Portfolio Strategies

I want to share a practical, low-touch workflow I use for tax-loss harvesting across multiple taxable accounts using only free tools. If you're like me — juggling brokerage accounts, ETFs, and a full-time job — it helps to automate the repetitive parts, keep clear records, and only intervene when a real opportunity appears. Below I walk through the process I set up, the tools I rely on, how I avoid wash sales, and a simple logging template...

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Using a home equity line of credit (HELOC) to acquire a rental property can feel like a clever shortcut: tap into the equity you've built, move quickly on a deal, and accelerate portfolio growth. I've used — and analyzed — this approach many times with clients and in my own models. It's powerful when done deliberately, but it can also amplify risk if you treat it like free money. Below I walk through how I evaluate HELOCs as part of a...

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I’ve been asked many times whether a robo-advisor such as Betterment can replace a core taxable allocation in a long-term portfolio. The short answer is: it depends. But that answer isn’t useful without unpacking the trade-offs — particularly tax drag, asset location, and performance nuances — so I’ll walk through how I evaluate this in practice and what I’d consider before moving a large taxable sleeve into any automated...

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I often get asked by investors whether tapping home equity with a HELOC or doing a cash-out refinance is the smarter move — especially when the real goal is to preserve or even improve portfolio returns. I've run the numbers for clients, run scenarios for my own planning, and weighed the trade-offs this article lays out. Below I walk through how each option works, the cost and risk implications for an investment portfolio, and practical...

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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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