Uploaded July 2026 | Updated September 2026, 3 weeks ago
Entrepreneurship does not have a strategy problem. It has a courage problem. Everyone wants the opportunity, the deal, the leverage, and the big outcome, but very few people are willing to get on the plane, sit in the room, build the relationship, and take the risk before everything feels guaranteed.
Richard Baker is a real estate entrepreneur, dealmaker, founder of Baker House 1921, and longtime educator through Cornell’s Baker Program in Real Estate who has built one of the largest privately owned shopping center portfolios in the country. In this episode, he breaks down how he developed 50 Walmart-anchored shopping centers, bought Lord & Taylor for $1.2 billion, helped bring Target into Canada, and built a career by seeing value where other people saw problems.
We also talk about negotiation, using leverage without relying on cash, dealing directly with decision makers, manufacturing your own luck, and why the biggest players in the room are not always the smartest or fastest. Richard also explains why AI is going to create a massive wave of new entrepreneurs and how he personally uses it every morning to think, plan, and move faster.
If you have ever wondered what it really takes to think like an owner, create opportunity from nothing, and stop waiting for permission, this conversation will make you rethink business, risk, real estate, relationships, AI, and what entrepreneurship actually demands.
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.
Thank You to Our Sponsors!
Magic Mind: Head over to magicmind.com/jen and use code JEN at checkout.
Pique: Go to piquelife.com/jenniferrsd to get 20% off for life plus free gifts
Momentous: Ready to try supplements that actually do what they claim? Head to livemomentous.com and use code JEN for 35% off your first subscription.
Therasage: Visit therasage.com and use code JEN to get 15% off your order. Your skin
Prolon: Prolon is offering listeners 30% off sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit prolonlife.com/JENNIFERCOHEN and use code JENNIFERCOHEN to claim your discount and your bonus gift.
Entrepreneurship does not have a strategy problem. It has a courage problem. Everyone wants the opportunity, the deal, the leverage, and the big outcome, but very few people are willing to get on the plane, sit in the room, build the relationship, and take the risk before everything feels guaranteed.
Richard Baker is a real estate entrepreneur, dealmaker, founder of Baker House 1921, and longtime educator through Cornell’s Baker Program in Real Estate who has built one of the largest privately owned shopping center portfolios in the country. In this episode, he breaks down how he developed 50 Walmart-anchored shopping centers, bought Lord & Taylor for $1.2 billion, helped bring Target into Canada, and built a career by seeing value where other people saw problems.
We also talk about negotiation, using leverage without relying on cash, dealing directly with decision makers, manufacturing your own luck, and why the biggest players in the room are not always the smartest or fastest. Richard also explains why AI is going to create a massive wave of new entrepreneurs and how he personally uses it every morning to think, plan, and move faster.
If you have ever wondered what it really takes to think like an owner, create opportunity from nothing, and stop waiting for permission, this conversation will make you rethink business, risk, real estate, relationships, AI, and what entrepreneurship actually demands.
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.
Thank You to Our Sponsors!
Magic Mind: Head over to magicmind.com/jen and use code JEN at checkout.
Pique: Go to piquelife.com/jenniferrsd to get 20% off for life plus free gifts
Momentous: Ready to try supplements that actually do what they claim? Head to livemomentous.com and use code JEN for 35% off your first subscription.
Therasage: Visit therasage.com and use code JEN to get 15% off your order. Your skin
Prolon: Prolon is offering listeners 30% off sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit prolonlife.com/JENNIFERCOHEN and use code JENNIFERCOHEN to claim your discount and your bonus gift.
