Episode 10: Why Your Best Drivers Leave (And What Better Carriers Do Differently) with Charles Gracey

Charles Gracey on Building a Fleet Drivers Actually Want to Stay With

[00:00:00] Charles Gracey: Let’s look at why we’re losing them. If we can fix why we’re losing them, we don’t need to spend $7,000 to $15,000 a month per hire just marketing to drivers to keep up with the churn. Let’s address the hole in the boat and then start bailing out the water.

[00:00:17] John Howland: Welcome to Behind the Freight. I’m John Howland, joined by special co-host Scott Feather. On the show today, we have one of the most amazing people I know: Charles Gracey.

He’s a host on SiriusXM Road Dog Trucking Radio and FreightWaves’ Brake Check podcast, known to most of us as the Dr. Phil of trucking. Charles has built an amazing reputation centered around honest, unfiltered conversations about the realities drivers, recruiters, carriers, and fleets face every day.

Before stepping behind the mic, Charles founded Hot Seat Services, helping trucking companies improve recruiting, retention, and operational performance. He also worked as a driver himself, giving him unique insight into the challenges happening both on the road and in the boardroom.

Today, we’re going to talk about recruiting and retention in trucking, why the industry struggles to connect narrative with reality, and what needs to change to attract and keep the next generation.

I’ve had the privilege of being on Charles’ shows a couple of times. If you look over his left shoulder, you’ll notice that heavyweight championship belt weighing 11.1 pounds! I’m so blessed I got to be on the show where we presented him with that for being a media mogul doing the right thing to move this industry forward. Welcome, Charles!

[00:01:56] Charles Gracey: Dude, that was awesome! Usually, I’m giving people warm welcomes while they threaten to shove me in their pocket and take me everywhere, but can you travel with me?

[00:02:05] John Howland: Hey, I said the exact same thing when I was on your show! With the way you hype up Mark and me at Truckstop, let me tell you, we could do some serious damage together.

[00:02:15] Charles Gracey: When you were giving that long intro, I was getting all hyped up. Then I thought about all the people who do that to me, so yeah, I’m totally going to do it to you!

[00:02:26] John Howland: That’s awesome.

[00:02:27] Charles Gracey: Cents Per Mile was my very first podcast where I got started, which was awesome. Now I do Trucking Cents on SiriusXM and Brake Check on FreightWaves.

[00:02:37] John Howland: How long ago was that?

[00:02:39] Charles Gracey: It seems so long ago, about five years.

[00:02:42] John Howland: That was back when podcasting wasn’t even as big as it is now, right?

[00:02:45] Charles Gracey: It was a thing, but now everyone has a podcast. It’s kind of like everyone having an opinion.

[00:02:51] Scott Feather: You got started early, though, which gives you a leg up.

[00:02:56] Charles Gracey: The industry is going through an identity crisis. When it comes to podcasting, the people who win are the ones focused on true content.

Back in the day, everyone was creating content, but no one was podcasting. Now everyone is podcasting, so whoever focuses on quality content will win.

[00:03:13] Scott Feather: Everybody listens to podcasts while driving, which blows me away. It’s nice to have people putting out good content for an audience that can listen all day long.

[00:03:29] Charles Gracey: I love any content I don’t have to produce myself. I love being a guest, if anyone is hiring, I could just be a professional guest who shows up and talks!

[00:03:39] John Howland: You can be a regular on our show anytime. To kick things off, what has been your most interesting or crazy moment while podcasting?

[00:03:56] Charles Gracey: I’m going to throw myself under the bus. It was when I first started. People think I came out of the womb doing this, but that’s not the case.

There’s a video hidden deep in a vault from my very first show. About ten minutes in, someone said, “Hey, you know you can breathe and blink, right?” It was bad.

[00:04:15] Scott Feather: You were probably like, “Wait, I don’t know how to do that!”

[00:04:18] Charles Gracey: It was terrible, I looked like a serial killer! It was supposed to be easy because I was just talking about my company.

It was my first time on camera. I’d done plenty of public speaking, but with bright lights shining at you and screens distracting you, I just sat there frozen.

[00:04:37] John Howland: Did they tell you that breathing trick during the show so you could inhale, or after?

[00:04:45] Charles Gracey: It was after that cut was done. Shout-out to my good friend Paul Gibson, I think he did that on purpose to have collateral to remind me of where I started. He still brings it up and asks, “Remember when you used to suck?”

[00:04:58] John Howland: Now you’re the man! You can just show him your championship belt and say, “What now?”

[00:05:02] Scott Feather: I’m going to go back and watch that video to see if you actually sucked, because I doubt that was the case.

[00:05:08] Charles Gracey: I challenge anyone who wants to see a “before and after”! Starting a podcast is intimidating because everyone begins with grandiose expectations that don’t happen overnight.

When we did season one of Cents Per Mile, we did a great job, but it didn’t get immediate grandiose results, so we took a four- or five-month hiatus.

Then people kept asking when season two was starting. The company we were producing it for initially canceled it, but then FreightWaves picked it up, and suddenly we were back on!

[00:06:03] Scott Feather: I love that. Reading about your launch of Brake Check, you mentioned how truckers have been forced to digest repeated narratives for years.

It read like an intervention calling out that things are different now. What makes this era different, and why can’t we just parrot narratives from five or seven years ago?

[00:06:55] Charles Gracey: I’ve always prided myself on being an outlier and doing things differently. Looking at other media outlets, there’s always an agenda or tone that doesn’t adapt to market cycles.

Everyone tries to force-feed the driver the same narrative regardless of reality, showing pie charts claiming everything is either awesome or terrible. But that doesn’t translate to the cab.

Right now, people claim it’s a golden era of freight and that “we’re so back,” but if you look at owner-operators’ bank accounts, they don’t feel “back” at all.

Expenses remain extremely high, and while rates are up, volume isn’t quite there. While others take victory laps, drivers are trying to survive while being force-fed narratives from pie charts.

[00:08:04] Scott Feather: It’s a data problem. Everyone talks about “more data,” but now people only look at data instead of talking to people on the ground writing the real narrative.

[00:08:27] Charles Gracey: Exactly. When times were great before the market dropped, people bought extremely expensive equipment despite warnings about market cycles.

They got crushed by their own expenses. Some expenses were controllable, like equipment choices, while others were driven by market forces.

When those problems compound, the body count rises. That’s why Brake Check was a call to action for me to connect driver conversations on Trucking Cents back to industry executives so both sides can meet in the middle.

Instead of yelling or pointing fingers, we’re seeing meaningful conversations where both parties start to understand the other’s perspective.

[00:09:44] Scott Feather: Love it. Do you think we’ll look back at mid-2026 as an era of overextension, or does what’s happening now have real staying power?

[00:10:00] Charles Gracey: My gut says we’ll look back at this as an industry-defining moment. Technology is a great tool, but it hasn’t reached the point of replacing people.

Until someone figures out how to move freight with technology and zero humans, companies have to focus on people. Rates are going up, but drivers aren’t moving because they know the grass isn’t greener elsewhere.

[00:10:42] Scott Feather: How high do pay packages have to go?

[00:10:44] Charles Gracey: Higher than where they’re at right now.

[00:10:45] Scott Feather: Yeah.

[00:10:46] Charles Gracey: If you want to retain drivers, pay them! Don’t post on social media saying “we’re family”, drivers have real families at home, which is why they show up to work.

Don’t claim you treat them like a name instead of a number when the first thing dispatch asks for is a truck number. Drivers have made peace with those facts.

Instead, pay them fairly for their professionalism, communicate clearly, and let them do their jobs. No driver stays for a retention bonus paid a year and a half later, and no one cares about an extra $150 a month. Give them consistent opportunities to earn, and they’ll stay.

[00:11:36] Scott Feather: Carrier companies and recruiters complain about signing bonuses and turnover, but if you take care of people and pay them well, you don’t have to worry about competing with signing bonuses.

[00:12:10] Charles Gracey: Coming from a recruiting background after driving and working in safety, recruiters often tell bosses to give them more marketing money to recruit.

Anyone can recruit more with more money, but we need to address why we’re losing people. Fix the hole in the boat before trying to bail out the water.

[00:12:43] Scott Feather: With an aging demographic of drivers retiring, how do we attract younger people to become commercial drivers?

[00:13:13] Charles Gracey: Don’t give me a nervous twitch by saying “driver shortage”!

[00:13:19] Scott Feather: How do we bring in people graduating high school or looking for alternatives to college, especially with fears around AI taking other jobs?

[00:13:42] Charles Gracey: First, we must address the elephant in the room. Looking at headlines on a random trucking news site: “Iowa 80 Truckstop owner passes away,” “No CDL and tampered logs: 350 violations discovered in three-day blitz,” “Semi-truck strikes bridge,” “Fentanyl seized during commercial vehicle inspection.”

That doesn’t sound attractive to a young person. We have to police our industry and make this a job worth wanting. As Robert Pierson from Mesilla Valley Transportation asked: “Is our baby ugly?” We must be honest with ourselves.

To hand this industry to the next generation, we need solid pay packages, sustainable benefits, clear career paths, and respect for drivers’ time. Younger generations want long-term career paths, homeownership, and financial stability, not just shiny objects.

[00:15:29] Scott Feather: Exactly, they want a career path above the poverty line.

[00:15:34] Charles Gracey: We can’t fake it until we make it; we actually have to make it.

[00:16:34] John Howland: How important are podcasts, radio, and social media platforms in bridging this gap and helping the industry evolve?

[00:16:45] Charles Gracey: To quote Spider-Man: “With great power comes great responsibility.” It depends on how you use it. If you use media to genuinely bridge gaps, it’s a powerful tool. If you just push echo-chamber propaganda, it will backfire.

My focus is to put out driver-focused, authentic content. I inform and entertain using energy and passion to get people talking about hard topics.

[00:18:43] John Howland: What uncomfortable conversations is the industry still avoiding?

[00:18:59] Charles Gracey: Expectations. Market power shifts back and forth between carriers and drivers, but there’s always a lag in understanding who holds control. We’re currently at a middle point, a Mendoza line, where neither side has total control.

This is the perfect starting point for transparency. Carriers and drivers need to lay their cards on the table and communicate honestly rather than playing games.

[00:20:36] Scott Feather: We tend to obsess over extremes, assuming it has to be either a carrier market or a driver market, instead of finding a balanced middle ground.

[00:20:59] Charles Gracey: If both sides realized shippers need to step up and pay fair rates, we’d be in a much better position.

[00:21:11] Scott Feather: Shippers love watching carriers and drivers fight each other while rates stay low.

[00:21:18] Charles Gracey: With recent regulatory rulings, a lot more attention is finally turning toward shipper accountability.

[00:21:25] John Howland: Scott, let me ask one more question before moving to the lightning round.

[00:21:38] Scott Feather: What industry trend concerns you most over the next year or two?

[00:22:13] Charles Gracey: The unchecked speed of technology adoption keeps me up at night. I’m pro-technology when it enhances efficiency, but against technology aimed at replacing human connection. For example, drivers do not want to interact with an AI recruiter.

Automating recruiting eliminates human pushback and leads to poor matches, worsening driver turnover. Tech should be a tool to empower people, not replace them.

[00:23:53] Scott Feather: It feels like people use AI as an “easy button” for everything instead of where it actually makes sense.

[00:24:03] Charles Gracey: Exactly. Tools like Truckstop’s Ava enhance the driver’s experience and let owner-operators compete at a mega-fleet level. That makes sense. But replacing recruiting departments with AI auto-dialers at 5:30 AM just alienates drivers.

[00:25:00] Scott Feather: Nobody wants to be recruited by a machine.

[00:25:12] Charles Gracey: Sitting through automated phone prompts during a workday just makes people look for the opt-out button.

[00:25:24] John Howland: You can always tell by that awkward pause after you say hello!

We’ve reached the lightning round! Quick-fire answers under thirty seconds. If animals could drive trucks, what animal would you be, and what animal would be the best driver?

[00:26:01] Charles Gracey: A gorilla!

[00:26:02] John Howland: Any reason?

[00:26:03] Charles Gracey: What’s better than pulling the air horn and pounding on my chest? Plus, imagine the comedy value for kids watching a gorilla fit in the cab!

[00:26:24] John Howland: Who is someone in the trucking industry doing great work that more people should follow?

[00:26:26] Charles Gracey: Paul Gibson! He’s the unsung hero who constantly advocates for the driver community behind the scenes.

[00:26:58] John Howland: That wraps up today’s episode. Charles, thank you so much. Scott, thanks for co-hosting. This is Behind the Freight, and we are out!

[00:27:10] Scott Feather: If today’s episode helped you think differently about your operation, share it with someone in your network who needs to hear it.

[00:27:16] John Howland: And if you’re looking for tools to help keep your trucks rolling, from finding quality loads to getting paid quicker, truckstop.com is here to help.

[00:27:25] Scott Feather: Go visit truckstop.com to explore the load board, rate insights, and risk management solutions built specifically for carriers and brokers.

[00:27:33] John Howland: Thanks for listening to us at Behind the Freight.

[00:27:36] Scott Feather: Until next time, keep the wheels turning…

[00:27:39] John Howland: …and the bad loads burning!