Trent Dilfer was the starting quarterback for the Baltimore Ravens when they won the Super Bowl during the 2000 season. Dilfer attended college at Fresno State university and was the No. 6 overall pick in the 1994 draft by the Tampa Bay Buccaneers. Dilfer went on to play for the Seahawks, Browns and 49ers during this NFL career.

Dilfer was a Pro Bowler in 1997 and was a recipient of the Bart Starr Award in 2003. He has worked at ESPN as an NFL analyst and is now currently the head football coach at Lipscomb Academy in Nashville, Tennessee.

In this interview Trent and I discuss learning from veteran leaders early on in his career, things he learned from Tony Dungy and a story about Ray Lewis’s competitiveness.

SHAFIN KHAN: Who were some of your idols growing up?

TRENT DILFER: I was a big [Roger] Staubach fan, then an Aikman man. Eric Dickerson, Walter Payton, Steve Young. I just liked different players, I liked how they competed usually. I liked the grittier, tougher blue collar guy. It was kind of what I gravitated too. I was a huge basketball guy too, Wayman Tisdale was probably my favorite athlete of all-time for whatever reason.

KHAN: Were you ever able to ask any of these guys for advice?

DILFER: I talked to Joe Montana before I entered the draft, he helped me with some stuff. Warren Moon and John Elway, I talked to them a little bit before I entered the draft but not really before that draft period of time.

KHAN: What type of advice did they give you?

DILFER: Well, mainly it was just the business of it and the job of it. How to be mature, how to help your teammates and how to handle your financial situation. The football advice stuff, I think we all tend to not give too much football advice because we want to defer that to the coaches but most of it was to keep a good head on your shoulders, be a great teammate and take care of your business off the field. Just your typical stuff.

KHAN: What was the biggest challenge you faced during your career?

DILFER: There were a lot. My career was very up and down. The whole thing is challenging. It’s challenging to be a young teen or 22 years old and be the leader or supposed leader of a football that had a bunch of men on it. There was challenges of learning how to start a family when you are young and going through the rigors of the NFL. I think there are the challenges of learning how to handle your setbacks in a public forum. So, if things don’t go well, everyone knows about it because of the media. Team dynamics can be challenging. It’s just the game. The NFL game is just a challenging game so every week you have different things you are faced with that you have to overcome.

KHAN: Were there veteran guys in the locker room at the time that were able to give you advice and help you?

DILFER: Yeah, I had good mentors. Paul Gruber, who was a veteran offensive tackle for us helped me a lot. Hardy Nickerson was a guy I leaned on. John Lynch and I were kind of growing up together in the league. He’s one year older than me so me and him tried to figure out a lot of stuff on our own as we were starting families and trying to figure out the NFL. So, I kind of grew up with John Lynch. After four or five years in the league even though you are only 27 or 28 years old you are kind of forced to be a veteran. By then I had enough tools that I could kind of lean on my peers more than the guys that were older than me.

KHAN: What life advice do you have for a young man?

DILFER: Look for hard things. I think we are in a generation that looks for the easy way out, looks for the common way of doing things. I’m not trying to be the curmudgeon and say that every young person is an idiot. It’s just this generation. You guys are taught to be like “Okay, there’s the answer. Stamp it and move on.” There’s a deeper learning, there’s a deeper maturity that comes with the process of finding hard things. So, find the steepest hill and go climb it and you’re probably going to fail. Most likely you’re going to fail but that’s good because you’ll learn so much through that. You’ll learn how to be resilient, you’ll learn how to be gritty. You’ll learn how to endure more and those are principles that are more important than production at 24. So, we talk a lot about doing hard things, finding hard things to do. We talk a lot about lonely work, what are you doing when nobody is watching. It’s really easy to check the boxes on “hard work” the work that is expected but do the stuff that no one expects when nobody is around. Find things that make you uncomfortable. I appreciate that you’ve hunted me down, that’s not easy to do. So, find the uncomfortable thing and kind of live there. If you do those things, you’ll look back in ten years and be like “Holy crap, how did I become a millionaire? How did I become a Pulitzer prize winner? How did I do these things?” Well, because you climbed Mount Everest. You fell down seven times on the way and had to go climb it again.

KHAN: Which coach taught you the most?

DILFER: I feel like I cheat coaches if I just give one. I’ll give you a good answer. I think the best thing I’ve done as a learner is I’ve taken the best from so many people I’ve learned from. So, there are a lot of things I didn’t learn from Mike Holmgren but there some great things I learned from Mike Holmgren and I took the best things. Tony Dungy. There were a lot of things I would do different than Tony Dungy, but boy does he do some things better than anybody else and I learned those and applied those. Jim Sweeney, my college coach was an incredible leader and I learned a lot of leadership principles from him but there was a lot of stuff I wouldn’t do that he did. Jeff Tedford, who was my offensive coordinator in college who has been a very successful college and NFL. I’ve taken his best stuff. Clyde Christensen, who coached Peyton Manning at the Colts was my coach before Peyton, learned a lot of stuff from him. Brian Billick, who I didn’t get along with great but he did some things really well and I took those best things that he did and applied them to my life and my career. So, I’ve kind of looked at it that way. I’m not trying to be like anyone that coached me. I’m trying to take what they did best and put it altogether.

KHAN: What are a couple examples of things that Mike Holmgren and Tony Dungy did better than everyone else on the football field?

DILFER: I think Holmgren was the best I’d ever seen at taking complex things and making them simple. Football can be really, really granular and he would say “Stop it!” Stop overthinking it. It’s literally fifth grade math. Let’s take calculus and turn it into fifth grade math and you’d have that “Ah ha!” moment once you did that. I think Dungy was the most poised. You know what Tony did, he could handle a lot of drama because he was just so poised but in the midst of that he also didn’t let little things become big things. So, he could look at a guy that was habitually late, lets take Warren Sapp. Instead of making that a giant thing “Oh my god Warren Sapp’s late, it’s the end of the world.” He would handle Warren behind the scenes. He would parent him, coach him up so that it wasn’t a distraction long term. So, a little thing didn’t become a big thing. He could handle a defeat where I threw three interceptions. He wouldn’t let three interceptions become thirty interceptions because he would deal with the actual reality of that game and not let a little thing become a big thing.

KHAN: What is your favorite memory from your career?

DILFER: I have a lot of them but my favorite would probably be winning the AFC championship in Oakland. I have a picture that hangs on my wall of me and Ray Lewis hugging and we both looked at each other and said “Oh my gosh, we did it. We’re going to the Super Bowl.” That’s kind of my most meaningful vivid memory.

KHAN: What is a good Ray Lewis story that you have from the 2000 season?

DILFER: One of the games we played was a lot of us would go to the cold tub after practice to get our bodies right. We were all so competitive, we would see who could hold their breath underneath the cold water the longest. It would make Ray so upset when he didn’t win, he would lose his mind when someone would beat him, when someone was tougher than him and could go under the cold water longer than him.

KHAN: Talk to me about getting into a fight with John Randle and getting ejected, what prompted that?

DILFER: I mean I was a hot head. I learned a lot early in my career about not being a hot head but I was a real hot head. He had been getting in my head during the game at the line of scrimmage, just saying stuff to me and he had cheap-shotted me earlier in the game and said he was going to do it again, saying “I’m going to get your knees, I’m going to get your knees.” On that play I was rolling out to my right and he kind of went low on me and got me and I just lost my mind.

KHAN: It’s known publicly that you have worked through some personal issues in your life. Who would you credit that helped you rise through tough times?

DILFER: Matt Hasselbeck had a huge influence on that. A man named Clyde Christensen who I mentioned earlier who was a coach of mine in Tampa has been a mentor and helped me a lot there. There has been lots but I would point to those two directly.

KHAN: Lastly, what is your Super Bowl prediction for this year?

DILFER: I’m going to go Saints and I’m not going to go against the Patriots. I’ll go Saints vs. Patriots.