‘This Old House’ Host Kevin O’Connor on How ‘Dumb Luck’ Landed Him Dream Job

When Kevin O’Connor sent a letter to This Old House in 2002 regarding an 1894 Queen Anne Victorian property he’d bought, it changed his life forever. The banking and finance executive was merely seeking help with a wallpaper conundrum, but “dumb luck” landed him his dream job. He ended up appearing on what would become the spinoff Ask This Old House and producers saw his onscreen potential. O’Connor went on to become a regular fixture for the franchise ever since. Now This Old House is gearing up for Season 48 and Ask This Old House is marking a Season 25 milestone October 1 on PBS (October 5 on The Roku Channel).

Much like the flagship series, Ask This Old House also became an Emmy-winning series. The concept was simple. Helping homeowners solve improvement projects based on advice from experienced experts including Tom Silva, the general contractor who had been around since the beginning. 

Upcoming episodes will see more calls from across the country get addressed, from leaky faucets to smart home technology. The show also brings forth a new era through the launch of an AI assistant, Ask This Old House Plus (Ask TOH+), which provides an online resource for homeowners to ask for advice on projects. The tool will pull from decades of This Old House and Ask This Old House articles, videos, expert knowledge with links to relevant articles, videos, and original sources.  

Ahead of the premieres, O’Connor shares his memories from working on the shows and their longevity. 

You took a leap of faith all those years ago when you wrote that letter to This Old House. Fast forward to today and you’re hosting Season 25 of Ask This Old House. Put that into perspective. 

Kevin O’Connor: Well, it started with a good dose of dumb luck. I will never forget that. I was not looking to get into television. I wasn’t even looking to get on my favorite show back then. I just wanted some help fixing up the old house that my wife and I bought. I do smile at the fact that one of the first things we decided to do after we bought the rundown old house and started working on it ourselves. We couldn’t figure something out that we actually turned into This Old House. In  hindsight, it’s what millions of people have done for 25 years of Ask This Old House and 40-some seasons of This Old House. So I was glad it started that way, and now I consider myself to be extremely lucky. I got the chance to work on my dream show without ever wanting to be on TV. The people who I work with that I used to idolize are now some of my best friends, and we’re still at it, which is kind of crazy to think about. It’s a privilege.

What are your early days working on the shows like? 

Two things. First, the incredible graciousness of the professionals who put their arm around me and embraced me without second-guessing it at all. When I joined, the two previous hosts had been at it for 24 years. The show is already iconic. Their names were already iconic, and I was a young kid who was asked to be the third host. To work with Norm Abram, and Tom Silva, and Richard Trethewey, and Roger Cook. who have been there, almost each one of them, from the very beginning or very soon thereafter. They never said, “Oh, you’re going to have to earn it.” They said, “You’re part of the team. We embrace you.” I’m super gracious about that. 

And then the second thing, I was always in awe of their expertise. The endless depth of their knowledge, I still ask the questions. I’ve learned a lot. Sometimes I know the answers to the questions I’ve asked. But I still ask the questions, and these people nail it. They grew up in the trades from young ages, sometimes second, third generations. Richard’s a fourth-generation tradesperson. They know their stuff, and it’s just so cool to be around such expertise.

Was there an instance that really put in perspective the impact that you and the show have?

Well, I’ll tell you one that was impactful to me. It was a two-family, so there were two kitchens. We were in the downstairs kitchen, wanting to take down a load-bearing wall, and I knew I needed a beam. I didn’t know what size it should be because I’m not an engineer. I called up Tommy Silva for some advice. Tommy Silva, our general contractor, at the time, and still is, asked me a couple questions. How far, how long, what’s above it, that type of thing. He goes, “Let me call my engineer and find out.” That’s what he said. And a week or two later, as I was down there in that kitchen working on it, I heard his truck. He had this big old diesel pickup truck. I just knew the sound, because I was around it so much at that point. I heard the truck. And I was like, what? It’s a Saturday morning, like, what’s going on? 

I went out to see him, and instead of having an answer for what size beam, on the back of his truck was the beam with two of his guys sitting in the cab of the truck with them. He didn’t give me an answer. He brought the beam and spent the day helping me put it in. I’ll never forget how much that embodies who these people are. They are incredible tradespeople, but at the end of the day, they’re teachers. Their passion.is spreading their knowledge and helping folks. I just filmed a segment yesterday where we’re talking about how one of the most common questions we get is how do I identify a load-bearing wall, and how do I move it? That happened to me 25 years ago, and that guy didn’t show up with an answer. He showed up with his tool belt in his hand and showed me how to do it. That’s our DNA. It’s a family that has been built. 

Do you attribute the fact many within the team have been doing it for so long as a reason for the franchise’s longevity? 

A hundred percent I would. I like to use the word authentic. Viewers know that they’re real contractors. They’re not making it up, they’re not pretending to be that, just for television. They’re contractors first, and almost reluctant TV personalities second. but authentic. The term also goes to our relationship. People see us having fun on camera with each other, giving each other grief like you do on job sites. The little takedowns and the jabs, but they can tell that we like each other, that we like what we do, and we like doing it with each other. So that’s very authentic. I think that’s what resonates. The reason I think we’re still relevant and popular is because they’re professionals who give good advice, and people enjoy watching us enjoy each other and working with our hands.

One of your show family passed away in 2024 in garden and landscape contractor Roger Cook. Talk about how you all got through that time and kept the mission alive. 

Roger was a bear of a man, a huge personality, physically huge. One of my closest friends, so it’s still emotional, you know, that he died, and he died so young. He came up just recently as we’re celebrating our 25th anniversary. His face is all over the clips and things like that. When I posted a picture of him soon after we announced his passing, it took me days to read the comments. People thanked us. They talked about how they were inspired to work in the yard. They talked about how they planted a tree as soon as they heard Roger’s passing, and it just really brought home.to me. The reality that we have an effect on these people’s lives. 

We become part of their families. We became part of their rituals. They loved Roger, and all he did was show them how to dig in the dirt and plant and keep their stuff alive. And it kind of seems insignificant as a weekend project, but it was so not insignificant in their lives. He made it very clear to his son. He had a degenerative disease, so he knew it was coming. He made it very clear to his son that he wanted to have a foundation that survived him. And the [Cook Family Giving Fund] is focused on horticultural landscaping and helping. young people get into the trades. That has always been his passion, and that keeps going after he’s gone. We’ve honored that. And it’s right within our mission as well.

When you look at Ask This Old House, do these milestones like Season 25 make the episodes coming up especially meaningful?

A big part of our mission going forward is more of the same. People keep writing us questions. New people keep buying houses. People keep trying to figure out projects they’re doing at home. So we’re going to keep answering the questions and show up with our professionals and show them how to do it. It’s more of the same, and part of that comes from the fact that it’s a celebration of 25 years of on-the-air for Ask This Old House. It’s fantastic, but also contextual because This Old House is pushing 50 years. And that tells us that 25 isn’t the pinnacle, 25 could be the midpoint, or just the very beginning. For us, it’s a celebration, but it’s also dedication to give folks more of what we’ve done for those two-and-a-half decades. 

What are some of the cases you tackle, maybe something for the first time that you’re excited for viewers to check out? 

Well, there’s a whole bunch of new technology out there. Most of it comes in the heating and cooling world, the efficiency world. Richard Trethewey , who’s our plumbing and heating contractor, who’s been with us literally since the very first episode season of This Old House back in 1979. He continues to teach those lessons, but his son, Ross, is now a cast member. He’s a professional mechanical engineer, runs his own business designing heating and cooling systems. So again, he’s a professional first, television person second. He and everyone else is just bringing the latest and greatest to the viewers. So we’re going to learn about all that stuff, and it might be the wild technology and efficiencies that we get from heat pumps now. It might be from factory tours where we see efficient windows, new ways to build these types of things, products and materials to keep our houses dry. Like, there is no end to the progress and the technological advances being made in the construction industry, so that’s just more content for us. You’ll see the tried and true test of professionals, and you’ll see their kids. Talking about the next generation of these technologies, we’re going to keep it going.

Do your kids watch the show much and are involved at all? 

What they’ll see is a father on television. They get to work with me. They come to the job sites, those types of things. We do projects around the house, and sometimes it’s forced labor. Sometimes it’s a labor of love, whether it’s the treehouse or the zip line. But I pretty much let them choose their own path, and I don’t force the television thing down their throats, because none of us really take pride in the TV personality part of what we do. We kind of focus on working on job sites. I come home most days with dirty boots, a pair of jeans, and my sweatshirt off because I just spent the entire day working on a job site. There was a time when they were very young that they thought Dad was a carpenter, which made me smile. I had to dispute that I just worked with carpenters. I do kind of like the fact that they mostly think of someone who comes home at night after having spent his day on a job site as opposed to on someone’s television set.

Is there one thing that you must have on your travels, outside the typical stuff that you bring with you?

Coffee? There’s a whole system in place, as we talk about every morning. We’ve got to get the equipment to the job site when we travel, because when we travel, we’re on someone else’s job site, but we’ve got to get our tools, our equipment, camera, and all that kind of stuff. Anything can go wrong on that job site, and we’ll roll with it. But also think who’s bringing the coffee to the job site? We just need that because we don’t know what this guy who runs this job site in Chicago or down in New Jersey is going to be like, and so we bring our own coffee. It’s a small indulgence, but coffee fuels the job site. 

Anything else you want to tease about the challenges you’re going to face or what fans can expect from the new seasons of both shows? 

We’re going to take a moment to celebrate. I think the viewers are going to appreciate that because we’re going to look back over those past years. We’re going to remind them of the legacy, and it’s going to be kind of fun. You’re gonna see a young Kevin O’Connor, Tom Silva with dark hair instead of gray hair and all those types of things. We’re going to talk about young people getting into the trades. Why we think more of them should do it, to continue the legacy that we’ve tried to put forward, which is it’s a good job. It’s a great career, so we’re going to talk about that a lot. We’re going to show them some of the people who started young as apprentices are now people who are on the show, or part of our team. I personally love it, because that’s kind of my trajectory as well. Sort of not really knowing that he wanted to be in it, doing it, and was embraced by these professionals, and that’s what we do with young apprentices. So, we’ll talk about that as well. You’ll see that on both shows. Putting the tools in inexperienced hands, knowing that they are an apprentice today, but they’ll be a mentor tomorrow. 

This Old House Season 48 premiere, October 1, PBS (Check Local Listings)

Ask This Old House Season 25 premiere, October 1, PBS (Check Local Listings)