Author Archives: James Osborne, CFP®

Tax Loss Harvesting: Enough is Enough

I recently had a conversation about the benefits of tax-loss harvesting, specifically about the benefits offered by several leading robo-advisors who perform “daily” tax loss harvesting, and if “traditional” human financial advisors are losing their edge in this space. Tax loss harvesting (TLH) and specifically aggressive TLH, is one of the primary selling points of […]

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Knowing the count

I just finished Ed Thorp’s new autobiography A Man for All Markets and I really enjoyed it. Thorp is, among other things, the man who wrote Beat the Dealer in 1962, the first truly mathematical approach to beating blackjack. He was first to calculate that while betting strategy was important, it had to go along with the cards as […]

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A most unusually average year

By now 2016 is far off in the mirror and everyone is focused on more current events, but I want to take us back a few weeks to reflect on the year that was, at least as it pertains to portfolio performance. First, US stocks, measured by the S&P 500, finished the year up 11.96%, […]

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Remaking Retirement Savings in America

I think a lot about retirement savings. I do retirement planning for individuals, I manage individual and family retirement portfolios, I recommend and manage retirement accounts for small businesses. I help individuals work with their CPAs and TPAs to determine the right retirement plan for them. I deal with salaried employees and independent contractors. Small […]

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2016 In Review

Market Overview Markets turned up the excitement in the fourth quarter, especially with respect to US stocks and domestic interest rates. Stocks were sharply higher after the election with small cap stocks leading the way on a truly impressive run. From November 7th through the end of the year, Vanguard’s Small Cap Value ETF gained 15.05%. […]

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Slow down to go faster

(Warning, bike metaphors ahead). Last weekend I went out for an ice long ride on the mountain bike as winter is threatening on the front range. I headed for Mount Falcon, which is one of the most challenging climbs on the front range on a bike. Steep, technical, rocky, fairly long. I am pretty competitive with […]

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Finance Conferences: G.O.A.T.?

Much has already been written about last week’s Evidence Based Investment Conference in NYC. Put on by the fine gentlemen at Ritholtz Wealth Management and IMN, both the speaker and attendee list was a who’s-who of current and upcoming finance (Twitter) celebs. I won’t rehash sessions and speakers here, but if you’re interested, check out: […]

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Now what?

It’s 10:11pm MT on election night and it would appear that despite nearly universal predictions to the contrary, Donald Trump is about to be elected to be the 45th President of the United States.  Markets are in near freefall overnight, and the last figure I saw was DJIA futures off over 800 points, more than […]

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It’s Working!

Diversified investors finally have something to be happy about. I can tell, because nobody called this quarter to ask (a.k.a. complain) about performance. (Aside – I’m kidding, this practically never happens, my clients are awesome!). What’s the reason?  Here’s year to date performance of various asset classes. Practically every major equity asset class is in-line […]

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You have got to be kidding me with this Forbes garbage

For most of the last year I’ve been getting solicitation emails from the “Five-Star Wealth Manager” people, desperately trying to get me to pay them to make me look like some kind of nonsensical award-winner.  Today’s really takes the cake. Here was the email:     And here is the “offer:”     The lede […]

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Meditations (for investors)

I am neck-deep in the modern translation of Marcus Aurelius’ Meditations (sorry, I couldn’t handle the “thy”s and “thou”s of the old translation, and my Koine Greek is pretty rusty since undergrad. Yes, I’m serious). Admittedly I have fallen in love with it, probably more than I loved Seneca’s Letters from a Stoic which is really saying something for […]

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A Collection of Regrets

Earlier this week I was chatting on Twitter with some folks about my generation and homeownership and mentioned that I regretted buying our “starter home.” This sparked some thoughts about regrets, financial mistakes I’ve made and things I would change if I could go back in time and do it again, at least from a […]

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