Imagine for a moment that the United States doesn’t survive the 2024 elections (I know, not hard) and the resultant chaos plunges the entire world back into a new dark ages.

You know, poor people pushing wooden carts around, snooty aristocrats who never bathe and dress like Humperdinck from The Princess Bride. 

But also, as civilization collapses, we forget all the cool tech and science we’ve learned in the last two hundred years, and our iPhones get repurposed as coasters.

Then imagine some monk studying by candlelight in a dingy abbey in the year 2984, comes across a book containing Einstein’s theory of special relativity stacked together inside a well-preserved academic library (which is why we still need physical libraries).

Assuming people still speak English, the recipient of this little gem might actually be able to understand what Einstein was describing.

Then, BOOM!

The idea first formulated in 1905 might be transmitted over 1,000 years into the future, sparking the next renaissance. We get back electricity. We get back computers. We get back the internet. We get back TikT….Maybe we decide to leave some things in the past.

This serendipitous find would unleash stupendous modifications to human life and our surrounding environment, but in what way was energy transferred from Einstein to our future monk?

It’s not so clear.

Ideas Don’t Follow Physics

Specifically, It’s not clear how the physical effect catalyzed by this revelation is in any way proportionate to the cause. Words were placed on a page a thousand years ago and those words were picked up and read. If the monk had not understood the words, then nothing would have happened, but if Einstein’s idea had traversed space and time to implant into a new mind, then everything might happen.

Alternately, if the monk had picked up a manual for a vacuum cleaner, it might have contained just as much data as Einstein’s paper and the monk’s synapses might have fired in pretty much the same way as he began to understand how to turn it on, how to replace the bag, what countries it was legal in, and where to store attachments.

In both cases (Einstein’s paper and the vacuum manual), a modicum of energy would be used to encode the ideas and a modicum of energy would be used to decode the ideas, but in the one case, nothing in the future changes and in the other the physical world would be upended - we’d be able to unlock stores of energy, communicate around the world, and send people to other planets.

It doesn’t make much sense. It doesn’t sound very scientific.

Because it doesn’t. Because it’s not.

The very concept of an idea is metaphysical. We can’t explain them using the scientific theories at our disposal, in part because those very scientific theories are themselves ideas. Ideas can rock the physical world, but aren’t clearly part of it except in a very tenuous sense. 

You could imagine a tiny chip which encodes 90% of the really meaty human ideas being transported a million years into the future or a billion lightyears across the universe and having a greater impact on its destination than a thermonuclear explosion.

We Know More About the Big Bang Than the Big Idea

And it’s not just the transmission of ideas that’s strange. No one really knows where ideas come from either.

Think of Einstein’s thought experiment about riding alongside a light beam: That little imaginative excursion has had greater implications for 20th-century physics and the progress of modern technology than almost anything else.

But where did it come from? And if you wanted to manufacture the next breakthrough idea for the next iteration in our understanding of the cosmos, how would you do it?

There doesn’t seem to be any formula. Ideas float into our consciousness and float out in all sorts of circumstances for all sorts of reasons.

A methodology for producing ideas would, for instance, need to account for these instances:

• The discovery of cosmic background radiation was made while looking for something else and carefully removing bird poop from the antenna.

• Penicillin was discovered because a petre dish was left for too long and grew moldy.

• The idea for AirBnB came about because Bryan Chesky and Joe Gebbia couldn’t pay their rent without renting out air mattresses.

• The idea for Facebook emerged from the idea of comparing girls at Harvard (which lots of college guys have thought is a good idea).

It’s not like people (or at least scientists and philosophers) haven’t tried to nail down how to generate good ideas. It’s just that every attempt has failed.

As soon as someone starts to get snooty with a new, strict methodology touted to be the only legitimate way to find the next E=MC², someone else cites a counter-example involving hallucinogenic drugs, or a romantic fling, or a job reviewing clock patents, or something which by all accounts has nothing to do with the resultant idea and yet played an indisputable if ambiguous role in giving it birth.

Ideas just don’t seem natural. They don’t seem like they are an ordinary part of our world.

This might be why Karl Popper (the mac-daddy of the philosophy of science) says ideas are actually in a separate world that is distinct from the physical world and also distinct from our subjective mental world.

Whoa With the Philosophy! Why Does This Matter?

Well, that escalated quickly!

So now that I’ve gotten myself neck-deep in philosophizing, what can I say that’s actually useful?

Lots. But I’ll restrict myself to just two points:

First, while we all know that good ideas are a dime a dozen if you don’t execute, we should also know by now that execution requires coming up with more good ideas.

As you execute on the uber idea, you’re constantly facing related problems and opportunities. Often, we approach these lesser puzzles with dogged, heads-down analysis, as if we can just cogitate through every obstacle.

But sometimes, we’d be better off ignoring the petre dish for a few hours or a few days, going for a long walk, having a shower, getting a beer with some friends, talking about anything other than work, reading a sci-fi novel, and getting a good night’s sleep.

“Right!” (you might be thinking) “to sharpen the saw, build physical health, restore work-life balance and focus on self-care.”

Yeah, that’s important too, I guess. 

But mainly because very often the activities tangential to action (parallel to analysis) are where breakthrough ideas are born - where the magic happens. Plus, when you come back into the lab, you may find something great growing by accident in your petre dish.

(or it could be that if you chain yourself to your desk for a few months, that is what will generate good ideas, but since no one knows for sure, you’re free to try more diverse and pleasant alternatives).

Second, for all you engineering types who just want to build the widget and get annoyed when some product manager or sales guy oversimplifies your creation to fit it into the brochure, remember that the transmission of an idea can have as much or more physical, objective impact on the world as the initial implementation of that idea. 

In other words, your single pulsing light can go bleep, bleep, bleep as you code alone or - if the idea of your app can be made simple and sticky - the whole universe can be set aglow. You choose.

Supernatural?

It’s crazy how ideas are formed and it doesn’t make any sense how much matter and energy is moved when someone is moved by an idea. Yet nevertheless, the world of ideas has more tangible impact on the physical world than anything else. 

Ideas are clearly super. And I have my doubts as to whether they are natural.

Jensen Huang, said in a recent interview with Wired Magazine that “Strategy is storytelling.”

Nice soundbite. But what did he mean by that?

Before I try and take the proposition seriously, I might as well admit that he could have just needed something to say to the journalist. Good for you Jensen! Way to come up with alliteration on the fly.

But I tend to think the offhand statement came from somewhere deeper in his past experience and the reason he could trot it out so casually was because it was well-worn from frequent use.

If we pretend for the sake of argument that strategy really is storytelling, then where does that lead us? Because other than their shared “S,” Strategy and Storytelling don’t seem to have much in common.

A corporate strategy is, after all, a plan - a map from point A to point B. It takes inventory of the company’s resources, measures the inputs and outputs of current and future iterations of the business model, proposes new versions and and products to take advantage of new market opportunities. Strategy is a technical, mathematical, analytical endeavour aimed at quantifying the unquantifiable future and knowing the unknown with enough fidelity to make it real. If you’re building a strategy, then you’re engaged in picking out and making possible one particular scenario out of the myriad potential versions of tomorrow. You’re not just making stuff up.

Strategy building sounds much more serious and important than storytelling. It sounds like something you’d do in Excel not Word. In a way, strategy and storytelling seem like opposites. Strategy must be realistic, thorough, and empirical while storytelling (at least as we usually think of it) is limited only by imagination and creativity. You probably wouldn’t want your accountants getting creative with the books and you probably wouldn’t want your CEO getting creative with the strategy.

Or would you?

The Mission is the Boss

Another Jensenism is “The mission is boss.” This pithy statement fits our preconceived notions a bit better. If you happen to work with a few dozen or a few thousand smart, hardworking, analytical people, then it’s far more motivating and empowering for them to work for a mission than to work for a boss. A boss may have a few good ideas, but a mission requires your ideas. A boss may give you a list of to-dos, but a mission requires you to come up with your own lists. A boss requires you to punch a clock and do what you’re told, but a mission requires everything you’re capable of.

The thing is, a mission is just the ending chapter of a strategy. It describes the future as it will be one day, as we can make it if we each do our part. But if “our part” is strictly defined from the top down by a single person, then it not only stifles enthusiasm but also limits the scope of analysis. In this way, rigor and precision on the part of the leader in dictating the details of a strategy actually limits the rigor and precision applied to the strategy as a whole.

Huh?

Let me explain.

No leader, no matter how prescient, could possibly describe a strategy in as much detail as the imagination of every one of her employees. For the same reason that the Soviet planners couldn’t accurately predict and direct supply and demand as well as the free market could, the CEO can’t predict and direct all the elements required for a strategy to succeed. In order to apply analytical rigor to every level of the strategy, she has to engage every member of her organization so that they are predicting and directing their own small (or large) part of the whole.

The problem, of course, is that if strategy is completely open-sourced to all of a company’s employees, then the result is likely to be full speed in all directions. Every employee is going to have a slightly different take on where the company should go and if the company tries to go all those places, it’s likely to stall.

The way to thread this needle between the need for focus and uniform direction and the need for individual creativity, analysis and engagement is to turn your strategy into a story.

A Mental Model - That Grows With the Telling

Because a story is an idea. And an idea is a mental model which is passed from mind to mind in a way that actually increases the fidelity and nuance of the model. A handsome young president can tell a story about Americans going to the moon and how doing so will prevent world war and seven years later, the minds of thousands of people put to work through the medium of space and time can turn this small step into a giant leap.

Without a story, a strategy is just specifications. In his memoir “Surely You’re Joking, Mr. Feynman!”, the Nobel-winning physicist Richard Feynman tells this story about working with a group of young engineers recruited to the Los Alamos project who were lagging behind:

The real trouble was that no one had ever told these fellows anything. They sent them up to Los Alamos. They put them in barracks. And they would tell them nothing.

[...] I said the that the first thing there has to be is that these technical guys know what we’re doing. Oppenheimer went and talked to security and got special permission so I could give a nice lecture about what we were doing, and they were all excited: ‘We’re fighting a war! We see what it is!’ They knew what the numbers meant. If the pressure came out higher, that meant there was more energy released, and so on and so on. Now they knew what they were doing.

Complete transformation! They began to invent ways of doing it better. They improved the scheme. They worked at night. They didn’t need supervising in the night; they didn’t need anything. They understood everything; they invented several of the programs we used.

[...] As a result, although it took them nine months to do three problems before, we did nine problems in three months, which is nearly ten times as fast.

The moon landing and the atomic bomb were arguably the two biggest and most ambitious engineering projects in human history. The strategy for both was a story. The story had details, of course. It wasn’t pure imagination. But the story was the unifying idea - the mental model - shared by thousands of people which deepened analytical rigor and motivated action.

Your Market Tells The Story

Even customers take part in the story - in propagating and enriching the idea. I remember clearly the feedback we gathered from Bloomberg in 2004. They thought our product was more secure than the competition’s even though our company was 1/100th the competition’s size. It hadn’t really occurred to us before that, but we retold the security story to ourselves, scoured the details of the market, and began to focus on how to make our product even more secure. With every retelling, the story got better and better until we were selling to The US Air Force, the Federal Reserve Bank, and American Express.

It is possible (like early in the Los Alamos project) to get people working on a strategy devoid of story - a strategy which is just specifications and “tell them nothing.” But unless and until the the strategy can be shaped as a story so that it passes from mind to mind in an ever-expanding network of interlaced details, it will remain inert and lifeless.

Strategy is storytelling because strategy must be shared across the minds of tens of thousands of people: employees, partners, investors, customers. Otherwise, there’s no way it can encompass all the myriad details it will encounter out in the wild. There’s no way a single person can create the specification for future success, but a single person can tell a story that grows deeper and more meaningful with every retelling.

I like coffee.

Like a normal person.

And I particularly like Kicking Horse Coffee, roasted in the Canadian Rockies not too far from where I live here in BC.

Their packages used to have a little dashed line where you were supposed to cut it open and a little twist-tie-thing that you could use to seal it.

Then they changed things, removed the wire, and now instruct you to “peel to open.”

Problem is, unless you’re Brian Shaw, you can’t actually just peel to open. On average, it took me two or three minutes of hand cramping effort to pry it apart and about half the time, I ripped the package in the process.

As a grown-ass man, it’s a matter of some pride that I can both follow instructions as well as separate two pieces of paper joined only by glue. But after a few rounds over a couple of months as my consternation grew, I finally decided to just cut the packages open…And send a whiny note to Kicking Horse Coffee’s customer service:

“Have you ever tried to open your new ‘peel to open’ packaging. I can do fifty push-ups but half the time I give up and pull out the scissors. Do you really want your customers mad at you before they drink your coffee?”

A bit excessive? A bit snarky?

Probably. But I considered it my civic duty.

Because first of all, think of all those grandmas struggling for hours to peel the package and get their coffee - growing sleepier and sleepier as the day goes on - unable to open the package and unwilling to break the rules and just give it a snip.

This is for you, Mama Mac!

And secondly, packaging really is part of the message, and Kicking Horse needed a swift kick to tell them that the first little message they sent was that you couldn’t trust them.

It says right on the packaging that their coffee kicks ass (I’ve tested this claim, and it is absolutely true). But it also says on the packaging that you should “peel to open” and that message is a pernicious lie. The problem is that to validate the “this coffee kicks ass” message, you have to get through the “peel to open” message. Which means you’re already sweaty, exhausted, and grumpy before you get your first sip of joe.

I could be overreacting. That’s sort of what Kicking Horse’s customer service rep implied in their reply:

Hello there,

Thank you for reaching out!

I’m sorry opening our bags may have you puzzled. They are tough at times to simply peel open, but for good reason (psssssst…it’s all about freshness). You’ll want to make sure you use scissors to cut open the bag if you encounter a challenging easy peel. We know it's not always consistent, and we continue to work on improving that.

We have also made the decision to remove the tin-ties from our packaging, but with nothing but good intentions. In all honesty, tin-ties really aren't great for the planet. The tin-tie isn't necessary, it's convenient, but not necessary. So, we’re simplifying and cutting our ties with the thing called the tin-tie. 

There are loads of ways to keep coffee fresh after the package is opened. Chip clips, binder clips, heck, even re-using broccoli rubber bands. Jars or any tightly sealed container are also really great options!

Wishing you all good things,

Cheers!

They are right of course. And I feel duly chastened. I’m sorry for complaining about the tin ties. That’s a good point about broccoli bands, I hadn’t thought of that.

But in the back of my reptilian customer brain, I still think they should just fix the package and make it pleasant to open. Even the “psssssst” reminds me of what the package should sound like when I peal to open. My experience of their coffee starts at the grocery store, ends with the last sip, and in-between everything plays a part in my overall feeling of satisfaction or dissatisfaction.

Unboxing Apple

Moving up the tech stack from coffee to computers, Apple was the first computer manufacturer that gave a rip about their packaging. Opening a Dell or an Compaq was like opening any other household appliance: same bland cardboard box, same tape, same lifeless blocks of foam, same layers of generic bubble wrap applied in the same way. You couldn’t tell from the unboxing whether you’d bought the $800 refurbed budget model (with the flickery screen that gives you headaches) or the $6,000 zillion-core gaming monster with enough RAM to keep all your apps open at once.

But Apple Thinked Different. And you could tell from the first moment you unsealed the first seam. Those little tabs that helped you grab the edge of the tape, the thin, custom wraps around the cordage, the nested composite molds around the power adapter, the film gently sandwiched between the screen and the keyboard with the clear yet subtle color-coded indicators telling you where to pull to remove it: all of these details sent little signals to your subconscious that this was a premium product carefully crafted in California by designers who cared about each bevel and each pixel.

Opening a Mac (or later, an iPhone or an iPad) was like opening a Tiffany’s blue box. You were pre-excited and pre-impressed and pre-delighted with your purchase before you even turned it on.

But what if you’re pitching SAP middleware? What if your product isn’t physical and doesn’t have a package?

Every product and every market is a little different, but the same principle applies. Your customers’ (or investors’) experience starts before you think it does and includes many elements that you’re probably not thinking about. You may not use “packaging” in the normal sense, but you’re sending subtle signals well in advance of and peripheral to the hands-on use of your product or the core of your pitch.

Here’s just a few examples of poor packaging:

• You show up late for your first meeting with an investor

• You blame your co-founder (or spouse, or dog, or developers) for the product outage that left customers in the lurch

• Your Google ads promise something your landing pages don’t reference and your product doesn’t even do

• Your customer service line just keeps ringing

• You’re pitching slides you’ve obviously never seen before (because the intern built the deck)

• When an investor calls your “biggest customer” it takes the customer half a minute to remember she bought your product

• The step in your on-boarding that says “verify your email” doesn’t actually reference an actual email in the prospect’s inbox

• You wore a mesh shirt to the meeting (true story, we had a developer show up to his first job interview in a mesh shirt, but he was so obviously brilliant, we hired him anyway…every rule has an exception)

None of these details are the pitch or the product, but all of them are part of the packaging. Every detail at every step, every way someone brushes up against your company, is part of your positioning in the market.

It is very true that some of these details matter less than others. If the coffee’s really good, even picky, entitled millennials like me will snip through the instructions to “peel to open” and keep buying. Likewise, people bought a lot of HPs and ThinkPads regardless of the clunky unboxing experience. But overall and at the margin, even the little details make a difference in the impression you create for your audience. I may be able to logically distinguish between my feeling of consternation about a clunky coffee bag and my enjoyment of the bag’s contents, but most of the time those impressions are mixed up and I don’t have the time to separate them.

If your product sucks or your pitch is garbage, then no amount of packing and peripherals are going to help matters. You’ve got to get the core in good shape. The coffee has to taste great. But assuming you’ve built something worth investing in, don’t ignore the package; it changes your positioning more than you might think.

If you’re here, maybe it is. 

“Marketing” and “Manipulation” both start with “m” making a meaningful mental model where there’s really just a shared consonant. Your brain tells you there’s something important about the fact that the two words are alliterative. But really they just both start with “m.”. . and that’s it. That’s all. 

And what’s with the hanging question in my title? Why can’t I just answer it? Why can’t I just add “Yes!” or “No!” or “It depends on whether you’re selling Kale or Coke,” or something that doesn’t leave you in suspense feeling like you need to read a blog post to resolve the tension you feel? It might save us both a few minutes of valuable time.

It Totally, Definitely Is

I might as well admit at the outset that sometimes (often? usually?) marketing is manipulative. It sets up a situation in your mind that can’t possibly be true in reality in order to get you to buy something you don’t need - or even want. A lot of beer, cigarettes, and enterprise software has been sold this way by unscrupulous marketers looking for any possible way to get customers to part with their money. 

Will beautiful women really want to be near me if I smoke Camels? Is the migration to Oracle’s database really going to be “seamless?”

Absolutely not. But the ads make you feel that way by deftly intertwining ideas and images until you think Clydesdales and Christmas have anything at all to do with cheap beer. Just because the ERP vendor found an honest-looking customer with a fancy engineering title who (for the low, low price of a week at the Four Seasons and box seats to the Braves game) was willing to say nice things about them doesn’t mean everything she says is gospel.

Except When It’s Not

Funny thing, though. I’ve been working on positioning tech (among other things) for twenty years now and when you get the message right it feels a lot less kitschy and manipulative than when you get it wrong.

Here’s the tell: when you get messaging wrong - when you’re really just pulling the manipulative levers - you don’t want the customer to ask any more questions. Because as soon as you have to explain why supermodels and nicotine go together the gig is up. It’s clear to everyone that your marketing was just a skin pulled over the alien cockroach of your product.

On the other hand, when you get the marketing message right, you want the customer to ask more questions, because the simple, digestible, red pill of your top-level market position leads to a whole matrix of additional supportive details. The further the customer digs, the more she digs your product. The more she finds to support and expand your simple nugget of a tagline. If the customer keeps tugging on the thread, then she soon finds a whole garment - which, if she’s dressed like most women in beer ads, might be quite useful.

The difference between ethical and manipulative messaging is a question of honesty. Does your product really, truly deliver on the promise you make, such that you’re willing - eager - to expand on the details or do you feel the need to get hand-wavey about the product behind the green curtain. If a customer has the gall to probe what you mean by “Custom AI Model” even though it’s scrawled all over your homepage, do you feel the least urge to obfuscate?

Dull and Honest?

Good marketing messaging is honest, but that doesn’t mean it has to be dull. In fact, it’s a disservice to customers if it is. It’s a disservice not just because it’s boring but because it won’t get read which means a good product (a product which could solve a real problem) won’t get used or won’t get used properly.

Let me unpack that.

If you, as a marketer, set out on a quest to make your messaging as prosaic as possible - just the facts, ma’am, just the bare, unvarnished truths without any attempt to pretty them up or make them a little more appetizing or interesting - then you might be honest, but you’d also be insufferably dull. Dull, even if your product is exciting.

For example, here’s the un-sexiest pitch for Strava I can come up with on short notice:

“We let a person who likes biking do data entry to add a personal profile and track rides, and then connect that profile with other people’s profiles who like biking.”

Wake me up when you’re done talking.

Or VMWare:

“Operating systems can run on our software as if it was hardware.”

Hmmm…Yeah…it’s hard to describe VMWare without it sounding cool.

I’d like to think the reason I’m having a hard time coming up with dull pitches is some innate ability, but the reality is that language is inherently lively and the use of a cool product is inherently engaging and interesting. When you combine them, it’s almost easier to create interesting, lively messaging than dull, strictly-factual messaging.

And the remarkable thing is that lively, interesting marketing is also better for the customer. It’s better because it engages the customer’s imagination and creativity and spurs him on to take action toward his goals.

The Dawn of Marketing

To illustrate, let me go waaaayyy back in the history of marketing. Imagine you were marketing a round stone to a primitive tribe. 

You could just keep things dull and factual: 

“Here’s a heavy object which is perfectly round.”

Or you could suggest use cases and benefits:

“You can roll it on a flat stone and grind grain - feeding your family.”

“You can chip holes in two of them, put them on a strong, straight stick, and use them to roll heavy things from place to place - giving you mobility.”

“You can use a big one as a secure door for your cellar - keeping out bears, badgers, and other critters.”

You might think these use cases would be obvious, but think again. People spent thousands of years using millstones before they started using wheels even though you’re literally, factually, rolling a wheel when you’re grinding grain with a millstone. The bow and arrow (a pointed stick on another stick with string) was invented thousands of years after the spear (a pointed stick), even though people had been staring at all the ingredients the whole time. 

It took people a few thousand more years to figure out that the pleasant, twangy sound your hunting bow makes when you pluck the string might really turn into something someday.

The difference between rolling a millstone and rolling a primitive cart?

Marketing. And a little engineering. 

If only some primitive marketer could have made a cave painting of millstones on an axle, we might have those flying cars by now.

Because marketing, when done honestly and ethically, doesn’t manipulate in the negative sense we usually use that word. Rather, it makes what’s possible both plausible and engaging. It plants an idea that leads to solved problems and real, material benefits for your customer.

Good marketing is simple, intriguing, and emotionally resonant, but it’s also honest, helpful, and genuinely insightful. If you want to get technical, then in the strictest sense of the word, even good, ethical marketing does “manipulate” in that it moulds, directs, and changes our thinking, but it does so in a way that helps your customers feed their families, gain upward mobility, and maybe even kill the mammoth that was trying to kill them. And if that’s manipulation, then sign me up for it.

The Canadian federal government has proposed a tax hike on capital gains. Previously, you were taxed at the ordinary income rates but on only half of the gain. They’re proposing increasing the inclusion rate to 2/3rds of the gain for earnings above $250k.

As you can imagine, many people are not happy. And as you can also imagine, many people aren’t terribly sympathetic to the 0.13% of high earners who will pay more taxes. After all, no one can whine like a bunch of rich people who will still be rich after “suffering” through what they are whining about.

Taxes are Prices

But stop thinking about this as a tax increase and start thinking about it as a price increase. Because that is what it is. Taxes, after all, are just a fee that you pay for working or for investing or for buying stuff:

• You want to get a great job and earn lots of money? Well, it’s gonna cost ya. More and more the more you make, up to 53% of what you earn here in BC.

• Want to buy a rental house, fix it up, and sell it six years later for double what you paid for it? That’s got a price too - which just went up. 

• Want to buy products or services? There’s the price of the item and then there’s the price of the transaction - the price of the sale. In BC, even used cars include the price of sales tax, so over enough sales, the price of the tax might be more than the price of the vehicle.

• Heck, there’s even a price of owning your house which is separate and distinct from the total costs of owning and maintaining your house: property tax.

If you don’t believe taxes are prices, then try not paying the tax. You’ll be treated like you stole something. Like someone who bought work but didn’t pay for it.

Prices are Messages

So if taxes are prices, then what do prices do? Prices are incentives or disincentives. Prices are signals. Prices are messages that tell you what to do and not do with your time and with your money.

The message might be about the quality of the item (a Rolls Royce), its scarcity (a diamond ring), or about how much demand there is for it (seaside cottages in La Jolla). The messages prices send help us to make decisions between competing alternatives.

Part of the reason prices function as messages is that most of us don’t go through life calculating all the prices of everything in real time. We’re not quite sure whether we should go to McDonalds or Ruth’s Chris, but we’re darn sure we shouldn’t be ordering Kobe T-Bones at $75 per oz.  We’re constantly making mistakes - making un-economic decisions - but over entire populations of us wacky creatures, these messages have an impact which affects our collective actions.

Governments don’t think about taxes as prices which convert to messages. Governments would rather believe that the prices they impose on activities and goods don’t affect their attractiveness or unattractiveness. They’d like to be able to send clear, definitive messages in the form of taxes (prices) and have people completely ignore those messages and go about their work or their business as if they didn’t hear or didn’t understand.

But people hear. And People understand. They can look at the price tag and figure out whether it’s a good deal or not. They get the message.

The Message of Increasing Gains Taxes

The problem with increasing taxes on capital gains is that you’re increasing the price of investment. Since an investment by its nature is risky and might not work out, the imposition of an increased price on the reward side of the spectrum moves every investment a little closer to the “not worth it” category.

Imagine a scrappy twenty-something who managed to buy a second home as an investment. She puts in a couple years of nights and weekends painting baseboards and remodelling bathrooms, and then decides to sell the home to repay herself for all her hard work and risk-taking. The capital gains tax she’ll pay on the sale is part of the price of her investment and if the price is too high, none of what she’s done makes any sense. She should have just waited tables or just enjoyed her free time - it would have been a better risk-adjusted return.

Or imagine my dad, who moved our growing family 12 times in my first 18 years, fixing up house after house with his own two hands while we lived in it, and then sold each house at a “capital gain.” He wouldn’t have triggered the $250k threshold, but that’s not the point. The point is that his willingness to take risks and invest was driven in part by the price of investment. His behavior was not independent of incentives and disincentives. He was listening to the messages which prices and taxes sent. He could read the tax brackets just like he could read the price of 2x4s at Lowes.

We may have a hard time empathizing with fat cat VCs and hedge fund managers, but their willingness to invest is affected by the price of investment too. If the price of investment is moved higher, then - at the margin - they will invest less or invest elsewhere.

Good riddance, you might say, but hold on. A bunch of poor upstart entrepreneurs like me (who grew up in 12 houses) or my business partner (who grew up with two parents and three siblings in a house with two bedrooms) would never have gotten off the ground were it not for VCs and rich investors who saw potential in our youthful energy and good ideas.

I’m the one considering investing in startups now among other ways to spend or save money. The tables have turned, but the equation is the same. When you’re considering an investment, you can’t ignore the price (the tax) any more than you can ignore the risks.

I’m no economist, but I think we want more investment not less. We want more investment because more investment creates economic growth. It helps to fix up broken down houses and launch new businesses which employ more people - and the cycle continues. It might strike some as unfortunate that low gains rates allow the rich to get richer, but I’m ok with that as long as the rich are still willing to invest money in poor young entrepreneurs.

I’m not opposed to taxes generally because I am in favor of national defense, clean streets, and the rule of law, and I’m not convinced by my more-libertarian friends that the private sector can deliver those collective goods. But setting the price of investment in Canada higher than it already is reduces the incentives and resources for pretty much the only activity which can create economic growth.

Increasing taxes on gains increases the price of investment, and this sends a clear message to investors of all stripes that the federal government of Canada wants you to stop investing quite so much.

Daniel Kahneman passed away March 27th at the age of 90. He was a psychologist who received a Nobel prize in economics. His monumental work Thinking Fast and Slow has influenced my thinking on messaging and positioning as much as any other book except for a couple written by Al Ries (the godfather of positioning). This, even though the book is not about marketing.

Kahneman’s core insight is that our thinking - our psychology - is not one-dimensional. Human’s vacillate between two different modes of mental assessment depending on the nature of the problems we encounter. Sometimes we choose the right mode for the job and sometimes we don’t. Anyone who hopes to communicate complicated concepts effectively to their fellow humans has to work within the capabilities, predilections, and limitations of these two ways of thinking.

Here’s the model Kahneman lays out.

Thinking Fast

In most circumstances, we think fast. This is because we’re constantly scanning our situation with our eyes and our mind and our brain fires a billion neurons at once, allowing us to react with the speed of recognition to most challenges. 

If you’re hurtling down a trail on your bike and a big dog jumps out of the bushes, your brain crunches all the numbers and tells you what to do. It tells you whether the dog is mean, it tells you whether you can stop in time or must swerve, and it also tells you whether you have room to maneuver. In these situations, we often find that our reactions pre-dated any conscious thought. Whatever decisions we made in the instant were made as much by our body as our mind.

If your wife walks in and notices the new widescreen TV you’re installing in the living room, you can tell in an instant whether she is pleased or irritated. You don’t have to wait for her to fill out a form, list her emotions, or calculate her level of agitation. You just recognize intuitively what her face and body are telling you and you prepare for fun, flight, or fight accordingly.

If you’re an expert in jiu jitsu or gymnastics, your brain tells you when your body is in the right position to execute the flip, throw, planche or pin. You don’t need time. You don’t need a committee. You don’t need a spreadsheet or a calculator to tell you these things. You just know, and you know in an instant.

And Slow

On the other hand, if I ask you to calculate 485 x 382 in your head, then you flip into a different type of thinking entirely. You don’t recognize the answer like you recognize an old friend. You must deliberately analyze the question and deliberately calculate the answer. It’s a slow, laborious process. It takes you out of the moment; it narrows your intake of new perceptions until you have determined the solution to the problem.

We encounter many problems solvable by intuitive thinking, but also a fair number which can only be addressed by slow deliberate cogitation.

Estimating the materials, labor, and subcontractor costs for a large construction project isn’t a job for intuition. The precise gravitational pull of the moon on a spaceship isn’t something you can learn to recognize to a sufficient decimal place. Auditing your company’s financials should be done deliberately unless you want to feel the whiplash of math to the face.

Which Speed?

Both fast and slow thinking have their place. Both are indispensable. If you had to have pen, paper, a manual, and a calculator to know how and where to throw a baseball, then you wouldn’t win many games. But very few lithium batteries have been designed by intuition.

We try to resolve most of our problems at the level of intuition because it’s faster and easier and only drop into deep contemplation when absolutely necessary. This often creates problems because we begin to develop inaccurate intuitions - we try to solve a slow-thinking problem quickly.

Kahneman gives unending examples of this mismatch. Our fast thinking seeks out narratives and even invents narratives that aren’t there. When our brain finds a story - a cause - then it often ignores everything it knows about statistics and logic. When you hear something growling in the bushes after reading a book about bear attacks, then your brain jumps to conclusions even if the bush is in Central Park and it’s a billion times more likely to be anything other than a bear.

Marketing Fast and Slow

When I read Thinking Fast and Slow years ago it was a revelation to me (I’ve since read it two or three times cover to cover). The model Kahneman provides explains so much about how we perceive and process our way through life. It explains how experts are able to make snap decisions that are sometimes startlingly accurate and how fancy pants Ivy League professors in statistics can be fooled into thinking a character profile works as a librarian even when they know almost no one works as a librarian.

The two-mode model of thinking also explains how people respond to marketing messages and why some messages work and some don’t.

Step One: Math

The most obvious mistake many marketers and entrepreneurs make is to demand that their audience think slowly right off the bat. Many messages for many products (especially highly-technical products) read like a math problem. Even if your audience is technical, these types of messages usually bounce off. It’s not that a VP of Engineering can’t understand what you’re saying, it’s just that she’s not yet decided whether deciphering your message is worth the effort. Her default is to ignore and move on, only diving into deep, laborsome analysis if it feels like it’s worth the time and effort. She has to like the story to be motivated to do the math.

A Face I Don’t Know - And Don’t Want To

The next mistake is to construct a message which is easy to understand but which contradicts something your audience already knows. In this case, the customer’s intuitive response is to be repulsed by the message rather than drawn in - as if your message is an angry, unfamiliar face amid a crowd of faces. If you’re telling me, for instance, that sales teams don’t use enough technology or that your cloud service has more features than AWS, then I probably won’t feel the need to investigate further. My intuition tells me you’re wrong and I don’t feel like thinking hard to test my intuition.

Practically Worthless

The third mistake is for messaging to appeal merely to practicality, “ROI,” “shareholder value,” “30% savings,” or some such businessy outcome. This is, of course, more common with B2B products. I may think the message is plausible - it has the ring of truth - but not really care at a personal level. It is eminently possible for the CFO of a large bank to feel no emotion at the prospect of saving his institution millions of dollars. And unless he cares - unless he feels something when he reads what your product can do for him - he’s unlikely to act. The CFO’s knee-jerk assessment doesn’t provide him sufficient motivation for further action - the analysis, discovery, and calculation necessary to justify your solution. In this case, your audience understands what you’re saying and they aren’t actively repulsed by it, but neither are they drawn in. They just don’t care.

The Rest of the Story

A familiarity with Kahneman’s twofold model enables you to thread your positioning through these errors. It’s a uniquely empathetic understanding of the way people think that can help you meet your audience where they are and bring them where you want them to go.

People think fast and intuitively at first, seeking out narratives that they care about. So go with the flow and conform your opening pitch to how people actually think vs how you want them to think. Say something about your product or company that engages your audience in a narrative they want to take part in. Then once they’ve chosen to be characters in the story, later on you can ask them to slow down and do some math.

Even if you sell ERP middleware, your audience is looking for an intuitive entry point into your product’s capabilities. They’ll do the difficult research and calculations only if you can interest them in a story of how your product is the dwarvish sword which will enable them to slay the dragon of roguish pivot tables, endless deduplication, and missed alerts, leading to the adulation of their fellow townspeople. 

Another way of saying this is that your audience has to understand the story, like the story, and see themselves in the story in order to motivate them to hear the rest of the story.

That’s just the tip of the iceberg. That’s just one of the dozens of sparkling insights from Thinking Fast and Slow, many of them similarly helpful for those of us trying to communicate ideas. So Rest in Peace Daniel Kahneman. And thanks for helping us to understand each other.

You’d think positioning would be easy if your product tasted like bacon.

But according to a recent Wall Street Journal article, consumption of pork is declining and no one’s sure what to do about it.

Part of the problem might have been thirty years of positioning pork as:

“The Other White Meat”

In other words, pork is more like chicken (white) than beef (red).

Ok, great.

So pork is cheaper, blander, and easier to cook than beef and you should buy it when you’re tired of eating chicken? Is that the idea?

Yeah, sorta.

And the campaign sorta worked. I mean, after all, pork is more white than red. The slogan appealed to an attribute of the product which is as clear as red and white.

But beyond that surface-level authenticity, the positioning didn’t have much sizzle. It didn’t give you a unique reason to include more pork in your diet other than just…well…it’s the other white meat if you’re dying for a change.

This highlights a key issue to consider when positioning anything - whether protein, products, people, or venture deals. You must position on an attribute people agree on, but you must also be very careful choosing which attribute or else you may find yourself down a dead end street.

The problem with “The other white meat” is both that it pegs the maximum size of the pork market to a subset of that of chicken and that it is non-descript - the one attribute it highlights doesn’t provide much incentive to keep reaching for pork.

A Different Way to Cut It

But it’s easy to criticize. What would have been better positioning for pork?

Let’s start with the most blatantly obvious fact in the universe: bacon is delicious. 

Some people would dispute this claim, but those people are wrong…and shouldn’t be trusted.

Bacon is also mostly eaten for breakfast... Oh! Along with sausage! Now we’re getting somewhere. And no, turkey sausage doesn’t count, and don’t even get me started on turkey bacon.

Bacon and sausage go with eggs and pancakes like peas go with carrots. It’s a match made in hog heaven.

So pork already has a corner on the breakfast end of our meat diet. When was the last time you had chicken wings with your oatmeal? Maybe you eat steak and eggs at the truck stop every now and then, but not every day or every week.

This might be true and still not help the pork industry much. Maybe the breakfast market is already saturated. Perhaps there are ways to convince people to trade out more of that granola and yogurt for something that’s a bit more finger-licking good, but it might be that pork has tapped out the breakfast market and needs a new opponent. Maybe you can’t get enough paleo crossfitters to make breakfast a growth market.

Consider, though, people’s mental associations with bacon, sausage, and breakfast in general. For many people, a big breakfast is their favorite thing ever. Maybe they don’t get to eat bacon and eggs every morning, but on Saturdays when they have time, how great is it to throw a slab on the frying pan and anticipate the savory, crispy, juicy, semi-spicy-sweet goodness of a couple (or six) strips of bacon and few links of sausage?

Those are powerful associations. Way more potent than whatever emotions are connected to “white” or “other” in the eater’s mind.

So why can’t the pork industry try something like this:

Here’s the slogan to introduce it…

Pork: Supper can be Savory Too

And here’s the idea…

Pork is the most savory meat and it’s not just for breakfast. If you want to add a flavorful flare to your lunches or dinners, add pork as a garnish [everything wrapped in bacon tastes amazing, or maybe bits of ham in the soup] or as the main course [pork belly, short ribs, pork chops] to transform your meal from dull to delectable.

Importantly, this market position is not directly competing with chicken or beef. You’re not saying “Pork: It’s what’s for dinner” because no one’s going to buy that. But since everyone already believes pork is the centerpiece of the most savory meal of the day, it makes sense to transport some of that goodness to meals later in the day, even if it just means sprinkling real bacon bits on your salad or mixing ground pork with the beef for your spaghetti sauce.

It also has no particular ceiling. I guess it’s possible to go too far in your use of bacon, like if you were to…um…yeah, I can’t think of an example either.

Wrapping up

Positioning is hard in the best of circumstances - even if everyone loves your product. It’s even harder if your solution is not universally adored, but in either case, it’s possible to mess things up. The principles for successful positioning, however, are the same:

• You must find an attribute of your product that people already agree with (pork is for breakfast).

• But one that doesn’t lead you down some “other white meat” back alley.

• And then leverage what your customers already believe in making the case for the next logical step (savory should be invited for supper).

That’s all for now. All this talk of pork has got me hungry, and I’ve got to go clean the drool off my shirt.

“Another Overrated Landmark”

So states a “Local Guide” named Robert reviewing the Coliseum in Rome - one of the best-preserved and most iconic remnants of history’s greatest empire - standing largely intact through two thousand years of onslaught by barbarians, tourists, and the elements.

“There are no seats in front of and in the cathedral!”

Says “Manu”, who visited St Peter’s Basilica - the largest church in the world, designed by Michelangelo - and delivered a crushing blow to the so-called “attraction,” its architect, and presumably God himself in the form of a one-star review.

Haters gonna hate.

And while it's tempting to bestow on these dunderheaded critics a star rating that approximates their value, they do serve an important function in the system.

Without sour little princesses willing to complain of peas under their mattresses and snooty little princes eager to criticize the decorations at Windsor Castle, we might believe that the wonders of civilization and of nature were indeed too wonderful to believe - too good to be true.

If all 100,000 reviewers say their experience visiting the Coliseum was perfect (5.0 Stars), we might suspect that the system had been gamed, and what one really finds at the end of the cue is a Las Vegas-esque foam and plaster model: a tourist attraction meant to fill the gift shop.

But 4.7 stars is different. An average of 4.7 stars spread across a sufficient number of reviews indicates both greatness and legitimacy. Greatness, because the overwhelming majority of sane people recognize their privilege when walking in the very footsteps of gladiators and emperors. Legitimacy, because the haters and scamps have been allowed in too, but all but the most hateful reserve their vitriol for the restaurant next door rather than smear it across the foundations of Western Civilization.

4.7 stars is just about as good as it gets within an open, democratic system. If the “dear leader” gets more than 4.7 stars, then you probably live in North Korea, and the voting has been rigged.

Give Your Deal Patina

All of this is why you should allow imperfections to mar the pristine image of yourself and your company that you’re working to communicate to the world.

These imperfections are patina. They demonstrate authenticity. They show that you’re the genuine article, not some cheap knockoff made to fool the tourists.

There are lots of ways you can add this patina (or simply let it show through):

1. You can admit some of the mistakes you’ve made along the way

2. You can communicate that the reason you hired your VP of Sales was because you weren’t very good at founder-led sales

3. You can be careful not to inflate your metrics (or allow them to become inflated in your investor’s mind)

4. You can focus attention on your product's strengths by pointing out a few areas where the competition has an advantage.

If you can’t think of any way to review your company, yourself, or your product in a way that doesn’t result in 5.0 stars, then you really are delusional. But it’s unlikely your investors are.

I’m not, of course, suggesting you go on a rampage - openly disparaging everything you’ve built. But most founders don’t give one-star reviews to their own company. That’s not usually the problem.

The problem is when you work so hard to shield the investor’s eyes from the one, two, and three-star details that the investor suspects you’ve silenced the haters and all those 5.0-star ratings can’t be trusted.

Maybe you’re the startup equivalent of the Grand Canyon or the Coliseum:

• “Absolutely amazing” 

• “Worth the wait” 

• “Far beyond my expectations” 

But without a few negatives to take you down to a 4.6 or 4.8…

• “It was hot, and the lines were long”

• “Just an old building really”

• “Disney World is just as cool, but it’s closer”

… You probably won’t sound credible.

I’ve had a couple of recent conversations with tech founders that have gone something like this…

Founder: “We’ve got a great story, and the metrics are looking good. But…”

Me: “Yeah? . . . But what?”

Founder: “But if the investor asks about [something the investor will definitely ask about] we’re screwed because then she might find out [Romanov-sized family of skeletons in the closet].”

Many, many times, when this conversation comes up, it’s not nearly as bad as I thought it would be. I get a temporary tightening in the diaphragm as the entrepreneur’s body language makes it seem like he’s been murdering puppies, only to find that it’s really something minor:

Oh, this is your first real job, and you’re worried about your lack of experience? Big deal. You’re smart and hardworking, and you’ve got $1.2M in ARR. No one will care whether you learned “management” as a summer camp cabin leader.

Oh, you haven’t done any marketing, and you don’t have a “following,” “audience,” or “fans.” But you do have a few customers, and they are paying and staying with your product. Then that’s ok; you got the better end of that stick.

Oh, you can’t find the right talent because you’re building a consumer app in Lincoln, Nebraska, way outside the tech bubbles. Could be worse. You could be building the app inside Silicon Valley and competing for talent with Google and Facebook.

But sometimes, what comes to light is a serious flub. Sometimes the entrepreneur has really blown it, and sometimes, it’s his fault. Sometimes the screw-up has real, substantive implications for the business’s future.

Then what are you supposed to do? How do you know whether, when, and how to deliver bad news to the people you’re asking for money?

Whether

This is the easiest question to answer and the hardest to implement. If you want to know whether to tell an investor about the events of your startup’s sordid past, then all you have to do is ask yourself whether - if you were in her position - you would need to know those facts to make a good decision.

That’s it. Just the Golden Rule applied to startup funding. Some details really don’t matter, and you can safely skip them. But this is not a situation where “if in doubt, leave it out” is good advice. You’re brain’s internal bias is going to lean toward covering up unsavory but important facts, so try to make an effort to step inside the investor’s shoes, adopt her perspective, and decide what to share based on her self-interest.

The most important reasons to follow this rule are ethical, but there are important practical reasons as well, which I’ll cover in a bit.

When

You should share the bad news early in your pitch, but it shouldn’t be the first thing out of your mouth.

To understand why, imagine you’re back in the dating scene (for some of us, this requires a lot of imagination, but work with me here).

Feel free to mentally modify the below storyline however you please:

Imagine you’re having your first coffee with a really nice (and nice-looking) girl you exchanged numbers with at a mixer the other day. She’s funny, you share interests, she doesn’t appear to have a drug problem - like your last girlfriend - and your personalities really click.

Oh…and she has three kids. Or she just got out of prison. Or her dad is in the mafia.

Woah! 

Ok, there’s no way that info can just drop. It’s going to change the dynamics. But how exactly?

It depends.

If that was the first thing you knew about her, you might not be on the date. She might have been disqualified in single-round elimination, but then you would have missed out on meeting such a wonderful person.

On the other hand, if you get through this date and the next six dates (another coffee, three nice dinners, a long stroll through the park, and a funny afternoon learning to rollerskate) without learning about her past life and its current implications, then you’re almost certain to feel deceived and betrayed. 

In fact, the more you like her, the more betrayed you’re likely to feel.

What gives?

What’s going on is that there is an unspoken expectation in dating and venture capital that anything that might affect the other party’s willingness to deepen a relationship should be disclosed before the target depth is reached. Voluntarily disclosed. Not found out through tricky questions, verbal slip-ups, or mutual friends.

Not mentioning her brief stay in the penitentiary might be fine for the first coffee, but by the end of the second, a lack of disclosure starts to seem impolite. If you get all the way to the altar before she discloses her relationship to the ringbearer and flower girls, things won’t go well.

The reason you don’t have to blurt out the bad news in your first sentence is that it’s not important just yet. Your first job is to pique the investor’s interest in your deal - to tell her something amazing about your company that makes her dream about the possibility of a long and profitable partnership. If that opening step doesn’t work, then it doesn’t really matter what good or bad news you deliver afterwards. She wasn’t that into you anyhow.

If, however, you do manage to secure the investor’s interest in the opening of your pitch, then I hate to be the one to break it to you, but now’s the time to spill the beans. If you wait much longer, it will sound more and more like a cover-up. In the worst-case scenario, the investor will ask an obvious question which forces you to disclose, and the investor will wonder from that point forward whether you would have told her without her prying it out of you. You might lose her trust forever.

How

It's important how you spill the beans, though. Here’s the methodology for delivering genuinely bad news—news that could scuttle your deal.

Tell the Truth

Depending on how bad the bad news is, it might blow up your deal. It might be so genuinely awful that you can’t raise any more money. Even if you suspect this might be the case, you should still tell the truth. This is just the right thing to do. It’s right by the investor - if you were in her shoes, you’d want to know all the ugly details before you stroked a check. 

But it’s also right by you…in the long run. You might be able to get away with this little “omission,” but from the investor’s standpoint, it amounts to a lie. And chances are, it will come back and bite you, either later in the company’s life or later in your career. Because, you see, the willingness to sacrifice someone else’s interests (even an investor’s) to advance your own operates globally. If you do it once, you’re more likely to do it again…and again and again. One or more of these little dishonesties is almost sure to surface later on - probably at a highly inopportune moment.

Trust also operates globally. If an investor walks out of your deal because of details you willingly disclosed, you’ve given her reason to trust you, making her more likely to do business with you in your next deal. She might still take your calls, she might still make connections, and she won’t poison your deal with other investors. On the other hand, if she storms out of the deal feeling deceived and betrayed, you’ll probably never do business with her again. And she might plant the seeds of your destruction with her entire network of investor friends.

Even at a brutally pragmatic level, assuming no backbone or moral compass, it seldom makes long-term sense to lie about or cover up important details. Sure, a single pitch or even a single funding round might go better if you’re sneaky and deceptive, but once you’ve developed a reputation for sneakiness and deception, every other funding round at your current company and your next one will be harder.

And chances are, the news you deliver isn’t as bad as you think it is. The investor might not really care. In this case, you’ll gain trust points and dodge a bullet at the same time. So tell the truth even if it hurts, but it will probably hurt a lot less than you think it will.

Take Accountability

Now that you’ve aired your dirty laundry, you need to establish a scapegoat, and you don’t have to look far to find one: You. 

You’re the boss, you made the dumb decision to switch databases, you hired the toxic, inept CTO, you frittered away your Seed round playing startup.

But you don’t have to make a big drama about it. No one wants to see a grown man cry. Everyone already knows it was your fault, so just state the facts, acknowledge personal accountability, and move on.

The biggest danger at this stage of disclosure is determining the middle ground between “It was all my fault.” and a line-item description of what went wrong. Too much detail, and you’ll sound like you’re making excuses. Too little, and you’ll sound like you still don’t know what happened and are just trying to band-aid over the chest wound. You should aim for a 10,000-foot view - low enough to see a few particulars of what went wrong but too high to take much time describing them.

Move Along

I’ve probably taken more time explaining the first two steps than you should take in covering them. In a typical first pitch to an investor, the first minute or two should still be spent highlighting what’s amazing, intriguing, and interesting about your deal, and if you need to drag a skeleton or two out of the closet immediately afterwards, the process shouldn’t take more than a couple more minutes.

The point of delivering the bad news early is to clear the air for the good news. The good news is that even though you’ve had some stumbles, the current state of affairs is full of promise. You’ve dealt with the shadows from your past, and now you can step into the future unencumbered.

This is probably the biggest disconnect between you and the investor. For you, all the $#!+ you went through is still fresh in your memory. You might still be digging it out of the soles of your shoes. But for the investor, what’s past is dried up like a crusty old cow patty, and as long as she doesn’t have to step in it, she’s not going to dwell on it. 

Did Seed investors (your mom and uncle) have to take a down round? Not her problem as long as the current cap table is acceptable. 

Did you lose six months of sleep and invest your life savings in underperforming Google ads? Good to know you’re not going to quit. Oh, and how’s your current pipeline?

Did you have to fire your best friend or hire over his head to finally build a product that actually worked? Well, does the product work now?

If the current state of the union is strong, then most investors don’t give a flying fart about what’s gone on before - all the angst, wasted opportunities, busted relationships, and permanently-seared retinas staring at code that just wouldn’t run. It seems insensitive. Even a little heartless. But it’s actually exactly what you want.

You want investors facing forward, excited about the present and the future - which you will use the rest of the time pitching them. You’ve delivered the bad news, taken the blame, cleaned the slate and set up for round two - all in two minutes.

No one is perfect. No company is perfect. We all have a little baggage. Some of us have a lot. But you’ll probably be surprised how little of that baggage the typical investor cares about. It just doesn’t affect her that much. As long as you’ve been honest that it’s there, you don’t have to carry it through your whole pitch.

We were looking for a Christmas tree in the woodlot above our house when my kids ran back up to the trail with eyes as big as saucers. There was a bear only fifty feet away underneath that stump!

A few minutes earlier, my nine-year-old daughter Eden had crawled down to see if she could fit inside a little cave. Such an inviting little cave. Just big enough for a little girl or a little…

But little sisters exaggerate. Plus, she wouldn’t know a bear from a beaver. So Eden’s bold and experienced older brother swaggered over to the stump with studied nonchalance, ignoring his sister’s protests, and got close enough to confirm that he was both brave and could move very quickly when motivated.

But little kids exaggerate, and it’s dark in caves. Plus, if I could hold it together, this was an opportunity to score a few dad points. So I crawled down through the brush to the base of the stump to assure everyone that it wasn’t actually a bear. I took out my little flashlight, crouched down, peered in, and my light glinted on two beady eyes spaced way too far apart, staring back at me from a few feet away.

And sure enough, it was a bear. Not a very big bear, not a terribly alert or aggressive bear, but a bear is a bear, and this bear was four feet away, thinking to himself that he must have hibernated in the wrong neighborhood.

Grin and Bear it

You’ve heard people exaggerate. Maybe not by much, but you know it when you hear it. You’ve heard stories about bears in the backyard that turned out to be badgers, labrador retrievers, black stumps, coats hung on rake handles, or that huge fluffy cat your neighbor overfeeds. If you’ve heard as many startup pitches as I have, then you’ve heard hundreds of these stories.

I want you to notice two things about your response to these little overstatements:

1. You didn’t always call bullshit on the person pitching. Often, you just nodded your head and let him think you believed every detail.

2. You began to calibrate every other story he pitched based on how real and how big the bear turned out to be.

This means the entrepreneur might think you’re swallowing everything he’s throwing in the water when in fact, you lost his trust and attention twenty minutes ago.

Or maybe you’re the one pitching the badger as a bear. Maybe you’re prone to just a little-bitty, teeny-tiiinnny, overstatement every now and then in order to get your audiences’ attention.

Sometimes it works. But it’s usually a bad idea. Here’s why.

Going Fishing

Most of us have been guilty of fishing for a compliment at one point or another: When you’re feeling down, and you ratchet up the self-criticism so that your friend, co-worker or spouse will counter your criticism with a compliment.

Maybe you don’t fish for compliments, but I bet you know other people who do.

The most innocent example might be when your three-year-old collapses into a heap of crayons, proclaiming, “My drawing is terrible!” 

To which you dutifully reply, “No it isn’t! That’s such a good…ah…that’s a horse, isn’t it?”

It works in reverse too. If your kid can’t stop telling you he’s the next Rembrandt based on his vaguely animalistic smudges, you’re likely to take him down a notch: “Well, you’re getting to be a good drawer, but there’s still lots to learn…like how to put the horsey’s eye not quite so close to his ear and which way the joints bend.”

What you and Junior are tuning into is the natural human reaction to understatement and overstatement. If someone understates or overstates a fact, then you feel a compulsion to correct him up until the point where you think he’s just trying to get sympathy (over-understatment) or just blowing hot air (over-overstatement, otherwise known as “blatantly lying”). In-between, if the misstatement is small, then your brain’s internal regulator corrects the error whether or not you voice the correction.

For instance, examine your mind’s impulses to correct these made-up statements from famous people:

Sam Bankman-Fried: “I know I made a LOT of mistakes at FTX.”

Your brain’s Internal Regulator: “Ya think?! Maybe your law professor parents should explain the difference between ‘mistakes’ and ‘felonies’.”

Jonathan Ive: “I’ve been able to make a difference in the design world.”

Internal Regulator: “Heck yeah, you have! You rocked the pool, man!”

Martin Scorsese: “Some of the films I’ve directed are not appropriate for children.”

Internal Regulator: “Like all of them.”

Donald Trump: “I like to speak my mind. I really do. I say what I think.”

Internal Regulator: “[violent agreement followed by approval or condemnation]”

Not only is the internal regulator always working to correct over and understatements, but it’s also forming a predictive model which it attaches to the source of these statements which enable it to anticipate whether the person speaking will likely need correction in the future and in what direction.

Which brings me to another bear story.

My youngest son Caleb has always had a vivid imagination, and sometimes sees huge, hairy creatures (bear, moose, elk, sasquatch) lumbering through the woods, up on the hillsides, or across the pasture, even when the rest of us only saw a haybale, a big black stump, or a shadow.

Then there was the incident several years ago when I was crouched with Caleb under a spruce tree in the Canadian Rockies hunting deer. I wasn’t concerned at first when he whispered urgently: “Dad! There’s a big bear, and it’s headed toward us!!”

“Oh, really, that’s nice, son…”

Probably another stump.

And then I looked up and saw the big grizzly bear headed straight toward us. 

My predictive model for Caleb underwent an instantaneous and violent recalibration that day.

Undersell it…a Little

If you’re entrepreneur pitching your next deal, you actually have more control over the investor’s internal regulator than you think. All you have to do is understate the the bear story by a little bit. A story that starts as a labrador retriever and ends as a bear is much more satisfying than one that goes in the other direction, and it builds your credibility. If you tell a story that delivers a little more than you promised, then you build an expectation for interesting and satisfying stories.

So how would this work if you weren’t pitching bears?

Let’s pretend you’re pitching how many customers you have.

The usual approach would be to oversell the number by a little or a lot:

“We have hundreds of thousands of paying customers.”

But as you go along (whether in the pitch or during due diligence), you have to disclose that actually, you have 89,000 customers (close to one hundred thousand), and half of those are on free trials which haven’t expired yet (so they might pay or they might not).

The bear starts to look like a terrier.

On the other hand, if you pitch…

“We have tens of thousands of paying customers.”

Then as all the same details emerge, the story starts to sound more and more credible and compelling: “Wow! so you’re gonna have nearly a 100k paying customers if all those trials convert.”

You promised a little black bear underneath a stump and delivered a big grizzly headed right toward you. The investor’s end state is very near where it might have been had you pitched “100s of thousands” except now the investor believes the number and trusts your next stories.

When you’re pitching investors, the most important thing you have to do is create excitement and interest. Without that, you’re dead in the water. But assuming you’ve got their interest, the second most important thing is trust. Without trust, excitement shrinks, fades, and eventually dies. And there are few better ways of building trust than delivering a bigger bear than you promised.

Steve Jobs was no Luddite.

That much is pretty clear. But does that mean he was a techno-optimist (someone who, as Marc Andreessen puts it, thinks technology is the “good news”)? 

Kinda, sorta, probably, yeah. But I’m not so sure. Some things fit, but some don’t.

First, the obvious: Jobs was the greatest technology evangelist ever (just stating the facts). It was impossible to experience one of Jobs' keynotes and not to come away a little more optimistic about the present state of technology and what was possible in the future.

I was busy building technology in my first company when Jobs was on his second run at Apple, but when he took the stage, my schedule magically opened up, and I watched the keynote. I (along with the entire tech industry) was in awe. How did he make people so excited about a music player or an OS upgrade? It made you proud to be working in the same industry and on the same kinds of stuff. Every tech CEO at the time wanted to be Steve - and many tried, with results between awkward and comical.

But this electrifying energy and forward momentum that Jobs brought to Apple and to his entire era in tech was tempered by his personal tech-minimalism and the focused perfectionism which he engrained so deeply into Apple’s culture that its influence is only now beginning to wane.

The black mock turtleneck was merely the most distinctive mark of Jobs' austere approach to technology and to life. In his worldview, even the technologies of tables and chairs must not be adopted haphazardly. Jobs famously lived in a nearly unfurnished house for years before marrying Laurene Powell, and even then, according to Laurene:

“We spoke about furniture in theory for eight years…We spent a lot of time asking ourselves, ‘What is the purpose of a sofa?'”

Most people do not take eight years to determine the purpose of a sofa. 

Most people have settled that question years ago in a fraction of the time, enabling them to settle their derrieres comfortably into the seat cushion with no further consternation or consideration.

But most people are not Steve Jobs.

Most people buy the washing machine that’s in stock, has good reviews, and fits their budget. But Jobs' own account of this process runs a little differently:

“We spent some time in our family talking about what’s the trade-off we want to make. We ended up talking a lot about design, but also about the values of our family. Did we care most about getting our wash done in an hour versus an hour and a half? Or did we care most about our clothes feeling really soft and lasting longer? Did we care about using a quarter of the water? We spent about two weeks talking about this every night at the dinner table. We’d get around to that old washer-dryer discussion. And the talk was about design.”

Two weeks.

Every night for two weeks!

But that was Jobs, and it’s not all that surprising to hear of his personal obsessiveness because Jobs was like that with everything, especially Apple’s products. He was a purist - relentlessly, brutally focused on creating a few amazing user experiences.

Here’s just a few bits of Steve Jobs lore to illustrate the point:

• When Jobs realized inertial scrolling could be used to build a phone, he put delivery of the iPad “on the shelf,” reasoning that even a five billion dollar company with thousands of employees couldn’t launch more than one great product simultaneously.

• Jobs drove the same model and color of car for years: a black Porsche 911 (which he would replace every six months). He later exchanged the 911 for a Mercedes SL55S - this time silver. He also owned a BMW Z8, but might have owned dozens more if he could have gotten past the “what is the purpose of a car” question.

• On returning to Apple in 1997, Jobs scuttled plans for most of Apple’s products, choosing instead to focus on just 4 computers.

• And the $100M yacht that Jobs designed to look like a 250-foot floating iPhone? It took too long to perfect, and he never set foot on board - leaving it to his wife.

Steve didn’t just advocate this approach for himself. He believed others should do more in fewer areas too. No one loved technology more than Steve Jobs, but no one hated mediocre technology more than Jobs. No one felt the same visceral loathing for a menu with too many nested options, a keyboard with the wrong travel, or an unsightly and unnecessary hinge or screw. Among those building technology, no one seemed to care as deeply as Jobs about whether products fulfilled their purpose - whether they created meaning, delight, fulfillment, joy, or connection.

Not just revenue. Microsoft made lots of revenue. Microsoft was an Apple competitor, and maybe that’s explanation enough for Jobs' criticisms of the company to the north…

“I am saddened, not by Microsoft's success - I have no problem with their success. They've earned their success, for the most part. I have a problem with the fact that they just make really third-rate products."

…But it’s hard to escape the fact that Jobs had a point. Somehow success and first-rate products don’t always go together, and this unfortunate combination can leave the world a little poorer even if makes a company a lot richer.

Put another way, Jobs was not an “early adopter” - that so cherished segment of technology buyers - nor a “power user” of most technologies. He didn’t seem to have any desire to clutter up his life or office with barely-functional apps and gadgets for every task and hobby. Try to imagine, for instance, the criteria and process Jobs might have used to decide what devices to carry in his pocket or what went into his carry-on for a trip. Try to imagine what apps were on Steve’s iPhone and the standards they had to meet to get there and stay there: There they are, taking up screen real estate, but what do they do? How do they look? How do they function? Are they simple enough, intuitive enough, elegant enough, delightful enough for a man who lived without furniture rather than buy the wrong table?

Jobs pressed these ideas pretty deeply into Apple. My limited personal experience interacting with the company is that when the industry says “jump,” Apple’s feet stay planted. Apple adopts technology, but it is not haphazardly, indiscriminately, or fast. They are a hard company to sell technology to because they don’t see “cool,” “hot,” and “new” as sufficient criteria for them to adopt, even if their competitors have long since taken the leap. Apple wants its technology systems to create experiences. They spend a lot of time thinking about purpose and design. Doubtless, Jobs taught them that.

That’s why, when I try to place the “techno-optimist” label on Jobs, I don’t think it quite fits - even though it mostly fits. Jobs was overwhelmingly optimistic about technology in aggregate - its role in the forward march of history - but pointedly pessimistic about whether a particular technology was fulfilling the specific human purpose he had for it - whether that was washing cloths, a sitting platform, a glass stairway, or a music player. That’s why Jobs spent most of his life devoted to perfecting a handful of technological categories and why he was not an indiscriminate fanboy of other technologies. Jobs was one of the greatest technologists of all time, but he was also one of technology’s harshest critics.

I think the resolution of this irony is that Jobs understood a few things about technology that most technologists do not:

Human Scale

Up until Jobs' death, the iPhone’s dimensions were restricted by that of the human hand. Jobs wanted to be able to reach his thumb up and touch any part of the screen. Jobs was also an advocate of skeuomorphic design - the practice of making the digital landscape look, and to an extent feel, like objects in the physical world. For the longest time, Apple icons looked like their counterparts in gritty material existence: The Camera looked like a lens, Books were on a wooden shelf, Notes were on lined yellow paper, and even the icons themselves looked like they had physical edges and depth.

Perhaps none of this was necessary. Perhaps the gargantuan screens we carry around today are optimal, and perhaps Jonathan Ive was right to flatten Apple’s design aesthetic. But I tend to think Jobs had a point, even if each implementation of that point could be legitimately debated. For technology to serve us, it has to be scaled to our limitations, shaped around our humanness, and designed to counterbalance our foibles. We can create fighter jets capable of killing their pilots just as we can create apps capable of killing our productivity.

Human Time

In Jobs’ commencement speech in 2005 to Stanford University, he spoke of death as “life’s change agent,” the limiting mechanism by which our energy, passion, and creativity are funnelled into productive use. Without death - without time limits - we might shuffle around in our bathrobes forever, never quite getting around to building anything insanely great. Similarly, all of Jobs’ work at Apple and many of the eccentricities of his private life stemmed from his vivid consciousness of how the limitations of time necessitated focus. Jobs didn’t have time to pick out his shirt in the morning or shop for a different kind of car once he had found a good one, but he had time to create the personal computer and time to design the iPhone. 

Then there is the story of Jobs’ own cancer treatment and death at only 56. He opted for a combination of state-of-the-art and alternative treatments (what any one of us might do if we were in his shoes fighting a little-known disease). He didn’t resign himself to death but neither did he appear to pull out all the technological stops and ruin his remaining years of life in a desperate attempt to prolong them.

Human Competence

I indicated earlier that Jobs was not a technology “power user” of most technologies. That statement is incomplete. Jobs was certainly a power user of Apple products and I would suspect Jobs had a high degree of competence with the tech he did choose to use. Most people who use technology every day get good at it. If you work in the technology industry, and especially if you build technology, you can master a lot of different types of technology. After a few years of working 60-hour weeks, even complex technologies can start to seem simple - so simple that you think everyone can and should use them. But even though he spent his entire career in tech, Steve never seemed to lose touch with the fact that for most people, each individual technology is a very small part of their lives, and for it to be a pleasant and fruitful part, it must be kept simple and intuitive.

Jobs saw that adopting too many technology products too quickly is a recipe for incompetence at a personal and organizational level. Better to know and use and build a relative handful of great technologies with complete mastery than hundreds of third-rate ones with ineptitude. And if this was true for Jobs and for Apple, it’s surely true for schoolteachers, carpenters, accountants, and designers. It’s also likely true for you and your company. If you’re a perpetual early adopter of a host of new tech, then you never have time to push a few of those technologies into skillful, everyday use.

Human Purpose

If a computer is, as Jobs said it was, “a bicycle for your mind,” then the most important question is one of destination - of purpose. Steve, more than any technologist of his time (or, for that matter, of our time), was willing to constrain his own and Apple’s technological progress in order to adapt technology to human purposes. If it took eight years of discussing furniture in theory, and if, in the meantime, you had to sit on the floor, then so be it. If it took an extra three years to ensure that the iPad experience was not just a big iPhone, then that was time well spent. If you die before the yacht is completed, then that’s a small price to pay for the ability to focus which only the prospect of death can give you. When it comes to pursuing technological progress, don’t compromise - don’t take shortcuts. If you’re not careful in constraining technology design and clear on its purpose, then it’s likely to lead you somewhere you don’t want to go: to the Zune, not the iPod.

Focusing to Go Faster

The irony, of course, is that even within the severe constraints which Jobs placed on himself and on Apple, he managed to, arguably, advance technology further than any technologist in history. Many of the biggest categories of technological growth are extensions of markets Jobs began or at least shaped.

How was Jobs able to create so much technological progress within such draconian self-imposed limitations? The answer, I think, lies in the fact that Jobs spent orders of magnitude more time than most technologists thinking about the true nature of the human destinations he was seeking to reach: beauty, delight, connection, and creativity. And once he saw the possibility of achieving these ends, he was unwilling to settle. As a result, he took longer to build fewer technologies, but the ones he built were more compatible with the human condition. They felt natural, unintrusive, playful, and elegant. These kinds of technologies have staying power. These kinds of technologies transform industries. Much more so than the constant stream of awkward and often convoluted apps and gadgets we are told we must adopt right now to stay on the cutting edge.

He wasn’t perfect or perfectly consistent. Jobs stumbled into pragmatism from time to time (Antennagate comes to mind), and he was surely motivated by commercial success. But he didn’t want that success to be built on selling junk, and for the most part, he was successful at building commercially viable works of art. Art that fit nicely in the hand and in people’s lives.

The unofficial motto of many technologists and technology consumers seems to echo Zuckerberg’s famous admonition to “move fast and break stuff,” but that was not Jobs' motto. In a way, his whole career was spent fixing user experiences other technologists had broken - whether personal computers, music players, smartphones, or tablets. Sometimes, moving fast and breaking things slows you down in the long run (as perhaps even Meta would now admit), and sometimes, moving slow enough to create technological excellence informed by careful consideration of human purpose is the only way to make real, enduring progress - the kind that doesn’t engender societal backlash and produce as much collateral damage. It took longer for Apple to get to market, but once they got there, the market leaped forward a decade in a day. Apple didn’t enter as many markets, but the ones they entered anchored the entire tech industry.

You may be as optimistic as Jobs was about how technology can move the universe forward. But if you - just you and your company - want to play a part in that progress and put a dent in something as big as the universe, all of your energy has to be directed on a very small surface area. You must be willing to abandon universal progress to make a dent locally. And since life is short and time is fleeting, you might want to first spend some time thinking about dents in theory to make sure you make the right one.

When you’re snowmobiling in deep powder, and want to turn right, you have to turn the skids left while you brap the throttle and lean the whole 500-pound machine on its right side. For a beginner like me, It’s almost impossible to convince your body to turn the handlebars toward the big scary slope in order to steer away from it.

When you learn to box, you have to keep your elbows down by your sides, you tuck your chin, and your left shoulder hunches up to your ear. It feels nearly as awkward as getting punched in the face.

If you’re piloting a jet boat up a river at 30 miles per hour, the jet doesn’t act like a rudder (like on a prop boat), so your ability to steer is proportional to the amount of thrust. You have to steer with the throttle. Plus, if you go slow, you’ll sit lower in the water and hit rocks deep beneath the surface. So if you do what any sane person would do and throttle down to avoid an obstacle, you’re more likely to hit it and hit it hard.

Most of life is like that.

Maybe wildebeests can just do what feels right, but for humans, we have to constantly contort our minds and bodies into awkward, unnatural positions in order to learn to bike, swim, play the violin, type on keyboards, code websites, and impress our friends at the skate park.

The upshot is that we don’t have to drink nose-down at the water hole, and far fewer of us get eaten by crocodiles.

Which brings me to pitching.

Every entrepreneur already knows how to pitch. Just like they know marketing. You just trust your intuition and let’er rip. Just turn the handlebars in the direction you want to go. Just belly up to the water's edge and take a sip.

What could go wrong?

But go take a look at those pictures of your first birthday. Not even cake eating is a skill you were born with, and if you really want to excel on the pitch, then you have to train your mind and your mouth to think and say things that don’t come naturally.

Here’s ten pitching skills that monkey with our intuition. Just settle in because things are about to get awkward:

10. Prepare to Sound Natural

The best way to sound natural is to make your pitch impromptu. Off the cuff. Unrehearsed. Back of the napkin.

Nope. Save the napkins.

If you don’t rehearse your pitch at all, you’ll probably sound like you were scripted. But scripted by a clueless consultant giving you instructions over a bad cell connection. If you script your pitch word for word, you’ll also sound scripted, but this time by the generic, monotonous ChatGPT version of yourself.

If you really want to sound natural, then you have to put in reps of your pitch (to the bathroom mirror, to the dog, to your kids, to strangers on the subway) until you’re not fumbling through memory to find the details - until you can riff and improv with ease, until it’s harder to mess up than nail it. Guy Kawasaki recommends 25 reps in The Art of the Start. The best actors act their best when they aren’t struggling to remember their lines.

9. New To You

Pitching can be boring…for you. Because you’ve pitched the same thing in the same way 60 times this week. You start to feel like you need to spice things up.

Resist!

You’ll probably just wander off into some pointless backwater and leave the key things unsaid.

My pitch is old to me but it’s new to you. The trick is remembering the magic moment three years ago when the great idea you’re pitching now exploded onto your prefrontal cortex, for a moment displacing the orbit of all other thoughts in your galaxy. Hold on to that feeling! You can make others feel the same way, but not if you branch off-topic just because the fuzzy feeling has been worn smooth for you.

8. Saying What the Slides Are Not

Your audience can read. They can read silently faster than you can read out loud. So for the love of lava lamps and dogs in the office, don’t read your slides. Just because the text is on the slide doesn’t mean you have to say it out loud. 

That’s why the text is there! So you don’t have to say it! 

Just don’t.

Instead, say something that provides context for the text or the images or provides a corollary to the narrative.

7. Not Saying Everything

Hmmm. What do I want an investor to understand?

Oh, everything. That’s right! So I better highlight everything.

But if you highlight everything, then nothing is highlighted. Ten bands playing at once is not music; it’s noise.

So if everything in your pitch is bright red and ALL CAPS and bold and you try to hammer home 10 key points on each slide, then your pitch devolves into static - just a faintly-irritating, crackling whine in the back of your audience’s brain.

You’re not going to be able to communicate everything. Get over it. Even if you could communicate everything, it’s not going to happen all at once. Leastways, it’s not going to happen on this slide.

Instead, break your idea apart and focus on one bite-sized morsel at a time. Connect the breadcrumbs together in a tantalizing sequence, and eventually, your audience may consume the whole loaf.

6. Start at Interesting

Like Putin in the Tucker interview, many entrepreneurs feel the need to start with what came first. Back when half of what is now Russia was ruled by Ghengis Khan.

It’ll work just as well for you as it did Putin.

Go watch the movie Memento, a riveting whodunit that unfolds in reverse chronological order. Why do you put up with such a convoluted story sequence? Because it’s interesting. Because every scene is interesting. Especially the starting scene.

So that’s where you should start too. Start with the most riveting detail about your story, your product, and your market and bridge from there into the rest of the pitch. When you first start pitching, the most important factor is the audience’s motivation to keep listening and interesting beats first every time.

5. Undersell…A Little

It’s hard to get people’s attention so our tendency is to dress up our experience, our sales, and our tech at the outset so there’s no possible way that our audience won’t be disappointed by the end of the pitch.

You do have to get people’s attention, but starting at 11 means that even if you’re a 9, investors will feel let down, maybe even deceived.

Instead, start a wee little bit below the expectation you know you can exceed as you disclose more information and gradually step up the scale. The investor’s emotional journey from good to better will feel more satisfying than a journey from great to good.

4. A Hot Data

For some reason, people act like data is naturally sexy. It’s not. Or that their audience is Data - a pale robotic calculator of a human. He’s not.

The data says 3,000 people are killed by distracted driving in the US every year, and I bet the investor you’re pitching was still texting at stop lights on his way to work this morning.

Data is only convincing if it’s in a context where you can emotionally connect with it - If it’s part of a story you’re a part of. Likewise, even the most Data-like investor isn’t going to pull out his wallet just because all the numbers add up. He’s waiting until he feels that special something deep in his squishy human heart that provides the motivation to do math in his cold hard android head.

Maybe it’s the account of why one of your thousand customers chose you, or maybe it’s getting into a fender bender on Sand Hill Road. Either way, data doesn’t have a pulse unless it’s placed inside a story.

3. Highlight your Failures

You’re not fooling anyone. You’ve got competitors, your experience is spotty, your product’s not ready for prime time, and all the marketing you’ve done is that one run of Facebook ads.

So own the suck. Admit your failings. At least some of them.

If you can own up to your shortcomings, then your audience will give you credit for other qualities. You may be young, but you’re smart, your early adopters love you enough to put up with imperfections, If you’ve made $20k on a few ads, then what if you could hire someone who knew what she was doing?

2. Asking for Money

If you feel natural asking for money, then your trust-fund-baby childhood must have caused psychological damage. Most of us feel as comfortable asking for money as guys discussing menstrual health. Sometimes even experienced entrepreneurs blush and break down when it comes time to make the big ask.

But money’s probably why you’re pitching, so it’s part of the deal. It sort of is the deal if there’s a deal to be made.

The trick to making “The Money Talk” less cringy is to equate money with acceleration. Acceleration not movement. If you don’t get the money, that shouldn’t mean you stop or (worse) that you don’t start. Money should make the rocket ship go faster, but the launch should be inevitable. If the idea of more money is connected to all the ways it’s going to help you grow faster, then the money talk is fun not awkward.

1. Shutting Up

To pitch you have to pitch. But the most important and least intuitive part of pitching is learning when to stop pitching. When to shut up.

People usually don’t shut up soon enough because they want to be extra-especially sure that the message got through. So they circle the wagons, beat the dead horse, and whistle into the wind in hopes one of those metaphors isn’t accurate.

But the regurgitation of what you just said isn’t usually as interesting or appetizing as when it was fresh. Plus, you start to sound like you really really really need your audience to believe what you’re telling them please!!! . . . which of course makes your audience feel like you’re desperate or lying or both.

So say what you need to say and no more. And then stop. Really. No really, you should stop now.

Ok, stopping.

Oh, but I…

Nope. Just shut up.

Oh, it’s a rerun of Leader of the Free World.

The episode where each of two old guys spends the next six months and billions of dollars to convince a small coterie of swing voters that while he is not a “clown” or “sleepy,” his opponent definitely is.

Where’s the popcorn?

Even though we’ve seen this movie before, everyone wants to know how it ends. Especially since a fair number of people didn’t think it actually-really ended last time.

Can Donald Trump pull a Grover Cleveland and get elected for a non-consecutive second term or can Biden…well… hang in there, buddy.

Lots of things could switch the flip and I’m basically going to ignore them all to focus on this question: 

How can we pitch either of these knuckleheads as presidential?

Because here’s the deal: you probably don’t matter in this election because you’ve probably already made up your mind. You’re probably already convinced that Trump is a threat to global geopolitical stability (not to mention the stability of those tacos you just ate) or that Biden is an animatronic shell operated remotely by an indecisive committee of establishment liberals (and let’s just say the signal is not always at five bars).

In fact, even if - as a moderate voter - you do matter to the outcome of this election, you might still think Trump is a megalomaniac and Biden is geriatric.

Change We Can’t Believe In

What is a marketer supposed to do with that? What can you say about either one that might swing the vote?

What makes this an interesting question is that everyone already knows the products. It’s untrue that Biden helped Brutus stab Julius Caesar, but the man has been in politics for a long time and Trump, like Truman Burbank, has been on camera since birth. Practically every feature and foible of both men has been examined in excruciating detail for decades. No one will watch the next interview or debate and say to herself: “Huh, I never knew [Donald or Joe] felt that way about [important issue]. He’s got my vote.”

Unlike previous election cycles, you can’t rely on hopey, changey, white knight anonymity to sweep one or the other candidate to victory. Vivek already played that card and the country yawned.

Yes We Can’t

But actually, this glut of information and impression overload is the key to pitching either candidate for president. To effectively position either Trump or Biden, we can’t try to change anyone’s mind. We’ve got to work with what we’ve got - what voters already believe.

This eliminates a LOT of options. 98% of everything we could say doesn’t pass the bullshit detector:

• “Trump stands on the principles set forth by our forefathers in the constitution” - Oh, well, except for that one.

• “Biden isn’t going to cave to the political elites.” - unless they ask nicely and he owed them a favor from 1974.

• “Trump is a steady hand amid the turbulence of history.” - just like a three-year-old on a long flight.

• “Biden is a dynamic leader ready to guide America into a dangerous new world.” - let’s just hope he can avoid bombing Albania by mistake.

• “Trump is the consummate diplomate, restoring trusted relationships with America’s allies.” - [YouTube’s “Trump handshake”]. Ahhhh…No.

• “Biden is feared and respected by America’s foes.” - but mainly just feared to be senile by members of his own party.

• “[either] is guided by a strict moral code preventing him from seeking private gain from public office.” - Yeah, not so much. Although one is less blushy about it.

So what can we say for each candidate if we can’t say pretty much all the things campaigns usually say about presidents? Are there qualities of each man that both sides (the fans and the critics) would agree on?

Here are a couple that I think are important, not least because they constitute the most obvious difference between Joe and Donald:

Trump is a Maverick. He’s not controllable by his foes. He’s not controllable by his friends. He’s only questionably controllable by himself. You might love it when he “says it like he sees it” or cringe when he sounds like a petulant, orange-haired child, but no one believes anyone is scripting Trump. Both camps agree that Trump’s press secretary has one of the hardest tasks on planet Earth - a job akin to that of a drywall crew brought in to patch up Chernobyl. You can say a lot of bad things about Trump, and by this point, everything has been said, but no one says Trump is muzzled or leashed - despite many demands that he should be.

Biden is a Team Player. Biden got the nomination in 2020 because he had served his time and it was his turn. His team pushed him to the front and in exchange, he’s faithfully pulled the levers of power as you would expect an amalgamation of the Democratic party would. A zillion years in congress, eight years as VP and three years as President and Biden has yet to surprise anyone about anything. If a top general says we should bomb someone, Biden pushes the red button. If an economic advisor suggests holding off on new stimulus, then Biden will faithfully turn off the spigot. Biden’s press secretary has a hard job for very different reasons. She’s got to somehow assemble all the words from all the sources from across the whole team and place them physically in Biden’s mouth. You may love him or hate him, but no one’s arguing that Biden doesn’t listen to instructions.

It might be a little amusing and a little depressing that this is all we have to work with, but stop and consider for a minute how important these respective qualities are:

A maverick is independent. Part of the reason the 49ers made it to the Super Bowl is that most opposing teams couldn’t figure them out. They weren’t orthodox. When the other team zigged, they zagged (You can’t blame them they didn’t have Taylor’s boyfriend). For a leader, independence is pretty important, especially with all the current geopolitical craziness. If you’re the dear leader of a militant totalitarian state, you’d much rather play nuclear chess with someone predictable than someone who’s just as unhinged and volatile as you are. Even domestically, if a leader can’t be prodded and handled into submission, he’s likely to be able to produce wins in arenas where the usual calculus would fall flat. America, after all, was built on independence - the freedom to live and govern however the hell we the people please. If one of those peoples were just a bit more independent than average, he might well make a good leader for the whole rowdy bunch.

A team player is coachable. Even back in Washington’s day, the top job was more than any one man could handle. The president has to make decisions about economics, immigration, war, peace, which friends to pardon, whether to mask or not, how to handle congress, how to handle the family business - all while trying to remember three regions in Ukraine and the last name of the French president. Everyone knows the president has handlers and everyone knows those handlers (experts in all the minutia of domestic and world affairs) are absolutely necessary to help the president make good decisions and not make a fool of himself. Sure, the experts are wrong sometimes, but do we really want a reality TV star, an Arkansas lawyer, or a lifelong politician choosing unilaterally whether to start World War III? After all, the American system of government was designed to keep guys like George (no, the other George) from acting like a king and making changes at his own whim. If the president doesn’t take advantage of the wisdom of crowds and the presidential apparatus and doesn’t respect the will of the people (or at least his own party) then he’s not likely to be very effective and he may very well be a threat to democracy.

The most obvious qualities of our two contestants are pretty important. And it’s not just spin. It’d be hard to make the case that the president doesn’t need a degree of independence (a little inner maverick) or that the president can lead the country effectively without listening to experts’ input.

For example, consider these two everyday scenarios which any president might encounter:

Scenario #1: Better Cut the Right Wire

A rogue nation led by a dictatorial madman has sponsored a terrorist organization to lock the President of the United States inside the Oval Office with nothing but a cell phone, a pair of wire cutters, and a nuclear bomb capable of levelling the D.C. metro area.

[Explosives Expert (on the phone)] “Ok, Mr. President, you should see two wires emerging from the big cylindrical bomb-shaped thing and going into the digital red countdown thing. One wire is BLUE and the other is RED. What you’re going to have to do is wait for the timer to reach 0:59 and then cut the RED wire.”

If Biden were President

[President Biden] “So you want me to cut the blue wire? But the timer is at 1:11.”

[Explosives Expert] “Wait for the timer to reach 0:59 and then cut the RED wire.”

[President Biden] “It’s 0.55 now. I’m cutting the RED wire.”

[Cut’s red wire, saving D.C.].

If Trump were President

[President Trump] “Look, I have to tell you, and I'm very, very serious about this, I’m not going to cut the red wire. And let me explain why, because it's very important that everybody understands this. Red, as you know, is a fantastic color, a powerful color. It's the color of our great party, and it represents strength, passion, power. We love red, everybody loves red. Cutting the red wire? That's not going to happen under my watch, believe me. The red wire stays. It's a tremendous wire, really tremendous. How about we cut the BLUE wire? What would you think of that?”

[Explosives Expert] “Mr. President, It’s vitally important that you cut the RED wire but only after the timer reads 0.59 or less”

[President Trump] “Wait? We don't wait. We're going to cut the blue wire, and we're going to do it NOW! The blue wire, we’ve looked at it, we've studied it, and it's the one to go.”

[US capital is moved back to Philadelphia]

Scenario #2: An Offer He Can’t Refuse

Same dictator, same terrorists, same nuclear bomb in the Oval Office, but this time, the President doesn’t have wire cutters so the bomb must be deactivated remotely. The President calls the dictator’s direct line:

If Biden were President

[Dictator] “Hello, this is the dear leader”

[President Biden] “Listen! You’ve got to disarm this bomb in my office right now! This is unconscionable. It’s against the Geneva Convention. We will sanction you with the mother of all sanctions!”

[Dictator] “Bomb? What bomb? This is the first I’ve heard of it. It must have been planted by a terrorist organization we have no affiliation with.”

[US Capital is moved back to Philadelphia]

If Trump were President

[Dictator] “Hello…”

[President Trump] “Listen dictamonious! Solve this problem! Turn this bomb off or you’ll never solve any more problems. You're not going to like our solution. It's going to be swift, it's going to be powerful, it might involve a missile to your yacht, your vacation home in Monaco, you’re favorite race horse, your basketball signed by Dennis Rodman.”

[Dictator] “…Ahhh…Bomb? I don’t know what you’re…” [Interrupted by sound of nearby explosion]

[President Trump] “Oops! I guess that one must have hit your riding stables. Sad! The next one will be…”

[Dictator] “I am turning off bomb now! It’s off! It’s off! [Other explosions heard over phone]

[D.C. is Saved]

You see, depending on the situation, being independent or coachable might allow Philly to keep its reputation as the city of brotherly love.

Make The President Great Again

So what should the two campaigns do with this? How could you pitch these two wildly different versions of president and have each pitch be believable? Bonus points if the pitch simultaneously and implicitly throws the other candidate under the bus.

Here’s a stab at just that:

Leaders Lead: Leaders can’t be followers. They can’t ask permission to vote their convictions, and they can’t make every decision by committee. We live now in a dangerous world surrounded by threats here and abroad that our parents never dreamed of. It’s going to require boldness and independent thinking for America to navigate safely through these troubled waters. Haters are going to hate, but a true leader can’t second-guess every action. He’s got to take the helm and act decisively with ironclad conviction. Trump for President!

Leaders Listen: America was founded on the principle that we are stronger when we are united - when our common bonds enable disparate and diverse people to act as one nation. The Declaration of 1776 says “we the people.” The president’s job is to represent the people of the United States - their interests, their goals, their wisdom - and this means listening to them, both directly and through their other elected representatives. America’s leader can’t act as a rogue agent. He must submit to the rule of law and to the principles embodied in the Constitution. Biden for President!

What’s going on here? Why do the presidential pitches above sound plausible even though we may be resistant to their message? It comes down to four stages:

1. “That’s Bullshit”: By starting from an attribute of each candidate that is hard to argue with, we can bypass the first line of defense. The pushback to most pitches is “that’s bullshit” but Trump is independent and Biden listens. That’s just the facts ma’am.

2. “Yes, But It Doesn’t Matter”: We’ve dodged the bullshit detector, but we’re not out of the woods. The pushback now shifts to “well, but that doesn’t matter.” This is real progress! We are now able to make the case that the attribute in question is actually a pretty big deal - It is an important quality in a world leader. A leader should have a spine and be a team player.

3. “Ok, it Matters, but This Matters More”: The haters will now make the case that even though the attributes of independence or coachability are important, they aren’t as important as the qualities of the opposing candidate or all the qualities the candidate fails miserably at. But that’s ok. We’ve gained a lot of ground.

4. “This Matters More NOW!”: Now comes the cage match. But it’s a different type of cage match than you might expect (and not as entertaining as one involving two old men in an octagon). Now Trump’s side has to argue that at this time independence is more important than coachability what with all the crazy unpredictability in the world and Biden’s side has to argue that actually these conditions won’t be fixed by adding unpredictability to the mix. Rather the present moment requires a steady hand tempered by the input of hundreds of advisors. By associating the candidate with a desirable attribute the contest is now between the attributes not just the personalities.

Change We (Already) Believe In

Will either campaign take my advice and try to associate their candidate with these obvious qualities? I’m not going to sit by the phone. And admittedly, there are other ways to skin the cat.

But I highlight these two angles to illustrate a point about pitching anything - a product, a company, an octogenarian: you don’t have to change anyone’s mind. 

Not really. Not totally. 

You just have to identify a modicum of pre-existing belief or opinion and then build your entire case from that foundation.

No one elicits stronger likes and dislikes than Trump and Biden and yet even the hardest-core MAGA-cap-wearing zealot would admit that Biden listens to advice (“how else would he tie his shoes in the morning”) and even the wokest progressive couldn’t fail to see Trump’s independence from the political establishment (“like all of history’s would-be dictators”). Neither hyper-partisan will be swayed by these realizations, but a lot of moderate voters might be.

In the same way, when you’re pitching your product to customers or your company to investors, the most important question you can answer is what your audience already believes about your market, your competition, your company, your technology, or even you yourself.

If you can find just one or two things they already believe, that’s plenty. If we can find nice (and true!) things to say about either Trump or Biden that people across a wide political spectrum might actually believe, then there’s hope for whatever you’re pitching too.