This week’s song: “For a While I Couldn’t Play Guitar Like a Man” by FREEMAN — Aaron Freeman, aka Gene Ween, stepping out solo after decades of beautifully unhinged Ween chaos. Song’s chilling, in the best of ways.

🎧 Want the whole vibe? Find & bookmark the running playlist right here.

From sound to signal—let’s get this baby rolling with what’s on my mind this week…

One big idea, insight, or take - grounded in the real work, not theory.

A founder told me a story last month.

He spent three straight days in back-to-back meetings laying out a new company direction for employees. Things changed, the market shifted, revenue was wobbly.

So, strategy needed to change.

He walked the team through the risks, the upside, and why he was so excited about the change.

Naturally, people nodded, slack lit up: “This feels right.” “I’m in.” “Let’s go.”

Then - after a grueling three days - he closed his laptop, shut his office door, and literally said out loud, to himself:

“Holy sh*t, I hope I’m right.”

That’s what I call the belief tax.

And this is something I do not hear people talking about nearly enough.

There’s a peculiar exhaustion that comes with leading through uncertainty.

Not from the work itself, but from having to project conviction while you’re still metabolizing doubt.

Your team needs certainty. If you have em’, investors want confidence. And customers want stability.

And yet, you’re still running the math in your head at 2:17 a.m on a Tuesday.

Ben Horowitz wrote in The Hard Thing About Hard Things that the CEO is the one person in the company who can’t lay their burden down.

Reed Hastings has talked about the weight of making decisions with incomplete information — but that waiting for certainty is often the bigger risk. Which sounds rational, of course, but in practice, it means choosing a direction while knowing you don’t have all the cards.

This isn’t fraud, or deception, or being fake.

It’s leadership tension.

The tension between authentic leadership (which includes doubt) and effective leadership (which sometimes requires performed confidence).

So what do you do?

Strategic uncertainty is normal. Markets shift. Data changes. Assumptions get blown up.

Emotional uncertainty is you spiraling. “Am I cut out for this?” “What if I f*ck it up for everyone?” “What if I ruin this product launch?”

Your team can handle strategic uncertainty. But they cannot absorb your existential dread.

Those are different buckets. Don’t mix them.

There are three layers of uncertainty:

Level 1? Share it. It builds trust.

Level 2? Share the logic, but not the wobble or doubt.

Level 3? No thank you. That’s for your advisor, coach, your spouse, your therapist, or the one founder friend who won’t screenshot it or talk sh*t to you later.

You don’t need to be a robot, but you also don’t need to outsource your psychological processing to your team.

If you’re the safe harbor for everyone else, you better have somewhere to unload your sh*t.

This is where a lot of first-time founders screw it up. They confuse vulnerability with broadcasting every doubt to the org, or they confuse a healthy amount of uncertainty with complete melt-down.

Real leadership is knowing where your uncertainty goes.

For me, that’s:

Trust me, everyone needs a place to say, “I’m not sure,” without handing that weight to your team.

Your job isn’t to get rid of uncertainty, it’s to carry it, and then turn it into direction.

And sure, sometimes you’ll close the door after the all-hands and think, “Please let this work.”

That’s part of it. We’ve all been there.

Nobody gets out of paying the belief tax.

You just can’t let it snowball.

Smart reads, sharp tools, or internet gems.

Matt Shumer wrote what was probably the internet’s most forwarded essay last week. His core argument: the acceleration curve on AI is going vertical, and most people — even smart ones — are underestimating how fast this is all shifting from a search-substitute to real-world disruption. I’m not fully sold on the everyday impact timeline, but it’s tough to take the opposite side of this bet. It’s sharp, unsettling, and a little scary. Check it out here.

I’ll listen to old industry killers talk shop all day. Ovitz has been out there, grinding, forever, and you can feel it — the stories, the beefs, the pattern recognition that only comes from decades of reps. Great anecdotes, real business wisdom, heavy on relationships. Check it out here.

If you’ve been wondering what’s actually broken in housing — is it rates, zoning, Wall Street, too many effing billionaires? Welp, consider this your sharp breakdown. Nick Maggiulli looks through the actual data. The answer isn’t as simple as “we just need more homes,” but it’s also not just an income inequality story, either. Check it out here.

No matter who you believe — Gary Marcus, who says that Shumer’s essay is AI panic and doesn’t “contain a shred of evidence”, or Matt Shumer himself, who argues the acceleration curve is about to bend reality… the one thing that’s undeniable is this: the conversation itself is speeding up.

And when the conversation speeds up, decisions do too.

Hope everyone has a great weekend.

And until next time, thanks for reading.

Jordan

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