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
If you hire people, and then tell them how to do every little thing, then you're building an organization that will never be better than you, and never have better ideas.
Your job is to do exactly the opposite.
Your job is to do exactly the opposite.
November 30, 2025 at 10:36 PM
If you hire people, and then tell them how to do every little thing, then you're building an organization that will never be better than you, and never have better ideas.
Your job is to do exactly the opposite.
Your job is to do exactly the opposite.
Annual billing transforms your finances.
But. once you're at scale, "annual" is a net-negative, because you no longer value the cash-flow, but you permanently lack the revenue.
(Still worth it.)
Numbers in the article:
But. once you're at scale, "annual" is a net-negative, because you no longer value the cash-flow, but you permanently lack the revenue.
(Still worth it.)
Numbers in the article:
How annual pre-pay creates an infinite marketing budget
Dozens of founders have used this technique to transform the cash-flow of their businesses. Now it’s your turn.
longform.asmartbear.com
November 30, 2025 at 3:20 PM
Annual billing transforms your finances.
But. once you're at scale, "annual" is a net-negative, because you no longer value the cash-flow, but you permanently lack the revenue.
(Still worth it.)
Numbers in the article:
But. once you're at scale, "annual" is a net-negative, because you no longer value the cash-flow, but you permanently lack the revenue.
(Still worth it.)
Numbers in the article:
As you age, you realize you're not "the best" at every role, but maybe only 2-3 out of 50.
For many roles, your mix of strengths and weaknesses make you downright bad at it.
Sometimes, we keep those roles anyway.
Bad for the company, and bad leadership.
For many roles, your mix of strengths and weaknesses make you downright bad at it.
Sometimes, we keep those roles anyway.
Bad for the company, and bad leadership.
November 30, 2025 at 3:20 PM
As you age, you realize you're not "the best" at every role, but maybe only 2-3 out of 50.
For many roles, your mix of strengths and weaknesses make you downright bad at it.
Sometimes, we keep those roles anyway.
Bad for the company, and bad leadership.
For many roles, your mix of strengths and weaknesses make you downright bad at it.
Sometimes, we keep those roles anyway.
Bad for the company, and bad leadership.
After high retention, the most powerful growth lever is NRR.
Almost all public SaaS companies are NRR ≥ 100%, with median ≥110%, because otherwise their Max MRR ceiling would be too low.
Not just VC-backed companies, also for solopreneurs.
See article for details:
Almost all public SaaS companies are NRR ≥ 100%, with median ≥110%, because otherwise their Max MRR ceiling would be too low.
Not just VC-backed companies, also for solopreneurs.
See article for details:
Max MRR: Your growth ceiling
Your company will stop growing sooner than you think. The “Max MRR” metric predicts revenue plateaus based on churn and new revenue.
longform.asmartbear.com
November 30, 2025 at 3:20 PM
After high retention, the most powerful growth lever is NRR.
Almost all public SaaS companies are NRR ≥ 100%, with median ≥110%, because otherwise their Max MRR ceiling would be too low.
Not just VC-backed companies, also for solopreneurs.
See article for details:
Almost all public SaaS companies are NRR ≥ 100%, with median ≥110%, because otherwise their Max MRR ceiling would be too low.
Not just VC-backed companies, also for solopreneurs.
See article for details:
Great lines from a recent Ton Dobbe newsletter (link below):
Here’s what I see with most SaaS sales teams: They answer questions prospects aren’t asking.
“Here’s HOW our product works.”
“Here’s WHAT it can do.”
“Here’s why we’re BETTER than them.”
(1/3)
Here’s what I see with most SaaS sales teams: They answer questions prospects aren’t asking.
“Here’s HOW our product works.”
“Here’s WHAT it can do.”
“Here’s why we’re BETTER than them.”
(1/3)
November 29, 2025 at 2:57 PM
Great lines from a recent Ton Dobbe newsletter (link below):
Here’s what I see with most SaaS sales teams: They answer questions prospects aren’t asking.
“Here’s HOW our product works.”
“Here’s WHAT it can do.”
“Here’s why we’re BETTER than them.”
(1/3)
Here’s what I see with most SaaS sales teams: They answer questions prospects aren’t asking.
“Here’s HOW our product works.”
“Here’s WHAT it can do.”
“Here’s why we’re BETTER than them.”
(1/3)
I obsess over every detail. Every pixel, every word.
For overall throughput, this is a bad thing. But it’s a good thing for the end product being fully myself, unique, identifiable. (“Best” only in the eye of the beholder.)
Limit total “things”, so you can be excellent on each “thing”.
For overall throughput, this is a bad thing. But it’s a good thing for the end product being fully myself, unique, identifiable. (“Best” only in the eye of the beholder.)
Limit total “things”, so you can be excellent on each “thing”.
November 28, 2025 at 11:08 PM
I obsess over every detail. Every pixel, every word.
For overall throughput, this is a bad thing. But it’s a good thing for the end product being fully myself, unique, identifiable. (“Best” only in the eye of the beholder.)
Limit total “things”, so you can be excellent on each “thing”.
For overall throughput, this is a bad thing. But it’s a good thing for the end product being fully myself, unique, identifiable. (“Best” only in the eye of the beholder.)
Limit total “things”, so you can be excellent on each “thing”.
You can’t charge $1 for delivering $1 of value.
Maybe you can charge $1 for $3, but with risk and overhead… probably not.
You need to deliver $10 for every $1.
P.S. You don’t define “value.” The customer does.
Maybe you can charge $1 for $3, but with risk and overhead… probably not.
You need to deliver $10 for every $1.
P.S. You don’t define “value.” The customer does.
November 28, 2025 at 8:01 PM
You can’t charge $1 for delivering $1 of value.
Maybe you can charge $1 for $3, but with risk and overhead… probably not.
You need to deliver $10 for every $1.
P.S. You don’t define “value.” The customer does.
Maybe you can charge $1 for $3, but with risk and overhead… probably not.
You need to deliver $10 for every $1.
P.S. You don’t define “value.” The customer does.
Prefer advice that challenges you to think, ask tough questions, and play to your strengths.
That's how you'll outsmart Survivor Bias, which plagues most advice:
That's how you'll outsmart Survivor Bias, which plagues most advice:
Business Advice Plagued by Survivor Bias
Advice from “successful entrepreneurs” might be unreliable due to Survivor Bias. What’s real, and what’s random?
longform.asmartbear.com
November 28, 2025 at 3:50 PM
Prefer advice that challenges you to think, ask tough questions, and play to your strengths.
That's how you'll outsmart Survivor Bias, which plagues most advice:
That's how you'll outsmart Survivor Bias, which plagues most advice:
Your failed startup DOES define you.
It means you had the guts to try something, which means you're "a person who has the guts to try hard things,” which bodes well for the rest of your life.
Now, embody that person, and continue to do gutsy things!
It means you had the guts to try something, which means you're "a person who has the guts to try hard things,” which bodes well for the rest of your life.
Now, embody that person, and continue to do gutsy things!
November 28, 2025 at 5:17 AM
Your failed startup DOES define you.
It means you had the guts to try something, which means you're "a person who has the guts to try hard things,” which bodes well for the rest of your life.
Now, embody that person, and continue to do gutsy things!
It means you had the guts to try something, which means you're "a person who has the guts to try hard things,” which bodes well for the rest of your life.
Now, embody that person, and continue to do gutsy things!
Healthy:
Getting something off your chest in a safe environment, without everyone trying to solve it.
Unhealthy:
Complaining, others chiming in and trying to fix someone else’s problem.
How to do it right:
Getting something off your chest in a safe environment, without everyone trying to solve it.
Unhealthy:
Complaining, others chiming in and trying to fix someone else’s problem.
How to do it right:
Productive meeting activities: Leverage the team, empower the individual
Meetings are most productive when we create something that none of us could have created alone. Here are several ways to use meeting time wisely.
longform.asmartbear.com
November 27, 2025 at 9:22 PM
Healthy:
Getting something off your chest in a safe environment, without everyone trying to solve it.
Unhealthy:
Complaining, others chiming in and trying to fix someone else’s problem.
How to do it right:
Getting something off your chest in a safe environment, without everyone trying to solve it.
Unhealthy:
Complaining, others chiming in and trying to fix someone else’s problem.
How to do it right:
“We’re killing the competition!”
Is that a statement about you, or them?
Is that a statement about your customers, or some other company that neither you nor your customers are doing business with?
Stay focused on what matters most.
Is that a statement about you, or them?
Is that a statement about your customers, or some other company that neither you nor your customers are doing business with?
Stay focused on what matters most.
November 27, 2025 at 4:35 PM
“We’re killing the competition!”
Is that a statement about you, or them?
Is that a statement about your customers, or some other company that neither you nor your customers are doing business with?
Stay focused on what matters most.
Is that a statement about you, or them?
Is that a statement about your customers, or some other company that neither you nor your customers are doing business with?
Stay focused on what matters most.
If your home page and landing pages doesn’t use language that you and your customers actually use, why did you do that?
If you read it aloud and it’s awkward, why did you do that?
There 𝘢𝘳𝘦 legit reasons… but is that really why you did that?
If you read it aloud and it’s awkward, why did you do that?
There 𝘢𝘳𝘦 legit reasons… but is that really why you did that?
November 26, 2025 at 11:57 PM
If your home page and landing pages doesn’t use language that you and your customers actually use, why did you do that?
If you read it aloud and it’s awkward, why did you do that?
There 𝘢𝘳𝘦 legit reasons… but is that really why you did that?
If you read it aloud and it’s awkward, why did you do that?
There 𝘢𝘳𝘦 legit reasons… but is that really why you did that?
Make a product that people still buy for in a recession.
Downgrades are OK, but not cancels.
Because this means you’re solving a 𝘳𝘦𝘢𝘭 problem, sufficiently.
And you’ll survive anything.
Downgrades are OK, but not cancels.
Because this means you’re solving a 𝘳𝘦𝘢𝘭 problem, sufficiently.
And you’ll survive anything.
November 26, 2025 at 8:03 PM
Make a product that people still buy for in a recession.
Downgrades are OK, but not cancels.
Because this means you’re solving a 𝘳𝘦𝘢𝘭 problem, sufficiently.
And you’ll survive anything.
Downgrades are OK, but not cancels.
Because this means you’re solving a 𝘳𝘦𝘢𝘭 problem, sufficiently.
And you’ll survive anything.
If you’ve identified a real problem that real people actually want to spend real money to solve…
…but then you describe it using your own language instead of the language those customers use to describe it…
…even if their language is imprecise and even incorrect…
(1/2)
…but then you describe it using your own language instead of the language those customers use to describe it…
…even if their language is imprecise and even incorrect…
(1/2)
Disentangling the three languages: Customers, Product, Business
Stop talking past each other. Translate between the three “languages” of customer desires, product features, and business goals.
longform.asmartbear.com
November 26, 2025 at 5:30 PM
If you’ve identified a real problem that real people actually want to spend real money to solve…
…but then you describe it using your own language instead of the language those customers use to describe it…
…even if their language is imprecise and even incorrect…
(1/2)
…but then you describe it using your own language instead of the language those customers use to describe it…
…even if their language is imprecise and even incorrect…
(1/2)
When you turn down a lucrative deal because it doesn’t fit your vision or strategy, that’s not a missed opportunity.
That’s proof that you actually have a vision or strategy.
More like that:
That’s proof that you actually have a vision or strategy.
More like that:
The “errors” that mean you’re doing it right
Some things appear to be mistakes, but in fact should be celebrated as the expected outcomes of great decisions.
longform.asmartbear.com
November 25, 2025 at 10:36 PM
When you turn down a lucrative deal because it doesn’t fit your vision or strategy, that’s not a missed opportunity.
That’s proof that you actually have a vision or strategy.
More like that:
That’s proof that you actually have a vision or strategy.
More like that:
Be optimistic when acting; almost everything will fail, so you can’t let that stop you from trying.
But be pessimistic when deciding what to act on; you have to face reality and select the best idea, not the first idea or your favorite idea.
But be pessimistic when deciding what to act on; you have to face reality and select the best idea, not the first idea or your favorite idea.
November 25, 2025 at 8:52 PM
Be optimistic when acting; almost everything will fail, so you can’t let that stop you from trying.
But be pessimistic when deciding what to act on; you have to face reality and select the best idea, not the first idea or your favorite idea.
But be pessimistic when deciding what to act on; you have to face reality and select the best idea, not the first idea or your favorite idea.
It’s working “smarter” 𝘢𝘯𝘥 “harder.”
Or at least, working “smart” (i.e. good strategy and prioritization) and “hard” (enough hours, and efficiently).
You probably already work hard; here’s how to work smarter.
Or at least, working “smart” (i.e. good strategy and prioritization) and “hard” (enough hours, and efficiently).
You probably already work hard; here’s how to work smarter.
Ruthless prioritization while the dog pees on the floor
Because time is zero-sum, prioritization is mandatory. This is an index of purpose-built prioritization frameworks, and an overarching one to optimize your life.
longform.asmartbear.com
November 25, 2025 at 6:57 PM
It’s working “smarter” 𝘢𝘯𝘥 “harder.”
Or at least, working “smart” (i.e. good strategy and prioritization) and “hard” (enough hours, and efficiently).
You probably already work hard; here’s how to work smarter.
Or at least, working “smart” (i.e. good strategy and prioritization) and “hard” (enough hours, and efficiently).
You probably already work hard; here’s how to work smarter.
Most angel investors don’t understand this:
It's not just about picking “the best,” it's about having access to the best companies in the first place.
Otherwise, even if you are the best at picking -- which you’re not -- it still doesn’t work out.
It's not just about picking “the best,” it's about having access to the best companies in the first place.
Otherwise, even if you are the best at picking -- which you’re not -- it still doesn’t work out.
November 24, 2025 at 10:06 PM
Most angel investors don’t understand this:
It's not just about picking “the best,” it's about having access to the best companies in the first place.
Otherwise, even if you are the best at picking -- which you’re not -- it still doesn’t work out.
It's not just about picking “the best,” it's about having access to the best companies in the first place.
Otherwise, even if you are the best at picking -- which you’re not -- it still doesn’t work out.
Startup success is the dream, but founders often find burnout occurs at the peak of their success.
Early rewards are worth the pain, but this can change.
Success doesn't always mean fulfillment.
Early rewards are worth the pain, but this can change.
Success doesn't always mean fulfillment.
Finding Fulfillment
What creates a fulfilling existence? Exploration leads to a framework I’ve used for years for myself and the people around me. I hope it helps you too.
longform.asmartbear.com
November 24, 2025 at 8:45 PM
Startup success is the dream, but founders often find burnout occurs at the peak of their success.
Early rewards are worth the pain, but this can change.
Success doesn't always mean fulfillment.
Early rewards are worth the pain, but this can change.
Success doesn't always mean fulfillment.
If you’re just like everyone else (in your self-selected bubble), it is comfortable.
It might be the best thing too.
Still, the right sort of discomfort comes from growing, stretching, trying new ideas.
You don’t have to keep the ones that don’t fit.
It might be the best thing too.
Still, the right sort of discomfort comes from growing, stretching, trying new ideas.
You don’t have to keep the ones that don’t fit.
November 24, 2025 at 8:45 PM
If you’re just like everyone else (in your self-selected bubble), it is comfortable.
It might be the best thing too.
Still, the right sort of discomfort comes from growing, stretching, trying new ideas.
You don’t have to keep the ones that don’t fit.
It might be the best thing too.
Still, the right sort of discomfort comes from growing, stretching, trying new ideas.
You don’t have to keep the ones that don’t fit.
A smart way to leverage social media is to sincerely ask for help and feedback.
A stupid way to waste time on social media is to ask generic questions you already know the answers to, for “engagement.”
A stupid way to waste time on social media is to ask generic questions you already know the answers to, for “engagement.”
November 24, 2025 at 2:11 PM
A smart way to leverage social media is to sincerely ask for help and feedback.
A stupid way to waste time on social media is to ask generic questions you already know the answers to, for “engagement.”
A stupid way to waste time on social media is to ask generic questions you already know the answers to, for “engagement.”
If your company is just like the competitors, customers will pick the competitors, because their brands are better-known, they rank higher in Google, they have more reviews, etc..
Yet another reason to be different.
Yet another reason to be different.
November 23, 2025 at 11:50 PM
If your company is just like the competitors, customers will pick the competitors, because their brands are better-known, they rank higher in Google, they have more reviews, etc..
Yet another reason to be different.
Yet another reason to be different.
Using a checklist to avoid silly, avoidable mistakes, is just good sense.
Being forced into a process that’s not aligned with work and happiness, is bad.
So “no process” isn’t the right sense. “Right process” is.
Being forced into a process that’s not aligned with work and happiness, is bad.
So “no process” isn’t the right sense. “Right process” is.
Individual efficiency vs administrative efficiency
When to prioritize individual autonomy, and when to standardize for global optimization.
longform.asmartbear.com
November 23, 2025 at 3:16 PM
Using a checklist to avoid silly, avoidable mistakes, is just good sense.
Being forced into a process that’s not aligned with work and happiness, is bad.
So “no process” isn’t the right sense. “Right process” is.
Being forced into a process that’s not aligned with work and happiness, is bad.
So “no process” isn’t the right sense. “Right process” is.
Extraordinary results probably require novel methods.
And “doing it my way” is one motivation to start a company.
So, founders like to throw away “best practices.”
Sometimes: That’s wonderful.
But sometimes it’s just worse, without benefit.
Be selective.
And “doing it my way” is one motivation to start a company.
So, founders like to throw away “best practices.”
Sometimes: That’s wonderful.
But sometimes it’s just worse, without benefit.
Be selective.
November 23, 2025 at 1:54 PM
Extraordinary results probably require novel methods.
And “doing it my way” is one motivation to start a company.
So, founders like to throw away “best practices.”
Sometimes: That’s wonderful.
But sometimes it’s just worse, without benefit.
Be selective.
And “doing it my way” is one motivation to start a company.
So, founders like to throw away “best practices.”
Sometimes: That’s wonderful.
But sometimes it’s just worse, without benefit.
Be selective.