Business Events Actually Worth Attending
Mar 19, 2026
I started to add up how much I have spent on attending business events and masterminds. I stopped when I hit $500,000. It made me almost a little nauseous. Over the last 20 years my investment has been well over half a million dollars, but what made me feel this way was that some were transformational and most weren’t.
The difference was never the production value, never the celebrity speakers and never the size of the venue. The difference was always the same three things.
1 - Small Rooms Beat Big Stages
The best events I’ve attended had fewer than 50 people. Not because small is trendy. Because small means you get heard.
When there are 500 people in a room, the speaker can’t possibly address your specific situation. You’re absorbing general advice and hoping it applies to you. Sometimes it does, often it doesn’t, and you leave with that nagging feeling of “that was interesting but what do I actually do with it?”
When there are 50 people in a room or less, the person on stage can look at your workbook, review your notes and give you feedback that’s specific to your business. That’s worth ten times more than a keynote speech from someone who doesn’t know your name.
2 - Implementation Time Matters More Than Inspiration
The events that changed my business all had one thing in common. Time built into the agenda to actually do the work, not just listen.
Inspiration fades and notes get lost. I’ve got shelves full of notebooks from events I attended years ago. I’ve never opened. When I spent time with a detailed workbook and I actually built it in the room, with support, while the teaching was fresh... that kind of work stuck and was always something that I actually implemented after the event.
3 - One Direction, Not Six
The fact that many multi-speaker events are just a host providing a platform for people to sell, and they sell spots to these speakers to get time on the stage, makes the events just full of pitches and calls to run to the back of the room. To be honest, I hate these kinds of events.
These kinds of events also have a massive structural problem. Speaker 1 tells you to focus on YouTube. Speaker 2 says email is king. Speaker 3 is all about webinars. Speaker 4 pitches their mastermind. Speaker 5 contradicts everything Speaker 1 said.
You leave with six conflicting strategies and no idea which one to follow. So you follow none of them.
The best events I’ve been to had a single philosophy running through everything. One direction. One framework. Applied from multiple angles. That’s what actually creates change.
My Own Events Are Built Based on These Lessons
Simplify Summit exists because I wanted the event I’d always wished for. 50 people. Direct access. Implementation time. One host, one philosophy, three connected frameworks.
No guest speakers selling their own programs. No “run to the back of the room” moments. No pitch fest. Just two days of work that leaves you with a clear plan for the next 90 days.
You can find out what I'm up to over at www.simplifysummits.com