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My relationship with Jack Kennedy was forced upon me.
By my project manager at the time, Lenny.
“Jack needs help,” he said. “Train him.”
Jack had arrived at our project—Manchester Lakes in Algonquin, Illinois—in the spring of 2001 in a stolen Ford Taurus. (Story for another time.) He was a West Point graduate incapable of acting like it.
He knew nothing about construction.
He knew people though.
The first home I walked with him was supposedly “complete.”
Light fixtures were missing. Electrical wires jutted from the walls. There was no railing to the basement. This home was a lawsuit waiting to happen.
“When’s this supposed to close?” I asked.
“Already got the Certificate of Occupancy,” Jack said.
No chance.
The inspector was a colossal jerk.
“How on earth did you pull that off?” I asked.
“Just gotta learn how to connect with people, Hartmann.”
“What about the homeowner? This guy’s gonna kill you.”
“Nah,” Jack said. “He loves me. Already set me up on a date with his daughter.”
That was Jack Kennedy.
Eighteen months later, Jack moved to Hollywood to become an actor and writer.
Over the last twelve months, Jack and his saint of a wife, Claire, raised more than $300,000, recruited 19 actors, filmed in 13 locations, and made an independent film titled You Are Here.
Now they’re packing up their three kids, three dogs, and a 35-foot RV and driving across America trying to convince theater owners to take a chance on the film.
And because Jack Kennedy is an elite-level salesman, I invested in this thing.
In Episode 49 of The Craft of LBM Sales Podcast, you can hear Jack’s original sales pitch to me. In Episode 68, he returned after filming to discuss the challenges and rejection involved in bringing the movie to life.
Underneath it all are lessons every salesperson should understand.
1. Every Dream Eventually Becomes a Sales Job
When I started talking to Jack about making the movie, I expected stories about the inner workings of Hollywood.
We ended up talking sales.
First, Jack had to sell Claire.
Then investors.
Actors.
Editors.
Sound people.
Theater owners.
Distributors will be sold next.
At every stage, people told him: “This is crazy. It’ll never work.”
Welcome to sales.
This is the job.
And it helps to be a little crazy.
2. The Best Story Wins
Jack is selling more than a movie.
He’s selling a story.
A story about betting on yourself.
A story about pursuing a dream for 25 years.
And as Morgan Housel says, the best story wins.
Not the best spreadsheet.
Not necessarily the best product.
The best story wins.
Whether you’re selling lumber, windows, GenetiQ ERP software, or an independent film, the story behind the product matters.
3. You Can’t AI Your Way Into Relationships
Jack called theater owners asking them to take a chance on an unknown indie film. One theater initially quoted him $4,000.
After a personal phone call from Jack?
The number dropped to $500.
Why?
Because Jack made the time for a conversation about his dream—and what was in it for the theater owner.
Jack understands something many salespeople forget: A great story earns attention, but cash flow keeps the lights on.
So, he studied how theaters make money.
Concessions.
Seat volume.
Alcohol sales.
Live events.
He sold the emotional story first.
Then he sold the math.
4. Rejection Is Not Evidence You’re Wrong
In Episode 68, Jack said, “You’ll probably get 200 rejections for every yes.”
That’s not failure.
That’s knowing your numbers.
Sales is difficult because human beings are wired to avoid rejection, not pursue it.
The truth is twelve rejections can feel like 200.
Sometimes winning simply means staying in the game long enough for the law of averages to work in your favor.
5. Persistence and the Strength of Weak Ties
“People need to hear things seven times,” Jack told me. “And I guarantee you, the person you least expect to help you is going to help you the most.”
Jack’s whole tour runs on weak ties.
The idea is that the opportunities that change your life often don’t come from your closest friends. They come from friends of friends.
Old coworkers and your aunt’s neighbor and second cousins.
That’s exactly what Jack is leveraging. His national network of people rooting for him—and the people they’re willing to tell about this whole production.
West Point alumni.
Army buddies.
Former colleagues.
Someone who knows a theater owner.
Someone else who knows local media.
Too many salespeople underestimate the value of their broader network.
Everybody should know what you do.
Everybody should know what problems you solve.
Everybody should know how you help customers make, find, and save money.
Why?
Because opportunities compound through weak ties.
And this is what I admire about Jack and Claire’s dream.
It’s not just the movie. It’s watching a team pursue something unreasonable long after most people would’ve quit.
Whether you’re selling lumber, building homes, or driving an RV across America promoting a film, the work is the same.
Every job is a sales job.
The best story wins.
If Jack’s circus caravan rolls anywhere near your town, go support him.
The movie is called You Are Here.
Connect with Jack here.
Follow him on Instagram here.
And if nothing else, you’ll get to watch a guy bet heavily on himself—which is still one of the most compelling stories in the world.
Thanks for reading.
I’ll see you back here next week.
| Somewhere between your quote and the invoice, your margin went missing. Click here to see where it’s happening. GenetiQ, the next evolution of ERP – discover how industry experts Gary Brookshaw and Bradley Hartmann help sales teams sell smarter, coach better, and grow faster. Join the conversation. |
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