How a waterbed salesman built the Bob's Discount Furniture empire

Published: Wed, 08/06/25

Updated: Fri, 08/08/25

August 6, 2025

TOGETHER WITH

Good morning and welcome back. In this week’s issue of the sales newsletter read by presidents, kings, and prison inmates, we’ll take a look at the story of Bob Kaufman, founder of Bob’s Discount Furniture. We’ll also share a Sales Fail about summer sweat, and give some advice to a sales manager whose top performer has a bad attitude. Sit back, relax, and enjoy!

NUMBER OF THE WEEK

If you engage a lead within 60 seconds of inquiry, it boosts conversion rates by almost 400%

Source: Lusha

SALES ROUNDUP

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

A Chicago Lamborghini dealer made millions selling cars to unauthorized customers, the automaker says. Automobili Lamborghini America says it was misled by Gold Coast Exotic Imports about some of the customers who bought cars from the dealer. Gold Coast allegedly misrepresented to Lamborghini that it sold cars to a former Chicago pro athlete and the chief executive officer of a chiropractic clinic in Minnesota, people considered to be retail customers. But the vehicles were actually sold to “brokers” and “resellers,” including one who “previously pleaded guilty in a criminal fraud case that involved selling luxury cars to drug dealers and pimps as a means of laundering money.” You can read more about it here.
Salesforce CEO Marc Benioff has made AI central to the tech giant’s future (and present) success, even going as far as almost changing the company’s name to Agentforce, in reference to AI agents. In fact, AI agents are so effective that they're now doing 30% to 50% of all the work within Salesforce itself. But Benioff is still hiring for sales, and he claims that despite their effectiveness, AI agents won’t lead to mass unemployment. Fortune interviewed Benioff, and he explained his thoughts. You can read the interview here.

FEATURE

Photo by Nikkiana, CC BY-NC-SA 2.0

How a Waterbed Salesman Built the Bob’s Discount Furniture Giant

Bob Kaufman never intended to become one of the most recognized faces on television commercials. Kaufman describes himself as an "extreme introvert" who just wanted to stop working for someone else. But through a combination of authentic salesmanship, relentless advertising, and an almost obsessive focus on customer value, Kaufman turned a single furniture store into a billion-dollar empire that redefined how America shops for furniture.

From Catastrophe to Opportunity

Kaufman's path to retail fame began with a devastating motorcycle accident in 1976. While working as a manager at Radio Shack, he became distracted on his way to a meeting and crashed into a telephone pole. Doctors almost amputated his right leg and predicted he'd never walk again.

During his year-long recovery, a friend recommended he try sleeping on a waterbed. It transformed his sleep and, ultimately, his life. Despite describing himself as "very risk-averse," Kaufman decided to sell the waterbeds that had saved him.

His strategy was simple: lease space inside larger furniture stores and focus purely on value. By the 1980s, he was operating in 24 stores throughout New England. But when the waterbed industry crashed in 1990, Kaufman faced a crossroads.

In 1991, during a recession when furniture stores were closing left and right, Kaufman and his partner Gene Rosenberg opened Bob's Discount Furniture in a bankrupt furniture store in Newington, Connecticut. They negotiated an unconventional deal: the landlord covered taxes, heat, and utilities in exchange for a percentage of sales. This kept fixed costs low and allowed them to focus on moving volume, while offering deeper discounts than competitors.

The Anti-Salesman Who Became the Brand

When Kaufman told his father, a decorated World War II veteran and advertising executive, that he planned to do his own commercials, the response was brutal: "Son. I love you dearly, but you look like crap and your voice is worse. Don't do it."

Kaufman ignored the advice and created one of retail's most successful advertising strategies. By 1997, Bob's was broadcasting roughly 500 commercials a week in Connecticut alone.

"The reason it works is because every business wants customer attention. But how do you get through the din? By not being your typical pitchman. By having a scratchy voice. By dressing in jeans and a polo shirt," Kaufman explained during a rare speech to business students at the University of Connecticut. "I would work at the warehouse, go do an ad, and go back to the warehouse in the same clothes. People feel like they know me.”
This wasn't accidental, it was strategic. In an industry built on slick salespeople and negotiable prices, Kaufman presented himself as the neighbor who happened to sell furniture.

The Psychology of Stress-Free Selling

Kaufman made a crucial discovery about furniture buying: it's the third most stressful purchase experience after buying a house or car. So he put free cafés in every store. "When I'm chewing on a cookie, I can't be stressed," he reasoned. "A lot of people stop in after lunch for a cookie, a piece of candy or a cup of coffee. They are always welcome. They may not buy something today, but they'll be back."

This wasn't just hospitality, it was sales psychology. By removing pressure and creating comfort, Kaufman transformed the furniture buying experience. Customers could browse without harassment, snack without obligation, and buy when they were ready.

Building the Sales Machine

Behind the folksy commercials was a sophisticated sales operation. Every employee had to complete three weeks of training before hitting the floor. Depending on success, salespeople could earn between $40,000 and $100,000 annually.

Kaufman's partner Gene Rosenberg gave him advice that became company doctrine: "It's all about your people. If the people who work for you aren't happy, your customers won't be happy." Kaufman made it a point to personally meet every employee. "I don't want anyone to say, 'I work at Bob's Discount Furniture, but I've never met Bob.' We run it like a small, family business."

The Values That Built an Empire

When Raymour & Flanigan offered to buy the company, Kaufman's response revealed his true priorities. "We had 500 employees. I knew them all by name because I'd hired them. All of these people helped me to grow, and if we sold, many of them would be out of work. We declined."

This wasn't just sentiment—it was smart business. By prioritizing employee stability and customer value over quick profits, Kaufman built sustainable competitive advantages that private equity eventually couldn't ignore. Bain Capital acquired the company in 2014. Kaufman remains actively involved, but is no longer the face of the brand, he’s been replaced by “Little Bob”, a cartoon character designed in his likeness.

—

Today, Bob's Discount Furniture operates 189 stores across 24 states with over $1.1 billion in annual sales.

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MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

How many iPhones were sold by Apple in 2024?

A. 1.2 billion
B. 16.8 million
C. 232.1 million
D. 189.4 million

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 sell commercial real estate and was invited to a high-end charity fundraiser at an outdoor country club last August. It was one of those networking events where half the city's business elite would be there, and I'd been trying to get face time with several potential clients for months.

The event was brutal—95 degrees with humidity that felt like a sauna. Within thirty minutes, I was sweating through my cotton shirt like I'd just finished a marathon. All the other men smartly took off their suit jackets, rolling up their sleeves and looking comfortable in their breathable fabrics.

I desperately wanted to remove my jacket too, but I could feel the back of my shirt was completely soaked through. The cotton had become see-through, clinging to me like plastic wrap. I could feel sweat pooling at my waistband. I kept my suit jacket buttoned just to try and cover it up, which only made me even hotter. For three hours, I suffered in that blazer, trying to network while looking like I was slowly melting. I could tell some people I was talking to were not listening to what I was saying, more focused on the sweaty mess of a man in front of them. I managed to exchange business cards with a few people, but follow-up calls went nowhere. I can't blame em. I bought a linen suit the next week.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- July 2025

WORTH A PEEK

If you knew that layoffs were looming at your company, what would be the best thing(s) to do right now? A recent post on Reddit asked this question—by a rep whose company is expecting layoffs in December. Commenters weighed in with tips. Check out the conversation 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 hired a recent college grad four months ago. He's a former D1 athlete and comes from a wealthy family. He's quickly become one of our top performers. The kid is undeniably talented and charismatic with clients, but he's extremely cocky, and it's becoming a problem. He openly brags about his deal sizes, makes comments like "that's how it's done" after closing big contracts, and refers to veteran reps' techniques as "old school" when they're struggling. Last week, he told a colleague who missed quota that "maybe sales isn't for everyone." While his numbers are impressive, the rest of my team is starting to resent him, and I've noticed people excluding him from lunches and after-work gatherings. He seems oblivious to how his attitude affects others and genuinely believes his success gives him the right to act superior. How do I address his arrogance without crushing the confidence that's driving his performance, especially when his results are actually backing up his ego?

Conflicted in California

Dear Conflicted,

You need to address this immediately before his toxic attitude infects your entire team. High performers who destroy morale are net negatives regardless of their individual numbers. Have a direct conversation explaining that while his results are impressive, his comments are unprofessional and damaging team cohesion, which ultimately hurts overall revenue and his own long-term success. Frame it around career development: successful sales professionals need to be able to work collaboratively and mentor others, skills that will be essential if he wants to advance into leadership roles. Protecting your team culture is more important than any single performer's ego. Good luck!

Quiz Answer: C. Apple sold 232.1 million iPhones in 2024. (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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