Professional entrepreneur and amateur paleontologist aren’t two jobs usually associated with one another. Even rarer is finding someone who is both, which stands to reason. One job focuses on the future. The other on the past.
But don’t tell that to Jeff Cripe, co-founder of Cargo, which is as 21st century a company as you’ll find. Started in 2016, the startup sells snacks, drinks, and much-needed accessories in ride-share vehicles with drivers receiving a portion of each sale. The company’s early success recently led to Cripe being named one of Forbes 30 Under 30 in Consumer Technology.
But then you find out the guy’s also an accomplished dinosaur hunter. This comes as a bit of shock, but when you (ahem) dig a little deeper the connection between these two divergent professions begins to present itself. You see, bone hounds like Cripe might be looking for proof of creatures that roamed the earth some 70 million years ago. But what they really want to discover is something new, something humans have never seen before.
That’s just what Cripe did as a teenager at the Webb School in Claremont, California, the only high school with an accredited museum of paleontology on campus. During a summer trip to Utah, he found a huge collection of fossils that included a new specimen of Teratophoneus, a close relative of the T. Rex. The area he discovered is now called the Cripe Site in scientific circles.
Not bad for a high schooler, but Cripe didn’t stop there. After Webb, he moved on to Yale before starting a successful e-commerce and retail career that inevitably led him to create Cargo. Here he discusses the early lessons that made him the businessman he is today, his advice for entrepreneurs and how he stays energized in the face of constant travel and work.
Lots of times when you speak to an entrepreneur they’ll tell you about a little business they started as a kid that got them going on their path in life. Even if it failed—and they often did—the boy or girl caught the bug and never lost it. For Cripe, it all started with a company he wanted to start when he was a kid, but never did. Still, even though it was only a dream, the thought of it continues to influence him today.
“Back when we still used CD-ROMs my parents got me business planning software as a birthday gift,” he remembers. “Ultimately, I didn’t start the business I wanted to in high school, but looking back it was important to have that early vote of confidence from people who loved me, saw potential, and made me believe it was possible.”
With that confidence instilled in him, he turned his attention away from his computer and to dinosaurs. He joined a team of students and professional paleontologists on a summer expedition to Utah and Montana to hunt for fossils and fell in love with the research and the science of paleontology. Though he didn’t make it a profession, he did learn a lesson that still serves him well today.
“When I first went out into the field, one of the more experienced people on the team told me that in Utah there is so much ground to cover, the person who hikes the fastest and the farthest will find the most fossils,” he says. “Like anything else in life, and especially at a startup, you are rewarded for putting in the work.”
This ability to put his nose to grindstone would serve Cripe well in his next pursuit: getting an undergrad degree from the prestigious and rigorous Yale University. Again, business wasn’t the focus of his academic pursuits—he instead studied humanities—but what he did learn about the seminal subjects of writing, reading, orating, art and philosophy have played a big role in his career.
“So much of leadership is about effectively communicating and inspiring your colleagues. I don’t draw on the coursework itself every day, but a traditional liberal arts education teaches you how to be a better and more persuasive communicator,” he discloses. “Those soft skills show up in my management style, my approach to investor relations and raising capital, and our partnership discussions with brands and rideshare companies.”
After school, Cripe went to Christie’s, the world’s leading auction house, to help found the e-commerce division. Again, going to a company that’s over 250 years old and bringing them into the modern age was a bit like finding a dinosaur no one had ever seen before—a mix of old and new. Using Christie’s age-old model but applying modern retail techniques, Cripe and his team succeeded in keeping Christie’s current customers while also bringing in new business.
“We found that there is a new, younger class of client who is now coming into significant wealth and is more comfortable transacting online sight unseen, because they were raised with the internet and have built more online consumption habits,” he says. This ability to look at a current situation and improve upon it would serve him well as he finally started his own business—just like the one he’d been dreaming about when he was a teenager.
THE DREAM AND THE TEAM
Even though all the way back in high school Cripe wanted to start a company, had built a startup with another company at Christie’s, and was a part of Birchbox during a hypergrowth mode, he still wasn’t sure he was ready to fly.
“Starting a company is like jumping off a cliff and trying to build a plane on your way down,” he says. “You never feel completely ready or prepared.” By taking the chance on his himself and his idea he quickly found out that what makes you successful is relying on your background and research to succeed.
“With my experience, an acceptance to TechStars, one of the top tech accelerator programs, and some early pilot data, I felt I had significantly de-risked the opportunity and was ready to take the plunge with my co-founder,” he explains.
Part of that de-risking came from understanding the market and what customers were looking for—even if they didn’t know yet. In this way, he says it’s important that your business has a benefit for both the vendor and the consumer—which is exactly what he created with Cargo.
“Early on we rigorously tested Cargo in New York City and Detroit to identify optimal product-market fit. We’ve been successful at driving demand and press coverage because we crafted Cargo to appeal and generate value for drivers and riders,” he points out. “It’s much easier to sell and drive demand for something you know people want, and Cargo was and is a win-win.”
Once he got the ball rolling at Cargo, Cripe still had a lot to learn, such as how to be a boss and how to become a leader who could inspire the people around him. One of the first lessons he learned is to share the workload.
“I strongly recommend having a co-founder,” he advises. “The data is there: success rates for multi-founder companies are much higher than for solo founder. But, beyond that, startups are a big emotional burden and you need someone to share that with.” He adds that having a partner/partners also makes work more fun. “I love my team,” he adds.
This idea of a team is big with Cripe, a huge NBA fan who often listens to hoops podcasts. He especially enjoys the talks with coaches like David Thorpe, whose concept that leadership is ultimately about inspiring the hearts and minds of your teammates made an impact with Cripe.
“I’ve really found this to be true,” Cripe reveals. “As I’ve handed off some operations to key teammates as we have grown, my role has become principally about communicating vision and setting strategy, inspiring people to hit ambitious goals, and equipping them with the tools and talent to get there, and then getting out of the way.”
Even as Cargo is Cripe’s baby, this type of leadership makes everyone invested in the company and responsible for its wins and losses. “I love knowing that my team and I are in control of our own destiny, and nothing will motivate you more than that to get out of bed in the morning and put in the hours,” he asserts. “But it also means that you take the successes and the failures very personally which can be draining.”
There’s a reason they call it running a business. Because successful or otherwise, it takes a lot out of you. With Cargo already supplying 20,000 drivers in nine cities—with more to come—Cripe stays concentrated and fit by working out in the morning before work.
“It gives me more energy, focus, confidence, and helps me sleep better,” he says. “I try to keep that firmly in my routine, but otherwise I am pretty flexible because my schedule is demanding and dynamic with around 100 days of travel annually.”
Even with all the demands he places on himself, Cripe’s been around the block enough times to know that having your foot on the gas all day every day isn’t productive. “Free time is important. It’s a little neurotic, but I started scheduling it so I wouldn’t feel like I could schedule over it as my days filled up with meetings, calls, or time set aside for work,” he says.
On weekends he only does a few hours of work per day—just enough so he’s prepared for the upcoming week. This is not only good for him but also his employees. “It gives me some time to unwind and forces me to stay disciplined about letting my team have their weekends too, rather than filling their inboxes up with my emails,” he explains.
Since Cargo is growing into new markets, sometimes Cripe doesn’t have the option to not be on the go around the clock or over the weekend so he has to find breaks when he can. “I try to keep most of my domestic travel short and sweet,” he says. “But occasionally for international travel, I’ll schedule it adjacent to a weekend so I can pop down a day early or stay a day late to do a bit of tourism.”
When he does get some downtime he still likes to keep active by playing golf. He’s often with his fiancée in Los Angeles, where they walk their dog in parks and go on hikes. Cripe is also an avid ping pong player. “I play a lot with friends and I even have a coach who I play with a few times per month,” he adds. Add in the fact that he’s gotten quite a few of the Cargo team into this old school game and you get the feeling that he’s on to something new and exciting—and it wouldn’t be the first time.