My wife put me onto this one. "Basic Being Basic" by Djo, which is Joe Keery (Steve Harrington from Stranger Things) making music under a different name. Recorded at the famous Electric Lady Studios. Bunch of b*tches being basic, faking the funk.

🎧 Want the whole vibe? The 2026 playlist is 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.

I was emailing back and forth with a very successful serial entrepreneur the other day.

At one point he said something that really made me stop mid-morning coffee.

"One of the biggest differences between first-time founders and repeat founders is how they think about probability."

Most founders hear "10% chance of success" and immediately walk away. It’s way too risky, not worth the energy.

But that's not how the best operators evaluate bets. They're not fixated on probability, instead they're thinking about expected value.

Here's the simple version:

Expected value = (probability you're right × upside) vs. (probability you're wrong × downside)

Say there's a move you could make with a 10% chance of success. If it works, the upside is $10M.

10% × $10M = $1M expected value.

Now assume there's a 90% chance you're wrong, and the downside costs $100K.

90% × $100K = $90K expected cost.

So you're looking at $1M in expected value against $90K in expected cost. Anyone doing that math would say: take the f*cking bet. By a mile.

Yet most of us (myself included) don't actually do that math. We anchor on the 10% and think: long shot. But the experienced founder sees the exact same situation and thinks: the upside is wildly disproportionate to the downside.

Same facts — completely different decision.

Part of it is experience. Serial entrepreneurs have made enough bets that they trust their math. They've seen a few 10% shots actually hit, and that changes how you evaluate the next one.

But there's another reason that's more sneaky.

Running a company forces you to zoom in. You're dealing with hiring, customers, product issues, payroll, blah blah blah. Everything becomes tactical. You're hyper-focused on the thing right in front of you.

But expected value thinking requires the opposite. It forces you to zoom out and ask a bigger question: is the upside here wildly larger than what I'd lose if I'm wrong?

Those are the bets that build incredible companies. But they often look uncomfortable in the moment because the probability of success isn't high. So we pass. We keep making the safe, high-probability moves with modest upside. And those moves feel responsible, but if you only play those hands, you end up building something that never quite breaks through.

I've done this. Passed on moves that scared me because the odds didn't feel good enough, even when the downside was pretty contained. Looking back, the math was right there. I just wasn't running the numbers, or I was too scared to.

I've also done the opposite. Took the swing anyway. And man, it's been worth it every time.

When you're staring at a big decision, run this quick check:

If the answer to #3 is yes, you're probably looking at an asymmetric bet. And if you keep walking away from those, you have to ask yourself what you're actually building toward.

Smart reads, sharp tools, or internet gems.

HubSpot cofounder and Dead Head Brian Halligan has his own pod, and this one w/ Ben Horowitz is the best episode yet. They get into founder mode, hiring, why deferring too much to "experienced" execs creates politics, and why avoiding senior talent altogether is just as dangerous. The part on hiring salespeople is especially good. If you're a founder building a team right now, this one's worth the full listen. Check it out here.

This is one of the sharpest things I've read on moats in a while. Sid breaks down why most startups don't actually have defensibility, they just have a head start, and in 2026 that head start might be worth about six weeks. He lays out seven real sources of durability, and none of them are "our tech stack." If you're building something right now, this is worth 10 minutes. Check it out here.

I don't love how he frames this as "gentle parenting doesn't work." It’s the wrong frame. The real takeaway is that structure (and, sometimes, “strictness”) beats no structure, and the data backs it up. Teenagers report better relationships in homes with curfews, screen limits, and bedtimes. Not because rules are fun, but because kids feel safer when someone's willing to hold the line. High warmth plus high structure is the formula. Check it out here.

Whether it's a big bet or a big hire, the pattern is the same: the thing that feels uncomfortable is usually the thing worth doing.

Just make sure you do the work around it.

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