The People Playbook with Jason Taylor
Better People Decisions. Stronger Teams. Scalable Results.
The People Playbook is your weekly guide to building high-performing teams and cultures that scale. Hosted by leadership coach and executive advisor Jason Taylor, this podcast features raw, insightful conversations with CEOs, founders, and culture builders who know what it really takes to lead in today’s world.
From mindset to execution, every episode unpacks the strategies, missteps, and breakthroughs behind exceptional leadership - and how to align your people, purpose, and performance for lasting impact.
Whether you're a CEO scaling fast, a senior leader navigating change, or a builder at heart - this is your playbook for becoming the leader your team needs.
🎯 New episodes weekly
🔥 Real talk. No fluff.
🧠 Actionable insights you can use today
Because growth doesn’t start with strategy - it starts with people.
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The People Playbook with Jason Taylor
Ryan Dymond, President & COO of FIKA Company - Building Trust, Hospitality-Led Cannabis Retail, and Leading Through Hyper-Growth
In this powerful episode of The People Playbook, Jason Taylor sits down with Ryan Dymond, President & COO of FIKA Company – one of Canada’s fastest-growing cannabis retail organizations with over 237 locations.
Ryan brings 25+ years of hospitality experience into the cannabis space and reveals how he’s flipped the traditional retail script: leading with genuine human connection instead of transactions, treating every guest interaction like a hospitality experience, and building a decentralized, trust-first culture that scales.
You’ll hear raw insights on:
- Why hospitality principles create deeper loyalty than discounts ever could
- How to shift from “manager” to “coach” with young frontline leaders
- The biggest mistakes leaders make during acquisitions (and how empathy prevents cultural disasters)
- Staying grounded and humble when everything is moving at lightning speed
- Why trust deposits/withdrawals and radical authenticity are non-negotiable
If you’re leading (or building) a high-growth team and believe culture eats strategy for breakfast, this conversation is pure gold. Ryan proves that people-first leadership isn’t just nice-to-have – it’s the ultimate competitive advantage.
[00:00] Introduction & Welcome
Jason welcomes Ryan Dymond, President & CEO of FIKA Company
[00:27] Ryan thanks Jason and shares gratitude for leading his team
[00:29] Jason on why the world needs better leaders and Ryan’s reputation
[01:17] What are the biggest cultural differences between hospitality and cannabis retail – and how do you carry leadership traits across industries?
Ryan contrasts high-energy hospitality with “sleepy” cannabis retail and explains FIKA’s hospitality-led, transformational (vs transactional) approach
[03:11] Creating meaningful connections and community through cannabis
[03:59] Trading short-term transactions for long-term trust and loyalty
[04:42] Jason and Ryan on trust + communication as the two pillars of culture
[05:47] Have you heard of “trust deposits and trust withdrawals”?
Ryan shares how they use the concept daily
[06:26] How did you shift your mindset from Director of Operations to President & CEO so quickly?
Ryan on humility, cross-functional alignment, and “creating the dots” for leaders to connect
[08:59] The real meaning of humility: “I don’t know it all and I need to learn more”
[09:23] Flattening hierarchy and rarely leading with title
[11:19] Story of a president who introduced himself as “I work with Jason”
[13:27] What leadership habits keep you grounded in the lightning-fast cannabis industry?
Agility, never forgetting your roots, celebrating wins but staying hungry
[15:57] Biggest mistakes leaders make when growing or acquiring multi-location teams – and how did you avoid them?
Lack of empathy, top-down change management, ego-driven standardization. Ryan explains FIKA’s “seek to understand first” acquisition philosophy
[20:22] How do you teach young, often first-job leaders to be coaches instead of bosses?
Empowerment, servant leadership, accelerated development plans, and failing forward
[24:19] If you could go back and give your 20-year-old self one piece of leadership advice, what would it be?
Lead with people first – they will always have your back. Ryan shares the emotional story of staff showing up unpaid to help him close a restaurant
[28:31] What are your two pieces of advice for young leaders today?
- Stay authentic – never wear a mask
- Outwork everyone, stay curious, and treat “no” as “not yet”
[31:06] Closing thanks and final thoughts on contagious leadership
