Drew Chapin, Startup Guy

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.

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.

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...

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.

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...

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.

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...

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.

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.

Deal Memo: Rentaba, "Credit Where Rent Is Due" Rentaba is reworking the tenant-landlord relationship by bridging the rental market and modern financial technology.

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...

Deal Memo: Rentaba, "Credit Where Rent Is Due" Rentaba is reworking the tenant-landlord relationship by bridging the rental market and modern financial technology.

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.

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.

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.

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.

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...

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.

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.

The New Tools Rewriting the Web | HackerNoon Publishing in 2025 isn’t just about writing, it’s about building a publishing system.

You may not even realize that it's fundamentally rewiring the web: hackernoon.com/the-new-tool...

The New Tools Rewriting the Web | HackerNoon Publishing in 2025 isn’t just about writing, it’s about building a publishing system.

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.

The New Tools Rewriting the Web | HackerNoon Publishing in 2025 isn’t just about writing, it’s about building a publishing system.

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.

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.

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-...

The OpenAI device can't be a pendant.
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

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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. 😎

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.

These small compromises can, in time, result in catastrophic outcomes.

Believe me on that one.

This was the subject of my talk at ACFE Pittsburgh's annual meeting this week: chapin.io/talk-the-fou...

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.

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.

Deal Memo: Burble Wellness An AI-powered app delivering personalized hypnosis and subconscious therapy audio sessions, tailored to your needs for sleep, anxiety, and stress relief.

The deal memo is live here - and if you're interested in catching the next one, make sure you sign up for my newsletter by tapping Subscribe in the header/footer: chapin.io/burble-ai-hy...

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.

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?

I'm doing some research about banking (and specifically, de-banking). 🏦
If you or someone you know is working on solutions in this area, please reach out: debanking@chapin.io. 🙏