Loren Remillard never set out to be popular. A longtime civic leader and president and CEO of the Winnipeg Chamber of Commerce, he has learned that chasing approval—especially in an age obsessed with likes—undercuts clarity, integrity, and impact. What endures, he argues, is character: the daily discipline of doing the right thing, owning mistakes, and earning respect. Rooted in a 27-year marriage, years of camping and cottage weekends, and a commitment to raise children with a steady moral compass, Loren’s story centers on people over trophies and legacy over image.

In this candid conversation with host Teko Bailey, Loren traces the influences that shaped him—from resilient parents and a pioneering mother in business, to a school culture that demanded excellence and service. He opens up about being unemployed right before his wedding and how his wife’s unwavering respect reframed his sense of worth. He explains why he left a comfortable federal role to be more present for his young family, and later returned to the chamber to stretch and grow. Along the way, he shares hard-won frameworks: the “one thing” focus from City Slickers, a whitewater-rafting picture of when to paddle versus when to ride the current, and the difference between reputation (others’ perceptions) and character (who you are when you face the mirror).

Whether you’re navigating leadership scrutiny, wrestling with career tradeoffs, or trying to parent with presence in a digital world, this episode offers practical wisdom and grounded encouragement to run your own race—and to be respected by the right people, starting at home.

Major Themes & Concepts

• Respect over like: why popularity is a poor compass for leaders

• Character vs. reputation: what you can control and what you can’t

• Shaping moral compasses through time, presence, and the outdoors

• Career pivots for the right reasons: comfort as a silent risk

• Focus and mindfulness: choosing “the one thing” that matters now

• Resilience and gratitude: acknowledging luck while taking responsibility

• Education, service, and leaving fingerprints that last

• Handling criticism in public roles: clarity, transparency, and humility

• Practical parenting: channeling competitiveness into healthy goals

• Faith-inflected principles: purpose, legacy, and finishing the race well

Chapter Breakdown

00:00 – Navigating emotional well-being and the trap of chasing likes

01:58 – camping, cottages, and time over screens

04:26 – Building a moral compass that outlives titles

06:37 – Mark 8:36, City Slickers, and simple truths

09:24 – The “one thing”: focus, presence, and cutting through the noise

11:42 – Parents, education, and service-minded roots

18:21 – “Blessed to be a blessing”: creating value beyond yourself

21:09 – Worth beyond reputation: unemployment, marriage, and identity

23:54 – Choosing family and career wisely: leaving comfort to be present

27:43 – Character over reputation: leading amid critics and noise

30:56 – Raising healthy boys and avoiding CEO pitfalls

33:22 – Respect vs. like: a leadership stance for hard decisions

38:18 – A new chapter: run your race, keep the faith, and leave a legacy

About Teko Bailey

Teko Bailey is a husband, father, coach, and guide for men walking the path of faith and purpose. Through The Climb, he’s building a brotherhood of men committed to living fully, leading boldly, and climbing with intention.

Instagram: ⁠⁠⁠⁠⁠⁠⁠⁠@IamTekoBailey⁠⁠⁠⁠⁠⁠⁠⁠

Website: ⁠⁠⁠⁠⁠⁠⁠⁠tekobailey.com⁠⁠⁠⁠⁠⁠⁠⁠

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