Larry O’Donnell, Waste Management

Let me just say, Undercover Boss could not have picked a better way to kick off its very first episode. Waste Management is a company everyone knows — even if you only associate it with the Sopranos for some reason. But what really made the episode hit were the people. The employees they highlighted were absolute standouts. Total GOATs. This episode is the definition of feel-good. And if you don’t tear up at least once, I don’t know what to tell you.

Here’s how it all broke down:

Larry and Fred
Larry did a solid job, but Fred was the one who left a mark. He was encouraging, stayed upbeat, and made the best out of a tough workday. If I were being trained by Fred, I’d feel confident about joining that team. And his smile? Completely contagious. Just one of those people who reminds you why attitude matters so much.

Larry and Janice
Listen, that job is absolutely not for me, but Janice? Queen behavior. The way she treated every client showed that kindness and patience weren’t just part of the job — they were part of who she is. She consistently gave a little extra, just because she could. That’s leadership, plain and simple. There are always limits to what one person can give, but when someone shows up like that day after day, they are a total asset. Some folks pointed out later that Larry’s suggestion of a women’s task force was nice, but it didn’t really solve the core issue, which was the crushing workload. Still, he was trying.

Larry and Walter
Walter’s story hit me hard. He’s been on dialysis for more than 15 years and still walks miles a day collecting trash. That alone deserves all the respect. And in one of the best moments of the episode, he actually fired Larry for not picking up fast enough. It was hilarious and also kind of perfect. Walter led through his mindset. He had every reason to be frustrated with the world, but he chose positivity. That’s rare. That’s powerful. It reminded me of one of my former team members, who was also on dialysis and still wanted to work during her hospital treatments because she didn’t have any PTO left. I’ll never forget how my former boss, Aimee Yerton, taught me what it means to move mountains for your people, when and where it counts.

Larry and Sandy
There’s one moment from this storyline that still gets under my skin. Sandy was docked for being late, and while I understand that rules are rules, not clocking in should just mean you’re not getting paid for that time — not that you lose extra. That’s not leadership. That’s a broken system. And it stuck with me.

Larry and Kevin
Larry, buddy. That meeting? Absolutely could have been an email. No further notes.

Larry and Jaclyn
Jaclyn, you are it. Every workplace has that one person who keeps everything running, is adored by everyone, and never complains even when they’re constantly overlooked. Jaclyn was that person. Larry saw her, appreciated her, and took action right then and there — not after the cameras stopped rolling. And because I’m a little nosy, I looked her up. She’s still with Waste Management, all these years later. That says a lot about what happens when leadership shows up and values someone out loud.

What Happened After
After the episode aired, Larry stepped down from Waste Management and went on to found Rockwater Energy Solutions, a company focused on environmentally responsible solutions in oil and gas. He’s now retired, and he and his wife run a nonprofit that mentors future leaders. From everything I’ve seen, he really does seem to be the same thoughtful, people-first leader he was on the show.

So yeah. When I think about this episode and about Larry, all I can say is: Now That’s What I Call Leadership.