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Second in Command: The Chief Behind the Chief with Cameron Herold

Ep. 537 - Equiton Developments COO Christopher Wein – How EOS Drives Remarkable Calm in Rapid Growth

Second in Command: The Chief Behind the Chief with Cameron Herold

Second in Command with Cameron Herold

Careers, Business, Management, Entrepreneurship

4.9 • 224 Ratings

🗓️ 18 December 2025

⏱️ 67 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Are you caught in the chaos of growth, struggling to build a team that actually wins together—not just on paper? In this unflinching episode, Sivana Brewer sits down with Christopher Wein, COO of Equiton Developments and a heavy-hitter in North American real estate, to crack open the mechanics of true team performance.

Discover why chemistry, not just talent, is the heart of unstoppable teams, how to identify toxic “A-players” before they destroy your culture, and the essential systems that cut out waste and ramp up productivity. Plus, get an inside look at how a real estate powerhouse harnesses AI, brand, and leadership psychology to fuel constant growth.

If you crave a more empowered team and want to sidestep the burnout and drama most operators face, you need to hear this conversation—right now. Wait, and you risk falling (further) behind leaders who are already applying these exclusive insights.

Timestamped Highlights

[00:00] – How chemistry—not talent—makes or breaks a winning team 

[05:00] – The “invisible” signals leaders use to spot misalignment early 

[11:25] – Wein’s ruthless approach to first-90-day change… and why waiting kills progress 

[16:48] – The surprising danger of superstar hires (and how to prevent toxicity) 

[26:38] – Crafting vision: where execs must dictate and where teams must own it 

[33:02] – What real productivity looks like—inside a COO’s hyper-productive day 

[40:17] – The tool myth: how misused systems actually crush company growth 

[53:46] – Revolutionary leadership: From “making” to “causing” results without the drama

Mentioned Resources


About the Guest

Christopher Wein is the Chief Operating Officer of Equiton Developments, a private equity real estate firm with 18,000 investors and a national development portfolio. Known for over 25 years of operational leadership across Canada and the United States, Wein is an industry innovator in sustainable building and high-performing leadership teams. He’s received top honors, including Calgary’s Top 40 Under 40 and the King Charles III Coronation Medal for philanthropy. Connect with Christopher for proven wisdom on team scale, chemistry, and vision-driven operations.

🔗 LinkedIn | Website

About the Co-Host

Sivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.

🔗 Connect with Sivana on LinkedIn

Important Links



The Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Transcript

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0:00.0

I prefer a larger team.

0:02.4

But what I think what happens with a larger team, it's sort of a two-part answer.

0:07.9

So the initial vision, the initial direction should come from leadership, so from executive

0:14.3

leadership.

0:15.1

So when I'm looking at the vision of Equiton developments, I'm initially thinking, okay,

0:23.3

this is where I believe we should go and this is how we should position ourselves at a very, very high level, like 30,000 feet.

0:28.3

And as soon as I have that, I want to then bring in the team to be like, okay, this is what I'm

0:34.1

thinking, but this is very, you know, 30,000 foot.

0:38.6

Let's now dig into this as a team collectively so that everybody feels like they take

0:43.9

ownership of the vision and everybody's had a part of it.

0:50.9

Welcome to the Second and Command podcast, produced by the CO Alliance and brought to you by its founder, Cameron Harold.

0:58.9

In the Second in Command podcast, we talked to top COOs who share the insights, strategies, and tactics that made them the chief behind the chief.

1:07.3

And now here's your co-host, former CEOO of a multi-eight-figure remote company

1:12.5

and alumni member of the COO Alliance, Savannah Brewer. Our guest today is Christopher Wine,

1:22.1

COO of Equiton Developments, a seasoned real estate leader with over 25 years of experience across

1:28.5

Canada and the U.S., leaving projects from master plan communities to skyscrapers.

1:34.8

Beyond his impressive operational expertise, Christopher is a recognized innovator in sustainable

1:39.4

building solutions and a passionate contributor to Canadian philanthropy, earning honors like the King Charles

1:45.6

the Third for a nation medal, and he's also on Calgary's top 40 under 40 list. On today's episode,

1:52.6

we dive into what it takes to build the right team chemistry, Christopher's philosophy for putting the right

1:57.6

systems in place, and why having a true power player on your team can transform your business.

2:03.5

We also explore his views on productivity and what it means to play all out in both leadership and life.

...

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