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What’s the Craziest Thing You’ve Ever Done to Make a Sale?

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Nothing inspires a salesperson’s creativity like a game-changing deal that’s hanging just out of reach.

We asked eight sales professionals and business leaders for their best stories of going wayyyy above and beyond to close the deal. Enjoy, and tweet your own crazy sales stories to @nutshell. (The best story that can fit in a single tweet wins a prize!)

Walt Batansky, CFO of Avocat Group:

A few years back, our firm was targeting a publicly traded national medical products distributor with 100+ distribution facilities, that would be a perfect candidate for our services. Although they tried for months, the sales team couldn’t break the account.

Being the CFO at my company, I’m not typically involved directly with sales and marketing, but in a small company it’s often a case of “all hands on deck.”

I happened to read in the Wall Street Journal that the company we’d been chasing would be having an annual stockholders meeting about a month out. I bought 100 shares of their stock (around $6/share) which got me an invite to the meeting, and I flew to their headquarters in Jacksonville, FL.

After their presentation, the CEO and CFO stood in a receiving line to shake hands with the attendees, and I joined in line. When I reached the CEO, I told him that I was a stockholder, had reviewed their annual report, and was convinced that I could show them how to achieve a multi-million dollar savings on real estate and facility costs.

The CEO looked around a bit nervously (I thought he might be getting ready to alert security), gave me the name of their executive who handled properties, and told me to call him.

The next day I called that executive, of course, and told him that I was chatting with his CEO who thought we should speak. Our entire sales team was invited in to make a presentation and we won the account. They became our single largest account overnight.

P.S.: I also sold that stock, eventually—around $21/share, I believe.

James Pollard, owner of

The craziest thing I’ve ever done to make a sale was FedExing a prepaid mobile phone to a prospect’s office with a note that said, “I’m going to call this phone at 3:00 p.m. on Friday—make sure that you are nearby to answer.”

Sure enough, the prospect answered, and he had his entire office staff waiting by the phone to see if I was actually serious.

David Klein, inventor of Jelly Belly and owner of Candyman Kitchens:

My craziest sales story is when I invited the Associated Press business editor to my 90 square foot store, and asked my friends to be there at the same time with money in their hands, pretending to be customers.

When the editor showed up, they were lined up on the sidewalk outside the door at 10 a.m. on a Sunday morning.

Ten days later, I was the subject of a major article that appeared in hundreds of newspapers. Jelly Belly became a household name after that.

Eric Giglione, co-owner of Giglione Ackerman Agencies and host of The Daily Locker Room:

“We can do it on the hood of my car,” is the phrase of my story that people often pick out while I’m sharing my craziest sale story to friends and agents of mine. No, it’s not what you think.

Many, many years ago when I first started out in the life insurance business, unconventional ways of doing business were much more accepted and often encouraged, especially when it came to making a sale.

One day, I went to the house of a person who I had an appointment with, and he attempted to shoo me away because his entire house was being remodeled and there was apparently nowhere to sit. (Yeah, right.) Instead of just accepting it and agreeing to reschedule like most would, I said to him, “Lucky for you, the hood of my car can also serve as a desk. These benefits are too important; I can’t wait for your house to be finished.”

So, I ended up doing my entire presentation on my car in the guy’s driveway and made the sale. If I waited, the sale probably wouldn’t have happened. What I always tell my trainees is to push as hard as you can to make a sale and to try your best not to reschedule, because odds are you will never end up seeing the person again.


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Cristian Rennella, VP of Sales and Co-Founder of

About two years ago, my company was looking to close a sale with one of the three largest insurers in Latin America, and after many calls, meetings, and presentations without a favorable outcome, we decided to try a shameless idea.

We bought all the offline advertising that existed around the company’s corporate office, including billboards on public streets and roads, and advertising on the subway and train stations where their employees passed through twice a day. This way, each member of their team could see our ads and our services over and over again.

After one month they finally decided to try our service, and since then they are one of our biggest customers!

Henry Chen, sales consultant, Director of Marketing and Operations at 8 Ave Media:

The craziest thing I’ve ever done to make a sale was spill coffee on myself right in the beginning of a sales conversation. Before I tell you why anyone should do that, I feel the need to let you know a little about myself.

I’ve been in the digital marketing space for 5+ years offering sales advice as a consultant and in paid advertising. At the start of my career, I was already able to close sales on marketing services for speakers and ecommerce companies. However, I had an ambitious goal to aim for higher.

I realized early on that marketing managers, CEOs, and CMOs always had their guard up since they knew I was a “salesman.” These were always the hardest people to talk to because they already know tons about marketing or at least claimed to. And they don’t like the idea of being sold to.

So here it is, the story that changed my sales career. One morning I had a video call with someone who I admired and was super nervous to speak with—Mikko Hypponen, TED talk speaker, publicly known as the cybersecurity expert who catches online criminals.

Right before I got on the video call with him, I spilled coffee all over myself and he witnessed the whole thing. At that very moment, I thought to myself, “It’s over, I just lost the biggest client that we can ever get.” I apologized very quickly and asked if he could give me a few seconds while I wiped the coffee off my shirt and pants. Mikko laughed and told me it was OK.

I continued with the call and near the end of the conversation I realized how much easier and more natural the call went than my usual calls. I closed the sale and thought, “Wow, I can’t believe it. Why did this happen? Was Mikko just an easy-going guy? Did I just get lucky?” He isn’t. There’s a science behind this. Actually, I tested it for myself by spilling coffee on myself in the next sales calls and watched as my profits skyrocketed.

So, why did this work? When Mikko saw that I spilled coffee on myself, he instantly felt and thought that I was just a clumsy guy—maybe even on my first day at the job. He probably didn’t think that consciously, but it’s how he and all the other people I’ve tested that strategy on felt. By doing something silly like that, I got them to instantly put their guard down. For the rest of the conversation, they aren’t thinking in the back of their minds, “I’m not letting this guy sell me.” They just see me as a harmless person who’s doing the best he can.

By the way, there were times that I didn’t need to be on video, so I simply told them that I spilled coffee on myself (which happened to work just as well).

Mark Zinder, professional speaker and sales trainer:

I had a friend who sold $300 vacuum cleaners door-to-door in the 70’s. He paid his way through college doing this, and had a 50% closing rate.

My friend would make sure both the husband and wife were present for his demonstration. When he was done, he would turn to the wife and say, “Ma’am, if you could spend 25 cents a day to make your husband’s job easier, would you do it?”

The wives always said yes. He would then turn to the husband and say, “Sir, if you could spend 25 cents a day…”

The husband had to say yes or deal with his wife’s wrath. My friend said he either got thrown out of the house or sold a vacuum cleaner!

Related: Six Closing Lessons From a Traveling Salesman

And finally, we have this incredible tale from a sales veteran who asked to remain anonymous…

When I was in my early ‘20s, I worked for a mortgage company in Massachusetts that covered all of New England. It was an inside sales operation with a call center, and most of the leads were coming to us, because the company had a very aggressive radio campaign at the time.

One day, I got a call from a couple who lived in a different state, who were looking for a refinance deal that would allow them to pull some equity out of their home and get a lower payment. The husband was a police officer, the wife was a really nice lady, they had a couple of young kids—I liked them right away. Plus, they needed the money.

They had everything ready to go, but when the appraiser came out, he said that the paint had to be corrected. Basically, that just meant that it was peeling and not quite up to snuff. But as a result, their house didn’t qualify to be approved for financing in the condition that it was in.

Financing periods aren’t infinite, and we had a hard deadline for this to close. But the paint issue looked like a deal-breaker. Even though they really needed the loan, they were convinced that they wouldn’t be able to get their home painted in time.

That was bad news, because closing the deal meant an extra $4,700 in my pocket that month. With this refinance deal on the books, I was going to level up to another commission tier where all of my deals would pay out more. Failure was not an option.

Another guy I worked with did some contracting on the side, so I borrowed a paint sprayer from him and drove two states over on a Saturday to spend the day helping this family paint their entire house. Fortunately they had the paint waiting for me, but it was an entire day of manual labor, from sunup to sundown.

Keep in mind, we had no idea if this would actually work. It’s not like there was a law against crossing state lines to paint a loan applicant’s house, but I’m not a professional house-painter, and who knows if the appraiser would consider it to be satisfactory or not? We were basically just winging it.

I drove home that night, hoping for the best. A few days later, the deal went through.

Everybody at my office thought it was hilarious. Our compliance officer gave me a bunch of crap because he said I was potentially opening the company up to all sorts of liability, but I think he was half-joking—kind of like, “This is amazing, but don’t do it again.” Plus, I won Employee of the Month, which came with a plaque and a $250 gift card.

I stayed in touch with the family for a few years after I painted their house. Anybody who’s in sales knows that you can form lasting relationships with customers, especially if you’re not just an all-business type of person, and they were kind of blown away by the lengths I was willing to go to help them.

I think the biggest lesson is, “Don’t assume that it can’t be done.” In sales, so many problems that seem insurmountable are less hopeless than they appear. You can always find an outside-of-the-box way to get around the challenge that’s in front of you.


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