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Richard Baker07 July 2026

Episode 569: Richard Baker: Entrepreneurship Lessons From Billion Dollar Deals and Bold Risks

7Frameworks
10Insights

Episode overview

Jennifer Cohen interviews real-estate entrepreneur Richard Baker about building Walmart-anchored shopping centers and acquiring major department-store businesses through real-estate-backed deal structures. Baker recounts the Lord & Taylor, Hudson's Bay, Zellers, Saks, and Neiman Marcus transactions, including successes, bankruptcy decisions, and the value of negotiating directly with decision-makers. He argues that entrepreneurs should cultivate courage, work harder than competitors, build genuine relationships, move quickly, and use creativity and AI to increase their leverage.

Key ideas

  • Structure deals around intellectual leverage, credit tenants, options, and financing so personal capital at risk remains limited.
  • Manufacture luck through preparation, hard work, relationships, and anticipating where markets are going.
  • Negotiate with actual decision-makers and preserve trust, even when a richer offer arrives after a handshake agreement.
  • Move quickly when downside risk is limited, while recognizing that speed can reduce the amount of analysis used.
  • Distressed operating companies can contain real-estate or leasehold value that conventional buyers overlook.
  • Entrepreneurship requires courage, sustained energy, focus, curiosity, and complementary partners.
  • AI tools such as Claude can multiply an entrepreneur's research, planning, and communication capacity.
  • As access to intelligence becomes commoditized through AI, creativity, empathy, and human relationships become more valuable.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Strategy3 steps

Bounded-Downside Speed

Where the downside is small, act fast and everywhere — don't test your way to obvious wins.

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Finance3 steps

Intellectual Leverage

Control billion-dollar assets with almost none of your own money — use your brain as the capital.

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Influence3 steps

Maneuver to the Decision-Maker

Deal with the person who can say yes — big companies that hand it down lose the moment.

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Mindset3 steps

Manufacture Your Own Luck

Skate to where the ball is going — preparation and positioning look like luck from outside.

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Finance4 steps

OpCo/PropCo Capture

Buy the whole failing company just to own the real estate underneath it — then split and monetize.

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Strategy3 steps

The One-Contact Open Auction

Run your own bidding war: no brokers, one point of contact, and the hardest deal wins.

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Influence3 steps

The Power of Yes

When the price is already a bargain, don't haggle — win with speed and certainty of close.

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People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 13

  • Richard BakerMentionshis name is Richard Baker

    “his name is Richard Baker”

    ▶ Watch at ~0:30approx.
  • Jennifer CohenMentionsI'm a podcaster, but I'm also an investor. I'm a podcaster I'm a fitness person, but I'm also had two successful exits.

    “Welcome to another episode of Habits and Hustle. I have a funny guest on today.”

    ▶ Watch at ~0:30approx.
  • Richard BakerMentionshis name is Richard Baker

    “I think of myself as a small-time entrepreneur and I just did a lot of deals over and over and over.”

    ▶ Watch at ~1:30approx.
  • SylviaMentionsmy grandmother, Sylvia, came from Poland in 1921 on July 4th through Ellis Island

    “my grandmother, Sylvia, came from Poland in 1921 on July 4th through Ellis Island”

    ▶ Watch at ~6:30approx.
  • Mr. LevinsonMentionsI meet with a fellow by the name of Mr. Levinson.

    “I meet with a fellow by the name of Mr. Levinson.”

    ▶ Watch at ~12:30approx.
  • Ron TysoeMentionsthis fellow by the name of Ron Tysoe, who was the vice chairman of what was then called Federated

    “this fellow by the name of Ron Tysoe, who was the vice chairman of what was then called Federated”

    ▶ Watch at ~18:00approx.
  • Jane ElfersMentionsThere was a great CEO at the time by the name of Jane Elfers

    “There was a great CEO at the time by the name of Jane Elfers”

    ▶ Watch at ~27:00approx.
  • Adam NeumannMentionsI sold the building for 850 to Adam Neumann at WeWork.

    “I sold the building for 850 to Adam Neumann at WeWork.”

    ▶ Watch at ~32:30approx.
  • Don WatrousMentionsone guy by the name of Don Watrous who was our chief operating officer saved the company

    “one guy by the name of Don Watrous who was our chief operating officer saved the company”

    ▶ Watch at ~37:00approx.
  • Grand Chief Jerry DanielsMentionsGrand Chief Jerry Daniels, the the chief the the Grand Chief of the First Nations people

    “Grand Chief Jerry Daniels, the the chief the the Grand Chief of the First Nations people”

    ▶ Watch at ~48:00approx.
  • RyanMentionsRyan worked on our team at Saks Fifth Avenue, and was very talented.

    “Ryan worked on our team at Saks Fifth Avenue, and was very talented.”

    ▶ Watch at ~1:04:00approx.
  • Barbara CorcoranMentionsmentioned

    “like the like the Barbara Corcorans of the world?”

    ▶ Watch at ~1:10:00approx.
  • Joe De SenaCoinedJoe De Sena from Spartan Races dreamt this idea up.

    “Joe De Sena from Spartan Races dreamt this idea up.”

    ▶ Watch at ~1:11:00approx.

Resources · 27

  • Habits & HustleCoinedpodcast · Jennifer Cohen

    “Welcome to another episode of Habits and Hustle.”

    ▶ Watch at ~0:30approx.
  • WalmartMentionscompany

    “there was this company that had no stores east of the Mississippi called Walmart.”

    ▶ Watch at ~1:30approx.
  • Hudson's Bay CompanyMentionscompany

    “I bought the Hudson Bay Company in July 19th of 2008”

    ▶ Watch at ~3:00approx.
  • Cornell Hotel SchoolMentionscompany

    “I decided I wanted to go to the Cornell Hotel School to learn how to be an operator of businesses”

    ▶ Watch at ~9:00approx.
  • Bentonville, ArkansasMentionsplace

    “I got on a plane, I flew to Bentonville, Arkansas.”

    ▶ Watch at ~11:30approx.
  • McDonald'sMentionscompany

    “I made a deal with McDonald's.”

    ▶ Watch at ~14:00approx.
  • Hannaford BrothersMentionscompany

    “I signed a deal with a Hannaford Brothers supermarket chain.”

    ▶ Watch at ~14:00approx.
  • KKRMentionscompany

    “They had huge private equity firms, KKR, and all these guys.”

    ▶ Watch at ~17:30approx.
  • NRDC Equity Partners Fund SevenCoinedcompany · Richard Baker

    “The entity I was using was something called NRDC NRDC Equity Partners Fund Seven, and that was what was in the papers.”

    ▶ Watch at ~21:30approx.
  • Lehman BrothersMentionscompany

    “The wonderful banking firms of Lehman Brothers, Bear Stearns, and CIT”

    ▶ Watch at ~24:30approx.
  • Bear StearnsMentionscompany

    “The wonderful banking firms of Lehman Brothers, Bear Stearns, and CIT”

    ▶ Watch at ~24:30approx.
  • CITMentionscompany

    “The wonderful banking firms of Lehman Brothers, Bear Stearns, and CIT”

    ▶ Watch at ~24:30approx.
  • AmazonMentionscompany

    “I flipped the building to Amazon for $1.2 billion.”

    ▶ Watch at ~31:30approx.
  • WeWorkMentionscompany

    “I sold the building for 850 to Adam Neumann at WeWork.”

    ▶ Watch at ~32:30approx.
  • TargetMentionscompany

    “we hear that you're negotiating a deal with Target to buy Zellers.”

    ▶ Watch at ~38:00approx.
  • WinnipegMentionsplace

    “the Hudson's Bay store in downtown Winnipeg”

    ▶ Watch at ~48:00approx.
  • Magic MindUsesproduct · James Beshara

    “this is a performance shot. Mine has no caffeine. Yours has triple caffeine. It's by Magic Mind.”

    ▶ Watch at ~53:30approx.link ↗
  • ErewhonRecommendscompany

    “You can buy them at Erewhon. You can have a subscription. You can buy them on the website.”

    ▶ Watch at ~54:30approx.
  • ClaudeUsessoftware · Anthropic

    “I spend two hours every single morning talking to Claude and plotting and working and figuring stuff out”

    ▶ Watch at ~1:00:00approx.
  • Santa Teresa, Costa RicaMentionsplace

    “This was a Santa Santa Teresa.”

    ▶ Watch at ~1:05:00approx.
  • CohnReznickMentionscompany

    “We're going to have boot camps starting this fall that are sponsored by Cohn Resnick and Wilkie Farr”

    ▶ Watch at ~1:06:30approx.
  • Baker HouseCoinedcompany · Richard Baker

    “So Baker House is going to be located at Cornell's campus.”

    ▶ Watch at ~1:07:00approx.
  • Baker House Boot CampCoinedcourse · Richard Baker

    “we've decided to build and offer this Baker House boot camp”

    ▶ Watch at ~1:08:00approx.
  • Willkie Farr & GallagherMentionscompany

    “they're sponsoring it along with Wilkie Farr, another law firm.”

    ▶ Watch at ~1:08:30approx.
  • Spartan RaceMentionsevent · Joe De Sena

    “Joe De Sena from Spartan Races dreamt this idea up.”

    ▶ Watch at ~1:11:00approx.
  • Baker HouseMentionscompany · Richard Baker

    “go on our website bakerhouse1921.com”

    ▶ Watch at ~1:16:30approx.
  • Cornell UniversityMentionscompany

    “This is a Cornell-based program that's authenticated by Cornell University.”

    ▶ Watch at ~1:17:00approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster1:19:00

Why You'd Go Bankrupt On Purpose

Bankruptcy isn't always failure. Baker filed Saks Global early — while there were still assets and inventory — to stop nervous vendors from cutting off goods and forcing a liquidation. It protected the business, the vendors and the jobs, and let the merged Saks/Neiman/Bergdorf entity reorganize and capture $600M/year of synergies.

  • Filing early (with assets left) protects vendors and prevents liquidation
  • The goal was to preserve the merger synergies, not to walk away
  • Baker personally lost ~$500M of equity but saved the companies

“We filed for bankruptcy early enough that there were still assets and inventory and things, and now the company's getting reorganized.”

#restructuring#bankruptcy#retail

Hot Take· 1

Hot Take1:31:00

The Revenge of the Creatives

Baker argues that being 'super smart and knowing lots of stuff' is becoming a commodity now that everyone has AI in their pocket. The power going forward is creativity, curiosity and thinking differently. He cites research that many top entrepreneurs and scientists were also crafters — painters, sculptors, cooks — which is why he's building a craft center into his entrepreneur program.

  • Smarts is now a commodity; creativity is the scarce edge
  • Hands-on craft correlates with top entrepreneurs and scientists
  • Empathy and human connection are the next-level, un-automatable skills

“Smarts is now becoming a commodity. I have Claude in my pocket. So the real power going forward is going to be creativity.”

#creativity#ai#future-of-work

Explainer· 2

Explainer51:30

Zoo Bear vs. Jungle Bear

Baker's mental model for the entrepreneurial mindset: a zoo bear works at a big firm, gets a lunchtime pellet and a pat on the head; a jungle bear eats what it kills — and dies if it kills nothing. Anyone who figures out how to feed themselves earns the entrepreneur banner, whether they drive Uber, sell bangles, or make jewelry on the side.

  • Zoo bear = salaried dependence; jungle bear = eat what you kill
  • The entrepreneur banner is earned by self-reliance, not company size
  • AI and corporate change will force more people into jungle-bear mode

“A jungle bear is an entrepreneur and they eat what they kill. And if they don't kill anything, they die.”

52:00
#mindset#entrepreneurship#self-reliance
Explainer57:00

The Kid Who Always Gets the Ball

Asked whether his success was luck or skill, Baker points to youth soccer: every kid chases the ball, but one kid always ends up with it and scores — because he understands where the ball is going, not where it is. Baker 'manufactures his own luck' by working harder, preparing more, and positioning ahead of where the world is heading.

  • Position where the ball is going, not where it is
  • Luck is downstream of preparation and effort
  • He mapped Walmart's sites before Walmart itself had

“That kid understands where the ball's going, not where the ball is.”

57:30
#strategy#luck#preparation

Story· 2

Story11:00

Two Days in a Walmart Trailer

At 21, Baker flew to Bentonville, Arkansas and waited two days in a trailer to meet Walmart's real-estate team — when almost no one on the East Coast had heard of the company. The relationship he built there became the foundation for 50 shopping centers. His lesson: get off your ass and show up in person.

  • Showed up uninvited and waited two days for the meeting
  • In-person presence beat every phone/email/Zoom alternative
  • One relationship seeded a 50-center, decades-long business

“You get off your ass and you go someplace. If Jen calls and says she has an opening, you get on a plane and you…”

#relationships#hustle#real-estate
Story32:30

The $850M Building That Became $1.2B

Baker sold the Lord & Taylor Fifth Avenue building to Adam Neumann's WeWork for $850M. When Neumann showed up $150M short at closing, Baker's partners took a preferred-equity note — reasoning the building wasn't even worth $850M. When WeWork imploded, that note put Baker in the mix to help sell the building to Amazon for $1.2B, and the preferred paid out.

  • Took paper instead of cash when the buyer came up short — because the downside was already covered
  • The preferred-equity position later became leverage in the Amazon sale
  • Amazon reportedly went on to make over $1B on the same building

“Who cares? The building isn't even worth close to 850 million. So you'll take a piece of paper and even if he never pays you…”

32:30
#deal-structure#real-estate#negotiation

Q&A· 1

Q&A1:27:00

Likability vs. Competence

Cohen argues the people who raise the most money and get the most opportunities are the most likable, because people want to work with people they like. Baker agrees it matters and he relies on it — but reframes it: business is about relationships, and if you're not personable you can't build them. Competence still comes first; likability is what gets a competent person the shot.

  • People fund and partner with people they like, not just the competent
  • Baker reframes likability as relationship-building, not charm
  • Do the right thing for everyone daily — the return comes back in a thousand ways

“People want to work with people they like, not just people who are competent.”

#relationships#influence#fundraising

Tool· 1

Tool1:00:30

Two Hours With Claude Every Morning

Baker spends two hours each morning prompting Claude — plotting deals, thinking through structures, and drafting memos he sends to his team to execute. He frames AI as replacing the 'dead weight' of building processes, and says his whole life was really about prompting: asking 'what if we did it this way?' Now the answer comes back in ten minutes instead of three weeks.

  • AI compresses a three-week research loop into ten minutes
  • He builds 2-4 'Claude memos' a morning and hands them to his team to execute
  • Framing: the durable human edge shifts from knowing things to creativity and connection

“I spend two hours every single morning talking to Claude and plotting and working and figuring stuff out and that's where the world's going.”

1:00:30
#ai#productivity#workflow

Takeaway· 2

Takeaway1:12:00

The Overlooked Real-Estate Entrepreneur

Baker sees a large opportunity in the millions of small mixed-use buildings (retail below, apartments above) owned by an aging generation. As those estates get a stepped-up tax basis and sell, local operators can buy, re-tenant and finance them tax-efficiently — without competing with Blackstone. He specifically argues women are natural real-estate entrepreneurs (not just agents) yet make up only ~10-20% of them.

  • A generational transfer of small mixed-use property is coming
  • Local entrepreneurs can win where institutions don't want the assets
  • Bonus depreciation and traditional financing make it tax-efficient

“There's going to be endless amounts of excellent investments for real estate entrepreneurs. And they're not going to be competing with Blackstone.”

#real-estate#opportunity#wealth-building
Takeaway1:14:30

Pick a Partner Who Isn't You

In Baker's boot camp he pairs people into teams of complementary strengths — the person with capital, the person good at running numbers, the personality/deal person. The recurring failure mode in partnerships is choosing someone who mirrors you; the right partner has the skills you lack and balances you out.

  • The right partner complements, not mirrors, your skill set
  • Deals fail when partners share the same qualifications and gaps
  • Baker literally structures his boot camp around forming complementary teams

“The right partner is not someone that looks just like you. The right partner is someone who compliments you and has skills that go with…”

1:15:00
#partnerships#team-building#entrepreneurship