This type of post only surfaces during a bull market, when greed tug at us the hardest, making satisfaction elusive. Ever since making my first public equity investment in 1996, I’ve been hooked, wrestling with the constant mental tug-of-war over how to be at peace with my investment decisions. Maybe you fight the same battles. […]
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After a week of reviewing the tax-free exclusion rule for selling a rental property, I decided not to sell. I’d already used my $500,000 tax-free exclusion amount and would need to wait at least two more years before I could potentially use the full amount again. Most importantly, I’m on a mission to boost my […]
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On the latest episode of the Financial Samurai podcast, I sat down with Ben Miller, cofounder and CEO of Fundrise, for a deep dive into artificial intelligence, venture capital, and what it really takes to get into the best private company deals. Ben was in San Francisco this summer visiting various portfolio companies and trying to make […]
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When I worked in Equities at Goldman Sachs and Credit Suisse, we would occasionally bring a hot IPO deal to market. During the company roadshow, we’d take management around to meet one on one with our largest investors and clients. Sometimes the IPO was so in demand that many clients could not even get a […]
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You Can Use The Tax-Free Home Sale Exclusion Every Two Years To Save On Taxes
4:31 AMIn Spring 2025, I sold one of my properties and successfully excluded $500,000 in capital gains, tax-free, thanks to the IRS Section 121 Exclusion. For those unfamiliar, this powerful rule allows homeowners to exclude up to $250,000 in capital gains if single, or $500,000 if married filing jointly, from the sale of a primary residence—as […]
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Since starting Financial Samurai in 2009, I've encouraged folks to keep an open mind and embrace as many different perspectives as possible. So often, we get set in our ways and think our approach is the only right way to do things. But I can assure you, you're probably missing something—or could do something a […]
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