Randy Fifield

9 statements across 1 episodes · 4 bullish · 0 bearish · 1 people on the record · first statement Dec 29, 2025 by Randy Fifield · across every show →

On the record as a speaker too: Randy Fifield's record, appearances and statements → this page counts the times other people say the name.

Everything said about Randy Fifield, oldest first

Dec 29, 2025 neutral

Assertion Supported

Fifield: Ambassador Hotel was purchased out of foreclosure

“And we bought this asset out of foreclosure.”

Randy Fifield Dec 29, 2025 ▶ 24:34 Starting Small in Real Estate Can Lead to Massive Wealth

Dec 29, 2025

Assertion Partly supported

Fifield: I have developed around $8B in real estate over my career

“Today in my whole lifetime Oh my gosh, probably like, eight billion dollars of development.”

Randy Fifield Dec 29, 2025 ▶ 50:57 Starting Small in Real Estate Can Lead to Massive Wealth

Dec 29, 2025

Disclosure

Fifield: Syndicate paid all cash for Chicago's Ambassador Hotel

“She is almost 300 rooms in the Gold Coast of Chicago. We Paid cash for her, put a group together.”

Randy Fifield Dec 29, 2025 ▶ 17:46 Starting Small in Real Estate Can Lead to Massive Wealth

Dec 29, 2025 bullish

Opinion

Fifield: Real estate deals exist constantly despite claims of stalled markets

“Sometimes you talk to people like, Paul, there's no deals. There's nothing's getting done. And I'm like, that's not true. Deals cross my desk every day. It's whether you have the appetite to do them, the money to do them, the desire to do them, the risk profil…”

Randy Fifield Dec 29, 2025 ▶ 40:40 Starting Small in Real Estate Can Lead to Massive Wealth

Dec 29, 2025 positive

Disclosure

Fifield: Doubled Invested Capital Within a Year on First Six-Unit Property

“We built the garage, we rented the garage spaces, we renovated the units, we upped the rent, and lo and behold, a year later, we almost doubled our money.”

Randy Fifield Dec 29, 2025 ▶ 2:12 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

Dec 29, 2025 positive

Assertion Contradicted

Fifield: Landlords Can Remove Affordable Housing Designations by Moving Children In

“You can also use the Ellis act. And if you have your children that are living in this building, you can take affordable housing and make it market rate housing.”

Randy Fifield Dec 29, 2025 ▶ 7:33 Starting Small in Real Estate Can Lead to Massive Wealth

Dec 29, 2025

Disclosure

Fifield discloses having properties surrendered to the bank

“I have had buildings go back to the bank, not because I did something wrong, but the pro formas said, you need to rent the parking, you need to rent the units at this price and the land was purchased for X and it was as of right.”

Randy Fifield Dec 29, 2025 ▶ 58:07 Starting Small in Real Estate Can Lead to Massive Wealth

Randy Fifield

Everything said about Randy Fifield, oldest first

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