Episode 569: Richard Baker: Entrepreneurship Lessons From Billion Dollar Deals and Bold Risks
7/7/20261 hr 28 min
Are you actually creating opportunity, or are you waiting for someone to hand it to you?
A lot of people talk about being entrepreneurs, but very few are willing to do the unsexy part: get on the plane, sit in the waiting room, build the relationship, ask the better question, and stay in the deal long enough to find the angle everyone else missed. Richard Baker built his career by doing exactly that. He did not rely on perfect timing, endless capital, or permission from people at the top. He used structure, relationships, leverage, and speed to turn overlooked opportunities into billion-dollar deals.
This matters because the future of work is changing fast. AI is reshaping business, companies are cutting jobs, and more people are going to have to learn how to create value on their own. Richard's philosophy is simple: stop chasing safety, start thinking like an owner, and learn how to manufacture your own luck. The people who win are the ones who know where the ball is going before everyone else starts running after it.
Richard Baker is a real estate entrepreneur, dealmaker, founder of Baker House 1921, and longtime educator through Cornell's Baker Program in Real Estate. He has built one of the largest privately owned shopping center portfolios in the country, developed 50 Walmart-anchored shopping centers, bought iconic retail brands including Lord & Taylor, Saks Fifth Avenue, Hudson's Bay, and Neiman Marcus, and structured some of the most fascinating retail and real estate deals of the last two decades. In this episode, he breaks down negotiation, risk, AI, entrepreneurship, decision-making, and why the biggest opportunities often come from seeing what everyone else is too busy to notice.
What's Discussed:
(01:27) How Richard Baker built one of the largest privately owned shopping center portfolios in the country.
(07:37) The family philosophy that taught him how to make money with no money.
(11:13) What intellectual leverage means and why he uses brains, relationships, and structure instead of cash.
(12:15) Why real opportunity comes from getting off your ass and showing up in person.
(19:23) How the power of yes helped him buy Lord & Taylor for $1.2 billion.
(23:34) Why big companies miss details and how that creates openings for entrepreneurs.
(29:21) Why speed, risk tolerance, and fast decision-making matter in business.
(39:17) How he turned the Zellers deal into a bidding war between Walmart and Target.
(52:40) The difference between a zoo bear and a jungle bear in entrepreneurship.
(01:02:39) Why luck is something you manufacture through preparation, strategy, and timing.
(01:07:21) How Richard uses AI every morning to think, plan, and increase productivity.
(01:31:38) Why courage, pulling the trigger, and structuring risk are essential for entrepreneurs.
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Find more from Jen Cohen:
Website: jennifercohen.com
Instagram: @therealjencohen
Books: jennifercohen.com/books
Speaking: jennifercohen.com/speaking-engagements
Find more from Richard Baker & Baker House:
Website: bakerhouse1921.com
Instagram: @baker_house1921
Clips
Transcript preview
First 90 secondsRichard Baker· Guest0:00
[upbeat music] Hi, guys. It's Tony Robbins. You're listening to Habits and Hustle. Crush it.
Jennifer Cohen· Host0:04
Hi, everybody. We have... Welcome to another episode of Habits and Hustle. I have a funny guest on today. Um, not really that... Well, I don't know, but you seem like you're very, uh, you've got a lot of levity. Uh, his name is Richard Baker, and I would say he's gonna probably give you a better definition of what he does. But let's just say he has the... He owns and runs the largest real estate private company in the country.
Richard Baker· Guest0:30
One of the largest private owners of shopping centers in the United States. Let's leave it at that.
Jennifer Cohen· Host0:35
Let's just say he's extremely successful in the real estate space, and we're gonna learn a lot from him on negotiation, deal structure, like, sourcing opportu- opportunities, seeing... All the things business. So before I, like, make more of a mess of this, why don't you describe in a few sentences who you are and what you do?
Richard Baker· Guest0:55
Sure. So basically, I think of myself as a small-time entrepreneur, and I just did a lot of deals over and over and over. So when you add it all up, it turned out to be a big thing. Uh, I started out, uh, working with my father in the real estate space and, um, there was this company that had no stores east of the Mississippi called Walmart. It was a long time ago. And I said, "Wow, I should go visit these people in Bentonville, Arkansas." So I got on a plane and I sat in the offices for two days of the, uh, of Walmart.