EP 137

Why My Family Asks Me to Travel More for Work (LIVE from Triad's DBDL Retreat)

With

Daniel Crosby & Jason Khalipa

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Inside This Episode

Most advisors I know have felt that tug-of-war: do I grow my firm, or do I show up at home? The truth is, you don’t have to choose.

At our Founder’s Retreat in Maui, I sat down with two guys who really live this out: Daniel Crosby, a behavioral finance expert, and Jason Khalipa, a CrossFit Games champ turned entrepreneur. They’ve both spoken at Triad experiences before — not as “fly-in, fly-out” speakers, but as part of the community. They show up with their families, they engage, and they embody what it means to “Do Business. Do Life.”

Together, we dug into how including family in business events removes the guilt of being away. It lets you go deeper on the business side, knowing you’ll walk out of the room and step straight into making memories with your family.

If you’ve ever carried the guilt of missing a soccer game or dinner with your family in the name of work, this conversation will hit home.

3 of the biggest insights from Daniel Crosby & Jason Khalipa…

#1. You Don’t Have to Choose Between Business and Life

Business success and family life don’t have to compete. You can thrive in both without compromise.

#2. Eliminate Guilt by Including Family in the Journey
Jason and Daniel shared how events that welcome spouses and kids create freedom instead of guilt. You’re no longer worried about missing dinners or soccer games — family is part of the journey. That integration lets you be fully present in business sessions and fully engaged at home.

#3. Core Values Only Matter if You Live Them
It’s easy to carve values into a wall or throw them on a website. Living them is harder. At Triad, values show up in how members treat each other, how families are included, and how community comes before transactions. That’s what builds trust and belonging — for advisors and their families.

KEY TAKEAWAYS: 

  • Live From Maui Founder’s Retreat
  • What “Do Business. Do Life.” Really Means
  • The False Choice Between Business and Life
  • How Triad Makes Families Feel Special
  • The Guilt Of Missing Family Moments For Work
  • Balancing Travel Demands and Family Priorities
  • Designing Events That Include Spouses and Kids
  • Why Our Kids Love This Business Community
  • Core Values That Actually Mean Something
  • How Triad Proves It’s More Than Branding

SELECTED LINKS FROM THE EPISODE: 

PEOPLE MENTIONED IN THE EPISODE:

THIS WEEK’S FEATURED REVIEW

Want to leave your own review? Visit us on Apple Podcasts via mobile, scroll to the bottom, and give me your honest thoughts. I read EVERY review that comes through. Not only do they light me up, but they also make a huge impact on people who are considering listening. To leave your review, CLICK HERE. I might even feature it on the show 🙂

MIC DROP MOMENTS

  • “I think forever doing business or doing life has been presented as this false choice, and we could only have one at the expense of the other. This event is proof you can have both. I find myself more locked in because my mind’s not on who’s at home and what soccer game or dinner I’m missing. It let’s me really focus and go deep on the business side when it’s business time, knowing I’ll see my kids and my wife tonight and we can have that great time. It’s absolutely incredible.” – Daniel Crosby

  • “There’s nothing else we go to that my family feels so excited about. And I think that’s just a testament to the way you guys (Triad) structure things because you make them feel seen and special versus just joining.” – Jason Khalipa

  • “This isn’t just like some slogan you came up with. It’s what you embody, it’s to your core, and it’s to Triad’s core. I think that’s really important because people can see through it if it’s just a slogan.” – Jason Khalipa

  • “It’s wonderful to come to a place where that tension doesn’t exist, where kids are centered, where kids are taken care of. And again, the adults can be fully present. You don’t have half a mind back home. You can be fully present. The AMRAP mentality, you can be all in on the thing you’re doing in that moment, whether it’s time with family or really learning incredible stuff about how to be a better business person.” – Daniel Crosby

  • “When it’s just a slogan, it’s actually cancerous. It’s actually worse. Enron famously had their values etched in stone, but when you do that and you’re not living up to those values, all you’re doing is creating a physical reminder of the distance between you and your aspirations.” – Daniel Crosby

Brad Johnson: All right. Well, gentlemen, here we are, Maui. DBDL Founder’s Retreat and just wanted to grab some time. I think one of the things that I really appreciate about both of you, that’s really important to our community, is just kind of practicing what we preach and not just getting “Hey, here’s a random person that can give a great keynote,” and then they disappear into the green room, never to be seen again. Both of you have fully embraced – this is multiple times you’ve been to a Triad Experience. You’re here with your families. So, I’d just love to get your unfiltered take on, how does this feel? What’s DBDL like? What’s your version of that? And maybe we start with Jason. How’s it been so far?

Jason Khalipa: Yeah. I mean, obviously, I love what Triad’s doing. So, DBDL to me, and I shared this earlier, but like DBDL is like that’s the mission, like that’s the vision. That’s what we should all be striving for is to be able to do business and do life, because I know for me, I’m sure for both of you guys too, like I want to be successful in business. Like, I want to be able to provide for my family. I want to be achieving goals that I set out for myself in business because I get value from that. Like, I get purpose out of that because I also believe that our work drives value for other people. So, for example, I’m in the fitness space. The better our business does, the more people we’re impacting, that’s great for everybody, right?

But at the same time, that’s not at the expense of the family. Like, the family still has to be a huge priority. And so, I think this balance of DBDL is so beautiful because it allows me to achieve my goals and have a mindset of like making an impact on the business side while simultaneously also being about doing life and not forgetting that the most important thing is right in front of me, and that the seasons of life and our kids grow really fast. So, I think you guys do a really good job of constantly reminding your founders throughout the year of the importance of doing business and doing life. And I think events like this just kind of are a great example of an anchor that someone can use to make sure they stay on track and not get distracted either way.

Brad Johnson: I appreciate that. Daniel, thoughts?

Daniel Crosby: Yeah. I think forever doing business or doing life has been presented as this false dichotomy, this false choice, and we had to have one at the expense of the other. And I think this event shows really viscerally that you can have both simultaneously. And in fact, I find myself more locked in because my mind’s not on who’s at home and what soccer game I’m missing and what dinner I’m missing. It’s let me really focus, let me really go deep here on the business side when it’s business time, knowing that I’ll see my kids and my wife tonight and knowing that we can have that great time. It’s just absolutely incredible, and I think it’s a very modern approach to see that both can help each other instead of sort of forcing people into this false choice.

Brad Johnson: We had one of our members that you just reminded me of something that was shared. It was probably a year or two back, and he said, “You know, for us adults,” he said, “having the kids here keeps us on better behavior.”

Jason Khalipa: Oh, yeah.

Brad Johnson: And I thought that was an interesting take. So, both of you have been to a lot of experiences all around the world, all types of different groups you’ve spoken to. What do you think infusing family into this does for us?

Jason Khalipa: Well, I’ll just speak real quick on this, like my kids were super excited that I got asked to come back here because it’s something that you guys do a really good job of making them feel special too. Like, at no other point, especially for what I do for a living, like we’re not in the corporate world. We own and operate gyms, and we’re in the fitness space, so they’re not surrounded by gifts and stuff like that, that way. So, when they come here, and they’re able to go spend some money in your gift center, wow. They’re able to be treated to certain dinners and stuff. It’s like, “Wow, this is really cool,” because you guys make it a really special experience for them.

So, I think what you guys do is super unique for the kids because I can’t think of another company or whatever that does that. Like, you make them feel even more special than perhaps the adults do, which makes my job a lot easier to come out here because they’re really looking forward to it.

Brad Johnson: Yeah. I love that.

Jason Khalipa: I can’t even remember what your original question was. That was just fresh in my mind, like how excited my kids are to come here.

Brad Johnson: Well, I think if we let ourselves, I mean, obviously, we’re the parents, so we’re constantly thinking like here’s what we need to do on this trip. And the dad talks before you get out of here, but we can sure get energy from our children too. So, if they’re excited about it and you’re like revisiting the joy of childhood through them, that’s a beautiful thing, man.

Jason Khalipa: For sure.

Brad Johnson: So, I love that.

Daniel Crosby: So, it is interesting. I was asking my kids on the way here what they were most excited about, and there are endless things to be excited about. There’s snorkeling and gifts and great food, but the thing that they were the most excited about was making new friends and making new relationships. And I fully expect some group chats to be coming out of this week in Maui. My kids are having an incredible time. And my son turned to me yesterday during that same little shopping spree, and he goes, “This can’t be real.” And it’s just if someone does something kind for your kid, there’s a special place in your heart for someone who is kind to your children and who sees your children, who cares about your children. That I think is the DBDL difference, and it’s really a joy to watch.

Brad Johnson: We’ve, obviously, spent a lot of time in finance, Jason. Some you’ve spoken to, I’m sure, other groups in finance besides us. But one of the things when you have to be away from family and you miss a ball game, unfortunately, you miss a dinner, you miss one of those special moments, like you carry that guilt. And I’ve, as a dad, had that tug of war before where you know you’re providing, you’re making a living, but you’re missing the stuff you can’t buy back. And as Triad came together, we’re like, “Let’s not do that.” Now, granted, there are still things that pop up, but what if we created an intentional environment to where you could have the yes-and instead of the either-or?

And so, for you guys, have you dealt with that? I mean, you’re both very successful in business. I know you’re also both very intentional husbands and fathers. Can you think back to a trip where you’re like that kind of guilt inside of you like as a dad or as a husband?

Jason Khalipa: Yeah, it used to happen to me all the time. It’s gotten better because I’ve learned to say no a little bit more. But, I mean, like I was saying earlier today, I used to travel to Asia once a month. And like, dude, you’re going to miss stuff. Like, I went to Asia for a lunch one time and turned around, and I still missed two days with the family.

Brad Johnson: You flew out for a lunch.

Jason Khalipa: I flew out for a lunch.

Brad Johnson: That’s a wild lunch right there.

Jason Khalipa: And we got the deal. So, it was worth it. But, I mean, we were already rocking and rolling. We had to take care of something. I had to go take care of it. But that’s an example. Like, there was a lot of guilt. And then there’s guilt on both sides, too, because like then I started feeling like I’m not fully enjoying these experiences when I traveled to Asia, because it’s purely like just get home. But then at the same time, it’s like, “Well, should I have combined it? Should I have brought them?” That’s where I think nowadays I’m learning to say no more often, and then also incorporate them. So, like, events like this are perfect because you can incorporate them into the things that you’re doing.

Brad Johnson: Yeah. That’s the goal.

Jason Khalipa: Yeah.

Brad Johnson: Yeah. Bring the whole crew.

Jason Khalipa: I mean, I’m glad the Asia trips are gone. That was…

Brad Johnson: Well, I’ll tell you, one of the early moments in Triad where I knew we were doing something right, you came to Lake Tahoe two summers ago.

Jason Khalipa: Oh man, this place. Have you been to the Ritz in Lake Tahoe?

Daniel Crosby: I have not.

Jason Khalipa: Dude, it is so nice. It is so nice.

Brad Johnson: Well, so you had to fly out for the CrossFit games on ESPN.

Jason Khalipa: Yeah.

Brad Johnson: So, I think you were only there for the very first day. And I remember you telling me, “My family’s kind of upset at me that we have to leave.” And I was like, “Okay, cool. We’re doing something right if the family’s telling you they don’t want to go.”

Jason Khalipa: Yeah.

Brad Johnson: So, I mean, that’s the goal is to stay on that track.

Jason Khalipa: For sure.

Daniel Crosby: That tension you’re talking about is the defining struggle of my professional life. I mean, I don’t know how else to say it. Like, that is the defining struggle of my professional life is this tension between the travel demands of my career and this desire I have to put first things first, to have my family be the biggest rock in my life. And I like that you take that tension off the table, and you just say, “You can have both.” And I mean, I have, for lack of a better word, smuggled my children into other conferences. I mean, I’ll just show up with a kid and just put my kid in the front row and say, “Hey, watch Dad rock for an hour, and I’ll come back and then we’ll go do something.”

But I’ve gotten mixed responses to smuggling a kid into an event. It’s not always great, and you feel like you have to apologize or that they’re in the way. It’s wonderful to come to a place where that tension doesn’t exist, where kids are centered, where kids are taken care of. And again, the adults can be fully present. You don’t have half a mind back home. You can be fully present. The AMRAP mentality, you can be all in on the thing you’re doing in that moment, whether it’s time with family or really learning incredible stuff about how to be a better business person.

Brad Johnson: Yeah. One of the things we thought about how to design experiences, in finance, it’s typically all about us, right? Typically, the dudes from a percentage standpoint. Now, the ladies are coming up as they should, but it’s mostly been a very male-dominated industry. And if you look at all of the experiences I’ve been to over, I guess close to 20 years now, there was no intention around the significant other. There was no intention around the kids. And when you start to look through their lens versus our own, it’s wild the different things you can create, kids camp, fun experiences for them, different gifts that are specific to kids versus adults. And like the intention was there, but each one of these that we do, I’m continuing like, “Oh, okay, we got to level this up or we got to level that up.”

And so, it actually makes it a lot more fun when you’re designing a community with different viewpoints. It’s not just all about us. It’s like love on the spouses, and that’s going to light you up probably more than the guy that’s been gifted everything probably in your career. So, how does that hit when your spouse or kids are coming up to you and like, “Dad, check this out,” or your wife’s like, “Hey, check out this cool intentional thing they did for me”?

Jason Khalipa: Well, I mean, they just haven’t, like, it doesn’t happen very often. Like, you’re right, it’s always through the lens of like the person they’re initially trying to please. I think with DBDL, it’s like you’re trying to make the experience great for everybody. And frankly, I mean, probably, I don’t want to say that the founder is last, that’s not the way to look at it, but it’s kind of like you lead with the kids and the spouse and then the founder comes in, right? Versus normally it’s the opposite way, right? And I think that, I think, it does a lot. I mean, I know for me it’s like there’s nothing else we go to that my family feels so excited about. And I think that’s just a testament to the way you guys structure things because you make them feel seen and special versus just like joining. You know what I mean?

Brad Johnson: Yeah. Well, good. We’re going to stay on that path.

Jason Khalipa: Yeah.

Daniel Crosby: So, my first Triad experience was during our spring break. And we had tentative plans to go to the beach. And so, I had to come to my family and say, “Hey, guys, instead of going to the beach, I would like for us to go to a finance conference.” And that went over about as well as you’d expect initially, and no less a finance conference in our hometown of Atlanta, like 20 minutes from my house. Kids were not excited about it going in. Coming out, “Dad, that was the best ever. That was the greatest ever. We made the right call. We made the right choice.” And so, when this opportunity came up, it is now my kid’s first week of school, and we pulled them from the first week of school to attend DBDL Retreat. Sorry, school. But yeah.

To have seen how far they’ve come and how excited they are, and that it’s no big deal to miss spring break or it’s no big deal to miss the first week of school, and reuniting with their friends, because that’s how special this experience is, and the relationships they formed here.

Brad Johnson: I don’t take that for granted. That’s cool to hear. And also, it was one of the coolest things that I got to deal with where we connected with Will Guidara, who was at the same experience that you guys were at. And he’s just sitting there chilling with your kids. We’re snagging Taco Bell, which that reignited a Taco Bell addiction for you, so congratulations.

Daniel Crosby: Yeah, yeah, yeah. Thank you. Yeah. Eating Taco Bell every week since we met Will Guidara. Thanks for nothing, Will.

Brad Johnson: Yeah. You meet a guy that formerly ran a three-star Michelin restaurant, and you come out with a Taco Bell addiction. You didn’t see that one coming.

Daniel Crosby: Yeah. Didn’t see that coming.

Brad Johnson: Well, guys, we are in Maui. We’re here with our families. So, thank you for, number one, being here and playing all out. I love the fact you brought your crews. And I know that’s an investment of a lot and a lot of trust as well. So, appreciate you both being here. And the business sessions are officially over, so it is time to do life. So, let’s go do it. I think a luau is in our future.

Daniel Crosby: I’m in.

Jason Khalipa: Sounds good.

Brad Johnson: Any parting thoughts, or should we call it a day?

Jason Khalipa: Just do business, do life. I love it. I think the slogan is not just, I mean, just to kind of like caveat for anybody who doesn’t know you, like this isn’t just like some slogan you came up with. It’s what you embody, it’s to your core, and it’s to Triad’s core. I think that’s really important because people can see through it if it’s just a slogan. And for you guys, it’s a core value. I think that’s the biggest difference that I see. So, thanks for being you.

Brad Johnson: Thank you. Appreciate that.

Daniel Crosby: You know, when it’s just a slogan, it’s actually cancerous. It’s actually worse. Enron famously had their values etched in stone, so that when you drove up, but when you do that and you’re not living up to those values, all you’re doing is creating a physical reminder of the distance between you and your aspirations. I was a little bit cynical about Triad. I knew you were well-branded. But when I came here to this place, and I saw it firsthand, a couple of things that made me know this was different. I said this morning in my talk. Usually, when people come up to me after I’ve given a presentation, they want my knowledge, and that’s fine. That’s business. That’s transactional. I know stuff about behavioral finance. They want that knowledge. Let’s talk. Awesome.

There was that, of course, when I spoke at Scale Summit, but there were also people wanting to know my story and know my kids and know my wife. And that’s such a qualitatively different thing. And so, it really does feel different here. The other sort of interesting thing, usually, when I leave a speech, usually, when I give a talk, I walk off the stage, and my LinkedIn is blown up. Like, a bunch of people in the crowd have sent me a link.

Jason Khalipa: Want to connect or whatever.

Daniel Crosby: Yeah, want to connect on LinkedIn. When I got off the stage at Triad, my Instagram was blown up. And I thought, I was like, “That’s a fascinating little data point.” These people want to know my life, not just whatever corporate slop I’m putting out there that day and were just not the business side of me.

Brad Johnson: I love that. Well, that’s a testament to our community, and just like you guys trusted us, so did our members. And so, it’s humbling when people trust you at that level because it’s one thing to trust you on the business front. It’s a whole another thing to trust you on the family, on the life front. Alright, gentlemen. Well, thank you for the time.

Daniel Crosby: Thank you.

Brad Johnson: Let’s get on to the Do Life.

Daniel Crosby: Let’s do it.

Jason Khalipa: Let’s do it.

Brad Johnson: Alright.

Disclosure

DBDL podcast episode conversations are intended to provide financial advisors with ideas, strategies, concepts and tools that could be incorporated into their business and their life. No statements made in the episode are offered as, and shall not constitute financial, investment, tax or legal advice. Financial professionals are responsible for ensuring implementation of anything discussed related to business is done so in accordance with any and all regulatory, compliance responsibilities and obligations.

The Triad member statements reflect their own experience which may not be representative of all Triad Member experiences, and their appearances were not paid for.

Triad Wealth Partners, LLC is an SEC Registered Investment Adviser. Please visit Triadwealthpartners.com for more information. Triad Wealth Partners, LLC and Triad Partners, LLC are affiliated companies.

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