The Upside of Not Giving Up: An Interview with Fleeting’s Founder and CEO, Pierre Laguerre
Fleeting connects CDL drivers with on-demand trucking jobs. As a driver, you can make as much money as an owner-operator without owning a truck. Meanwhile, carriers can access qualified CDL drivers when they need them. For more information, visit https://www.fleetingpro.com/.
Fleeting recently won the Grand Prize at the Black New Venture Competition. Learn more about the BNVC here.
Pierre Laguerre is Fleeting’s founder and CEO.
HBS Entrepreneurship Club: Did you always want to be an entrepreneur?
Pierre Laguerre: No. I wanted to become a doctor.
HE: So what caused that shift?
PL: I was born and raised in Haiti. I moved to the US when I was 15, with the goal of being a doctor, and the picture I had of America wasn’t really where I landed. I landed in the ghetto — there was drug dealing, murdering, violence. I went from dreaming of becoming a doctor to just dreaming of staying alive. I wanted to get out of that community because I didn’t want to just become a statistic. So trucking was my way out. I became a truck driver. This is where my entrepreneurial journey started.
HE: What made you decide to take the leap to create Fleeting?
PL: I decided to drop out of college to become a truck driver. I was studying Electrical Engineering but due to financial hardship I had to drop out. The reason I really really started doing it was because my professor gave me a very strong message early on. I worked at a logistics company, and then another one called Performance Food Group, and I started doing food deliveries to the college I was going to. I was really ashamed, I didn’t want my professors or ex-classmates to see me. So I was always trying to rush, get in, get out.
One day my professor ran into me and said Pierre, what’s going on, why are you hiding? And I said I dropped out of college to become a trucker, I didn’t want to look like a loser. And he said, how much do you make in a year? I said, 90k. He said, half of these kids are gonna graduate and not be making 90k, so I want you to be powerful, own it, and become the best trucker you can be. That message really resonated with me. So a year later I purchased my own truck and became an operator. And a year later, I built my own staffing agency, and I grew that company to $4M in revenue.
Having spent that time in that space, I realized the real pain point for drivers. Having spent so much time on the road, you never have time for family. For me that also resulted in a divorce, because I was never home. And then as an owner, I saw how hard it was because drivers need days off, but as a carrier I still have a duty to deliver shipments to my customers. It was hard to find qualified drivers to do this. I had to find and pay other carriers to do this for me. So that was really painful, and it got me thinking — truckers are really looking for a company that can provide some flexibility, and trucking companies are always looking for great talent to tap into. Companies like Uber Freight, Convoy, they target a different part of the market than we do. We’re really focused on labor — giving drivers that flexibility, and giving trucking companies access 24/7.
HE: Was there a specific instance that made you decide, now is the time to start it? I think entrepreneurs frequently talk themselves out of starting their business. What made you decide, all right, I’m going to do this now?
PL: Okay. While running my own staffing agency and trucking company — I was actually running them by myself, simultaneously. So I couldn’t delegate anything. I was really starting to get burnt out. One of my sons was born with a serious condition in 2017, and he had to go for heart surgery around March 2018. At that time, I didn’t care about no business, no truck, no customers. All I cared about was my son. I needed my son to be alive. That started affecting me personally, emotionally, and obviously financially as well. And my numbers really started falling apart.
When my son went in for his second surgery in May 2018 — and this isn’t really a story I share with people, but hey, why not. This is my story. When my son was in surgery, my mother came into town to see him. I stopped in a restaurant in a dangerous community to pick up food for her, and I got mugged in that community. I got my skull cracked. I had sixty-seven stitches in my head. I was in a coma for two days — like, everything fell apart. So I’m in the hospital fighting for my life, while my son was in the hospital fighting for his life. And what gave me strength was I saw how hard my son was fighting when he was only a few months old. And I said, God, if this kid can fight this hard when he’s only a few months old, there’s no way I’m giving up. If you get me out of this hospital alive, I will build a team, I will add tech, to make sure that we build a sustainable and successful company. And by the grace of God I came out of the hospital twelve days later and just hit the ground running, and this is where Fleeting’s at now.
HE: What’s been the most difficult part of running this company?
PL: I think part of it is just the challenge of running a venture-backed company — when you’re really trying to add technology, at scale. Especially for someone like me, who comes from a non-technical background, and my entire life is in transportation and logistics — that to me was the most challenging part, trying to build a team around it and trying to convince investors in the vision we’re trying to build. I was getting a lot of no’s at first, it was hard to raise capital. What I did was I kept focusing on the product — I kept speaking to customers, kept speaking to drivers. And that gave me the confidence that absolutely there is a problem here, and there has to be a way for us to bring this solution to the market.
I kept my head down, kept speaking with investors, and luckily we started getting investments. Raising capital is very hard. For some people raising capital might be a little easier, but at the end of the day, being a tech founder, getting investments — all of it is very hard. You need to have thick skin for it. It’s really not for the faint of heart.
HE: Given that you’re not from a technical background and didn’t start out in tech, what advice would you give someone in a similar position? What did you do on a tactical level to get into that community?
PL: I had a friend who used to work at an accelerator out of Florida. We would talk all the time about my idea, and she said, you need to go to an accelerator, you need to go to an incubator. And I was like, what the hell is an accelerator? And she said that’s the best way to learn. I did a lot of research online about how to build a company. I learned about Y-combinator. I decided to look into that. I dug in and started to see the language around start-ups, the roles. I made it my business to apply to hundreds of accelerators. I went to an accelerator and that gave me an early lead to get into the tech ecosystem.
HE: Would you recommend accelerators to other founders?
PL: I definitely would, especially with certain brands that are top-class. I strongly recommend them, especially to anyone who doesn’t have that technical background or doesn’t really understand how to navigate through the landscape of raising venture capital, or go-to-market strategy, or building a team. It can be very, very helpful for that.
HE: What advice do you have for people who want to join pitch competitions, or who’ll be getting in front of investors soon?
PL: I used to join 10–15 pitch competitions a week. Early on I was the loser very frequently. I kept going, kept applying. It was about putting myself out there, getting comfortable in front of the audience, getting comfortable with the hard questions that investors usually ask after you pitch. So it got me familiar with the questions, then I would go do my homework on those questions, and make sure I had the right answer for investors, to make them comfortable about what I was building. After that I just went on this winning streak. I think ultimately that’s just coming from…how I was a failing a lot at it, in the early days, and it was very painful. But there’s a huge upside, if you don’t give up.
HE: This is the kind of company that can be present all over the country. How do you at Fleeting think about expansion? How do you decide which cities to invest in, next?
PL: There’s two ways we look at expansion. We look at where we’re getting the most downloads from drivers that are reaching out. We also understand supply chain on a strategic level, and we look at where the most freight is being moved or originating from. So for example, Atlanta has all the headquarters for all major trucking companies. So there’s a huge market opportunity here. Texas is another big market for trucking. Texas is a huge market opportunity, all by itself. Then you have the Midwest — Chicago, Indiana, this is where any frozen, perishable items are coming from.
When we think about expanding, we think about going to the areas that are most potent for transportation, the most condensed. If we can have presence in each of these markets early, it makes it a lot easier for us to expand throughout the entire country. It’s being very strategic on the key areas we expand on, and that will determine our ultimate success at the end of the day.
HE: If you think back to when you were starting the company, or maybe even before then…what’s one or two things you wish you knew back then?
PL: Understand the importance of your cap table. Understand how you allocate stocks or grant shares to your early team members, the entire structure of your company. Those are things I wish I knew earlier. They affect me in the sense of time, because there were times when I needed to close a round, and those documents weren’t where they needed to be, and that kind of dragged the round. And sometimes, it can potentially kill your round as well.
Any founder should get a great attorney early on to get everything situated, as far as making sure that the company is structured the right way, making sure the documents — especially of you owning the company, what share you’ve vested as the CEO of the company — are all in order. For early-stage founders it’s key that they get with an attorney who understands the landscape of building a tech company, the language, the structure, the things you need to know to be protected. Because at the end of the day, believe it or not, you are a founder that’s swimming with sharks — so you need those things tight.
This article was written by Isabel Yap from the Harvard Business School Entrepreneurship Club. Special thanks to Tyler Simpson of the Harvard Business School African-American Student Union for her help in preparing the article.
