The talent files: From family business to logistics tech

LoadDocs co-founder Darren Chan grew up around warehouses before blazing his own trail in next-generation trucking.

Darren Chan didn’t necessarily realize it as a kid growing up in New York City, but he’s been around entrepreneurs his entire life.

The architect-turned-tech product designer is now the co-founder for San Francisco logistics tech startup LoadDocs. He hails from a family prolific in creating new businesses, from supplying food to restaurants to running glass factories.

After studying architecture at Carnegie Mellon, the New Yorker came back home and found his way into finance before starting his own snowboarding apparel company. Chan always had the bug to work in Silicon Valley, but it wasn’t until an opportunity came around with his now-co-founders at finance tech startup Addepar that he first made the move to California.

In an interview edited for length and clarity, Chan shared what he learned growing up in logistics, how he carved out his own career path in trucking, and the one big thing the industry’s growing number of tech providers are still missing.

What are your early memories of growing up around the family businesses?

Early memories of my father, and still to this day, it’s the typical immigrant Asian male figure. He’s from a tiny farming village in Southern China and worked 24/7 to provide for the family and establish himself.

My mother was born and raised in Malaysia before moving to New York. She was a bookkeeper then a partner in all of the family businesses. Because she also worked all hours of the day, my siblings and I frequently found ourselves hanging around the factories and warehouses after school or during our summer vacations. Those facilities made great playgrounds. How many other kids got to operate pallet jacks or forklifts growing up?

How is it to work in logistics technology now, given that your family was in the business for most of your life?

I didn’t even know that it would technically be called a food service distribution company. I only learned that recently.

Seeing everyone else around me work so hard, I felt like I needed to pitch in. I was tasked with loading some of the lighter products onto our straight trucks for local deliveries. Bean sprouts, broccoli, noodles. None of those boxes ever exceeded 50 pounds. It was physical labor and I had the luxury to treat it like a workout since I could stop whenever I wanted. I don’t think anyone ever really took me and my brother seriously, they were just entertaining us.

I was one of the few to speak English in the warehouses, so my father would get me to hit the phones to plead our case with Perdue to increase our allocation during the winter months. I didn’t understand it back then why we were always getting less than what we ordered during certain months. But with a better understanding of the chicken supply chain now, it could have been a cold snap at the farms, storms causing problems at the processors or the simple fact that they had difficulty getting trailers into the heart of NYC after a bad storm.

As you thought about school or maybe even a career, did you consider really getting into the businesses?

No. That was the sad thing. My father was a serial entrepreneur and he had all these businesses. My siblings and I were not interested in any of the businesses. I think that’s what helped him decide to get rid of some.

He’s the first of four brothers to arrive in the States. As he brought the rest of his family over, he would hand off one of the businesses to each of the brothers. The glass factory went to my third uncle. The restaurant went to my oldest uncle. My second uncle was more involved in the food distribution business. For a time, he would drive the line hauls between our distribution hubs along the East Coast and Midwest to rebalance the inventory between them. During the summers I would sometimes accompany him. I got to see more of America and he taught me the rules of the road. How to signal for passing, thanking other truckers, etc. When he pulled over to rest, he’d give me a roll of quarters and I’d pass the time in the arcades at every truck stop.

So how did you get into the world of design?

That was also due to my father. When the food service distribution business started taking off, he decided it was time to move out of our tiny apartment in Chinatown. He had purchased some land in Brooklyn and had a building constructed, a four-unit apartment building with retail on the ground floor.

That was his pride and joy, and I got to see that building built from the ground up. I was always hanging around the architects and contractors looking at blueprints. I loved drawing as a child, architecture seemed like a legit career to apply my passion for art.

How did the whole world of tech startups get on your radar?

Between high school and college for me, that’s when the whole first tech boom and bust happened. I was on the sidelines watching it go, and it was really interesting.

I had a summer internship working at the Fund for the City of New York. A high school friend and I were basically brought in to build web apps. I loved the dynamic of working with an engineer and seeing prototypes get brought to life. We built apps for kids with diabetes, Planned Parenthood and whatever else the fund was looking into at the time.

My friend eventually went out west to Stanford and started his own company, so it was always in the back of my mind. After enough time in New York, I decided I needed to move out to Silicon Valley.

What made you actually take the leap and move to Silicon Valley?

I was living in Oregon with family, being a ski bum and doing freelance work. That’s when I decided freelancing really wasn’t for me, because you have no control over the final product.

I saw that there was a finance tech company called Addepar in Silicon Valley that had a founder from Carnegie Mellon, and everything happened really fast. I flew down there, met the founders and Will (now co-founder and CEO of LoadDocs). Will took me for a walk along the Bay and by the time we got back to the house, the team told me they were going to make me an offer.

A few weeks later, I remember moving there on a Sunday night, bunking up with an intern and starting work the next morning.

How did LoadDocs and your leap into logistics come about?

After Addepar, I took some time off to recuperate and went off the grid for a few months. I was fortunate enough to spend some time in Africa and the Himalayas. When I went home to see family in NYC, I popped back up on the radar and Will told me he’d be picking me up from the airport when I got back to San Francisco. He had started family since I was gone, so I thought we were going to talk about his kids.

Instead, he started talking about how he had gotten into the logistics industry, he had friends in trucking, they have this huge paperwork problem, etc. It was similar to what Addepar was working on with the financial industry.

I was also familiar, because my parents used to bring home boxes of paper every night. It was the yellow carbon copy paper, the bills of lading. I didn’t know what it was back then, but I sure do now. It was surprising that nothing had changed from what I saw in the late 1980s to now. We’d gone through tremendous changes in other industries, and surprisingly, not much has changed when it comes to moving freight.

Was there a learning curve changing industries?

Yes. I had observed the logistics industry as a kid, and I had observed it from the view of a shipper. A lot of trucks in, a lot of trucks out. But my experience with truckers and trucking companies was more as a customer or a client.

Fortunately we were able to visit Will’s contacts fairly often and learn about their business from them.

What is it like to be a tech company in trucking? It’s obviously a non-traditional role compared to a shipper or a carrier.

It’s interesting. When we first started out, there was not as much interest. I think the industry also wasn’t ready to evolve. In the last few years, we’ve seen much more money and interest coming in from outside the industry. I chalk this up to regulatory changes and the Amazon effect amongst other catalysts.

One of the things we always say is that the technology piece is not necessarily the most difficult aspect. Everyone in the industry recognizes the problems, but it’s hard to change behaviors. Technologists have to work hand in hand with the professionals in the space to streamline workflows in phases.

Looking ahead, what are you most excited about in logistics?

This is a reflection of how fragmented the industry is, and yet partners must work closely together for every single freight move. There’s a lot of tech coming in — IOT, self-driving vehicles, blockchain — that currently only touches one or two aspects of a load’s lifecycle.

When you see tech being adopted en masse, across the ecosystem and across all the partners, I think that’s where it gets exciting.