So I Bought a Sewing Machine

My plan was to launch Old Road Brand in early 2019. But getting Old Road Brand off the ground took more time that I thought it would. Why? Getting patches sewn onto the hat.  I thought this would be among the easiest parts of launching. Just get the hat, get the patch, and sew them on. Simple. I reached out locally to many different potential sources; independent seemstress’, alteration shops, shoe repair shops, even a local sewing store. Nobody locally could do the job I was looking to have done.  Upon discovery, I learned that a certain kind of sewing machine is needed. One called a “Post Bed” Sewing Machine.

At the end of 2019, I made the mental decision that 2020 would be the year to launch. In the first days of January, I had been eyeballing a Post Bed Sewing machine I had found on CraigsList. The seller had priced it at $1200, but had dropped it to $950. That felt like a divine sign to me. The condition appeared to be very good, and newer than many of the others I had been watching over the course of months. The only problem was that it was located in Portland Oregon. I had already made the mental decision that if I found a Post Bed in Southern California that I would have made that trip. Now it was a rationalization… If I was good 12 hour round trip to So Cal, then a 10 hour one way drive from Portland was doable then too!

I wasn’t sure that my wife would feel the same way. And since she was away at sales meeting, I rationalized that she would find out later after she came back. Begging for forgiveness was going to be the better route than asking permission.

Still… this seemed like a crazy ass plan. I have made the drive from Portland to the Bay Area on a few occasions. Oregon is a hell of lot longer than it looks on a map. And while I have made that drive, I’ve never done it in January. Even when I had made the drive in June many years ago, we encountered snow on a side trip to Crater Lake. The days leading up to the drive I had been keeping an eye on the weather. Sure enough, a cold pacific storm was hitting the region from over the weekend, with a follow up storm arriving midweek.  It looked like Tuesday January 14th would be the day to “thread the needle” between winter storms, and avoid snowy roads or delays. 

It was January 14, 2020, and I boarded the plane in Oakland at 7:00 AM giddy with excitement. Sure enough… I was following through on the plan to buy equipment that would allow me to start assembling hats.  What was the true risk in this plan? If the concept sucked, and nobody bought a hat, I still had a machine of value that I could sell for at least what I bought it for, and maybe even more. So the equipment was never going to be losing proposition. Buying the sewing machine allowed me to get started on Old Road Brand in earnest. No more excuses about how to assemble, I start by doing them myself and just see how it goes.

At the airport in Portland, I picked up a Dodge Caravan minivan with four different tires, and a pull to the right, with hopes that it would safely make the trip, and have a decent radio.  It would be a long day, and mountainous Southern Oregon loomed for arrival just around dusk.

So I Bought A Sewing  Machine

Jeff was the seller the Post Bed Sewing machine. He too is an entrepreneur and designer. He makes handmade shoes, which you have to check out (Instagram: get.kickrich). He works for KEEN and previously NIKE as a product designer.  In a small garage attached to his house was his workshop, he had several leather work sewing machines. He was moving, and no longer needed the Post Bed. I was thrilled that he offered to show me how it worked. It ended up being a 2 hour lesson of the basics, and then some. That alone was worth value to me. I paid him for the sewing machine without haggling on the price.


It was cold in Portland that day, but sunny when we went into the garage. When we were done, we had to access whether or not the assembled sewing machine would fit in the Dodge minivan. As it turns out, no it would not. So, we had to disassemble it. In two parts it would fit nicely. We shook hands, and away I went.

As I drove down the block away from Jeff’s house, it started snowing in Portland, and I was fucking thrilled about the adventure that was about to begin.

The snow was short lived and ended as I was heading through Portland.  Just when I thought I had cleared Southern Oregon,  had forgotten that the Siskiyou range still loomed before I hit the California border. At Ashland I stopped for gas as the snow started falling. Yes, it was dicey. I had no chains. I was driving a minivan, with a worn sidewall. What could wrong?


It was too dicey to take a picture of the snowfall while cresting Mt. Ashland, but it was getting dark, and definitely snowing hard while the temperature was dropping to below freezing.

But it was very pretty on the other side as I cruised down back into  California.


How was the drive? Awesome.  After all, Old Road Brand is a concept celebrating the road trip lifestyle.  A road trip to buy the sewing machine is the epitome of what this is all about. 

Rockin' & Rolling down I-5... Quiet Riot "Come On Feel The Noise" playing on the radio


I left Portland at noon. And pulled into my driveway at 10:15PM.