HeyJaredThe Real Retirement Podcast
What are the real financial strategies retirees need to know to make their retirement successful?Join Stephen H.
- Indexed episodes, last 90 days
- 4
- Latest publication
- Sep 1, 2026
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- Checking…
- Earliest in this view
- Jul 15, 2026
Latest episodes
Have a Huge Capital Gain? Here's What We'd Do (opens the original)
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How should you manage a large capital gain and minimize the taxes you pay? In this episode, we break down how we think about direct indexing, tax-loss harvesting, concentrated stock, exchange funds, 351 exchanges, long/short strategies, and Qualified Opportunity Zones. We explain why long-only direct indexing can be compelling for high-tax investors—and why some sophisticated tax strategies may not be worth the added fees, illiquidity, complexity, and investment risk. If you have significant cap
Concentrated Stock: How Much is Too Much? (opens the original)
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Holding a winning stock can build tremendous wealth, but when one company becomes too much of your portfolio, it can also create significant risk. In this episode, we break down concentrated stock positions, why investors become emotionally attached to their biggest winners, and what the historical data says about the risks of owning too much of a single company. We discuss diversification, behavioral biases, RSUs and inherited stock, and why even great companies don't stay great forever. If a s
4 Lessons Every Wealthy Parent Should Know (opens the original)
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If you feel like you should be getting more value than the AUM fee you're currently paying at your brokerage firm, visit https://engagewithbirchwood.com After interviewing both a successful entrepreneur and his adult son, we reflect on the biggest lessons they shared about raising grounded children, teaching financial responsibility, practicing generosity, and building a lasting family legacy. In this episode, we discuss the four biggest themes that emerged: -- Why generosity may be the most imp
(Pt. 2) How to Raise Grounded Kids After a Business Exit [The Son's Perspective] (opens the original)
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If you've built significant wealth, one question probably keeps you up at night: Will my kids grow into capable, grateful adults? In this episode, we hear from the adult son of a successful entrepreneur who grew up after his family experienced a major business sale. He shares what his parents did well, what shaped his character, what he wishes they'd talked about more, and the lessons he's now applying as a father himself. We discuss parenting, money conversations, work ethic, generosity, faith,
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