Chicago, every mention

74 scenes · ← back to Chicago

tap a year for its mentions
001052010201520162017201820192020202120222023202420252026episodesmentions
0510201520162017201820192020202120222023202420252026episodes it came up in
0025410201520162017201820192020202120222023202420252026episodesmentions per episode

every year anyone Ezra Galston 7Scott Dorsey 5Steven Galanis 4Peter Rahal 4Harry Stebbings 4Arteen Arabshahi 4Jason Fried 3Daniel Khachab 3Adam Grenier 3Scott Gorlick 2

Verbatim, from the transcripts: the passages where Chicago comes up

loading…

Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash Aug 17, 2026 · 1 mention

  • ▶ 25:01 Andrew Macdonald (Mac) But yes, of course, if autonomy starts to make up the majority of markets in San Francisco, LA, DC, Miami, New York, Boston, Chicago, like

The Hardest Working Startup in America | Nico Laqua, Co-founder & CEO @ Corgi · 20VC with Harry Stebbings May 30, 2026 · 1 mention

20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets Jan 9, 2026 · 1 mention

  • ▶ 27:07 Chad Peets You have another one in, you know, pick a state, Chicago, or, you know, Illinois rather.

20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster Nov 21, 2025 · 1 mention

  • ▶ 6:45 Max Altman Um, I was a quant trader after college because I wanted to go to Chicago as a Midwesterner.

20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable Oct 31, 2025 · 1 mention

  • ▶ 8:49 Tim Ferriss I marketed that to tech-savvy males, let's just say between the ages of 20 and 35 in San Francisco first, then New York City, then it hopped to the same demographic in Chicago and LA and so on, then it hopped to females in roughly those…

20VC: Why AI SDRs are BS and Do Not Work | How to Use AI in Your Sales Team and Process to Win Today | What Skills Do All New Reps Need to Have in an AI First World with Amit Bendov, CEO @ Gong Sep 12, 2025 · 1 mention

  • ▶ 12:46 Amit Bendov So I went to this first conference in Chicago in, uh, 2016, April, and I present, like, uh, I still have the deck, like, how AI will transform sales, and people's jaws dropped.

20VC: The $BN Greenoaks Backed Protein Bar | Hitting $100M Revenues in David's First Year: Lessons & Mistakes | $0 to $600M: The Untold RXBAR Story | Product-Market-Fit, Pricing, Branding: What Every Founder Gets Wrong Today with Peter Rahal Aug 8, 2025 · 4 mentions

Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings Jun 16, 2025 · 1 mention

  • ▶ 31:49 Larry Aschebrook We sold most of before the IPO, and you know, we won't talk about the names that buy, but you'd be surprised of the, it's kind of, I think one of the issues with Silicon Valley, one of the benefits of being in Chicago is we isolate…

Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings Mar 26, 2025 · 1 mention

  • ▶ 1:20:28 Mitchell Green So, uh, lots of things, but I would say the biggest thing we've, we did is, as we started to call more and more non-Silicon Valley based companies, our, our, you know, 18, 20 associates, you know, 22, twenty-four-year-olds were like, dude…

Oscar Pierre, Glovo CEO & Founder: Selling 30% for €100K |The McDonald's Deal That Saved Them |E1263 · 20VC with Harry Stebbings Feb 26, 2025 · 1 mention

  • ▶ 13:16 Oscar Pierre The CEO of McDonald's in Chicago, uh, sends a message to all the countries, uh, and says, Hey, we, we have to go into delivery and we have one exclusive partner, which is Uber Eats.

Max Levchin, Founder & CEO @ Affirm:The Biggest Surprise Scaling to $18.7BN Market Cap · 20VC with Harry Stebbings Feb 5, 2025 · 1 mention

  • ▶ 1:03:08 Max Levchin The day we took PayPal public, my mom asked me, well, will you finally move back to Chicago and get a PhD?

Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings Jan 13, 2025 · 1 mention

  • ▶ 39:46 Shervin Pishevar So Travis was actually in Chicago the week that he lost his mother, um, and recruiting a chief operating officer.

Daniel Khachab: "We Are in the Middle of a Cold War for AI Talent" | E1220 · 20VC with Harry Stebbings Oct 28, 2024 · 3 mentions

David Frankel, MP @Founder Collective: Investing Lessons from Seeding Coupang, Pillpack & Suno|E1214 · 20VC with Harry Stebbings Oct 14, 2024 · 1 mention

  • ▶ 1:14:38 David Frankel And Micah Rosenblum, my partner's father, Lou Rosenblum, was one of the best, he's out of Chicago, one of the best bankruptcy lawyers in, in the US.

Shardul Shah: How Index Makes Decisions & Why Benchmarks & Averages in VC are BS | E1202 · 20VC with Harry Stebbings Sep 16, 2024 · 1 mention

  • ▶ 1:25 Shardul Shah Like, growing up, I grew up outside of Chicago, and so my childhood hero was, um, Michael Jordan.

David Schneider: Why the Worst VCs are "Seagull VCs" & VC Value Add - Is it Real? | E1200 · 20VC with Harry Stebbings Sep 11, 2024 · 2 mentions

Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196 · 20VC with Harry Stebbings Aug 30, 2024 · 2 mentions

  • ▶ 1:49 Scott Gorlick But nothing really clicked, um, until I was in Chicago one night.
  • ▶ 19:37 Scott Gorlick Um, and, you know, we had an Atlanta city team, we had a Philadelphia team, we had a Chicago team and Lyft operated completely out of San Francisco.

Kevin Ryan: Are the Best CEOs the Best Fundraisers & Why Ownership Should Not Be a Focus in VC|E1138 · 20VC with Harry Stebbings Apr 10, 2024 · 1 mention

Chandra Narayanan: Top 5 Lessons from Leading Analytics at Facebook | E1126 · 20VC with Harry Stebbings Mar 13, 2024 · 1 mention

  • ▶ 53:59 Chandra Narayanan Underindex, I mean, so for example, overindexing and underindexing means that if you have a certain, uh, if New York is going up, you're asking if Chicago also is going up, you need to benchmark to something.

Peter Lacaillade: Why Now is the Best Time to Invest in Emerging Managers | E1096 · 20VC with Harry Stebbings Dec 18, 2023 · 1 mention

  • ▶ 14:40 Peter Lacaillade Like he, and you can't, I talk to him often at, um, it's like before seven AM East coast, he's in Chicago.

Matt Rosenberg: Why You Should Not Hire Sales Leaders From Big Companies | E1068 · 20VC with Harry Stebbings Oct 4, 2023 · 1 mention

  • ▶ 1:08 Matt Rosenberg I was a lawyer in Chicago, sitting in a very large office building, wearing a suit in a very large, um, office.

Adam Besnivick: How to Invest in Pre-Seed & Seed Stage Companies; Looking Glass Capital | E1020 · 20VC with Harry Stebbings May 29, 2023 · 1 mention

  • ▶ 10:49 Adam Besvinick Um, but a lot were in other, I'll call secondary tertiary tech hubs, Austin, Chicago, Boulder, San Diego, Portland, Oregon, Toronto, Durham, North Carolina, Boston.

Adam Grenier: The Inside Story to Uber’s Hypergrowth; How We Spent $1B/mo in China | E989 · 20VC with Harry Stebbings Mar 15, 2023 · 3 mentions

  • ▶ 39:12 Adam Grenier Then it may be like, uh, what about like safety in Chicago, right? 3 times in the scene

Mike Duboe: Top 5 Lessons Scaling Stitch Fix to IPO; Why CAC/LTV is a BS Metric | 20VC #978 · 20VC with Harry Stebbings Feb 16, 2023 · 2 mentions

  • ▶ 0:59 Mike Duboe Most folks at that time out of engineering school were either going to work in the auto industry in Detroit or moved to Chicago or New York to work in business. 2 times in the scene

Basecamp CEO Jason Fried: We Banned Talking Politics and 1/3 of our Team Quit | 20VC #963 · 20VC with Harry Stebbings Jan 6, 2023 · 1 mention

Bob Pittman: How I Went from Creator of MTV to CEO of iHeartMedia | 20VC #958 · 20VC with Harry Stebbings Dec 9, 2022 · 2 mentions

  • ▶ 2:19 Bob Pittman Um, I was, uh, I was, I mean, how did I go from being a fifteen-year-old disc jockey in Brookhaven, Mississippi, to programming the NBC station in Chicago when I was 20 years old? 2 times in the scene

GoPuff CEO Rafael Ilishayev: The Plan to Make GoPuff Profitable by 2024 | 20VC #944 · 20VC with Harry Stebbings Nov 2, 2022 · 1 mention

  • ▶ 11:07 Rafael Ilishayev Philadelphia, Chicago's, uh, Boston's, Miami's, uh, all of our Texas markets of the world that are, are producing cash flow.

Emil Michael: How I Negotiated the $4B Uber-China Deal, Why DoorDash Caught Up to Uber | 20VC #941 · 20VC with Harry Stebbings Oct 25, 2022 · 2 mentions

  • ▶ 43:00 Emil Michael Is when they cornered him in a hotel room in Chicago and gave him the, I'm going to smear you letter or you're going to quit without counsel in an hour letter. 2 times in the scene

Sheel Mohnot: Lessons from Investing in Flexport and Missing on Robinhood | 20VC #917 · 20VC with Harry Stebbings Aug 15, 2022 · 1 mention

  • ▶ 3:55 Sheel Mohnot You know, when I, I was moving to San Francisco, um, from Chicago, and I thought it would allow me to do a few things.

Welcome 20Growth: How To Hire a Head of Growth? What are Signs of World-Class Talent? How To Structure the Process? How To Onboard Growth Teams? The Relationship Between Head of Growth and CEO and more with Casey Winters, Chief Product Officer @ Eventbrit Sep 22, 2021 · 1 mention

  • ▶ 5:05 Casey Winters So I was there for five and a half years, and as I kind of wrapping up and thinking about what was next, you know, Grubhub was in Chicago.

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 Sep 16, 2021 · 1 mention

20VC: Basecamp CEO Jason Fried on His Relationship To Risk, Money, Vulnerability and Self-Doubt, Fantasising About Being Fired, How To Optimise Decision-Making and Minimising Regret Mar 22, 2021 · 2 mentions

  • ▶ 3:16 Jason Fried So I went to interview at some places, and during that process, I met a fellow named Ernest Kim, who is currently the creative director at a big web design shop in Chicago called Organic Online. 2 times in the scene

20VC: Robinhood Founder Vlad Tenev on His Biggest Lessons Managing Through A Crisis, The Events of The Congressional Committee, Raising $2.4Bn Fast and Why It Was Necessary & Why It Is Ludicrous To Suggest Robinhood Put The Business Ahead of it's Customer Mar 4, 2021 · 1 mention

  • ▶ 3:54 Vlad Tenev This was also kind of a turning point in institutional finance because it basically went from people placing trades on, on the floor, you know, humans being involved in, in these transactions and in trading to completely automated, you…

20VC: Why VCs Should Care More About Cost of Capital and Less About Ownership, Investing Lessons from working with Peter Thiel at Founders Fund, Why Liquidity Aligns Incentives Between Founders and Investors & Why It Is The Last Double That Matters in Ven Feb 4, 2021 · 1 mention

20VC: Loom Founder Joe Thomas on Whether To Take Multi-Stage Money at Seed, How Early Stage Founders Should Select Their VC, How Sequoia Won The Loom Deal & The 3 Rules To Operate Remote Teams Successfully Aug 7, 2020 · 1 mention

20VC: Raising A $1.35Bn Fund I, The Emerging Secondary Opportunity For Early Stage Managers and Founders & What It Takes To Win The Best Growth Deals Today with Ravi Viswanathan, Founder & Managing Partner @ NewView Capital Apr 6, 2020 · 1 mention

  • ▶ 21:19 Ravi Viswanathan You know, we've done deals in Toronto and Atlanta and Chicago where they're used to actually operating with a very lean mindset because there just wasn't so much venture out there.

20VC: Alexa Von Tobel on Raising NYC's Largest Ever Female Led Fund , Portfolio Construction, Compression of Fundraising Timelines, Reserves Management & Personal Branding in Venture Jan 31, 2020 · 1 mention

  • ▶ 34:48 Alexa von Tobel You know, my business partner, Penny, is a huge leader in Chicago, and you're seeing pockets of innovation happening everywhere from Atlanta to Austin to Boulder, and just making sure that over time, like, we all pay it forward to all of…

20VC: Inside UiPath, The World's Fastest Growing Startup, How The Best Leaders Approach Decision-Making & WhY Vulnerability Is Central To SuccessFul Leadership Today with Brandon Deer, VP of Operations & Strategy @ UiPath Dec 20, 2019 · 1 mention

20VC Exclusive: Roy Bahat on Bloomberg Beta's New Fund, The Truth About Valuation That Very Few VCs Will Tell You & Why Founders of Venture Backed Startups Make The Best Angels Oct 18, 2019 · 1 mention

  • ▶ 31:52 Roy Bahat I mean, everything from like the chairman of an international multifaceted conglomerate from South Asia to Rahm Emanuel, the mayor of Chicago, came and spoke to our crowd, Mike himself, science fiction authors, etc.

20VC: The Ultimate Episode For Emerging Managers: How To Determine How Big A Fund To Raise, What Is The Right Closing Strategy With LPs & Why We Will Not See The Eradication of Pre-Seed with John Fein, Founder & Managing Partner @ Firebrand Ventures Oct 7, 2019 · 1 mention

  • ▶ 36:06 John Fein Um, they're based in Chicago and they sell their services to, to multi-tenant buildings.

20VC: Cameo's Steven Galanis on Why You Must Fall In Love With Your Mission Not Your Product, How To Extract As Much Value From Your Investor Base As Possible & Should You Really Hire For 6 Months Ahead of What You Need? Jun 28, 2019 · 5 mentions

  • ▶ 0:40 Harry Stebbings And prior to founding Cameo, Stephen was a senior account exec at LinkedIn, and before that was an options trader in Chicago.
  • ▶ 7:16 Steven Galanis He flew in for the day to Chicago for my grandmother's funeral.
  • ▶ 19:56 Steven Galanis Cameo's early success and my ability to build my dream company in my hometown of Chicago. 2 times in the scene
  • ▶ 28:28 Steven Galanis Um, you know, right now, we're, we're sitting in Chicago whiteboarding out all the billion-dollar businesses we think we can build on top of this, whether it's just expanding the core product, whether it's creating a

20VC: Why Consumer Brands Must Embrace Physical Retail To Avoid Inflated Online CACs, How To Alter Fund Strategy When Investing In Consumer Retail & Why The Era of The 1,000 Store Brand Is Over with Brendan Wallace, Founder and Managing Partner @ Fifth Wa May 6, 2019 · 1 mention

  • ▶ 14:11 Brendan Wallace They have seven locations already just within Chicago because they're actually building that network effect

20VC: Techstars Founder David Cohen on Why Seed Investing Is A Different Asset Class To Venture, What Makes The Best And The Worst Board Members & Why Every Company Has To Have A Pessimist In The Room Feb 11, 2019 · 1 mention

  • ▶ 23:44 David Cohen And so I think getting everybody aligned about doing business, not just in Boulder and not just in LA and New York and Chicago, right.

20VC: Learnings From Backing The Likes of Spotify and Airbnb, The World of Growth Investing Today and The Right Way For Investors To Think About Liquidity with Woody Marshall, General Partner @ TCV Oct 8, 2018 · 1 mention

  • ▶ 3:52 Woody Marshall Presentation that was being done by, um, an environmentalist, and while I was at the cocktail hour after, I was introduced to a Chicago-based VC, a guy that had just founded a firm called Trident Capital.

20VC: Why Partners Are There To Save Each Other From Themselves, Why Effective Reserve Allocation Is The Hardest Question In Venture & What Makes The Truly Special Board Members with Jeff Fagnan, Founding Partner @ Accomplice Aug 13, 2018 · 1 mention

  • ▶ 3:38 Jeff Fagnan I was working in Chicago and London, and I always thought that what I really wanted to do was, this is kind of an advent of so many web services and the internet.

20VC: GOAT's Eddy Lu on Pivoting From Failing Social Dining App To The World's Largest Sneaker Marketplace, How The Best Founders Pick Their Investors & Why It Is Better To Be Hated than Unknown Jul 27, 2018 · 1 mention

  • ▶ 4:12 Eddy Lu But the good thing is, while in Chicago, when we were opening up a new bakery location, we were new in town, we didn't really know anyone, so naturally we said, hey, let's solve this problem with technology.

20VC: Why Not Every Element of A Scalable Business Has To Scale, Why You Should Be Bearish on Retail & Why Fewer Businesses Are Getting Started Today Since The Great Depression with Brad Hargreaves, Founder & CEO @ Common Aug 11, 2017 · 1 mention

20VC: Why Founders Should Not Focus On Top Line Valuation, Why Capital Efficiency Is Key To Returns And Investment Success & Why Despite Popular Thought, $100m Is An Exciting Exit For VC with Micah Rosenbloom, Managing Partner @ Founder Collective Feb 15, 2017 · 2 mentions

  • ▶ 3:42 Micah Rosenbloom And it happened that my, I grew up in Chicago, and I had a loose family connection to Ari Emanuel, and literally never met the man, never had, but it was a friend of a friend from Chicago. 2 times in the scene

20VC: The Radical Changes In Public Market Expectations, The Right Way To Assess Valuation & What It Means To Be A Disciplined & Diligent Investor with Randy Glein, Partner @ DFJ Growth Feb 8, 2017 · 2 mentions

  • ▶ 29:06 Randy Glein Well, so, you know, the Cubs is, uh, is a major league baseball team here based in Chicago. 2 times in the scene

20VC: The Fundamentals To Creating A Successful Venture Partnership & The Optimal Investment Decision Making Process with Ryan McIntyre, Co-Founder @ Foundry Group Feb 1, 2017 · 1 mention

  • ▶ 21:54 Ryan McIntyre So we played the house of blues in Chicago, great American music hall in San Francisco, things like that.

20VC: Lessons Learnt From Marc Benioff & Selling To Salesforce For $2.7bn, What Product Market Fit Really Looks Like & Why Pricing Is Startup's Biggest Problem with Scott Dorsey, Managing Partner @ HighAlpha Dec 5, 2016 · 5 mentions

  • ▶ 3:35 Scott Dorsey And I largely grew up in the Chicago area. 2 times in the scene
  • ▶ 6:19 Scott Dorsey Chicago tech entrepreneurs.
  • ▶ 9:59 Scott Dorsey It was our lead investor, and then Hyde Park out of Chicago, and we have about 20 to 25 of us, designers, developers, analysts, subject matter experts in, in how to scale SaaS companies.
  • ▶ 24:02 Scott Dorsey And then we're about three hours from Chicago.

20VC: The Rise Of The Celebrity VC & The Pros and Cons Of Staying Private with Logan Bartlett @ Battery Ventures Apr 20, 2016 · 1 mention

  • ▶ 20:58 Logan Bartlett Uh, and it's about a, uh, an academic PhD student that gets the opportunity to go inside a Chicago gang ecosystem, uh, for over the course of a couple years and actually gets to run it for a single day.

20VC: Sprig's Gagan Biyani on The 3 Principles Of Fundraising and Building The World's Largest Restaurant Apr 8, 2016 · 2 mentions

  • ▶ 11:04 Harry Stebbings Is it Chicago because it's rainy and cold and people don't want to go out? 2 times in the scene

20VC: Greylock's Josh Elman on Why We Are Not In A Consumer Downturn, The Next Wave Of Social and What Twitter Should Do Next Apr 4, 2016 · 1 mention

  • ▶ 12:20 Josh Elman Or a group of twenty-something workers in, you know, in Chicago, like where they're all now changing their behavior, adapting their behavior to some new product.

20 VC: The Ultimate Guide To Marketplaces with Boris Wertz, Founding Partner @ Version One Ventures Dec 28, 2015 · 1 mention

  • ▶ 27:04 Boris Wertz So they're currently active in six cities, including New York, San Fran, Las Vegas, LA, Chicago, and they basically let you, um, kind of buy, um, tickets and access to travel experiences for the next 24 hours, kind of upcoming 24 hours.

20 VC 078: BETAWORKS WEEK: Matt Hartman, Director of Seed Investments @ Betaworks Oct 12, 2015 · 1 mention

20 VC 063: What It Takes To Standout In A Crowded Market with Ezra Galston @ Chicago Ventures Aug 17, 2015 · 7 mentions

  • ▶ 8:02 Ezra Galston The other way is that Chicago is actually really an extraordinary consumer market, which is where I spend a lot of my time. 5 times in the scene
  • ▶ 13:40 Ezra Galston So we've got Grubhub here in Chicago and, and, um, you know, we're very close with, with the team there.
  • ▶ 24:26 Ezra Galston I actually, I'm getting to meet him tomorrow night, because he's in Chicago for a meetup, and I'm literally geeking out as if, like, you know,

20 VC 059: How To Approach VCs with Arteen Arabshahi, VC @ Karlin Ventures Aug 3, 2015 · 4 mentions

  • ▶ 5:58 Arteen Arabshahi Um, and at the time it was called Accelerate Labs, and they were looking for somebody to kind of join their operations team for, for the subsequent summer, and, you know, went through just the traditional interview process, ended up… 2 times in the scene
  • ▶ 12:19 Arteen Arabshahi Which actually reminds me, I think, I think the person that I always, um, you know, so Troy from, from Texas or Chicago obviously was, was a, was a, a super helpful part of that whole process, right? 2 times in the scene

20 VC 022: Letting go of the life we planned and the Power of the Female Narrative with Matthew McCall Mar 26, 2015 · 3 mentions

  • ▶ 0:25 Harry Stebbings Matt's incredible success has led to Chicago naming him in the 40 under 40, in their top tech 25, and he has been named in the top a hundred VCs in the US, and he is also a Hollywood hundred power player.
  • ▶ 13:54 Matthew McCall And the reason was in 2008, it was, uh, in one week, um, all of the term sheets from West Coast firms in Chicago vaporized. 2 times in the scene
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.