Two years ago, during the “Overdeliver Bootcamp,” when I spoke about “the smartest guy I have ever met in the world of direct mail,” I received many questions…which led to a discussion…and the overriding question was “why was he the smartest?”
Cutting to the chase, the overriding answer was because he knew everything about “this much” (with “this much” represented by this guy putting his thumb and index finger 2 inches apart).
Or he could have said that mastery takes focus, intense prioritization, at least 10,000 hours of “doing it” (nod to Malcolm Gladwell) …and not trying to be all things to all people.
Then I got a question in the Titans Xcelerator private Facebook group this past week from a young member asking where he could find out everything about “subscription marketing” …including books, courses…anything.
It so happens that the previously mentioned smartest guy I have ever met in the world of direct mail also knew everything about subscription marketing too.
He even wrote a book about everything he knew everything about…which I directed this young marketer to…and I will do the same for you shortly.
All of this was worth a blog post two years ago…and it’s worth an updated blog post today.
I called this ultimate expert The Bogey Man…far from a boogeyman…and while he was intimidating to the outside world, he was a teddy bear on the inside (once you got to know him).
He called himself “Timid Timothy” …but he was anything but timid.
He was the boldest thinker of his era.
Richard “Dick” Benson was one of my most consequential mentors…he shaped my early career…and he continues to shape it today with the timeless concepts he practiced and taught.
He also shaped the careers of some of the greatest marketers who were his students: Many were contemporaries…many were competitors (although in direct marketing competition is coexistence)…and many are practicing today at the highest levels of our industry.
I want to share some things I learned from “The Bogey Man” in addition to the importance of always calculating “the highest acceptable cost of acquisition of a customer” (his definition of a “bogey”).
And there is nothing to be afraid of with this Bogey Man.
Unless you are afraid of getting smart. 😊
Dick Benson was a true master when it came to the art and science of direct mail.
For my money, no one could hold a candle to him when it came to discussing anything to do with that medium.
Of course, that also made him the most knowledgeable person I could go to on anything to do with direct marketing/direct response (dead or alive).
First, because direct mail was The Big Kahuna in direct response media throughout his lifetime, well before online marketing was a “thing.”
But also, because the secrets of direct mail (which are only secrets if you aren’t paying attention) transcend all media…including everything online (which Dick never experienced firsthand but you wouldn’t know it).
My relationship with him was pre-Internet so there were far fewer offline media choices to master…but he mastered them all…direct mail, print, package inserts, TV, radio.
Again, with direct mail leading the way.
But if he practiced today, with his lively mind and his diligence and respect for the core principles of direct response, he’d also master every medium online.
Although I don’t necessarily see him doing TikTok videos.
“Doing it” for over 50 years (not Tiktok, just direct mail), and at a high level, made him an expert…the guy had seen every possible test and could comment on any test you were doing based on his experience in the trenches.
And while he was often called a curmudgeon and was known to “never say goodbye” on the phone (he simply hung up when he assumed you were done), he was an awesome mentor.
I learned to embrace his gruff exterior rather than be intimidated by it which made our relationship very special.
Having said that, I could only get so far with him…I always said that I would have been his favorite client had I been a woman…the man was a charmer when he wanted to be, and he was nicer to the gals than the guys.
But you can be sure that he did not discriminate when he thought you had it “wrong”–regardless of your XY chromosome configuration.
All he wanted to do was to educate everyone in his path.
Being that I come from a long line of teachers, I always hated the expression:
“Those who can’t do, teach.”
My experience with Benson changed that expression to:
“Those who did it have an obligation to teach it…and we better listen”
[Nod to Jay Abraham who added the word “moral” before obligation.]
Benson taught from everything he did…both the successes and the failures…with many more of the former than the latter.
As a publisher himself, he launched his own newsletters and made them among the largest circulation newsletters in the health category in the world with the University of California Berkeley Wellness Letter and the Johns Hopkins Medicine Health After 50 newsletters.
That’s how he became THE expert on subscriptions…by creating them at scale.
As a consultant, Dick built Contest Newsletter to become the largest circulation consumer newsletter in America.
I recall the owners of the company buying him a Mercedes-Benz (a big one!) in addition to making him their highest paid consultant—for helping them grow (and then sell) Contest Newsletter at a huge multiple.
He helped my company Boardroom Inc grow our consumer newsletter, Bottom Line/Personal, to over 1 million subscribers…although I can’t say we bought him a new car.
We just paid him a boatload of money, and he was worth every penny.
Benson was also incredibly quotable.
His “31 Rules of Thumb” which make up chapter one of his all-time classic, Secrets of Successful Direct Mail are timeless, eternal truths about direct response.
And as I mentioned during the “Overdeliver Bootcamp,” all 31 apply to every online medium today, whether directly or indirectly.
[NOTE: When you buy my book Overdeliver at OverdeliverBook.com, one of the 11 bonuses is a PDF of Benson’s classic book…and the book is currently out of print.
How’s that for a priceless bonus? And there are more where that came from]
Another amazing thing about Benson was that he never had his clients blindly follow his rules…although he was known to “fire clients” (no matter how much they were paying him) when they did things that violated his direct marketing sensibility and sound business practices he felt strongly about.
He was flexible while being uncompromising at the same time.
Just depended on what his clients were talking about.
Here are some of his rules of thumb…
Benson’s Rule of Thumb #21:
Direct mail should be scrupulously honest
You can substitute “direct mail” with your medium of choice.
Benson’s Rule of Thumb #9:
Self-mailers almost never work
I remember when I challenged him (with some trepidation) about this one…
I told him that in the case of Boardroom’s publications, in the newsletter and book category, a format called “magalogs” (self-mailers on steroids) were hot–and I made my case for using the self-mailing format based on the fact that our products needed a longer sales message and much more education for the consumer about us and our products since we were far from a household brand.
We had mostly used 12-page sales letters up until that time.
These magalogs were often anywhere from 20 to 32 pages long.
His response?
“Self-mailers almost never work. You, however, should test a self-mailer.”
I loved the man because of stuff like that.
[I wrote a blog post after pondering about magalogs and how Benson encouraged us to test them aggressively despite violating one of his rules of thumb…specifically how magalogs were the precursor to online marketing…I need to revive that one for you in the coming weeks]
He was principled but he knew that everything, for the most part, was testable.
That’s why he loved direct marketing so much too…because it’s measurable…and accountable.
He knew the rules and knew how (and when) to break them properly…which goes back to my favorite quote from Picasso, “Learn the rules like a pro so you can break them like an artist.”
I can never repeat that enough.
One of my favorite “Benson-isms” is:
“You have to believe your numbers because they are all you’ve got.”
There are layers to this quote…that is, the numbers need to be statistically significant, they need to be calculated accurately…and you must have a “numbers guru” (Director of Analytics or equivalent) by your side as your most important partner in any direct marketing enterprise.
I remember putting together a promotion for the direct marketing industry titled “Benson Babies Speak” which entailed each of his most famous “students”–a who’s who of direct marketers in the 1980’s and 90’s–touting their most influential “Benson Rule of Thumb.”
You won’t be surprised that the one most important to me was #23 on his list:
“Lists are the most important ingredient to the success of a promotional mailing.”
Today that would be:
“Lists are the most important ingredient to the success of a promotion.”
Please watch my short video, “When 41% is a majority” to see how well Dick schooled me…and many of you know how that video begins and ends. 🙂
I must admit that I was an eager student at his knee since I was a list manager during the time I worked with him…that is, I spent ALL of my time on lists, database modelling and segmentation…and I always made sure that the focus on lists and list research was the highest priority for every promotion we put together.
That led to a highlight of my career.
It happened during one of my all-day visits with him when I only knew him for a short time (and he is the consultant who popularized “the client comes to me”).
Or…the mountain comes to Mohammed:

After discussing dozens of tests, results and new test ideas, he started asking ME about lists for his own products (the health newsletters I mentioned earlier which grew to over a million subscribers each).
I gave him lots of ideas from my experience.
After the day, he simply said:
“Brian…I don’t know you all that well yet…but frankly, I’m impressed.”
Those of you who knew Dick would agree that I probably should have hung up my spikes right there and retired.
But I did decide to go on for the next 40+ years anyway…leading to this post today…and because I had a teacher like him, I am just getting started.
And yes, lists are still the most important component to any direct response campaign.
To bookend this post I will end where I began, when I asked Benson, “How’d you get so smart?” after spending a day with him analyzing every test Boardroom had done over the past quarter and he had a recommendation on every one–and what to test the next quarter.
If you were unsatisfied with his answer which I already gave you, don’t be…and to make it your own and because many of you prefer video learning over text learning, here’s a short video to document it…repeated in 2014, 2016, 2018, 2024…and now 2026 for good measure.
And with that simple phrase (“I know everything about this much”), he taught me the lesson that going a mile deep rather than a mile wide is the most fulfilling way to run one’s life which I teach and implement in everything I do…then and now.
You may differ in your opinion and that’s fine; and if attempting to know everything about everything is your preferred path, I respect you and applaud you for that.
And if that’s the case, you must not get a lot of sleep. 🙂
I’m just not equipped to do that (and very few are).
One specific application comes up when I coach young entrepreneurs inside my mastermind (or anywhere), who don’t think they know anything or feel they don’t belong.
I tell them:
“You know everything about something…share it freely.”
“The Bogey Man” might have scared some folks in his lifetime…he was far from warm and fuzzy…but who needs warm and fuzzy when there are rules of thumb to learn…and finite time to change the trajectory of your business and career.
Warmly (and a little warmer and fuzzier than Benson I suppose),
Brian
P.S. If you are interested in grabbing a copy of Benson’s classic book, Secrets of Successful Direct Mail, you’ll need to buy my book Overdeliver (and note that I don’t make a dime on sales of my book…I’m still working on earning out my advance). 🙂
Go to OverdeliverBook.com to buy the book and you will be able to download Benson’s book in its entirety…in addition to10 other bonuses that are…well…a supreme overdelivery.
If I’m making it sound like the bonuses are better than my book, they might be; but Overdeliver is representative of my life’s work and I am very proud of it…for its timelessness, for memorializing all of my mentors (including Benson…and I’ve got a deep dive into his “bogey” concept in my book)…and for giving me a platform to highlight the eternal truths of direct response.
But the bonuses ARE killer. 🙂
And like Benson’s book, many of the bonuses are not available anywhere but on that page.
They are certainly worth thousands of dollars…and dare I say some of them are priceless.

