Retreats & Offsites Unpacked

How Friction During Offsites Is a Good Thing

Is friction during an offsite a problem — or a signal that something important is happening? In this episode, Dan Berger sits down with Adam Silberstein, a YPO Certified Forum Facilitator and executive coach, to unpack why tension inside peer groups and leadership teams is often the gateway to creativity. Adam shares what nearly 20 years of facilitation has taught him about mastery, onboarding forums correctly, accountability gaps inside peer groups, and why artificial harmony is more dangerous than productive conflict. They dive into Forum Operating Systems (FOS), guiding principles, growth commitments, coaching models, and the role of nature in retreat design. If you lead offsites, moderate forums, or design leadership retreats — this episode reframes friction as fuel. Episode Themes * Why friction is creative energy * Artificial harmony vs productive storming * The “10–12 common issues” every forum faces * Onboarding forums the right way * Forum Operating System (FOS) thinking * Growth areas and guiding principles * Coaching vs consulting vs facilitating * Using nature to elevate retreat outcomes * Trust as the currency of facilitation Chapters 00:00 – Introduction 01:32 – Mastery after 10,000 hours 03:23 – Discovering what the room needs 05:27 – Common forum dysfunction 06:15 – Why friction is creative energy 07:41 – The calling into facilitation 10:29 – The Adam playbook 13:01 – Forum Operating System (FOS) 16:56 – Coaching models and transitions 19:02 – Designing powerful retreat spaces 21:10 – Fees and pricing transparency 23:34 – Client retention and trust 26:15 – The ancient power of peer groups About the Guest Adam Silberstein is a YPO Certified Forum Facilitator and executive coach who began facilitating at 26 after early mentorship under Jim Warner. Over nearly two decades, he has worked with thousands of executives, teams, and families across YPO and EO, specializing in forum retreats, leadership offsites, and CEO coaching. Website: adamsilberstein.com [https://www.adamsilberstein.com/] About the Assemble Podcast Welcome to the Assemble Podcast. I’m Dan Berger, founder of Assemble Hospitality Group. We build purpose-designed spaces for small team offsites and retreats, because the biggest things happen in the smallest rooms. This show explores retreats in all forms—corporate, lifestyle, wellness, and endurance training—and the culture shifts that happen when people step away from the everyday. You’ll hear lessons from operators, facilitators, and leaders who design experiences that move the needle. Our goal: give you the playbook for building clarity, trust, and belonging on your team—or in your community. Learn more: assemblehospitality.com [https://assemblehospitality.com/] Social Media: Facebook [https://www.facebook.com/assemblehospitality/] | Instagram [https://instagram.com/assembleboise] | LinkedIn [https://www.linkedin.com/company/assemble-retreats/] | YouTube [https://www.youtube.com/@assemble-hospitality] Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality [https://assemblehospitality.com/]. Recorded at Assemble’s Boise Retreat House. Produced by KazCM [https://kazcm.com/], part of the QuietLoud Studios [https://quietloudstudios.com/] podcast network. Distributed on SportsEpreneur [https://sportsepreneur.com/].

How to Create a Men’s Group

What does it actually take to start a men’s group that lasts? In this episode, Dan Berger sits down with Tony Delmercado and Kris Derentz — co-chairs of Fellows & Fire Pits — to unpack how a small backyard gathering evolved into a thriving men’s community. This conversation isn’t about theory. It’s about structure, participation, leadership, exclusivity, accountability, and the unglamorous early push required to get something like this off the ground. They cover everything from heart warmers and group chats to membership criteria, vibe checks, and why men especially need intentional space as they get older. If you’ve ever thought about starting a men’s group — or strengthening one you’re already part of — this episode gives you the real blueprint. Episode Themes * Why men need structured connection * Lower barrier to entry, higher barrier to retention * The power of conscious exclusivity * Designing agendas that drive depth * Heart warmers vs surface-level icebreakers * Participation as the core success metric * Leadership without hierarchy * Referral, vibe checks, and protecting culture * Why momentum matters early on Chapters 00:00 – Introduction 01:20 – What Fellows & Fire Pits is 02:07 – What makes a good member 04:04 – Heart warmers and vulnerability 06:06 – Anatomy of a great meeting 07:55 – When members get asked to leave 09:27 – Events and cadence 11:01 – Ideal group size 12:54 – Conscious exclusivity 14:18 – Why men need spaces like this 18:22 – Advice for starting your own group 21:16 – Leadership structure 24:06 – Belonging and accountability 27:13 – Final thoughts About the Guests Tony Delmercado is Founder & CEO of Hawk Media and co-chair of Fellows & Fire Pits, a men’s group focused on authenticity, connection, and growth. Kris Derentz is Founder & CEO of EquippedMD and co-chair of Fellows & Fire Pits, where he helps steward membership, culture, and participation. Website: firepitmensgroup.com [https://firepitmensgroup.com/] About the Assemble Podcast Welcome to the Assemble Podcast. I’m Dan Berger, founder of Assemble Hospitality Group. We build purpose-designed spaces for small team offsites and retreats, because the biggest things happen in the smallest rooms. This show explores retreats in all forms—corporate, lifestyle, wellness, and endurance training—and the culture shifts that happen when people step away from the everyday. You’ll hear lessons from operators, facilitators, and leaders who design experiences that move the needle. Our goal: give you the playbook for building clarity, trust, and belonging on your team—or in your community. Learn more: assemblehospitality.com [https://assemblehospitality.com/] Social Media: Facebook [https://www.facebook.com/assemblehospitality/] | Instagram [https://instagram.com/assembleboise] | LinkedIn [https://www.linkedin.com/company/assemble-retreats/] | YouTube [https://www.youtube.com/@assemble-hospitality] Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality [https://assemblehospitality.com/]. Recorded at Assemble’s Boise Retreat House. Produced by KazCM [https://kazcm.com/], part of the QuietLoud Studios [https://quietloudstudios.com/] podcast network. Distributed on SportsEpreneur [https://sportsepreneur.com/].

What Retreat Leaders Can Learn From a Brother and Sister Team

What happens when facilitation runs in the family? In this episode, Dan Berger sits down with siblings Kaley Klemp and Paul Warner to explore what retreat leaders can learn from working inside a family system — and what it takes to build trust, credibility, and mastery across generations. As second-generation facilitators, Kaley and Paul share how mentorship shaped their careers, how they developed their own voices apart from their father’s legacy, and why shadowing, apprenticeship, and doing your own personal work are non-negotiables in this field. The conversation moves from sibling dynamics to small-group mastery, business development, referral networks, and the difference between “soft skills” and real strategic execution. If you’re building a facilitation practice — or thinking about entering the space — this episode is a masterclass in craft, humility, and long-game thinking. Episode Themes * What siblings can teach retreat leaders about collaboration * Second-generation facilitation and finding your own voice * The power of shadowing and apprenticeship * Small groups as the training ground for facilitators * Tools like issue clearing, reflective listening, and the Enneagram * Why facilitators must keep doing their own work * How referrals actually work in this industry * Blending relational work with hard strategy * Mentorship and building credibility over time Chapters 00:00 – Welcome and introductions 02:08 – Sibling dynamics in facilitation 04:00 – Growing up with a facilitator father 06:00 – Finding your own voice in the field 06:43 – Early facilitation experiences 08:59 – Advice for aspiring facilitators 10:18 – Working with families 12:28 – Why continual self-work matters 14:02 – Favorite facilitation tools 17:18 – Reflective listening and plexiglass 18:02 – Facilitator camp explained 20:59 – Mentorship in this field 22:30 – Business development and referrals 24:09 – How facilitators choose who to refer 26:44 – Blending strategy with interpersonal work 29:10 – What wasn’t asked About the Guests Kaley Klemp is an expert in small-group dynamics and leadership development who has facilitated retreats and trainings worldwide since 2004. She helps executives and teams strengthen communication, resolve conflict, and foster trust so they can achieve shared objectives. Her work blends strategic clarity with deep relational insight. Website: kaleyklemp.com [https://kaleyklemp.com/]Social Media: LinkedIn [https://www.linkedin.com/in/kaley-klemp-5483b418/] Paul Warner is a facilitator and coach who works with executive teams, YPO forums, and families to foster transparency, trust, and authentic connection. Through experiential retreats and coaching, he helps participants navigate difficult conversations and strengthen adult-to-adult relationships. Website: thepaulwarnergroup.com [https://www.thepaulwarnergroup.com/]Social Media: LinkedIn [https://www.linkedin.com/in/paul-warner-a6943518/] About the Assemble Podcast Welcome to the Assemble Podcast. I’m Dan Berger, founder of Assemble Hospitality Group. We build purpose-designed spaces for small team offsites and retreats, because the biggest things happen in the smallest rooms. This show explores retreats in all forms—corporate, lifestyle, wellness, and endurance training—and the culture shifts that happen when people step away from the everyday. You’ll hear lessons from operators, facilitators, and leaders who design experiences that move the needle. Our goal: give you the playbook for building clarity, trust, and belonging on your team—or in your community. Learn more: assemblehospitality.com [https://assemblehospitality.com/] Social Media: Facebook [https://www.facebook.com/assemblehospitality/] | Instagram [https://instagram.com/assembleboise] | LinkedIn [https://www.linkedin.com/company/assemble-retreats/] | YouTube [https://www.youtube.com/@assemble-hospitality] Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality [https://assemblehospitality.com/]. Recorded at Assemble’s Boise Retreat House. Produced by KazCM [https://kazcm.com/], part of the QuietLoud Studios [https://quietloudstudios.com/] podcast network. Distributed on SportsEpreneur [https://sportsepreneur.com/].

Why Co-Hosts Make Retreats Better

What changes when a retreat is led by a team instead of a single facilitator? Many retreats rely on one voice, one lens, and one nervous system to hold the room. But when retreats are co-hosted, something different happens: the container deepens, participants feel more supported, and transformation becomes shared rather than hierarchical. In this episode, Dan Berger is joined by Christina Courtright Jenkins, April Millar, and Aleena Hill—co-founders of The Wise Woman World—to unpack why co-hosting retreats can dramatically improve safety, depth, and long-term impact. The conversation explores shared leadership, feminine containers, astrology-informed personalization, nervous-system regulation, and how multiple facilitators create resilience not just for participants—but for the facilitators themselves. Episode Themes * Why co-hosted retreats create stronger containers * Shared power vs. hierarchy in facilitation * The role of feminine energy and cyclical rhythms * Personalization at scale through astrology and somatics * Nervous-system safety as the foundation for intuition * Pre-retreat preparation and energetic investment * Post-retreat community and integration * Choosing the right co-hosts and complementary roles Chapters 00:00 – Welcome and introduction 01:18 – What Wise Woman World actually does 02:17 – Who these retreats are for 03:39 – Feminine cycles and life stages 05:16 – Masculine vs. feminine energy 06:59 – Being held and fully taken care of 07:30 – Personalization through astrology 09:23 – What facilitators experience during retreats 11:29 – Pricing, value, and transformation 14:15 – Astrology as meaning-making, not prediction 17:55 – Marketing retreats through word of mouth 19:54 – Why co-hosts multiply impact 21:27 – Post-retreat community and continuity 23:51 – Defining roles within a facilitation team 24:38 – What to look for in a co-host 26:25 – Nervous system healing and intuition 29:54 – Advice for new retreat organizers 31:00 – Where to learn more About the Guests – The Wise Woman World Founders Christina Courtright Jenkins, April Millar, and Aleena Hill are the co-founders of The Wise Woman World, a heart-centered collective devoted to embodiment, transformation, and living in sacred rhythm with the body and the earth. Their retreats integrate astrology, somatic practices, nervous-system healing, intuitive guidance, and shared leadership. Working through a non-hierarchical model, they create deeply personalized experiences where women feel seen, supported, and safely held—often for the first time in years. Website: thewisewomanworld.com [https://www.thewisewomanworld.com/]Social Media: Facebook [https://www.facebook.com/WorkWithTheMoon] | Instagram [https://www.instagram.com/the.wise.woman.world] | TikTok [https://www.tiktok.com/@the.wise.woman.world] | YouTube [https://www.youtube.com/@thewisewomanworld] About the Assemble Podcast Welcome to the Assemble Podcast. I’m Dan Berger, founder of Assemble Hospitality Group. We build purpose-designed spaces for small team offsites and retreats, because the biggest things happen in the smallest rooms. This show explores retreats in all forms—corporate, lifestyle, wellness, and endurance training—and the culture shifts that happen when people step away from the everyday. You’ll hear lessons from operators, facilitators, and leaders who design experiences that move the needle. Our goal: give you the playbook for building clarity, trust, and belonging on your team—or in your community. Learn more: assemblehospitality.com [https://assemblehospitality.com/] Social Media: Facebook [https://www.facebook.com/assemblehospitality/] | Instagram [https://instagram.com/assembleboise] | LinkedIn [https://www.linkedin.com/company/assemble-retreats/] | YouTube [https://www.youtube.com/@assemble-hospitality] Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality [https://assemblehospitality.com/]. Recorded at Assemble’s Boise Retreat House. Produced by KazCM [https://kazcm.com/], part of the QuietLoud Studios [https://quietloudstudios.com/] podcast network. Distributed on SportsEpreneur [https://sportsepreneur.com/].

How Planning a Retreat Is Like Making a Film

What if designing a retreat required the same level of intention as producing a great film? The most powerful retreats don’t happen by accident. Like films, they’re carefully designed experiences with a beginning, middle, and end—crafted to move people emotionally, not just impress them logistically. In this episode, Dan Berger speaks with Sean Buckley, CEO of Buck Productions, to explore the surprising parallels between retreat planning and filmmaking with an award-winning producer whose work spans unscripted television, documentaries, and feature films. Through the lens of Project Guatemala, the conversation unpacks how story, audience, environment, and shared challenge combine to create experiences that genuinely transform people. The discussion reframes retreats as immersive narratives—where participants leave their normal lives behind, step into discomfort, build community, and walk away with a story they’ll carry long after the retreat ends. Episode Themes * Why retreats and films share the same narrative structure * Designing experiences with a clear beginning, middle, and end * Audience-first thinking in retreat planning * Discomfort and challenge as catalysts for transformation * Creating shared meaning through collective experience * The role of environment in emotional impact * Post-retreat integration and lasting connection * Story as the takeaway participants carry forward Chapters 00:00 – Welcome and introduction 01:20 – Introducing Project Guatemala 02:21 – Chaos, luxury, and the turning point 05:12 – Discomfort as the start of transformation 08:06 – Why this experience qualifies as a retreat 11:14 – Six weeks vs. lifelong impact 14:33 – Interventions, breakdowns, and growth 17:26 – Community after the retreat ends 19:28 – Why storytelling matters in retreats 20:57 – Audience-first design 23:06 – Films and retreats as shared journeys 23:59 – Closing reflections About the Guest – Sean Buckley Sean Buckley is the CEO of Buck Productions and an award-winning producer with more than 30 years of experience in unscripted television, documentaries, branded content, and feature films. His work is known for pushing creative boundaries while centering deeply human stories. Through large-scale productions and purpose-driven projects, Sean has helped shape experiences that challenge people emotionally, physically, and ethically. His perspective brings a rare storytelling lens to retreat design—highlighting how narrative, audience awareness, and intentional structure can turn moments into meaning. Website: buckproductions.com [https://buckproductions.com/]Social Media: Facebook [https://www.facebook.com/buckproductions/] | Instagram [https://www.instagram.com/buckproductions/] | LinkedIn [https://www.linkedin.com/in/sean-buckley-93119b7/] About the Assemble Podcast Welcome to the Assemble Podcast. I’m Dan Berger, founder of Assemble Hospitality Group. We build purpose-designed spaces for small team offsites and retreats, because the biggest things happen in the smallest rooms. This show explores retreats in all forms—corporate, lifestyle, wellness, and endurance training—and the culture shifts that happen when people step away from the everyday. You’ll hear lessons from operators, facilitators, and leaders who design experiences that move the needle. Our goal: give you the playbook for building clarity, trust, and belonging on your team—or in your community. Learn more: assemblehospitality.com [https://assemblehospitality.com/] Social Media: Facebook [https://www.facebook.com/assemblehospitality/] | Instagram [https://instagram.com/assembleboise] | LinkedIn [https://www.linkedin.com/company/assemble-retreats/] | YouTube [https://www.youtube.com/@assemble-hospitality] Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality [https://assemblehospitality.com/]. Recorded at Assemble’s Boise Retreat House. Produced by KazCM [https://kazcm.com/], part of the QuietLoud Studios [https://quietloudstudios.com/] podcast network. Distributed on SportsEpreneur [https://sportsepreneur.com/].