Jesse Itzler’s success isn’t built on traditional business tactics—it’s driven by bold action, relentless energy, and a deep focus on relationships. From handwritten letters to unexpected gestures, his strategies show that real growth comes from standing out and building genuine connections in a crowded world. This article breaks down Itzler’s unconventional approach to business, networking, and personal growth—and how small, intentional actions can create outsized results. If you want to grow faster and build stronger relationships, it starts by doing what most people aren’t willing to do.
There is a version of business success that looks like relentless hustle, massive ad spend, and a CRM dashboard blinking with data points. And then there is Jesse Itzler’s version — handwritten letters, staying late at the bar, and remembering that a grieving client needs a phone call more than a pitch deck.
Itzler, the co-founder of Marquee Jet, a company that went on to do over $5 billion in sales in six years before a landmark exit to Warren Buffett’s NetJets, has built his career on a deceptively simple premise: relationships are the most scalable, most cost-effective growth strategy available to any entrepreneur. In a world drowning in digital noise, he has made a science out of being genuinely human.
These are the 15 strategies he credits for that success — and why, decades later, they still hold up.
1. Write Handwritten Letters
In his early 20s, Itzler had no marketing budget. What he had was time and intention. He committed to writing 10 handwritten letters a day — to mentors, prospects, people who inspired him. Over a year, that became over 3,000 small gestures of respect and attention.
“Everybody reads a handwritten letter,” he says. In a world of email overload and assistant gatekeepers, a physical envelope stands alone. It doesn’t demand anything. It simply signals that someone took the time.
The practice works as a long game. Not every letter becomes a sale. But over time, those seeds compound. The cost is a stamp. The return can be a relationship that lasts decades.
2. Maintain a Hot 25 List
Itzler keeps a curated list of 25 people he wants to stay on the radar of — not to sell to, but simply to remain connected with. Each quarter, he sends them a note, a DM, a clip of something they’d find interesting. No ask attached.
The strategic elegance here is in the permission it creates. When you run into someone you’ve been quietly investing in over months, you’re no longer a cold contact. You’re a familiar presence who once sent them a great article about surf destinations because you remembered they loved the ocean.
He calls it playing offense, not defense. It reframes networking from reactive to intentional — from “hope I bump into the right people” to “I’ve already been building this relationship.”
3. Use DMs Strategically
Most people guard their email. Not everyone answers their phone. But social media DMs are often handled personally, even by senior executives. Itzler illustrates this with a story of a stranger who slid into his DMs with a no-lose offer — send a logo, receive branded merchandise for free to evaluate. No risk. Just value.
That person got his entire business.
A well-crafted, value-first DM is one of the most underused tools in business development. Lead with something useful. Ask for nothing. See what opens.
4. Have a Hometown Restaurant
This one sounds social. It is strategic. Itzler advocates for choosing a restaurant — ideally a buzzy, well-regarded one — and becoming a known presence there. Learn the staff’s names. Leave thoughtful notes. Tip generously. Over time, you become someone who can call ahead and get a table when your client visits from out of town.
The underlying principle is environmental credibility. Walking into a room where people know your name, greet you warmly, and make you feel at home communicates status, ease, and social capital to anyone you bring with you. It says: this person belongs here.
5. Master the Three C’s: Compliment, Congratulate, Console
This may be the most emotionally intelligent strategy on the list — and the one most often overlooked in business contexts.
Itzler’s framework is simple: when someone in your inner circle achieves something, congratulate them genuinely. When something they’ve done impresses you, tell them. And when they are grieving — a loss, a failure, a hard season — reach out. Don’t let it pass.
“If you have somebody in your life that’s grieving and you don’t reach out to them, they’ll never forget it,” he says plainly.
This is not manipulation. It is emotional attentiveness — the practice of treating the people around you as full human beings with lives beyond the transaction. In business, that is rare enough to be extraordinary.
6. Find Your Hot Spots
Every city has places where the right people congregate — a hotel lobby, a restaurant at lunch, a specific happy hour. Itzler famously made the Beverly Hills Hotel his unofficial office early in his career, studying the social dynamics of Hollywood’s power players simply by showing up and paying attention.
You don’t need a hotel room to eat at the restaurant. You don’t need a ticket to the VIP section to sit at the bar. Access, in many cases, is simpler than it appears. What matters is being in rooms where interesting things can happen.
7. Buy the Cheap Seats
Closely related to finding hot spots, this strategy is about removing the psychological barrier of cost from showing up. You don’t need courtside. You need to be in the building.
“When you’re in the building, amazing things can happen,” Itzler says. “When you’re not in the building, nothing can happen.”
This applies to conferences, events, industry gatherings, and social occasions. The cheap seat puts you in proximity to serendipity. The couch at home does not.
8. Stand Up Before Meetings
A small discipline with significant signal. Itzler’s rule at Marquee Jet was clear: when a meeting is about to begin, you stand. You don’t sit and rise awkwardly when your contact walks in. You are upright, present, and ready to greet them at full energy.
It’s behavioral, not cosmetic. A meeting, he argues, can change your life. The energy you bring to it should reflect that.
9. Follow Up on Everything
The follow-up is where most business falls apart — and where Itzler has consistently found an edge. After any meeting, he sees an opportunity: to summarize, to express gratitude, to clarify next steps, to recover ground if things didn’t go perfectly in the room.
In real-time conversation, you’re reactive. In a follow-up, you’re thoughtful. That asymmetry is an advantage available to everyone who chooses to use it.
10. Do the Unexpected
This is Itzler’s signature move — and perhaps what most defined Marquee Jet’s reputation. While every competitor handled the expected well — responsiveness, reliability, professionalism — he was simultaneously asking a different question: what would no one else think to do?
For a client traveling to Mexico with kids, he researched and vetted 10 local pediatricians. For a client visiting during spring break, he pre-booked restaurant reservations for the week. No one asked. He just did it.
“Ask yourself, what could I do differently that no one else is doing to have an impact on my customer?” he says.
The unexpected doesn’t require more money. It requires more imagination and a genuine interest in the person you’re serving.
11–15: Presence, Persistence, and Personality
The final five strategies are quieter, but no less important.
Be where your feet are — Itzler tells a story of arriving at a wedding in low energy, only to end up beside someone he’d long wanted to meet. The shift in his attitude — from reluctant to present — changed the outcome entirely. Wherever you are, commit to being there.
Stay late — The best opportunities frequently arrive after the room has thinned. “Luck doesn’t happen watching TV on your couch,” he says. Staying late is a form of creating it.
Write a proper email — Subject lines that cut through, bodies that are short and purposeful, clear calls to action. Read it as the recipient before you send it. Every word should earn its place.
Be a connector — Introducing two people who share a common interest costs nothing and generates significant goodwill. Think of the people in your network as a living map of potential connections, and make the introductions generously.
Be known for something — In a crowded market, distinctiveness is an asset. Itzler knows a man who sends extravagant Halloween candy baskets every year without fail. That man is the Halloween guy. Whatever your version is — a hat, a ritual, a consistent act of generosity — find it, own it, and repeat it.
The Deeper Thread
What runs through all 15 of these strategies is not a sales playbook. It’s a philosophy of attention — the practice of noticing people, investing in them before you need anything from them, and showing up with energy and intention wherever you go.
In an era of automation, algorithmic outreach, and frictionless digital communication, the human gesture — the letter, the call, the unexpected act of care — has become a differentiator precisely because it’s rare. These strategies didn’t cost Jesse Itzler much money. But they required something arguably more valuable: genuine interest in other people.
That, it turns out, is a business strategy that never goes out of style.
These strategies were shared by Jesse Itzler — entrepreneur, co-founder of Marquee Jet, and author — in a podcast discussion on building businesses through human connection and relationship-driven growth.
FAQ Section
What are Jesse Itzler’s top business strategies? Jesse Itzler’s top strategies include writing handwritten letters, maintaining a “Hot 25” list, mastering follow-up, doing the unexpected for clients, and being a connector. Most require no financial investment — only consistency and genuine human attention.
How did Jesse Itzler grow Marquee Jet to $5 billion in sales? Itzler attributes Marquee Jet’s growth largely to relationship-based strategies: proactive client care, unexpected personal touches, deep networking, and always going beyond what was expected in service delivery.
What is the Hot 25 list strategy? The Hot 25 list is a curated list of 25 key contacts you want to stay top-of-mind with. Once per quarter, you reach out with something valuable — an article, a note, a recommendation — without asking for anything in return.
Why do handwritten letters still work in business? In a world of email overload and digital noise, a handwritten letter is a physical, personal gesture that almost always gets read. It signals effort and respect in a way that digital communication rarely can.
What does “do the unexpected” mean in business? It means going beyond what clients contractually expect — anticipating needs they haven’t voiced, making their life easier in ways they didn’t ask for. Itzler sees this as the clearest way to separate yourself from every competitor who is only doing what’s required.
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