TRAVEL TIP: MAKE CHATGPT YOUR CO-PILOT
I travel a lot, and I’ve never particularly enjoyed traditional trip planning. I like knowing where I’m going, but I don’t necessarily want someone else deciding how I should get there. Especially on a road trip, the fastest route is very often the least interesting one.
That is where ChatGPT has become remarkably useful.
On my recent road trip in the 1969 Alfa Romeo Spider, I didn’t simply ask, “How do I get from Point A to Point B?” I explained the kind of trip I wanted. I wanted curvy roads, great scenery, interesting small towns and as little interstate driving as reasonably possible. I could tell ChatGPT how many hours I wanted to drive, how far I was comfortable going between fuel stops, and whether I wanted the route optimized for speed or enjoyment.
That distinction matters. Google Maps is excellent at telling you the fastest way somewhere. ChatGPT is much better at having a conversation about what kind of drive you actually want and then helping turn that into a Google-Maps-ready route.
For example, instead of asking:
“Give me directions from Spokane to Nelson.”
Try:
“Plan a scenic driving route from Spokane to Nelson. I’m driving a vintage sports car and want great two-lane roads, curves and scenery. Avoid interstates whenever practical. I’d like fuel approximately every 100 miles and a good lunch stop along the way.”
Now you are getting somewhere.
You can continue refining it just as you would with a human travel planner: “Too much highway.” “That day is too long.” “Find me a more interesting hotel.” “Where is the last place to buy premium fuel before this stretch?” “Give me a good place to stop for coffee after about two hours.” It remembers the context of the conversation, so you don’t need to start over every time.
For bigger trips, I recommend creating a dedicated Travel project in ChatGPT and keeping everything related to the trip there: itinerary ideas, hotels, routes, confirmation information, restaurant research and questions that inevitably come up along the way. Instead of having information scattered among browser tabs, emails, screenshots and notes, you have one continuing conversation about the trip.
And then there was the part I hadn’t planned on.
The Alfa had mechanical problems. Lots of them.
Suddenly ChatGPT became less of a travel planner and more of a very knowledgeable passenger sitting beside me. I could describe a symptom, upload a photograph, explain what had already been repaired and ask what we should investigate next. It helped me think through fuel-delivery problems, charging issues, spark plugs, oil leaks and the wonderfully mysterious world of 57-year-old Italian mechanical fuel injection.
I would never suggest blindly following AI advice when repairing a car—or doing anything else where getting it wrong matters. What I found incredibly useful was having something that could help me organize the symptoms, explain the possibilities and give me intelligent questions to ask the mechanic standing in front of the car.
That may be the biggest lesson.
Don’t use ChatGPT merely to ask, “Where should I go?”
Tell it how you like to travel.
Tell it what you enjoy, what you hate, how far you want to drive, what you want to see and what compromises you’re willing to make. Then keep talking to it as the trip changes.
A good road trip rarely goes exactly according to plan.
Mine certainly didn’t.
Fortunately, my co-pilot never got tired of hearing about it.
THE ORIGIN OF SCOTTeVEST
This year marks the 25th anniversary of SCOTTeVEST, which has given me an excuse to look backward in a way I normally don’t. I tend to spend most of my time thinking about what we’re doing next—the next product, the next trip, the next idea, the next thing that needs fixing. But after a quarter-century, it seems appropriate to go back to the beginning and ask a fairly basic question: How did all of this actually start?
Not with a business plan. Not with a focus group. Not with a fashion designer. And certainly not with some grand vision that 25 years later we would still be designing clothing around pockets.
It started because Laura got sick of carrying my crap.
In late 2000, we were living in Chicago and I was trying to figure out what to do with my life. I had left Next50, the dot-com startup where I had been working, and I knew with absolute certainty that I did not want to return to practicing law. What I did not know was what I wanted to do instead. I was doing some consulting work to pay the bills and spending a lot of time walking with Laura around Palos Park, pitching her one business idea after another. Most of those ideas deserved exactly what happened to them: nothing.
At the same time, I had a much more practical problem. I had always been obsessed with gadgets, and in 2000 that obsession required a lot more hardware than it does today. There was no single smartphone replacing everything. I carried a Motorola StarTAC phone, a Palm Pilot, a Sony voice recorder, a Discman, headphones, batteries, chargers, connectors and a ridiculous collection of proprietary cords. When I traveled regularly between Chicago and New Jersey, I carried all of it with me, and I became intimately familiar with the annoyance of digging through bags looking for the one piece of technology I needed at that moment.
Over the years I had tried backpacks and fanny packs, but neither was a particularly elegant solution. Once Laura and I were married, I discovered another option: whenever she happened to be carrying a purse or bag, I would hand things to her.
One day we were standing near the door of our house getting ready to leave, and I started doing what I apparently thought was perfectly reasonable. I handed Laura my phone. Then something else. Then something else. Eventually she had enough.
“I’m not your personal Sherpa! Why don’t you just design something to carry all your own shit around?”
Twenty-five years later, there is still something wonderfully appropriate about the fact that SCOTTeVEST began with Laura telling me, essentially, to deal with my own stuff.
The line stuck with me because she had identified a problem I had been living with for years without ever really questioning it. Why was I carrying all of this technology in a separate bag when I was already wearing clothing? Why couldn't the clothing itself do the carrying? The more I thought about it, the more obvious the answer became: pockets.
I began buying every vest I could find and loading them with the things I actually carried. Old Navy was pushing vests at the time, but theirs didn't have enough pockets. Fishing vests had plenty, but they were designed for fishing equipment and looked like fishing vests. Photography vests had the same basic problem. They all treated pockets as generic storage spaces rather than designing them around the objects people actually used every day.
That became the real insight. A pocket shouldn't merely be a rectangle sewn into a garment. Why not make a pocket specifically sized and positioned for a cell phone? Another for glasses? Another for batteries, a camera or a PDA? Why not think about what people carry first, and then design the clothing around those things?
The wires were another problem. Once, while rushing through an office, my headphone cord caught on a doorknob and nearly ripped the earbud—and possibly part of my ear—off my head. So I began thinking about routing wires through the inside of the garment, from the pockets through the lining and toward the collar. At the time, that meant headphone cables, charging connections, external batteries and even wiring a Palm Pilot to a StarTAC phone to get something resembling mobile internet.
I called the concept the Personal Area Network, or PAN. Later it evolved into our patented TEC—Technology Enabled Clothing® system. Looking back from 2026, when wireless technology has eliminated many of those cords, some of this sounds almost prehistoric. But in 2000 it was a genuine problem, and solving it made me realize that I wasn't simply adding more pockets to a vest. I was beginning to rethink how clothing could interact with technology.
That was when the idea became a company in my head.
Unfortunately, I still had no idea how to make clothing.
Laura and I went to the Merchandise Mart in Chicago and met with an apparel-industry adviser who told us that the next step was simple: make a pattern. She made it sound easy enough that we left convinced we could handle it ourselves. We went to Fishman's Fabric Store on the south side, bought several yards of rough khaki fabric and a box of pins, spread everything across our living-room floor and began attempting to create what I thought would become the future of clothing.
It did not go well.
What sounds simple when you say “vest with pockets” becomes considerably less simple when those pockets overlap, connect, conceal wires, distribute weight and have to remain accessible while someone is actually wearing the garment. The SCOTTeVEST we were imagining was vastly more complicated than anything Laura or I knew how to construct. Over the course of that afternoon, we had one of the very few truly major fights of our marriage. I have never attempted to make a clothing pattern since.
But that failure turned out to be useful. I finally understood that my job wasn't to become a seamstress or even, in the traditional sense, a fashion designer. My job was to figure out what the garment should do. I needed someone else who actually knew how to turn those ideas into clothing.
That person was Susie Kruger. A mutual contact introduced us, I hired her to create the first samples, and suddenly something that had existed only in my head became real. The first prototypes were far from perfect, but I could finally put one on, load it with my gadgets, walk around in it and discover what worked and what didn't. I could move a pocket, resize another, change how something opened and keep improving it.
In a sense, we were developing clothing the way software companies developed software. That thinking is why the first product became the eVEST 1.0. Calling it “1.0” was deliberate. I never believed the first version would be the last version. We would learn from it, improve it, create 2.0 and 3.0, and keep going. Twenty-five years later, that philosophy is still embedded in the company. We are still changing pocket sizes, moving zippers, adjusting weight distribution and debating whether one seemingly tiny modification makes a garment better or worse.
Even the company name came from those earliest days. Scott's Electronics Vest became SCOTTeVEST. At the time I wasn't convinced that we were going to become primarily an apparel company at all. My larger ambition was to license the Personal Area Network technology to major clothing brands—the “Intel Inside” of clothing—with our own vest serving largely as proof that the concept worked.
Obviously, things turned out differently.
Over the last 25 years, the products have changed enormously, the technology people carry has changed beyond recognition, and SCOTTeVEST has grown far beyond that first rough prototype. But the basic design question we asked in 2000 remains almost exactly the same today:
What are people carrying, and how can we design clothing to carry it better?
When I look at the company after a quarter-century, what strikes me most is how much came from such an ordinary moment. There was no boardroom. No investor presentation. No consultant telling us there was an underserved market. There was simply a guy standing by the front door handing too much stuff to his wife—and a wife who finally refused to take any more of it.
Laura has spent the last 25 years as my co-founder, partner and the person who has kept much of SCOTTeVEST actually functioning while I race toward the next idea. So there is a certain symmetry in the fact that she was there at the precise moment the first idea arrived.
I may have designed the pockets.
But Laura provided the sentence that started everything.
And after 25 years, I think she deserves the credit.
BUT INVENTING IT WAS THE EASY PART
By early 2001, we had something tangible. We had prototypes. We had the beginnings of a patent. We had a company name. And I had convinced myself that the traditional path to success was obvious: get the vest into major catalogs and retailers and let them sell it for us.
That plan nearly killed the company before it started.
What happened next involved Hammacher Schlemmer, an order for 3,000 vests, a frightening amount of my own money and one buyer who essentially disappeared at exactly the wrong moment.
And buried inside all of that was a decision I barely thought about at the time. While we were building our first website, the developer asked whether I wanted people to be able to actually buy the vest online. Adding that capability would cost about $500.
I almost said no.
That casual decision would ultimately change SCOTTeVEST—and put us at the front edge of an e-commerce revolution that none of us yet understood.
That’s the next chapter of our 25th anniversary story.
