Jesse Itzler Said “Do the Unexpected”. So I Built an AI for That.
This Video Changed My Mindset — Here’s the One Lesson I’m Running With
I first came across @JesseItzler while looking up notable alumni from American University. My son is also a proud AU Eagle.
I remember reading about this serial entrepreneur who built billion-dollar businesses, ran ultra-marathons, lived with a Navy SEAL, and sold companies to NetJets and Coca-Cola.
So when his video “15 Ways I Built Billion-Dollar Businesses Without Spending a Dime” popped up on my YouTube feed… of course I clicked.
Halfway through, I was importing the transcript into Google’s NotebookLM to pull takeaways I could start applying immediately.
Jesse’s energy is contagious. His mindset is next-level. He sets goals that most people would call impossible—and then just executes.
The principle that resonated most?
“Do the Unexpected.”
It’s the kind of advice that sounds basic—until you realize it’s the one thing that separates unforgettable from forgettable.
In business, people often do just enough.
But the real differentiator (the thing that creates lasting loyalty, referrals, and moments people remember) is when you go that extra, unexpected mile.
And in today’s world, where attention is scarce and expectations are low, those moments don’t just happen by accident. They’re built. Intentionally.
Since I’m so passionate about AI and tech…of course I couldn’t just hear this transformative advice and move on. I had to figure out how to take Jesse’s mindset and apply it to my world.
Here’s how Sales and RevOps teams can do the same—with a little help from AI.
4 Ways Sales & RevOps Teams Can Use AI to “Do the Unexpected”
1. Personalized Win Alerts for Your Clients
Use AI to scan social media and news outlets to detect when your customer lands a big client, wins an award, or gets promoted. Set up automated alerts so your team can reach out immediately with a warm, personalized “congrats.”
Bonus: Include a small digital gift card with a note like, “Coffee’s on me—cheers to your success!”
2. Send a Thoughtful Resource Before the Ask
Instead of waiting until you’re ready to pitch, anticipate your client’s challenges and send a tailored resource ahead of time. Use AI to analyze past conversations or behavior and recommend helpful guides, templates, or solutions.
“Thought of you when I came across this hiring checklist—figured it might come in handy as your team scales.”
3. Pre-Send Restaurant Reservations Before Client Travel
With travel signals from email/calendar integrations, your AI can help you reserve tables in cities your customers are visiting—before they even think to ask.
“Saw you’ll be in NYC next week—Lilia at 8 PM is confirmed. Enjoy!”
4. AI-Generated Gift Ideas Based on Customer Clues
Use AI to mine call transcripts and emails for subtle personal details—interests, birthdays, hobbies—and generate thoughtful gift ideas.
If they mention being excited about Wimbledon, maybe a tennis-themed care package hits the mark.
DIY No-Code: Send Automated “Congrats” Emails With a Gift in Under 30 Minutes
You don’t need a dev team—or any elaborate setup—to start doing the unexpected.
Just start. No excuses.
No waiting for the “perfect” tech stack.
Send that email. Book that table. Make that call.
But if you want to be known for this kind of thoughtfulness—like Jesse suggests—and make it repeatable and sustainable at scale, that’s when layering in some automation turns a good habit into your personal brand.
Here’s a quick, no-code way to build an automated “congrats + gift” workflow using Zapier + Clay + Giftbit.
🎯 Goal:
When a customer is mentioned in the news or on LinkedIn, automatically send a congratulations email with a personalized message and a digital gift card.
Tools You’ll Need:
Zapier (Free tier is fine)
Clay.com (for enrichment and email details)
Giftbit (digital gifting platform)
Google Alerts or LinkedIn + Zapier
Gmail or Outlook
Step-by-Step:
Set Up Google Alerts or LinkedIn Monitoring
Create alerts for phrases like: "Customer Name" + promotion or "Company Name" + funding.
Trigger in Zapier
Use Zapier to watch your RSS feed (Google Alerts) or monitor LinkedIn posts from specific people.
Pull Contact Info with Clay
Use Clay to enrich contact details—find their best email, job title, or recent update.
Generate a Custom Email Using OpenAI via Zapier
Prompt example:
Subject Line: {YourName} / Congrats
(This simple subject line is actually one of the things Jesse Itzler suggests—short, direct, and designed to stand out in a cluttered inbox.)
Prompt:
Write a short, warm email congratulating {Name} on their recent {milestone}. Mention something specific about their accomplishment and offer a $10 gift card. Keep it under 100 words, genuine, and easy to scan.
Send via Gmail or Outlook
Zapier automatically sends your message with the custom subject and message.
Include a Giftbit Card
Add a $10 Starbucks or Amazon card via Giftbit. Choose “open-choice” so they can pick what they want.
Congrats, You Just Did the Unexpected
It didn’t take much effort. It wasn’t expensive. But it will be remembered.
And that’s what Jesse was talking about.
When everyone’s following the script, showing that you care enough to do what no one expects is what turns clients into raving fans.
And Sales + RevOps into real growth engines.
Final Thoughts
Jesse’s video reminded me that the secret to extraordinary results isn’t always found in the most complex strategies.
It’s found in consistent execution of simple, high-impact actions.
Doing the unexpected, and applying the power of tech and AI to make it repeatable, instantly makes your reach 10x larger. That, my friend, is the cheat code—and possibly the smartest life hack AI gives us today.
And the best part?
AI doesn’t just help you keep up…it helps you stand out…at scale.
Thanks for the reminder, Jesse!
You’ve got a new fan—and a bunch of business leaders now thinking differently because of you.
#DoTheUnexpected #AIForSales #RevOpsStrategy #JesseItzlerInspired #JesseItzler