Can a robo-advisor like betterment replace your core taxable allocation? tax drag, asset location and performance trade-offs

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 by small multifamily owners: How many months of rent reserves should I keep, and where should I park that cash? It’s one of the most practical risk-management questions in real estate, and the short answer is: it depends. But that’s not very satisfying, so below I walk through the factors I use to set reserve levels, present pragmatic reserve targets for different risk profiles, and explain where to hold the money so it’s...

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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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When I underwrite a property with obvious deferred maintenance, the first question I ask myself is not “how much will the repairs cost?” but “how will the market re-price the asset?” Repairs matter because they affect cash flow, liability, and a buyer’s required return. In practice the market responds not only by reducing near-term NOI but by increasing the cap rate a buyer applies — a cap rate “haircut” that’s often larger...

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I often approach equipment decisions the way I evaluate an investment: weighing risk, expected return, and fit with my objectives. Selecting a padel racket is exactly the same kind of trade-off. Over the years I've test-driven many models from Bullpadel, Nox, Head, Adidas, Wilson, Siux, and Babolat, and I use that hands-on experience combined with a data-minded approach to help you choose the racket that will give you the best performance per...

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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’ve spent years watching REITs move from steady dividend machines to distressed assets — and often the warning signs were sitting in the financials long before the market’s price action screamed “sell.” If you want to spot trouble early, you need to look past the headline dividend yield and dig into a handful of ratios and metrics that reveal credit strain, cash-flow weakness, and operational stress. Below I walk through the...

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I often get asked whether the same valuation metrics apply when comparing single-family rentals (SFRs) in secondary markets versus primary markets. The short answer is: the metrics themselves are the same, but their relative importance, interpretation and the assumptions you attach to them should change based on market context. Below I walk through the specific metrics I use, how I adjust them between market types, and practical ways to test...

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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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When I started evaluating office-to-residential conversion deals several years ago, I quickly realized they live at the intersection of three disciplines investors frequently underweight: zoning and land-use law, construction feasibility, and rent/market economics. You can't simply take a mid-rise office block, slap in some kitchens and call it a day. The devil — and the value — is in the details. In this piece I walk through the practical...

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