Play the Long Game - Plus, Burnout & Digital Dementia CPR

What up you animals -

Fake-out spring is gone, the sun is now officially shining in Philly, and I’ve been deep in a Neil Young / Van Morrison vibe. No complaints!

Let’s get rolling.

// The Signal

Urgent Days, Patient Decades

In startup & biz culture, we all kind of worship the idea of lightning-fast breakthroughs and monster exits, but in reality, most real companies are slowwwwww to reach success.

Of course it doesn’t help that slack pings feel like fire alarms, project boards pile up, & that we’re context switching sometimes as much as 1,100 times per day.

Despite our adrenaline - growth timelines actually continue to obey slower physics.

CB Insights’ latest IPO tracker shows that VC-backed companies going public in 2024 logged a median 7.5 years from funding to bell ringing — two years longer than in 2022.

Bill Gates famously quoted, “Most people overestimate what they can do in one year and underestimate what they can do in ten”.

I felt that tug-of-war daily as a CEO. My laptop screamed urgency, yet the business moved on compounding time - and many of the big changes we had to make would quite literally take 6+ months to bear fruit (or not).

Not everything can be an immediate A/B landing page test.

Dorie Clark, biz strategist and author of The Long Game, calls the muscle you need here strategic patience—the discipline to endure the long, silent middle so your work can create an insurmountable gap later on. Sounds a bit extra, but really just means: stay in the game long enough for the wins to truly stack.

Here are two things that helped me w/ strategic patience:

• Curate (and Sometimes Kill) the Feedback:

  I learned to ignore certain feedback - even though it pissed off people sometimes —not because I didn’t care, but because context and sample size matter. One customer asking for a feature? Noted, but parked. Fifty customers asking for the same thing - now it’s time to consider. And for employees, making sure to filter for context: Are they new and seeing ghosts from a past gig, or do they have a fresh POV? Are they angling for a comp bump, or spotting a legit blind spot? The job as CEO isn’t to be everyone’s suggestion box; it’s to guard focus. Deciding which noise gets past the gate may feel contrary to being obsessed over your customers or your partners, but it’s actually super important.

• Hire an outside brain early:

  I waited too long to bring in an advisor. When I finally did—shout-out, Anand—the change was night-and-day. A dispassionate set of eyes helped me gut-check bets, remove emotional comms, kill projects faster, and—surprise—be more patient with the results. A calm, third-party lens kept me from lifting the smoker lid every five minutes and bleeding out all the heat (try and get with that smoked meats reference, ZUCK).

Anyway. For me, the key was to be urgent about execution, and patient with results.

🔖 The Blog Round

Feel like your prefrontal cortex is all up in a blender?

It probably is - because context-switch hell is real.

A new study found the average knowledge worker (that’s you, donkey) bounces between 35 apps per day, stays on a single screen only 47 seconds on average, and it can take up to 23 minutes to refocus after a screen switch.

In my new post, “Digital Dementia: Why Many CEOs & Founders Are Burnt the F*CK Out,” I spell out five tactics that really helped me focus as a CEO—like a 9 p.m.–8 a.m. Slack curfew, calendar-blocked deep-work mornings, and nuking zombie 1-on-1s in favor of GROW reports. I highlight suggest reading this post if you’re feeling the weight of this particular burnout.

🥨 A few Jawns to Check Out

Fear and Loathing in the C-Suite. 

You know it's bad when billionaires start sounding like dissidents. Ken Griffin — Citadel CEO and major Republican donor — said Trump is "eroding the U.S. brand" and making America "poorer." Jamie Dimon, CEO of JP Morgan Chase, called the new wave of tariffs "very bad" for America's credibility. Both took their sweet-ass time getting here. The silence from powerful leaders — the ones who know better — has been deafening. Fear. Money. Self-preservation. At some point, if you believe something is wrong, you say it - before it's safe. Before it's profitable. Otherwise, you're not being a leader, you're just managing your wallet.

Nobody Cares About Your Big Idea. 

My good friend & author Morgan Housel wrote about how the Wright brothers changed the world—and no one gave a shit. Big ideas rarely come with applause—they usually come with shrugs (or rancor). It’s why I try to hold judgement on innovators or contrarians- people doing wild shit (like Bryan Johnson). This is a quick read that’s worth it. 📖 Click Here to Check It Out.

Big is out. Focus is in. 

Janice Min has built and run some of the most iconic media brands out there—but in her convo with Brian Morrissey from The Rebooting, she makes a compelling case for going smaller, sharper, and saner. Her approach with The Ankler is a masterclass in choosing clarity over chaos—and a timely gut-check for anyone still worshipping at the altar of scale. 📖 Click Here to Check It Out.

Alright playas, that’s all for now.

Please feel free to forward this along to someone who’d dig it - or just hit reply and tell me what you liked (or didn’t).

Love yous.

Jordan