The Walker Webcast – October 16, 2025

Guest: Jonathan Goldstein, Co-Founder & CEO of Cain
Host: Willy Walker, CEO of Walker & Dunlop

Episode Overview

This episode features a wide-ranging conversation between Willy Walker and Jonathan Goldstein, a prominent British solicitor, entrepreneur, and the Chief Executive of real estate investment firm Cain. The discussion explores Jonathan's journey from law into real estate, his leadership philosophy, risk-taking, building luxury brands, the dynamics of hospitality, and his role as a director at Chelsea Football Club. While commercial real estate forms the backdrop, the episode is rich with personal reflections, insights on leadership, risk, humility, and the importance of values.

1. Jonathan’s Early Life & Motivations

Timestamp: 03:28 – 07:32

• Formative Experiences:

  • Jonathan attributes his intellectual curiosity and eventual drive to succeed primarily to the influence of his parents and his wife, Sharon, whom he met at university.
  • Academic focus came late: “I was always a smart kid, but focus and attention…was something that came later.” (03:37)
  • University experience was formative for his social and political engagement, with academics taking a back seat to other interests until post-graduate law prompted greater discipline.
  • Struggled to get into university due to low grade predictions; appreciated the transformation in education transparency over time.

• Influence of Family Values:

  • “They imbued in us a sense of confidence and a value system that has lived with me for the rest of my life.” (27:30)

2. Leadership Philosophy & Humility

Timestamp: 07:32 – 12:13

• Principles of Leadership:

  • Jonathan’s mantras: treat people as you want to be treated; risk hostility for the sake of leading; and maximize individual potential.
  • “To be a leader, you have to be prepared to risk hostility…stand your ground, make your opinion heard, but do so respectfully." (08:50)
  • He stresses the value of humility, communication, and creating environments where people can “maximize their potential” (10:50).
  • Consistent practice of these values across decades, from his earliest leadership roles.

• Memorable Quote:

  • “If you can create an environment in a business where people feel valued…and have an ability to express an opinion and not be disregarded…it gives you a real opportunity.” (11:20)

3. Career Transitions & Embracing Risk

Timestamp: 12:23 – 18:35

• Leaving Law for Real Estate:

  • Leaving Olswang (the law firm he led) was emotionally difficult but intellectually clear—he sought new challenges and fulfillment.
  • Needed support from close confidantes to “push over the wall” and take the leap.

• Thoughts on Entrepreneurship:

  • Prefers not to label himself an entrepreneur in the traditional sense and credits partners like Todd Boehly as world-class risk-takers.
  • “I'd been in the law for 15 years…from a very early age, I was always thinking about, you know, what was the next thing.” (17:15)

• Quote on Change:

  • “There’s two things: you feel unfulfilled…and you’re prepared to say ‘what’s the worst that could happen?’” (16:15)

4. Business vs. Politics: Leadership Contexts

Timestamp: 18:35 – 26:02

• Discussing Career Risk:

  • Conversation shifts to comparing business leadership with entering politics, referencing figures like Jim Collins and Tony Blair.
  • Challenges of moving between industries, especially into politics, are highlighted.
  • Admiration for politicians’ talent and capacity, regardless of party.

• Notable Quote:

  • “The ability to influence from the outside is sometimes more powerful than even…from the inside.” (19:33) – Goldstein

• Perspective on Real-World Experience:

  • “One of the big disconnects in the Western world…is that most of the world doesn't have people in government who actually have real life experience. They are just political geeks from the day they leave college.” (22:25)

5. Family, Values, and Risk Appetite

Timestamp: 26:02 – 29:40

• Origins of Risk-Taking:

  • Family business background in East London instilled strong values and confidence but not an explicit appetite for risk.
  • Risk appetite came from personal drive—“They imbued in us a sense of confidence and a value system that has lived with me for the rest of my life.” (27:30)

• On Being Grounded:

  • Goldstein stresses the importance of community, family, and a sense of responsibility as the foundation for taking calculated risks.

6. Enterprise & Major Deals at Cain

Timestamp: 29:40 – 38:01

• Project Analysis & Risk Management:

  • Approach to analyzing development risk: “At the time you make a decision…you've got to sit down and analyze it and cut it back.” (30:18)
  • Major projects like the Crown Building, 830 Brickell, and One Beverly Hills—focus on quality real estate as a way to calibrate downside.
  • Importance of focusing on strengths—“we should just stick in our lane and stay in what we are really, really good at.” (34:33)
  • Vision and partnerships (e.g., with Todd Boehly and Benny Alagem) made acquisitions like Beverly Hills possible.

• Unique Advantage in Beverly Hills:

  • Cain’s ability to transfer residential entitlements distinguished their bid for One Beverly Hills and created unique value.

• Memorable Detail:

  • “That was a massive, massive change for us…no one else could bring that to the table.” (36:45)

7. Building Luxury Brands: Amman, Delano, and the Luxury Segment

Timestamp: 38:01 – 44:50

• Focusing on Luxury:

  • Discussion about the surprising depth of the “premium luxury” customer base globally.
  • The Amangiri and Miami projects—luxury demand has soared post-COVID.

• Hospitality Execution:

  • Goldstein emphasizes operational involvement—sitting on boards, investing in brands to understand and influence guest experience.
  • “We want hotels that have soul. We want brands that have soul.” (43:17)
  • Importance of detail, innovation (e.g., hiring from Wynn for guest experience) and staying current: “Bringing a totally different perspective of thinking to our business.” (43:55)

8. Personalization, Service, and Hospitality Systems

Timestamp: 44:50 – 52:18

• The Power of Personal Touch:

  • Discussion about the challenge (and necessity) of institutionalizing personalization in hospitality at luxury level—learning from brands like Wynn, Ritz Carlton, and Four Seasons.
  • Memorable story about a personalized touch with a hamper at Four Seasons being systematized globally.

• Memorable Quote:

  • “If you invest in people, people will invest in you and they'll invest in your assets and they'll invest in the relationships that come along with that.” (49:44)

• On Brand Differentiation:

  • “Once you become a commodity, you lose your edge.” (51:56)

9. Football & Sports Team Ownership

Timestamp: 52:18 – 58:18

• Chelsea FC & Sports Investment:

  • Goldstein, a lifelong sports fan, describes how his partnership with Todd Boehly led to involvement with Chelsea FC and other sports franchises.
  • Acknowledges the responsibility of stewardship to supporter bases: “You are a custodian of the football club for your supporter base.” (59:23)
  • Lauds the success of Chelsea’s men’s and women’s teams; excitement for the brand’s future.

• The Intangibles of Ownership:

  • Not just about returns; unique, priceless experiences (e.g., ownership memories, championships) outstrip financial measurements.

10. Closing Reflections: Reputation, Ethics, and Impact

Timestamp: 58:18 – 61:52

• On Legacy & Humility:

  • Goldstein stresses that one’s reputation and how one treats others outweigh financial success.
  • “A good reputation is worth more than riches…people aren’t going to judge you by your scorecard at the end of the day.” (60:45)

• Final Words:

  • Willy: “We talked five minutes about real estate and 55 minutes about life lessons and how to lead and be a good person.”
  • Jonathan: “It’s been a pleasure.” (61:52)

Notable Quotes & Moments

• On Leadership and Risk:

  • “To be a leader, you have to be prepared to risk hostility.” – Jonathan Goldstein (08:45)
  • “Focus, focus, focus on detail…is one of the most important things in business.” (05:23)

• On Reputation and Ethics:

  • “A good reputation is worth more than riches.” (60:45)
  • “We're just a small speck in this world…but we can have an impact.” (58:55)

• On Hospitality:

  • “We want hotels that have soul. We want brands that have soul.” (43:17)

Key Takeaways

• The Power of Values: Jonathan credits much of his success to strong family values, community focus, and treating people well.
• Leadership is Personal: Creating environments that foster individual potential, humility, and respectful disagreement are core to his leadership.
• Risk is Calculated: Big career and business moves stemmed from careful analysis, confidence in personal and partnership capabilities, and an openness to growth.
• Luxury is About Experience: The future of hospitality lies in personalization and soulfulness; commoditization is the enemy of premium brands.
• Legacy Over Scorecard: Long-term impact, reputation, and ethical leadership are more important than financial metrics.

Summary Prepared for: Listeners seeking insights on leadership, risk, luxury real estate, and personal growth, straight from the candid, value-driven perspective of Jonathan Goldstein.