AssociationHelpNow

Raymond Dickey

AssociationHelpNow® delivers practical, real-world conversations for community association managers and board members who live this work every day. Each episode features candid discussions, expert interviews, and timely insights covering legal, insurance, operational, leadership, and communication challenges facing HOAs and condominiums. From livestream highlights to workshop takeaways, the show bridges the gap between theory and practice—helping listeners make smarter, more confident decisions in complex environments.Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice and may have been edited.

  1. Luxury High-Rise Jeffrey Ulm Interview: Miami’s Ultra-Exclusive World

    1D AGO

    Luxury High-Rise Jeffrey Ulm Interview: Miami’s Ultra-Exclusive World

    Luxury High-Rise Jeffrey Ulm Interview: Inside Miami’s Ultra-Exclusive World The Brickell/Miami high-rise world is nothing like typical association management. From cold plunges and cigar lounges to 100-story towers, Bentley deliveries, branded buildings, concierge-level expectations, and the intense hospitality standard required to succeed… this interview with Jeffrey Ulm, CMCA, AMS, PCAM gives managers and board members a rare inside look at one of the most demanding management environments in the country. Walk with us through what “perfection” really means when residents fly in for only two weeks a year and expect every elevator, amenity, and service touchpoint to operate flawlessly. You’ll hear about hidden pressures, surprising perks, how luxury managers develop their careers, and why these buildings are actually some of the most rewarding places to work, if you’re built for it. Video: https://youtu.be/IJu9_K5mPHY Raymond Dickey • AssociationHelpNow  https://www.linkedin.com/in/raymondjdickey Jeffrey Ulm, CMCA, AMS, PCAM • FirstService Residential • jeffrey.ulm@fsresidential.com • www.fsresidential.com Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. This content does not constitute professional advice and may have been edited. #HOAManagement #CommunityAssociations #PropertyManagement

    16 min
  2. High Rise Luxury Management: What Happens Behind the Front Desk

    1D AGO

    High Rise Luxury Management: What Happens Behind the Front Desk

    Inside Luxury High Rise Management: What Happens Behind the Front Desk Curious what separates a high end building from a true luxury high rise? This conversation gives you a rare look at the service culture, resident expectations, and leadership mindset required to operate in one of the most demanding segments of the community association world. You will hear what happens when highly successful residents expect immediate service, how managers build a high performance staff culture, and the surprising myths that many managers and board members still believe about luxury properties. If you want to understand how elite communities actually function behind the scenes, this is the video to watch. Raymond Dickey • AssociationHelpNow https://www.linkedin.com/in/raymondjdickey Jeffrey Ulm, CMCA, AMS, PCAM • FirstService Residential • jeffrey.ulm@fsresidential.com • www.fsresidential.com Find More Videos: https://www.youtube.com/@AHNData/videos Find Great PodCasts: https://www.buzzsprout.com/2565449 Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. This content does not constitute professional advice and may have been edited. #HOAManagement #CommunityAssociations #PropertyManagement

    8 min
  3. Rule Enforcement Traps Boards Don’t See Coming

    3D AGO

    Rule Enforcement Traps Boards Don’t See Coming

    Rule Enforcement Traps Boards Don’t See Coming One “simple” rule violation can turn into a privacy complaint, discrimination claim, or a D&O headache fast—especially when boards and managers improvise enforcement. YOUTUBE: https://youtu.be/MQ_5Knn2mBY In this session, we pressure-test real-world scenarios that feel straightforward… until they aren’t: “Reasonable accommodation” requests (and what you can ask for without creating a bigger problem) Warnings, hearings, and consistency (what courts and owners often expect—even when your docs don’t spell it out) Documentation landmines: photos, interviews, surveillance, interior visibility, and “how far is too far?” The unspoken risk: rule enforcement that accidentally becomes about something else Plus: “You’re the Judge” cases that split even attorneys (signs, door decor, locker rooms, and more) If you’ve ever thought, “Why is this getting so messy?”—this is why. David Byrne, Esq. • Ansell Grimm & Aaron, PC • dbyrne@ansell.law • www.ansell.lawRaymond Dickey • AssociationHelpNow.comGregg V. Gerelli • Gerelli Insurance Agency, Inc. • gregg@gerelli-insurance.com • www.gerelli-insurance.comCory Kravit, Esq. • Kovitz Shifrin Nesbit • ckravit@ksnlaw.com • www.ksnlaw.comJohn LaGumina, Esq. • The LaGumina Law Firm, PLLC • jlagumina@laguminalaw.com • www.laguminalaw.comCynthia Jones, Esq. • Sellers, Ayers, Dortch & Lyons, P.A. • cjones@sellersayers.com • www.sellersayers.comO’Neil McCoy, MRED, CLCS • McGriff • omccoy@mcgriff.com • www.mcgriffinsurance.comMatthew W. Heron, Esq. • • Hirzel Law, PLC • mheron@hirzellaw.com • www.hirzellaw.comHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. #HOAManagement #CommunityAssociations #PropertyManagement

    1h 17m
  4. The Four Corners Rule

    6D AGO

    The Four Corners Rule

    The Four Corners Rule: If It’s Not Written, It Doesn’t Exist When disputes arise, it’s not about what someone meant, it’s about what’s written. The Four Corners Rule is the legal principle that says only the words within a document itself count. For boards, managers, and even vendors, that can mean the difference between being protected or being exposed. YouTube: https://youtu.be/bj6katQnIgc John LaGumina, Esq. / David Byrne, Esq.  / Deborah Gerelli, CIRMS / Michael Pereira, Esq. / Cory Kravit, Esq.  / Christian Saville, Esq.  Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. This content does not constitute professional advice.

    59 min
  5. HOA Manager Roundtable - It’s Water

    JAN 19

    HOA Manager Roundtable - It’s Water

    Community Manager Roundtable – Live Interactive Livestream - Plus: Let's Talk Bodies - of Water.  Kristine Bates, CMCA, AMS, PCAM / Thomas Claus / Nichole M. Haddock, CISR / David Byrne, Esq.  Hosted by AssociationHelpNow®. #HOAManagement #CommunityAssociations #PropertyManagement

    1h 1m
  6. Hidden Reserve Infrastructure Risks Communities Miss

    JAN 18

    Hidden Reserve Infrastructure Risks Communities Miss

    Communities miss the danger they can’t see. Hidden infrastructure failures hit fast — and hit hard. Get ahead before the liability lands on you. In-depth and basic reserve questions answered. Michelle Baldry, PE, PRA, RS • Reserve Advisors, Inc. • mbaldry@reserveadvisors.com • www.reserveadvisors.com Raymond Dickey • AssociationHelpNow.com Hosted by AssociationHelpNow® #HOAManagement #CommunityAssociations #PropertyManagement

    30 min
  7. The Quiet Work Habits That Prevent Manager Burnout

    JAN 18

    The Quiet Work Habits That Prevent Manager Burnout

    Protect your mornings, defend your focus, and cut hidden burnout risks fast. Small habits beat stress when the pressure hits. Taylor Hayes, CMCA, AMS • CAMS Raymond Dickey  — Hosted by AssociationHelpNow® HOAManagement #CommunityAssociations #PropertyManagement

    27 min
  8. Annual Association Checklist Most Boards Quietly Miss

    JAN 17

    Annual Association Checklist Most Boards Quietly Miss

    Most HOA problems aren’t sudden—they’re missed reviews: coverage, finances, contracts, enforcement. Run this annual checklist and catch the quiet risk before it becomes liability. Raymond Dickey / Christian Saville, Esq. / John LaGumina, Esq. / Jeremy Fernando, Esq. / Gregg Gerelli / Dawn Becker-Durin, CIRMS / David Byrne, Esq. / Cory Kravit, Esq. / Elliot M. Engstrom Hosted by AssociationHelpNow®. #HOAManagement #CommunityAssociations #PropertyManagement

    59 min
See All (13)

About

AssociationHelpNow® delivers practical, real-world conversations for community association managers and board members who live this work every day. Each episode features candid discussions, expert interviews, and timely insights covering legal, insurance, operational, leadership, and communication challenges facing HOAs and condominiums. From livestream highlights to workshop takeaways, the show bridges the gap between theory and practice—helping listeners make smarter, more confident decisions in complex environments.Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice and may have been edited.

Information

  • Creator
    Raymond Dickey
  • Years Active
    2025 - 2026
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © 2026 AssociationHelpNow
  • Show Website
    AssociationHelpNow