The Billboard That Got Me The Quickest Profitable Exit

This INTRALINKS billboard outside the Oracle HQ in California paid off BIG TIME. I sold my $.70/share stock for $37/share.

The video landing page from YouTube can be seen here.

I tell my clients that before a liquidity event, I'm the cheapest game in town. But after an IPO or an acquisition, I'm the most expensive. But since we all laugh our way to the bank, they don't begrudge me my profits. Besides, my clients can buy back my stock in a one-year cliff, which means if I don't hit the ball out of the park, then it hasn't cost them a single share of stock. BTW, I did plagiarize the "Kill Bill" movie ad. I wanted to use a "KILL BILL" headline, but the billboard company objected. They said I was putting out a hit on Bill Gates. This billboard went viral with massive numbers of hits. IntraLinks was acquired by a private equity firm, and I got paid immediately. Unfortunately, they wouldn't let my investment ride, and they did a subsquent IPO. Which would have netted me a lot more than $37/share. Selah. Sincerely yours, Rick Bennett Ad Hit Man

The Oracle Air Force

 

First, we had to be ubiquitous. Then, we had to be fastest. Not second-fastest, but fastest. FYI, the 265 transactions per second was the speed record 30 years ago. Today, a mid-rage Oracle system can do 100K transactions per second. Sincerley yours, Rick Bennett Ad Hit Man

Christmas at "The Pirate Cottage"

The Three Wise Men have arrived in my entry way. In my den, across the hallway, you can see (left) my Pirates of the Carribbean skull. And just to the right, on the top shelf of my bookcase, is the Darth Vader Helmet given to me by George Lucas and Gary Kurtz (I have them one of my inventioins). The Wise Men seem at home near my library of inspiration and knowledge. My novels haven't taken off, yet (I'm just finishing #4 and starting #5), but 2026 should be a good year. Hey, I've given Larry Ellison cameos in two of those novels.

Sincerely yours,
Rick Bennett
Ad Hit Man

Convincing Larry Ellison That Advertising Generates Business

 

This was the first ad I did for Larry Ellison. My buddy Ken Cohen had already joined Oracle, and I'd just started my guerrilla-warfare ad business in California. In my first meeting with Larry, he poo-poohed the value of advertising. I told him I could prove him wrong for $600. He took that bet. I said we could buy the front-page box on the lower right-hand corner of MIS WEEK for $600. We spent most of December 1984 crafting this. My contribution was to use the newspaper's font and make the ad look like editorial. Since this was MIS WEEK's first shot at this, they didn't think to put the word "advertisement" on the piece. The result? The phone rang off the hook and Oracle became my client for the next 6 years. Sincerely yours, Rick Bennet Ad Hit Man

Larry Ellison's most memorable one-liner: "The only way ORACLE will ever be delivered to Russia is in the warhead of an ICBM."

No, Larry didn't intend to keep this promise. There are now Oracle offices in Russia. But this one-liner generated billions in sales to the federal government.

I have a whole collection of LJE quotes in my blog at: https://lnkd.in/gxAZNHF4
Sincerely yours,
Rick Bennett
Ad Hit Man

Part II: Helping Salesforce Put a Stake into Siebel's Brain

Remember, Marc Benioff was in the NO SOFTWARE business and Siebel was just in the wrong place at the wrong time. Salesforce had become the number-one CRM company. But more importantly, Salesforce had legitimized the cloud. Why buy and then try to update every version of your on-site software when a cloud provider could do all that AND save you a tremendous on-site hardware/software/staffing investment?

Tom Siebel kind of went unstable when he saw this ad. Several publications reported to me that he told them he wouldn't advertise in any rag that ran such a scurrilous ad. Interestingly, one day we had lunch at Oracle, and Marc told me he wanted to start a salesforce automation company. I thought, hum, just what the the world needs, another SFA company. But my gut told me to bet on the man and not the idea, so I said, "Count me in." Words to live by. You ALWAYS bet on the team. On the day of Salesforce's IPO, Marc sent me a kind note: "You are a great friend, and we could not have done this without you!!!!!" No, Marc, this wouldn't have been possible without YOU. Sincerely yours, Rick Bennett Ad Hit Man

Part 1: Helping Marc Benioff Create the Cloud with Salesforce

Salesforce needed to become #1 in SOMETHING. Siebel stood in the way. But Salesforce wasn't in the CRM business. They were in the NO-SOFTWARE business. Siebel was just a casualty.

Sincerely yours, Rick Bennett Ad Hit Man

Larry Ellison: "I refuse to be out-lied by a bunch of professors from Berkeley!"

Ken Cohen and I ran into Sybase's marketing VP Stu Shuster at a computer trade show, and he shared with us that they had just come up with a distributed SQL query. In a meeting later that day with Oracle's Larry Ellison, we told him of the new Sybase capability. He got very excited and exclaimed, "I refuse to be out-lied by a bunch of professors from Berkeley!"

Over that weekend, I created this ad and shipped it to MIS WEEK that Monday. Larry had the development team (Derry Kabcenell and Andy Mendelsohn) come up with an Oracle distributed query and ship in on the next mag tape for a VAX customer. Thus, we claimed to be the first distributed database. Which was technically true, since Sybase hadn't actually shipped such a product. Sincerely yours, Rick Bennett Ad Hit Man

How Oracle Killed Free Rdb

 Since DEC's VAX was Oracle's bread and butter, we heard they were thinking about bundling it free with every VAX sale. This was an existential threat to Oracle. Here's my ad that headed this off at the pass.

Sincerely yours, Rick Bennett Ad Hit Man

My Headline That Lasted Decades, Killed Cullinet, and the Six-point Type that Landed Oracle a $2-million Site License from Hughes Aircraft

 

My headline that lasted decades, and the six-point type that landed Oracle a $2-million site licence form Hughes Aircraft. I had just seen the movie THE LAST STARFIGHTER and told Larry Ellison I had our next headline: THE LAST DBMS. He loved it and our first ad featured names of database competitors crossed out on the side of a fighter jet. One day, I was going up the stairs for my weekly meeting with Larry and Danny Turano was just leaving and said, "Hey, that footnote landed us a $2-million site license from Hughes Aircraft. They said any company that gutsy gets their business!" The footnote: "Our use of Cullinet, Information Builders, etc. trademarks is the least of their problems. TRBA." BTW, I always signed my ads TRBA for The Rick Bennett Agency. This ad put the last knife into Cullinet. We did get a snarky letter from Cullinet's John Goldman complaining about our footnote. But hey, that was "the least of their problems." Larry just laughed when he showed me the letter. Sincerely, Rick Bennett Ad Hit Man

My Ad That Destroyed Ashton-Tate

 Oracle had a big problem. Ashton-Tate was about to come out with dBASE for Digital's VAX computer. VAX was Oracle's bread and butter. I asked Larry Ellison how many sales we had for the PC version of Oracle. He answered not many. So the answer was to deliver a pile of manuals and Oracle on the PC for $199. We lost money on each sale, but headed off disaster on the VAX.

Ashton-Tate's CEO, Ed Esber, told his people that he "wouldn't get into the gutter by answering Oracle's attack." That killed morale. I imagine many employees called him a gutless wimp as they passed him in the halls. This put a check in Ashton-Tate's swing and killed their VAX initiative. In another post, I'll tell you how I came up with the enduring headline THE LAST DBMS. Sincerely, Rick Bennett Ad Hit Man

My Ad That Destroyed Ask Computer

 

In 1989, Oracle wanted to get into the manufacturing business. I probably had the most fun ever writiing this ad copy. "We Kick ASK" or "We're kicking ASK and taking names." I was interviewing a former ASK employee who was with ASK CEO Sandy Kurtzig when she first saw this. He said she got so mad she cried.

So how did it cause ASK's demise? First, it caused ASK to pre-announce new product capability they couldn't yet deliver. Since they were a public company, it destroyed their quarter-to-quarter profitability.

Second, it a misguided attempt at revenge, ASK acquired Ingres, a competitor to Oracle. Misguided because while Ingres had features unavailable in Oracle, Kurtzig didn't realize that people bought Oracle because it was perfectly compatible with IBM's SQL/DS and DB2. Which meant Oracle customers could dump Oracle and go back to IBM.

One thing led to another. ASK/Ingres was eventually acqired by Computer Associates. In an interview with VANITY FAIR magazine, Larry Ellison commented on the acquisition: "I guess every ecosystem needs a scavenger."

Sincerely yours,
Rick Bennett
Ad Hit Man

Advertising "Hit Man" Recommends a "Hit Man" Movie on Amazon

 

Being an advertising "hit man"—my ads destroyed at least 9 Fortune 500-size companies that I can name—I stumbled on a free Amazon Prime movie last night that I highly recommend. Featuring Bill Nighy, Emily Blunt, and Rupert Grint, this is a real knee slapper.

If you'll remember, Nighy played the naked guitar player in Love Actually. Emily Blunt played in Edge of Tomorrow with Tom Cruise. and Ruipert Grint played Ron Weasley in the Harry Potter flicks. I think this movie is a sleeper that nobody has ever heard of. You want a laugh? You'll get a bunch of them in Wild Target.

@tomcruise, @billnighy, @emilyblunt, @rupertgrint

Why I will never again buy something advertised on Fox News

 

 

Guerrilla Warfare Tutorial

Rick Bennett 

Novelist, Guerrilla Warfare Hired Gun, Lecturer

November 4, 2025

To give credit where credit is due, I learned guerrilla warfare from the late Tony Schwartz, with whom I worked to pass Massachusetts' tax-limitation initiative back in 1980. Tony created the famous Daisy ad that ran only one time on one network and destroyed Barry Goldwater's 1966 race for the presidency (see the ad here).

Whenever I've put on a seminar or dealt with high-tech clients, I've gone in with guns blazing and channeled Tony Schwartz. Sometimes it's worked spectacularly. With clients like Oracle and Salesforce. And sometimes it's gotten me fired. But there are just two fundamental questions I ask to draw out the company leadership and get into what I call "a state of play." Because genius doesn't occur unless you're in a state of play.

Question 1: "What do you do that nobody else can do?"

I have subsequently told them what I call "Ellison's Law." Namely, you are not allowed to say anything in your communications that anybody, anywhere else, can say. This is tougher than you think. The world will pay attention to "the only" and ignore "we're better."

Question 2: "What could a potential competitor do to blow you out of the water?"

I've got some funny stories that will never see the light of day. Many times, I've been with a CXO or Marcom group where they look at me, puff out their chests, and say there isn't such a thing. Then I flash a Powerpoint slide with a hypothetical ad someone might run, and panic hits the room. I am told to delete that slide, any electronic copies that might exist, and to remember that I'm under an NDA and will be sued off the face of the earth if I ever communicate that idea to anyone. Period.

I do my homework before ever taking that first meeting.

The reason I charge for a half-day guerrilla warfare seminar is that I spend some serious time doing my homework. And I won't even accept an advance retainer for a seminar if I can't come up with my own answers to the above questions. Yeah, I have some tools to help me arrive locked and loaded.

Oh, and a final note. Neither me nor any of my subsequent clients have ever been sued for one of my guerrilla warfare forays. Because in the final analysis, hard-core technological intimidation is just undeniably true.