Founders Don't Get Sick Days

It's another solo one, just Jason and me, this time on founder travel. I kicked things off with the reason I now own three podcast mics instead of one: TSA flagged the thing in my backpack as suspicious more than half the time I traveled with it, so the real travel hack is simpler than any of the gear below. Don't bring a podcast mic.

The Kit That Never Gets Unpacked

From there we got into the actual kit. My travel bag is a $20 backpack off Amazon, not anything fancy, packed the same way every single time so nothing ever has to be remembered: Vuori shorts and a T-shirt, a polo or jacket if there's business stuff, a cheap sleep mask, a tangle-free charging cable I rebuild myself with a 280-watt charger and zip ties for every device, and a small pouch of things that solve 90 percent of the problems that show up on the road. Tajín for food that needs help. Instant Dunkin' coffee sticks from Korea that are somehow actually good. Tylenol Cold and Flu, day and night versions, because a founder doesn't get to call in sick. Advil, Pepto, and Starbucks medicine ball tea on the way out the door. None of it is liquid, so none of it slows me down at security, and none of it gets unpacked when I get home; it just lives in the bag, ready for the next trip.

Jet Lag: Two Different Strategies

Jason and I disagreed a little on jet lag strategy. I use an app called Timeshifter, built on a NASA circadian-rhythm algorithm, that phase-shifts your sleep, light exposure, and caffeine timing before a trip so your body's mostly adjusted before you land. Jason took the opposite approach on a recent Amsterdam trip: he kept his Pacific time schedule the entire time, sleeping from 5:30 a.m. to 1:30 p.m. local, and had zero jet lag going and coming back. It worked, but it only works if the trip doesn't require meeting local clients or syncing up with whoever you're traveling with. My take: figure out what the trip is actually for before you decide which clock to run on.

Do You Still Need an Admin to Book Travel?

We also got into whether AI has finally made the travel-booking assistant obsolete. Short answer: mostly, but not entirely. Booking the flights themselves is a solved problem now; agents handle it fine, and I've even had one dig through a messy Southwest account to find old flight credits that weren't tracked anywhere obvious. What AI still isn't good at is the subtler work an assistant used to do: renegotiating a day's schedule when a flight shifts, deciding which meeting with which important person gets moved and how to ask. That still takes a human touch. I also only book one-way tickets, on purpose, so a single leg can move without breaking a round trip, and I've leaned into airline and hotel status less for the perks than for a psychological reason I call the carpool-lane effect: I once bought a used Prius off Craigslist just for the carpool-lane sticker, because not having access bothered me more than the lane itself ever helped me.

The Vacation We Haven't Figured Out

The episode ended on something a little more honest than a hack. Jason asked if there's a way to actually turn a work trip into a vacation, stay somewhere an extra weekend, actually unplug. I admitted I'm bad at it. Looking back over 20 years, I can remember sitting in an incredible apartment overlooking Central Park, grinding on a website for a company that ultimately failed and that nobody remembers today. My favorite trick when I do manage it is working Hawaii hours, since you're far enough ahead that the workday ends by early afternoon and the rest of the day is actually yours. Jason brought up Sam Parr's old move of cold-messaging someone he wanted to meet with, "I'm going to be in your city," before he'd even booked the flight, and only booking it once they said yes. Neither of us has pulled that off yet, but it's on the list.

🎧 Listen to Founder Mode Episode 82 here:

Founders Don't Get Sick Days

Nov 12 · Founder Mode

21:41

I closed the episode with five takeaways, straight from the show:

Decide what the trip is for before you decide what time zone you're on.
Build a kit that never gets unpacked.
Pack for the bad day. Founders don't get sick days.
Pay for flexibility. Book one-way tickets.
Let the meeting decide the trip, Sam Parr style.

"Pack once, book one way, and look up from the laptop when you get there." - Kevin Henrikson

Final Thoughts

Most of this episode is about building defaults so you never have to think about packing or booking again: the backpack, the kit, the one-way tickets. But the one thing neither of us has actually systematized is knowing when to stop working and look up. That's the part AI hasn't touched, and honestly, the part a good kit can't fix either.

If you know a founder who lives out of a backpack, send them this episode. Subscribe, leave a review, and drop a comment with the one thing you'll never travel without.

This podcast builds on the Founder Mode newsletter.

Let’s build.

-kevin