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Complex Systems with Patrick McKenzie (patio11)
Trailer
Bonus
Episode 28
Season 1
The landmines buried in the fine print of Chicago’s new casino deal
In today’s episode Patrick McKenzie (@patio11) examines a Chicago casino investment, first of its kind within the city limits. Patrick reads from his Bits About Money essay (published January 2025) with additional commentary based on recent developments. The discussion reveals how municipal politics, grievances about national and local economic history, and creative financing intersect for ‘a very Chicago gamble.’
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Full transcript available here:
www.complexsystemspodcast.com/the-landmines-buried-in-the-fine-print-of-chicagos-new-casino-deal/
www.complexsystemspodcast.com/the-landmines-buried-in-the-fine-print-of-chicagos-new-casino-deal/
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Sponsors: Vanta | GiveWell | Check
Sponsors: Vanta | GiveWell | Check
Vanta automates security compliance and builds trust, helping companies streamline ISO, SOC 2, and AI framework certifications. Learn more at https://vanta.com/complex
Support proven charities that deliver measurable results and learn how to maximize your charitable impact with GiveWell. Go to givewell.org (and type in "Complex Systems" at checkout).
Check is the leading payroll infrastructure provider and pioneer of embedded payroll. Check makes it easy for any SaaS platform to build a payroll business, and already powers 60+ popular platforms. Head to checkhq.com/complex and tell them patio11 sent you.
Support proven charities that deliver measurable results and learn how to maximize your charitable impact with GiveWell. Go to givewell.org (and type in "Complex Systems" at checkout).
Check is the leading payroll infrastructure provider and pioneer of embedded payroll. Check makes it easy for any SaaS platform to build a payroll business, and already powers 60+ popular platforms. Head to checkhq.com/complex and tell them patio11 sent you.
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Links:
- Bits About Money: https://www.bitsaboutmoney.com/archive/chicago-casino-investment-offering/
- The Story of Vaccinate CA: https://worksinprogress.co/issue/the-story-of-vaccinateca/
- The Conservative Investor: https://www.patreon.com/theconservativeincomeinvestor
- Complex Systems interview with Jim McKenzie: https://open.spotify.com/episode/6ocJirzGTStuf0K9ITM21X?si=7HA0RhEOS8GFsA1MlY-EVw
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Twitter:
@patio11
@patio11
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Timestamps:
(00:00) Intro
(01:43) Chicago has wanted a casino for a long time
(04:55) The stock offering
(10:29) Chicago’s peculiar definition of minority
(14:04) Sponsors: Vanta | Check
(16:26) Reading a complex corporate structure
(20:29) Is this valuation a gift to investors?
(23:20) Capital stack arbitrage
(30:04) The casino will not distribute profits, per se
(32:45) Tax consequences of this offering
(38:34) In conclusion
(00:00) Intro
(01:43) Chicago has wanted a casino for a long time
(04:55) The stock offering
(10:29) Chicago’s peculiar definition of minority
(14:04) Sponsors: Vanta | Check
(16:26) Reading a complex corporate structure
(20:29) Is this valuation a gift to investors?
(23:20) Capital stack arbitrage
(30:04) The casino will not distribute profits, per se
(32:45) Tax consequences of this offering
(38:34) In conclusion