👋 Hey there, it’s Doug!
Welcome to the inaugural issue of Free Time, Groupbook’s new newsletter. I’m Doug Freeman, founder/CEO of Groupbook and chief defender of planners’ sanity. After thousands of bookings and countless late‑night planning sessions, I realized something: group travel shouldn’t require a PhD in spreadsheets.
Our mission is to help hotels better tap into youth sports, wedding and events demand and to help planners organize and monetize events through commissions or other rewards. We strive to drastically improve the stay‑to‑play structure and provide real value to groups of all kinds. Here’s how that mission comes to life.
📌 What is Groupbook (and why should you care)?
We created Groupbook after dealing with poor technology and even poorer communication while running baseball tournaments and working with thousands of weddings. Whether you’re a team mom coordinating a single squad, managing a 30‑team organization, running hundreds of weddings and events or just on the road with your group, the tools and resources available just didn’t deliver.
Growing up I loved travelling across the country playing and coaching baseball; some of my best memories are from hotels with my teammates. I also got to enjoy nearly a week in Malta with all of my family and friends staying at the Westin Dragonara for our unforgettable wedding (see the fireworks, literally, from that night up top). Those experiences remind me why this problem is important to me and why we’re striving to provide enormous value to our entire network.
In short, we’re the travel marketplace that works for planners – not the other way around.
🔎 The problem we’re solving
Booking group travel today feels like herding cats. Organizers juggle multiple hotels, rates, contracts and attendees while trying to actually run their event. Hotels also miss out on significant revenue because room blocks aren’t optimized. We tackle these pain points by automating contracting, delivering data‑driven rates and unifying communication. Think of us as the end of the “reply‑all” nightmare.
💡 How we do it (with a dash of AI)
Our marketplace is powered by AI agents trained on years of communications, contracts and emails, helping both hotels and planners find the perfect fit. Here’s how our tech works for you:
AI agents & matching. Our AI agents digest past negotiations and agreements to match planners with hotels that fit their budget and needs.
Dedicated hubs. TeamHubAI, HotelHubAI, PlannerHubAI and other tools give each user a tailored interface for creating events, managing room blocks or selling rooms.
Real‑time insights & dashboards. Monitor pickup, forecast demand and adjust pricing from customized dashboards and all‑in‑one views.
Marketplace & earnings. Planners can earn commissions or rewards by monetizing their events while hotels tap into youth sports and wedding demand.
🏨 Partner spotlight
In every issue we’ll highlight a partner using Groupbook to create extraordinary experiences. This month’s shout‑out goes to DASKK Hotel in Orlando, one of the first adopters of HotelHubAI. This cool, affordable new brand – reminiscent of the Kimpton style – boasts a great location that’s perfect for teams and groups. By embracing our platform early, DASKK’s team uses HotelHubAI to find new leads and communicate with planners.
🌱 Community & what’s next
I’m a firm believer in building community – the most successful newsletters grew by encouraging referrals and feedback. Here’s how you can get involved:
Book thousands of rates exclusive to GB members.
Tell us your biggest group‑travel pain point. Hit reply and share the headaches you’d like us to fix. Your feedback shapes our roadmap.
Share Free Time with a friend. Our planner/team/org referral program pays $50 per signup. If you know a planner who’d love easier group bookings, send them our way – there’s no limit on referrals!
Stay tuned. We’ll be in your inbox every two weeks with tips, partner stories and a few jokes. If you prefer monthly updates, let us know and we’ll adjust accordingly.
✨Thank you!
Thank you for being part of the Groupbook family. Whether you’re a planner, a hotelier or someone who simply enjoys reading about travel and technology, we’re excited to share this journey with you. We promise to keep things informative, entertaining and always worth your time.
This newsletter is my way of sharing what we’re building, celebrating our partners and sprinkling in a bit of travel‑and‑tech magic. Expect a dose of humor, some hard‑won wisdom and tips you can use right away.
Until next time… may your inbox be ever interesting and your room blocks always full!
Doug Freeman
CEO & Chief Time‑Saver, Groupbook