Chicago

4 statements across 4 episodes · 3 bullish · 1 bearish · 4 people on the record · first statement Aug 17, 2015 by Ezra Galston · said 94 times in 59 episodes since 2015 · across every show →

Mentions by year

brought up most by Ezra Galston (7), Scott Dorsey (5), Steven Galanis (4), Peter Rahal (4), Harry Stebbings (4), Arteen Arabshahi (4), Jason Fried (3), Daniel Khachab (3)

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0510201520162017201820192020202120222023202420252026episodes it came up in
0025410201520162017201820192020202120222023202420252026episodesmentions per episode
2026 3 mentions in 3 episodes 1 per episode
2025 12 mentions in 9 episodes 1 per episode
2024 11 mentions in 7 episodes 2 per episode
2023 9 mentions in 6 episodes 2 per episode
2022 6 mentions in 4 episodes 2 per episode
2021 6 mentions in 5 episodes 1 per episode
2020 3 mentions in 3 episodes 1 per episode
2019 10 mentions in 6 episodes 2 per episode
2018 3 mentions in 3 episodes 1 per episode
2017 6 mentions in 4 episodes 2 per episode
2016 9 mentions in 4 episodes 2 per episode
2015 16 mentions in 5 episodes 3 per episode

every mention, scene by scene, with the transcript →

Everything said about Chicago, oldest first

Aug 17, 2015 positive
Assertion Not checkable as stated
Galston: Chicago is Uber and Instacart's second or third largest market
“If you ask Uber or Instacart, what, you know, their second or third most important market is, it's almost inevitably Chicago.”
Ezra Galston Aug 17, 2015 ▶ 8:15 20 VC 063: What It Takes To Standout In A Crowded Market with Ezra Galston @ Chicago Ventures
Sep 16, 2021 bullish
Prediction Held up
Salur: Getir will launch in NY, Chicago, and Boston by late 2021
“We start with three cities. Those are going to be New York, Chicago, and Boston. Before the end of the year, we'll be operational in all three, and then we'll take it from there.”
Nazim Salur Sep 16, 2021 ▶ 28:37 20VC: Getir Founder, Nazim Salur on The Future of Last Mile Convenience, Who Will Win? Lessons on Driver Acquisition and Efficiency, Zone Maturity and Time To Profitability and Scaling to 300 Cities in the US in 2022
Nov 2, 2022 positive
Assertion Not checkable as stated
Ilishayev: All existing mature GoPuff metro markets generate positive cash flow
“If you look at like on a metro basis, all of our existing metros are producing, you know, cash flow. So you have your call calling your cash cows, right? Philadelphia, Chicago's Boston's, Miami's all of our Texas markets of the world that are producing cash fl…”
Rafael Ilishayev Nov 2, 2022 ▶ 10:55 GoPuff CEO Rafael Ilishayev: The Plan to Make GoPuff Profitable by 2024 | 20VC #944 · 20VC with Harry Stebbings
Jun 16, 2025 negative
Opinion
Silicon Valley exhibits sheep-like herd mentality in secondary trading
“One of the issues with Silicon Valley, one of the benefits of being in Chicago is we isolate ourselves a bit from the herd mentality. And it's like, sometimes it's like sheep. They just jump one on after another and they buy more stock and things that you see …”
Larry Aschebrook Jun 16, 2025 ▶ 31:49 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
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