Why I'm Starting Freight Tech from Scratch

In 2026, there will be more freight tech builders than ever before. Some will be from the industry, frustrated with the technology they use, looking to shape their own. Others will be well-funded, VC-backed, highly credentialed technologists looking to swoop into the logistics industry and “hyperscale” to a billion-dollar exit. A new segment will be builders who have never built before, but are powered with AI to take on problems they care deeply about. This blog is for all of them; it’s for builders in freight tech.

The focus of this blog will be on the technologies, challenges, stack, data quirks, operational limitations, and other relevant topics for builders in the space. Builders have to deal with data quality issues, build resilient integrations, prototype new technology, and implement change management to get teams to actually use their tech. I believe most freight tech builders fail, not because they aren’t smart, but because there are a lot of topics to master.

There is an urgent need for ambitious people to help identify and improve the inefficiencies within the logistics industry. At a very high level, more efficient logistics and supply chains mean less waste, lower negative environmental impact, safer roads, and lower costs for consumers. That’s something worth working on.

It’s a truly never-ending and ever-evolving problem, which means it will never be “solved.” To some, that is daunting, but to the right builders it’s never-ending, nonstop fun. Before we start solving, I want to share more about me, my journey, and why you should trust what I say.

I think it’s fair to say lots of people don’t use their undergraduate major every day in their actual profession (i.e., a philosophy major becoming a banker). I use mine every day. I studied Operations & Information Management at the Wharton School of Business. This experience taught me both how to think rigorously about operational issues and how to leverage technology. I use what I learned every single day at work, working with freight brokers and their operations. After I graduated, I worked as an Advanced Analytics & Modeling consultant at Deloitte in Chicago. It was a dream job; I learned how to deliver professional work and sharpened my analytical skill set. But I was restless; I wanted to work at a startup because I knew that was the best place for someone ambitious. Luckily, FourKites just got its Series A and was hiring entry-level operations associates.

I was a young, enthusiastic employee when I started at FourKites as the 35th employee in 2016. At the time, I barely knew how to code; I knew even less about logistics, but I really identified with the space: I liked the idea that on the other side of the technology there were real trucks, real trailers, real facilities, and real people. My first job was to call carriers and get them on FourKites. Spoiler alert: carriers were extremely skeptical, and it took the shipper forcing FourKites on their network for them to comply. We set up carriers with file-based integrations at best, and cell phone app tracking at worst. It was a challenging time, but also extremely exciting. We had huge customers that really wanted us to succeed and deliver, and an awesome, ambitious team that wanted to do great things.

My role quickly evolved to focus more on data after I developed a desktop app that provided basic analytics for shippers. That began my long journey toward more analytics (building more Excel-based analytics with code) and, eventually, custom applications and integrations that worked. I would spend nights and weekends staring at my computer screen trying to get the newest tech to work. After several years of improving my technical skills, solving hard problems, and eventually growing a globally distributed team, I thought I was ready to go out on my own.

At first I did consulting related to all things data analytics and reporting (Salesforce, dashboards, custom apps), but eventually I locked in on what I thought would be my great idea: DJ Tools. I was a salsa/bachata DJ on the side and built DJ tools to grow my business; I thought other DJs would benefit. I built a ton of features (pre-AI days) and got a few DJs from all across the nation to try it, but it was never very sticky and not many DJs paid for it. I then got a call from Thomas Mella about a custom app for tracking teams, which became the foundation of TrackFlo.

At TrackFlo, I’ve been the CTO for three and a half years, and am the sole developer on the application side. We’ve gone through so many iterations and have grown our business and technical sophistication over time. We’ve also now integrated AI into everything we do simply because it makes our small team much more effective. At TrackFlo, I get to work on incredibly cool technical challenges with real customers and real data impacting real people. For this blog, I’ll probably pull from TrackFlo the most, given how much AI has changed the landscape for builders.

This year (2026), I’ll be in my 10th year in Freight Tech and my most impactful one yet. I’m personally excited to share my knowledge and experience in this blog. They say that by writing, you refine your own thinking further; this blog is an exercise in refinement for me: I want to refine my hardest-won lessons all in one place. I’m also excited to discuss technology and problems more in depth. In the world of AI, I hope to provide insights even your latest frontier model may not know and contribute positively to your builder journey, helping solve problems in this industry. The technology changes extremely fast; this blog will help you keep abreast of some of the latest developments and how you can apply them in Freight Tech. Now enough yapping, let’s get this thing started!

P.S. I will be using AI to edit my work and refine my points, but it’s not generating any content.