👋 Hey there, it’s Doug!
This week’s theme is value. It took me longer than I’d like to admit to really understand it. The short version: you can’t provide value—in a relationship or in business—without knowing whose problem you’re solving and how they feel it. Listening unlocks that. Everything else is noise.
What I learned (the slow way)
Coaching college baseball: I didn’t play as far as I hoped, so I tried to coach through knowledge—sometimes by example, sometimes by force. I struggled to connect across generations. In hindsight, more questions and more listening would’ve created far more value for those players. Same in recruiting: we landed great talent, but differentiation comes from understanding and communicating value in their words.
Prep Baseball: Starting a company that didn’t really exist in Florida brought a different lesson: hubris hides the value. We worked hard and grew fast, but the ceiling was our ability to clearly articulate value to players, programs, teams, and parents.
Groupbook: Early on, I defaulted to the bulldozer, not the scalpel. There wasn’t one “aha”—just five years of clarity-through-struggle. What I hold now is simple: success correlates with the quality of value you deliver—and the precision with which you deliver it.
Working definition: Value = A specific person’s problem × how acutely they feel it × how precisely you solve it (and show it).
Translation: listen first, then build.
What “value” means at Groupbook (right now)
For teams & organizations: One dashboard for all events. Create a block, share one link, track pickup, travel stops being a second job.
For planners (weddings & events): Earn and provide more value to clients. Room-block tools + commissions or rewards—all the “pro” without extra spreadsheets.
For new event entrepreneurs: A practical on-ramp to event production. Use hotels as a revenue engine to maximize opportunities and make premium experiences possible.
Where we’re going
We started serving tournament organizers, expanded into enterprise wedding partners, and kept searching for the places we can deliver the most value. The truth: group travel is a pain. Different stakeholders, mixed incentives, stay-to-play rules—messy. Our bet is simple: if we equip the people actually paying for rooms (teams, planners, organizers) with tools that remove friction and add upside, everyone else in the ecosystem benefits.
Your part (and my ask)
The only way to prove value is to use the product and tell us the truth. The good, the bad, and the ugly are all welcome—especially the ugly. That’s how we keep sharpening the scalpel.
Start here:
Teams & orgs: https://groupbook.io/solutions/teams
Hit reply with your city + dates (tournament, wedding, holiday travel). I’ll personally point you to strong options and note what worked and what didn’t.
Thank you
To everyone reading and opening—thank you. Your attention is scarce. I’m going to keep earning it the only way that scales: by delivering value.
Until next time—stack hard work, flexibility, and creativity on a relentless search for value, and good things have a way of finding you.
Doug Freeman
CEO & Founder, Groupbook
Chief Time-Saver