The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 13 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Dunn: 90% of Chicago VC alpha and funding comes from the coasts
“90% of the alpha for Chicago-based venture firms is created on the coasts, right? And 90% of the capital that the leading Chicago companies raise is from the coasts.”
Dunn pitched 15 Chicago VCs and got rejected before Forerunner term sheet
“I did 15 pitches in Chicago, because I wanted to raise our Series A from a Chicago venture fund. I got 15 no's. I did one pitch on the West Coast with Kirsten Green from Forerunner, and we got a term sheet within 48 hours.”
Dunn predicts Pie will be the next great American social network
“Look, I think there's room for the next great American rooted social network right now. And I believe three things about it. Number one, it's going to be AI native. Number two, it's going to be focused on actual friends and your IRL local life. You're in real …”
Dunn: Local social apps need 1,000 users and 50 events per market
“We think you need about a thousand people on that people tab, about 50 events on the events tab, and that's when we start to see percolation and social density and geographic density start to get momentum.”
Dunn: Ecosystems need a $50B+ anchor company to create angel networks
“You gotta build a hundred billion dollar, or at least a fifty billion dollar company, To create that ecosystem of angels, and to create a training ground for the entrepreneurs of, you know, the next decade in Chicago.”
Dunn: Getting off phones requires using phones and top social influencers
“Because the only way to get off these phones is through our phones. The people that were influential in hooking us on social media are very well positioned to say, guys, let's get out.”
Pie halved its team from 23 to 12 due to AI efficiency
“Well, at one point the team was 23, and the age of AI it's now 12, and we've seen what you guys are talking about, which is just a massive collapse of product design, engineering, and even go to market, where people can do so much more, and so, you know, we di…”
Dunn: Chicago has never built a $100B enterprise value tech company
“We've never had a hundred billion dollar enterprise value tech company built here in Chicago.”
Dunn was hospitalized for bipolar disorder while Bonobos generated $100M+ revenue
“When we were nine years into building Bonobos, the cliff notes on my story were we had over a hundred million of revenue. We had 600 plus employees and I ended up in the psych ward of Bellevue because I had untreated and unmedicated bipolar type one.”
Andy Dunn: Pie launched Penelope AI agent to coordinate social lives
“We just launched an AI agent called Penelope and her job is both in iMessage as well as soon in the app to help be a, what we call a social life
Instigator.
You know, and chaos coordinator to get you together with the people that you should be spending more ti…”
Andy Dunn: Pie is live in three cities and expanding to five more
“That's live in Chicago, Austin, San Francisco. We're going live in New York and LA. We got other smaller markets percolating like Columbus and Milwaukee and Atlanta.”