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• 4 Tax Moves That Can Save You 6 Figures - Part 2 of 2

  Your 50s are a tax-planning sweet spot—a decade when smart strategies can save you tens or even hundreds of thousands over the course of retirement. In this episode, Part Two of our two-part series, we explore four advanced but practical moves to keep more of your money compounding where it belongs.Here’s what we cover in this episode:The HSA Triple Play: Why this account is the most underrated retirement tool, and how to turn it into a stealth IRA with triple tax benefits.Social Security Timing & Taxes: How your claiming age affects not just your benefit but how much the IRS quietly takes back.Charitable Giving with Donor-Advised Funds: A Costco-sized deduction now, with the ability to give on your terms for years. Plus, how Qualified Charitable Distributions can kill two birds with one IRA.Bracket Shifting by Gifting to Kids: Move money to lower tax brackets within your family—legally—while supporting education, housing, or even a responsible jet ski purchase.Together with Part One (Roth conversions, withdrawal sequencing, and tax-efficient investing), this gives you a full seven-strategy toolkit for your 50s. No gimmicks, no offshore shell games—just thoughtful planning that keeps more money in your pocket and less in Uncle Sam’s.👉 If this series has been helpful, please leave a review or share it with a friend. It’s the best way to help the show grow—and it keeps me from muttering about Roth conversions to my dogs in the Vermont woods without witnesses.

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• 4 Tax Moves That Can Save You 6 Figures - Part 1 of 2

  Taxes in your 50s may not be cocktail party conversation, but they can make or break your retirement plan. In this episode, I kick off a two-part series on the smartest tax moves to make once the kids are (hopefully) off your payroll and you’re staring down retirement.In Part One, we cover four essential strategies:Roth Conversions: Why your 50s and early 60s may be the perfect window to pay taxes on your terms, not Uncle Sam’s.Withdrawal Sequencing: The order in which you raid your taxable, pretax, and Roth accounts can extend your portfolio by years.Tax-Efficient Investing: How to avoid paying tax on “phantom income” by using ETFs, low-turnover funds, and muni bonds.Tax Loss Harvesting: Turning portfolio lemons into lemonade by using losses to offset gains and shrink your tax bill.Think of this episode as a tax tune-up: no jargon—just practical strategies that can save you tens or even hundreds of thousands over your lifetime.And this is only Part One. Next week, we’ll cover the HSA triple play, Social Security timing, and two bonus strategies for the charitably inclined and family-minded.👉 Subscribe so you don’t miss Part Two, and if you’re finding these episodes helpful, consider leaving a quick review. It helps more people discover the show — and keeps me from muttering about Roth IRAs to my dogs in the Vermont woods entirely in vain.

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• 10 Ways Investors Lose Money Without Knowing It

  Most portfolios don’t implode in one dramatic crash; they leak slowly. A percent here, a hidden fee there, and before you know it, your retirement fund has been funding someone else’s yacht. (Cough, cough...your advisor's...)In this episode, I shine a light on ten common wealth leaks that quietly drain portfolios, plus practical fixes for each one.We’ll cover:How a “tiny” 1% fee can cost you a third of your returns.Why overtrading turns your portfolio into Swiss cheese.The real silent killers: taxes, spreads, and cash drag.Why your own emotions can be more expensive than any advisor.You’ll walk away with a checklist to plug the holes, lower your costs, and keep more of your money compounding where it belongs — in your account, not Wall Street’s.👉 Think of this episode as financial plumbing: we’re finding the leaks before they flood your future. 

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• The Only Asset Allocation Guide You’ll Ever Need

  Your portfolio’s performance isn’t about finding the next hot stock; it’s about how you slice the pie. In this episode, I break down the real math behind compounding, why losses hurt more than wins help, and three simple allocation models you can actually follow without losing sleep.We’ll cover:Why “average returns” are misleading and compounding is what matters.How diversification really works (hint: it’s not about guessing winners).Three practical allocation strategies for different levels of risk tolerance.The surprising case for the “reverse glide path” in retirement.Whether you’re cautious, balanced, or adventurous, you’ll leave with a framework to match your investments to both your spreadsheet and your stomach.And if you’ve ever wondered whether you should own more stocks, more bonds, or just more Advil to deal with it all once you retire — this episode’s for you.

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• The Secret Art of Finding Work You Love and Funding the Life You Want | Chris Hutchins

  Guest: Chris Hutchins, host of All the HacksEpisode theme: Building wealth with meaning—how to design a career (and life) you actually want, while optimizing the money side.What we cover:Meaning > money-first: Chris didn’t start out chasing wealth; he chased options. Early jobs in consulting/banking felt misaligned (little meritocracy, lots of “performance”). That tension pushed him toward work that creates—startups, product, and eventually a podcast.From layoff to leverage: A 2008 layoff forced reinvention. He broke into tech by doing unglamorous, high-initiative work, learning in public, and obsessively networking. Key tactic: create value before you’re hired (he built a full market brief to win a BD role).Career as a cash-flow asset: Once he found work he loved, savings were easier because the job itself provided energy, purpose, and upside. That shift—liking the work—reduced the need to “buy happiness” elsewhere.Optimization without overwhelm: All the Hacks exists to find the 80/20 in money, travel, health, and life. You don’t need to become a points guru or biohacker; borrow Chris’s research and apply the simple levers.Counterintuitive insurance take: When he priced plans, the “best” (premium) plan cost ≈$24k/yr more than the “worst,” while the “worst” plan’s out-of-pocket max was less than that difference. With a real emergency fund and a strong stomach, a high-deductible plan can be rational. (Psychology is the hard part.)Prepay for joy: Pre-buying (subscriptions, passes, prepaid trips) can remove friction and guilt, increasing actual use and happiness.Know your enough: People who don’t know what money is for default to “more.” Define the life you want, price it, then fund that—not a moving target.Audience resonance: “Mini-retirements,” negotiation tactics, and insurance optimization were huge hits; even niche episodes can be life-changing for the right listener.Actionable takeawaysDesign a role you’ll keep doing. Treat your job like part of your portfolio’s fixed-income sleeve: dependable cash flow, lower stress, and compounding skills.Front-load value. Pitch with a one-pager or mini-audit tailored to the company—proof you’ll do the work.Run the insurance math (with your EF). Price premiums vs. out-of-pocket max; let your emergency fund shoulder higher deductibles if the numbers favor it.Prepay strategically. Use prepayment to align behavior with values (fitness classes, transit, annual memberships).Write money rules. E.g., “Invest 20% before lifestyle,” “Use points for intl. biz class only,” “If it saves 10+ hours/yr, buy it.”Lightning-round funBest <$100: Ultrasonic cleaner (for retainers/aligners)—tiny daily upgrade.Most overrated advice: Social-media tax “hacks” that cross legal lines.Apps he likes: A clean net-worth tracker + Copilot for spending (iOS).Guilty pleasure spend: Big annual fees on premium cards—only if the benefits net out.Find Chris: All the Hacks (weekly deep dives). A great starting point: his “Top 50 Lessons” episode.

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