Podcast Summary: Second in Command with Cameron Herold

Episode 537: Equiton Developments COO Christopher Wein – How EOS Drives Remarkable Calm in Rapid Growth
Guest: Christopher Wein (COO, Equiton Developments)
Host: Savannah Brewer (for Cameron Herold)
Date: December 18, 2025

Episode Overview

This episode features Christopher Wein, an accomplished real estate executive and the current COO of Equiton Developments. Christopher shares actionable insights on leading rapid growth in complex organizations, emphasizes the power of team chemistry, highlights the importance of effective systems, and delves into his productivity philosophies. A significant thread throughout is how the Entrepreneurial Operating System (EOS) underpins Equiton's ability to scale while maintaining remarkable calm and clarity.

Key Discussion Points & Insights

1. Equiton Developments: The Model and Mission

• Equiton is a private equity development firm that raises capital (over 18,000 investors, mainly in Canada) to build residential real estate (condos, townhomes, rentals) with returns funneled back to investors.
• Their holdings are focused primarily on the greater Toronto area—a region with sustained growth and strong long-term prospects.
• Investor Positioning: “We plan on building that and continuing to grow it over the next 25 years.” (03:54)

2. Christopher’s First 90 Days: Building a Foundation

• The “Three 30s” Approach:
  • First 30 days: Observe and absorb the culture and systems.
  • Next 30: Develop a strategy.
  • Final 30: Begin implementing change.
  • “...within 90 days I've actually come in, assessed, audited, and then made changes so that people can actually see true progress...” (11:25)
• Four Priorities upon Arrival:
  • Right Team Members: Evaluate and adjust team makeup for both skill and chemistry.
  • Vision: Collaboratively realign on vision—short, medium, and long-term.
  • Systems: Upgrade or replace systems for maximum efficiency.
  • Brand Alignment: Refine branding to match the company’s evolution.
  • “...having that team chemistry is the most important part of leadership.” (12:42–14:10)

3. Team Chemistry vs. Just Talent

• Chemistry as Core:
  • Good teams understand and support each other’s roles—akin to sports teams, where collective effort trumps individual star power. (15:52)
  • “...talented people can work together and that, you know, there's a chemistry and that there's a shared vision. And sometimes that isn't the case.” (12:53)
• Assessing Chemistry: Leaders need to “walk the floor,” listen, and observe informal interactions.

Memorable Analogy:

“The team that wins the tug of war is where everybody pulls with their own weight at the same time ... They don't need to be the strongest, they just have to pull in the same direction.” — Christopher Wein (17:28)

4. Letting People Go and Making Leadership Calls

• Active Sensing: Great leaders are attentive, perceptive, and present; they sense deeper current through informal observation. (18:24)
• Coachability: Some behaviors are changeable, especially early in someone’s career; ingrained habits are harder to shift later on.
• Ownership of Results: Focus is less on blame, more on solutions and improvement.

  “I don't really believe in wrong. What I believe in is continuous improvement.” (22:24)

• Positive Reinforcement: Behavior is shaped by highlighting positive outcomes over criticizing mistakes, both in business and in life. (24:17)

5. Crafting and Cascading Vision

• Leadership Sets the North Star: The executive team should define the high-level vision (the “30,000-ft view”), but the broader team should collaboratively build the operational roadmap to achieve it. (25:58–27:48)
• Ownership and Authenticity: Involvement in how the vision translates into action increases engagement and performance.

  “...if you explain to people where we want to go, but then let them decide for themselves how they’re going to take that journey, you get far better results...” (28:03)

6. Implementing and Choosing the Right Systems

• Systems as Tools:
  • “Is this system actually making your work easier?” is the core diagnostic question.
  • Replace systems/tools only when they’re clearly limiting productivity.
  • Avoid custom systems: “No one’s that special... IKEA uses the same accounting system that General Motors uses.” (38:00)
  • Leverage off-the-shelf robust tools, provide enough training, and develop “power users” to unlock advanced features.
• Simplicity and Focus: Layering more systems doesn’t equal more productivity; often, less (with deeper mastery) is more. (39:18–41:22)

7. The Rise of AI in Operations

• Christopher is an avid proponent of AI—applies it daily in both personal and professional contexts.

  “I use AI every day, and I use it, you know, in all aspects of my life...” (44:02)

• Adoption is akin to the early days of personal computers; those who embrace AI will gain an edge.

  “Every single living human being should understand the power of AI and should start using AI tools...” (45:10)

8. Productivity Philosophies and Personal Routines

• Extreme Productivity:
  • “I'm a big believer in multitasking ... but it takes training...” (48:58)
  • Early riser: Checks communications, reads news, then cycles 35 miles before work.
  • No lunch: Treats work as a sports match; all-in focus during work hours, true disconnection at day’s end.
  • Productivity comes from routine, clear focus, and compartmentalization—not from sporadic or diluted effort.
  • “When you’re at work and you’re trying to be productive, you’re in the field ... work as hard as you can, and then when you’re out, rest.” (51:30)

9. Leadership Mindset: Causing vs. Making Things Happen

• Causing is about subtly influencing outcomes and empowering others through indirect action, as opposed to overtly directing or micromanaging (“making”).

  “Causing things to happen is ... as a leader, using the power of suggestion, the power of influence, the power of opportunity to have people accomplish the things you want ... through their own volition.” (56:28)

  • Restaurant Analogy: You can wave for water (make it happen) or subtly place your empty glass forward and let service flow to you (cause it to happen).
  • More sustainable, more empowering, less confrontational; fosters initiative and growth in the team.

10. What’s Next: The Promise of AI and Human-Centric Leadership

• AI Evolution: Christopher is most excited about the rapid developments in AI and how it will unlock productivity, health, and well-being for people globally—across business, medicine, and daily life (approx. 62:24).
• Holistic Support for Teams: True performance comes when people are well in their own lives; he encourages leaders to support team mental and physical health as foundational to business results.

  “I need you to have the happiest possible out-of-work life you can, so that when you do show up on the field or on the court, you’re ready to go...” (64:14)

Notable Quotes & Memorable Moments

• On Team Ownership and Vision:

  “You can’t start with a blank piece of paper... You don’t want to bring in 25 people and say we have no vision... It’s sort of like when you get on a plane, you kind of want the pilot to have some indication of where planes go.” — Christopher Wein (26:09)

• On Custom Systems:

  “No one’s that special... IKEA uses the same accounting system that General Motors uses… So if those companies can use the same accounting software, why do we need to create custom software?” — Christopher Wein (38:00)

• On Leadership Responsibility:

  “People need to take responsibility for solutions and outcomes... I worry less about ‘you did this wrong’… What I believe in is continuous improvement.” (22:24)

• On Causing vs. Making:

  “When you cause things to happen, the temperature comes down, and it’s just this nice... And what's amazing is when you get really good at it, people will do things ... through their own volition.” (58:36)

Key Timestamps

• Introduction to Equiton & Model – 03:01
• First 90 Days & Priorities – 11:25
• Chemistry vs Talent – 14:10
• Letting People Go/Leadership Perception – 18:24
• Vision Crafting Philosophy – 25:58
• Systems Implementation – 33:54
• AI Adoption & Power Users – 44:02
• Productivity Routine – 48:58
• Causing vs. Making Things Happen – 56:28
• Looking Ahead/AI & Team Wellbeing – 62:18

Takeaways for COOs and Leaders

• Blend top-down vision with bottom-up empowerment—teams rally and perform when they help shape the path.
• Prioritize chemistry as much as capability; attention to team dynamics boosts performance and engagement.
• Embrace system simplicity and leverage off-the-shelf solutions; avoid reinventing the wheel.
• Adopt AI and foster in-house experts (“power users”) to drive up productivity.
• Invest in daily routines that maximize personal energy and focus.
• Use leadership influence to cause positive change rather than get stuck in direct control.
• Support your team personally as well as professionally for sustainable high performance.

Connect with Christopher Wein:

• Email: CWEIN@equiton.com
• LinkedIn: Christopher Wein

This episode delivers a blend of practical leadership wisdom and big-picture vision for COOs navigating growth and complexity in today’s business landscape.