The storyteller who sold golf: sales lessons from Ely Callaway

Published: Wed, 06/04/25

Updated: Mon, 06/09/25

June 4, 2025

TOGETHER WITH

Welcome back to the first June issue of The Quota. We’re looking forward to the onset of summer, if only because it’ll be too hot outside to do anything except read newsletters. In this not-yet-sunburnt issue, we’ll look at the story of golf magnate Ely Callaway, share a Sales Fail about ChatGPT, and give some advice to a young rep in a room full of vets. Let’s do this.

NUMBER OF THE WEEK

Sales turnover has decreased by 7% since 2022

Source: Salesforce

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

The owner of a Kentucky car lot who rolled back odometers so he could charge customers higher prices has been sentenced to 18 months in federal prison. The sentence for Randy Huff also included $40,000 in restitution. Huff admitted he had mechanics replace the odometers on cars and SUVs to show that the mileage was much lower than it actually was. In one case, the actual mileage on a 2012 Jeep Grand Cherokee was 286,012, but the odometer Huff has put in it showed 111,800 miles. You can read more about it here.
A door-to-door salesman who was 'enamored' with knives was recently sentenced to 20 years in prison for killing a man while he was out prospecting. The deadly scuffle occurred on May 26, 2022, after Michael Tsamas paid a sales call to Joseph Delgardio's home on West Veterans Highway in Jackson, New Jersey as the victim, his wife and two of their three daughters were having dinner. After Tsamas left, the victim followed him to retrieve an account number his wife had provided, and the two got into an altercation which turned fatal when Tsamas stabbed Delgardio. You can read more about it here.

FEATURE

The storyteller who sold golf: Ely Callaway's billion-dollar lessons

When Ely Callaway Jr. died in 2001, he left behind a billion dollar golf empire built from a $400,000 investment in a struggling golf club company. His success, in his own words, was fueled by his ability to tell a compelling story: "As long as you've got a good story, you can convince anybody."

The Birth of a Salesman

Callaway was born in LaGrange Georgia in 1919. By the age of 10, he had begun his sales career selling magazines. But he didn’t spend the money on himself, instead he saved his money and convinced a peach farmer to lease him peach trees (very Georgia). As he recounted in his autobiography, The Unconquerable Game, at age 21, he convinced a New York mafia boss to help him procure $350 million worth of uniforms for the U.S. Army during World War II.

After the war, Callaway cut his teeth in the textile industry. By 1968, at 49 years old, Callaway had climbed to the presidency of Burlington Industries, the world's largest textile manufacturer, where he spearheaded the development of polyester blends that transformed the industry. His tenure ended when he discovered that Burlington was secretly defying SEC orders regarding monopolistic practices. Rather than compromise his integrity, he demanded written proof of his non-involvement and ultimately leveraged his detailed documentation into a lucrative buyout when the company tried to silence him.

After leaving Burlington in 1973, he founded Callaway Vineyard & Winery in an area deemed unsuitable for premium wine. His sales pitch was so compelling that he convinced Bank of America to loan him $1 million "on the basis of only a few sips of wine." The result? Wines so exceptional that Queen Elizabeth II asked for a second glass at a 1976 reception and requested to meet the vintner. He sold the winery in 1981 for $9 million (approximately $32 million in 2025).

Selling Golf Clubs Out of a Cadillac

In 1982, Callaway used his vineyard profits to buy half of struggling Hickory Sticks USA, one of his favorite golf club brands, and renamed it Callaway Hickory Stick USA. As company president, he was literally selling clubs out of his Cadillac in Carlsbad, California. Not out of desperation, but because he wanted to be closer to potential customers and understand what they wanted.

This helped Callaway understand what his golf industry competitors didn't: golfers were starving for something new. His breakthrough came with the Big Bertha driver, which featured revolutionary large-volume steel clubheads that made the game more forgiving for average players. But the real genius was in how he sold it. Callaway didn’t sell Big Bertha by focusing on the product features, he sold outcomes that golfers wanted using messaging like "making the game more enjoyable for the average golfer" by designing "the most forgiving golf clubs in the history of the game — giving more golfers more opportunities to hit a few additional 'great' shots each round."

Callaway didn't just create better products—he changed how golf equipment was sold. His approach to the crowded golf ball market was simple. Rather than creating separate balls for different purposes, he developed the Rule 35 as a "complete-performance" ball, telling customers: "This eliminates confusion and guesswork in trying to identify the golf ball that is right for each individual golfer." He transformed golf retail through direct-to-consumer strategies and launched innovations like computer-aided fitting centers decades before they became industry standard. This allowed him to make Callaway Golf the first golf company to go public on the New York Stock Exchange in 1992, with a market capitalization of $250 million that has soared to over $1 billion today.

Ely Callaway's legacy isn't just about golf clubs—it's about the power of principled disruption. He proved that the greatest sales weapon isn't manipulation or pressure, but creating genuinely superior products and having the grit to sell them with absolute conviction, even if it means hawking them out of your car trunk.

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How long you can get away with being “new” until you’re held accountable
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Organizing your calendar while leaving time to cry
The rules of the kitchen (stealing someone’s yogurt is literally a crime)
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MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

Electric automaker Polestar is owned by which major car brand?

A. Saab
B. BMW
C. Volkswagen
D. Volvo

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

I'd been working on a deal to supply custom office furniture to a growing marketing agency for about six weeks. After several promising calls, I had a great conversation with their owner about delivery timelines and budget approval. She seemed genuinely excited about moving forward.

I took thorough notes during the call but wanted to make sure my follow-up email was perfectly crafted so I decided to use ChatGPT to help structure my thoughts into a professional email, copying my notes and asking it to write a follow-up. The response looked great, so I quickly copied and pasted it into my email, gave it a quick skim, and hit send. For the next three days, radio silence—unusual since she'd been very responsive throughout our conversations.

I reviewed our email thread and discovered my fatal mistake. At the bottom of my follow-up email was ChatGPT's response: "This email effectively summarizes your discussion points while maintaining a professional tone and clear next steps. The structure moves logically from recap to value proposition to call-to-action. Is there anything else you'd like me to help you with regarding this client communication?"

When I sent a follow-up asking about next steps, she responded explaining she was disappointed I was using AI to write communications and couldn't even proofread properly. She said if I couldn't take the time to write a genuine email, she didn't trust me to handle their furniture order carefully. The deal was dead, and I learned an expensive lesson about always double-checking before hitting send.

Anonymous Location withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- May 2025

WORTH A PEEK

What are the things that nobody tells you before you go into sales? The list is long, and in a recent Reddit thread, hundreds of sellers weighed in with answers ranging from “The perfect sales process doesn’t guarantee success,” to “admin stuff eats up so much of your time.” You can see all the responses here.

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

Dear Quota Team,

I'm 24 years old and sell enterprise cybersecurity solutions to C-level technology executives, most of whom are 20-30 years older than me. I have nothing in common with these prospects—I don't play golf, I don't frequent fancy restaurants, and I feel completely out of place at networking events where everyone discusses mortgages and kids' college plans. When I do get meetings, I can sense their skepticism about my age and experience level, often asking to speak with "someone more senior" or treating me like an intern rather than a legitimate sales professional. My older colleagues tell me to "just build relationships over time," but these executives won't even return my calls, let alone invest time in getting to know me. The few people I naturally connect with — younger mid-level IT managers and engineers — aren't decision-makers and can't influence purchasing decisions. How do I earn respect and build meaningful business relationships when I'm fundamentally different from my target buyers and can't compete with my teammates' established networks?

Not Taken Seriously in New York

Dear Not Taken,

Lean into being the rep who truly understands how younger employees create security risks through social engineering, mobile device vulnerabilities, and cloud-based threats that older executives often underestimate. Instead of trying to mimic your colleagues' relationship-building approach, become the expert who can walk into a room and immediately spot security gaps they've missed, speaking their language about emerging attack vectors and threat landscapes. Many seasoned executives will respect genuine technical competence over golf partnerships, especially when you're the one alerting them to blind spots their current vendors haven't identified. Focus on being indispensable through knowledge rather than social connections. Bringing a fresh perspective on modern threats is more valuable than another dinner invitation. Good luck!

Quiz Answer: D. Electric automaker Polestar is owned by Volvo (you can read the source article here)

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Today's email was written by Ken Kupchik, Erica Furgiuele, Steve Rado, and Emily Hill.

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