December 2025 - Monthly Update

Holiday travel is chaos on a timer, and nothing proved that more than my recent Nassau–Miami–Boise trip, where I was given exactly eleven minutes to get off one plane, clear immigration, go through customs, re-clear TSA, sprint across the airport, and board the next flight.

Eleven minutes. I’ve had sandwiches that took longer.

If you saw my two Instagram videos, you know I’m not making this up. The first one is me walking into TSA in Nassau like a man possessed, calmly doing something that makes security lines look like a magic trick. The second is me arriving breathless on the other end, basically laughing at the absurdity of having pulled it off. If you want to see the proof, check out those videos here and here.

Here’s the system.

Right before TSA, I empty everything from my pockets into my SCOTTeVEST. Watch, keys, wallet, passport, phone, sunglasses, chargers, cords, batteries, earbuds, random receipts, whatever duct tape I’m apparently carrying that week. All of it. Then I zip it all up and drop the entire vest into the bin as one single item.

No loose metal.

No juggling trays.

No last-second “where’s my watch?” panic.

No airport scavenger hunt for a falling AirPod.

Just one pocket-packed garment through the X-ray in two seconds.

Meanwhile, everyone else is doing the holiday shuffle: belts off, laptops out, bins stacking up, a full carnival of plastics and panic. I’m already on the other side.

Then I ran. Full-tilt, middle-aged-man, “don’t pull a hamstring in public” running. And because I had no checked bag to wait for, no carry-on to drag, and no overhead bin situation to negotiate, I made it.

Here’s the real tip: don’t check a bag if you can avoid it, especially during the holidays.  Every minute you spend waiting at baggage claim is a minute you don’t have when something goes sideways. Your SCOTTeVEST is a third carry-on that nobody can gate-check, that never gets lost, and that lets you move like you’re traveling on cheat mode.

Load your vest. Toss the whole thing in the bin. Walk through. Go.

It works. I have video proof. And I’m pretty sure it added five years back to my life.

Shop all our travel clothing here.

When people think of SCOTTeVEST, they think pockets. They think travel. They think “how does that guy carry all that stuff?”

What people don’t think about is the unglamorous work it takes to get these products to your door accurately, quickly, and without a single pocket card missing. That work has defined SCOTTeVEST from day one. We don’t tolerate “close enough.” We built this brand on one idea: if we promise you a better experience, we actually have to deliver it.

The early days were raw.

Back in Chicago in 2000, and then later in Ketchum, Laura personally fulfilled every order. Not “oversaw.” Not “managed.” She did it. Every label, every box, every pocket checked. I will never forget one of the very first Cyber Mondays, when Cyber Monday was basically the only holiday shopping event that existed. Laura shipped more than 700 orders by herself. She went in around 11 p.m. the night before, climbed shelves like a caffeinated mountain goat, and packed like her life depended on it. It was heroic and insane and absolutely not scalable.

But as the business doubled year after year, reality caught us. We were growing faster than we could hire. We couldn’t find enough trustworthy help locally. And I could see the impact on Laura. We had a moment that wasn’t dramatic, but it was clear: we can’t keep doing this forever.

Around 2006 or 2007, we began searching for a fulfillment partner. Back then, apparel e-commerce fulfillment was not common at all. And our stuff was uniquely hard to handle. We were putting individual cards in each pocket. Every return had to be checked pocket-by-pocket to make sure the cards were still there and nothing weird had been left behind. Most warehouses looked at our products like they were alien artifacts.

We toured several places and then I flew out to meet with a company called DTI in Bolingbrook. Their personal touch impressed me so much I canceled the rest of my appointments. Tim and Dan treated our business like it was their own. They didn’t just fulfill. They cared. In 17 years, they didn’t make a single packing error. I’m not exaggerating. Not one. They were an extension of us. And to this day, I’m still close friends with both of them.

But time changes things. DTI was acquired and the personal touch slowly faded. The culture shifted. It wasn’t “bad,” but it wasn’t what SCOTTeVEST requires. We are obsessive because you deserve obsessive. If a customer orders a vest with 26 pockets, I want every one of those pockets right, every time. Mistakes are bound to happen, but we admittedly have less tolerance for them. So a hard call was made.

So this past summer, we moved to PBD.

The first move (to DTI) was like moving out of a starter home. This move to PBD was like relocating an entire city. The sheer quantity of product made it brutal. Hundreds of pallets. Over 100,000 labels and items flowing through. Every SKU counted, re-counted, scanned, transferred, and organized.

We shut shipping down for a week hoping to get everything settled. That was cute. We quickly realized we’d need to ship while settling. Nothing would be 100 percent perfect on day one, and customers would understand. So we fought through it. Day after day of tiny delays, tiny fixes, tiny frustrations. Chinese water torture, but with boxes.

There was a moment that captured the madness perfectly. We had a go-live date agreed to months in advance. The date arrived and we all knew we weren't ready. The business equivalent of watching the finish line move away by six feet every time you walk toward it.

But here’s why we did it, and why I’m glad we endured it.

You feel the payoff now.

Faster shipping.

Fewer errors.

Better customer communication.

Tighter inventory transparency.

More reliable deliveries.

Lower shipping costs on our end, which helps us hold pricing as long as we can.

This is the hidden work of building a brand that lasts 25 years. It’s messy. It’s exhausting. It’s often invisible. But you deserve a company that cares enough to do it right, even when it hurts.

We’ve moved fulfillment three times in 25 years. Each move was a step toward doing a better job for you. This one was no different. Thanks for sticking with us through it all.

In November of 2021, I was cooked. Pandemic fatigue. Idaho winter. A year and a half of feeling like the world had shrunk to the size of Sun Valley.

I needed out. Badly.

I didn’t want a big complicated trip. I didn’t want to plan ten moving parts. I wanted something simple that guaranteed movement. So I booked a cruise on Virgin Voyages’ Scarlet Lady. One of their early Caribbean sailings. Adults only. No kids. A suite that didn’t require me to pretend I enjoy bunk beds.

I planned to go alone. I’ve done plenty of solo trips and I’m fine with them. But because the cabin cost basically didn’t change if you brought a second person, I figured: why not invite a friend?

So I did. Short notice. Maybe a week or ten days. I reached out to the usual suspects. Every single one of them had a reason they couldn’t go. Kids, work, life, commitments, or just the deeply rational instinct to not jump on a pandemic cruise with five days’ warning.

At that point I had two choices. Go alone, which I was totally prepared to do, or do something mildly insane that made the trip more interesting.

I chose mildly insane.

I messaged Scott Eddy.

We knew each other from Facebook. I followed his travel life. He’d followed mine. We’d commented here and there. But we’d never met. Never had a meal together. Never broken bread. Nothing. Just internet familiarity.

I wrote something along the lines of: “Hey Scott. I’ve got a suite on the Scarlet Lady. One room, two beds. You’d be sharing a cabin with me. Want to come?”

He looked at his schedule, said he wanted to get out too, and replied, “I’m in.”

That first dinner was surreal. Two grown men, basically strangers, sitting across from each other swapping life stories the way people do on a first date — except with no romance, no awkward expectations, and a lot more honesty. We talked about childhoods, careers, relationships, regrets, dreams, fears. The weird intimacy of being forced to share space turns conversation into something deeper fast. You’re each on good behavior, but you’re also curious. It’s a fascinating dynamic.

The trip itself was a mix of maiden-voyage hiccups and pure fun. Virgin was still ironing out the kinks. They wanted to run everything through an app that barely worked. The ship was full of travel agents learning the product. Great people, but different energy than a ship full of normal vacationers.

We explored islands. I snorkeled. I scuba-dived. I hung out on beaches. I bumped into my buddy Laird on one port and had a mini-adventure.

Then came the dolphin excursion — the one that produced a mutiny.

We spent an entire afternoon scanning the water. Saw nothing. Later the captain casually admitted they had told the cruise line there were no dolphins anywhere near the island, but the cruise sent us anyway because they didn’t want to refund the money.

That did not go over well with me.

Ten of us marched back to guest services and demanded refunds. I have the video. I was laughing and furious at the same time. To their credit, we got our money back, but I’m still not sure if I was leading a protest or starring in a travel sitcom.

The most meaningful moment was meeting Linda (picture of us below!) and Scott Vinton on a beach excursion. She was a flight attendant, he a senior airline pilot, and both longtime SCOTTeVEST customers. We hit it off instantly. It was one of those perfectly random collisions that makes travel feel like fate. She loved the SCOTTeVEST connection, we swapped stories, and it felt like the brand had quietly followed me out into the world and bumped me on the shoulder. 

By the end of that week, Scott Eddy and I weren’t “internet friends.” We were real friends. He later visited me in Sun Valley. We made SCOTTeVEST content together. We stayed in touch. And I realized something important.

Traveling with someone you barely know is a kind of accelerant. You learn who they are quickly. You learn who you are quickly. You get out of your comfort zone, and you grow whether you meant to or not. There’s risk in it, sure, but there’s also a special kind of reward.

That trip accidentally launched a series.

Since the Scarlet Lady, I’ve done more than ten Strange Man trips. Some were epic. Some were awkward. A couple were catastrophes that deserve their own chapter just for the therapy value. But every one of them has been a story, and every one taught me something.

If you want the next chapter, keep reading. I’m just getting started. And if you're interested in more photos, check out the summary facebook post here.