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Jason Cohen

Jason Cohen

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Founder (WP Engine, SmartBear); essays and tactics on bootstrapping, product strategy, and founder psychology.

Recent Posts

You Can only Juggle Two of Three Priorities
Social•Feb 21, 2026

You Can only Juggle Two of Three Priorities

Can you have a full-time job, and devote the time necessary to build a startup, and spend quality time with family every day? At least one of those things will suffer. You can have two Big Things but not three. https://t.co/uCnzbXtN3G

By Jason Cohen
Create Boss‑focused Reports During Trial to Close Deals
Social•Feb 20, 2026

Create Boss‑focused Reports During Trial to Close Deals

You make software for person P. They have a boss Q. Or better, their C_O. If Q wants your product, P gets to buy it. So, can you make a report or daily/weekly email or etc. that Q wants? Do it during the trial,...

By Jason Cohen
Ship Fast to Keep Iteration Speed High
Social•Feb 20, 2026

Ship Fast to Keep Iteration Speed High

A reason to ship in 1 month instead of 6 is to incorporate feedback. Another is that a 6-month codebase will be a lot hard to to change than a 1-month. You could even still start from scratch. At the beginning, anything...

By Jason Cohen
Bootstrappers Must Charge $30‑$80 for Sustainable Growth
Social•Feb 20, 2026

Bootstrappers Must Charge $30‑$80 for Sustainable Growth

Bootstrappers need to have prices like $30/mo-$80/mo, not like $10/mo. It’s not harder to get customers (see how many times someone raises prices and # cust/day doesn’t change), but you have no money for anything - no marketing, no engineering, no...

By Jason Cohen
Context Determines Whether Solo or Co‑Founding Wins
Social•Feb 19, 2026

Context Determines Whether Solo or Co‑Founding Wins

It is better to be single or attached? Well, do you mean in a toxic relationship or a loving supportive one? Context always matters. Now do this one: Is it better to be a single founder or a co-founder?

By Jason Cohen
Authenticity Wins: People Prefer Doing Business With Those They Like
Social•Feb 18, 2026

Authenticity Wins: People Prefer Doing Business With Those They Like

Many (most?) people pick up on insincerity. Many (most?) people like to do business with people they like. So…

By Jason Cohen
Ads Work; Doubting Them Reveals a Skill Gap
Social•Feb 18, 2026

Ads Work; Doubting Them Reveals a Skill Gap

So many people say “ads don’t work; write content.” All of my companies for 22 years grew with ads 𝘧𝘪𝘳𝘴𝘵 and forever. Ads won't be effective for 𝘢𝘭𝘭 companies, but "I've never seen it work" is an admission of lack of...

By Jason Cohen
Prioritize Marketing and Sales Over Endless Feature Tweaking
Social•Feb 18, 2026

Prioritize Marketing and Sales Over Endless Feature Tweaking

You will naturally spend more time making features and tweaking design rather than marketing, sales, and facing the difficult truths about why customers are cancelling. That’s why you need special effort on those areas. The full roadmap: https://t.co/slGN2Hmjwb

By Jason Cohen
Ask Yourself Hard Questions, Then Answer Them Confidently
Social•Feb 18, 2026

Ask Yourself Hard Questions, Then Answer Them Confidently

I left those meetings angry at first, but then embarrassed that I didn’t have better answers, and then motivated to get the right answers. So I started writing my own rude Q&A: • Why do I even exist when the market already...

By Jason Cohen
Anticipate Investor Attacks with a Rude Q&A
Social•Feb 17, 2026

Anticipate Investor Attacks with a Rude Q&A

When I started WP Engine, I thought I was pretty good at pitching. I had sold millions of dollars of software at Smart Bear, and I’d helped other companies with their pitches and fundraising. But of course it’s different when someone...

By Jason Cohen
Prioritize Bold, Visible Marketing Levers Over Subtle Nudges
Social•Feb 17, 2026

Prioritize Bold, Visible Marketing Levers Over Subtle Nudges

Instead of chasing subtle subliminal effects that get wiped away by ambient noise, we should focus on big, non-subliminal impacts in marketing. Like the home page, pricing, positioning, promises, competitive dynamics, and customer segmentation. https://t.co/KUXMFIswTZ

By Jason Cohen
When CEOs Outshine Teams, Hiring Is Failing
Social•Feb 16, 2026

When CEOs Outshine Teams, Hiring Is Failing

Early on, the CEO is “the best person at the company” at some things. Often sales (passion + knowledge) or product vision. But by 100 people, if the CEO is “better than everyone” at 𝘢𝘯𝘺𝘵𝘩𝘪𝘯𝘨, the CEO has hired poorly, and...

By Jason Cohen
Adjust ROI: Account for Estimation Errors in Task Prioritization
Social•Feb 16, 2026

Adjust ROI: Account for Estimation Errors in Task Prioritization

ROI is a good way to prioritize mid-sized tasks, but estimation errors (both in duration and in impact) can change the ROI by 2x-5x, so you need a system that understands that and causes you to select the right tasks...

By Jason Cohen
True Pivots Build on Commitment, Not Constant Overhauls
Social•Feb 16, 2026

True Pivots Build on Commitment, Not Constant Overhauls

If you're constantly changing the product, that's not “pivoting.” It's probably good. If you're constantly changing the entire company, that's not pivoting either, that's different companies. Pivot is committed to 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨, and then pivoting around 𝘵𝘩𝘢𝘵.

By Jason Cohen
Know Your Scale: One‑person? Plan Your Exit
Social•Feb 15, 2026

Know Your Scale: One‑person? Plan Your Exit

Are you a "0-1" person or a "2-50" person or a "100-5000" person? Often we don’t know until we’re already in the thick of it. You think you know, only because there’s comfort in the familiar. But maybe you really are just...

By Jason Cohen

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