Craig Kessler on The Dad Advice Project and Building a Powerful Legacy – EP 31

Craig Kessler on The Dad Advice Project and Building a Powerful Legacy

Today, I’m speaking with my friend Craig Kessler. Craig is the COO of a multimillion dollar company, Topgolf, which is one of the fastest growing sports and entertainment companies in the world with over 60 venues across the US and nearly 20,000 associates. 

Before he joined Topgolf, Craig cultivated extensive experience in the world of private equity, which helped him prepare to serve as one of the youngest C-suite executives in the country.

Craig’s also just released The Dad Advice Project — a book of real-life stories and advice written by more than forty dads from all walks of life. It’s a powerful behind the scenes look at raising a family and being a great father.

Today, Craig and I dive into a bunch of topics, including the risk/return of private equity investing, the power of culture, mentorship, work/life integration, The Dad Advice Project, and how to think about building your legacy!

Key Takeaways with Craig Kessler

  • How Craig got his foot in the door at Topgolf, rose through the ranks, and came to become COO of Topgolf in ten years.
  • The importance of doubling down on company culture, no matter what your role is. 
  • What Craig learned from asking 42 of his close friends for dad advice–and how these letters took shape as his new book.
  • The two things Craig discovered every child needs to hear and see from their parents. 
  • What it means to leave a legacy behind in this world–and the value of small, good things in difficult times.

Clips From the Craig Kessler Interview

Craig Kessler Tweetable

“There is no perfect. Just keep swimming, just keep trying, and you'll get there.” - Craig Kessler Click To Tweet


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Read the Full Transcript with Craig Kessler


Justin Donald: Well, Craig, I am so excited to get some time here. You and I visited a while back. And it’s really cool how we met. We have a mutual friend, Jeff Woods, and he said, “You guys have to meet up. You guys are going to just hit it off.” And I’m so glad that we did. And I’ve been looking forward to this time. So, welcome to the show.


Craig Kessler: Justin, it’s good to be here. And like you, I’m very grateful. Our good friend Jeff Woods connected us.


Justin Donald: Well, he is definitely just a bundle of energy and joy. And so, I’m very pleased. I was on his podcast a while back one thing. And they just do such incredible work. And so, I know any time I get a recommendation from him, it’s always going to be a good one, and it has been. I’m so thrilled about getting to know you and learning your story and seeing all the moves you’re making to positively impact and change the world.


Craig Kessler: Well, I appreciate it. Let’s jump in.


Justin Donald: Cool. I love it. Well, first and foremost, I’m curious kind of how you got to where you are today. You’re a very successful guy. You’re very young to be running a massive multimillion, multibillion-probably-dollar company as COO with Topgolf. And by the way, I love Topgolf. We just went to the one in Vegas and we were there for one of my buddies. It was supposed to be his 40th birthday, my buddy John Ruhlin, and we were celebrating that, but COVID kind of put us a year off. So, it’s his 41st birthday. And we just had an incredible time at your– I would call it, one of the nicest, if not the nicest one, I’ve ever been to, with swimming pools and hot tubs and the whole nine yards. I mean, it’s an incredible spot. So, I just wanted to say, bravo, what a great concept. I love going, I love playing. I’m very competitive. It’s just wonderful.


Craig Kessler: Well, thanks, Justin, first of all, for visiting, for having a good time. Topgolf Las Vegas, it is definitely our flagship venue and we’re proud of it. To answer your question, how did it all come to be? I don’t think, I know it’s a massive team effort to get to where we are. Topgolf has over 60 venues across the US, nearly 20,000 associates. We’re growing like wildfire both domestically and abroad. And this is an absolute world-class team that’s turned the business into what it’s become.


Justin Donald: That’s great. And so, you’ve been growing a lot here recently, but I want to know how you’d even gotten to a point to grow with the company. Like, how did you get your foot in the door?


Craig Kessler: Yeah, I’ll give you the 30-second backstory. Truth be told, born and raised in San Diego, went to college in Washington, D.C., wanting to be president of the United States. And within like three weeks in D.C., I wanted nothing to do with politics and really hadn’t looked back ever since. And towards the end of college, I had a choice between two different job offers. The first was to be a movie producer, and the second was to go into consulting. And I flipped a coin. I really couldn’t decide. So, I flipped a coin, and it landed on the movie producer side, but truth be told, and I think it’s probably because I came or come from a family that didn’t have a whole lot and I was very risk-averse.


I found myself rooting for the coin to land on the business side. So, I went with my gut and ended up joining a consulting firm, moved around the world for a handful of years, and eventually found myself in private equity. And it was an unbelievable Navy SEAL-type boot camp in business, learning how to evaluate businesses and help them grow. And one thing led to another. And over the course of 10 years of my career, I wound up at Topgolf. And I’ve been here for almost five years now.


Justin Donald: That’s fantastic. So, this world of private equity is kind of a whole nother world. And I think most people don’t recognize or understand even what that is or what that means. I would love for you to elaborate because people always talk about PE or private equity, or my company just got bought up by a PE firm. I’d love to hear your explanation of what that is, being an insider.


Craig Kessler: Here’s the simplest way I can describe it. I would imagine most of your listeners are familiar with the concept of flipping houses. So, when you flip a house, there are really three things you do. You buy a house, you make it better, and then you sell it. And hopefully, you make a little bit of money along the way. Private equity is the exact same thing as flipping houses, except it’s companies we’re dealing with instead of homes. So, you buy a business, you make it better, and then ultimately you sell it, hopefully for a profit. And my job, I work for two different private equity firms, KKR and Providence Equity. My job was to do the first two of those three buckets, find good companies and make them better.


Justin Donald: That’s awesome. And so, in the whole big picture scheme of things, I just want to kind of lay out for our audience, you’ve got the early round investors, like your angel investors who invest in seed rounds. And they don’t invest as much and it’s pre-revenue generally. It’s like a super early stage. Sometimes it’s like the concept isn’t even proven yet. And then you kind of get into the world of VC, venture capital, and they don’t like seed as much. They are more on kind of the series A side or proven track record. Something, whatever you think should happen is already starting to happen. There’s some revenue coming in, etc.


And then, the next stage is kind of private equity, where there is a track record, there’s profitability, everything is known, and they want to come in and they want a 10x or greater on that. And so, I’m curious if you have any thoughts around that based on kind of how I laid it out.


Craig Kessler: I think you gave a great summary. The only thing I’d add is as you move up the value chain from angel to venture capital, the private equity, the risk comes down and the returns also come down. So, it’s sort of like the best analogy I can think of is think about playing roulette at a casino. If you put $5 on red or $5 on black, and you effectively are betting on half the numbers on the table, the payout is only two to one, but if you bet on a number, you pick 31 because that’s your lucky number and it hits, the payout is 35 to 1. So, the more risk you take, the more reward you should expect in return. The caveat is you’ve got to be comfortable with losing because the riskier bets don’t always pay off.


Justin Donald: Yeah, that makes sense, and that’s really good elaborating on kind of what it looks like. And yeah, it is riskier on the seed stage, and I know private equity doesn’t have as much of an appetite for that risk. They love cash flow, they love profitability, and they want to pay. Generally, they’re pretty– my experience has been that PE firms are pretty generous in their valuations because they know what they can get it too.


So, you’re working for a couple of different PE firms. When did you decide to make the leap or I guess, was there a connection from the firm you’re with, with someone in the C-suite at Topgolf, or what did that look like?


Craig Kessler: Yeah, back to your question from earlier. Craig, how did you end up where you are? One of the answers is a whole lot of luck. And the truth is, when I was working in one of the PE firms I mentioned before, Providence Equity, Providence invested in Topgolf in early 2016. And my wife and I, our one son at the time, we’re living in New York City where I was based. And my job for the next seven or eight months was to fly every week from New York to Dallas, where Topgolf is based, really just to help Topgolf grow. And I fell in love with the company, I fell in love with the leadership team. One thing led to another, and they asked me to come on board as the Chief Operating Officer around Thanksgiving 2016.


Justin Donald: That’s cool. And so, you’ve got to be one of the youngest people in the C-suite and you find yourself running just a massive company. I mean, at first, was that a little intimidating and nerve-wracking? Or did you just feel like you had the tools and the skills to be able to do it? I’m curious.


Craig Kessler: I think, and it’s hard to remember and be totally objective going back almost five years, but here’s what I remember. I remember it being a tale of two cities. On the one hand, it was comfortable and welcoming because I had gotten to know the management team in the business for seven or eight months leading up to when this became official. And again, I fell in love with the team. I believed in the group’s capabilities and it was just a genuinely good group of people. So, in that sense, it was great.


On the flip side, I was 31 years old at the time. There were, I don’t know, 5000, 6000, 7000 associates, and I had a lot to learn. And my head was spinning for days on end. And it took me a while to, I think, build trust with all of the right people so that we can work together collaboratively. And honestly, it took a while for them to have faith in me. And I think one of the things that I learned is if you show up, you work hard, you’re humble, you ask questions as opposed to dictating a plan of attack, and people see you’re leading with both your head and with your heart, it’s amazing the doors that will open. And honestly, it’s a journey I really wouldn’t trade for anything.


Justin Donald: That’s cool. Do you consider yourself in your role, a culture creator? Or do you look at your role as like, hey, I just need to make sure operations are functioning and people are reporting where they need to and that the breakdown doesn’t exist?


Craig Kessler: Yeah, culture, what’s the expression? Culture eats strategy and execution for breakfast. It’s really interesting. One of the things we did in the early days when I started was we studied remarkable concepts that are known for their culture and hospitality, Ritz Carlton, Four Seasons, Southwest Airlines, Disney. And what we discovered is that effectively, the guest experience will never exceed the associate experience. And so, we double down hard on culture.


And what we ended up instituting is, and it was developed by the whole senior team with representation from frontline associates as well, something called a rally cry. And the rally cry is the one thing you think about every single day. When you get out of bed, you put your uniform on and you take the playing field, which for us is a Topgolf venue. Our rally cry at Topgolf is that we create moments that matter for everyone. And the idea is your job is not to serve burgers and beer and a game of golf, it’s to make a difference in people’s lives, but where the rubber really met the road was when we didn’t just talk about the rally cry, we actually empowered all today 20,000 of our associates to do it. And I can sit here for hours with you and tell you story upon story of where hourly associates or salaried managers have gone above and beyond to make a difference in people’s lives. And it doesn’t just impact the guests, it actually makes our team proud to come to work every single day.


Justin Donald: That’s awesome. Maybe the most important question I’ve asked yet, are you good at Topgolf? And if so, how good are you? What’s your game of choice?


Craig Kessler: I guess it depends on who I’m playing against. I’m middle of the road. I tend to play two games at Topgolf. The first is our most commonly played game, it’s called Topgolf, creatively titled. The second is something new we have, it’s Angry Birds. So, most people don’t know this, but you can come to Topgolf and play a game like Angry Birds, and whether you’re a scratch golfer or my three-year-old son, it’s a blast for everybody.


Justin Donald: Yeah, that’s an incredible concept because you do not have to be good at Angry Birds golf. Like all you have to do is put the ball in play and watch what happens, because you basically have this simulation. You kind of look at a screen, you see this whole setup, and then you hit the ball towards using markers where different things are. And then you have these different wooden boxes that may fall and topple and break other parts. It’s just really fun. So, it was the first time I’d ever played that when we were in Vegas, and it was a huge hit with our group. So, nicely done on that.


Craig Kessler: Well, thank you. I’ll tell you a 20-second story. The first time I ever visited Topgolf, it was a snowy day in January. We were in Alexandria, Virginia, home to the first Topgolf ever built in the US. And I remember walking in, or I should say walking up to the building, I see a line around the block in the snow. We get inside for a bachelor party, and the bay next to us is a group of all women celebrating a bachelorette party. Now, up until this point, I tried to get my wife to play golf a hundred times, couldn’t do it, but when I saw the bachelorette party, I thought, man, something magical is happening here. And what we’ve learned is that the brand has permission to do all sorts of things, including introducing a game like Angry Birds for golfers and ages of all types.


Justin Donald: That’s so cool. Well, I’m guessing, in the role that you’ve been in, with the people that you’ve had exposure to, you’ve probably met some cool people along the way. And I’m curious if you’ve had any specific mentors or peers that have had a profound impact on you or the way that you think or maybe decisions that you’re making now from the lens of the long term. How is this going to impact and play out over several years?


Craig Kessler: It’s a great question, and honestly, it’s hard to narrow the list down to just a couple of people, because I think in this job, the life adventure, and the people I’ve gotten to meet along the way, it wouldn’t have happened were it not for Topgolf. And there have been leaders from members of our board to executives at Topgolf who’ve made a massive difference in my life. If we look outside of Topgolf, there are a couple of people who have had a big difference.


One guy in particular who I really look up to, Seth Waugh, who’s the CEO of the PGA of America. Seth has this unbelievable way about him. It’s a calming leadership style. He’s always thinking about the future. Seth is the kind of guy you walk around within an airport and people want to take pictures with him, but when you’re next to him, you feel like you’re the only person in the world that exists and have enormous respect for what I’ve learned from Seth.


There are a couple of other guys who you won’t recognize their names, but the way they’ve approached fatherhood, the way they’ve interacted with their own dads, I’ve learned a lot from the way they think about being a husband, a father, and a son. And were it not for those guys, honestly, I don’t think you and I would even be having the conversation today.


Justin Donald: Yeah. And this is a great segue because I’m so excited about this new chapter of your life, the impact that this is going to have because you have a new book coming out and it’s just so applicable to so many, anyone who’s a parent, anyone who’s a dad. And I’d say it’s not just limited to dads, but the book is called The Dad Advice Project, right? And I’d love to know, first off, a little bit about that, and secondly, kind of how it became what it is today. Like, how did it go from just this idea of getting advice to actually becoming a book?


Craig Kessler: Happy to tell you the story. So, it starts with a little bit of a sad insight, but I promise there’s a happy ending at the end of this. I don’t have, and in the spirit of being vulnerable and open, a very close relationship with my dad. My wife and I have three boys, one, three, and five, and so, we’re in the thick of it. And I realized about two and a half years ago, not having my dad as a sounding board was a really big void. And so, I emailed a handful of buddies and I asked them to write me a letter on how to be a good dad. That was it.


And what I got back was incredible, it ranged from David Letterman style Top 10 List that were funny but thoughtful to letters they wrote their kids and everything in between. And over the last two and a half years, this thing snowballed. And I ended up with 42 letters, all from guys who were close personal friends. And it’s great you asked me the question about who’s had an impact on my life. Without a doubt, these 42 guys have. And what ended up happening was I put all 42 letters together. A couple of guys asked me if they could read what the other guys had written, but it wasn’t ever meant to be a book. It was really just a selfish question for me to crowdsource advice on how to be a better dad.


Well, with some encouragement from a few of the guys, we approached a few different publishing houses. And interestingly, they all told me the same thing. They said, “Craig, the difference between women and men is that women want advice from other women and dudes just want to hear the sound of their own voice. Nobody’s going to read your book, but fortunately, we stumbled on one group that felt differently. And when they saw the list of authors who contributed, which I’m happy to share with you in a minute, if you’re interested, and they read the content, they said, “Holy cow, we’ve got to turn this into a book.”


Justin Donald: That’s exciting. And yes, of course, I want to hear the list of authors, and I just love that you basically have this, you chronicled all these great ideas and moments in time that people had had, you crowdsourced this with some of your brightest, most successful dads. And I loved the book, it’s theirs, it’s like all of yours. It’s a team effort. It’s not just one person writing, like, here’s how great of a dad I am. It’s hey, look at the wisdom, the collective wisdom that we’ve gathered from all these smart people.


Craig Kessler: You nailed it. I actually found a couple of observations. One, the content for dads is thin; two, the content that is available tends to be one person’s point of view. I think, three, if you’re sick, you go to a doctor because a doctor has seen a case like yours 10,000 times before and has pattern recognition. None of that exists in fatherhood. So, the idea of crowdsourcing this so that you could get 40 different guys and see the world through their eyes and maybe pick up on some patterns preemptively has been helpful to me. And I think the thing that’s interesting is guys tend to be private, but when you ask most guys about fatherhood, it’s amazing. Their shoulders drop, they exhale. And it’s the one topic that’s common ground for almost all dads.


And what you’ll see when you open the book is that all these guys are friends of mine. And they range from people you’ve never heard of who are in unbelievable business and civic leadership roles across the world to a bunch of guys you’re familiar with. So, the foreword is written by George Tenet, the former CIA director. And we’ve got athletes like Davis Love III and Adam Wainwright, the pitcher for the Cardinals, and TV personalities like Mark Rolfing and Notah Begay. I’ll tell you, it was so powerful to see these guys get vulnerable and give you a behind-the-scenes look to what it was like for them raising their kids.


Justin Donald: That’s incredible. And you hit the nail on the head with the fact that there’s not necessarily a ton of books out there for dads. And I look for this. Like this is a topic that I read on in my bookshelf right behind me. I have several of these books and I’m always looking for really good books. And so, I’m thrilled that you have just such a great resource, but also from men that are choosing to be really vulnerable.


And I think the issue that a lot of dads have and maybe you can relate to this, I know that this is true in my life. When we think about being a dad and we think about the decisions that we have to make, sometimes it’s easier to just work or try to build the business or try to do things in work mode because we’re good at it, it’s familiar. We’ve been doing it for a decade or two or three or more versus the dad thing. This is newer. We don’t know it as well. The default isn’t this life of experience.


And so, I find that, like for me, I have to show up very intentionally because if I’m unintentional or if I’m just letting my subconscious lead me, I’m always just going to kind of veer towards the things that I know well, the things that I’m good at, business versus showing up intentionally for my family.


Craig Kessler: It’s probably the theme talked about more than almost any other in the book. And finding that balance is hard. Here’s what’s interesting. If you go all the way back to purpose, like what’s our purpose for being here on this earth? What’s your purpose as an individual? We’re all going to have our own answers to that question, but what I can almost guarantee is that every single person will have an element of wanting to find joy and happiness in life. And what I find fascinating is that for many people, if you drop the ball on family and parenthood and all those sorts of things and you focus on the short-term winds around work, you sort of miss the point, if the purpose is sort of your North Star guiding light.


And by the way, let’s be real. There are times where all of us need to drop those things because work will come first. The question is really about the patterns and behaviors we develop over time. And it’s a trap. If we get sucked into the whirlwind too much, it’s very hard to undo a reputation you’ve built with your kids or your spouse.


Justin Donald: Yeah. And it becomes a routine, it becomes a habit. So, you’ve got to be really careful how you’re spending that time and what decisions you make. When do you choose work over family? When is family over work? I’m part of a dads’ group that I believe you’re familiar with, Front Row Dads.


Craig Kessler: Yeah.


Justin Donald: That one of my closest friends in the world, Jon Vroman, started and I’m the hugest fan. And one of the things that we talk about, and he’s going to be on our episode for Father’s Day, but one of the things that we talk about in that group is that we’re family men first, businessmen second. And I love how just that mantra helps people show up better, differently, more intentionally for their family.


Craig Kessler: You know, Jeff Woods, back to where we started the conversation, said something interesting to me on his podcast recently that we did together. He said, “If you think about business relationships, you think about brands, those tend to be rubber balls. And if you drop them, they’re going to bounce back. They may not bounce as high as you want, but they’re going to bounce back.” Your relationship with yourself, with your health, with your wife, with your husband, with your children, whatever it might be, relationships with people, those are often more like glass balls. And if you really drop it, they can crack. And it’s so counterintuitive that those are the balls we often let go of first. And I think it’s an interesting lesson to keep top of mind.


Justin Donald: Yeah, for sure. And something that’s been really helpful for me in just making these types of decisions, when do you choose, what, and how do you show up? For me, Craig, it was taking whatever situation it is and looking at it 10 years from now, what is the thing that I’m going to remember? Am I going to remember this business deal? Am I going to remember this, I had to show up and do this work, whatever the work is? Like 10 years from now, am I even going to remember that, but what about that memory with the family? And is that going to be a lasting memory? And that really has been a guiding principle for me in a lot of the decisions I’ve made, both work or travel.


Let’s say I’m super busy right now, but am I going to remember the busyness of this small little moment in life? Or am I going to remember that I didn’t go on this amazing trip or meet these amazing people or spend quality time with my family in maybe an exotic location? And so, that has been a really good North star for me as well.


Craig Kessler: I love it. And to build on that point, I think one thing that I’ve learned, and it’s actually a theme that comes out in The Dad Advice Project, there is a hybrid. So, historically, personal life and professional life were kept very separate and people were very intentional about that. What we’ve done with our family, and again, quite a few of the authors talk about it, is trying to find ways for work-life integration.


So, I’ll give you a great example. Rex Kurzius is one of the authors, a super inspirational guy. He talks about how we give our kids exposure to sports and arts and crafts and music so that when they’re in situations that require memory recall for those types of activities, they just jump in and they do it, but when it comes time to dad having or mom having a work conversation, we close the door so that our kids don’t interrupt or hear what’s going on. That makes no sense. Rex says, “Open the door, invite your kids to listen in on speakerphone when you’re interviewing someone or to help you name a new product or business line.” And now, dinnertime conversations become richer and you’ve given your kids exposure to more sophisticated business-type topics at an earlier age.


And for us, look, I realize we’re very lucky because Topgolf is a unique business, but we take our kids to Topgolf all the time to try out new games and try the food and experience what other five-year-olds and three-year-olds are experiencing. And our kids are proud to be a part of that. And I think there are times when it doesn’t have to be this or that, it can be a yes, and.


Justin Donald: Yeah, I couldn’t agree more, Craig. And I’ll even just say this, like I’m super guilty of this, when I first started podcasting, I remember having my door closed, let my family know, hey, by the way, I’m going to be recording. If you wouldn’t mind being quiet, that would be wonderful, although we all know how that goes, right? And I just remember, like, trying to be in this place where I wanted to control volume and I could hear kids running around in the house and footsteps, and my daughter’s friends are over and they’re– I mean, literally just total pandemonium going on. Or sometimes she’d want to jump in and see what I’m doing and just take a look.


And for a season, a small short season, I was like, oh, man, I’m trying to control who comes in, who doesn’t, when you can talk, when you can’t. And that’s exhausting. And I’m actually disappointed that I even took that direction, because the moment I loosened up and just said, “Hey, I’m going to be recording now, feel free to carry on, and my editor can edit stuff out and there might be stuff he can edit.” And oh, well, people just kind of hear the real deal of what’s going on. So, my daughter will pop in periodically and it’s just so much better, it’s more fun. There aren’t as many walls in lines and what people can and can’t do, and it has also just kind of been a lot smoother on the family front so that my wife doesn’t feel like she has to keep anyone quiet.


So, you’re spot on when you say that there’s this way that these worlds can collide and we want to give our kids that exposure. I mean, I want my daughter to know about this. I know you want your kids to know about this. So, great point.


Craig Kessler: Awesome.


Justin Donald: So, what are some other topics in the book that you think are really relevant, that you would love people to know before even having a chance to get the book?


Craig Kessler: I would summarize what I learned into two camps. The first is that there are themes that come up more often than any others and by a mile. And the themes are things like kids need to feel a sense of physical and psychological safety. They need to understand it’s okay to take risks and fail. My favorite or I should say my wife’s favorite is love your wife and make sure your kids see it, because that’s how they’re going to learn how to treat women and have relationships down the line.


Justin Donald: That’s powerful.


Craig Kessler: Well, yeah, what I find interesting about it is for some, when we talk about this, they go, well, okay, obvious. For others, they say, “Well, actually it may be obvious, but the fact that those themes came up more than any others means we need to intentionally keep them top of mind. So, that’s the first set of lessons. The second is what I would call one of the really cool, interesting tactical tips. Some of which we’ve actually implemented with our three boys. And it’s created just a really fun set of journeys in our family. And I think as the reader goes through and sees some of these tips and tricks, it’ll be fun to experiment with some of these things and turn them into traditions for your own family.


Justin Donald: That’s great, yeah. As I think about some of the things that are in this book and some of the things that we’ve discussed, some of them are obvious, like, yeah, you should do that, yeah, you should love your spouse, but does that mean that we’re doing it? I mean, sometimes I think that things work so well that you start to forget that you are doing them or how well they work. So, I don’t know if you’re like me or if other guys are like me, but sometimes, I’m like, when did I stop doing that? I used to be so good at that. All of a sudden, I’m not anymore, but that works so well. And now that I’m not doing it, things aren’t as good.


Craig Kessler: So, my wife read the book, and I asked her for her takeaway. And she had a few. Her first was, this is a book about relationships. It’s meant for men and women, even though it’s called The Dad Advice Project. Fair enough. The second takeaway, though, for me was the really powerful one. And I think it hits on what you’re describing. She said, “You know, Craig, when I read mom blogs or books or articles on how to be a mom, nine times out of ten after I finished reading, I feel like I’m less than, or that I’m not living up to the mom that I should be,” but what’s interesting about this and again, it hits on what you’re saying is I’d say half of the submissions, the guys talk about things they’re screwing up and where they’re going wrong.


And at the end of it, you leave recognizing we’re not perfect and they’re not perfect. And it makes you want to be a better person because you realize what’s possible. And back to this idea of psychological safety, that’s not true just for kids, that’s true for adults, too. And if you can find a way to let your guard down, taking advice from a bunch of other people and still feel psychologically safe and proud of who you are at the end, to me, that’s a pretty magical recipe.


Justin Donald: Yeah. And your wife is spot on, on this, too, because when she says this is a book about relationships, this might be a relationship book about how you parent your kids or the relationship you have with your spouse, but that’s also the same thing as the things you should do in relationships with coworkers, in relationship with people that work under you, with you, vendors, contractors, you name it, and so many of these things.


I see very successful businessmen, businesswomen as well all the time, and this is more on the businessmen side, where they have these incredible relationships at work, but for some reason, they get home and it’s like leftovers and they’re irritable and they don’t have the same just relationship IQ, emotional IQ at home as they do in the office. It is really kind of a mind-boggling thing to me, but this is real like I see this often.


Craig Kessler: Someone asked me once, what’s the best piece of advice you’ve ever heard or gotten? And I go back to a story from a– I think it was a documentary I saw. It’s with Coach K from Duke basketball. And someone said, “Coach, how do you do it? How do you take a random collection of players when year in and year out?” And he said, “I’ll tell you the answer, but it’s not going to make sense.” The reporter said, “Well, try me.” He said, “Well, I tell my guys to talk when they’re tired.” And the reporter said, “You’re right. I have no idea what you’re talking about.” And he said, “Well, look, most coaches teach their teams that when they’re towards the end of a game, and the game is closed, and the team is tired, to conserve energy. And the best way to conserve energy is to stop talking.” He said, “I feel the total opposite.” He said, “When you’re anxious and you’re down by two and you’ve got to come back with 90 seconds left, the only way to fight through and win is to talk when you’re tired.”


And I find the exact same advice holds true in relationships both in the workplace and at home. And I think because the incentives may be a shorter term at work and they’re right in front of us and we have reviews two or three times a year, it’s easier to force yourself to talk when you’re tired and work through challenges, but if you don’t apply those same principles and approaches at home with your kids and your wife, man, what you described is one of the possible outcomes.


Justin Donald: And I also find that from a personal experience, but also in coaching a lot of people, is that when life on the home front is not strong, it does carry over to your professional life. And the stronger a family unit that you can have and create and foster the strengthening of those relationships, the better it is in all the other compartments of life. And I’m sure that that’s something that you’ve experienced. I’m sure that there are some dads that gave advice in your book on that, too.


Craig Kessler: You hit the nail on the head. Totally agree.


Justin Donald: So, if there was one takeaway from this book that you’ve had, so you had the luxury of getting a chance to read all this, put this together, put it in order, whatever makes the most sense, is there something where you feel like, hey, this thing allowed me, this idea, this concept, this thought process, this thing I took action on immediately and has had a profound impact on my family or on me or on loved ones?


Craig Kessler: The answer may sound odd, but for me, I learned through this project that we’re all trying really hard and we’re all screwing it up. And when I realized that some of the dads I respected the most are going through things that maybe I never would have imagined and the guys who seem like they didn’t really have it together really have a lot of depth and richness to the way they parent, it was a very liberating thing. It made me realize there is no perfect. Just keep swimming, just keep trying, and you’ll get there. I think that’s my biggest takeaway.


Justin Donald: Yeah, that’s cool. So, is this something where you feel like, hey, I have written this book or I’ve assembled this book? Or do you see this as something where there’s going to be volume two, or there’s going to be like, hey, at this age, we’ve got another version? I’m curious.


Craig Kessler: I’m not that far in my thought process, to be honest. Here’s what I’ll tell you. It is so important to me and to the 42 authors in the book that this has an impact on dads and kids. In fact, about 30 of the 42 authors came to Dallas to my home for dinner last week to meet each other for the first time. And it was one of the most special nights we’ve ever had, I’ve ever had. And this was a topic of conversation. What next? What I know is that we have two goals, for now, to make this book land and have an impact, and the second is I grew up going to the Boys and Girls Club in San Diego, it’s where I spent spring breaks and summers. And so, I’m a proud supporter of the Boys and Girls Club, and if this thing lands, the Boys and Girls Club will be a big beneficiary of it. Beyond that, time will tell.


Justin Donald: That’s amazing. Well, I love when you can put something out in the world, the content. So, for me, it was the same thing. I wanted the content to have value, but I wanted the proceeds to also be able to add value in terms of where it can be put to the best use. And I love that you’re doing that. I’m curious for you, from the standpoint of, like, legacy, have you thought a lot about this? Or where does your mind go when you think about legacy for your family, a legacy for what you’re doing, and the footprint that you’re going to have and leave on this world?


Craig Kessler: I’m 35. I don’t spend really any time thinking about legacy. What I do think a lot about is how to have an impact now. Whether people remember that and tie it to me or my family, I have no idea, but the impact that I think about now is the world is still upside down, whether it’s COVID, whether it’s the senseless killings of innocent, unfortunately, most commonly, African American men, whether it’s the persecution of minority groups across the country, the world at times is filled with hate. And I genuinely believe whether it’s through project like The Dad Advice Project, whether it’s through at Topgolf, or rally cry of creating moments that matter if all of us can do just our small part to try and make the world a better place in a more joyful place, mission accomplished.


Justin Donald: That’s awesome. And I love your rally cry for Topgolf. In fact, that’s something to me that has been important in all categories, so most certainly at work, but I actually think as just parents and as spouses and most certainly in the business world as professionals, making moments that matter and creating experiences for a lifetime, I think that’s everything. And the more you can do that for working professionals, that often is easier done on the professional business side of things. And I don’t know if that is second nature to people, but to me, in a leadership role in many different businesses, that was monumental in terms of culture, retention, and all that.


I actually find that having moments that matter and creating experiences for a lifetime with your family is the most important thing you can do. And I love really being intentional there. And I’m curious if that is something for you that has also kind of, and I know your kids are young, but is that something that’s already started to take root in the family?


Craig Kessler: Totally. In fact, listening to you talk, it jogged the memory. My wife’s company used to host a retreat once a year and they’d fly, and the spouses. And so, I flew in for one of these company retreats, and the company had organized a guest speaker. And the topic of the speech was interesting. Effectively if you have to spend money in life in order to get by, and we all do to buy groceries, keep the lights on, etc., what are the principles around spending money that will help you maximize happiness?


And I took three things away from that speech. The first was give as opposed to just buying for yourself. The second was delayed consumption actually maximizes happiness. And the example was, if I buy a cookie and eat it now, I get some level of satisfaction. If I buy a cookie and wait until tomorrow to eat it, I actually get some satisfaction in the build-up to eating the cookie that I wouldn’t have gotten if I ate it right away, and I’m still super stoked once I eat the cookie. So, delayed consumption was the second. And then the third without a doubt is experiences over things. And I think those are three principles we refer back to from time to time.


Justin Donald: That’s amazing. And I appreciate you sharing that. Wow, this has been awesome. Hey, Craig, I would like to know, and I’m sure our listeners and those watching would just really enjoy knowing how they can get their hands on your book and how they can learn more and how they can take action.


Craig Kessler: Absolutely. The simplest way, go on to Amazon, The Dad Advice Project is the name of the book. Two other things I’d say, check out the website You’ll see the background on the project and a blurb on each of the authors. And the final thing I’d say is the book comes out June 1st, just in time for Father’s Day. If you buy a copy of the book and send us your receipt or send us a screenshot of your leaving a review on Amazon to gift at, we’re going to send you some behind-the-scenes footage of the authors from The Dad Advice Project being interviewed. And it’ll just be one more tool at your disposal to help on the parenting journey.


Justin Donald: That is really cool. I appreciate you sharing that with our audience here. And I just am so excited for what you’re building and the impact that it’s going to have. Do you have any last thoughts or comments that you want to share before we wrap things up?


Craig Kessler: All good. I just really appreciate you having me on, and if anybody in your listener base wants to reach out, they can do it through the website and happy to support however I can. Really appreciate it.


Justin Donald: Well, thank you so much, Craig. I’ve really enjoyed hanging out and learning more about what you’ve been up to here recently. And I’m such a huge fan of you in general, of your organization that you help run, and of the impact that you are having and will continue to have on families. And I want to thank you, from all of us, for assembling this amazing list of co-authors and putting these letters together, because this is just fantastic and the world needs it. The world needs more of this type of content. So, thank you.


And I have one last message as I close things out here today. And it’s the same thing I share to wrap up every message, and that is to take some form of action today towards financial freedom and towards living the life of your dreams, a life that is intentional that is created, not a life by default, but a life by design that is on your terms. We’ll talk to you next week.


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