Billy Strings keeps redefining bluegrass — three Grammys, sold-out arenas, a collab with Willie Nelson — and "Away From the Mire" is the one I keep coming back to.

🎧 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.

Try to quickly picture this.

You walk out of a team meeting feeling pretty good. Clear priorities, maybe a little bit of debate, everyone nodding at the end. You even said, “Alright, great, we’re aligned.”

Two weeks later, you’re staring at your screen, thinking:

Wait.

Why wasn’t this done?

You scroll Slack. There was a thread. Some updates. A few emojis. But the thing itself?

Still not done.

So you step in - you ping. You ask for a status update. You clarify “what you meant” when you said you wanted the new feature rolled out by end of January.

And just like that, you’re the accountability system again.

If you’re building in the $2M–$10M range, this stage is almost universal.

Revenue’s real. The team is legit. You’re not building in momma’s basement no more.

But it still feels like a whole lot of micromanagement.

Most founders in this spot assume the issue is:

But trust me, most Babysitter founders aren’t babysitting because their team isn’t motivated.

They’re babysitting because ambiguity is running the company.

There’s a reason Patrick Lencioni says “the enemy of accountability is ambiguity.”

It’s not laziness or incompetence. But ambiguity.

And ambiguity isn’t something that’s so obvious that it punches you in the face.

It looks more like this:

But, silence in a meeting isn’t agreement; nods aren’t commitments; and “next week” isn’t an actual date. Most founders believe they’ve been clear. Most teams believe they’ve aligned.

But no one actually locked the commitment:

Owner.

Deliverable.

Date.

Definition of done.

Jason Cohen wrote a great piece called “Failure to Face the Truth.” The idea is simple: we avoid uncomfortable realities. In startups, that often means avoiding the small, awkward clarifications that would prevent bigger problems later.

You know the deadline should be Wednesday, not next Friday.

You know the team member may have too many things on their plate.

You know the priority isn’t actually clear.

But tightening the language feels confrontational, and you don’t want to seem intense, or unfair, or impatient.

So you leave it a little fuzzy.

But this is exactly where things slip - it’s not a people problem, it’s a you-clarity problem!

If you don’t force specificity at the moment of commitment, you will pay for it later in management time. Every vague agreement becomes a future follow-up. Every soft deadline becomes another calendar reminder for you.

Before a meeting ends, ask:

Who owns this?

By what exact date?

What does “done” actually mean?

What would make this slip?

If someone says “maybe by Friday,” that’s not awkward. That’s data. Stay there.

Leadership often happens in that moment — not in the strategy deck, not in the all-hands, but in the slightly uncomfortable sentence:

Follow-up: “Friday morning, or COB? And why “maybe”?”

Dig in and get specificity.

If you’re still the accountability system at $2M, that’s probably fairly normal. If you’re still the accountability system at $5M-$10M, you don’t have a motivation problem, you have a precision problem.

Smart reads, sharp tools, or internet gems.

The Atlantic published a great piece on AI and the labor market. It's got economists disagreeing with each other, CEOs going completely silent after openly predicting mass layoffs, and Steve Bannon calling for the government to take a 50% stake in AI companies. If you've got 20 minutes this weekend, this one's worth it. Check it out here.

Team USA just won Olympic gold and left one of the best defensemen in the world at home to do it. Writer and PE Operator Paul Stansik breaks down why cutting Adam Fox — a Norris Trophy winner — was actually the right call, and what it tells you about hiring for the stuff that doesn't show up on highlight reels. If you're into team building of any kind, it’s super solid. Check it out here.

Airbnb's founder made an astute point: we're mostly all still doing the same sh*t, just on a few new apps. Same screens, same habits. His bet is that the real behavioral shift is still 3+ years out, when AI enterprise moves more consumer. Not a knock on AI, just an honest read on where we actually are vs. where the hype says we are. Watch it here.

Yeah, I know — it's been a lot of AI content lately. I can't help it. February has been insane on the AI front and I'd feel like I was doing you dirty if I didn't flag the stuff worth reading.

Have a great weekend, and until next time, thanks for reading.

Jordan

P.S. Wanna work on something? Got a pod or content idea? → Email me | Need 30–60 min of advice? → Book here | Want a coach in your corner? → More info