023: Pumped To Be A Pro - with Duncan Littlefield | Sport Coats Podcast

A podcast fueled by professionals bridging the gap between Sports and Business. Enjoy as guests share stories & experiences from the playing field to the board room.

023: Pumped To Be A Pro - with Duncan Littlefield

Meet Duncan


Duncan, formerly a professional golfer currently serves as CEO of Littlefield, a company that owns a variety of other companies as well, such as the Littlefield Company, Paper Airplane, Large Forests, Sidecar, and is a critical equity partner contributor to profit focus startups. Duncan's mission is to always be a part of a larger conversation and to support everyone to become obsessed with their life. 


Since we’re in the middle of the Olympics, I’d like to start off by asking you about your opinion on golfing in the Olympics.


Initial thought on golf in the Olympics is I love it. I think it does so much to expand the game because it connects to audiences. You look at players in there that have recently said that it's one of the coolest things I've ever been a part of. Because you look at the team sports where they represent their country, Ryder Cup, Presidents Cup where it's a 12 man team with a captain and vice-captain. It's really fundamentally different. I don't think that they have the correct format. That's my opinion. I think the way they source players is a very fascinating way to look at it. and I know a lot of people on the back end when they were first bringing it to Rio spent a ton of time examining it, where they went through going, "Hey, if we went this route, who would be in it?" I think they have it close, but I think there are a few ways to make golf better in the Olympics, to embody the game of golf, but also to embody the Olympics as an overall organization. So I think they're close, but it's a pretty special space. Again, using the example of 2020 Tokyo is you watch seven guys go into a playoff for the bronze medal, and they fought for that. That was amazing and I'm not saying like Xander taking gold was not the highlight because I think the storyline for Xander was just spectacular. But the reality is seven guys going into a playoff to fight for the bronze medal was riveting, like absolutely riveting. I'm so, I don't wanna say happy that it came out this way, but I think for C.T. Pan to win in the fourth playoff hole, taking down Rory, I think it's awesome. So the game of golf is in a good place, but I think golf in the Olympics is really special and it's only getting better.


If you were on the Olympic Committee, how would you improve the golf event?


I would take it into a five-day event and I would model it after what they do at the USGA, US Junior Tournament, where they play a 36 hole qualifying stroke play to then go into singles match play. I would really like to see that the only other kicker because they also do this with college golf now, in the playoff where they take all the teams, they go match play for two rounds, and then they go down into an eight-team match-play bracket. I think if you do a very similar structure, then it offers everything you want it to, but also it keeps some core, old school golf tradition in the mix, but then it also kind of embodies a little bit of the Olympics as well. You look at swimming, for example, how you go qualifying down into the major heat, and I think it keeps aligned with it. But then you can also crown a team champion as well, long term. So I think a 16 man field or women's field is good. I think that you potentially could have it where you have a team event attached, where you at least have two representatives from every country, and potentially an A and B team, from the major countries that would represent. But then at that point, I think you can also play a team route into this if you even open it up to maybe 80 players in that space to then get it down to a field of 16 to play match play after.


Not often have I heard about the process of someone going from a professional golfer trying to achieve their amateur status back right. How does that work?


The process is you write the USGA saying, "Hey, I would like to receive my amateur status back," and normally, depending on where you sat in the world rank you go into a two-year waitlist. So you have to kind of say that you're taking a two-year ban from playing competitively and from there, then you receive your amateur status back. So you get a letter from the USGA saying, "Hey, we've recognized that you've really committed to taking your amateur status back, you have gotten your amateur status back." Now, if you ever want to go professional again. So if I went from a pro to an amateur, and then went pro, again, I can never go back to being an amateur after the second time I turned professional. So that's the kicker, but it's a two-year process you write to the USGA, you do all the paperwork, you fill out when your last tournament was, what your world rank was if you get if you received one, all that, and then two years and you're back on it.


Could you tell us a little bit about your golfing journey?


I mean, the reality is that when you're trying really hard to achieve something really big, and you have to go through the ups and downs like you have to go through it. But when you put everything on the line, and you bet the house on your game, you put the house in yourself, there's really nobody to turn to but yourself. I had a phenomenal support team around me, my parents were so encouraging. The only time it was negative was when I wasn't putting the effort in. Like that was the only time it was ever negative, or not positive. My coach was great. Yeah, I had a great group of people, like  PGA veterans that were mentors of mine. I got really lucky and I truly say that I feel like I'm one of the luckiest people to ever walk this earth and I'm definitely not letting it go to waste. But the peaks and valleys were amazing and I say that with a laugh, because the reality is that as a Mini Tour player, when you're driving cross country, you play a tournament in Georgia, and next week, you got to get to Washington DC, or you got to get to Bangor, Maine there's a lot of windshield time. There's a lot of road time to think about life, your game, what's bad, what's good, all the above and I think that's really helped me become the person I am today and not so much of what happened on the course, but what happened, when I actually had time to process it. I took the traditional Mini Tour route. The reality is back in the day, everyone goes like, "Alright, what would you have changed?" And I said, I would have changed two things: I wouldn't want a few more times, no question about it. But the only other thing I would have changed is how I invested. So now looking as a business owner, I recognize the differences of how I would have invested into my last career of being a professional athlete, compared to what I did. So right now, like when you get on to the Mini Tour status, is the only thing you hear is just make your dollar last the longest. Just make it last because the reality is that the average PGA Tour pro is about 31 years old. When you look at that, when you walk out of college, when you turn professional, whatever it is, it's like you're sitting back, you're going, Okay, I gotta make this last the longest. You know, it's peanut butter and jelly sandwiches, it's sharing a hotel room with four guys, it's cutting my costs down as much as I can to get to the 38th tournament of the year to give myself one more chance compared to investing a little more and not having the entry fee for that 38th because you can only get to 35. So for me now recognizing how I invest in the business here, I would have put a little more into myself. I would have eaten a little better, I would have stated a little nicer of a hotel, maybe had three roommates compared to four, or vice versa. Because then at that point, I would have been able to maybe show up a little better compared to just absolutely grind it out, I maybe would have shown up a little better. That's where I would have invested in myself a little differently and I'm recognizing that in business now, where I don't hold on to big money. I definitely don't spend it like it grows on trees, but I'm a little more aggressive right now than I was back in the day and I wish I recognized that earlier, where I could have invested a little more of myself.


What kind of recommendations do you have then for being money conscious, but at the same time, not holding on too much that you're actually doing yourself a disservice?


At 25 or 24, you think you know everything about the world. I did. Like when I was 23, and professional golfer, like, I thought I was the guy. I thought I was the guy who was just gifted and talented and I was bound to be great. I worked really hard at it. When you're 23 years old, and a professional golfer you have to have a little bit of cockiness to yourself. But like, most 23-year-olds don't know who they are. So it's like, for that same point, I didn't know who I was. I thought I needed to walk into the room and have everyone recognize that I was a professional golfer. It didn't matter who Duncan was, what mattered was I walk in the room, and they go, "Oh, he's sponsored." I did a lot of things really well. Now, if I went back into the game right now, I really believe that.


I feel like when we talk about investing in ourselves, it's so easy to think of it as a monetary thing, as opposed to an investment from so many other grounds.


Right! Right now, one of my favorite quotes that I've really held on to recently states, "Just because you can carry the weight well, doesn't mean it's not heavy." So for me, I know I carry weight well because around my company, I have to carry the weight like no one will outwork me and my company. No one should ever outwork me in my company and I own that fully. It's not a pissing battle, but the reality is that I should outwork everybody in my company and I'm happy to because I love what I do. I love who I get to serve, I love the stories we get to tell, I love building the business that I see. But to carry the weight for everybody else is a lot, to carry the weight for my team members, to carry the weight for my wife, to carry it away from my family and friends. It's a lot when you're trying to grow business and you also have families who really rely on your vision and rely on your leadership. So what I found is that if I give myself about two to two and a half hours in the morning, for myself, I'm good for the rest of the day no matter what. So what my routine is I get up at 4 am. I'm in the gym by five, at that point I work out for anywhere between 30 and 60 minutes. Now at that point, I get into a sauna for 15, I take a cold shower, I have breakfast, and I am ready to rock by seven and I can carry the weight for everybody else. But if I'm not selfish enough to do that every morning, I'm not going to carry the weight as well as I should and that's where you have to be selfish for yourself because that is arguably the least selfish thing you can do because you're showing up for everybody else in the best way possible. So you know the investment into yourself is the least selfish thing you can do. Even if it's five minutes a day, if it's 10 minutes of meditation, if it's a journal, if it's prayer, whatever you want to call it, if it's legitimately a $6 cup of coffee every single morning because that sets your day correctly to show up for everybody else for the other 23 hours and 55 minutes, but you have that five minutes of a $6 cup of coffee that you enjoy thoroughly, then it's worth every $6 cup of coffee every single day of the year, because you're showing up the right way for everyone around you. So you can carry the weight of other people. The world's heavy right now. COVID has been heavy. Everything going on, it's changing, it's evolving and if we can't show up for ourselves, we can't show up for our people, then you know what? If a $6 cup of coffee is the best investment that you can make and just make it a priority for yourself and own it and just know it. Call it as you see it be vulnerable and budget that $6 cup of coffee every single day because it is the exact thing I need to show up and I will do everything in my power to work around it to make sure I can get that for myself. That's called investing in yourself. It doesn't matter what investing in yourself looks like for you, but know what you need to show up. Know how you get to that start line every single day.


And make it your own, right?




And so much more...