Nantucket, Nostalgia, & Nonsense

Trust Fun is brought to you by Aftersell by Rokt

NEW SPONSOR ALERT. AND A BIG ONE. Keep reading plz so I can pay for my vacation.

Rokt Ads for DTC, powered by Aftersell, puts your brand in front of shoppers right after they check out on sites like Disney and Ticketmaster—basically, when they’re still in “sure, I’ll buy that too” mode.

Why care?

• High-Intent Timing: Ads show up post-purchase when wallets are warm.

• New Customers Only: Built-in controls so you’re not just retargeting the same crowd.

• Enterprise Tech for the Rest of Us: Used by giant brands—now available to Shopify stores.

Oh, the kicker? They’re giving away $10K+ in ad credits to select brands to try it (YES, $10,000 IN FREE MARKETING DOLLARS). I’m doing it. You should too.

Check it out here 👉 Aftersell by Rokt $10k Ad Credits

I’m typing this on the ferry from Hyannis to Nantucket, because apparently I can’t go a single summer without drifting back here like some overgrown homing pigeon. My college friends have rented a house every 4th of July week for the past few years. I usually stay a few days (that’s all I need), then head back to the North Shore for the real fireworks. It’s probably my favorite ritual I have going on right now.

Massachusetts in the summer is, sincerely, the best place in the world. I know everyone’s got their regional loyalties—Michigan, Lake Tahoe, etc.—but this is the alpha spot. I mean, it’s one of the original birthplaces of America. Paul Revere? Ever heard of him. Not that I’m out here saluting the flag on my front porch (I’m definitely not), but on the 4th? I have my patriotic moments.

What I love about this time of year is it feels like pressing pause on adulthood. Sorta like I’m 12 again, deleting ice pops, sand in my bedsheets, forgetting what day it is. And the older I get, the more I’m convinced that holding onto that headspace—some version of wide-eyed, maybe-a-little-delusional, childish optimism—is actually the thing that keeps you moving forward.

I’ll own it: I am indeed fully delusional. I still think, on some level, I could be President of the United States one day. (I won’t, but that’s my choice.) I still believe, if I really locked in, I could maybe play for the Boston Red Sox. And yeah, I know how that sounds. BUT, an Olympic speed skater named Eddy Alvarez re-started playing baseball in his late 20s & made it to the majors. Look him up. Great story. So, all this to say… why not me?

The thing is (and here is where I try to make my ridiculous, somewhat incoherent argument) this isn’t just me romanticizing my own nonsense. There’s actual research on why this mindset matters:

• Harvard Business School has research showing that “counterfactual thinking”—imagining alternate scenarios—is linked to more creative problem-solving. Basically, daydreaming isn’t a waste of time.

• Stanford found that approaching challenges with a “play mindset” helps you adapt and perform better when things get hard.

• Carol Dweck’s Growth Mindset work shows that believing you can get better—however irrational it feels—literally makes it more likely you will.

I think about this a lot. That some amount of unreasonable optimism—paired with enough humility to know you still have to do the work—is probably the only way anything good gets made. Be self aware. But also, be a child. It’s not that hard.

If you’re feeling stuck, or jaded, or like every idea has already been done, maybe the most productive thing you can do is let yourself act like a kid again. Be curious. Be a little naive. Imagine it working, even if no one else can see it yet.

And if that sounds silly, well—silly has a pretty good track record.

Catch you next week. In the meantime, I’ll be at Cisco Brewery drinking Blue Seals (real ones know), explaining to a random stranger why cereal is actually just breakfast soup & how if I 100% focused on golf for a year straight I could make the Web.com tour.