Portfolio Strategies

I’ve evaluated dozens of multifamily deals over the years, both as a solo investor and as a passive participant in syndications. Deciding whether to lead a purchase on your own or to join a multifamily syndication is not just about capital — it’s about time, skills, risk tolerance, and the quality of the sponsor. Below I share a practical checklist and the decision framework I use when weighing syndication opportunities versus buying solo....

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I often get asked how to generate reliable, predictable income from an equity portfolio without surrendering long-term growth. One practical answer I use in my own portfolios is to create a “covered-call sleeve” built around low-cost Vanguard ETFs. In this article I’ll walk you through a repeatable, tax-aware approach: which Vanguard ETFs I prefer as the underlying, how to size the sleeve, how to structure monthly covered-call sales, and...

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I often get asked whether Vanguard target-date funds (TDFs) can double as a taxable retirement glidepath — that is, whether you can hold a Vanguard TDF in a taxable account and simply use it as the default sequence of withdrawals during retirement. The short answer is: yes, you can, but the tax consequences and practical implications mean you should approach this deliberately rather than by default. In this piece I walk through the tax...

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I’ve been combining dividend investing with covered-call overlays for years to extract incremental income while keeping downside risk in check. When done carefully, a covered-call “income sleeve” can boost cash returns for a dividend-focused portfolio—but tax treatment can quietly erode those gains if you don’t structure it correctly. Below I walk through a pragmatic, data-driven way to build a tax-efficient covered-call sleeve that...

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I hunt for gains, but I also focus on the messy, underappreciated side of investing: taxes. Over the years I’ve used tax-loss harvesting (TLH) as a pragmatic tool to reduce tax drag in taxable accounts. Doing it well across multiple taxable accounts — and when you’re rotating into similar ETFs rather than identical ones — requires clear rules, careful record-keeping, and a dose of common sense. Below I walk through how I harvest losses...

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Generating steady income from options is attractive: premium flows, time decay working in your favor, and a wide menu of strategies from covered calls to credit spreads. But the same leverage and asymmetric payoff that make options lucrative also create concentrated downside risk if you size positions poorly. I approach options income the same way I approach real estate or equities: start with clear allocation rules, measure potential loss, and...

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I often get questions from readers who are approaching retirement with a relatively small nest egg and a big fear of sequence-of-returns risk: “How can I avoid a large drawdown in the early years of retirement?” Volatility targeting is one practical technique I use and recommend to help smooth drawdowns while keeping a meaningful allocation to growth assets. In this article I’ll walk you through what volatility targeting is, why it matters...

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I run scenario analysis on my clients’ retirement plans like a pilot runs checklists before takeoff: it’s not glamorous, but it’s the thing that prevents disaster. When I talk about a portfolio’s “glidepath” toward retirement income, I mean the path your asset allocation, expected returns, volatility, and withdrawals together create as you transition from accumulation to distribution. Scenario analysis doesn’t predict the future....

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I’ve helped investors and real estate owners quantify risk and design practical hedges for years, and one of the most common problems I see is a concentrated stock position — often an employee with most of their net worth parked in one company. Options are a powerful, flexible tool to reduce that tail risk without necessarily selling shares and triggering a taxable event or giving up upside. Below I walk through the approaches I use and...

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I often get asked how to validate an investment idea without paying for fancy software or hiring a quant team. One of my favorite ways to do that is to backtest a straightforward momentum strategy in Excel using free data sources. It’s practical, transparent, and — crucially — reproducible. In this article I’ll walk you through the exact steps I use, including where to get data, how to structure your spreadsheet, the formulas to...

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