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Retreats & Offsites Unpacked

Retreats & Offsites Unpacked

Written by: Assemble Hospitality Group
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 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.© 2025 Assemble Hospitality Group Economics Management Management & Leadership Self-Help Success
Episodes
  • How Friction During Offsites Is a Good Thing

    How Friction During Offsites Is a Good Thing
    May 6 2026

    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

    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.
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    31 mins
  • How to Create a Men’s Group

    How to Create a Men’s Group
    Apr 29 2026

    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

    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.
    Show More Show Less
    28 mins
  • What Retreat Leaders Can Learn From a Brother and Sister Team

    What Retreat Leaders Can Learn From a Brother and Sister Team
    Apr 22 2026
    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 ThemesWhat 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 timeChapters00:00 – 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 askedAbout 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: LinkedInPaul 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: LinkedInAbout 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.comSocial Media: Facebook | Instagram | LinkedIn | YouTubeCredits: 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.
    Show More Show Less
    31 mins
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