Tax Loss Harvesting Myths Debunked: What You Need to Know Now | AMA #4 with Jesse - E95

Jesse is solo, answering your questions! Kate, a government worker with $650,000 in IRAs, is wondering how she can best rebalance her portfolio - and when. Dan seeks clarity on bonds' role despite recent poor returns, learning they offer portfolio stability and mitigate market volatility, critical for risk-averse investors. Peter asks about Social Security timing, highlighting the trade-off between early claiming's investment growth potential versus the guaranteed, low risk returns of delayed benefits, with traditional advice favoring security. Lucas, a young investor with a taxable brokerage account, asks about key considerations to include when setting up a dividend reinvestment plan. Lastly, Chris wonders how to judge between three potential advisors. If you’d like a question in a future AMA, send Jesse a message!   Key Takeaways: • How to mitigate your risk by diversification. • Why a 10% “sandbox” could be the right thing for your portfolio. • Should you employ a time based or an allocation based  rebalancing strategy. • When you should or should not use bonds. • What is “transfer-on-death”? • How to choose between financial advisors.   Key Timestamps: (00:00) - Review of the Week (01:15) - AMA: Portfolio Rebalancing (10:45) - AMA: Understanding Bond Performance (20:29) - The Role of Bonds in Inflation (25:59) - AMA: Social Security and Investment Strategy (29:37) - Understanding Risk-Adjusted Returns (30:32) - Comparing Social Security to Risk-Free Investments (32:37) - Potential Downsides of Early Social Security Collection (37:39) - Lucas's Taxable Brokerage Account Strategy (50:38) - Chris's Financial Advisor Dilemma   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Tax Loss Harvesting Myths, Debunked: What You Need to Know Now, The Simple 3-Step Formula to Avoid Excess Taxes in Your Investments, Is Splitting Your Portfolio Between Advisors a Smart Move? Maximize Your Capital Gains: Proven Tax Strategies for 2024, How to Avoid IRS Fines: The Urgent 90% Rule You Need to Know   Mentions: “Why Can’t I Take Social Security Early and Invest It?”  https://bestinterest.blog/why-cant-i-take-social-security-early-and-invest-it/  “I Wouldn’t Know Where to Start” – 16 Questions to Ask A Financial Advisor https://bestinterest.blog/financial-advisor-questions/    More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

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Why is personal finance so complicated? The internet is flooded with personal finance “experts” sharing short-sighted, error-prone advice. But long-term financial success requires thoughtful, patient, and well-researched strategies. Hosted by Jesse Cramer, a former aerospace engineer turned fiduciary financial advisor in Rochester, NY, Personal Finance for Long-Term Investors simplifies complex financial topics. With relatable stories, in-depth research, and practical tips, Jesse helps you master financial planning for families, make smart decisions about tax-efficient investing, and build strategies for retirement planning and beyond. Formerly known as The Best Interest Podcast, and inspired by Jesse’s award-nominated blog The Best Interest, this podcast is your trusted resource for comprehensive financial planning and smart investing. Whether you're looking for optimal investment allocations, retirement planning advice, or generational wealth transfer ideas, this show makes personal finance approachable, enjoyable, and actionable. A richer tomorrow starts with learning today. Invest in your knowledge with Personal Finance for Long-Term Investors.