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Todd Gilliland should be smiling — he's sitting 20th in the standings and recently signed a contract extension with Front Row Motorsports.

The 24-year-old Gilliland is considered one of NASCAR's top prospects after winning back-to-back ARCA West titles in 2016-17 and finishing second in the ARCA East standings in 2017, but it hasn't been an easy road for him.

He won just two truck races and finished no higher than 10th in the standings driving for powerful Kyle Busch Motorsports from 2019-2021. Left without a ride at age 20, Gilliland landed with Front Row Motorsports to drive a truck in 2021, winning one race and finishing seventh in the standings. Front Row elevated him to Cup, where in the past three seasons he has one top-5 and eight top-10 finishes.

But he has progressed, with an average finish of 23.2 as a rookie, 22.0 last year (where he also ran a handful of races for Rick Ware Racing as FRM replaced him for select events) and now 20.1.

After two seasons of finishing 28th in the standings, to currently sit 20th is a jump not often seen.

The third-generation racer is the son of David Gilliland, who owns a five-car truck team, Tricon Garage, that has Corey Heim with a series-high four wins this year.

FOX Sports caught up with Gilliland for a couple of questions after his contract extension announcement and then for an extended conversation last week prior to the race at Iowa to talk about going from a star prospect to finding his footing in the Cup Series.

What's it like to know you went from a guy who didn't have a full season in one car last year to a guy who is now set for a couple more years?

From my side of it, I need to be reminded of that, for sure. It's definitely a huge blessing and a huge opportunity to be able to continue racing in this series. And I definitely know that you can't take it for granted. I forget last year, it was piecing together a full season. Just to see how things changed, see how much results can sway things good or bad very quickly in the sport shows that we need to continue improving and stay on top of our game. I'm super thankful, super excited to continue with Front Row.

Last year, you wouldn't even be part of the top 25 media availabilities where we are talking now.

Just how much better we've been running is super exciting. At some point, we definitely struggled and knowing that at that point, you question everything — this isn't any fun, I'm not doing anything good for anybody. You can definitely look yourself in the mirror and say, "Do I even need this opportunity? I'm doing nothing with it." But I'm very thankful that I feel like it's changed a little bit, that I feel like we go to the racetrack and contend with the best guys.

Have things now been any more calm for you or any more settled for you knowing that your future is settled? Or is it never settled?

I think that the second option is more true. The second you probably feel like you know what your future is when it all goes crazy and it all changes. The biggest thing, though, is just feeling the belief behind me of my race team, of our owners, managers, everyone at the shop that believe that I can continue this growth for the next few years and just continue to be a guy that hopefully keeps getting better. Even if that's [just] the common consensus within the shop, that's a good thing for now. You definitely never feel too comfortable, but I'm just happy with our progress as of late and happy to think that our ownership and everyone at the race shop believes in me going forward.

Your granddad was a driver, your dad's a driver. Did you ever have any choice?

That's funny. I don't really think of it as that. I definitely, obviously, grew up in it. The story my family tells me is I went to my first race at like 2 weeks old on the West Coast at like Irwindale Speedway, somewhere out there. It's crazy. When you grow up around something, it's not like it's your only option, but I feel like you just have such a deep understanding of it and you just develop such a love for it. I watched my dad and maybe not as much watched my grandpa but obviously heard stories. My dad's definitely my hero, growing up and watching him do it, you see the highs and lows of it and it makes you appreciate it as a young adult. At the same time, it definitely gives you a real appreciation and love for wanting to do it yourself. 

How much advice do dad and everybody give you or are they good about staying out of your ear?

My dad is definitely not as involved as maybe he once was or maybe other families are of people that you see or hear about. Obviously, he's really busy with his own stuff at the moment with a five-truck team. And it's really cool to see him doing super well. We talk a lot, whether it's about his stuff, our stuff, all that stuff. It's definitely really nice to have some common ground to talk on. But at the same time, more recently we've been more just talking about normal stuff, father-son stuff. He's more of a guy, if I ask him a question, he'll always give me a really detailed answer and go really in-depth. But he's not one to maybe just give me advice out of the blue. 

You see Austin Dillon racing for his family and everything. Is it comforting in a way not to race for your dad?

There's positives and negatives. For me, the biggest thing is having relationships within the sport. Whether that's me growing up, walking around the garage, knowing people for 10-plus years, even though I've been racing for only three years in the Cup Series. All that stuff really helps when you're talking [to teams]. I'm with [Kevin Harvick's] KHI Management now; for a while my dad was doing it, and I think that helps just having some sort of reputation in the garage is always a good thing. I've only ran one race for my dad, and it was the truck race a couple years ago, and we were able to win it. So maybe that's just how we go out, go out for good, and we will forever have won our one and only race together.

That win in 2022 at Knoxville was your last NASCAR win. 

That's crazy. Time has flown by.

So is it hard not to win? 

Absolutely. That's the hardest thing. It's super tough. You have to balance your expectations. The last few weeks, in my eyes, we've made progress. We've finished in the mid-teens. But at the same time, that competitor in you is still extremely frustrated with that. That's not what you grow up necessarily wanting to do. You want to go out and win races and compete for wins, stage wins, lead laps, race against the best of the best. And I think in everyone's heart, in my heart about myself, I feel like I can do that. It's all about building, building a process and building with the team, getting more experience on my end. But it is extremely tough not to win. Definitely, the goal is to get to to that stage sooner than later.

In trucks, your average finish is around 9.1. Then it Cup it goes from around 24 to 22 and now 20. And that's progress, even though it's probably hard to see it sometimes?

Absolutely. With that stuff, it really goes to having a good support system around you. Some weeks, I just get so frustrated that we're not doing what I feel like we could be or could have on any given weekend. But it's all about the bigger picture, whether that was gaining experience for the first year to now I feel like we really needed to start making progress and running better. It's very tough. It takes a toll on you. And I was even watching [Martin] Truex's [retirement] thing and he's like, "On the seasons where everything's clicking and going well, it seems like it blows by." That's not so much our case. I feel like we're scratching and clawing every single week. It's tough to keep that mental focus, but it's obviously the most important thing.

In 2016, 2017, 2018, everybody's saying you're the next greatest thing. Me probably included. So, at that time, not that you're thinking it's going to be easy, but I don't know that you could have envisioned the last four or five years?

Exactly. That's what also made the couple of years at KBM that much tougher on me [with] the media, everyone. I came here to Iowa two times and won my first two times here [in ARCA West], and it doesn't seem like it's going to be that hard. You're young, probably a little bit naive to everything, the challenges ahead. That's a super hard thing to go through. I think every young driver, for the most part, goes through it. There's a lot of younger guys that look extremely strong and obviously, everyone has a lot of potential. And then you move up, it seems like half the guys are where they looked like they were going to be. And then another step, and it's like another half. 

It's crazy how that goes. I think that was probably the hardest thing for me is going through, like you said, where you think you're going to be the next guy that's going to win everything to realizing it's going to be a lot more of a challenge. I still think we can do that. But it's just going to be more of a process and a lot more learning curve. It definitely made the last four years tougher, but I feel like I'm definitely past that and I feel like I'm just more focused on myself now.

I look at your Xfinity stats and I'm surprised. Because there are none. Is it wild that you haven't raced in the series at all?

Yeah. I've never even sat in an Xfinity car or anything. Definitely, I guess, kind of the unconventional approach. But we've seen more guys do that recently. [Carson] Hocevar has done it and been really good. It doesn't seem like he's really missing any huge steps by not. Zane Smith, obviously a truck champion, is looking super ready and he's done a good job. 

With the new [Cup] car [for 2022], for me, that's kind of why the timing was how it was, obviously an open seat in the Cup Series with a brand new car, you wanted to get in as soon as you could so you could get on the same level playing field as everyone else. I'm super thankful I did that and had the opportunity because I feel like anyone coming in now, it's an even steeper learning curve. It's definitely tougher for newer guys coming in. But at the same time, to me, I feel like a truck and a Cup car drive very similar. The restarts are all momentum-based. If you lose a little bit of momentum on exit [of the turn], you're getting swallowed up by three or four cars, three- or four-wide going in the next corner. To me, there's a lot of resemblance. Obviously, I have nothing to go off of for Xfinity, but to me the cars drive very similar. 

You don't know who your two teammates will be next year. But are you be ready to an elder statesman, or the leader or the veteran with Michael McDowell leaving at the end of the season?

Yeah, I'm ready. It's going to be a lot. If this was last year or my first year, I would have certainly not been ready and I would have known that and have been super nervous about it. But now I'm really excited about it. I think it's a good opportunity. Obviously, I've known everybody at the race shop for a long time. .... It's all the stuff I've seen from McDowell over the years — the constant push, whether it's uncomfortable for him, for our team, it has to be done and I think it's to a point where I'm definitely ready to do it. Still a lot of unknowns, but I'm super excited to see where the progress of our team takes us.

Bob Pockrass covers NASCAR for FOX Sports. He has spent decades covering motorsports, including over 30 Daytona 500s, with stints at ESPN, Sporting News, NASCAR Scene magazine and The (Daytona Beach) News-Journal. Follow him on Twitter @bobpockrass.

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