50 Lessons for Selling to Strangers

Your prospect doesn’t know you. They don’t owe you attention. They’re skeptical, they’re busy, and they have more to lose from picking you than to gain.

That’s the starting position of all B2B marketing. These 50 lessons, one for each video I’ve posted, are about what to do from there.

They run in order, from the sentence that holds everything up to the small tactical moves. Read straight through, or jump to the one that hurts.

Part 1: The Foundation

1. The one sentence behind all B2B marketing

We understand your negative present and we can shortcut you to a positive future.

Every part of that sentence works.

Negative present. If the present isn’t negative, they don’t need you. Nothing to fix, nothing to improve.

Shortcut. This is the verb. Nobody says “we can fix it, just give us ten years.” People in a negative present want out, and they want out fast and easy.

Positive future. Usually the opposite of the negative present. High churn becomes low churn. If you want to get clever, describe a positive future they haven’t thought of yet, one they didn’t know was possible.

Don’t lie in any part of it. Do write it down and check your homepage against it.

2. The buyer knows the problem. They’re shopping for the bridge.

Almost no B2B company has to educate a prospect into knowing they have a problem. By the time they reach you, they’ve done most of the research. They know their negative present. They can picture the positive future, at minimum as the absence of the problem.

What they lack is the bridge between the two. That’s you: your product, your process, your idea.

So you sell a shortcut. Your job is to be not just a better shortcut but, if your messaging is good, the only one that makes sense.

Don’t spend your words describing the destination. They already have that one. Spend them on the mechanism.

3. What happens if they do nothing

The negative future is what happens if the prospect doesn’t use your solution to get to the positive one.

Sometimes it’s just the negative present, extended, and harder to shake.

Sometimes it’s worse. Something gets taken away or added, and now there’s a load they didn’t carry before. A wound that can’t be closed. The negative present they thought was bad turns out to be nothing next to the one they’re in now, which used to be their negative future.

Use it sparingly. But know what it is before you write.

4. Your boss is going to want to talk to these guys

In B2C, you’re trying to create one thought: I need that.

In B2B, the thought is different: my boss is going to want to talk to these guys.

Take your eye off that and you default to informing and educating. Informing is passive, and it’s too risky. Somebody has to persuade another person to change. Education doesn’t do that.

Keep the sentence in front of you. Every page, email, and ad either builds that thought or it doesn’t.

5. Marketing exists to make people feel understood

The point of good writing is to be understood. The point of persuasive writing is to make the other person feel understood.

Being understood is table stakes. The goal is that the reader feels you understand them.

If you think marketing’s job is to educate and inform, you’ll write one way. If you think its job is to create change, you’ll write another.

Part 2: The Buyer’s Head

6. The question they never say out loud

How do I know it’s safe to vouch for you to my boss?

Nobody says it. Everybody asks it. If it looks like you could embarrass them, get them laughed at, knock them off a promotion track, or get them fired, you’re out.

You don’t win the sale by answering the safety question. It’s table stakes. But you have to answer it first, before they’ll go any further with you.

The usual answers are numbers and names. A strip of customer logos they’d recognize. Countries served. Projects completed. Ninety-nine percent would buy again. Eight projects a day for fifty years.

The message underneath: you wouldn’t be the first to go down this road. It’s well paved. No surprises. Keep reading.

7. Hope, confidence, and safety, delivered fast

At the start of a buyer journey, three things are happening at once. You need to convey each quickly and then move on.

Safety: it’s safe to vouch for you.

Confidence: they arrive with none, so you supply all of it.

Hope: we understand your negative present, and we’ve shortcut others to a positive future. We can do it for you.

Don’t dwell on any of them. Treat them as givens. The stranger just doesn’t know you well enough yet to know they should feel them.

8. Fill the confidence bucket

A prospect who doesn’t know you arrives with an empty confidence bucket. If they don’t leave with a full one, they won’t recommend you. They’ll recommend the three companies whose buckets are already full.

So the request is simple. Don’t hedge. Don’t be vague. Don’t prevaricate. Skip enabling, helping, and transformational, the soft words I can’t pin down.

You won’t make me confident by pulling away from me. Move toward me, and let me know you understand my problem.

You provide all the confidence at the top of the funnel. They’ll develop their own later.

9. “Don’t hurt me” language

Most B2B companies write in language their lawyers like. Nobody can call them on it. We help clients transform business processes for a bright future.

What does that mean? Nothing. It puts nothing in my confidence bucket.

The opposite of don’t-hurt-me isn’t aggression. Companies assume it is. Buy this or you’ll die tomorrow. Your company won’t exist in two years without our AI. Not true, and nobody believes it.

Between the two there’s a tiny spot on the spectrum called assertive. Assertive means: we believe X, so we state X as fact. Simple declarative sentences. Commit to things.

The prospect infers the rest. They don’t do everything, but they do A and B, and I need A. That’s a reason to keep reading.

10. Assertive is professional. Generic is not.

When you go for assertive, someone inside your company will say it isn’t professional. What they mean is it isn’t generic.

Here’s the reply. In marketing there’s no safety in numbers. You don’t eat better because you copied your competitors. The whole point is to eat better, so you need to persuade. Which means persuasive is professional.

Professional, properly, means courteous. Professional courtesy. Assertive language is courteous because it uses the least of the prospect’s attention and gives them the most. Two or three things in every short sentence.

Inside your company, professional usually means generic. The middle of the road is the most dangerous place to stand, no matter how much traffic there is.

11. Skepticism kills the hero’s journey

I’ve yet to see real evidence that the hero’s journey works in enterprise B2B.

Any story needs a willing suspension of disbelief. You sit down at a superhero movie and you accept the dinosaur on the space station. You don’t demand it be verifiably true.

Now walk into a Monday meeting and say your quality is excellent and your prices are among the lowest. Good quality and low prices? Doesn’t sound believable. Skepticism is baked into the process.

Small companies, maybe. Anyone with heft, no. Don’t bet the farm on it.

12. They have all the downside and none of the upside

It doesn’t matter how much money you’d save them or make them. If the person reading thinks there’s a chance they get fired, lose a promotion, or lose reputation because you can’t deliver, you lose.

Think about their position. They bring you in. If you screw up, it comes back on them. If you do well, it barely helps them. By then the deal has passed through managers, supervisors, and a regional VP over weeks, months, even years. Nobody will remember who recommended you.

Downside risk everywhere. So the safer choices make the shortlist: the one to three biggest companies, or the one company talking about an angle no one else is.

Make sure they understand you’re the safe choice.

13. The four resistances

Four resistances show up. Different parts of your company own each.

Distrust of claims. Marketing’s job.

Reactance. The feeling that someone is closing down your options. Nice card. Do you have it in blue? If I had it in blue, would you buy it right now? Terrible response. Sales’s job to overcome.

Scrutiny. Subject matter experts handle this. Does it meet the standard? Where are you on the roadmap when the industry shifts?

Inertia. Everybody’s job, because it’s your number one competitor. Not the biggest company in your category. Inertia.

Every employee knows that putting off a decision until tomorrow has almost no risk. Often it’s the safest move. Then one more day. Then six months go by and the deal hasn’t moved.

14. You’re talking to two people

Every voicemail, brochure, and use case has a second audience: the person you’re talking to, and the person above them.

Your message has to be simple and compelling enough that the first person can carry it, ideally without notes, to their manager, supervisor, or VP. And it has to pass the safety test underneath: is it safe for me to pass this along?

Talk only to the person above and the reader finds nothing for them. Talk only to the reader and you get facts and figures that don’t say anything their manager cares about.

The obvious audience, and the next one up.

15. Above the line, below the line

Every company you reach has both. I took the terms from a book called Outbounding. I didn’t like the examples in it, but the idea is right.

Below the line people care about the technical side. Feeds and speeds. Does it have this feature. How long will IT take to set it up. How much downtime.

Above the line people look at what you sell in relation to the company’s strategy. Does this make sense now? Do we need it at all? What piece of my larger problem does it resolve?

In my corporate career we called it the two-sale track: a technical sale and a business sale. Demos and bake-offs for the first. For the second, where you fit in their plan to build a data warehouse or go hard on AI.

The worst outcome is a meeting with the business person who says why are we talking? This isn’t in my plan. All that time convincing the technical people, wasted.

Easy way to remember: below-the-line people can say no, but rarely yes. Above-the-line people can say yes even when the technical people said no. Life isn’t fair.

16. Three wallets

In B2C, every consumer has two wallets in their head: I want it and I need it. Want products try to become needs. Need products often try to become wants.

B2B adds a third wallet: suit. Does it suit the company? Where we are now, where we’re going, where we came from, the positive future we want, the negative present we’re in?

That doesn’t raise the options by fifty percent. It triples them. Want to need, need to want, want to suit, suit to want, need to suit, suit to need.

It isn’t more opportunity. It’s more complexity. We’re also different people in different contexts. The person reading your ad at their desk isn’t the person scrolling their phone at lunch. Someone buying for their family and someone buying for their company are different buyers.

Part 3: Your First Contact

17. What first contact messaging is

First contact messaging is any point where a prospect typically meets you for the first time. Ads. Your homepage. Postcards. Outbound email. All cold outreach, and a lot of inbound.

Almost everyone starts by informing and educating the prospect about the company. Usually wrong.

The first company a prospect visits creates a better informed prospect. Every company after that creates a differently informed prospect. By the seventh company saying the same thing, the value is close to zero. And prospects give you no credit for it.

Do what almost nobody does. Focus on the first half of the master sentence: your negative present. Almost nobody dwells on it, and there’s a lot of value in it. Safety, hope, and a spot on the shortlist, if you show you live and breathe the one problem they’re researching.

You don’t have to solve everything. They’d doubt you if you implied you did.

18. Tell them their own story, with you in it

An asymmetric advantage means an outsized impact from the smallest input. Time, money, talent, whatever.

Most companies do the opposite. They tell the company’s story over and over and over. If you’re not a big player, you’ll never have the time or money to educate a market into existence.

So walk in their shoes. Understand their negative present and the positive future they’re trying to reach. Then put yourself in their story as the bridge.

It’s cheaper and faster than getting anyone to sit still for yours.

19. Deliver 90% of their thinking before you show up

At the top of the funnel, your prospect will never meet you halfway on time, attention, or emotional investment. They’ll stay as far back as they can, and they’ll be skeptical.

So you do 100% of your own thinking and feeling about what you sell. And you do 90% of theirs before you arrive, so they only have to do the last 10%.

Know what they’ll feel and think when they get there. Preempt objections: know what they’ll say against you and get ahead of it. Then go further and prevent certain thoughts. If your page looks cheap, you’ve put a feeling in their head. Do the guard-railing so they stay on the path.

Done right, it won’t occur to them to ask about X or doubt Y until later. It will eventually. Just not at the start.

20. Start at the aspirational level

All your messaging lives on one of three levels.

Informational: this is who we are and what we sell. Ninety-nine percent of B2B lives here. It’s fine for most of what you publish. It’s wrong for the first thing anyone sees.

Aspirational: you could be different. This is the sweet spot. Start with hope. I understand your negative present, and here’s what’s possible.

Transformational: you could be new. Almost never seen in B2B. The internet was one, for about a decade. Crypto, sort of. AI, and people were tired of it within three years. These messages die faster every time.

Today transformational lives mostly in B2C: health, beauty, dieting. A secret way to pick stocks and you’ll be a millionaire in thirty days. All scams live at the transformational level.

Never lead with it in B2B, or use the word. Nobody will trust you to rip their business down to the studs.

21. Hope first, data last

Picture a funnel as a continuum. At the far end, on a spec sheet or a price list, there shouldn’t be any hope. Just data.

At the top, it’s the opposite. From the first moment there’s hope: this company can solve my problem, this product can get me from my negative present to my positive future.

Then a little data. Around the middle the proportion inverts. Less hope, more data. At the end, all data.

Skip hope at the start and you’ll struggle to hold attention long enough to reach the data.

22. Make the first ask baby-sized

At the top of the funnel, the threshold should be very small. Threshold is what you’re asking the reader to do. It’s the call to action.

Start tiny and get progressively bigger. The smallest threshold is feel this way. Next: click this little thing. Then look at this web page. Sign up for a webinar. Book a demo. Talk to sales.

Talk to sales is the biggest threshold there is. It should almost never be at the top of the funnel. The exception: something simple to understand, competing mainly on price, with a really big audience.

23. Give them a welcome distraction

Everyone’s day, even the busiest person’s, is broken into pieces with empty space in between. A few minutes between calls. Coffee. The bathroom.

A welcome distraction, unlike an interruption, fits in that space. Two reasons it works. Everyone needs a mental break and will go looking for one. And it gives a tiny sense of accomplishment. That’s why we delete email.

For us the accomplishment is a forward or a delegation: can you take a look at this? Or a click, or a moment reading something. They did something, and it felt good.

It’s welcome because it isn’t trying to interrupt a meeting. It’s there and ready. It may keep showing up until they do something with it.

24. Build the bridge out of rope

Treat any communication as a series of rope bridges. A rope bridge gets you across. It won’t bear much weight. Overload it and the person falls into the canyon.

Take email. The from name: Julia at Acme Corp beats Acme Corp marketing team. The subject line: with coworkers, the subject explains. In marketing and sales, its job is to get the email opened without lying. Allude, tease, be interesting. Don’t explain. If they think they know what’s inside, they won’t open it, and the bridge broke.

Then the body, whose job is to get the click. Then the call to action, which takes them to the easiest, lowest-friction, most persuasive next step.

Emails, web pages, voicemails, cold calls. Don’t put too much weight on any one bridge.

25. Use the channels your competitors abandoned

Your competitors have stopped using some old channels. Those channels are empty now. Whatever comes through is signal.

Physical sales letters. Postcards. TV, radio, newspapers. All forms of mail. Hardly anybody gets junk mail anymore. And the high-friction channels: showing up, giving talks, having a booth.

Don’t ignore a channel because it’s old. You might be the only company using it on that prospect this year. By definition, you stand out at least a little.

26. Get from the long list to the short list

On the long list, you’re one of many. In an RFP, five to twenty companies might make it. If you land there, it’s because you weren’t the kind of company that lands on the mid list.

The mid list is for companies big or noticeable enough to be a default option. They call you: we have an opportunity, please participate. You don’t have to go find it.

The short list is some combination of safe, noticeable, and memorable. Or the biggest.

Part 4: Words That Work

27. “Different” wins. “Unique” loses.

Don’t aim for unique. Aim for different, or for only.

Come in at the top of the funnel talking about how unique you are and here’s what the prospect knows: everything they’ve learned and every assumption they hold is now useless. They’d have to invest just to figure out what you do, whether it applies to them, and whether it applies now.

Different says seven of the eight things are the same, and look at the eighth. Seven things they’ve learned are still valid. They only invest a little.

Of the three openers, unique is weakest. Different is probably best and easiest. Only sits between: we came up with a whole new way to create value.

28. Get out of the junk drawer

In your kitchen, almost everything has one place. The coffee cup goes in the cupboard for cups. Anything without a category goes in the junk drawer.

First rule of marketing: don’t live in the junk drawer. Fit into a category.

Second rule, the one that makes marketing different from other business functions: you get to build brand new cupboards in the prospect’s mind, and live there. Often alone.

That’s what memorable means. When they need something like you, or they’re bored in line for coffee, you pop into their head, because you built a new cupboard.

Unless you’re the first or second biggest in a category, you don’t want to share a cupboard with everyone else. You’ll get compared. You’ll compete on price.

29. Be the horse lady

You’ve decided to talk to a therapist. You research five. Four have an office: you sit in a chair, they sit opposite, they ask questions, you talk.

The fifth is the horse lady. No office. A farm nearby. She puts you on an old gentle horse, gets on another, and the two of you walk a trail while she asks questions and you talk.

They all sell the same thing. Licensing, insurance, ethics, and board certifications pin them in. Same service, maybe the same price, since insurance reimburses.

Instantly, four get crushed into one amalgam. The horse lady gets her own category.

She won’t win everyone. Five options, you’d expect twenty percent each. She probably gets 22 or 23, and the rest sit at about 19. Anyone who’s run a small business knows that gap is the difference between getting by and six weeks in the Bahamas every year.

Being a category of one is valuable by itself. Everyone else has to compete on convenience and price. She preserves margin, and her marketing is way easier.

30. Say what they can’t or won’t say

In first contact marketing, you’re trying to find something your audience cares about that your competitors either won’t say or can’t say. That’s the holy grail.

A client once told me they call customers “partners.” He thought it set them apart. I told him: not much is guaranteed in life, but this is. Every one of your competitors is saying the exact same thing. It was trendy ten or fifteen years ago.

Can’t say: you’d have to change your company or offering to earn it.

Won’t say: it would burn their existing revenue model. They won’t invest in better customer service. They won’t sell to garages and nail salons because it isn’t glamorous. Or it would spook shareholders and investors.

You may not have the shareholders yet. That’s your new category.

31. The asymmetrics

There are about 24 ways David beats Goliath. I’ve catalogued them as the asymmetrics.

Fight on terrain where Goliath’s strengths don’t help. Use weapons he can’t defend against. Rely on speed if he’s slow, on density if he’s nimble. Do what he cannot or will not do, because it would wreck his brand, eat his revenue, force him to cannibalize or abandon part of the business, or be impossible to explain to the board.

Every company is strong in some ways and weak in others. Asymmetric means living in a category they won’t follow you into, or counter-positioning where they can’t, won’t, or shouldn’t come after you.

It doesn’t take long to scan two dozen lenses. Find the one to three that give a clear picture, then explore those as places to move or ways to fight.

32. Audit your assumptions

Assumptions are beliefs we treat like facts. The economy runs on them. So does every product category.

Over time, one or more of the assumptions under your category, industry, competitors, prospects, or company stops being true. Maybe people stop caring. Maybe everyone assumes it needs this many buttons or this speed, and it doesn’t.

Be the one who checks. List every assumption you can about the product, company, industry, and vertical, every couple of years. Test them.

The instant you find one that’s no longer true, that’s a great opportunity, especially if you’re first to move. Then ask what assumption has replaced it.

33. The three ways to open

If you don’t know how to open with strangers, there are four ways. One is by far the weakest, and it’s what everyone uses: we made something, or changed something. Sit tight and we’ll tell you about it. Never do that. It’s how almost every demo, technical webinar, and explainer video begins.

The other three share one message: part of your reality is broken, and we fix it.

1. Everyone said X was good. It never was.
2. X is good, but something has changed, or is about to, and it won’t be good anymore.
3. X is good for most people, but you’re different, so it isn’t good for you.

The silly milk version: everyone told us milk was good for us and it never was. Or a new law changed what goes into milk. Or milk is good, unless you have green eyes.

Much more persuasive than here’s what we did.

34. When you have several ICPs

More than one ICP is common in B2B. Three ways to handle it: merge, split, or create a new negative present.

Merge. Write out what each group hopes for, fears, and needs. Find what crosses. Everyone wants something different, but everyone is afraid of X. Then X is your first contact message, written once, appealing to many. Start with what they need and can do, not with what you want to say.

Split. If nothing crosses, go hard on segmentation. Each ICP gets its own color, tone, and style. Nobody should read two and think they’re similar. Lean into the difference, so each understands you know their particular negative present.

Create a new negative present. Two options. Name the nameless: they’re already suffering, but no one has systematized the problem and named it. Then become its expert. Or invent a problem you uniquely solve and publicize it. Naming the nameless is better. Without that, create one.

35. The halo niche

Almost every business can split its customers into two groups. Group A is impressive: big, famous, rich. Group B isn’t, but is impressed by the fact that group A hires you.

You’re a knee surgeon in Cleveland. Most of your patients are plumbers and delivery drivers. You’re also a preferred surgeon for Cleveland’s professional athletes, and they’re on your office wall.

No pro athlete hires you because you work on Joe the plumber. Joe hires you because you work on pro athletes. The athletes are your halo niche.

Halo customers bring in other customers. Tell everyone else about them. It’s instant expert status, safety, and hope. If she’s good enough for my favorite athlete’s million-dollar knees, she’s good enough for mine.

36. The second right answer

The temptation is to go with the first right answer, the first idea that clicks. You don’t even think of it as the first. You think of it as the answer.

More than ninety percent of the time, if you step away and come back thinking there’s something even better, you find the second right answer. It’s what separates your messaging from everybody else’s in the category.

It often comes from combining the first with something unrelated. A podcast from four years ago you haven’t thought about since. A line from an interview. If we combine this with that.

It takes as little as an hour. Lunch, then come back. Nine times out of ten there’s something beyond.

People will say it’s so simple. They’ll never say they’d never have come up with it. But they wouldn’t have.

37. Real strategy and marketing strategy

The ideal marketing strategy finds something competitors cannot and will not say, that the company can also back up. The company itself may not have to change anything.

Products, processes, and leadership stay the same. The company behind you, making and distributing and selling the thing, can be unaware of what you’re saying to the market. What you’re saying just doesn’t require them to change.

When a company has a real strategy, the messaging strategy is a child of it. Fantastic. Most don’t. Then you need a marketing strategy: something competitors can’t and won’t say, that doesn’t affect the business, that conveys hope, safety, and confidence, and that’s noticeable and memorable.

Not easy. Can take a while. Doable, without sounding like everyone else.

38. Underdog or other dog

Every company outside the top two in its category is either an underdog or an other dog.

An underdog has a plan and the fight to improve its circumstances. It has a strategy, or knows it needs one. It thinks about how it presents itself and how it’s perceived. It watches competitors, and its competitors talk about it.

An other dog is having its lunch eaten.

You have to decide which one you are. Not the other dog.

39. The invisible giant

You make real revenue by any objective standard. You’re nowhere near the top. Not one or two. You might aspire to five. You might be seven, nine, thirteen, fifteen.

Every time your salespeople call a new prospect, they have to explain: we exist. We’ve been around twenty-two years. We have four thousand employees. And the prospect says how can you be that big and I’ve never heard of you?

Two reasons. You haven’t worked out a strategy that gets you to number one or two in a category enough people care about. Or you’ve got the strategy but haven’t done the messaging. You haven’t shown you live and breathe the customer’s negative present.

Strategy problem, messaging problem, or both.

40. Know how you make your money

All profit comes from inefficiency. Either solving it or preserving it.

Most companies solve an inefficiency, eliminate it, or make it less friction-filled. Some preserve it. Landlords. Anyone hiding behind bureaucracy, patents, or professional licenses. They make things harder for everyone else, to keep competitors out or down and protect margins.

Neither is wrong. But know which one you are. If you preserve inefficiency, you shouldn’t talk like a company that eliminates it.

Part 5: Sales, Marketing, and the Inside of the Company

41. The difference between marketing and sales

Beyond the contract at the end, look at the tools.

Marketing’s toolset is built so a small number of people can talk to a large number. Advertising. Big events. Ten thousand emails this week.

Sales tools do the opposite. They take a large number of leads and whittle them down to a very small number of high-quality, likely buyers.

That’s the disconnect. No sales team will call a list of 8,000 people who downloaded a PDF and left a first name and a Gmail address. There could be good leads in there. As it stands, it’s useless. They don’t have the headcount to qualify 8,000 anyway.

Marketing thinks mass. Sales thinks quality. Someone has to bridge the air gap. Some companies give it a fancy name, like alignment. Underneath, the top-level purposes are different.

42. Marketing has a yes problem

Most departments have a no problem. No, we can’t include that feature this year. No, it isn’t in the plan. No, it doesn’t fit strategy. No budget to hire. No, we’re streamlining. Everywhere else, you’re hoping to find a yes person.

Marketing is the opposite. Marketing has a yes problem. Sure, we’ll include your department on the homepage. Sure, a statement about this. Sure, that customer segment too.

What marketing needs is a no person. Someone who says we’re not doing that. Or, more politically: sure, but not right now. We agreed on priorities with the board.

Marketing is often the opposite of the rest of the company.

43. Feelings are real. They aren’t reality.

In B2B we can rarely test externally. So people’s feelings and opinions get treated as truth, often decided by who has the most power or the highest title.

Your feelings aren’t reality. Neither are theirs. There’s usually some way to test, some metric or heuristic you can get your arms around. If testing means going live with your best shot, your job is to make prospects feel understood, because they have to feel understood before they try to understand you.

The head of finance may think your campaign is garbage. They’re not on the hook if it fails. If it works, they won’t remember they were against it. Revenue will be a big deal to them.

Revenue validates your decisions. Write this down somewhere: feelings are real but they aren’t reality.

44. Testing when your market is small

B2C brands can do destructive testing. Wreck a tiny slice of the market, so be it. B2C’s main problem is too many competitors. B2B’s main problem is too few potential customers, so you can’t burn through them testing.

There’s a solution, and it’s new. Large language models are very good at predicting audience responses, even for small customer sets. You can test messaging against simulated prospects and simulated ICPs and get a pretty good sense of how the recipient will react.

Ask them as if they’re in a focus group. What did you think of this deck? Would it get you a meeting? Does this headline hit what you’re worried about, even the things you don’t say aloud?

B2C could always test destructively. B2B had the more acute need for simulated audiences. Both got them at the same time.

Part 6: Creativity and Craft

45. The marketing arms race

B2B marketing has three pathways.

One: spend money. Works if you’re the biggest in your category, one or two. Ads, conventions, booths, mailers, extra SDRs, extra TV and radio. You have enough money that competitors can’t keep up. You don’t even need to be original.

Two: content marketing and inbound. For fifteen years, almost everyone else’s path. Hire an agency or freelancers to write blogs, posts, and use cases, then hope another company’s algorithm puts your message in front of the right person at the right time. Stated plainly, it sounds crazy.

In the last three years it collapsed. The biggest, the middle, and the one-person shop can all produce unlimited keyword-optimized content on a perfect schedule. AI changed it. Every inbox and feed is flooded. Prospects tuned out. They don’t go looking. They ask the AI directly.

Three: creativity. Hard creative thinking, not woo-woo. It was always tricky. Now it’s the only one left. If everyone has the same tool, nobody has an advantage, and there’s none in doing content faster or at higher volume.

You can’t easily say that in a boardroom. Boards, leadership, and private equity hate unquantifiable risk. And your team probably has no track record of hard creative thinking applied to inventive messaging. Content did well for a long time. And there wasn’t enough work for these people, the iconoclasts who question every word. They work freelance or at agencies. Good ones are rare and expensive, and should be.

I wish I could tell you there’s a tool and three hires that make you good to go. It doesn’t exist. Maybe it never did.

46. Money can hide a bad message

If your outreach only works because of scale, anything would have worked.

If you’re one of the two or three biggest, your main strategy isn’t creativity. It’s spending money. Blanket the market. Even a poor message works if you repeat it and can afford to forever.

Everyone else has to be inventive. Thinking, design, and taste are the only resources you have to carve out your part of the market.

No money? You need a message that works at small scale.

47. Creative thinking is mechanical. Creativity is capture.

Creative thinking is a mechanical process. Tools, exercises, group activities. Give three people a product, ask for fifty names, and they’ll return in half an hour with fifty.

Creativity is the opposite. It’s not about generating outward. It’s about capturing ideas when they occur.

So the most important thing is a reliable, low-friction way to capture. You won’t remember it, even if you tell yourself I have to remember that, that’s what we needed to say. You’re driving. You’re on the phone. Gone.

Everyone has lost an insight. Everyone. I have a pretty extensive process for never losing one, and I still lose them.

Prime it. Read, think, let it bake for a day or two. Take a super long walk and tell yourself it’s an hour no matter what. I don’t know why it works. Brains served an inescapable sixty minutes seem to hand something up.

You don’t teach people to be creative. Everyone already is. You teach them to capture rigorously, so at the end of the week’s review they say I don’t remember thinking that, and it turns out I solved this two days ago.

48. Treat ideas as objects

The number one tool for creative thinking is anything that lets you treat thoughts as physical, three-dimensional objects.

For some people it’s paper, index cards, post-its on a wall or window. Whiteboards.

In the digital world, look for an outlining tool. Not an outline. A Word document or a slide is an outline. An outlining tool lets you pick up a bullet, drag it, and drop it where you want. Mind maps, Dynalist, OmniOutliner, Craft, Workflowy.

It matters twice. First for generating ideas fast. Second for the phase after you run out. I did eleven and then hit a pause. You look at what you’ve done and it makes more sense over there, these three go to the side.

Whatever comes out of your head should be an object you can move, destroy, and reorganize.

Part 7: Proof of Effort

49. Prospects can tell how hard you tried

If you skip good design and good persuasive writing, you look like you’re not taking the prospect seriously. Or that you can’t.

Marketing is ridiculously cheap for what it returns, until you get into paid spend. Superior persuasive copywriting doesn’t cost that much.

And we’ve all gotten very good at spotting AI writing. The clunkiness. Over-explaining what didn’t need it, under-explaining what did.

Prospects sense instantly how much effort went in. If you didn’t put much in, they assume you can’t, or you’re cheap and won’t. You might be fine with that. But the more expensive the thing you sell, the more it matters to show you put time, effort, and money into presenting yourself right.

50. When to use AI

If a piece is more valuable to the reader because a human wrote it, and understands humans, have a person write it. For everything else, have an AI write it.

That may sound backwards coming from me. It’s what I mean. A lot of generic blog posts. Anything purely informational. A minor variation of something you wrote before. None of it is more valuable because a person wrote it. It’s facts and generic writing.

Unless you need to make somebody feel something and do something. Then good copywriting is still only written by people, for now.

Everything else, why not.

The short version

Boil them down and you get one sentence: we understand your negative present and we can shortcut you to a positive future. Prove you’re safe. Fill the confidence bucket. Do their thinking before you arrive. Ask for something small.

Say what your competitors won’t. Then find the second right answer.

Do the work where they can see it.