The Richest Guy in the Sky

Leadership rule #1: Believe in people. They'll never forget.

Jared Rosenthal
Published on

"Let's GOOOOO!!!", I yelled back at my kids, freezing, running, and rolling luggage through the potholed long term parking lot at La Guardia. I had just snagged the only spot left in the furthest row from the terminal, but finding it cost me 15 minutes, and I didn't exactly budget the extra time. Only an hour left until takeoff.

"Why didn't I wake up earlier," I thought. "Ah, it's only the Friday before a holiday weekend, not to mention the day before mid-winter break for NYC schools - it won't be that busy."

Already dressed for Florida, I was just about frozen when I swung through the revolving door to the JetBlue terminal. And there it was: the longest security line I have ever seen. Ever. I couldn't even see where it ended. And I still had to check my bag, get boarding passes...

I scrambled to find the right line: was it "Bag Drop only"? Was it "Full Service International"? Neither seemed right. I turned to the JetBlue employee guarding the entrance to the full service line to ask, and he just looked me dead in the eyes. Before I could get a word out, he said my name. "Jared Rosenthal".

"Wally!" Next thing I knew, I was hugging a guy who worked for me more than 10 years ago out on the streets of Washington Heights. He was a marketing rep on my first street marketing team - my first RV. It was the team that helped me pioneer a strategy that would eventually turn into 20 more teams on 20 more RVs in New York, and then another 20 more teams and trucks across the country. In fact, it was the model that I ultimately used to start my own company on an RV, the Who's Your Daddy truck that landed me my own reality show, Swab Stories.

"Man, you look great! How have you been? You work here?" We caught up quickly as he ushered me to the front of the bag drop, passing several families who were already waiting. The memories from that time of my life flooded into my head, but I had to make my way to the gate, so we parted ways quick and I left him to his job working the check-in line. As I walked towards security, I whispered to Sophie and Levi, "You see what happens when you treat people well? They don't forget. I was his boss before you were born. And I haven't seen him since. Yet he still hooked us up all these years later."

I turned a corner and my jaw dropped. I finally saw how long the line actually was. Massive, packed, and not moving at all. My stomach started to churn. We would never make this flight. Just then, I felt a hand on my shoulder.

Wally looked at the TSA guard and told her, "They're with me". Before I knew what was happening, we had passed hundreds and hundreds of waiting travelers and proceeded directly to the checkpoint, the one that's right before you start to unpack your laptop. Another TSA agent on guard. Wally instructed us to give her our documents. She immediately stopped what she was doing and checked us through. And then, we came upon the smaller yet still sizable and entirely shoeless and belt-less line. You know, the one where it seems you are so close, but it still takes another 15 minutes.

Wally had recently immigrated to the United States from the Dominican Republic when I first hired him. The Washington Heights RV was a team of ten bilingual people, mostly of Dominican descent, mostly in their early 20s, working in a Dominican neighborhood offering healthcare services to uninsured residents. We could have put the first RV anywhere, but the energy of the Heights always motivated me. The smell of the Spanish food, the beauty of the architecture and views of the rivers, and the knowledge that my father grew up on those same streets when it was an altogether different place, yet the same. It was a perfect spot to unleash my imagination and to test and perfect my marketing strategy.

We followed Wally directly to the spot where you put your bags in the X-ray machine, past people who presumably had waited over an hour or more by now. This time, it really felt like we were doing something so wrong, but yet so right. Sophie leaned over and confided, "Some lady just mumbled, who the f--k are they?" I was poking Levi in the ribs to make sure he understood how cool this was. We literally cut off the person who was about to go through the metal detector when Wally told him to step aside and wait.

It took about a year in the Heights to figure out how to make the RV thing work, and then I replicated it over and over again, in dozens of other neighborhoods across NYC - Chinatown, Harlem, Jamaica, Flatbush, Brighton Beach, the South Bronx. Each time, I took local people who spoke the language and knew the culture and put them to work in their communities. It didn't matter if it was a Russian, West Indian, African-American, or any other neighborhood. The strategy worked, and the company took off like wildfire. We multiplied our membership five times over in four years. We outpaced the competition. We got noticed, and we got copied by virtually every competitor in the space. Well, at least they copied what they thought was the secret to our success - the RVs themselves. But that really wasn't it at all - that was just the vehicle. The real secret was so simple and yet so effective.

Believe in people.

I realized something very early into my management role. People hate management. They don't trust us. They've been told a thousand lies already. They look around and see evidence that the things you are telling them are not true, and they're not ever going to be true. It's hard to sell people on a vision of growth, especially if in the history of the company, it has not provided any growth to them personally, or to their colleagues in similar roles, even if the company has thrived. But the opposite is also true. If you can point to a few examples where the vision you are laying out has tangibly altered the fortunes of real workers that other staff can relate to, it can be the catalyst for an electrically charged atmosphere.

Why? Simple. It's one thing if me, as the VP or whatever, says, "Work hard to make us grow, and then you will grow! I promise!" It's a whole other thing to say, "Look what happened to Fernando, someone who went to the same high school as many of you, someone who grew up in the housing projects. He became the top rep, and now he manages an RV and ten reps in Brooklyn". Or, "Khadija was fresh off the plane from Africa, braiding hair because it was the only job she could get; but we believed in her. She worked hard. She became a manager. And now she's a Director responsible for 4 teams." When I locked in enough of these real-life successes, something amazing happened. I no longer needed to persuade the staff of my vision. The staff persuaded each other.

By the time I got recruited away to run a different company in Chicago, to take this marketing model national, I had built the team to 400 staff. That included about 40 mid-level managers who had virtually all been promoted from within. They would stand up at meetings and say things like, "I started at the bottom just like you. I grew up just like you. I am a manager now. I am important here." The message to their colleagues was loud and clear: "YOU CAN DO IT, TOO!"

How do you manage 400 people spread out over hundreds of miles? Not by watching over everything they do, that's for sure. That's not possible even if you wanted to try it. But if the far-flung staff are self-motivated, if they actually want to grow and physically see evidence and examples that it's possible, they then try to emulate those among their colleagues who have already grown, and it's a beautiful thing. It's contagious. It's rewarding. And, don't forget this: it works.

Believe in people, and they will tend to believe in you, too. Of course, it can't be fake - they have to actually have something to appreciate. But, if you open your eyes to talent diversity, you can look beyond traditionally valued business skills. You can see how somebody's unique personality and energy can contribute to your company. Maybe it's their sense of humor, or artistic skill, or social intelligence that can open doors. If you can find that sweet spot, and then value it, and show them why you believe it makes them great and appreciated, then you will have a loyal and dedicated employee - one who has your back.

Incorporating talent diversity has sometimes meant I had to support some frustrating weaknesses in other skills. For example, I once promoted someone that had such poor grammar that his emails made me cringe. But I put it in perspective. How relevant was that particular inadequacy to the job at hand, and in relation to his amazing work ethic and his speaking skills? Just as important, what would it have done to the team if I was to go out and hire a plain vanilla outsider to manage them, even if the outsider looked way better on paper? Nothing kills morale like crushing hope with an empty suit.

Still, the cynics of the world believe that nothing is authentic. Back when I worked with Wally, one time I got up at a staff meeting and told what I thought was a great joke. The whole place erupted into laughter. It felt amazing. I remember going home that night and telling a friend of mine the story of my joke and the response to it. He asked me, incredulously, "They all work for you, though, right?"

I said, "Yeah, so what?"

"Well, they HAVE to laugh at your jokes. You're the boss!"

We got to the gate in record time. Levi sat down and watched the bags while Sophie and I went to grab coffee and snacks. In place of an extremely stressful morning, a missed flight, and a screwed up vacation, we now had the pleasure of having a few minutes to kill before boarding. I was just paying for Sophie's magazine when Levi came running over. "Dad, they're calling us!"

"OK, don't worry. We have time. We're in the back of the plane, we have to wait til they call our row."

"No, dad, I mean they actually called US. They just announced, 'Jared Rosenthal and family to the gate.'"

We hustled over, and there was Wally. "This flight is full," he said. "If you don't get on now, you'll never have room in the overhead bins for your bags." I thanked him and hugged him goodbye.

We then proceeded, alone, down the jetway and onto the plane, feeling like rock stars. I sat down in my cramped middle seat but I couldn't stop smiling. I asked Levi, "Do you know why he did this for us?".

Levi replied, "Because he worked for you?"

I said, "Well, he doesn't work for me now, it's been over a decade." And, clearly, he doesn't have to laugh at my jokes any more, either. But that didn't stop him.

I've flown first class a handful of times, and it always amazes me how well they treat me. Their smiles linger on my eyes when refilling my glass of wine, and it really seems in those moments that they authentically like me. But of course they don't - it's a rented experience. I know this because I've flown coach more times than I can remember, and mostly, they treat me like cattle. They bang the drink cart into my knees and don't apologize. They wake me up arbitrarily and don't care. I'm the same guy, they're the same flight attendants...totally different experiences.

Wally dropped everything to help us out, and in doing so he saved the day, but moreover, he unintentionally gave my kids a rare privilege to experience authenticity. This hook-up was something that money, power, or celebrity didn't buy.

So go ahead and brag about your "Even More Speed" and your "TSA Precheck". Keep sending selfies from the first class lounge, and posting status updates from that chartered jet. There's no comparison. For at least one day, last Friday, I was the richest guy in the sky.

Jared Rosenthal

Jared Rosenthal

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Read about Health Street's reality show on VH1, Swab Stories.

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