December 9, 2023

In his book The Road Less Stupid, Keith Cunningham (entrepreneur, speaker, author, and business guru) suggests that these three questions should be asked prior to making any major business decision:

1. What is the upside?
2. What is the downside?
3. Can I live with the downside?

And I would add a fourth:

4. Can you identify, protect (and even exploit) your 

What is the difference between downside and blindside?

Blindside is the potential downside that you don’t see coming…but there are still ways to prepare for your blindside…which I will explore today (among other things)…with a concrete example.

And in the P.S., I will give you another example specifically for your business of something with 100% upside…no downside…and with guaranteed blindside protection.

But first I want to explore Cunningham’s simple questions which can be the difference between success and failure in anything you do in business, marketing, or in the world of entrepreneurship.

Think about them regarding a current project you are working on (or a business decision you have made in the past) so you can put them to use now (or in retrospect) as you read this post.

My analysis might have some angles that are different from Keith’s…but he is the inspiration for this post today…and I highly recommend his book.

What is the upside?

Here’s where you put on your most upbeat optimistic hat (with a dash of a delusion of grandeur for grins).

What is the best thing you can dream of accomplishing?

I also recommend that while you are dreaming of the millions you will make from your next big idea, you should also tame your expectations as well…that is, make sure you’ve got Papa Bear Upside, Mama Bear Upside and Baby Bear Upside:

Best case, average case, worst case…but all within the category of upside.

And the best case can be Papa Bear or Mama Bear. 🙂

Determining how good it can get…with some tempering of results and emotion…is step one.

What is the downside?

Here’s where you need to be ruthless with your idea…and your feelings.

I would suggest that beginning with your “worst case scenario”—with 100% downside—and should be the opposite of any upside.

Practicing ruthlessness is commonplace for some…and doesn’t exist for others. If you have never practiced it before, it’s time to try assessing downside with ruthlessness…it will be good for you…I promise. 🙂

It’s looking at every aspect of the idea or project asking the question, “what if this goes completely haywire?”

You need to become a nasty and unrelenting secret shopper on the idea, where you secretly break everything inside the idea… to discover what the ultimate downside is before implementing (which is not easy since it’s probably an idea you might be extremely fond of).

I know this sounds harsh…and I mean it to sound harsh…because harsh will enable you to attack the (most critical) third question with as much accuracy as possible…which is:

Can I live with the downside?

Assuming you were as ruthless as possible in identifying the full downside, this question is a bit beyond, “How does it make you feel?”

Feelings are important…even in business…but “living with the downside” also entails all of the financial implications beginning with cash flow.

Being meticulous with this calculation of the financial downside will be the determining factor on a go/no go decision and set you on a road…well… less stupid.

Thanks Keith. 🙂

A real-world example from my marketing career

In the mid 1980’s, during my early years at Boardroom Inc., we had a consumer newsletter (newsletter defined as a publication with no advertising and a higher price than most magazines) called Bottom Line/Personal.

Bottom Line
 was usurping our flagship newsletter, Boardroom Reports, in both circulation and profit…and we wanted to take it to the next level.

At that time, newsletters (as opposed to magazines) were usually sold “cash or credit card only with order,” a model not foreign to today’s online marketers of physical or digital products and services…and at the time, it was how newsletters were generally sold as well.

However, magazines were sold on a “bill-me-later-offer” (i.e., a free issue or multiple free issues followed by a bill should the customer want to continue subscribing).

Magazines could afford to do this for several reasons:

  • If it was on the newsstand already, most knew what it was or have heard of it so getting it into potential subscriber’s hands to sample was the basic first step (rather than a long selling process and asking for a payment up front). They were an aware audience at the jump.
  • They could use less expensive formats such as double postcards or simple letters in basic envelopes because much less “selling” was needed.
  • Because most magazines work on an advertising model, the distribution of free issues helped advertisers get more eyeballs on their ads…yes, eyeballs were a concept well before the Internet.
  • The perceived value of a magazine…glossy and thick (although they are a lot thinner today) was a form of shock and awe (for free) …but I won’t take that aspect too much further. But it is a factor.
  • Over time magazines being sold this way decreased their perceived value (i.e., everyone sold “bill me later” which turned even the most specialty magazines into more of a commodity) …but it was effective (still is) …and there was no turning back to a cash-with-order model.

The model became prevalent in many other industries—try it before you buy it–like financial advisors soliciting new business via group steak dinners or a timeshare company offering a 75-inch TV just for looking at a property.

And then in the digital world, with something like Product Launch Formula (thank you Jeff Walker!) which encourages leading with value, giving away your best stuff up front, because you have lots more “best stuff” behind that.

But all models are meant to be broken when you have the appropriate data. 🙂

Here’s how Bottom Line/Personal broke (and reinvented) the bill-me-offer for a newsletter using the “magazine model.”

One of our consultants at the time said to us:

Bottom Line/Personal, content-wise, is more like a magazine without advertising than a newsletter. And evidence shows that everyone loves it when they eventually subscribe (as indicated by the very high renewal rate) …so why not just give it away?”

Basically, this consultant was telling us to sell the newsletter like a magazine…heresy at the time…but potentially game changing for Bottom Line (and the company).

Looking back on this decision, we went through Keith Cunningham’s “three questions” 30+ years before he put them in his book.

I guess we knew they were coming eventually. 🙂

(If you want to read my tribute to this “consultant” who passed away earlier this year, and he was special, click here and read “Just give it away.”)

The upside was obvious…many more people trying Bottom Line/Personal before they paid for a subscription would add to the pool of potential subscribers (enhanced by our expertise in list selection).

And if the renewal rates were any indication of what the pay up rate would be on new, trial subscribers getting a free issue (or multiple free issues), the economics created a potential windfall under all “three bears of scenarios.”

The downside was obvious too…diminishing the value of a newsletter that prided itself on sharing “consumer secrets” not available anywhere else (and now offering free samples) was risky (at a minimum).

In other words, newsletters were more expensive than magazines because the content was sold as information that is much harder to find.

Another downside was financial…without advertising, the free issues were all cost with no immediate payback of anything.

Newsflash: Paper and postage are not free.

Also, unlike magazines, we would still need to “sell” in the promotion since it was unknown to the public so there would be no savings on copywriters, extravagant formats telling the full, unedited story of Bottom Line/Personal.

Double postcards would not be a workable format.

We still needed 12-page letters and all the bells and whistles just to get them to try Bottom Line/Personal for free.

Simply put, there was no expense cutting available to us on the up-front promotion AND no immediate cash coming in from those promotions using a bill-me-later offer.

But could we live with the downside?

Our calculations said “yes.”

Worst case (on the “feelings scale”) would be a limited (not permanent) exposure to the bill-me-offer, even for an extensive test to prove it was a superior offer through pay up and renewals.

And while feelings are important (regarding the exposure of a free offer of an exceptionally valuable newsletter) it came down to whether we could afford it financially, specifically on a cash flow basis.

Under the worst disaster scenario, we would lose money but not go bankrupt and we would be able to recover.

It was clear that the upside beat the downside by a wide margin…and we could live with the downside.

The test was launched and we never looked back (once we had our results of course).

More on that below.

How to identify, protect and exploit your blindside

This is the additional fourth question I added to Keith Cunningham’s “big three” …and I believe it is relevant here.

We identified our blindside by digging deep to explore what “we don’t know what we don’t know” … a.k.a. “unknown downsides” that might be identifiable… …with the best solution to that being finding the top experts who knew more than us.

Isn’t that a good way to do business anyway?

We protected our blindside by hiring the best consultants in the industry at the time, Dick Benson and Gordon Grossman, who had built some of the largest circulation publications in history (including Contest Newsletter and The Reader’s Digest).

They understood bill-me-offers as well as anyone in the world.

When you don’t know what you don’t know, go to people who know everything about what you are involved in, making sure you can not only identify unknown downsides but learn how to live with them…with all the relevant numbers.

Once we proved that Bottom Line/Personal could be sold with a bill-me-later-offer, we took Dick Benson’s “bogey concept” (i.e., how much can you lose on a new subscription to make your money back over time and under your definition of acceptable profit and cash flow) and we ran with that…with clarity and conviction…and always believing the numbers.

We even expanded the bogey over time (once we had lots of cash in the bank and could afford to lose even more on an initial subscription) …and we also expanded our offer from one free issue to 3 free issues to 6 free issues…with exponential results.

We couldn’t have done any of that at the outset without a “Cunningham analysis” because we would have run the risk of going broke.

That’s why we tested it first. 🙂

But over time, when we were ready to exploit our blindside (once identifying it and protecting it), the results changed the trajectory of the company forever.

Read “Don’t be afraid of the Bogey Man” for more color on how Benson protected our blindside…and the blindsides of hundreds of the best direct marketers on the planet.

And we also ran with Gordon Grossman’s recommendation to build a marketing database, then implemented the most sophisticated regression modelling tactics, which led to the expansion of the “Bottom Line/Personal franchise” (including millions of the best-selling consumer books ever published in direct marketing history).

Read “The real O.G.” to learn more about the magic of Gordon Grossman.

The result was building Bottom Line/Personal into the largest consumer newsletter in America (over 1 million paid subscribers) by first understanding the upside and downside of “giving it away” … and knowing that we could live with the downside.

And once we knew the upside was huge, we were then able to exploit the upside to its full potential by also identifying and protecting our blindside by focusing on what we didn’t know we didn’t know (with a little help from our friends).

As the title of Keith Cunningham’s landmark book illustrates, attacking business decisions in terms of upsides, downsides (and even blindsides if I can add that to the mix), is a brilliant plan of action…and it will guarantee to lead you down a road less stupid.

It doesn’t matter if the road is a super highway or a path in an uncharted forest.

Every road needs a map.



P.S. I promised to tell you about an upside opportunity, with no downside (which you can live with since the downside doesn’t exist!) …and it includes ultimate protection for your blindside if you run any business related to direct response marketing, copywriting, creative services, media buying.


And this opportunity just received an upgrade…which adds to the upside.

2024 will mark the start of the 5th year of my Titans Xcelerator (TXL) virtual and affordable mastermind.

The original group of members who are now heading into their 5th year hold a special place in my heart.

And the fact that they are renewing at over a 90% clip tells me that TXL holds a special place in theirs. 🙂

Since 2019, I’ve gotten to know them and their businesses on a pretty deep level.

Not easy to do with 250 members…but that’s what makes TXL so special…because I make it my business to be interested and not just interesting to those who join.

It’s time consuming but so worth it…and when you’ve got multiple years to create relationships (which no one refunds…they only refund transactions) it’s actually easier than you think.

Every year when someone renews their Titans Xcelerator membership, we send them a special renewal package in the mail.

We also have different names for each anniversary year.

Those who are renewing for the fifth time are our “Titan Legends.”

(If you want to know what we call 2nd, 3rd and 4th year renewals, you’ll need to join to find out…or you can just ask me if you are dying to know). 🙂

I believe that it’s important to commemorate and celebrate someone when they make a wise decision, a decision that has caused massive success in their business.

I believe with zero doubt that joining and staying in TXL is one of the wisest decisions you can make, based on the cumulative success you will experience.

Running TXL isn’t something I need to do from a financial standpoint.

I could have disappeared quietly into the sunset when I left Boardroom/Bottom Line back in 2015.

If I had done that, I still would have stayed in all the masterminds that I pay to participate in because I’m a mastermind junkie…and a lifelong learner.

I spend over $150,000 a year for all the masterminds and groups I am a member of.

It’s never an expense…it’s always a necessary investment.

And my investment staying on top of what is best-in-class in direct response furthers the upside of being a member of TXL.

I will spend money on your education every chance I get. 🙂

Looking back, heading into our 5th year of Titans Xcelerator, there is one word that describes the last five years for me.

That word is Joy.

We have hundreds of members inside TXL who have had transformations inside their businesses because of the people they have connected with profoundly, and all they have learned and implemented.

And I make it a point to get to know every one of them.

It’s one of my favorite things to do.

The fact that I get to have interesting conversations with interesting people within Titans Xcelerator, while helping entrepreneurs sidestep some of the mistakes I have made in my career while building on my successes too…and watching excitedly as the next generation of direct marketers carve out their unique space in their markets…

…is an experience I wouldn’t trade for anything.

In many ways, I feel like the TXL program is just getting started.

To honor that fact, in 2024, I’m going to be making some major additions (“upgrades”) to the Titans Xcelerator program.

We’re going to be doing more cohort-based work together where we focus on implementing marketing ideas in addition to collecting them.

We’ve already begun this with “The Breakthrough Advertising Bootcamp,” “The Overdeliver Bootcamp,” “Profit Partnering Workshop” …with many more to come including the one about “List Building and Segmentation” (which I mentioned in last week’s post).

I’m going to be sharing some of these new additions with you over the next few weeks and months because I’d love to have you join this amazing group so we can work together in 2024.

You can join my cohorts/implementation programs for a fee (a la carte) …but one of the upgrades to Titans Xcelerator is that everything I do going forward is included in your membership.

Upgrades also include discounts on all of the other products and services I offer (for members only) …the ability to “sell what you’ve got” to other members (with an exclusive TXL discount and with integrity) …”open calls” for members to present to the group…and much more.

If you’d like to see what “Titans Xcelerator 2024” has to offer and get a sneak peek at some of the new additions to the program, I encourage you to take a look here and join us.

The upside has no limit.

The downside is non-existent.

Your blindside is protected by having a “de facto Board of Advisors” who have your back for the stuff you don’t know that you don’t know.

It is a marketing insurance policy like no other.

And while it was worth what it cost before the recent “upgrades,” it’s even better now, making Titans Xcelerator the best value of any marketing mastermind in the world.

I’ve researched (and participated in) most of them.

At least take a look here…I’d love to join you on your journey…on the road that is the least stupid.

It’s actually paved with gold (or at least painted yellow) …with wizards of all kinds everywhere.

Click here.

About the author 

Brian Kurtz

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