I’ve been on a lot of calls lately with private equity firms trying to figure out AI. Not “should we use AI” calls. That ship has sailed. These are the harder conversations: where do we actually start, what’s worth paying for, and how do we get our teams to use this stuff consistently? Three calls in this week. Three very different firms. And yet the same five themes kept surfacing. I think they apply well beyond PE, to enterprise and to non-profits. Build vs. Buy is the wrong question (until...
2 days ago • 2 min read
There's a specific kind of anxiety that comes with being in AI right now. It's not the fear of being left behind. It's the accumulation of "I should really learn that"... the Substack you flagged, the YouTube video someone texted you, the X thread with 200 likes you saved and never opened. For a while, my "learning system" was a graveyard of browser tabs and starred emails. I knew things were there. I just couldn't find them. And the more they piled up, the less I actually learned because...
3 days ago • 1 min read
Last week, a senior leader at a large investment firm opened our Zoom call with what usually sounds like a win: "We've got high usage across the firm." Everyone has access. People are familiar with the tools. A few internal workflows are already connected. Great. I love talking with people for whom AI is really embedded and working. I quickly determined this call was a "trading notes" kind of call. It wasn't a request for help from me. And then, about twenty minutes in, he said shared their...
4 days ago • 1 min read
A friend recently told me about spending a couple of months renting in a place they’d always fantasized about owning. The surprise wasn’t the view or the weather, but the learning. Only after living there did they realize what actually mattered: which floor avoids the parking structure roof, why a third bedroom changes everything, and what “ideal” really means in practice. That’s exactly what I see in AI adoption. Most leaders want the “purchase decision” immediately: platform...
5 days ago • 1 min read
Yesterday I sat across from a legendary investor: one of those people who’s been “right” more often than seems statistically possible. No special dashboards on the wall. No elaborate note-taking ritual. Just a morning routine that starts before sunrise, a constant stream of incoming information, and an almost eerie ability to notice when something in the world stops behaving “the way it normally does.” At one point, they said they get two to three thousand emails a day, but only deeply read a...
8 days ago • 1 min read
Yesterday I was in a room with a group of nonprofit executive directors. We were talking about AI. There was a mix of curiosity + pressure + quiet overwhelm. Because they’re all being told the same thing: “You need to start using AI.” But no one tells them where to start. And for nonprofits, it’s even heavier. They’re already expected to do more… with less… with smaller teams… with tighter budgets… So adding “figure out AI” to the list just feels like one more thing they’re behind on. So...
9 days ago • 1 min read
Yesterday I had one of those calls that starts like small talk and ends like a strategy session you wish you’d recorded. The leader I spoke with runs a large team at a consumer-facing tech company (keeping it anonymous on purpose). They’ve been tasked with driving AI adoption company-wide. Not “run a pilot.” Not “explore.” Company-wide. And they’ve actually made real progress: clear pillars (employee productivity, product innovation, customer service efficiency), early wins in customer...
10 days ago • 1 min read
Last week I had one of those “this will be quick” conversations that turns into a full-on whiteboard session, without the whiteboard. We were sitting on the beach, talking shop. I might as well have had a whiteboard up and a laptop open, but all I had was a phone. Credit to Nanobanana for the image (incl weird year choice and misspelling) You know the type: someone is trying to explain a business case, but the real challenge isn’t the math, it’s the story: Who’s the audience? What objections...
11 days ago • 1 min read
I’m sitting on my flight back from California. Weekend was amazing. Youth sports. Fresh air. Time away. The kind of reset you actually need. And then… real life. There was a moment; one of those parenting ones. She was upset. Didn’t play as well as she wanted. Didn’t like how I responded. Angry. Tears. And if I’m being honest… I didn’t love how I showed up in that moment either. Then, like it does, it passed. We talked. Reset. All better. But it sticks with you a bit. So, back to my flight, I...
12 days ago • 2 min read