News & Insights

Nick LoPresti (00:06.606)

Hey everybody and welcome to the next episode of thinking independently. I’m Nick Lopresti, chief of staff with Good Life Companies, joined today by Conor Delaney, the CEO of Good Life Companies. Welcome back, Conor. Happy to be here, man. In Chicago, the land of Kevin McAllister.

I mean there is a thing about Home Alone and Chicago and we’re going we’re going today. You really have the desire to see that. I’m a huge fan. I gotta see it. My kids are gonna be jealous. It’s a bucket list item for you. it is. It is. We’re knocking it down today. Excellent. Well we have a couple of guests with us today which is not always the way we roll but we wanted to be able to bring in some additional folks for today’s conversation. So we’ve got Nick Alberino.

our head of HR and talent with Good Life. Welcome Nick. Thank you Nick. And we also have retired Air Force Colonel Ben Bishop with us here today. So welcome Ben. Thank you Nick. How was your trip? The trip was fantastic. So to be here in Chicago. Yeah, absolutely. And a retired Air Force Colonel. Yes. You’ve got some things in your

Nick LoPresti (02:00.206)

Background that are fairly interesting and we want to talk a little bit about we’re pulling it all out. Yeah, we really are We’re gonna fight he’s under the gun. Yeah 26 years 26 years and the air force and lots of lots of accolades to your name including right 2700 hours in the cockpit 340 of those in combat missions

You’ve flown the T37, the T38, the F15, the F35, and the F16. So what’s one thing that we wouldn’t know by reading your bio? What’s one thing about Colonel Bishop that we wouldn’t necessarily know by reading your bio? I would say one thing that you wouldn’t know about Colonel Bishop is what have I treasured in that?

26 years the most and I will say Flying those airplanes. It was amazing. Like don’t get me wrong being able to purse, you know pursue a dream of mine since childhood You know, we’ve known each other a long time. You’ve known I’ve always been fascinated with aircraft And be able to do it in a manner that serves something that’s larger than myself, you know, was great but the thing I treasured the most wasn’t necessarily

flying a fighter aircraft, it was being in a fighter squadron. And what I mean by that is I got to be a member of amazing teams that were focused on a mission that were focused on each other and making each other better. And if I could, you know, kind of pass on any experience or any wisdom from that in whatever you decide to pursue in your career is, know, focusing on something that you’re passionate about is important. And even more important than that is

Who are you on this journey with? And being able to strengthen those teams and what I’ve gotten out. I left the service a better version of myself. And as I look at where I am now and how I continue to grow, those are some things that really come to mind. And as Ben alluded to, I’ve known Ben for 35 plus years. We went to high school together and had a chance to attend his

Nick LoPresti (04:26.23)

retirement from the Air Force, which was relatively interesting because we keep track of each other over the years, you know, as you were starting your family and I’m starting mine and things are going along and then you get to the you’re going to retire. All right. Well, I’ll go to that party. That sounds pretty good. And the the general got up to, you know, kind of walk through your career in the military. And I was there with a friend of ours from high school, George.

And he’s reading down all your accolades about the things that you had done in your experience with the Air Force, you know, where you were in positions where you five, six, seven people to positions where you ended up leading almost 2000 people. Right. So what a journey. And along the way, somehow you were the top aviator in the Air Force. Is that true? Did that right?

Well, I did have the opportunity to attend the Air Force Weapons School or weapons instructor course. That’s the Air Force’s version of Top Gun. And as a graduate of that course, you are at the top of your field. You’re one of the best fighter pilots or combat aviators. And I was able to go from that position to a squadron and lead a squadron through a combat deployment. And the squander did amazing. And then

At the conclusion of that deployment, came back and then there is actually award for the weapon school issues every year to the top graduate of the entire year. And that’s the Risener Trophy and that was actually awarded the Risener Trophy. And it was given to me, but it wasn’t really for me. It was because of the performance that Combat Squadron had performed and how well that we have done on our deployment.

And so sitting there listening and the general giving these awards and he mentions that one and sounds pretty good to me. And I looked at George and George looked at me and I said, did you know any of this? He goes, no, I didn’t know anything. And so the humility part of it. And this is something that we talk about with good life. Right. It’s not always about spiking the football. And there’s a lot of things that go on that we don’t necessarily talk about, but

Nick LoPresti (06:47.362)

How important is in the leadership journey, how important is that humility? It is difficult for me to overstate the importance of humility for any leader. And there’s some paradox there because if you think you’re humble, then you probably aren’t. So it’s something you always strive for. But when I think of humility, it’s one of the definitions I heard is humility is not thinking less of yourself.

is thinking of yourself less and not making it about you. I was incredibly grateful that you and George came to my retirement ceremony. It was amazing having a four star general like describing my career. But ultimately that retirement ceremony wasn’t for me. That was for my family, for my wife, Aaron, for my kids. It was important for them to understand how I decided to

choose a life of service and celebrate their sacrifice and accompanying me on that service. And that’s what’s been great about being here with the good life team is talking about how do we build teams? How do we make leaders that are the best versions of themselves and how do they grow their organizations and how do they grow their teams? And that’s one of the great things I love about my service. And I think Nick, we’ve been talking about our, you know, our experiences and how that was unique, serving our country in uniform.

But taking some of those ideas and principles and applying and sharing them to to everyone because yes one of the things about having that military service is there is focus of mission but it’s all about accomplishing that mission as a team, right? And I think that translates well into you know, all careers. Absolutely. Conor, how important is the the humble aspect in your mind around good life? I was I was actually just getting hung up on the retirement party that

I mean, I’ll go to yours. can come to mine. Yeah, it’ll be fun. I mean, I think it actually Nick and I were talking about this earlier today just about, you know, humility and how important that is, you know, and I think everybody goes through different phases in their in their lives. But the season that I’m in, the season that Nick and I were kind of aligning on, it’s just like how how little it is to like a kind of self recognition or, you know, we see it all the time in our industry. Like, you know, so and so is

Nick LoPresti (09:15.458)

the innovator of the year because he stuffed the ballot for himself to go and become the innovator of the year with investment news or whatever. I suppose we could have had a lot more awards over the years, but it never cared. It almost is at a point of disdain for all the industry awards and the who’s who and the this is that because your life is a compilation of all the things that you do.

But the output of that is what’s important. Are you building something transformative? Are you affecting lives? We think about the advisors that we serve, and those advisors have created hundreds of millions of dollars, if not billions of dollars for their clients. And you then get two personas out of that. You get the people that are, you know, the chest beating, like, man, look at all this great stuff that I’ve done. And then you people that have just walked with humility. And I respect that so much, you know.

we’ve had the good fortune of being around some great leaders in our careers that, you know, and to me, I’ve always gravitated towards those that have chosen that sort of quieter path to success and just let that body of work be the thing that people will judge them by, rather than the weird shiny trophy that might mean something mostly to them, but for one night might mean something to a group, a room full of people. But in end, it doesn’t matter. I mean,

Top of my head, would never mention the name, but I think about somebody that won an award this time last year. But they’re terrible person. So that’s really cool. You had this awesome thing that you get to put on a shelf, but you have broken relationships with your spouse and with your kids and your employees don’t like you and your team. So great, I I really love that award sitting on the shelf. So it’s one of those things where think humility is…

best demonstrated by what’s not said versus what is. Absolutely. And Nick, how do you test for that? know, from a talent management standpoint. Or hire for that. Yeah. Yeah. Hire for that. Yeah. Because you want, you want people to tell you how, how good they are, right? In the interview process. Right. And I’ve been asked that as like a coach to candidates in my career, just like, Hey, how do I approach like, especially coming out of the military?

Nick LoPresti (11:37.634)

we’re taught not to put the focus on us. mean, it’s always on the team, which I so appreciate you doing now. It just brings me back to the military days. It’s about those around us. And, you know, I didn’t get that award. It was my team that, you know, was the reason we got it. And so it’s hard to do that. You know, there’s a balance and you could you could see humility when someone’s, you know, speaking and you could see arrogance when someone’s speaking. And I think maybe that’s a skill in itself is being able to determine that. But it’s very obvious when someone’s trying to showcase

their humility, which is to your point earlier, is when we say we’re humble, it usually means we’re not. And so I think, especially during the interview process as a leader hiring, hearing just their way of speaking about themselves, are they comfortable? Are they really overly confident? Are they deflecting to their team also? Like, hey, I did accomplish this, but I had a great team around me and here’s how I led that team rather than just saying like, I, I, I.

And you can incorporate I into that right because we want to know we’re hiring the right person But if if you’re deflecting often as well and striking that right balance Usually that will result in at least you know, hey this person seems, you know, they know what they’re doing We’re confident in their ability But they’re also not gonna come here and be arrogant and try to steamroll over everyone because they know best right? Was that a like preemptive question? Did you think of that one? Yeah, it’s really good. I was damn good that wasn’t the best question you’ve ever asked. Thank you. Yeah. Thank you

So one of the experiences I had with you, went to, I had the opportunity, and thank you for the invite, because it was really cool, went to a change of command ceremony, which I didn’t really know what that was as a civilian, and I got to go to Eielson Air Force Base in Fairbanks, Alaska. I think I drove by and I came to find out it was the last remaining blockbuster.

In what? Yeah, no way. Yep, still open still open North Pole, Alaska the North Pole Alaska So that was part of the trip. That’s how you got to Isle Air Force Base. I didn’t know what I was getting into I didn’t know what this whole thing was show up at the airbase having what you tell me have your ID ready. Mm-hmm. Sounds good And I get there and I go into this little building, you know, like a guard shack, I guess you might say and

Nick LoPresti (13:58.05)

There’s Ben’s picture on the wall right next to president Trump. And I’m thinking, this guy’s done some stuff. I see where he’s been. This is, this is how it works now. This is, this is where it is. And, you know, it got me thinking a little bit about when you’re in charge of that many people now, right? You’re at that level of leadership. Like how do you balance the, being accessible.

versus being approachable? Yeah. I think that’s a great question. And I think, you know, that story of having my picture on the wall and, Nick, you’ll appreciate it, you know, the change of command, right? And every Airman in the Air Force needs to know who their boss is. And then ultimately it goes up to the president, right? And being in that chain of command, there is a responsibility that you assume. And I think, you know, part of that approach and part of executing that responsible

Responsibility is embracing humility like we were talking about and making sure it’s you know, when you’re in a position like that It’s not about you. It’s about what you can do in order to support the organization that you’ve been charged to command to accomplish the mission You didn’t take care of the people in order to do that So I think you know having that humility having that approach ability is super important And I think when I was in that position and when I’m in leadership positions even today what I want the people to know who I lead

is I just want them to know that I care. Right. And then they need to know, when they see you, you want to be approachable and you want them to know that you have their best interest in mind. You also have the best interest of the organization and then the mission you have to accomplish. And you’re, you want all those to be in harmony with each other. Now that mean doesn’t mean that everyone in the organization of two or 3000 people can just show up your door and

Yeah, how do you operational stuff? Yes. So and you have to be present, right? You have to be present in managing, you know, the operations and there’s a time critical nature, but not everything is requires, you know, that time. So I always think of what’s the urgent important thing that needs to be done in that to qualify your time. But you also need to carve time for things that are important, but not urgent. And you can balance that through having a good team around you.

Nick LoPresti (16:22.784)

and making sure if somebody does show up your office, you know, and being able to understand what they’re concerned about. What I always like to say is like, this is super important. I want to make sure I take the time to understand your concerns and think about it. Can I schedule a time for you to, you know, to come back? So that’s kind of how I would, you know, balance that approachability, but also making sure that, you know, I’m controlling my time and to do things only I could do as that leader.

the, if you can embrace that and then also put that, infuse that mentality down through your team, you have everyone that’s thinking about how can they, you know, execute the highest level and do the things that only they can do. And then also delegate those things. Cause those delegation opportunities are growth opportunities for other people. And I think that’s how you can help really, you know, infuse this culture of growth with an organization.

By aligning that and we’ve talked about, you know strategy and operations and you know, how do you put that together? How do you you know meld that with the people you bring on your team? I think it’s Really important for leaders to think through those different lenses. Yeah, that’s right and Conor. good I just want to jump in there’s one thing you said want to make sure it gets said again You said people don’t care how much you know until they know how much you care. Yes, that is so critical We learned it in the military, you know, especially as an officer leading

But I saw that in my leaders, you know, they cared, at least, know, the majority of them did. And wow, did I want to follow them into hell and back because of their care for us. And then when they taught us, you know, we were, you know, just sponges, right? Because we knew they cared. I just want to triple click that too, because that’s like the first word that comes to mind. Just care, like care about yourself. You’re going to take, you have the discipline to make sure you’re doing things to take care of your temple, right?

As the body you care about the mission you’re gonna make those hard decisions that and you know require That mission requires and if you care about the people it helps again keep keeps that harmony. Yeah, that’s right That’s a point. Yeah and Conor. about you? How do you balance that being approachable versus being? Accessible right because you sit in an office where you got people, you know They can see in your office because you chose to put glass Into your office so they know you’re there right? There’s no hiding. You can’t go and hide

Nick LoPresti (18:43.406)

Like how do you balance that as a leader? Yeah, it’s hard. You know, I mean, it’s we’ve talked about it with even when you think about being an advisor and the clients meeting the clients needs, meeting them where they’re at. And you have clients that, you know, have multi-millions of dollars with you. And oftentimes they’re they don’t you talk to them twice a year. You wish them a happy birthday and they wish you a happy birthday. And then you have some of the clients that maybe don’t have as much, but they’re calling you every three days.

and has always been a struggle because I think people appreciate authenticity and when you authentically care about them. And that’s one of the hardest things to balance, especially as you grow and as the business grows, as your responsibilities grow and change, as personal life develops. I remember being new advisor as a teenager and

staring at a blank calendar and being like, how do I make this thing look busy? And now I look at that busy calendar and I’m like, how do they make this thing look blanker? But I think part of that, you and I never had to go to war. God. And you and I haven’t had the experience that they have from a military standpoint. But I think a lot of our DNA is built on that idea that if you pick up the phone and call us,

we’re gonna answer, you know? And that gets challenged as you build a company or as you build your private practice. And finding that balance is tough. It’s probably the hardest thing to do. It’s not that you can’t help people, it’s that you have to manage how you’re sort of investing into those people. I’m terrible at it.

And I would back it up even a step, especially for the advisors who might be listening today. Step one is do you recognize yourself as Do you recognize the role that you play not only with your clients, but potentially with your staff? And growing those leadership skills is just as important as growing your knowledge of running portfolios. If you really want your business to

Nick LoPresti (21:03.638)

grow exponentially, it comes down to can you grow your own leadership abilities for your your practice? So a lot of overlap there. You mentioned something kind of interesting, and we’ve all had some conversations around the idea of like you have the culture of the organization. You have the strategy of the organization.

There’s operational things that we have to do. And I’ve always been a big believer that look, strategy sometimes is where, you know, execution goes to die, right? You ever talk to somebody who’s just not clicking, they’re not performing, they’re not hitting on anything, you know where they wanna be? They wanna be in the strategy room, right? Where all the talking’s going on but no doing over there. And so there’s this balance that you have to have. How important is culture to

Strategy mm-hmm you ever thought on yeah, I’ll jump in on that one so as someone that has a PhD in strategy mm-hmm I couldn’t agree more that strategy You know in order for it to have value has to inform operations and inform daily decisions. Mm-hmm. There’s a saying out there to like Culture eats strategy for lunch. All right, so if you have a strategy or something on a you know vision statement and but that’s

the only place that resides in the only place that lives, then it’s not really a strategy. It’s just a showpiece. So when I think of strategy, I think of how do you alter context for continued advantage? And then how does that, what are you trying to achieve as a team? And we’ve talked about teams and that humility to understand like, okay, we all have more to learn, but this is where we’re going and this is where we’re going as a team. And then, when I was in leadership positions, I always think of, right, I’m going to

write down my strategy in terms of this is where I think the organization needs to go. This is where we’re moving out. Everyone makes it aware. But when I make decisions, I always made a deliberate, you know, kind of mention of, this is why I’m making this decision, because this links to our strategy. This is where we’re going. So they understand the why behind it. And I think that is how

Nick LoPresti (23:21.388)

you can align those efforts and that really gets into what kind of team you want to become and the culture that you value. And what do you celebrate? Conor, do your earlier point, like if you have ceremonies or awards in your organization, does it actually align to your strategy? Where do you want to go? Do you want to be an innovative organization that’s growing and constantly thinking of new ideas? Do you want to be more stable organization? You should think through what you, what you celebrate. And then that.

kind of people you want to bring into your organizations, maybe the kind of people that need to maybe go on to their next journey and their seasons of life and pull all that together. But ultimately, like you, like you alluded to, how does this inform the decision that I’m making now? And having that kind of, you know, short term mindset aligned to where you’re going as organizations. And that’s really difficult to do and challenging and something I struggle with today, but

I always think when I’m struggling with something, that’s a good sign because again, about it. So I’m going to the effort in. So that’s where the growth happens. I struggle with my marriage. It’s hard, right? Cause I work at it. Right. And it’s this, you know, it’s those things that I cherish the most of my life. So, and I think if you, yeah, that authenticity comes like Conor, you were mentioned if, you know, leaders are able to show that, I think it can be in my experience, very powerful and also a lot of fun.

Yeah, for sure. And so Nick you’re in the culture business Right. It’s the business business because culture is is really the you know, it’s the people Yeah, right the people determine the culture. You’re in the culture business. How do you see the you know? intersection between strategy and Culture, how does that mean for you from your seat? Yeah. Well, I think to Ben’s point, you know, you need to have the why

why, you know, the why behind everything, why are we doing what we’re doing today? Even the, you know, the trivial tasks, like is this pointing to a, you know, bigger strategy? So strategy’s critical for several reasons, but employees come to work every day. Yes, for, you know, they want to get paid, of course, but they also want to know that the work they’re putting in is actually going to mean something. I’ve been part of projects that, you know, there was no strategy in place from senior leadership, and so it died out after like six months, and it’s like the last six months spending 20 hours a week on it.

Nick LoPresti (25:45.325)

You know, it’s just kind of gone, you know, and there was no value that I added because we didn’t you know There was no strategy built around it You know culture is a whole separate topic just in terms of like how is that created? How is it cultivated? But ultimately, you know your strategy should determine what kind of culture do you want? mean, you you see these high-tech companies that move very quickly hyper for you know, really a lot of performance tension high performance culture but that creates a lot of you know, stress and anxiety which

the senior leadership might want and that’s their strategy is to create that environment where people feel the need to compete with each other. Now there’s healthy competition for sure, but sometimes it could go on the one ditch where it’s just too much, right? And you come to work every day feeling like you’re inadequate. But then there’s the other side where you’re very clear in your strategy, you’re very clear in the people that you have today or the people that you want tomorrow and being able to…

have a shared vision aligned to that strategy is really important because if you don’t, people are coming to work every day not being really clear on what the reasons are that why they’re doing it and that will impact the team chemistry, the team culture. But to your point, it’s the people, not the things you put in place that determine the culture. So lot of companies still to this day, surprisingly, many years after case study and after case study, it’s not the ping pong tables, it’s not the music or whatever you’re doing, right? Those are…

fun things, but that’s not what creates culture. You have a culture where you’re not building strategy and you have team members spinning their wheels for six months on a project that ultimately doesn’t go anywhere. That’s culture. And that will impact severely, you know, the people and how they show up to work each day. Sure. And Conor, I mean, since you and I have been working together, we’ve seen some cultural shifts inside of good life, right? How’d you make it happen? What’s it?

The cultural shift. So, you know, I think that the we saw big shifts back and forth to especially with everything that happened with COVID and whatnot. And I think the thing for us was staying grounded in what we were hoping to deliver in terms of an employee experience versus versus following the trend, you know, because you can get easily sucked into the trend. And, you know, it’s great to know.

Nick LoPresti (28:11.308)

and to get the people that are giving you the insights around what’s happening in other organizations or in the overall economy, but to be able to then discern and make good decisions. And our employees saw us going into different seasons, having to make those calls and whatnot. And I think what can stay consistent through the whole thing was like where our intention was.

and aligning that intention with the overall purpose and passion of the business and not losing sight of those even if constraints outside of the buildings that we were operating from changed the way that our employees were engaging with their job every day. You know, again, you look back and it’s very easy to play Monday morning quarterback, well, we could have done this or we should have done that. But if you stay convicted in what your beliefs are,

And you don’t let those extraneous forces impact that then I think at the very least even if you called the wrong play You’ll still have the backing of your people. know, and for us by the way, it’s Saturday morning quarterback because Saturday mornings are where the decision happens. Yeah, that’s where the coffee time happens. I would say you know, one of the things that’s really interesting about good life is I would look at the culture and I’d say it’s been something that you’ve

Protected really well because we haven’t seen ever in my time with Good life where you’ve lost a lot of people I’ve seen it where we’ve had to make some tough decisions around the people in the organization in order to Protect the culture. That’s Right and that to me is one of those Defining

attributes that you know an organization will be successful is when you’re protective of the culture that you want and when someone doesn’t fit it, you got to make a tough decision. And so there are, I think about the culture that we’ve created there, which is, you know, you’ve been able to successfully take a lot of folks

Nick LoPresti (30:32.46)

get them on the train and take them to a higher level and they’re still with you, which is an attribute of a great leader. And I think a lot of it has to do with just protecting of that, that culture. Yeah. Well, you got to love your people. You know, obviously you got to love the product of the service that you’re delivering, but if you’re doing it around people that you don’t like, it just makes the job harder and you start to resent it and they start to resent you and it creates, it fosters those types of conditions and, genuinely love the

the people that we’ve had the opportunity to work with in the last 14 years. I’m smiling because I just remember distinctly like a decade long person that was with us and new leadership came in and was like, I just had it out for her and like presented the whole business case. And I just remember looking just like I’m looking at you with a big smile on my face. like, appreciate your insight, but she’s

there’s not a chance in hell that I’m turning my back on that person. And I think that set a tone that I think was good. Because people were like, hey, he’s got my back no matter what. to me, it doesn’t matter if you have your PhD in whatever the discipline is, if you ask leadership to cross somebody that they’re invested in,

and their investment starts here in their heart, then if I would have made that, if I would have called that other play or been influenced by that, it would have changed, that would have been a culture changing moment. And it just wasn’t worth it to me. There wasn’t a price tag or a lack of discipline that would have been out there that would have changed our mind on that. Yeah, and that’s something that so many companies don’t recognize and stop, right? Because that leader that, you you had to, you know, you had to,

Stop, you know, and seen it in so many different companies, know, large companies where a leader comes in and they just bring in all their people and they want to fire everyone else. Right. That’s working for them, regardless if they’re good. And that impacts culture. And so to be able to stand firm on who you have with you is rare today. So kudos to you for doing that. And so critical to get that message out that you don’t have to let your leaders come in. You hire an executive. They don’t have to come in and replace everyone.

Nick LoPresti (32:57.87)

You know, you need to, you know, keep that, you know, keep that, that team chemistry alive because people don’t realize, leaders don’t realize it can destroy a culture. And so what you did there is lasting impact on that person, whether or not they knew that was happening or that leader, right, that learned from it, even if that created frustration. So. Absolutely. And if you’re an advisor listening to this, our council would be, I’m speaking for the group.

See how I said our council me speaking for the group depends just to think about think about your culture in your organization Even if it’s just you and someone else If but if you have a team and I went in and asked what’s the culture of you know? Lepresti financial, what would they say? And if you’re thinking about you don’t know the answer to that You probably have a culture problem or if you if you think

They love me. You also probably have a culture problem. probably have a culture problem. Factor of humility. exactly. Yep. So culture and where it intersects with strategy is so important for any organization. Absolutely a big topic. Conor, any closing thoughts that you have? Any closing questions that you have? First of all,

Thankfully these two men for their service. Absolutely. Thank you guys. And you know, when you have the opportunity to line up next to guys that have lined up in far worse places than this, it ended up itself as humble, just a humble moment. So very grateful for that. And just love the stop topic. I think if you can get the people part of the organization right, no matter how many people are involved, whether that’s the people that are in the trenches, you know, digging the hole with the financial advisors.

or it’s the clients that they’re serving. If you understand the motivations of that person’s heart that you get the opportunity to serve, changes everything. Changes how you interact, changes how you bring intuition to the situation, and just a cool subject to talk about. We could do it all day. Yeah, absolutely. We absolutely could. Maybe even after this is over, we’ll go find a place to pull up and…

Nick LoPresti (35:17.774)

talk leadership. Yeah, Kevin McAllister sounds good. Say we have a house to see 16 minutes away. Sounds like we have a house to go see. Yeah. Nick, thanks for joining us. Ben, thanks for joining us. Thanks for letting me be part of everybody next time on another episode of thinking independently with Conor Delaney.