Jesse Itzler’s life is about being bold and never shying away from taking risks. A former rapper turned entrepreneur, motivational speaker, and bestselling author, Itzler believes action trumps experience and you create your own luck by putting yourself in a position for luck to find you.
He says, “Luck doesn’t happen sitting at home watching the Kardashians.” Check out this clip from the 2022 Producers Club meeting, where Jesse shares an incredible story of the action he took that pushed him as an entrepreneur: MSPSuccessMagazine.com/action.
At 21 years old, he landed a record deal as a rapper (under the pseudonym Jesse James) by cold-calling a record label and hustling his way into the room. After getting dropped from his record label, he wrote a theme song for the New York Knicks that went viral and started a record label called Alphabet City Sports Records.
He and his partner wrote and produced sports team theme songs, including the NBA’s Emmy Award-winning anthem, “I Love This Game,” and collaborated on campaigns with big-name brands such as Coca-Cola and Foot Locker. They later sold the company for $16 million.
At 27 years old, with only an idea, no experience, and not enough money to get his company Marquis Jets off the ground, he convinced the largest private jet company in the world to go into business with him. He grew that company to the world’s largest prepaid private jet card company that did $5 billion in sales, which he and his partner then sold to Berkshire Hathaway/Warren Buffett.
Jesse tells a fascinating TRUE story about how he sold his company, Zico Coconut Water, to Coca-Cola.
He convinced Matt Damon to make a home video of himself, begrudgingly shaking a coconut from a tree in his backyard, then tirelessly chopping it open so his young daughter could drink from it with a straw, then sent the video to the president of Coca-Cola.
Zico Coconut Water, which Jesse co-founded, was one of 27,000 beverage companies in consideration for Coca-Cola to purchase. During a 100-mile race he ran with friends, he became so inspired by a Navy SEAL named David Goggins, who ran the race by himself, that he invited Goggins to live with him for a month. He turned that experience into a bestselling book, “Living With a SEAL: 31 Days Training With the Toughest Man on the Planet.”
Today, he is one of the top 10 speakers in the world, married to the founder of Spanx, Sara Blakely, raising four kids, and co-owner of the NBA team the Atlanta Hawks. At a recent TMT Producers Club meeting, Jesse Itzler shared his unorthodox journey of going from a kiddie pool attendant to growing a company to $5 billion in 10 years and how he pulled off his extraordinary accomplishments.
Here are 12 lessons from Jesse on how to create your own luck:
1. Build Deep, Authentic, Meaningful Relationships.
When Jesse was 22 and had no money, he sent 10 handwritten letters out every day. They were all one-way letters, meaning he didn’t expect a response. He built relationships by authentically sending messages that truly meant something to people at a time when they weren’t expecting it.
For example, he’d send a note to someone and tell them he admired the way they parented their kids and that they were an unbelievable dad. “I did three things my entire life to build deep, authentic, meaningful relationships with people in my inner circle,” Jesse said. “I complimented them. I congratulated them. And I consoled them … and a crazy thing happened. They gave me a referral. When something went wrong in my business, they stuck with me.”
2. Put Yourself On The Playing Field And Do Whatever You Can To Accelerate Your Plan.
In the beginning, a lot of Jesse’s meetings were flukes. He’d be out somewhere and see someone he’d been looking to pitch. Then he started putting himself in situations where his audience was hanging out and be ready with his elevator pitch.
When he started Marquis Jet, to get leads, he’d show up where wealthy people were hanging out. He flew to a conference called TED, but when he arrived, they wouldn’t let him in because he didn’t have the credentials. Noticing the TED audience was buying lattes and muffins from a local coffee shop during their breaks, he bought all the muffins. Offering people with credentials one of his “extra muffins” is how he made his first sale for Marquis Jet.
“I literally controlled all the muffin inventory in Monterey, California,” Jesse said. After people were told there were no muffins, Jesse stopped people as they left the coffee shop. “I’d say, ‘Sir, excuse me, I overheard, and I have an extra muffin. If you want it, I’m not going to have it.’” The first man asked Jesse what he did, and when Jesse said he owned a jet company called Marquis Jet, it turned out the man was in the market for a timeshare jet.
“When we wrote our business plan for Marquis Jet, nowhere in the business plan did it say, fly 16 hours, go to a coffee shop, and hope to land the customer,” Jesse said. “When you have a business, do whatever you can do to get there faster. That’s always been my attitude.”
3. Do The 3-Minute Miracle Every Day.
There are a lot of calls and meetings you won’t get, so you need to plant a lot of seeds. “I play the numbers game a little bit,” Jesse said. “I have something I do called the three-minute miracle where every day I write a text, DM, or email somebody. If you do it for 30 days, you’ll hit a hundred people. If you do it for a year, you’ll hit a thousand people. Not everyone’s going to be your customer or best friend, but in the beginning, you need one person, one referral, one thing.”
4. Optimize Your Time.
After living in a monastery with eight monks, the biggest change for Jesse was his relationship with time. He explained that often when we think of relationships, we think of people such as our relationship with our kids, our spouse, or our parents. But Jesse challenged the audience to think about relationships in terms of time and money.
To illustrate, Jesse asked a woman in the audience about her parents. He discovered she lives in Hawaii and her parents live in Vancouver, and she visits her 80-year-old father once every other year. “Let’s say he lives to be 90,” Jesse said. “You don’t have 10 years. You have five visits. Once you start to look at life and opportunities like that, in moments and not time, you get a fundamental shift in how you want to spend your time and who you want to spend it with.”
5. Raise Your Standards.
As a dreamer, Jesse believes most people’s standards for their products and services aren’t high enough. “I believe once you have your product and most people say, ‘This is amazing!’ I immediately go to ‘How could it be 10 times better?’” Jesse said. “Everything should be at an Olympic standard. My wife just made a product. Everybody in her company loved it. They had all these people working on it for five years. They did a fit test, then she put it on. Everyone is going crazy thinking this is going to revolutionize the industry, and she said, ’No, send it back to Italy.’ The standard must be high.”
6. Never Give Self-Doubt A Voice.
When he was training for the ultramarathon, he learned to never verbalize pain or self-doubt and to build momentum through wins you create from positive self-talk. “I wouldn’t make it a spoken word, because once you say it, it becomes a reality,” he said. “When running an ultramarathon, you never say, ‘I’m struggling,’ you say, ‘I feel great!’ You start to believe your own lie in those situations, and those small wins are really important to conquer self-doubt. Start to build a little momentum around little things. Self-doubt — if you start saying I’m not good enough and actually believe it, you can’t possibly win. None of us can.”
7. Create No-Lose Situations.
Jesse doesn’t use win-win situations because while both people may win, they are not equal wins. Instead, he creates situations where there is no way the person could lose. Jesse was given the opportunity to buy four New York Yankees Legend tickets that cost $320,000 for the season at a time when he was in debt and had zero money. He had nothing to offer and was looking for something he could use to build relationships. He knew the tickets could do that for him and would pay for themselves 10 times over. He agreed to purchase the four Legend tickets, then convinced a friend to front him the money by creating a no-lose situation.
“At that point in my life, I was making negative money,” Jesse said. “I made 20 grand, and I spent $25,000 on my credit card. I called the only guy I knew who could afford the tickets and was a huge Yankees fan. I said, ‘Look, these seats are available. We’ll never have a chance for the rest of our lives to get them.
If you lend me the money, I’ll pay you back in two years with insane interest. And if I don’t, I’ll sign the seats over to you. So, you’re either going to make a lot of money or you’re going to own the best seats in sports history.’ He did the deal.
I met Jay-Z in a studio six months after I got the tickets. I knew he was a big Yankees fan. I never met him in my life. I told him about the tickets. We split the tickets and were partners in the tickets for 10 years. Two years later, I started Marquis Jet. He’s doing a world tour. He needs an airplane. We flew his entire tour on Marquis Jet. It paid for all the seats right there.”
8. Remember, Action Always Trumps Inaction.
Taking fast action on your ideas and dreams is more important than knowing how you’ll get there when you don’t have everything all figured out. When Jesse was 27 years old, he was a guest on a private airplane. Inspired, by the time he landed, he and his partner had decided to start a private jet company. By the time he was 28 years old, he and his partner co-founded Marquis Jet.
“I wanted to fly privately, except we had no airplanes, but we had an idea,” Jesse said. “Our idea was so simple. We wanted to give everyone access to their own private plane without owning it. Everybody in this room is one idea, one referral, one meeting away from changing the entire trajectory of your life. And if you have an idea and it keeps coming to the top of your brain, the universe is telling you to pay attention to it.”
9. Do Things Differently.
You don’t get a lot of chances for big opportunities. Most times, you have just one shot. You must figure out BEFORE an important meeting how you are going to stand out in a big way. Jesse landed a meeting to pitch his idea for his jet cards/Marquis Jet to NetJets, the largest private jet company in the world. But 12 minutes into showing his PowerPoint presentation to Rich Santulli, Founder of NetJets, he was thrown out of the meeting. “We leave dejected thinking where are we going to get 650 planes to start this company?” Jesse said. “The president grabs my arm and says, ‘That was unbelievable. Rich Santulli doesn’t give anybody 12 minutes. There’s something here. Come back next week and bring this thing to life.’
We realized as entrepreneurs, we’ve got to be different. We’ve got to stand out. We have to take advantage of the opportunity. We have to look for the white space. So, we brought in our own focus group. We set up a table by the boardroom table and one by one, eight people came in: Carl Banks from the New York Giants, Run from Run-D.M.C., a powerful female real estate mogul from New York.
One by one, they stood up and said they would never buy a fraction of a plane, which is what NetJets was selling, but they would buy a 25-hour jet card. By the end of the meeting, Rich Santulli said, ‘I’m going to give you guys a shot.’ A year later, we were bigger than NetJets. We did $5 billion in sales cumulatively, and we sold that company to Warren Buffett.”
Don’t Negotiate Your Goals. You must have a do-whatever-it-takes attitude and relentlessly chase your goal all the way to the finish line. When trying to get Marquis Jet off the ground, he got a notification that Matt Damon, Jennifer Lopez, and Ben Affleck wanted to fly from Los Angeles to the Sundance Film Festival in Utah. He wanted to demo his product.
If they liked it, they would buy a jet card for $100,000 each. In order to pitch and close the entertainers in person, he told them he was going to Sundance, too, so he could get on the flight with them. But when he didn’t get to pitch them on the plane, he didn’t let up on his goal. He continued to pursue them at the event, even convincing a gatekeeper to let him in the room at a VIP event.
“We get to 41,000 feet,” Jesse said. “I come out and I start pitching Matt Damon on this idea. He says, ‘Look man, this sounds like a really cool idea, and I’m actually interested in this, but I’ve got to get ready for our Project Greenlight event tonight. We’re having this small, intimate gathering, and if you’re not doing anything, come by. There won’t be that many people there, and we could talk about your product and program there. I’d love to learn more.’”
Jesse hadn’t planned to go to the film festival, so he had no clothes and no hotel room. When they landed, he checked into a Motel 6, bought an outfit at the Gap, then headed to the event. “It’s not an intimate affair,” Jesse said. “There are 4,000 people trying to get through one guy with a clipboard. And I know I’m not on the list, but I also know I don’t negotiate my goals. When we have a goal, it’s unwavering. The plot might change. The script might change. But the goal, we don’t dumb it down. I’m leaving with the sale.”
10. If You Don’t Have A Seat At The Table, Make One.
In the VIP room, he sees the table next to Matt Damon’s has Pauly Shore’s name on it, so he gets rid of Pauly Shore’s nametag and gets a new nametag and writes Jesse Itzler on it. “If you don’t have a seat at the table, you make one,” Jesse said. “That’s how it works. We’ve got to create our own seat. Matt comes in. I start talking to him. I start pitching him. It’s too loud. I can’t hear him. I said, ‘Matt, when are you going back to L.A.?’ He says, ‘I’m going back on Sunday.’ So, I say, ‘You want to fly with me?’ He says, ‘Yes.’”
11. Put Pressure On Your Shoulders.
Success comes from learning how to be comfortable with being uncomfortable and putting pressure on yourself. When Jesse was trying to close Matt Damon, Jennifer Lopez, and Ben Affleck, he risked his entire marketing spend for the whole year to pay for the private jet to fly Matt Damon back to L.A. from the Sundance Film Festival because, as he told his partner, “That’s all the credibility we need for a lifetime.”
He adds, “We went back and forth discussing whether we should bet our marketing money on this flight, and we decided to do it,” Jesse said. “But it comes with all this pressure. He puts all this pressure on my shoulders. Let me tell everybody, pressure is a privilege. As leaders and entrepreneurs, we play for pressure. Behind the wall of pressure is where the gold is. Pressure weeds everybody else out in the space. If you don’t have enough pressure, put some pressure on your shoulders. As a 27-year-old kid, I wanted that pressure. And by the time we landed, I signed all three of them up.”
12. Don’t Limit Yourself.
Thinking big is about your mentality. It will shape the way you make decisions and the way you do things. It can motivate you, attract the right people and opportunities, and lure you out of your comfort zone. After asking his wife to look at his business plan for a coaching program, Jesse realized he wasn’t thinking big enough, so he ripped up his plan and came up with a new one. “I said, ‘This could be a $20 million business.’” “My wife said, ‘Shame on you.’ That was her reaction.
And I said, ‘What do you mean?’ She replied, ‘Why would you limit yourself to $20 million? You just set a limit.’ And I said, ‘You’re right.’ I got my team back together, and I said, ‘Show me how this could be a $50 or $100 million company.’”
Be like Jesse. Reach for peak performance by overcoming self-doubt and pushing past your self-imposed limitations. Have the courage to put yourself out there even when it’s foreign or scary and do things that make you feel proud of yourself. When you do, you’ll create your own luck. “We’ve been wired to think success is the outcome of our journey,” Jesse said. “What I’m most proud of in my backstories is that I put myself in a situation on the field. Sometimes it works out. Sometimes it doesn’t, but I’m proud. And I’m proud I put myself in a position, despite the fear, despite not having it all figured out or being the best on the field. If you want to do exceptional things, you have to put yourself in exceptional situations. Period.”
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