The Rooms Are Filling Up Again
August 24, 2026
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Show Notes
Eddie and Betty's Conversation
Welcome to The American Retirement Advisor podcast. I'm Betty, and Eddie is here with me in the studio today, which honestly makes every conversation better. Eddie, I want to dig into something a little different today. Ian Schaeffer, our company's COO, wrote a piece that isn't a how-to guide or a list of strategies. It's a memoir, almost. A look back at the Medicare workshops this company used to run, and a look forward at what's coming next. And I found myself just sitting there reading it, thinking about what it must have felt like to be in those rooms.
Good to be here. And you're right that it reads differently than most things we talk about. Ian's not describing a product or walking through a rule. He's describing a feeling, and he's pretty specific about it. He says it lives in your chest, that pre-show energy right before a room fills up.
He's very specific about the details too, which is what made it feel so real to me. The Beach Boys playing over the speakers as pump-up music. I did not see that coming.
It tells you something about the culture they built around these events. This wasn't a sterile conference room experience. They were intentionally creating an atmosphere, a feeling that said we're glad you're here and this is going to be worth your time. The music was part of that.
And then he describes David Edge standing off to the side, scrolling on his phone, completely calm, while Ian is the one in the back watching the door, counting seats, fixing the projector. You can feel who's doing what.
That's a real division of labor. Ian is clear that he's not the advisor, never has been. His job was making the machine run. Edge steps up when it's time to present, and apparently he was right on time, every time. Ian makes a point of that.
The door thing is what got me. He says no matter how booked they were, the room would sit nearly empty until about five minutes before showtime. And then all at once, dozens of people.
That's just how a crowd works. Nobody wants to be the first one in the room sitting there waiting. So everyone times it the same way without coordinating, and suddenly the room is full. What I like about how Ian tells it is that this apparently happened every single time. It wasn't a fluke. Zero to dozens in one breath, as he puts it.
And people were picking up the newsletter on the way in and starting the word search before they'd even taken their coats off. There's something so warm about that detail. They made it comfortable enough that people settled right in.
A word search is a great leveler. Nobody feels stupid doing one, it gives you something to do with your hands, and it eases you into the topic gently. These were Medicare workshops, so the subject matter is genuinely complex. Starting with something low-pressure was probably intentional.
Speaking of the complexity, I loved the government joke. Edge would warm the room up along the lines of, now in case any of you are here from the government. And Ian points out it wasn't really a joke at all.
Right, because every single one of those workshops had to be filed with CMS and approved before they could hold it. CMS being the Centers for Medicare and Medicaid Services, the federal body that oversees all of this. So when the presenter makes a crack about government observers, the room laughs, but the underlying message is: we did everything right, we're playing by the rules, and we respect the seriousness of what we're talking about. It's a clever way to establish credibility while also breaking the tension.
It's like the joke is doing two jobs at once. Making people comfortable and making them feel safe that they're in good hands.
And then they started right on time. Every time. Ian mentions that twice in different ways, and I think it matters. Starting on time is a form of respect. It tells people you value their schedule as much as your own.
The part where Ian explains his own role in all of this really stopped me. He's watching his father, David Schaeffer, sit across from families and help them make real decisions. And Ian says he realized he wanted to reach the people who weren't in the room yet.
That's a meaningful distinction. The advisor helps one family at a time, which is irreplaceable work. Ian wanted to scale that outward. He says it directly: he wanted to help more people than could ever fit in one office. The workshops were his answer to that. Fill a library room, reach dozens at once, do that across a whole valley, and suddenly you're touching hundreds of people every month.
And they did that for a good while. He says they filled libraries all across the valley, helping hundreds of people every single month. That's a lot of families walking out of a library with clearer heads about Medicare than when they walked in.
And then they stopped. While it was still working. That's the part that probably surprises people most. They didn't stop because the rooms went empty or because it wasn't effective. They stopped on purpose.
Can you say more about why? Because Ian's explanation is kind of philosophical and I want to make sure I'm reading it right.
He's pretty candid about it. He says a full room can be a comfortable place to hide. That it's easy to keep doing the thing you're good at without ever asking if it's still the thing you're called to do. So they stepped out voluntarily to figure out who they were becoming. That takes some real self-awareness, to walk away from something that's working because you want to be intentional about the next chapter rather than just coasting on momentum.
Twenty-five years is the window he's thinking about. He says they needed to be honest about what they wanted the next twenty-five years to become. That's a long horizon. That's not just planning a calendar year, that's asking who do we want to be.
Which is actually a question we'd encourage any listener to ask about their own retirement plan. Not just what do I have, but what kind of life am I building toward. Ian's asking it on a company level, but the instinct is universal.
Now, the part of the piece that Ian says he misses most, the close of the workshops, the open Q&A. He describes it as hands going up all over the room, and the presenters getting a smile that stretched from ear to ear.
Most people who do any kind of public presentation dread the open Q&A. Anything can come at you, and if you don't know the answer it can be an uncomfortable moment. But Ian says their presenters loved it. David Schaeffer, Edge, Kyle, they were confident that there was not a single question that room could throw at them that they didn't already know the answer to, or know exactly where to find it. So the Q&A wasn't a gauntlet. It was the fun part.
That kind of confidence only comes from genuine depth. You can't fake that. If you're standing in front of a room full of people with real Medicare questions and you're smiling when hands go up, you have done the work.
And for listeners who've ever sat in a workshop setting and been afraid to raise their hand because they didn't want to ask a dumb question, that's the picture Ian is painting of what these rooms felt like. The people at the front wanted your question. It made their day better, not harder.
So what's the news at the end of the piece? Because he doesn't just leave it at the memory.
The workshops are coming back. He says they want that feeling back in their bones, and the first one is Friday, October second. Back in a room with a screen at the front and a room full of neighbors, as he puts it. And he's looking ahead to helping thousands more through this enrollment season and beyond.
That's a big number to lean into. It tells you the ambition is serious, not just dipping a toe back in.
It lines up with what he said about why he got into this in the first place. Reaching the people who weren't in the room yet. That goal didn't go away during the pause. It sounds like it sharpened.
He closes with something that I thought was just genuinely lovely. He says if you've been carrying questions, come ask them. We saved you a seat. There's a warmth to that, knowing someone held a spot for you before you even knew you needed it.
And Medicare questions are exactly the kind people carry around quietly for too long. The enrollment windows, what's covered, how the pieces fit together, those questions have real financial consequences if you get them wrong, and a lot of people just don't know where to take them. A room full of neighbors asking the same things, with someone at the front who genuinely knows the answers, that's a valuable thing.
If you're trying to figure out whether a workshop like this is right for your situation, or if you have questions that are more specific to your own picture, that's a conversation worth having with one of our advisors directly. The workshop is a great starting point, but your situation has details that deserve a real one-on-one conversation.
And the team at American Retirement Advisors can help you figure out what questions to bring and what to expect. If you're not sure where to start, that's exactly the kind of thing to flag when you sit down with them.
Ian's piece is short but it stuck with me, because underneath the Beach Boys and the word search and the government joke, it's really a story about why this work matters to the people doing it. And I think that comes through in a room. When the person at the front is there because they love the Q&A, you feel it. So if you've been carrying questions about Medicare, October second is your date. Go find a seat. We'll see you there.