Retreats & Offsites Unpacked

Assemble Hospitality Group
  • 4.9 (13)
  • Management

Retreats & Offsites Unpacked by Assemble Hospitality is about what happens when people step away together and find a deeper sense of belonging. We share stories and best practices from retreats and offsites to explore how intentional gatherings create change.

  1. May 6

    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 energyArtificial harmony vs productive stormingThe “10–12 common issues” every forum facesOnboarding forums the right wayForum Operating System (FOS) thinkingGrowth areas and guiding principlesCoaching vs consulting vs facilitatingUsing nature to elevate retreat outcomesTrust as the currency of facilitation Chapters 00:00 – Introduction01:32 – Mastery after 10,000 hours03:23 – Discovering what the room needs05:27 – Common forum dysfunction06:15 – Why friction is creative energy07:41 – The calling into facilitation10:29 – The Adam playbook13:01 – Forum Operating System (FOS)16:56 – Coaching models and transitions19:02 – Designing powerful retreat spaces21:10 – Fees and pricing transparency23:34 – Client retention and trust26:15 – The ancient power of peer groups About the GuestAdam 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 About the Assemble PodcastWelcome 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 Social Media: Facebook | Instagram | LinkedIn | YouTube Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality. Recorded at Assemble’s Boise Retreat House. Produced by KazCM, part of the QuietLoud Studios podcast network. Distributed on SportsEpreneur.

    31 min

  2. Apr 29

    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 connectionLower barrier to entry, higher barrier to retentionThe power of conscious exclusivityDesigning agendas that drive depthHeart warmers vs surface-level icebreakersParticipation as the core success metricLeadership without hierarchyReferral, vibe checks, and protecting cultureWhy momentum matters early onChapters00:00 – Introduction01:20 – What Fellows & Fire Pits is02:07 – What makes a good member04:04 – Heart warmers and vulnerability06:06 – Anatomy of a great meeting07:55 – When members get asked to leave09:27 – Events and cadence11:01 – Ideal group size12:54 – Conscious exclusivity14:18 – Why men need spaces like this18:22 – Advice for starting your own group21:16 – Leadership structure24:06 – Belonging and accountability27:13 – Final thoughts About the GuestsTony 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 About the Assemble PodcastWelcome 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 Social Media: Facebook | Instagram | LinkedIn | YouTube Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality. Recorded at Assemble’s Boise Retreat House. Produced by KazCM, part of the QuietLoud Studios podcast network. Distributed on SportsEpreneur.

    28 min

  3. Apr 22

    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 collaborationSecond-generation facilitation and finding your own voiceThe power of shadowing and apprenticeshipSmall groups as the training ground for facilitatorsTools like issue clearing, reflective listening, and the EnneagramWhy facilitators must keep doing their own workHow referrals actually work in this industryBlending relational work with hard strategyMentorship and building credibility over time Chapters00:00 – Welcome and introductions02:08 – Sibling dynamics in facilitation04:00 – Growing up with a facilitator father06:00 – Finding your own voice in the field06:43 – Early facilitation experiences08:59 – Advice for aspiring facilitators10:18 – Working with families12:28 – Why continual self-work matters14:02 – Favorite facilitation tools17:18 – Reflective listening and plexiglass18:02 – Facilitator camp explained20:59 – Mentorship in this field22:30 – Business development and referrals24:09 – How facilitators choose who to refer26:44 – Blending strategy with interpersonal work29:10 – What wasn’t asked About the GuestsKaley 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.comSocial Media: LinkedIn 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.comSocial Media: LinkedIn About the Assemble PodcastWelcome 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 Social Media: Facebook | Instagram | LinkedIn | YouTube Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality. Recorded at Assemble’s Boise Retreat House. Produced by KazCM, part of the QuietLoud Studios podcast network. Distributed on SportsEpreneur.

    31 min

  4. Apr 15

    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 containersShared power vs. hierarchy in facilitationThe role of feminine energy and cyclical rhythmsPersonalization at scale through astrology and somaticsNervous-system safety as the foundation for intuitionPre-retreat preparation and energetic investmentPost-retreat community and integrationChoosing the right co-hosts and complementary rolesChapters 00:00 – Welcome and introduction01:18 – What Wise Woman World actually does02:17 – Who these retreats are for03:39 – Feminine cycles and life stages05:16 – Masculine vs. feminine energy06:59 – Being held and fully taken care of07:30 – Personalization through astrology09:23 – What facilitators experience during retreats11:29 – Pricing, value, and transformation14:15 – Astrology as meaning-making, not prediction17:55 – Marketing retreats through word of mouth19:54 – Why co-hosts multiply impact21:27 – Post-retreat community and continuity23:51 – Defining roles within a facilitation team24:38 – What to look for in a co-host26:25 – Nervous system healing and intuition29:54 – Advice for new retreat organizers31:00 – Where to learn more About the Guests – The Wise Woman World FoundersChristina 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.comSocial Media: Facebook | Instagram | TikTok | YouTube About the Assemble PodcastWelcome 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 Social Media: Facebook | Instagram | LinkedIn | YouTube Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality. Recorded at Assemble’s Boise Retreat House. Produced by KazCM, part of the QuietLoud Studios podcast network. Distributed on SportsEpreneur.

    31 min

  5. Apr 9

    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 structureDesigning experiences with a clear beginning, middle, and endAudience-first thinking in retreat planningDiscomfort and challenge as catalysts for transformationCreating shared meaning through collective experienceThe role of environment in emotional impactPost-retreat integration and lasting connectionStory as the takeaway participants carry forwardChapters00:00 – Welcome and introduction01:20 – Introducing Project Guatemala02:21 – Chaos, luxury, and the turning point05:12 – Discomfort as the start of transformation08:06 – Why this experience qualifies as a retreat11:14 – Six weeks vs. lifelong impact14:33 – Interventions, breakdowns, and growth17:26 – Community after the retreat ends19:28 – Why storytelling matters in retreats20:57 – Audience-first design23:06 – Films and retreats as shared journeys23:59 – Closing reflections About the Guest – Sean BuckleySean 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.comSocial Media: Facebook | Instagram | LinkedIn About the Assemble PodcastWelcome 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 Social Media: Facebook | Instagram | LinkedIn | YouTube Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality. Recorded at Assemble’s Boise Retreat House. Produced by KazCM, part of the QuietLoud Studios podcast network. Distributed on SportsEpreneur.

    25 min

  6. Apr 1

    How to Organize Transformational Retreats for Women

    What actually makes a women’s retreat transformational—and not just a beautiful escape? Transformation doesn’t come from the location alone. It happens when people slow down, regulate their nervous systems, and feel safe enough to let go of urgency, perfectionism, and performance. In this episode, Dan Berger speaks with Kelley Hartman, founder of Wild Harts Collective, about how transformational retreats for women are intentionally designed—from nervous-system work and creative expression to nature-based ritual and integration. Drawing on more than 20 years of corporate leadership experience, the conversation explores the shift from burnout to sovereignty, how small-group retreats create safety and depth, and why creativity and joy are essential—not optional—ingredients in meaningful retreat experiences. Episode Themes What differentiates transformational retreats from getawaysNervous-system regulation as the foundation for changeLetting go of urgency, burnout, and perfectionismCreative expression as an access point to embodimentDesigning retreats that balance structure and flowWhy small groups foster deeper trust and safetyRelationship-based approaches to marketing retreatsSupporting integration after the retreat endsChapters 00:00 – Welcome and introduction01:40 – The retreat experience that changed everything03:22 – From corporate leadership to retreat creation05:09 – Failing forward and nervous-system regulation06:43 – Stillness, sovereignty, and pattern awareness08:12 – One-on-one work and post-retreat integration08:37 – Retreat size, pricing, and audience09:38 – Finding participants through community11:12 – Transformation stories from retreats14:12 – Nature-based rituals and somatic practices16:06 – Creative expression and painting joy17:47 – Expanding retreats and future plans19:55 – Advice for aspiring retreat leaders21:48 – Who these retreats are for and closing thoughts About the Guest – Kelley Hartman Kelley Hartman is the founder of Wild Harts Collective and a former corporate leader turned retreat creator. With over two decades of leadership experience, she designs transformational retreats that blend nervous-system regulation, creative expression, and nature-based ritual. Her work supports women—often high-performing and burned out—in reconnecting with joy, sovereignty, and embodied presence. Through small-group retreats, coaching, and experiential practices, she helps participants move beyond “shoulds” and build lives that feel aligned, regulated, and expansive. Website: wildhartscollective.com Social Media: Instagram | LinkedIn 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 Social Media: Facebook | Instagram | LinkedIn | YouTube Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality. Recorded at Assemble’s Boise Retreat House. Produced by KazCM, part of the QuietLoud Studios podcast network. Distributed on SportsEpreneur.

    23 min

  7. Mar 25

    What Does Family Therapy Have to Do With Retreats?

    What if the real work of retreats isn’t strategy or skills—but relationships? Many retreats struggle not because of poor agendas, but because of unspoken dynamics, unmet attachment needs, and a lack of psychological safety inside the group. In this episode, Dan Berger is joined by Patience Shutts, a retreat facilitator, keynote speaker, and licensed marriage and family therapist, to explore how family systems thinking can radically improve retreat and forum outcomes. The conversation unpacks why belonging is a felt, somatic experience—not an intellectual one—how facilitators can co-regulate groups, and why deep listening, shared agreements, and vulnerability are the real drivers of trust and transformation in retreat settings. Episode Themes Why retreats are fundamentally relational systemsFamily systems theory applied to forums and retreatsBelonging as a somatic, nervous-system experiencePsychological safety and attachment needs in groupsFacilitators as co-regulators of the roomTeaching vs. facilitating—and when to do eachVulnerability, credibility, and leading by exampleHow shared agreements shape healthy group cultureChapters 00:00 – Welcome and introduction01:36 – The story behind the name “Patience”03:04 – What makes facilitation truly effective04:58 – Systems thinking and group dynamics08:13 – Teaching vs. facilitating in retreats08:44 – Forums, families, and relational systems11:39 – What belonging really feels like15:35 – Vulnerability and facilitator credibility16:42 – Co-regulating a group as a facilitator19:32 – Choosing the right facilitator fit23:24 – How family therapy informs retreat work27:25 – Final reflections and closing About the Guest – Patience ShuttsPatience Shutts is a retreat facilitator, keynote speaker, and licensed marriage and family therapist who blends human development, attachment theory, interpersonal neurobiology, and systems psychology. With thousands of clinical hours and global field experience, her work focuses on helping leaders and groups build emotional intelligence, belonging, and relational health. Patience has supported leaders and organizations across the world, including work with trauma survivors, executive forums, and alumni communities. Her facilitation style emphasizes embodied presence, deep listening, and the belief that meaningful growth happens best in relationship with others. Website: patienceshutts.com Social Media: Instagram | LinkedIn About the Assemble PodcastWelcome 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 Social Media: Facebook | Instagram | LinkedIn | YouTube Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality. Recorded at Assemble’s Boise Retreat House. Produced by KazCM, part of the QuietLoud Studios podcast network. Distributed on SportsEpreneur.

    28 min

  8. Mar 18

    The Details Behind Neotantric Retreats

    What actually happens inside a neotantric retreat—and why do people travel across the world to attend them? Neotantric retreats sit at the intersection of intimacy, nervous-system regulation, embodiment, and personal growth—yet they’re often misunderstood or oversimplified. In this episode, Dan Berger sits down with Dawn Cartwright, founder of the Chandra Bindu Tantra Institute, to unpack what neotantric retreats truly involve, how they’re designed, and why safety, structure, and presence matter just as much as vulnerability. The conversation explores tantra versus neo-tantra, how sexuality relates to flow states and leadership, and what retreat leaders must consider when facilitating deeply personal work in a group setting—without crossing boundaries or losing trust. Episode Themes Tantra vs. neo-tantra: ancient roots and modern applicationSexuality as a pathway to flow, creativity, and leadershipShame, control, and the challenge of receivingCreating psychological safety in intimate group retreatsDesigning neotantric retreats with structure and consentSomatic practices that build sensitivity and presenceWhy ritual matters in lasting transformationRetreat environments that support intimacy and trustChapters00:00 – Welcome and introduction01:40 – Why sexuality still feels taboo03:23 – Shame, success, and delayed pleasure05:41 – Sex, flow states, and peak performance06:59 – Tantra vs. neo-tantra explained10:13 – Belonging, control, and mutual presence12:26 – Creating safety in intimate group settings14:40 – What a neotantric retreat actually looks like17:34 – Integration, aftereffects, and long-term change19:23 – Inclusivity, pricing, and group size21:59 – Designing spaces for intimacy and privacy25:43 – What tantric sex really means About the Guest – Dawn CartwrightDawn Cartwright is a tantric visionary, sacred writer, and teacher with more than three decades of study across classical and modern tantric traditions. She integrates ancient tantra, bioenergetics, psychology, and somatic practices to support embodied intimacy and human potential. As founder of the Chandra Bindu Tantra Institute, Dawn leads retreats and trainings around the world focused on presence, connection, and relational mastery. Her work emphasizes safety, consent, and practical integration—bringing esoteric teachings into modern relationships and daily life. Website: Chandra Bindu Tantra InstituteSocial Media: Facebook | X | Instagram | LinkedIn About the Assemble PodcastWelcome 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 Social Media: Facebook | Instagram | LinkedIn | YouTube Credits: Hosted by Dan Berger, Founder & CEO of Assemble Hospitality. Recorded at Assemble’s Boise Retreat House. Produced by KazCM, part of the QuietLoud Studios podcast network. Distributed on SportsEpreneur.

    26 min
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4.9
out of 5
13 Ratings

About

Retreats & Offsites Unpacked by Assemble Hospitality is about what happens when people step away together and find a deeper sense of belonging. We share stories and best practices from retreats and offsites to explore how intentional gatherings create change.

Information

  • Creator
    Assemble Hospitality Group
  • Years Active
    2025 - 2026
  • Episodes
    22
  • Rating
    Clean
  • Copyright
    © 2025 Assemble Hospitality Group
  • Show Website
    Retreats & Offsites Unpacked