Former mayor and local business owner Doug Olerud has launched a new podcast called “Doug Has Questions.” The first episode came out Nov. 30, 2025, and he has released a dozen more audio and video interviews since, primarily of Chilkat Valley locals. Olerud sat down with the Chilkat Valley News’ Rashah McChesney to talk about what he hopes people take away from his new show. 

This conversation has been edited for clarity and brevity. 

How long have you been thinking about having a podcast? I know you and I were having conversations sort of on and off for a couple of months just whenever we saw each other. I got the impression you’ve been thinking about it for a while. 

I’ve been thinking about doing something for pretty much almost 12 years now, and it was just recently that the podcast idea came to me. I had never listened to podcasts until pretty much this last year and I started listening to some and a lot of them were just — ones that I couldn’t stand for very long because it was very strident. ‘We believe this, we believe this,’ and that’s who all their guests were. 

I was looking for something that was more all encompassing that people from different viewpoints could talk about their stories. I started listening to the “Shawn Ryan Show.” 

I kind of based my format on him of just talking to people from the beginning of their life, and as the more I listened to him, the more I thought this would be something that’d be really cool with the people in Haines.

One person told me, ‘If you’re going to do a podcast, if you can’t sit down in 15 minutes, come up with 20 guests or 20 topics that you want to cover, you need to come up with something else.’ And the first time I tried that, I came up with 75 people I wanted to interview. So I thought, well, at least I got 75 episodes if all of them say yes, so maybe those will work out. 

When you say you’ve been thinking about doing something for 12 years now, what was that something? 

A lot of people in Haines know that in 2014, I gave the commencement speech for the high school graduating class, and I just thought I was doing just a quick speech for the kids, but the response that I got from it from community members was really overwhelming. And several people were like, you need to write a book. You need public speaking. You need to do this. You’ve got a message, and that kind of hung in the back of my mind.

I’d come up with ideas, and I’d mention it to friends and they’d all laugh at me like, ‘yeah, that’s not a good idea. You should not do that.’ And so it just kept percolating in my mind over and over. 

And then when this one came up I started gradually mentioning it to friends and they’re like, ‘yeah, you need to do that.’ And I mentioned it to somebody else and they’re like, ‘yeah, you need to do that.’ And finally, I got enough, ‘yeah, you need to do that.’ 

What were some of those things they told you were not a good idea? 

I’m not gonna answer that. I might still try some of them, regardless of people thinking they’re not a good idea. 

When I got into podcasting, particularly in public media, there’s all of these conventions they teach you in a news ecosystem … you’re trying to fit the conversation to the limitations of a broadcast schedule. But your episodes are going for two hours, sometimes close to three hours. What do you feel that adds to the conversation in Haines? 

I don’t know if I’m necessarily trying to contribute to the media ecosystem, but more of just an understanding of the people that we share Haines with. I think it’s just a personal connection. One of the things that was frustrating for me as mayor is you get up in a public meeting, no matter what the topic. Each person can get up and they can say their opinion for three minutes, the next person says their opinion for three minutes, and so however many people there, they get their three minutes. The assembly gets up, and they say their opinions and then they vote. But you don’t really get to talk about why somebody feels that way. What are the factors that went on in their life that led them to that current perspective? 

I think before you get to the policy, if you understand or have a broad-based view of how somebody was raised, the struggles they’ve gone through, the successes they’ve had. Maybe we’ll be a little less volatile when we have a disagreement with them over a policy, knowing the ups and downs of their life. 

Where are you recording these?

So part of the original thought was kind of to do this as a tourism promotion thing, and I wanted to use the local restaurants and watering holes, it’s like in the distillery and the brewery. Just different places. 

Amazing. But, the audio quality?

That ended up being the problem. Lee Robinson was great and let us use the Rusty Compass for our first couple episodes, and we were having to turn off a bunch of his equipment in order to do it, and we’re making sure everything is back up. And then with other people that I talked to about using their space, when they’re available, when the space is available, it wasn’t really conducive to when I was available or my guests were available. And so right now we’re just recording it in the back part of the [Alaska Sport Shop]. I mean, just clear merchandise out of one of the aisles and set it up in there. I’ve got a spot that I’m going to try and develop a little better studio, so I don’t have to just record these when the Sport Shop is closed. 

Are you trying to make a living at it?

No, I have a lot of goals with this, but none of them are tied to economics. I would like it to pay for itself, and the people that help me with this, I would love to be able to pay them more than I’m currently paying them. That would be great. But for myself, if this can just pay those people and pay the expenses of it, I would be thrilled with that. 

Did it give you a different understanding of what the reporters at KHNS or the reporters at the CVN are doing when they’re trying to gather stories in the field? 

A little bit, but I think it’s a little different. Because you and I have had this conversation, because with one of my first interviews — Bart Henderson, I saw you in the store, and you’re like, ‘do you have your list of questions down?’ I’m like, ‘yeah, no, I don’t.’ 

I have topics in my mind that I want to discuss. And depending on where the conversation goes will depend on which questions I ask. 

So much of it is just based on what somebody says and I just react to that. And so I try to make it more of a conversation rather than an interview where we’re just talking about life.

And so I think it’s a little bit different than a news interview … news people have a really tough job trying to get an interview. 

Over the course of my career as a journalist one big thing that has changed is that people have just generally gotten a lot more suspicious of traditional media. I’ve been a professional journalist since 2010, and in that period of time, there have been people in communities that I go and try and talk to, and they’re just very reflexively anti-news, the media, whatever you want to call it. I wonder if, because you’re not a journalist or … because you’re not carrying that notebook around full of questions, do you feel like you’re sort of reaching people who maybe wouldn’t go listen to KHNS or read the CVN? 

Olerud: Possibly. I look at it that the more perspectives and the more information that a person can get on the topic, the better decision you’re going to make. That’s something I told people when I was mayor: I want to listen to everybody. I think I’ve got some really good ideas in life on how to do things, but I’ve also found out that a lot of ideas that I thought were really good, really weren’t that good. It’s just the opportunity that I can go for an hour and a half or three hours and talk to one individual, or we can spend maybe an hour on a single topic. That allows a lot more nuance than you trying to write an article that fits in a half-page of the CVN or KHNS can do a five-minute interview that they’re putting on the radio. I think it just adds. I don’t think it’s replacing, but I’m hoping it adds to the conversation, and it’s another place where people can learn something. 

McChesney: Where can people find your podcast, particularly people who do not know what podcasts are and aren’t sure where to get them. 

Olerud: If you want to watch it, it’s available on YouTube, and if you just want to listen, it’s either on Apple Podcasts or Spotify, and if you go on to any of those platforms and just type in Doug Has Questions, that’ll come up and you can find the episode you want and click on it and give it a listen.