Drew Chapin, Startup Guy
@chapin.io
Recovering tech founder building a digital discoverability agency at discoverability.co. Angel Squad @hustlefund.bsky.social. Red Sox fan. More: chapin.io
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.
I imagined I'd visit universities to talk about the brilliance of what we’d just executed - how we re-invented e-commerce.
Talk: "The Dangers of Over-Confidence" at Berkeley Haas
A key driver of startup failure is unchecked belief. Chapin unpacks how confidence became hubris his startup story.
chapin.io
October 27, 2025 at 11:11 AM
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.
I imagined I'd visit universities to talk about the brilliance of what we’d just executed - how we re-invented e-commerce.
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.
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.
Wikipedia Rules Everything Around Me | HackerNoon
Wikipedia is the internet’s true power broker and the backbone of AI. Here’s why it defines your digital reputation, and how not to be left behind.
hackernoon.com
September 1, 2025 at 11:11 AM
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.
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...
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...
Drew's Simple Internal Linking WordPress Plugin
A plugin to add internal links to your WordPress site. Instantly convert anchor text to links sitewide, free, fast, and easy. Available now.
chapin.io
August 21, 2025 at 11:11 AM
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...
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
Here's a sneak preview: 👶🤓🤖✊💀🪩
Don't miss it: chapin.io#/portal/signup
Drew Chapin, Startup Guy
Drew Chapin is a Philadelphia-based go-to-market specialist who has had a 360-degree experience in early-stage entrepreneurship.
chapin.io
August 19, 2025 at 11:11 AM
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
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.
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.
July 24, 2025 at 11:07 PM
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.
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.
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.
A mascot with a term limit.
Hail to the Chief. Salutes. A mascot who has secret service and nuclear codes.
July 21, 2025 at 10:28 PM
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.
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.
July 21, 2025 at 11:11 AM
"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...
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...
Talk: "The Risks of Founder Isolation" at ACFE New Jersey
Entrepreneurship can be a mental health minefield with catastrophic consequences. One key element: founder isolation.
chapin.io
July 8, 2025 at 9:32 PM
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...
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...
But it can suck less - with the right tools and a little bit of effort.
Remember effort? hackernoon.com/ai-tools-can...
AI Tools Can Now Write Like You—Here’s How That Changes Everything | HackerNoon
New MCP tools enable programmatic SEO that’s actually useful, combining context and your knowledge base to create scalable, high-quality content.
hackernoon.com
June 26, 2025 at 11:11 AM
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...
But it can suck less - with the right tools and a little bit of effort.
Remember effort? hackernoon.com/ai-tools-can...
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.
And coaches are struggling to keep up.
Deal Memo: NextPick, Fixing College Athletic Recruiting
NextPick offers the college athletic recruiting process a modern three-sided marketplace that connects parents of athletes, vetted recruiting agents, and college coaches.
chapin.io
June 24, 2025 at 11:11 AM
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.
And coaches are struggling to keep up.
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.
Of course not.
Deal Memo: Rentaba, "Credit Where Rent Is Due"
Rentaba is reworking the tenant-landlord relationship by bridging the rental market and modern financial technology.
chapin.io
June 23, 2025 at 11:11 AM
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.
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...
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...
The Difference Between Early-Stage Theater and Traction | HackerNoon
A former founder reflects on how fake traction and startup delusion led to his downfall - and what real traction actually looks like.
hackernoon.com
June 19, 2025 at 11:11 AM
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...
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???
Is nothing sacred???
June 17, 2025 at 11:11 AM
Wet floor sign... by Amazon Basics???
Is nothing sacred???
Is nothing sacred???
My landlord is taking Rich Dad, Poor Dad to the next level - now they make money while *I* sleep?
June 16, 2025 at 11:11 AM
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.
I hope they make it.
June 12, 2025 at 11:15 AM
I like the cut of their jib.
I hope they make it.
I hope they make it.
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.
Models like OpenAudio (accessible via fish.audio/studio/) now allow you to include intention, mood, and emotion.
Text-to-Voice? No, It’s Something More: Text-to-Emotion. | HackerNoon
How a new wave of AI voice models are turning text into emotionally rich, real-time performances. This is the future of voice: programmable and persuasive.
hackernoon.com
June 10, 2025 at 11:11 AM
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.
Models like OpenAudio (accessible via fish.audio/studio/) now allow you to include intention, mood, and emotion.
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.
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.
The New Tools Rewriting the Web | HackerNoon
Publishing in 2025 isn’t just about writing, it’s about building a publishing system.
hackernoon.com
June 9, 2025 at 11:11 AM
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.
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.
June 6, 2025 at 11:11 AM
Been in the mood to write, I guess.
It feels noble to pour everything into your startup.
You want to be the obsessed founder,
outworking everyone,
burning the midnight oil.
Early, that founder-company fusion can be a real edge.
But we rarely talk about how that can become a real blind spot: hackernoon.com/you-are-not-...
You want to be the obsessed founder,
outworking everyone,
burning the midnight oil.
Early, that founder-company fusion can be a real edge.
But we rarely talk about how that can become a real blind spot: hackernoon.com/you-are-not-...
You Are Not Your Company - Your Company is Not You | HackerNoon
About the psychological trap founders fall into, merging their identity with their startup, and why maintaining objectivity is essential.
hackernoon.com
June 5, 2025 at 11:11 AM
It feels noble to pour everything into your startup.
You want to be the obsessed founder,
outworking everyone,
burning the midnight oil.
Early, that founder-company fusion can be a real edge.
But we rarely talk about how that can become a real blind spot: hackernoon.com/you-are-not-...
You want to be the obsessed founder,
outworking everyone,
burning the midnight oil.
Early, that founder-company fusion can be a real edge.
But we rarely talk about how that can become a real blind spot: hackernoon.com/you-are-not-...
The OpenAI device can't be a pendant.
Jony Ive is better than that.
Jony Ive is better than that.
June 2, 2025 at 11:11 AM
The OpenAI device can't be a pendant.
Jony Ive is better than that.
Jony Ive is better than that.
On deck: something totally new. ⚡️
If you want to hear what we're cooking up, sign up for my monthly newsletter: chapin.io#/portal/signup
If you want to hear what we're cooking up, sign up for my monthly newsletter: chapin.io#/portal/signup
May 29, 2025 at 11:11 AM
On deck: something totally new. ⚡️
If you want to hear what we're cooking up, sign up for my monthly newsletter: chapin.io#/portal/signup
If you want to hear what we're cooking up, sign up for my monthly newsletter: chapin.io#/portal/signup
Wordle 1,439 1/6
🟩🟩🟩🟩🟩
I'd like to thank opposites, climate change discourse, that seltzer, the bears, that Tom Hanks movie, Coca Cola, and, obviously, the WooSox.
Feels good. 😎
🟩🟩🟩🟩🟩
I'd like to thank opposites, climate change discourse, that seltzer, the bears, that Tom Hanks movie, Coca Cola, and, obviously, the WooSox.
Feels good. 😎
May 28, 2025 at 11:44 AM
Wordle 1,439 1/6
🟩🟩🟩🟩🟩
I'd like to thank opposites, climate change discourse, that seltzer, the bears, that Tom Hanks movie, Coca Cola, and, obviously, the WooSox.
Feels good. 😎
🟩🟩🟩🟩🟩
I'd like to thank opposites, climate change discourse, that seltzer, the bears, that Tom Hanks movie, Coca Cola, and, obviously, the WooSox.
Feels good. 😎
In the startup world, people love to call it “founder-friendly.”
But really, it’s "no questions asked."
The result is a culture of deference and founder isolation which becomes the perfect breeding ground for ethical fading, dangerous self-talk, and poor choices.
But really, it’s "no questions asked."
The result is a culture of deference and founder isolation which becomes the perfect breeding ground for ethical fading, dangerous self-talk, and poor choices.
Talk: "The Founder-Friendly Trap" at ACFE Pittsburgh
Exploring how “founder-friendly” partners, isolation, and a lack of organizational controls can set the stage for disaster - and what we can all do to prevent it.
chapin.io
May 26, 2025 at 11:11 AM
In the startup world, people love to call it “founder-friendly.”
But really, it’s "no questions asked."
The result is a culture of deference and founder isolation which becomes the perfect breeding ground for ethical fading, dangerous self-talk, and poor choices.
But really, it’s "no questions asked."
The result is a culture of deference and founder isolation which becomes the perfect breeding ground for ethical fading, dangerous self-talk, and poor choices.
I've updated my May deal memo to include the Hustle Fund's deal assessment framework.
These are the essential questions they use to score opportunities - and now I'll include them at the bottom of every deal memo I share.
These are the essential questions they use to score opportunities - and now I'll include them at the bottom of every deal memo I share.
May 19, 2025 at 6:55 PM
I've updated my May deal memo to include the Hustle Fund's deal assessment framework.
These are the essential questions they use to score opportunities - and now I'll include them at the bottom of every deal memo I share.
These are the essential questions they use to score opportunities - and now I'll include them at the bottom of every deal memo I share.
Anyone else feel like this has nothing to do with your network connection and everything to do with the fact that ChatGPT just doesn't feel like doing what you asked?
May 15, 2025 at 2:05 PM
Anyone else feel like this has nothing to do with your network connection and everything to do with the fact that ChatGPT just doesn't feel like doing what you asked?