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My First MillionJesse Itzler's Exact Playbook For Creating HIT AFTER HIT (#504)
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CHAPTERS
- 0:00 – 5:08
From Rapper to Jingle Writer
Shaan introduces Jesse's background, and Jesse explains how he grew up wanting to make a rap record, got dropped from his label, and pivoted to writing jingles and sports team theme songs.
- •Jesse skipped resumes in college to make a rap record
- •He signed with Delicious Vinyl after other labels passed, then got dropped
- •He pivoted to jingles and sports theme songs
- •Shaan notes he later lived with David Goggins for 30 days, per his book
- 5:08 – 11:17
$10K for 10% of Your Life: Can vs. Will
Broke and sleeping on couches, Jesse was offered $10,000 for 10% of everything he'd make. Lou Katz, a friend's father, told him to turn it down and drove home the difference between 'can' and 'will.'
- •A manager offered $10K for 10% of his lifetime earnings
- •Lou Katz asked 'will you,' not 'can you,' make it work
- •Jesse applies will vs. can to the Ultraman race
- •Shaan and the hosts adopt the will-vs.-can framing in daily life
- 11:17 – 14:21
Coach K's Fantasy Camp and Staying Young
Shaan shares a story about his roommate driving the shuttle at Coach K's Fantasy Camp and receiving a tip from Jesse that helped fund a business idea. Jesse explains why he has attended for 18 years.
- •Shaan's roommate volunteered as a shuttle driver at the camp
- •Jesse's $100 tip helped pay for a chef's flight
- •Jesse goes to meet people and feel like an eight-year-old again
- •The hosts joke that he lives like a kid year-round
- 14:21 – 20:58
The Knicks Theme Song and Selling the Jingle Company
Jesse describes going from jingles to the Knicks theme song, which cost him more to produce than the Knicks paid, but opened the door to other teams. He sold the company at 27 and describes losing the money because he had no relationship with it.
- •The Knicks paid $4,000 for a song that cost $4,800 to make
- •Landing the Knicks made other team sales easy
- •He sold to SFX for $4 million plus an earn-out
- •He had no relationship with money and lost it through overspending
- •Sam notes young founders after an exit often have no one to teach them
- 20:58 – 23:30
Underdog Mentality After the First Exit
Asked about his inner conversation after the first success, Jesse recalls the many failed ventures behind it and says he never wants to lose his underdog drive.
- •Friends on Wall Street made it easy to compare himself to others
- •He lists failed ventures including door-to-door sales and a T-shirt company
- •Everyone told him he couldn't do it, which fueled him
- •He still considers himself back of the pack
- 23:30 – 34:38
Marquis Jet: Pitching NetJets
Jesse explains how he found the jet card idea after riding on a private jet as a guest. A favor for a singer's fan led to a meeting with NetJets, where the pair were thrown out after 12 minutes and then won them over with a live focus group.
- •The 25-hour jet card filled a gap between buying, fractional ownership and chartering
- •A past favor connected him to the NetJets president
- •They were kicked out after 12 minutes, then invited back
- •A focus group of eight people replaced the PowerPoint
- •Jesse says the decision-maker bet on the founders as the business plan
- 34:38 – 38:23
Marquis Jet Economics and Role in the Business
After a sponsor break, Jesse says he was never the operator and hired a CEO. He explains the model of leasing NetJets time at a markup with no risk, scaling to roughly a billion dollars a year, and the talented team.
- •Jesse calls himself a terrible operator who focused on sales and PR
- •Marquis leased time from NetJets with no long-term lease until it sold
- •Average customer spent about $235,000 a year
- •Jesse met his wife through the company
- •Ken Austin and a strong team built a culture that attracted talent
- 38:23 – 44:57
Landing the First Customers: TED and the Muffins
Jesse explains that credibility required high-profile customers. He tells the story of buying up the muffins at a Monterey coffee shop to land Josh Kopelman as his first sale, followed by extreme service that produced referrals.
- •First sales needed credible, high-profile customers
- •He went to TED in Monterey without a credential
- •He bought all the muffins and met Josh Kopelman, his first sale
- •Serving him 30% more than expected earned a referral
- 44:57 – 51:00
ZICO Coconut Water and the Matt Damon Pitch
Shaan asks about finding niches, and Jesse explains how his ultrarunning research led him to coconut water. He partnered with ZICO and used a short film with Matt Damon to win over Coca-Cola, which bought the brand two years later.
- •Coconut water powered his 100-mile race finish
- •Coca-Cola's emerging brands head wanted an existing brand partner
- •Matt Damon, a Marquis customer, had said he might get involved
- •A short film of Damon opening a coconut helped win Coke
- •Coke bought ZICO two years later
- 51:00 – 56:19
Low Aggravation Investing and the Commercial-Travel Idea
Jesse says that at 55 he prefers better over more and avoids high-aggravation ventures. He describes the idea Sara advised him not to pursue: making commercial flying feel private.
- •He doesn't make many financial bets and rejects high aggravation for high reward
- •Sara told him a good idea isn't necessarily one to do
- •The idea was a back-door private experience on commercial flights
- •He thought he could deliver customers from his network to an airline
- •Weekly flag football mattered more than another venture
- 56:19 – 1:04:54
Pickles and the Quickies Liquor-Store Idea
Jesse explains why he sees an opportunity in pickles: wide consumption but no recognizable brands. The conversation then moves to his Quickies idea of ready-made shots at liquor store counters, which grows into renting countertops across fragmented stores.
- •75% of Americans eat pickles and he can't name three brands
- •Pickle juice has started appearing at race aid stations
- •Mount Olive does about $220 million in revenue, per Sam
- •Quickies are ready-made cocktails modeled on 5-hour ENERGY
- •He proposes renting countertops of many liquor stores for big brands
- 1:04:54 – 1:11:17
Why Jesse Prioritizes Impact Over Scaling
Jesse shows his planned 2024 calendar and explains why he runs coaching programs, speaking and events instead of scaling a new business. Daily messages from people give him a return he says no business could. Sam then asks how he handles money.
- •His color-coded 2024 calendar includes family travel, races and speaking
- •His family office suggested scaling, but he points to daily messages from people he's helped
- •He says the feeling of impact matches the feeling of a business exit
- •He says he doesn't think much about growing his money and spends on what he enjoys
- 1:11:17 – 1:18:24
Compliment, Congratulate, Console
Jesse explains his three-minutes-a-day relationship habit, which grew from writing handwritten letters in his 20s. He says complimenting, congratulating and consoling friends builds authentic relationships.
- •Short messages create 'permission slips' to reconnect
- •Reaching out to grieving friends is never forgotten
- •He writes 25 to 50 handwritten thank-you letters each year
- •Jesse says doing all three in a year changes how people see you
- 1:18:24 – 1:23:56
The Misogi, Kevin's Rule, and Defining Your Life
Jesse describes choosing one year-defining challenge each year and Kevin's Rule of doing something new every other weekend. The hosts reflect on how he defines life on his own terms, and Shaan closes with a north-star line about doing life with people you love.
- •The Misogi is one big year-defining thing per year
- •Examples include biking across America and living at a monastery
- •Kevin's Rule means a mini adventure every other weekend
- •The hosts compare his approach with Rob Dyrdek's focus on efficiency
- •Shaan closes with Mike Brown's idea of doing life with people you love
