From: myfirstmillionpod
Jesse Itzler is a highly successful entrepreneur known for starting multiple companies across diverse industries. He is also recognized for his fitness achievements, motivational speaking, and “will versus can” philosophy [08:49:99]. Itzler emphasizes that his successes have often come from opportunities that presented themselves rather than meticulously planned business ventures [23:53:99].
Early Ventures: From Rapper to Jingle Mogul
Itzler grew up in New York during the 1980s when rap and hip-hop were emerging [03:59:47]. Initially, he pursued a career as a rapper, signing with Delicious Vinyl, but was dropped shortly after [04:27:66]. This setback led him to pivot into writing jingles and theme songs for companies and sports teams [04:45:99].
During this early period, Itzler was living in New York, often sleeping on friends’ couches [05:08:99]. He faced a dilemma when a music manager offered him $10,000 for 10% of everything he would ever make, essentially owning a portion of his future earnings [05:12:00]. At the time, needing money to fund studio production, he was inclined to accept the deal [06:00:99]. However, a friend’s father, Lou Katz—a successful entrepreneur and second-largest shareholder of the New York Yankees—advised him against it [07:03:00]. Katz famously asked, “Will you make this business work without the 10 grand?” emphasizing the difference between “can” and “will” [07:54:00]. This philosophy became a significant theme throughout Itzler’s life [08:49:99].
Itzler’s jingle business began with a pivotal moment: he approached the New York Knicks to write a theme song called “Don’t Back Down” [15:20:00]. The Knicks paid him 4,800 to produce, resulting in an initial financial loss [15:44:99]. Despite the loss, Itzler viewed it as a strategic investment, gaining the Knicks as a customer allowed him to leverage their name as a “calling card,” making it easier to secure deals with other professional sports teams [16:10:99]. He built a business selling CDs of these theme songs [16:30:99].
At 27, he sold this company to a public company called SFX for an initial 12-16 million [16:38:00]. After taxes, he made around $1.5 million from the initial sale [17:03:00]. However, due to overspending and an immature relationship with money, he eventually lost most of his initial earnings [18:41:00].
Marquee Jets and the “Jet Card” Concept
With the same business partner, Itzler co-founded Marquee Jets in the late 1990s [23:38:99]. The idea for Marquee Jets arose when Itzler was a guest on a private jet and realized the potential for a new service model [23:53:99]. At the time, private air travel options were limited: either buying an expensive private jet ($50 million) or committing to a fractional ownership program like NetJets, which required significant capital and a five-year commitment [24:27:00]. Chartering also presented uncertainties regarding plane ownership and reliability [24:55:00].
Itzler identified a “white space” in the market for individuals who wanted private jet access for around 25 hours a year without the responsibilities of ownership [25:02:99]. Their solution was the “jet card”—a 25-hour pre-paid card that worked like a debit card for private jet travel [25:19:00].
To execute this, they needed planes. Their strategy was to partner with NetJets [25:29:99]. The initial meeting with NetJets’ president, Rich Santulli, resulted in them being kicked out after only 12 minutes [26:41:99]. However, their persistence paid off. Itzler had previously helped a man whose daughter wanted to be a backup singer at a famous singer’s concert; this man, Jim Jacobs, turned out to be the president of NetJets [27:26:99]. Jim Jacobs gave them another chance.
For their second meeting, instead of a traditional PowerPoint presentation, Itzler and his partner brought in their own “focus group” of eight potential clients [28:57:99]. These individuals, including Carl Banks from the New York Giants and Run from Run DMC [29:43:99], explained why they would buy a 25-hour jet card but not a fractional ownership. This live demonstration proved more impactful than any chart [29:09:99]. Santulli saw their enthusiasm and was willing to “bet on these two guys” [30:16:99]. They also identified a younger demographic of athletes, entertainers, and “young moguls” who could become lifetime customers [31:14:00].
Marquee Jets started by leasing time on NetJets’ planes, which meant NetJets carried the inventory risk [35:56:00]. Marquee Jets acted primarily as a marketing organization, marking up the hours they leased [36:15:99]. In their first year, they generated nearly 235,000 to 1 billion in annual revenue, their model shifted to requiring them to purchase airplanes [36:24:99]. Itzler notes that this partnership was incredibly fruitful, leading to NetJets acquiring Marquee Jets [32:50:00]. NetJets itself was later sold to Berkshire Hathaway [02:56:99].
Itzler admits he was a “terrible operator” and “terrible manager,” but excelled at sales and creating talk-worthy opportunities [35:02:99]. They hired a CEO early on, allowing him to focus on sales [35:09:00]. A key strategy for acquiring their first customers was targeting high-profile individuals to establish credibility [39:00:99].
Itzler found his first Marquee Jets customer, Josh Koppelman (who later became a famous VC), by strategically buying all the muffins from a coffee shop at a TED conference in Monterey, California [40:32:00]. When Koppelman tried to buy a muffin and found none, Itzler offered him an “extra” one, initiating a conversation that led to the first sale [41:01:99]. Itzler then “serviced the hell out of him,” going above and beyond by providing services like a list of pediatricians for his kids in Mexico or making dinner reservations for him [42:11:00]. This exceptional service led to Koppelman giving him a referral, a strategy Itzler repeated for five years to grow the business [42:47:00].
Itzler also met his wife, Spanx founder Sara Blakely, through Marquee Jets, as she was a customer [38:17:99].
Zico Coconut Water
Itzler continued his pattern of identifying niche markets when he ventured into Zico Coconut Water [45:29:00]. His interest stemmed from researching hydration for a 100-mile race, where he discovered coconut water and used it to power his 22-hour and 30-minute finish [46:20:00]. Convinced it was the “new Gatorade” and a better, all-natural option, he spent a year trying to figure out how to import it but couldn’t [46:52:99].
Employing the same partnership model from Marquee Jets, Itzler approached Coca-Cola with the idea [47:27:00]. The president of Coke’s emerging brands division, a friend of a Marquee Jets customer, agreed to a meeting [47:30:00]. When Coke expressed interest only in buying existing brands, not PowerPoints, Itzler partnered with Zico [47:50:00].
During a challenging meeting with Coke, Itzler impulsively mentioned that actor Matt Damon was his partner [48:50:00]. Damon, also a Marquee Jets customer, had expressed interest in getting involved in Itzler’s coconut water venture [48:15:99]. Itzler called Damon and asked him to film a 35-second video of himself getting a coconut, chopping it open, and saying, “There’s got to be a better way than this,” which ultimately secured the deal with Coke [49:15:99]. Coca-Cola eventually bought Zico outright two years later [50:23:00].
Current Ventures and Philosophy
Itzler’s approach to entrepreneurship involves continuously seeking new opportunities and often leveraging partnerships. He is currently exploring the pickle market, noting that 75% of Americans eat pickles, yet there’s a lack of innovation and strong branding in the category [56:55:00]. He sees it as a “marketing problem” he can solve [58:27:00].
He also conceptualized “Quickies”—ready-made, eight-ounce alcoholic shots that could be sold at liquor store countertops, similar to Five Hour Energy’s impulse buy strategy [01:02:45]. He even suggested a strategy of consolidating liquor store countertop space for advertising, then selling that space to large brands like Nabisco [01:03:55].
Now 55, Itzler emphasizes that “more isn’t better; better is better” [01:02:00]. He prioritizes maintaining his health, family, and friendships over solely chasing financial returns [01:11:00]. He often says “no” to high-aggravation projects, even if they offer high rewards [01:51:00]. An example of this was his idea eight years ago to make commercial travel feel like private travel, allowing passengers to pay extra for back-door access to planes and a more seamless experience [01:53:00]. While lucrative, he decided against pursuing it due to the potential energy drain [01:07:00].
Itzler uses a “big-ass calendar” to plan his year, including races, speaking engagements, and family travel [01:04:45]. He has several personal philosophies:
- Musogi: Inspired by an old Japanese ritual, Itzler’s interpretation means undertaking one “big year-defining thing” annually, which should have a tangible outcome [01:18:50]. Examples include his bike ride across America, living with David Goggins, or starting a new company [01:18:41].
- Kevin’s Rule: Named after a friend, this rule involves doing something he normally wouldn’t every other weekend [01:37:00]. This creates mini-adventures throughout the year and enriches life experiences [01:20:12].
- Three-Minute Daily Networking: Itzler advocates spending three minutes a day sending texts or emails to “compliment, congratulate, or console” friends, suppliers, or colleagues [01:11:30]. This simple practice helps build and maintain authentic relationships and creates “permission slips” for future interactions [01:13:31]. He also prefers handwritten letters for their strong impact [01:15:47].
Itzler believes that the feeling of selling a business is the same as finishing a marathon, walking an old lady across the street, or any other action that makes one feel good about themselves [01:08:32]. He emphasizes not getting lost in the “hustle and grind” culture at the expense of family, health, and friendships [01:22:50].