Chicago

3 statements across 1 episodes · 1 bullish · 1 bearish · 1 people on the record · first statement Dec 29, 2025 by Randy Fifield · said 21 times in 3 episodes since 2025 · across every show →

Mentions by year

brought up most by Randy Fifield (19), Paul Mark Morris (1), Mike Lazerow (1)

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2026 2 mentions in 2 episodes 1 per episode
2025 19 mentions in 1 episode

every mention, scene by scene, with the transcript →

Everything said about Chicago, oldest first

Dec 29, 2025 bearish
Opinion
Fifield: Concrete high-rise residential construction is difficult in major US markets
“When you go downtown and you see concrete high rise construction on apartments, very, very difficult to do today in any sub market, New York, Chicago, even Nashville”
Randy Fifield Dec 29, 2025 ▶ 15:59 Starting Small in Real Estate Can Lead to Massive Wealth
Dec 29, 2025 bullish
Opinion
Fifield: Chicago conditions are getting better despite investors turning away
“I think if you had to ask me, I think this is a legacy asset, at least for me and my family, that's how in the category that it goes in. To invest in Chicago where a lot of people are turning their back on Chicago. It felt right to be part of a family organiza…”
Randy Fifield Dec 29, 2025 ▶ 24:37 Starting Small in Real Estate Can Lead to Massive Wealth
Dec 29, 2025
Disclosure
Fifield: I manage a $50M workforce housing fund in Chicago
“So I have a workforce housing fund, right? It is not, It's a unique unicorn. It's a market rate, affordable fund that it caters to baristas, teachers. It follows the same algorithm as the mid-rise and the high-rise, and basically I was able to start it in Chic…”
Randy Fifield Dec 29, 2025 ▶ 1:02:38 Starting Small in Real Estate Can Lead to Massive Wealth
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