“You own it?”
“Taylor Air. Bought two years ago. Regional charter. Six aircraft total.”
He pulled out his phone. Showed the website. Taylor Air Charter Services. Professional design. Fleet page: six helicopters, mix of Airbus H125s and H130s. Services: executive transport, medical evacuation, aerial survey. Owner and CEO: Travis Taylor.
The room exploded again.
He owns it. Six helicopters. He has a helicopter company as a side business.
A Morgan Stanley guy in the crowd calculated aloud, could not help himself. “H125s run three million each new, maybe two million used. Times six—eighteen million in aircraft minimum. Plus operations, pilots, insurance, hangar fees, maintenance. Twenty-five million business. Conservative.”
Recalibration happened in real time. Not just a rich guy who did well. This was owns a tech company at $180 million and owns an aviation company as a side investment. This was flew here in an aircraft from his own fleet. Wealth most people see only in movies.
Derek’s reality fractured completely. He had thought—genuinely believed—Travis might be doing okay. Mid-level job. Decent apartment. He had invited him to highlight the gap between Derek’s success and Travis’s presumed mediocrity.
Reality: Travis was wealthier than Derek’s entire extended family combined. Earned every dollar. Did not inherit. Built it.
Chelsea’s reaction was genuine.
“Travis, that is insane. You own Taylor Air? We were literally looking at charter services last month for the honeymoon. Your company came up in the search.”
Travis, pleased: “You were researching us?”
“Yes. Incredible reviews. Five stars everywhere.”
Derek’s face turned red. His fiancée had researched Travis’s company for their honeymoon without knowing. The irony burned.
Questions intensified.
“Why buy a helicopter company?”
Travis made it sound reasonable. “Got my pilot license in 2022. Fell in love with flying. Company for sale. Numbers made sense. Now I fly whenever. Best investment outside Apex.”
He made owning six helicopters sound logical.
“You flew yourself tonight?”
“Rated and current on the H125 and H130. Jordan co-piloted.” He gestured vaguely. Jordan at the bar raised a glass.
Brad asked, “What’s flying yourself like?”
“Peaceful. Above everything. Traffic doesn’t exist. Perspective. Reminds you problems are smaller than they seem from the ground.”
Even hobbies came with philosophical insights.
Derek attempted to compete. Words came out desperate.
“Just bought a new Audi. A6. Fully loaded. Performance package.”
Silence. No response. The comparison was too stark.
Someone redirected to Travis.
“Where do you live in New York?”
“Tribeca. Two-bedroom loft.”
A finance guy: “Tribeca two-bedrooms start at two million. Luxury units go four or five.”
Travis neither confirmed nor denied. “Good space. Rooftop access.”
Nice.
Derek’s house: $450,000 in Greenvale. Family discount. The math wrote itself. Travis chose smaller in a better location. Derek settled for bigger because it was cheaper.
Derek tried again, voice tight.
“Must be nice with the tech bubble and venture capital.”
Travis shut it down instantly. Kind but firm.
“We’re profitable. Two years running. Don’t need to raise more money.”
Facts, not feelings. The tech-bubble excuse died.
Chelsea asked about Tribeca. Restaurants. Walking to work. She lit up talking to him. Eyes bright with genuine interest. Derek watched. She never looked at him like that.
The betting pool haunted him. Twenty bucks says hoodie and Uber. Reality: $180 million. Twenty-five million in helicopters. Forbes. Error margin infinite.
Derek ordered a third bourbon. 7:20. Already lost. The humiliation was only beginning.
His first attempt to regain ground came too loud, too forced.
“Yeah, so I closed a huge deal last week. Two-point-nine million.”
Voice carried across three conversations. Interrupted them. The group nearest offered polite nods. Attention drifted back to Travis explaining API integration.
Someone asked Derek, more courtesy than interest, “What deal?”
“Commercial real estate. Office complex in Stamford. Major client.”
Brad’s voice cut through.
“Isn’t that the Riverside project your dad’s been working on since 2010?”
“Well, yes, but I handled the closing.”
Jason added, “Didn’t your dad introduce the client at a 2008 golf tournament?”
“Technically, yes, but—”
He could not finish. It sounded empty. Taking credit for someone else’s decade of work. Travis did not compete. Just listened politely. Gave no indication he heard. Somehow that made it worse.
Second attempt focused on possessions.
“Just picked up a new Audi A6. Performance package. Fully loaded.”
Brad tried helping. “Nice, dude.” To Travis: “What are you driving?”
“Don’t own a car. Manhattan parking is six hundred a month. I bike most places. Subway when it rains.”
Someone, surprised: “Worth that much and no car?”
“Faster in traffic. Better for the environment. Why own something I barely use?”
Chelsea lit up. “So environmentally conscious. Amazing.”
Derek glared. She did not notice.
Third attempt: real estate.
“Chelsea and I bought a house. Four bedrooms. Greenvale Heights.”
Chelsea corrected innocently. “Your dad’s investment property. Family rate.”
Undercut publicly. Did not realize.
“Still counts.” To Travis: “Where’s your place?”
“Tribeca. Two-bedroom.”
The finance guy again: “Those go three to five million.”
Travis: “Good space. Rooftop.”
Nice.
Everyone did the math. Derek: four-bed, $450,000, discount. Travis: two-bed, three million-plus, earned.
Fourth attempt. Desperate.
“Getting married. June. Two hundred and fifty guests.”
Travis, genuine: “Congratulations. Wonderful.”
“Seeing anyone?”
“Ended a relationship months ago. Work-life balance is tough when you’re building something.”
Derek saw an opening.
“Family business has balance. Leave at five. Have a life.”
Travis nodded. “Makes sense for your situation.”
Implication: Travis chose the harder path. Derek chose ease.
Then detonation.
Katie asked innocently, “Chelsea, did you message Travis on LinkedIn?”
Derek’s head snapped. “What?”
Chelsea pulled out her phone. Career-advice LinkedIn thread. September 14th.
Hi Travis, exploring marketing transitions. Would love to learn about Apex.
Travis responds: Happy to help. Connecting you with CMO Diana Roberts.
Chelsea: Great call. Amazing advice. Actually thinking of applying.
Derek read it three times.
“You talked to his employee. His CMO. Amazing advice. Actually seriously thinking of applying. You are applying to his company?”
Voice rose. People turned.
“Good opportunity. Why are you making this weird?”
The room went silent. Everyone hearing.
Travis handled it gracefully.
“Chelsea is talented. Diana mentioned the call went well. Always looking for good people.”
Chelsea beamed. “Really?”
“Really. Send a resume Monday.”
Class move. Derek looked petty.
Derek spiraled. Fiancée reached out secretly. Might leave Derek’s dad’s company for Travis’s. Admired Travis more.
Fifth attempt. Pure desperation.
“I donate to the school every year. Alumni fund.”
Mr. Harrison overheard.
“Generous, Derek.” He turned to Travis. “I wanted to thank you publicly—”
Travis, uncomfortable: “Mr. Harrison, please don’t.”
“The Excellence Through Inclusion scholarship. Five hundred thousand. Administration told me.”
The room gasped. Half a million. Anonymously.
Travis shifted. “I asked them not to say.”
“Why anonymous?”
“Not about me. About kids who need a chance.”
Applause—real. Some wiped their eyes.
Derek’s history: $500 annually. Tax deductible. Ten-year total: $5,000. Travis’s single donation: $500,000. Ratio: one hundred to one.
Brad approached Travis privately. Returned changed—softer, humbled. Later, to Derek:
“I apologized for high school. The group chat. Being a dick.”
“What’d he say?”
“Took courage. Appreciated it. I’m growing.” He looked at Derek. “You should too.”
“I can’t.”