Rob Wreglesworth started reaching out to guests for his podcast expecting to be ignored. These were people whose time was difficult to secure through normal channels—an hour-long chat would have been a hard sell without a reason behind it. But with a podcast as the frame, something shifted.

“I always am surprised at how many people say yes and how many people are willing to dedicate that much time to a really in-depth conversation. I’m just delighted every time someone says yes and takes the time out to speak to me for that long.”

What’s striking isn’t the observation itself. Most podcasters have experienced this—the person you were sure would say no writes back within hours. The guest you considered “out of your league” turns out to be enthusiastic about a show with a modest audience. It happens often enough that you’d think we’d stop being surprised by it.

We don’t.

There’s something persistent about the assumption that we’re imposing. That our invitation is a burden. That the person on the other end is doing us a favor by showing up. Wreglesworth describes the podcast as a “superpower” that gave him the ability to frame conversations with more meaning, and he’s right—it did. But notice the underlying belief: without that frame, he assumed the conversations wouldn’t happen. The podcast didn’t create generosity in other people. It gave him permission to ask.

This gap between what we expect and what we receive says less about our guests than it does about us. Podcasters consistently underestimate their own value as interlocutors. We think the draw is the platform, the audience, the reach. But most guests on indie shows aren’t calculating exposure. They’re saying yes because someone is genuinely interested in what they think. That’s rarer than we realize.

The question worth sitting with is why this surprise renews itself. Wreglesworth has been podcasting since 2019. He’s had the experience of people saying yes dozens of times. And yet “delighted every time” suggests the pattern hasn’t become expected—it still registers as generous, still feels like a gift rather than a transaction.

Maybe the surprise persists because we’re measuring from the wrong baseline. If you start from “who am I to ask,” then every yes is an exception to the rule. But what if the baseline is wrong? What if most people genuinely want to be asked thoughtful questions by someone who cares about the answers? What if the default isn’t reluctance but willingness, and we’ve just been projecting our own insecurity onto everyone else’s inbox?

This has practical implications. Podcasters who expect rejection tend to hedge their pitches—apologizing for the intrusion, offering excessive justification, signaling that they know they’re asking too much. All of which makes the ask feel like exactly the imposition they feared. The podcaster who writes a confident, specific invitation—here’s why I want to talk to you, here’s what I think we could explore together—is more likely to get a yes, not because confidence is persuasive, but because it matches the reality: most people are glad to be asked.

Wreglesworth’s surprise isn’t naivete. It’s the honest recognition that generosity keeps showing up where we expected scarcity. The interesting question isn’t why people say yes. It’s why we keep assuming they won’t.

This field note references the Podtalk episode “Reflecting with Rob Wreglesworth,” published February 29, 2024.