Ep24 Grant Calder—From Limiting Beliefs to Leading Others: What Recovery Taught a Top Coach About Transformation

Diana Oehrli sits down with Grant Calder, founder of Fleet and her first coach over a decade ago, for a deeply personal conversation about the limiting beliefs that keep us stuck and the tools that set us free. Grant shares how a Tony Robbins fire walk shattered his belief that he was "too old and incapable" of pursuing an MBA... a moment that completely redirected his life toward coaching and leadership development. Diana reveals her own journey from feeling trapped in Gstaad and terrified of being alone to building a coaching practice and finding peace in solitude. Here's what you'll learn by listening to this full conversation: → How to identify the limiting beliefs secretly running your life... and the exact moment Grant realized his "best thinking" was what got him stuck in the first place → Why marble jar trust matters more than perfection... and how to rebuild connection after misalignment without destroying the relationship entirely → The daily refocus practice Grant's used for 15 years that helps him manage overwhelm without losing his mind (hint: it involves a floating digital post-it note) → How 25 years of sobriety gave Grant a "suitcase of tools" he now uses to coach leaders through fear, uncertainty, and the messy reality of entrepreneurship → What "half measures availed us nothing" actually means... and why going all-in doesn't require working yourself to death → The mindset mantras Grant relies on when outcomes slip beyond his control (including his favorite: "improvise, adapt, overcome, persist, march forward") Diana and Grant also explore the evolution of coaching itself... from skepticism 20 years ago to AI-assisted platforms today, and why human connection still can't be replaced by algorithms. Whether you're navigating privilege, building something new, or simply trying to get unstuck from a life everyone thinks you should be grateful for... this conversation offers practical wisdom wrapped in genuine friendship and mutual respect. Chapters (00:00:00) - The One Thing Every Entrepreneur Should Do(00:07:02) - In the Elevator With Grant(00:08:18) - How to Stop Limiting Belief(00:09:46) - The Secret to Developing Yourself(00:13:52) - The Need for Alignment in Relationships(00:15:52) - In the Elevator With Trust(00:22:24) - The Secret to 12 Step Recovery(00:26:41) - What patterns do you see in leadership from recovery?(00:30:12) - How to Manage Your Brain at Work(00:35:35) - How to Get Things Done: Developing a Mindset(00:41:05) - How to Scale Executive Coach Programs with Fleet(00:44:52) - What's the pricing for Coaching in the Elevator?(00:46:09) - How AI and Coaching are developing(00:51:51) - What do you think is the one thing entrepreneurs should do more than(00:57:06) - Who coaches you now?(00:59:08) - What's Your Morning Ritual?(01:00:36) - A Guest Interview with Diana on her Podcast(01:02:55) - How to Manage Your Wealth