Lots of great investors were only great because they were lucky enough to start their careers between 1985 and 1995.

If the 'best' negotiator is the one who beats the hell out of the other side every time they sit at the table, they typically won't be the 'best' for very long.

So many are focused on building their SMB for an exit; maximizing EBITDA; driving a higher multiple for a strategic sale or PE flip. It’s all about holdcos and multiple arbitrage and whatever Wall Street speak you want to throw around. Maybe the better goal these days is to

As a parent of older kids, three key lessons: 1. Travel sports? Save your money. 2. More family movie nights. 3. Tour loads of colleges - as EARLY as possible.

AI’s coming for HVAC too.

Something bad happened last week and all you Grindset people need to hear it. I was a banker / PE guy for almost 20 years. Then, I started a software business and ran it for a bunch more. Grindset has always been in my DNA. Last week, I co-led a two-day client session w/ a

Seriously, fvck data. I’m in the worst exercise rut of my life. One big reason: data. Data ripped the fun out of my runs. Sure, miles, cool, but I don’t need a watch to tell me that. The other 4,000 data points? Unless I’m training for the geriatric Olympics, WTF cares. And

No one looks back on their life and thinks “My best days were the ones when I was on the XYZ diet and all I did was cleanse and eat fermented avocados.”

Watching AI and tech-driven all-time highs and remembering Yahoo was once worth $125bn.

Live look at Adobe mgmt learning that 90% gross margins + annoying loyal customers tends to attract competition…

Favorite SMB owner quote after turning down our $115mm offer: “All my friends who retired to play golf are dead.”

Reliable data is the lubricant for the capital markets. The alternative is banana republic bullsh|t where insiders mint money with their fingers on the scale. Wanna know what happens when you trade trust for tricks? Enron. Enron on a mega scale.

On a scale of 1 to 10, Montréal in July is a 15. 🇨🇦

Super interesting. So much going on w this. Feels related to Vegas dying given insane cost. BUT, other factors too. First, we’ve stripped the fun out of kids lives. Pressuring them to be pro athletes when they’re 5. Structuring their days so not a moment is free. Math tutors and

Nope, started w/ GFC. Sh|tty businesses bailed out. Wall Street misbehaving. Rando dude in Stockton buying eight houses w $42k in W-2 and blaming the bank - always someone else’s fault when we make dumbass decisions. Politicians and the Fed too scared to let capitalism work.

For as long as I can remember, when things get tough, boomers squeal and politicians react and do things that benefit boomers and screw the youngs. Why? Because boomers vote. Letting markets correct may screw boomers, but it allows the system to cleanse, houses to become more

Amazing how much better my sleep has been since I stopped letting my Garmin tell me “You slept like sh|t last night.” Once again, fvck data. Run, sleep, lift, whatever, and leave the watch at home.

Stopped off in Hanover, NH for the day. I don't care what you Ivy League haters say. Spending four years here as a college kid would be pretty epic.