CEO & Co-founder of Dray Alliance

Steve Wen

Photo by Cayce Clifford

Steve Wen views his life as a countdown. It’s a feeling that has guided his decision-making since childhood.

Like when he was six and visited the U.S. for the first time, he decided he wanted to live there. His parents agreed, and soon they moved from China to Los Angeles. Their dentist licenses didn’t transfer to the US. Steve’s parents started their own port logistics company to make a living.

Then, there was the time he decided to drop out of U.C. Irvine to become an entrepreneur. His parents didn’t agree with this choice, wanting him to graduate and seek a stable profession. Little did they know, he would ultimately follow in their footsteps and launch Dray Alliance: a port logistics company that uses data and analytics to modernize drayage-—the process of transporting massive shipping containers from ports and rail yards to local warehouses. Steve’s knowledge of the business dates back to working in his parents’ warehouse as a kid.

As his life-long countdown continues, Steve is looking to build Dray Alliance into a global business. We caught up with Steve at the shipping port in Long Beach, CA. It’s one of the two largest in the U.S., meaning virtually every home in the country has something that came through the Long Beach port. As we walk between shipping containers from all over the world filled with everything from food to household goods to toys—“Your Christmas present could be in here!” he says—Steve delves deeper into those life-changing decisions that lead him to Dray Alliance, and what he sees on the horizon.

Take us back to your first visit to the United States. What was it that made your six-year-old self want to come back so much?

It was actually very simple: I liked basketball.

Well, that was one thing. It was also that America was this land of the free where there was so much opportunity for my personality. I didn't grow up to be the most obedient child in China, where the culture was very much: be a good kid, earn good grades, take the equivalent of SAT and go to a good college. Everyone was on the same path. Having that freedom of experimenting, of doing what I wanted to do was very important to me. America seemed like the right place.

What’s something about your childhood that still influences you to this day?

Since I was 10, I started thinking about my life as a countdown. There are too many things that I am curious about and too many people that I care about, so there's an opportunity cost to every decision that I make. After this realization, I started to form a number of frameworks for decision making that I still use today from making highly impactful business decisions to mundane tasks in my personal life.

Is that what led you to drop out of UC Irvine and start down your path as an entrepreneur? How did you end up turning back to the world of shipping and logistics?

At UC Irvine I learned a bit about computer science and finance, and I started small businesses. Some of my original ideas failed and I eventually went into the ecommerce space due to the high likelihood of successes. I sold my ecommerce company, but that experience got me in touch with the supply chain. I saw that there had been virtually no change in how my parents’ business operated. The last mile of container freight was a common source of frustration across the industry. I noticed nobody seemed to like each other. So something had to be wrong. Before Dray Alliance, it was all fax and paperwork. Guys had to spend their Saturdays comparing paper checks to their invoices to make sure they had been accurately paid. So of course, they were extremely unhappy! So that’s where I focused my attention. 

But rather than start Dray Alliance upon seeing this business opportunity, you actually started a different company first. Can you tell us a little bit about that decision?

We knew there was a problem, but I didn't want to be a founder who doesn't truly understand the industry pain point. I believe what drives me is seeing how things are done in action. And being truly part of the stakeholders in these transactions would allow me to see the reasons behind everyone's frustration. There's no better way of doing that then being a future customer of myself. So before I started Dray Alliance, I started a traditional drayage trucking business.

I wanted to be as deep as possible. I wanted to be living in it. I wanted to feel the frustration and inefficiencies in my bones.

I wanted to be as deep as possible. I wanted to be living in it. I wanted to feel the frustration and inefficiencies in my bones. It was a very difficult decision, because I knew it would lead to a lot of pain and, likely, I would not earn a profit. But I wanted to feel it before I started on something bigger. The other reason was also that this time around, I wanted to build a massive business. I didn't want to have any questions that I couldn't answer. We tested as many ideas as possible during that time and got really familiar with the nitty-gritty. After about a year and a half we felt we’d learned enough and started Dray Alliance in 2018—you can think about it like DoorDash but for massive shipping containers. 

Did your parents support you in that process? Did they help you with insight into some of these pain points?

I think they didn't agree with my choice of dropping out of college. They didn't fully agree with my decision of starting my own business at a younger age. They wanted me to find a more stable job. So there was not a lot of support from them. It was helpful, but they definitely raised a lot of questions and tried to persuade me to not do it.

When we first started the trucking company, my parents’ warehouse was our first customer. And we actually launched the business in the backroom of their warehouse with no windows and no AC. It's in the Inland Empire as well, so it got up to 120 degrees sometimes.

That’s a lot of pressure to have your parents as a customer! Do they use Dray Alliance in their business today? How do they feel about your decisions now that Dray Alliance is growing?

They have since retired—and I'm happy that they have retired. Although they did not agree with me, my mother put in almost all of her savings into the company as a first investor. So she's happy that the company is increasing in value.

What is your greatest regret?

My greatest regret is not being able to listen to my grandfather tell his story. He grew up in a war between Japan and China, then was able to participate as a decision maker in the post-war international relationships. There are many stories that have forever disappeared when he passed away. I wish I was able to record his stories and share them with more people.

By the way, what became of your basketball dreams?

I didn't go to my first game until I had enough money to pay for a ticket myself. It felt great, but I was also saddened because Kobe [Bryant] had retired already. It was in college, a Clippers game.

What’s next for Dray Alliance?

There's so much to build because there are so many problems to solve. All of the shipping news we're seeing today, where ports are backed up, every port in the world now has a backlog of container ships waiting to unload. And that's insane. What that means is that the consequence of all of these delays will affect years to come in supply chains. And we're in a changing world order in a way, where the current system was built in the eighties and nineties. So I think there's a real opportunity for us to build the 21st century infrastructure for global shipping, starting from the last mile. 

Steve’s entrepreneurial drive and his deep understanding of the logistics business made an immediate impression on our team here at Headline. Dray Alliance is uniquely situated to meet a large addressable market; and by digitizing the container trucking industry, Dray Alliance drives efficiency and accountability in this last mile of the supply chain. Our Fund VI will lead the company’s Series B financing round.