Haiti-Born Pierre Laguerre Dropped Out Of College To Drive A Truck. Now He’s A Logistics Entrepreneur Pioneering A New Generation In Trucking

Ebony Grimsley-Vaz
Written by Ebony Grimsley-Vaz
trucking
Haiti-born Pierre Laguerre dropped out of college to be a truck driver. Now he’s a transportation logistics entrepreneur. His mobile platform, Fleeting, is seeing 30% month-over-month growth connecting commercial drivers with on-demand trucking jobs. Photo By Cyrus Baron, provided by Fleeting

As more people turn to e-commerce for their daily needs, the need to move products around the country is more urgent than ever. The trucking industry is on track to experience a shortage of 100,000 drivers by 2024, according to a report by the American Trucking Association.

Pierre Laguerre wants to lead the way in closing the gap in the predicted shortage. He’s the founder and CEO at Fleeting, a mobile platform that connects commercial truck drivers with on-demand trucking jobs. Since launching this mobile platform in 2019, Laguerre says Fleeting has seen 30-percent month-over-month growth.

A three-time entrepreneur, Laguerre has almost two decades of experience in the logistics transportation industry. He credits his knowledge of the industry and listening to customers’ pain points for the quick growth of his company so far.

“In my head, it’s like, ‘OK, how much are you willing to pay to make that pain go away?’ Once I started looking at that way, I started to really dig in,” Laguerre told Moguldom.

While Laguerre has heard his fair share of “no’s”, he has also won pitch competitions and generated revenue.

He was able to fundraise $500,000 from investors who believed that, “Yes, this startup has potential”. He counts among his investors Arlan Hamilton and Chamillionaire.

Laguerre shares with Moguldom his views on autonomous trucks, how his first two companies failed, how being hospitalized changed his outlook on growing a new tech startup, and how he’s pioneering change in the culture of transportation.

We want to change the stigma of working in transportation logistics — make it more appealing to bring more millennials, LGBTQ communities and other marginalized people to understand how important trucking is and that they can make a lot of money on their own terms. These are the things that in five years we look to be pioneering and leading: a new generation in trucking.

Pierre Laguerre, founder and CEO of Fleeting, a mobile platform that connects commercial drivers with on-demand trucking jobs

Moguldom: How did you get into the transportation industry?

Pierre Laguerre: I was born and raised in Haiti. I came here when I was 15. When I was a kid in Haiti, I always wanted to be a neurologist. It was the picture I had in mind for America. However, living in one of the roughest areas of Brooklyn at the time and seeing the gang banging, drug dealing and murder, I wanted a way out. I wanted to escape.

After I graduated high school, my uncle took me on a cruise and it changed my entire perception of the world. I was like, “Oh man. The world does not revolve just around this tiny community. There’s much more outside of the world.” From then on, I really was trying to find a way to get an exit.

It looked like trucking was the most promising way for me. I dropped out of college and became a truck driver. I was able to drive across the country and get out of the neighborhood. I was making about $90,000 a year. I started looking at how to become an entrepreneur, especially in transportation logistics.

Moguldom: How long were you driving before you started your first company?

Pierre Laguerre: I drove for years. I even went on to become an owner-operator for about two years. I failed at that because of an accident and hurt my back. I lost everything in 11 months. I started a window cleaning business in New York and then went right back into trucking again. I built a trucking staffing company, Mac Transport Staffing. It made about $2 million in revenue within two years. I then built another trucking company, JP&L Transportation, where I owned around 11 trucks. It had $1.2 million in revenue within its first year. And even still throughout this time, I was still driving trucks myself.

“While my son was in a hospital down the street, I was laid up in another
one. I said, ‘God, if this kid can fight at 3 months old, there’s no way I’m giving up.
Just give me a second chance to walk out of here alive. I will build another business. I will add a team, I’ll add technology to build a sustainable, successful company.’ This is why Fleeting exists today.” — Pierre Laguerre, founder and CEO of Fleeting, a mobile platform that connects commercial drivers with on-demand trucking jobs. Photo: LinkedIn

Moguldom: Are both companies still in operation today?

Pierre Laguerre: No. I was running both of those companies simultaneously by myself. I didn’t have a team I could trust to delegate and I felt the burnout. Then I had my son who was born with Down syndrome. He went through multiple surgeries. It was very painful seeing him go through it all. It felt like my world started coming down around me. It started affecting my business. My businesses were falling apart.

One night I was carjacked and I had my skull cracked. It left me in the hospital. I had 67 staples in my head and a titanium plate in my forehead. While my son was in a hospital down the street, I was laid up in another one. What kept me alive was seeing my son fighting for his life at 3 months old. And I said, “God if this kid can fight at 3 months old, there’s no way I’m giving up.” I said, “Just give me a second chance to walk out of here alive. I will build another business. I will add a team, I’ll add technology to build a sustainable, successful company,” and this is why Fleeting exists today.

Moguldom: Beyond overcoming your personal tragedy and closing your other businesses, what are some lessons learned from the challenges in starting Fleeting, your third company?

Pierre Laguerre: For me, it was first understanding the entire landscape or the ecosystem of venture capital while running a tech startup. I’m used to running my own company and doing things in a typical logistics manner because that’s what I’ve known. That’s what I’ve been doing. But now when you come into the realm of tech startups, it’s a different dynamic. There’s a different culture, it’s a different game.

I’m used to running my own company and doing things in a typical logistics manner. But when you come into the realm of tech startups, it’s a different dynamic. There’s a different culture. It’s a different game.

Pierre Laguerre, founder and CEO of Fleeting, a mobile platform that connects commercial drivers with on-demand trucking jobs

For me it was finding a way to adapt to the industry, understanding the lingo, understanding how to raise venture capital, how to present yourself, your story and your numbers. I think that was the biggest challenge.

But other than that, as far as building the business, I always knew there are challenges building a business, but I didn’t expect to have that much challenge and pushback from a group of people outside the logistics industry. They would say, “Oh no, this idea won’t work because your market is not big enough.” I learned how to really focus more on what matters the most, which is a paying customer. So I’m focusing on the customers and the drivers and the people that we’re serving. And this is why we really started growing.

Within seven months of launching, we’re doing $500K annual revenue, $1.7 million in GMV and we are pretty much growing at 30-percent month-over-month. It’s because I focused on what matters the most building a business, and not anyone telling me that I need to prove X, Y and Z before they can invest in my company.

Moguldom: Besides knowing the industry, is there anything in particular that helped you to see revenue in the first year of starting your first tech startup?

Pierre Laguerre: I think knowing the space, doing the research to understand what pain the customers have right now. What is the pain that a driver or a company has right now? In my head, it’s like, “OK, how much are you willing to pay to make that pain go away?” Once I started looking at it that way, I started to really dig in. We started approaching it that way. 

Our customers didn’t like the fact that they’re paying expensive insurance on trucks that are just sitting there not being utilized. So, they use us to fully maximize those trucks. Trucking companies can’t hire and retain truck drivers and they’re spending a lot of money to hire them. We actually help them solve that problem through our technology by helping them find drivers on-demand to keep their truck operating.

Also, I think having a team that understood the pain, as well as the field, helped us to be more in tune with the need. It became a lot easier for me to step out of sales and really focus on fundraising. I think that’s what helped us to raise capital — the fact the team support is there. To be able to go out and raise capital and still put up big numbers is very interesting and not something I think could do by myself. A big shout-out to my team. I appreciate it.

Within seven months of launching, we’re doing $500K annual revenue, $1.7 million in GMV and we are pretty much growing at 30-percent month-over-month. It’s because I focused on what matters the most building a business, and not anyone telling me that I need to prove X, Y and Z before they can invest in my company.

Pierre Laguerre, founder and CEO of Fleeting, a mobile platform that connects commercial drivers with on-demand trucking jobs

Moguldom: Have you raised any money thus far?

Pierre Laguerre: We’ve raised a total of $500,000. We’ve raised from investors like Quake Capital, Arlan Hamilton, also Chamillionaire, E40 and we have a few angels on the cap table as well on our raise.

Moguldom: When you had your other two businesses you were doing it all by yourself. This time around, how did you go about picking your team?

Pierre Laguerre: The team part was very important to me. I said I wasn’t going to build another business again by myself. I needed a team. But coming into the venture game, I see how important the team was because that’s something that the investors really pressed on. I was able to build a team of five of us working full-time on Fleeting through networking. We have Paul, our COO. Paul has a commercial lending background. We have Benny, head of sales. Benny also was the former COO at Freightstar. We have our CTO, O’Neil, who is also the former CTO of a company called AirWatch which was acquired by VMware for over $ 1billion. And we have Ryan who is focused on the UX design.

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For me, the team is very important. I really did spend a lot of time meeting a lot of people. I won a lot of pitch competitions as well which I think also made it a lot easier to network with people. I was very open with my strengths and my weakness and what I was looking for in a company. We really have a very strong team I’m very proud of.

Moguldom: What do the next five years look like for Fleeting?

Pierre Laguerre: The next five years look very interesting. We’re very optimistic about the future. In the next five years, we really want to change the stigma of working in transportation logistics. We want to make it a little bit more appealing to bring more millennials, LGBTQ communities, and other marginalized people to understand how important trucking is and that they can make a lot of money on their own terms. These are the things that in five years we look to be pioneering and leading a new generation in trucking.

Our customers didn’t like the fact that they’re paying expensive insurance on trucks that are just sitting there not being utilized. So, they use us to fully maximize those trucks. We help them solve that problem through our technology by helping them find drivers on-demand to keep their truck operating.

Pierre Laguerre, founder and CEO of Fleeting, a mobile platform that connects commercial drivers with on-demand trucking jobs

According to the American Trucking Association, the industry will be short 100,000 truckers by 2024 and that’s a huge problem that can affect every American citizen.

Moguldom: Do you see autonomous driving affecting your industry at all?

Pierre Laguerre: Not at all. We have to be very careful when we talk about autonomous because it creates all this fear and worry. We probably won’t even see it in our lifetime because, in order for that to happen, our entire infrastructure needs to be changed. Our entire infrastructure cannot sustain autonomous trucks let alone cars right now. We have to also look at regulation. Insurance companies are saying, “OK well who’s going to insure this thing?”

They are still another 50, 60 years away from autonomous for trucking. But there is one thing I can see working and it’s called the “platooning model.” It is where one driver is driving the truck and they’ll probably have three or four trucks behind, following the first driver. But the three or four trucks behind won’t have any drivers in them. The first driver will be leading all three trucks. What will happen is when that truck gets to the final mile, you need three drivers at a ramp to jump in each truck to go do the final-mile delivery. Even then, for Fleeting, we see ourselves being in the center as the main company that provides drivers.

Either way, Fleeting will still be a pioneer in the space. We’re not worried about autonomy. Also, one of the largest companies that was leading autonomous trucks is now looking for a buyer. They’re looking to sell the company because they can’t raise capital. I don’t think people should really get too hung up on worrying about autonomous right now. We have a long way to go.