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A Jetsetter Family May Become A C-Suite Thanks To AI

by John Daly | Aug 13, 2025 | Undercover Jetsetter, blog

We looked into some AI reality for you and your family here.

You, as parents, won’t just be Mommy and Daddy.  Nope. You will take on or share one of these roles — CEO (Chief Efficiency Officer) or COO (Chief Optimization Officer).

No longer will he be just your son. He will be the family’s Chief Data Analyst — especially if he’s on TikTok.

And no longer will she be just your daughter. Nope. She will be either the Director of Groceries or the Director of Travel.

Strange world? You bet

Here, we take a serious – and sometimes funny – look at what’s ahead, or already here, for families who want to thrive in what will be our AI-dominated world.

Even if you haven’t noticed these, you will soon.

Airlines, Algorithms, and the Solo Traveler Surcharge

If you’ve booked a flight recently, especially as a solo traveler, you may have noticed something odd. That one-way ticket to Charlotte costs more than a round-trip to the moon.

Okay, not quite, but close.

Airlines like American, United, and Delta have quietly introduced pricing strategies that penalize solo, business, and One-Way travelers with higher fares. Why? Because algorithms assume you’re either desperate or on a corporate dime.

Example: A solo traveler flying from Charlotte to Fort Myers might pay $765, while two passengers booking together pay just $511 each. That’s a $254 “I-like-my-own-company” tax.

Here are three sources that back this up:

  • View From The Wing
  • USA Today
  • The Points Guy

To hopefully avoid this, try these sites we have compiled for you:

  • Booking.com
  • One Travel
  • Trip Advisor
  • Jetsetter Deals
  • Expedia

Now that’s on the travel side. But it’s happening on the foodie side too.

Walmart’s Price Tags Are Watching You

Walmart is rolling out digital shelf labels across 2,300 stores by 2026. These electronic tags can change prices in minutes, based on demand, inventory, or possibly how long you stare at the peanut butter aisle.

While Walmart insists it won’t use surge pricing, the infrastructure is there—and other retailers like Kroger and Whole Foods already use similar systems.

Here are some news sources backing it up:

  • CBS news
  • Forbes

You may be able to avoid this using these links by using grocery delivery and meal kit services:

  • Thrive Market
  • Instacart
  • HelloFresh
  • Gourmet Food World

Enter the Family Corporation

Another way is to restructure your family into a corporate style. Think of it as “The Brady Bunch meets Shark Tank.”

Yes, we indulge in a little whacky stuff here.

First, plan your new household organization chart

  • CEO (Chief Efficiency Officer): Oversees budget strategy, negotiates with airlines, and decides whether Grandma flies coach or cargo.
  • COO (Chief Optimization Officer): Manages grocery timing, tracks shelf price fluctuations, and coordinates coupon deployment.
  • Director of Travel: Books flights in pairs to avoid solo surcharges, monitors fare alerts, and knows every airport’s Chick-fil-A location.
  • Director of Groceries: Studies Walmart’s pricing cycles, plans shopping trips during markdown windows, and maintains a spreadsheet of cereal volatility.
  • Chief Data Analyst (aka Teen with TikTok): Tracks trends, hacks loyalty apps, and deciphers pricing algorithms better than most MBAs.

On the serious side consider these sites that could help on budgeting and planning:

  • Credit Karma
  • Rocket Dollar
  • Discount School Supply

Also here are some innovative and slightly ridiculous strategies you can do now.

Fake a Group Booking: Some travelers book two seats, then cancel one within 24 hours to dodge solo pricing. Airlines haven’t cracked down—yet.

Grocery Recon Missions: Send different family members at different times to test price changes. Bonus points if they wear disguises.

Dynamic Duo Shopping: Always shop in pairs. If prices drop when more people buy, bring your neighbor. Or your dog. Or a cardboard cutout of Betty White.

New Sci-Fi Comedy

Now for even more crazy looks-ahead that could happen on the family front lines.

Grandma the CEO: Holds weekly board meetings over oatmeal, vetoes Spirit Airlines.

Toddler as Director of Disruption: His aisle meltdown triggered a flash discount on creamed corn.

Teen TikTok Analyst: Discovered Elderberry Clusters drop in price during full moons.

Travel Department Merger Fails: Dad and Uncle Pete’s itinerary collapsed over Newark vs. LaGuardia.

Banana Price Wars: Family launched “Operation Yellow Curve.” Final entry: “We now grow our own.”

Grocery Calendar Threat Levels: Mom’s Homeland Security-style system includes “Code Red Sundays.”

Final and a Bit More Serious Thoughts

In a world where pricing is no longer fixed, families must evolve. Whether you’re flying to Curaçao or buying frozen waffles, the key is coordination, timing, and a little bit of humor. So gather the troops, assign titles, and start running your household like a Fortune 500 company. Just don’t forget to expense the snacks.

And tell us about your new family corporate structure.

This post contains affiliate links, which means we may earn a small commission if you purchase through them — at no extra cost to you. It helps us keep bringing you Jetsetter-approved tips, recipes, and sips. Thank you!

John Daly and Susan Anzalone are the Co-Creators and Co-Hosts of Undercover Jetsetter, a show on travel, food, and booze. They show you how to jet set the world and at home. They also co-authored the book, The TV Studio In Your Hand: How to Shoot, Edit & Deliver the Easy Way on Your iPhone. Join them for tips and hacks on the road, at home, or in the kitchen, and all over the world.  And yes, as you will see, all on the iPhone. Susan is an expert in food and wine since her childhood days in Australia and then the United States, being the daughter of two lifelong employees of Pan Am Airlines.  John is also a world traveler starting when he studied in Italy through his alma mater Providence College.  John is also a Nevada Hall of Fame Broadcaster during his years as a Las Vegas news anchor at KTNV.  He gained international fame as the host of the first all-video news magazine show, Real TV while also securing his bartending and mixology credentials from the Harvard Bartending School. You can follow them here on the free Wingding app on the Food and Travel Channels, on YouTube, Facebook, X, and Instagram.

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