Jason Cohen started a blog, then TWO unicorn companies (WPengine + Smart Bear)

I sat down with a guy named Jason Cohen who is the founder of TWO different unicorn companies: WPengine and SmartBear.

It's hard enough to start a billion dollar company but he's done it twice...and much of the early success stemmed from his blog!

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Jason is what I endearingly call a "Post-Economic Nerd" which is one of my favorite people...because even with wild success and no need to work, they remain curious, creative, active still code or go down rabbit holes of curiosity.

​Watch or listen to the entire interview here -->​

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My notes from the interview:

• 0:00:00 Intro: Jason started two unicorn companies.
• 0:00:11 What is Smart Bear?
• 0:00:53 What is WPengine? Largest managed Wordpress host in the world.
• 43% of the web builds on Wordpress
• 0:01:42 How did you know you could charge 10x or 20x more than the competitors.
• He had the problem so he fixed it for himself, but most of the time that’s not really a business.
• To make a company out of a problem you have, it must be cost effective enough.
• 0:03:35 He did 50 customer interviews and 5 months later, he found out people would pay 10x more for a Wordpress host if it was fast, scaleable, secure, and have engineer-level tech support.
• 0:05:15 I’ve personally used Wordpress for 15+ years, and every few years I’d get hacked until I moved to WPengine then it stopped.
• 0:06:11 When a company is small if you call their “support line” you’ll likely get an engineer or the founder themselves….it’s a huge advantage for small companies over bigger companies with bigger support teams.
• 0:07:47 “Inciting Moments” or “Inciting Events” = When someone gets hacked all of a sudden they really want a more secure website….but maybe it takes them several times of getting hacked before moving.
• 0:09:35 They found their biggest allies in getting people to signup was SEO people. Their recommendations caused people to take action. Those were the keywords and niches they first went after.
• 0:10:23 It’s like selling burglar alarms, you don’t need one
• 0:11:19 “It’s fun to put your most important number on the wall and say we’re going after that.”
• 0:13:35 I like optimization. “Here I am in a great market doing something I love.” That’s a good place to start as an entrepreneur. What are my assets, talents, experience sets, and what in combination is unique, what do I love doing so much you wouldn’t have to pay me? Now figure what in there an actually be a business (not all of it).
• 0:16:04 It was easy to go after the Wordpress market because even at the time it was 11% of the internet which is just soooo big and still growing. Large and growing markets are great because there’s always niches to service within that.
• 0:18:43 How do you come up with business ideas? Do you write a bunch down? “I don’t build too many 1st products, but we build a lot 2nd and 3rd additional products to our main product.”
• 0:23:04 Talking to customers is the only way to figure out the right product. “If you can’t get them on the phone now, how will you get them on the phone ever?” You can be creative and use platforms like LinkedIn to reach out. “I’m building a startup that’s supposed to be for people like you. I know your time is valuable, so I’m happy to pay even more than your normal hourly rate to get your feedback. 40 out of 50 people agreed, and only one person charged him.
• 0:24:52 It’s hard to go look for a problem, you generally stumble upon it. So the answer is exposing yourself to stuff. Then try to validate. Doing something like McKinsey Consulting will exposure you to all sorts of businesses and industries.
• 0:27:11 Talking about Wordpress.
• 0:31:30 Forums → FB Groups → Private Communities
• 0:03:30 What platforms do you use? Twitter, LinkedIn, Threads…standard stuff. I post the same thing everywhere. I don’t primarily do social media but I write longform that’s unique to me. That’s where I want to spend most of my time. I have hundreds of drafts.
• 0:35:33 How did you get your first WPengine clients. “I had 18,000 RSS feed subscribers, I launched it, and only 2 people signed up.” You have to muscle your first customers in.
• 0:37:20 Why did you first start writing online? “Started the blog for Smart Bear and wanted to be the voice of the company like the 37 Signals blog, but no one wrote on it but me.” It became the largest driver of traffic to the corporate site.
• 0:38:39 Personal Brands vs Corporate Brand? Write under your own name or company name? There’s a macro-trend of younger people not having personal secrets as much. If the goal is to sell the company you have to have a corporate blog.
• 0:43:44 Using AI? Using mainly for coding and it’s so good it’s frightening.
• 0:44:14 Writing for me is personal expression, trying to hone my craft, and my own ideas which are new. Using AI to write that is completely counter to that. I sometimes use it as a super-thesaurus or to generate social content angles from a longer article.
• 0:46:46 Are you afraid of where AI is going? “I’m afraid of it’s impact on everyone. I think longrun its net impact will likely be good, but it might happen to quickly.” The speed at which it happens is the issue, not that things change. In the 80’s people thought robots would take their jobs, but what happened was the jobs moved to other countries. This time instead of blue collar it’s the writers and accountants and such. It’s frightening how fast and uncertain things are and nobody has a comprehensive answer.
• 0:49:37 Are things moving faster and changing…or are we just old?
• 0:54:45 What skills are you teaching your children to future proof them for AI? “Kids are better than this stuff already. THEY are going to be deciding what skills will be important, not us.”
• 0:55:35 The most popular Wordpress trend? Block based themes. You’ll be able to drag and drop everything.
• 0:56:49 How would you go about starting a new business? Take what I currently know about and see where I could solve a problem and need.
• 0:57:37 Are there any marketing hacks you tried that worked or flopped? Going to events did a lot better than we thought…you don’t even need a booth. You can walk around with a logo backpack and talk to 100 people.
• 0:59:48 A book that’s changed your life? Good Strategy Bad Strategy by Richard Rumelt
• 1:13:33 Being around people with extreme levels of wealth, where do people get the most fulfillment? Internal fulfillment, some have external purposes like religion or other causes. Teaching gives you some ego plus feels like you’re paying it back.
• 1:16:47 Generally many very rich are not happy, not fulfilled, and don’t have a good family life. Leaving a company often leaves you directionless. “Life After Exit.”
• 1:18:35 The Seinfeld story after the end of the show, Seinfeld was a hardcore road comic, and that saved him.

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SHORT CLIP: People pay more when something matters to them and they know it will work

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SHORT CLIP: It's not enough for your strategy to be good, you have to know how to execute it well.

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SHORT CLIP: As an entrepreneur, how can you be sure that what you're doing is really what you want?

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SHORT CLIP: Begin by targeting a small niche and gradually work your way towards expansion

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I hope you enjoyed this interview! Watch it here
​Sincerely,
Neville Medhora

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