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19.02.2026 12:11
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And how my biggest mistake wasn't failing, it was thinking that I couldn't.
🔗: chapin.io/talk-dangers...
I shared how early momentum made me stop asking hard questions.
How I mistook validation for inevitability.
How I started believing the version of the story that sounded best, at the expense of the truth.
Instead, earlier this month, I came back with a post-mortem, a story I've spent nearly five years trying to figure out.
When I launched my startup ten years ago, I imagined returning to the Bay for a victory lap.
I imagined I'd visit universities to talk about the brilliance of what we’d just executed - how we re-invented e-commerce.
The powers that be are running toward substance, deep knowledge, and credibility.
That's why Wikipedia is now king: hackernoon.com/wikipedia-ru...
It doesn't matter if you think the output is "good." We can tell.
It doesn't matter if your SEO chart is going up and to the right. Won't last.
Quit dicking around with AI-generated content.
If you're trying to build/manage/maintain an online reputation (whether for yourself or for a company), do not post anything that comes out of these AI platforms.
Internal linking is one of those simple SEO things that has a clear and tangible benefit.
But most WordPress plugins that help you manage internal links bury you in clutter and upsells.
So, meet Drew's Simple Internal Linking.
It's super-fast, super-easy, and free: chapin.io/drews-simple...
We're a week away from the next issue of my free entrepreneurship newsletter!
Here's a sneak preview: 👶🤓🤖✊💀🪩
Don't miss it: chapin.io#/portal/signup
And another thing!
If someone breaks Ken Jennings' Jeopardy streak, I think they should get Ken's hosting job. Automatically. No questions.
And if Ken wants that job back, he's gotta go earn it back.
Constant refreshes: aviators and ice cream and Amtrak for four years, then... that dance.
Opportunity to educate kids.
Opportunity for idiots to vote solely on who they want the mascot to be.
Fun.
Thank you for coming to my TED Talk.
I am sure Washington football fans like Tuddy the Pig, but the Commanders mascot needs to be the commander in chief.
A mascot with a term limit.
Hail to the Chief. Salutes. A mascot who has secret service and nuclear codes.
"AI is coming for coders but not (insert list of blue collar jobs)" is one of those takes that sounds interesting in this moment - but it will age like milk.
The startup world loves to talk about resilience and grit,
but it never talks about the ways pressure warps your thinking.
Many founders respond by moving into isolation,
which can be a dangerous place: chapin.io/talk-the-ris...
Programmatic SEO sucks.
But it can suck less - with the right tools and a little bit of effort.
Remember effort? hackernoon.com/ai-tools-can...
NextPick is a company rising at the right time as they've launched a three-sided marketplace (athletes/coaches/agents) to centralize it all and bring some order to the chaos: chapin.io/deal-memo-ne...
Between rising tuition costs and rising athlete compensation (via NIL), a seat on a college athletic roster is more valuable than ever before.
And coaches are struggling to keep up.
Rentaba brings modern fintech to the tenant-landlord relationship, including common-sense features that will help young renters, university students, and renters who are here from abroad.
I published a deal memo on the Philly-based company this month - check it out.
More: chapin.io/deal-memo-re...
Landlords determine a renter's credit worthiness based on a score that has nothing to do with their rental history - does that make sense?
Of course not.
Major press, pitch awards, incubators, corporate pilots, big meetings.
Nice. But it's all theater. Maybe "momentum" is a better way to say it.
But momentum is not a business: hackernoon.com/the-differen...
Wet floor sign... by Amazon Basics???
Is nothing sacred???
My landlord is taking Rich Dad, Poor Dad to the next level - now they make money while *I* sleep?
I like the cut of their jib.
I hope they make it.
You can provide direction like (sarcastically), (enthusiastically), or even (laughing) and (sobbing). HUGE leap for people doing bulk content creation with things like ads, etc.
More: hackernoon.com/text-to-voic...
The question with text-to-voice is no longer "does this sound human" - it's "how do you want this to feel?" There have been some improvements here that are really hard to believe.
Models like OpenAudio (accessible via fish.audio/studio/) now allow you to include intention, mood, and emotion.
You may not even realize that it's fundamentally rewiring the web: hackernoon.com/the-new-tool...
Platforms like Quaily, Ghost, and HeyGen can take a single blog post to more formats (audio, video) than before, in more languages than ever before, on more platforms than ever before (blog, email, messaging???). In just a few minutes.
A whole team has been shrunk to a few AI subscriptions.
I decided to write more this year.
Tech business writing is something I've swung in and out of the last decade.
And it had been a few years.
Here's what I didn't count on when I decided to dial back in this year: publishing isn't just about the blog post anymore.
Been in the mood to write, I guess.