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
And how my biggest mistake wasn't failing, it was thinking that I couldn't.
🔗: chapin.io/talk-dangers...
🔗: chapin.io/talk-dangers...
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
And how my biggest mistake wasn't failing, it was thinking that I couldn't.
🔗: chapin.io/talk-dangers...
🔗: 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.
How I mistook validation for inevitability.
How I started believing the version of the story that sounded best, at the expense of the truth.
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
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.
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.
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
Instead, earlier this month, I came back with a post-mortem, a story I've spent nearly five years trying to figure out.
The powers that be are running toward substance, deep knowledge, and credibility.
That's why Wikipedia is now king: hackernoon.com/wikipedia-ru...
That's why Wikipedia is now king: hackernoon.com/wikipedia-ru...
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
The powers that be are running toward substance, deep knowledge, and credibility.
That's why Wikipedia is now king: hackernoon.com/wikipedia-ru...
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.
It doesn't matter if your SEO chart is going up and to the right. Won't last.
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
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.
It doesn't matter if your SEO chart is going up and to the right. Won't last.
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.
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.
July 21, 2025 at 10:28 PM
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.
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.
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.
chapin.io
June 24, 2025 at 11:11 AM
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...
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...
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.
chapin.io
June 23, 2025 at 11:11 AM
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...
I published a deal memo on the Philly-based company this month - check it out.
More: chapin.io/deal-memo-re...
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...
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.
hackernoon.com
June 10, 2025 at 11:11 AM
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...
More: hackernoon.com/text-to-voic...