I would put the 1988 - 1992 millennials up against just about anyone right now when it comes to the highest ROI group for marketing dollars we need to chill

The outperformance you should be seeking should not be measured by nominal returns greater than those of the S&P 500 or Nasdaq Real investment outperformance is what lands in your pocket after taking into account: • Taxes • Fees • Inflation • Risk That’s where I focus the majority of my time in portfolio construction

because you never know when you might be called upon to hit the game winner in your local men’s rec league

texts I get from my wife from while I’m trying to monitor the situation and escape the permanent underclass

If anyone was wondering what the upper bound was for max # of client meetings in a week while managing a 22 month old and 2 month old is I learned this week that it’s 17 Don’t do it

my brother Dave made his TV debut this week! Not every day you see your kid brother on Netflix… Check out “Outlast” (in the top 10 right now):

I am extremely skeptical when things seem too cheap I’ll actually sort by “Price - High to Low” on most websites and start at the top I have no idea why people do the opposite with financial and tax services

10,000 and 1 things I should be doing right now to prepare for the next 2 days of meetings, emails, content it all takes a back seat to this

Liquidity is everything. Matching the need with the right solution in the moment is critical for managing balance sheets. Shortlist of what I see most often: ↳ Company stock options exercise (costs and taxes) ↳ Buy new home before you sell current home (bridge) ↳ All cash home offer without liquidating investments ↳ Major home renovations ↳ Sabbatical, career break, new founder going without a salary (paycheck replacement) ↳ Business acquisition or ad hoc investment opportunity ↳ Large tax payments (liquidity events or 4/15 surprises) ↳ Private K-12 school tuition bills ↳ Semi-annual property tax bills ↳ College tuition deposits The list is endless.

I’ve been investing in secondaries for more than a decade, and I’ve never seen this combination of enthusiasm and lack of financial discipline. The notion that private markets are some guaranteed venture capital trapdoor to returns is misguided. Unless you’re invested in a category-defining company, capital can be impaired just as quickly as in public markets. SpaceX and the frontier AI labs have raised the rim to 20 feet. Their unreal success has distorted expectations for everyone in the asset class.

Hot take (maybe not?) It’s borderline irresponsible to accept more than a handful of SpaceX clients right now without the right support infrastructure or the requisite past equity compensation experience

Fun thread on IPOs from a few years ago:

Everyone should understand how capital gains and losses work. Once it clicks, it's hard to forget:

BREAKING: OpenAI has confidentially filed for an IPO 👀 The IPO market is heating up fast: • SpaceX • Anthropic • OpenAI 2026 is shaping up to be the year of the mega IPO

might as well add 1 more to the insanity that will be my next 5 months