Jason Cohen
@asmartbear.com
Keyword, buzzword, half-truth, adjective, hey look at me! (founder of two unicorns: http://WPEngine.com, http://SmartBear.com).
Writing for 18 years at: https://longform.asmartbear.com
Writing for 18 years at: https://longform.asmartbear.com
The US has 200,000 mid-sized companies (annual revenues $10M-$1B) and 5,300 large (>$1B revenue).
So you might think it makes sense to target mid (big N) but not large (small N and difficult).
That might still be wrong though:
So you might think it makes sense to target mid (big N) but not large (small N and difficult).
That might still be wrong though:
The mid-market briar patch
Mid-sized companies: Small enough to have small budgets, big enough for bureaucratic nightmares.
longform.asmartbear.com
December 28, 2025 at 4:31 PM
The US has 200,000 mid-sized companies (annual revenues $10M-$1B) and 5,300 large (>$1B revenue).
So you might think it makes sense to target mid (big N) but not large (small N and difficult).
That might still be wrong though:
So you might think it makes sense to target mid (big N) but not large (small N and difficult).
That might still be wrong though:
Koan #29
“What’s the lifestyle of a bootstrapper?”
“Working 80 hrs/week; tired but truly living.”
“A VC-funded founder?”
“Optimistically changing the world.”
“A solo CPA?”
“Good money, fun on weekends.”
“So, which one is a ‘lifestyle business?’”
And the student was enlightened.
“What’s the lifestyle of a bootstrapper?”
“Working 80 hrs/week; tired but truly living.”
“A VC-funded founder?”
“Optimistically changing the world.”
“A solo CPA?”
“Good money, fun on weekends.”
“So, which one is a ‘lifestyle business?’”
And the student was enlightened.
December 27, 2025 at 11:01 PM
Koan #29
“What’s the lifestyle of a bootstrapper?”
“Working 80 hrs/week; tired but truly living.”
“A VC-funded founder?”
“Optimistically changing the world.”
“A solo CPA?”
“Good money, fun on weekends.”
“So, which one is a ‘lifestyle business?’”
And the student was enlightened.
“What’s the lifestyle of a bootstrapper?”
“Working 80 hrs/week; tired but truly living.”
“A VC-funded founder?”
“Optimistically changing the world.”
“A solo CPA?”
“Good money, fun on weekends.”
“So, which one is a ‘lifestyle business?’”
And the student was enlightened.
The Mayans' model of the universe was laughably wrong, yet they predicted eclipses with impressive accuracy.
A striking example that a model can be completely wrong about 'why' yet still yield accurate predictions.
What about the models we use in business?
A striking example that a model can be completely wrong about 'why' yet still yield accurate predictions.
What about the models we use in business?
All pretty models are wrong, but some ugly models are useful
Identifying useful frameworks for companies, strategy, markets, and organizations, instead of those that just look pretty in PowerPoint.
longform.asmartbear.com
December 27, 2025 at 11:01 PM
The Mayans' model of the universe was laughably wrong, yet they predicted eclipses with impressive accuracy.
A striking example that a model can be completely wrong about 'why' yet still yield accurate predictions.
What about the models we use in business?
A striking example that a model can be completely wrong about 'why' yet still yield accurate predictions.
What about the models we use in business?
It's difficult to be simple, in writing or speaking, even after thinking hard and iterating.
Is it muddled thinking? Or a lack of decision-making.
Saying what's important means deciding against so much more.
Which is yet another reason why it’s useful to do it.
Is it muddled thinking? Or a lack of decision-making.
Saying what's important means deciding against so much more.
Which is yet another reason why it’s useful to do it.
What makes a strategy great
Most so-called “strategies” are vague, wishful thinking, written once and never seen again. Don’t do that. These are the characteristics of great strategy.
longform.asmartbear.com
December 27, 2025 at 5:06 PM
It's difficult to be simple, in writing or speaking, even after thinking hard and iterating.
Is it muddled thinking? Or a lack of decision-making.
Saying what's important means deciding against so much more.
Which is yet another reason why it’s useful to do it.
Is it muddled thinking? Or a lack of decision-making.
Saying what's important means deciding against so much more.
Which is yet another reason why it’s useful to do it.
What is a brand, if not a consistent repetition of a specific message?
Or culture, if not repetition of specific values?
Yes, repeat yourself beyond reason.
Or culture, if not repetition of specific values?
Yes, repeat yourself beyond reason.
December 27, 2025 at 12:00 AM
What is a brand, if not a consistent repetition of a specific message?
Or culture, if not repetition of specific values?
Yes, repeat yourself beyond reason.
Or culture, if not repetition of specific values?
Yes, repeat yourself beyond reason.
When I was in high school, it was 100% clear that my career would be in writing code, 70% clear that I would start a company someday (hate authority, hate being told what to do), and 0% clear what topics/markets I would end up choosing.
What are your 100/70/0 things?
What are your 100/70/0 things?
December 26, 2025 at 7:36 PM
When I was in high school, it was 100% clear that my career would be in writing code, 70% clear that I would start a company someday (hate authority, hate being told what to do), and 0% clear what topics/markets I would end up choosing.
What are your 100/70/0 things?
What are your 100/70/0 things?
“𝗚𝗼𝗼𝗱 𝗲𝗻𝗼𝘂𝗴𝗵” 𝗶𝘀𝗻'𝘁.
If you agree, you have part of what it takes to be successful.
But when you aim that obsessive gun at 𝘦𝘷𝘦𝘳𝘺𝘵𝘩𝘪𝘯𝘨, you don’t have enough time and attention for the most important things.
How I navigate:
If you agree, you have part of what it takes to be successful.
But when you aim that obsessive gun at 𝘦𝘷𝘦𝘳𝘺𝘵𝘩𝘪𝘯𝘨, you don’t have enough time and attention for the most important things.
How I navigate:
Being who you are, while becoming better
We’re told “be yourself” to seek happiness and success. But what if “being yourself” also means striving to become better? What is “yourself?”
longform.asmartbear.com
December 26, 2025 at 7:36 PM
“𝗚𝗼𝗼𝗱 𝗲𝗻𝗼𝘂𝗴𝗵” 𝗶𝘀𝗻'𝘁.
If you agree, you have part of what it takes to be successful.
But when you aim that obsessive gun at 𝘦𝘷𝘦𝘳𝘺𝘵𝘩𝘪𝘯𝘨, you don’t have enough time and attention for the most important things.
How I navigate:
If you agree, you have part of what it takes to be successful.
But when you aim that obsessive gun at 𝘦𝘷𝘦𝘳𝘺𝘵𝘩𝘪𝘯𝘨, you don’t have enough time and attention for the most important things.
How I navigate:
Rewriting something in your own words is more valuable than it sounds.
You internalize it.
You tweak its meaning to match your philosophy and experience.
You put your own style on it.
You repeat a good idea, which it deserves.
Lesson for social media and newsletters.
You internalize it.
You tweak its meaning to match your philosophy and experience.
You put your own style on it.
You repeat a good idea, which it deserves.
Lesson for social media and newsletters.
December 26, 2025 at 7:36 PM
Rewriting something in your own words is more valuable than it sounds.
You internalize it.
You tweak its meaning to match your philosophy and experience.
You put your own style on it.
You repeat a good idea, which it deserves.
Lesson for social media and newsletters.
You internalize it.
You tweak its meaning to match your philosophy and experience.
You put your own style on it.
You repeat a good idea, which it deserves.
Lesson for social media and newsletters.
What if you stop now, but you were just on the edge of a breakthrough?
What if you keep going and never get anywhere, but had you stopped, you would have found a breakthrough?
Both will always be true.
(1/2)
What if you keep going and never get anywhere, but had you stopped, you would have found a breakthrough?
Both will always be true.
(1/2)
Stubborn Visionaries & Pigheaded Fools
How do you know when to stop, versus when to push through? You don’t, not even in hindsight. But these guiding questions can help.
longform.asmartbear.com
December 25, 2025 at 11:38 PM
What if you stop now, but you were just on the edge of a breakthrough?
What if you keep going and never get anywhere, but had you stopped, you would have found a breakthrough?
Both will always be true.
(1/2)
What if you keep going and never get anywhere, but had you stopped, you would have found a breakthrough?
Both will always be true.
(1/2)
“Dude, you’re weird.”
Good. Not-weird is boring.
Good. Not-weird is boring.
December 25, 2025 at 5:14 PM
“Dude, you’re weird.”
Good. Not-weird is boring.
Good. Not-weird is boring.
Ironically we undervalue our greatest superpowers exactly because they come so easily to us.
So we don’t think it’s impressive, special, or interesting.
But it is the fact that it’s so easy for us that makes them superpowers.
So we don’t think it’s impressive, special, or interesting.
But it is the fact that it’s so easy for us that makes them superpowers.
December 24, 2025 at 11:48 PM
Ironically we undervalue our greatest superpowers exactly because they come so easily to us.
So we don’t think it’s impressive, special, or interesting.
But it is the fact that it’s so easy for us that makes them superpowers.
So we don’t think it’s impressive, special, or interesting.
But it is the fact that it’s so easy for us that makes them superpowers.
“Launching” is over-rated.
Most of the time it's a flop; a huge waste of time, and hurts morale.
Even in the best case, you still have to earn customers systematically for the next 3 years.
Just work on THAT.
Most of the time it's a flop; a huge waste of time, and hurts morale.
Even in the best case, you still have to earn customers systematically for the next 3 years.
Just work on THAT.
December 24, 2025 at 11:48 PM
“Launching” is over-rated.
Most of the time it's a flop; a huge waste of time, and hurts morale.
Even in the best case, you still have to earn customers systematically for the next 3 years.
Just work on THAT.
Most of the time it's a flop; a huge waste of time, and hurts morale.
Even in the best case, you still have to earn customers systematically for the next 3 years.
Just work on THAT.
What story is your price telling?
Telling your customers they’re getting a steal?
Reassuring them they're investing in quality?
Accessible? Trusted? Scaled? Personal?
Pricing is positioning:
Telling your customers they’re getting a steal?
Reassuring them they're investing in quality?
Accessible? Trusted? Scaled? Personal?
Pricing is positioning:
Pricing determines your business model
Pricing is inextricably linked to brand, product, and purchasing decisions. It cannot be “figured out later,” because it determines your business model today.
longform.asmartbear.com
December 24, 2025 at 3:57 PM
What story is your price telling?
Telling your customers they’re getting a steal?
Reassuring them they're investing in quality?
Accessible? Trusted? Scaled? Personal?
Pricing is positioning:
Telling your customers they’re getting a steal?
Reassuring them they're investing in quality?
Accessible? Trusted? Scaled? Personal?
Pricing is positioning:
The dream for many consulting companies is to build up a stable profit and then build a product.
Almost none accomplish either.
These are some of the reasons, and some things to do about it:
Almost none accomplish either.
These are some of the reasons, and some things to do about it:
The unfortunate math behind consulting companies
Hiring even one person creates a lot less profit than you’d think, and launching a product rarely works out. Here are some tips for consulting companies.
longform.asmartbear.com
December 23, 2025 at 9:21 PM
The dream for many consulting companies is to build up a stable profit and then build a product.
Almost none accomplish either.
These are some of the reasons, and some things to do about it:
Almost none accomplish either.
These are some of the reasons, and some things to do about it:
Speed is one of the few advantages startups have. So use it.
Most things only have to be "good enough;" speed solves for that.
For the things that are wrong, "speed" causes you to find that out sooner, and fix it sooner.
Most things only have to be "good enough;" speed solves for that.
For the things that are wrong, "speed" causes you to find that out sooner, and fix it sooner.
December 23, 2025 at 7:17 PM
Speed is one of the few advantages startups have. So use it.
Most things only have to be "good enough;" speed solves for that.
For the things that are wrong, "speed" causes you to find that out sooner, and fix it sooner.
Most things only have to be "good enough;" speed solves for that.
For the things that are wrong, "speed" causes you to find that out sooner, and fix it sooner.
Some claim larger companies have lower risk-tolerance because they lost the ability to take bets.
But also, now they actually have something to lose.
Also, the "success" case has to be larger.
This is due to competence, not incompetence.
But also, now they actually have something to lose.
Also, the "success" case has to be larger.
This is due to competence, not incompetence.
The fundamental forces of scale
These forces make larger companies slower and more difficult to execute, but also more effective when harnessed and leveraged.
longform.asmartbear.com
December 23, 2025 at 3:20 PM
Some claim larger companies have lower risk-tolerance because they lost the ability to take bets.
But also, now they actually have something to lose.
Also, the "success" case has to be larger.
This is due to competence, not incompetence.
But also, now they actually have something to lose.
Also, the "success" case has to be larger.
This is due to competence, not incompetence.
If all the decisions before you are bad, one path is to pick the least-bad.
Some say forms-of-government are like that.
Ideally, though, you see this as a signal to "create more ideas" rather than settle on a bad one
Some say forms-of-government are like that.
Ideally, though, you see this as a signal to "create more ideas" rather than settle on a bad one
December 23, 2025 at 1:19 AM
If all the decisions before you are bad, one path is to pick the least-bad.
Some say forms-of-government are like that.
Ideally, though, you see this as a signal to "create more ideas" rather than settle on a bad one
Some say forms-of-government are like that.
Ideally, though, you see this as a signal to "create more ideas" rather than settle on a bad one
Your business will be sustainable or not based on its long-term strategy.
You will make a sale tomorrow or not based on what you can accomplish today.
How to do path for both:
You will make a sale tomorrow or not based on what you can accomplish today.
How to do path for both:
Quarterly strategic planning using the fairytale structure
Traditional fairytale structure fits naturally in our brains, and thus can guide strategic problem-analysis, and a plan that everyone understands.
longform.asmartbear.com
December 23, 2025 at 1:19 AM
Your business will be sustainable or not based on its long-term strategy.
You will make a sale tomorrow or not based on what you can accomplish today.
How to do path for both:
You will make a sale tomorrow or not based on what you can accomplish today.
How to do path for both:
Koan #18
Edison failed to find the right filament.
Jordan failed to sink the game-winning shot.
Dr Seuss failed to get published.
Einstein failed to get a professorship.
Lincoln failed 8 elections.
Van Gogh failed to sell more than 1 painting.
And the student was enlightened.
Edison failed to find the right filament.
Jordan failed to sink the game-winning shot.
Dr Seuss failed to get published.
Einstein failed to get a professorship.
Lincoln failed 8 elections.
Van Gogh failed to sell more than 1 painting.
And the student was enlightened.
Stop saying “fail”
Language shapes our perception of setbacks. Use words other than “failure” to describe situations and to suggest the next step.
longform.asmartbear.com
December 23, 2025 at 1:19 AM
Koan #18
Edison failed to find the right filament.
Jordan failed to sink the game-winning shot.
Dr Seuss failed to get published.
Einstein failed to get a professorship.
Lincoln failed 8 elections.
Van Gogh failed to sell more than 1 painting.
And the student was enlightened.
Edison failed to find the right filament.
Jordan failed to sink the game-winning shot.
Dr Seuss failed to get published.
Einstein failed to get a professorship.
Lincoln failed 8 elections.
Van Gogh failed to sell more than 1 painting.
And the student was enlightened.
Koan #18
Edison failed to find the right filament.
Jordan failed to sink the game-winning shot.
Dr Seuss failed to get published.
Einstein failed to get a professorship.
Lincoln failed 8 elections.
Van Gogh failed to sell more than 1 painting.
And the student was enlightened.
Edison failed to find the right filament.
Jordan failed to sink the game-winning shot.
Dr Seuss failed to get published.
Einstein failed to get a professorship.
Lincoln failed 8 elections.
Van Gogh failed to sell more than 1 painting.
And the student was enlightened.
Stop saying “fail”
Language shapes our perception of setbacks. Use words other than “failure” to describe situations and to suggest the next step.
longform.asmartbear.com
December 22, 2025 at 9:52 PM
Koan #18
Edison failed to find the right filament.
Jordan failed to sink the game-winning shot.
Dr Seuss failed to get published.
Einstein failed to get a professorship.
Lincoln failed 8 elections.
Van Gogh failed to sell more than 1 painting.
And the student was enlightened.
Edison failed to find the right filament.
Jordan failed to sink the game-winning shot.
Dr Seuss failed to get published.
Einstein failed to get a professorship.
Lincoln failed 8 elections.
Van Gogh failed to sell more than 1 painting.
And the student was enlightened.
“We have no competition.”
Always a huge red flag.
If they mean it, it’s oblivious ignorance or a failed attempt at declaring how “differentiated” they are.
Or they think they’re getting away with a lie.
Usually it’s the failed attempt.
Don’t be that person.
Always a huge red flag.
If they mean it, it’s oblivious ignorance or a failed attempt at declaring how “differentiated” they are.
Or they think they’re getting away with a lie.
Usually it’s the failed attempt.
Don’t be that person.
December 22, 2025 at 4:09 AM
“We have no competition.”
Always a huge red flag.
If they mean it, it’s oblivious ignorance or a failed attempt at declaring how “differentiated” they are.
Or they think they’re getting away with a lie.
Usually it’s the failed attempt.
Don’t be that person.
Always a huge red flag.
If they mean it, it’s oblivious ignorance or a failed attempt at declaring how “differentiated” they are.
Or they think they’re getting away with a lie.
Usually it’s the failed attempt.
Don’t be that person.
Koan #68
“Our product is better than Z!”
“But is it great?”
“Our customers say it’s better than Z.”
“But is it great?”
“We have positive reviews on a website.”
“To which strangers have you delegated the judgement of whether it is great?”
And the student was enlightened.
“Our product is better than Z!”
“But is it great?”
“Our customers say it’s better than Z.”
“But is it great?”
“We have positive reviews on a website.”
“To which strangers have you delegated the judgement of whether it is great?”
And the student was enlightened.
December 21, 2025 at 11:02 PM
Koan #68
“Our product is better than Z!”
“But is it great?”
“Our customers say it’s better than Z.”
“But is it great?”
“We have positive reviews on a website.”
“To which strangers have you delegated the judgement of whether it is great?”
And the student was enlightened.
“Our product is better than Z!”
“But is it great?”
“Our customers say it’s better than Z.”
“But is it great?”
“We have positive reviews on a website.”
“To which strangers have you delegated the judgement of whether it is great?”
And the student was enlightened.
When A/B tests are inconclusive, we like to let them run for longer “just in case.”
No, you’re wasting time.
If the difference was big enough to matter to your business, you’d know already.
The math:
No, you’re wasting time.
If the difference was big enough to matter to your business, you’d know already.
The math:
Easy statistics for A/B testing and hamsters
A/B testing tools often lie about whether something is “statistically significant.” Here’s an extremely simple, mathematically sound formula to compute it for yourself.
longform.asmartbear.com
December 21, 2025 at 3:09 PM
When A/B tests are inconclusive, we like to let them run for longer “just in case.”
No, you’re wasting time.
If the difference was big enough to matter to your business, you’d know already.
The math:
No, you’re wasting time.
If the difference was big enough to matter to your business, you’d know already.
The math:
They are not hoping that you fail.
They are not waiting for you to fail.
They’re not thinking about you at all.
Is that de-motivating?
Or is it liberating.
Of course you have something to prove, but it is to yourself, not to them. 
They are not waiting for you to fail.
They’re not thinking about you at all.
Is that de-motivating?
Or is it liberating.
Of course you have something to prove, but it is to yourself, not to them. 
December 20, 2025 at 10:44 PM
They are not hoping that you fail.
They are not waiting for you to fail.
They’re not thinking about you at all.
Is that de-motivating?
Or is it liberating.
Of course you have something to prove, but it is to yourself, not to them. 
They are not waiting for you to fail.
They’re not thinking about you at all.
Is that de-motivating?
Or is it liberating.
Of course you have something to prove, but it is to yourself, not to them. 
Categorize your product’s attributes (e.g. speed, quality, security, integrations, depth of features, design, …) into three buckets:
• 10x -- you’ll never stop maximizing these, even once you’re better than all competitors.
• 1x -- you have this capability.
(1/6)
• 10x -- you’ll never stop maximizing these, even once you’re better than all competitors.
• 1x -- you have this capability.
(1/6)
What makes a strategy great
Most so-called “strategies” are vague, wishful thinking, written once and never seen again. Don’t do that. These are the characteristics of great strategy.
longform.asmartbear.com
December 20, 2025 at 7:06 PM
Categorize your product’s attributes (e.g. speed, quality, security, integrations, depth of features, design, …) into three buckets:
• 10x -- you’ll never stop maximizing these, even once you’re better than all competitors.
• 1x -- you have this capability.
(1/6)
• 10x -- you’ll never stop maximizing these, even once you’re better than all competitors.
• 1x -- you have this capability.
(1/6)