I have done a Thursday morning call with a group of 8 amazing entrepreneurs for years and years. All folks that have built and sold a company. We initially created the group to share investment ideas. But of course much of it is personal and family stuff as well. On our last call, we did a thought experiment to see if we would have been better off investing all of the proceeds from our company sale into an S&P 500 index. Rather than the PE, angel investing, RE, equity, precious metals, and bonds we did actually did invest in. You know the answer right? We have all underperformed. Some of us DRAMATICALLY underperformed…like 1/3 return of $SPY. In my case, I sold my company is 2010 and was very slow to build up a portfolio. It took years. And during those years, the index crushed it. Just being underinvested during those years guaranteed that I would underperform. But wait! It gets worse. Not only did we underperform, we also paid way too much in tax compared to holding the index. All of those PE K-1s, LP deals where someone else is making the decision to sell an asset and realize taxable events. Had we each just bought $SPY or $VOO we could have carried interest and paid NO tax other than the dividend payments. If we needed cash we could have just BORROWED AGAINST THE STOCK. Ultra tax efficient. Oh and it gets even worse. All of the illiquidity we took on with these deals. We didn’t get paid a premium for that. The hassle factor. We didn’t get rewarded for that either. Managing tenants in RE, coaching founders in angel investments, reading pitch decks and interviewing GPs, the list goes on and on. We could have bought a dumb single index, paid almost no management fees, and mentally checked out the next minute. And done better. I am not saying the 500 largest US companies will always outperform these other asset classes forever. But what I am saying, is it is damn hard to beat that index. And the truism “time in the market beats timing the market” is, well, true. And the more you transact, generally the worse you do. Tax efficiency is also a major under-appreciated component of wealth preservation. Pic of me and the kids working in the greenhouse, planting trees that will take years to bear fruit. Get it? Get it?

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my latest #dalle obsession is dreaming up sneaker collabs the prompt is pretty simple: “(artist), (brand) sneakers, digital art, product photography” the results are incredible

New York’s nightclubs are the particle accelerators of sociology: reliably creating precise conditions under which exotic extremes of status-seeking behaviour can be observed. Ashley Mears, model turned sociology professor, wrote a great book about them. Thread of key points: