Host Kevin O’Connor never dreamed of hosting Ask This Old House, but a string of good luck seemed to drop the job into his lap. Kevin was always a fan of This Old House and enjoyed working with his hands. When he and his wife bought their first home, they purposely looked for a fixer-upper. After handling some of the projects themselves, the O’Connors sent a letter to the This Old House team. Unknown to him, a new show was already in the works: Ask This Old House. After receiving his letter, the crew arrived at Kevin’s house for a house call. The crew helped Kevin handle some projects around his home, and his personality sparked an interest. About a month later, Kevin received a phone call from the production team asking if he would be interested in hosting the show, and he knew he couldn’t turn it down. While he was excited to take the job, Kevin didn’t think it would last long. As he explained his leaving to his then-boss in the finance industry, Kevin asked him to keep a spot open, as he thought he’d be back in the finance world in around 12 months. That was almost 20 years ago. Kevin got his start by working with the crew of experts and tradespeople. Plumbing and heating expert Richard Trethewey had Kevin dig ditches. General contractor Tom Silva put Kevin to work cutting wood. He built his skillset with on-the-job training, but his excitement for new projects and to learn never needed bolstering. Kevin’s favorite part of his job is when he gets to work side-by-side with the crew. He finds satisfaction in working with his hands and appreciates the opportunity to shift from the host to the crew. He tries to hand his love and satisfaction down to his kids with projects around their home, hoping that it might stick with them. His other hope? That his kids don’t work in television.