Drew Chapin, Startup Guy
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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
Wet floor sign... by Amazon Basics???

Is nothing sacred???
June 17, 2025 at 11:11 AM
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
I like the cut of their jib.
I hope they make it.
June 12, 2025 at 11:15 AM
Been in the mood to write, I guess.
June 6, 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
May 29, 2025 at 11:11 AM
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.
May 19, 2025 at 6:55 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?
May 15, 2025 at 2:05 PM
Nothing like a pitch day to get me to a new city for the first time.

And my intro to Wilmington could not have been any better - congrats to Darren and the team at gener8tor Bronze Valley on a strong cohort!

Looking forward to watching this batch of startups run -🏃‍♂️💨
March 10, 2025 at 3:48 PM
When Philly's Founder Fridays is in the building, you drop everything and go.

This was where we selected Philly's submission to Jason Calacanis' Pitch Madness, a bracket startup tournament.

And I KNOW our selection is going to go full Saquon (which is to say, run over everybody). 💪
March 10, 2025 at 3:47 PM
Man, was THIS a fun night in Philly... never been in the building for a comeback like that. 🍀🏀
February 3, 2025 at 6:55 PM
👋
January 27, 2025 at 4:50 AM
This minivan dad just tryna beat you to
the joke
January 25, 2025 at 9:59 PM
so are we just doing this on every video call until the end of time, or... ?
January 16, 2025 at 8:09 PM
Feels like Nintendo's NYC store is featuring Luigi a liiiiiittle more than usual this week 🤔
December 12, 2024 at 9:57 PM