Smash Your WooCommerce Hosting Problems... so you can do more important smashing. Girl dad, husband, nerd. Swears well with others.
Michigan, USA
Joined September 2017
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"Having said that, when the founders decide to do this, you have just got to get with the program. It is not your company.”
One of his best takes in the last six months.
Who is right and who is wrong: Day One or Valar?
“Everyone was saying that Day One was suing their portfolio company, which was completely wrong. It is Valar that wants declaratory judgment to move on.
Sequoia came in very aggressively, and everyone had to waive their pro rata so that they could get their ownership target. Then Valar let one of their investors invest because they are strategic.
This is the whole point: you are not supposed to play favourites. Having said that, when the founders decide to do this, you have just got to get with the programme. It is not your company.” @jasonlk
Love to hear your thoughts @shaunmmaguire @ChrisHarveyEsq @immad @JayKapoor
In the age of AI absolutely everything is possible... except for sleeping well at night.
For that you still need human beings who take responsibility for your shit and lose sleep on your behalf.
Liftoff 🚀
Unbelievably happy for you @ben_gabler !!!
Can't wait to see you in Miami.
After six years of building Rocket and coming off the one-year anniversary with hosting .com, my time at the company has come to an end.
When we launched Rocket in 2020, we bet on an edge-first approach to WordPress, with CDN and WAF in front of every site by default. That was unusual then and a major contributor to Rocket being named the 167th-fastest-growing company in 2025 on the Inc5000. Today, it's the standard across managed WordPress hosting, and I'm proud of the role Rocket played in pushing the industry in that direction.
Thank you to the team who built it with me and to the customers who trusted us with their business. As a substantial shareholder, I wish everyone at Rocket and hosting .com continued success with their mission in the web hosting space.
Thank you as well to the WordPress and hosting community. The relationships I've built here are the best part of the last six years, and they aren't going anywhere.
To be clear about what this is: I'm not retiring, and I'm not riding off into the sunset after an exit. The tech and investment community in Palm Beach County and South Florida is growing faster than ever, and I couldn’t be more excited for what the future holds in my own backyard.
I've been through the full arc of starting, scaling, and selling a company many times. I learned a lot from these experiences, and I have more energy, experience, and drive to help shape the future than I've ever had.
AI has changed what a small team can build and how quickly solutions can get to market, enabling small businesses to do far more than just think about web hosting and WordPress.
That's where my attention is going next. If you’re building something great, particularly in the AI space, let’s talk.
I clearly indicated that I wanted our spots to be flipped but the model can't help but make me a foot taller than @ben_gabler 😂
If you've ever wondered why your unlimited workers infinite scale horizontal managed WordPress thing never seems to actually work... it's because it's a literal cluster f@cK and it only "works" for sites that don't need it to work.
AKA: It doesn't work.
I think that Microsoft is actually really onto something with how shitty CoPilot is compared to literally everything else:
IT doesn’t want anyone to know how shitty they are at their jobs.
So everyone at corporate gets a harness so retarded the models don’t matter.
Imagine...
You're worth hundreds of billions of dollars and someone asks what what you would tell your younger self.
And with a straight face and a 1000-yard stare you tell yourself: DON'T DO IT!
Welp, back to work. How hard can it be? 🫠
If you buy a Main cabin seat on Delta airlines now you don’t actually get to pick your seat.
It’s randomly assigned, later.
But if you upgrade to Main Classic you can pick a seat, but you’ll pay more than Comfort Plus.
So you bump up to Comfort Plus… but you can’t pick your seat there either.
Because now it’s just Comfort, no plus. And you chose Comfort Basic, you idiot.
If you wanna pick your seat in the rows right behind First you now need Comfort Classic.
Which is almost as expensive as…
You get the idea.
I get that you wanna extract maximum rents and that using human psychology against customers is one (albeit disgusting) way to do so but this is fucking hella lame.
I have young children. I’m pretty sure that everyone involved, passengers and staff included, would like children to NOT be separated from their parents.
Especially not when we’ve already upgraded twice.
This should be made crystal clear on every single checkout page.
Especially after I have to select their ages from your stupid drop down on EVERY single checkout.
Thankfully (for your shareholders) you have hundreds of billions of dollars worth of “moat” in the form of airplanes that occasionally fall apart mid flight.
This shit is gross.
Millions and millions of miles/dollars later I don’t even know if I’m sitting next to my daughter.
Can’t wait for the change fee I’ll have to pay just to change from fully fucked and clueless to “We appreciate your loyalty Mr. Gallagher.”
The only silver lining here is that Delta is a dinosaur through and through.
The asteroid can’t get here fast enough.
It's that special time of the year in Michigan where it dips below 60 degrees and suddenly you're sourcing fire wood and looking for your fleece lined pants 🫠
You either die a hero or live long enough to see yourself become the... person who sees that your heroes are twats.
My business wouldn't exist if not for his Quora so I'll never shit on this dude publicly.
Other than now obviously 😂
What do you do when some snooty asshole at a doctors office requires a fax before they can do the blood draw your 10yo is dreading for days... 🤷♂️ Use Dropbox Fax by @DropboxSign to send and receive faxes from anywhere. #DropboxFax app.fax.dropbox.com
Daybreak (GPT 5.6 Cyber) deep fried my entire 5 hour allocation in less than five minutes.
But it finished the job behind the scenes (8 minutes 34 seconds total) and it found a medium severity CVE inside a plugin with millions of installs.
The accelerated projection is more than one million sites, every single day. Possible, sure. But have you met people?
9/10 people told by doctors that they're gonna die if they don't quit smoking/drinking/sticking their dick in a toaster... choose death over change.
Did some modeling... What's the most likely future?
WordPress as a share of all websites, starting from 40.7% today.
The number that actually matters is not the decline, it's the acceleration.
History:
- Jan 2025: 43.6% (the all-time peak)
- Apr 2025: 43.5%
- Jul 2025: 43.4%
- Oct 2025: 43.3%
- Jan 2026: 43.0%
- Apr 2026: 42.5%
- Jul 2026: 41.5%
- Sept 2026: 40.7%
Future #1:
If the rate holds at the current 1.2 points a quarter:
- Dec 2026: 39.5
- Mar 2027: 38.3
- Jun 2027: 37.1
- Sep 2027: 35.9
- Dec 2027: 34.7
- Mar 2028: 33.5
- Jun 2028: 32.3
- Sep 2028: 31.1
Future #2:
If the acceleration continues at the rate it has for four straight quarters (each quarter losing about 0.35 more than the last):
- Dec 2026: 39.2
- Mar 2027: 37.3
- Jun 2027: 35.0
- Sep 2027: 32.4
- Dec 2027: 29.5
- Mar 2028: 26.2
- Jun 2028: 22.5
- Sep 2028: 18.5
Not with a bang but with a whimper…
At a town hall meeting in rural Nebraska.
Well said and well written. Full agreement.
Hung out with a friend who builds data centers today.
Notes:
- They're offering 400-home towns with $1.2m annual budgets $30m/year for 40 years.....and getting turned down.
- Reasons: 2-3 of the 5-6 person town council have local businesses and are worried they'll be scorned locally if they vote yes
- There's a loud 20% that's anti turning down a 60% who are big thumbs up on it but don't want to publicly fight.
- He travels with security and receives death threats weekly
- Energy is not the immediate top problem, it's entitlements.
- They're having the construction GC bring all their subcontractors to town mtg's to show the job impact
- Unions in MI and other places are defunding Dems bc they're anti-jobs now. He got emailed this while we were hanging.
All of this actually, strangely, gives me hope. Because it's so feverishly dumb for local towns to turn these down that the dam will break.
But, meanwhile, China is on its way to basically limitless electricity. AI supremacy might be for all the marbles. We must accelerate.