Two months in at my new job at TrueNorth

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I worked for a FedEx opco for 15 and a half years, 2 months ago yesterday I took a leap of faith and started my first day at TrueNorth, a company that is trying to bring semi-truck (I’m still trying to get “tractor” to stick in my head) drivers into the 21st century by offering various services that make the life of a trucker so much easier by moving things from a world of faxing paperwork to just using an app to confirm deliveries and get money into the hands of the drivers quicker.



You know, the idea was enough to get my interest and I wrote a blog post that I would later learn in the company Slack that put me on the radar of several people in the company that assumed I was an interested owner-operator. I didn’t think I’d quit my job to go work there, I was just writing about another Y Combinator company that caught my interest. I’ve found Y Combinator to be fascinating for many years now, it made the meteoric rise of a friend possible, I visited the San Francisco offices several years ago when I was in town visiting that friend, I did some consultation in an advisory capacity for YC Research (now OpenResearch), and I check the YC forum, Hacker News, most mornings before I even check Reddit.

I had such a good breakfast that morning just before I popped over to the Y Combinator offices in San Francisco. Oh man. So good.

My friend introduced me to co-founder Jin Stedge about a week before the Series B was public and I just assumed nothing would come of it but as with every introduction he has made I went with it and we exchanged several emails. Little did I know a few months later I would be accepting an offer to go to work for TrueNorth and quitting my decade and a half job at a global giant to go to work for a barely 2-year-old startup.

I had no clue what to expect. Here I had been working at a draconian corporate behemoth of yesteryear, piloted by men in their 60s, 70s, and even 80s, that seemed completely allergic to any sort of technological advancement, I mean when I started at my previous employer in 2006 I still had to access my email in a terminal shell…

I’ve been working, legally, since I was 12 years old. I started by delivering papers for 3 cents per with my childhood friend Dani. We both got routes and we’d walk them together, each taking a side of the street. I’ve dug graves, I’ve tossed trucks, I’ve been a government contractor, I cleared international freight through Customs for a decade and a half. I brought home money and was able to pay my bills but never once in those 25 years of work, did I ever look forward to going to work - even when we transitioned to work from home the last 2 years at my previous employer. Work was just some necessary evil, I had to wake up and grind out my day of work so I could get paid

Work was just a necessary evil. Something I had to spend as many as 70 hours a week the past year and change doing. Something I did not look forward to, something I did not like, something I would just try to get through so I could enjoy a little free time doing literally anything else.

TrueNorth is different. I wake up and genuinely look forward to working. I wonder what improvements I’ll make to the product that day, or how I might be able to help a coworker, I wonder what laughs will be had in my meetings for the day.

In the past week alone I’ve had 7 people thank me for work I’ve done, that never happened once at my last employer. In the past week, I’ve been publicly thanked once in our all-hands meeting, and another time in a most-hands meeting. I’m given a lot of autonomy to get my work done, I feel confident doing something without having to tiptoe around asking for permission, and I’m treated like an actual adult capable of rational and independent thought. I’m sure this is largely just the startup world.

I hate when people make some post “ermagerd, I lurv my job, come work here, we r family, omgomgomg much great!” as they are usually saccharinely-sweet, butt-kissing, bull hockey that is little more than self-serving “look at me, promote me, I’m guzzling the koolaid for you!” and that’s 100% not what that is. If TrueNorth told me they didn’t need me anymore I’d be bummed but I’d harbor no ill-will, I’d still be championing the company because I think what they are doing is neat, and clearly, people a lot smarter than me do too based on the aforementioned Series B round. TN is a good company with a great plan.

I enjoy the work, I enjoy the level of trust I am given, I absolutely love the people I work with, and uncharacteristically find myself smiling all the time in Zoom meetings. For that matter I’ll just randomly find myself smiling while working and it’s because for the first time in my life I am truly happy about my job and my career opportunities. I can 100% see myself giving TN 10, 20, 30 years if things stay even 60% the way they are now.

We get a lot of work done, but we also have fun. Several weeks ago in a little ‘fun’ meeting we made a Disney character battle bracket where Mulan of all characters emerged champion supreme. That was the goofiest 20~ minutes I have ever experienced at a job but at the same time it provided us all a quick mental break from our work and let us learn a little more about each other. A dozen times more effective, in my eyes anyway, as a team-building experience than any nonsensical roleplaying tomfoolery I experienced at any previous job.

From the top-down, it’s a great company. Jin can be extremely serious but at the same time exudes this almost motherly, or even grandmotherly, vibe that stays positive. From my limited interaction with Sanjaya, he’s jovial, he’s caring, but at the same time, you see in just a few minutes of a meeting that he’s incredibly sharp and churning away at work, at every level below them we have absolutely wonderful people that give it their all. We have people from all kinds of backgrounds coming together to build this patchwork of expertise. We have a painter, someone that worked on JWST, former truckers and industry experts, quirky lawyers, woodworkers, at least two AFOLs (I must resist the urge to fall back down my Lego addiction), just so many diverse people. Even some of our drivers, which are starting to be featured on the Let It Ride with TrueNorth podcast, are wonderfully delightful characters that I could listen to for hundreds of hours.

This has already waxed far longer than I intended, but I get like that when it comes to things I am genuinely interested in

Thank you S. for making the introduction, thank you Jinn and Alex for being interested in what I might bring to the table. Thank you, Arturo, Austin, Oleg, and Sayeed for interviewing me and deciding you thought I was worth working with. And thank you again Arturo for all those daily meetings at first when you got me up to speed with all of our data, for the patience and effective teaching to get me to the point where I felt component enough to get work done without constantly asking questions and getting me through that full-blown imposter syndrome that had me terrified the first few weeks.

Well, it’s 7:06 AM as I bring this to a close, I suppose I should get downstairs and get on my BikeErg to get my morning started so I can start getting some actual work done.

TrueNorth Transportation Co - putting more money in the pockets of truckers

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Occasionally a company that Y Combinator funded catches my eye, in the past it has mostly been food-related with the occasional SaaS company, but this time it is a trucking company - TrueNorth

TrueNorth Transportation

TrueNorth: Profits to truckers

First, let me preface this by saying I have 15 and a half years of experience in international freight. I clear international freight through Customs and any other applicable agencies. My specific facet of the industry relies on airplanes and what we move via air is just a drop in the bucket of what gets moved by semis. A lot of that stuff you see coming in on cargo ships, yeah, at some point in the delivery chain that ends up being driven by a semi-driver. Break 1-9 for a radio check, something like 72.5% of the nation’s freight by weight is moved by truck.

I think this company is awesome. The trucking industry is full of predatory practices that are all about maximizing profits for companies and not for the backbone of America, CDL truck drivers. You see, the trucking industry is a 700 billion dollar industry in the United States and is only growing. So, what exactly does TrueNorth do? Well, in their owns simple words they help increase “profits to truckers”.

Wait, what do you mean Ryan? Basically, they make the life of drivers easier. building a new operating system for trucking carriers, they've started by building a trucking carrier themselves that consists of roughly 200 owner-operators under their MC. In Nathan Lowell’s science fiction series Trader’s Tales crews of space-based freighters can book loads via a single software platform (maybe someday Ishmael and his peers will use TrueNorth to book freight for their fleets as they work the trade routes in the deep dark!), lining up their loads and handling the bulk of the paperwork from their ship tablets - TrueNorth is doing something analogous to this - TrueNorth's software allows drivers to find and book their next load, plan an efficient route, manage customers they are serving, and most importantly get paid and get paid promptly instead of needing to hound companies to pay their invoices.

Instead of going “there isn’t a problem, let’s make software just to complicate things while we try and make bank off of subscrptions” they’ve gone and realized that the truck driving industry still relies heavily on phone calls and physical paperwork to get things done and they’ve begun building a platform that allows this industry to come from the mid 20th century, screaming past the late 20th century, and into the 21st century. They simplify the work truckers have to do, they get better insurance rates through group buying saving drivers money, they get drivers paid quicker and easier, and who knows what the future will bring from their platform. TrueNorth Transportation is doing something that should have been done ages ago.

This week TrueNorth Transportation hit it out of the park with their Series B bringing in a cool $50 million in funding to grow their operations. They’re operating in a fraction of the country and, from external reporting, appear to already have a very healthy revenue so this is probably going to let them scale as fast as they comfortably can and can start saving more and more drivers from predatory practices and companies that have the lion’s share of the industry.

There is a truck driver shortage right now, and it’s mostly because of compensation. TrueNorth exists to make drivers more profit and to make their work-life just a little bit easier. That’s awesome. Not only is it awesome but it’s refreshingly different in a traditionally predatory industry. Bravo Zulu Jin Stedge and Sanjaya Wijeratne, you are good people.

Update February 4th, 2022

Just wanted to give full disclosure. I liked what I saw so much with TrueNorth that I have accepted a job offer with them as a Data Structure & Quality Specialist!

Update March 11th, 2022

TrueNorth now has a podcast called Let It Ride with TrueNorth! The first episode is a pretty great discussion with two of TrueNorth’s earliest owner-operator drivers Jasen and Lee.