 3 companies, awarded the Thomson Reuters Healthcare Star Performance Excellence Award in 2007, and was the Head Product Manager who built and launched CareDiscovery (used by the majority…
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What if the “financially optimal” choice doesn’t actually lead to your best life? This conversation explores the balance between optimizing money and optimizing happiness. We break down the Five Types of Wealth—financial, time, social, mental, and physical—and show why sometimes the decision that looks inefficient on paper may actually be the smart…
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We interviewed one amazing guest who: Built 5 Sales Teams • Co-Founded 3 CRE Firms • Owns TX Investment Portfolio Listen to our interview with Matt Buchalski, a serial business builder, sales leader, and multifamily investor with nearly two decades of experience... about the most practical way to save on taxes as a landlord. Enjoy! #reducetaxes #pr…
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Working past 60 might seem smart, but it could be the biggest retirement mistake you make. In this video, we reveal the hidden costs of working past 60 — from lost health years to missed financial opportunities — and how to find your perfect retirement timing. You’ll learn why the payoff for working longer can shrink after age 60, how taxes and Med…
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Some choose to grind a few more years in a high-paying job they dislike, aiming for an early, full stop at retirement. Others step into more fulfilling work that pays less, but adds purpose to their days—and often still results in more wealth than expected. Take John and Jennifer. Both start at age 50 with $1M saved and $150K salaries. John works f…
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Our guest, Paul Moore, is the Founder of Wellings Capital. After a brief “retirement” in his early 30s, Paul began investing in real estate in 1999 to protect and grow his own wealth. He completed over 85 real estate investments and exits, appeared on HGTV’s House Hunters, rehabbed and managed dozens of rental properties, and developed a subdivisio…
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Dr. David Powers' life compass is "to seek out adventure in everything he does by being intentional, determined, and unstoppable and by energizing and outfitting others to embark on their own adventures". He fulfills his purpose through speaking and books and is a best-selling author in psychology and education. He is a decorated veteran of the Mar…
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Estate planning isn’t fun to think about, but skipping it can cost loved ones time, stress, and money. In this week's episode, Ari breaks down the essentials so you can take action with confidence. Learn the key differences between wills and trusts, which states make trusts especially valuable, and why even residents of “will-friendly” states might…
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I'm so excited to interview Alexandra Merz, the #teslaboomermama. With international studies in London and Germany, she excelled as a fund manager in Paris, overseeing Europe’s largest investment portfolio. She founded companies in Berlin, the South of France, and now, the US - where she relocated via an E-2 Visa. Alexandra assists entrepreneurs fr…
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Money conversations fall short when only one spouse is at the table. It’s easy to treat financial planning like another household task to divide and conquer, but unlike errands, your financial plan is the blueprint for your shared future. What we’ve seen time and again is that the person sleeping next to you often holds the key to your blind spots.…
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Any questions? *** Start taking action right NOW! 🔥 Need help creating LLC in the US https://cutt.ly/nrDZVnHu 🔥 Ask all your real estate questions 1-on-1 https://cutt.ly/FrDZMefv 🔥 Guide to owning SFH investment within one year #onehomeatatime https://cutt.ly/rrDZ9Rh1 Get full access to IdealWealthGrower™ at idealwealthgrower.substack.com/subscribe…
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We're going to talk about the most exciting changes in the investing industry... and that involves AI - let's talk about it. Any questions? *** Start taking action right NOW! 🔥 Need help creating LLC in the US https://cutt.ly/nrDZVnHu 🔥 Ask all your real estate questions 1-on-1 https://cutt.ly/FrDZMefv 🔥 Guide to owning SFH investment within one ye…
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Estate planning doesn’t have to be complicated. This episode breaks down the essentials: wills, trusts, and what actually matters, so you can protect your assets and give your loved ones peace of mind. Wills determine where assets go after death. Trusts do that and more. They can manage assets during your lifetime and help avoid probate, offering m…
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Wondering how the 2025 tax law changes affect your retirement strategy? This video breaks down the One Big Beautiful Bill Act, a landmark tax bill signed into law by President Trump — and its HUGE implications for retirees, early retirees, and anyone planning for financial independence. 📌 Here’s what you’ll learn: 🏦 2025 retirement tax changes that…
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Currency risks got you worried? Axel reveals Bitcoin’s fixed supply as a hedge against inflation. In this episode, Axel suggests reallocating 5-10% of disposable income to Bitcoin or gold to protect your wealth from inflation. Why? Tune in to learn why and thrive in the shifting money markets! Any questions? *** Start taking action right NOW! 🔥 Nee…
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Curtis May is the creator and owner of Practical Wealth Advisors (PWA) and host of The Practical Wealth Show Podcast. By following the principles of wealth creation, Curtis teaches people that their number one financial asset is their knowledge. The more they know, the lower their risk, and the greater their chance of success over time. Не feels st…
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What does soccer have to do with retirement? A lot more than you'd think. As a 5'5" former college soccer player turned financial advisor, I’ve learned it’s not about brute strength. It’s about smart decisions. That mindset guides the way I approach financial planning today. At 29, people ask why I care so much about retirement. The answer is simpl…
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In this episode, Axel shows how real estate and stable stocks create a lasting legacy. Tune in to grasp strategies to protect your wealth for your family in an abundant future. Any questions? *** Start taking action right NOW! 🔥 Need help creating LLC in the US https://cutt.ly/nrDZVnHu 🔥 Ask all your real estate questions 1-on-1 https://cutt.ly/FrD…
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Want early access to your 401(k) or IRA before age 59½ without getting slammed by the IRS 10% penalty? In this episode, I’ll walk you through the IRS Rule 72(t)—a little-known but completely legal loophole that allows penalty-free early withdrawals through SEPP (Substantially Equal Periodic Payments). This strategy could unlock your early retiremen…
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Chasing quick stock market wins? Axel warns against speculative traps that risk addiction and loss. Focus on long-term real estate and stocks for steady 4-8% gains instead. Tune in to discover how to build wealth safely without gambling your future away! Any questions? *** Start taking action right NOW! 🔥 Need help creating LLC in the US https://cu…
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The hardest part of retirement isn’t always financial, it’s psychological. For many, stepping away from work isn’t a light switch, but a dimmer that adjusts over time. This episode of Root Talks unpacks what makes the retirement decision so complex, especially for high-achieving professionals whose identity is tied to their careers. Through a real-…
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Bob Frady is a data-driven entrepreneur and the co-founder and CEO of PropertyLens.com, a real estate technology platform helping homebuyers uncover hidden risks—like past floods, unpermitted work, and fire exposure—before they make an offer. A veteran of the insurance and data analytics industries, Bob previously co-founded HazardHub, a property r…
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Too bad we weren't taught money in schools. In this episode, Axel advises you on how much % of your income to invest in investments like Palantir stocks or real estate. Small steps now can lead to millions. Tune in to discover how to build a portfolio that frees you from the 9-to-5 grind! Any questions? *** Start taking action right NOW! 🔥 Need hel…
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Ready to feel more motivated about retiring early? These five research-backed stats reveal how early retirement can positively impact everything from health to relationships—and might be the nudge you need to take your financial independence plan more seriously. The benefits go well beyond just having more free time. While many people delay retirem…
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Are you really ready for retirement? As your retirement countdown begins, I reveal the critical steps you must take to ensure you're fully prepared to retire confidently and securely. From defining your retirement vision to setting a realistic retirement age, I cover everything you need to know for effective retirement planning. In this retirement …
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If you've ever said, “I wish I had invested sooner,” this episode is for you. In this episode, Axel breaks down the hidden price of overthinking your investment moves—from missed equity gains to inflation erosion—and shares why waiting for the “perfect” deal might quietly be costing you thousands. What does waiting actually cost you? Any questions?…
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In this episode, Roger Wesley breaks down what most investors miss—and what smart investors do differently. He unpacks his biggest lesson moving into real estate + how conviction, clarity, and communication can transform your career and help raise capital in unexpected ways. Married with 4 kids and counting, Roger is a committed husband and loving …
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Thinking about early retirement? Here are 6 powerful reasons to retire early—covering retirement planning, financial freedom, health, and why waiting longer could cost more than money. Whether you're close to retiring or just exploring the idea, these insights might change how you think about work, money, and time. Inspired by the popular topic “5 …
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Think your real estate portfolio is secure? Think again. Axel breaks down the hidden impact of currency shifts on your asset allocation strategy—and why your $200K property might not be worth as much as you think (depending on where you live). From Bitcoin's new highs to international real estate value gaps, tune in to learn how global forces silen…
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Too many people delay retirement just to boost their Social Security benefits, often at the cost of time, energy, and joy. But at Root, we believe retirement planning should be about more than just maximizing one metric. It should be about maximizing your life. If you're working extra years simply to avoid gaps in your earnings history or to earn a…
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