A Decade of Building XYPN from the Inside Out

Alan: Hello, and welcome to this episode of Behind the Advisor. I'm your host today, Alan Moore, and today is a little bit different of an interview, and it is with Maddy Roach. Your host that you've been listening to for years and employee number one here at XYPN and Maddy recently shared with us that she has decided to pursue a new opportunity that we are super proud of her for and, and very excited, but we wanted to have her on the podcast so that she could share her journey here at XYPN, what it's been like over the last 11 years, uh, and some of her takeaways and learnings that she's gonna be taking into her next opportunity. So it's certainly a bittersweet episode, but, so proud of her and, and so grateful for what she has done here at XYPN. So without further ado, here's Maddy.

Alan: Hey Maddy. Welcome to the show in the Other Seat as the interviewee. Welcome to the show.

Maddy: Thank you, Alan. It is nice to be back and it is always fun to be the one being interviewed.

Alan: Yeah, I'd actually meant to look and see how many times you've been the interviewee. It's been a couple, like probably three times over the years.

Maddy: Yep. I think two or three times. And I'm sure we can put those links in the show notes, but we've talked all about the different development points of XY together and this is a special episode today.

Alan: I would encourage folks, it's always fun to go back and listen to the episodes over time. 'Cause one, they hear just our evolution and what has happened in our lives. 'Cause, you know, it's been a lot and they sort of hear like where you were at at different points in that journey. And so it's really easy now to look back and be like, oh, that first year was so amazing, but when we recorded a podcast in that first year, it's like, whoa, this is tough.

So hindsight is 2020 on these things.

Maddy: Always.

Alan: So we are here to sort of recap the last, what is almost 11 years of you and I working together here at XYPN. And it's a bittersweet episode because this is our sendoff for you. Uh, because you are, you have let us know that you're gonna be moving on to new opportunities and we’re super excited for that and what you have coming up. So we're gonna dig into all of those things. Just want to, sort of want to set the stage for folks that we're gonna be going through, sort of your, your journey here and what it's been like at XYPN. and like I said, at the end we'll share what's next for you.

Maddy: Absolutely.

Alan: So I guess just for folks who maybe are tuning in for the first time, let's sort of set the stage on who Maddy is. So can you just give a brief background on sort of your who, what role you have played here at XYPN?

Maddy: Sure. Uh, hello listeners, if you haven't tuned in before. Welcome.  I am Maddy and I am XY PNS first employee, which means I've been with the team for almost 11 years. And throughout those years I've worn a lot of different hats, but primarily been on the membership side, on the leadership and development side of building some of the teams and the programs and the offerings that we've offered to members over the years.

 I took a real focus in culture development within our community.  working on retention and making sure churn was reduced over the years.  but most recently around year nine and a half of my tenure with XY, I transitioned into an executive business coach role, which has allowed me to kind of recycle a lot of what I've learned over the years of working with our thousands of advisors back into our advisors, which has been really fulfilling.

Alan: Absolutely. Yeah. I mean, it really is incredible to think 11 years ago when you started here, I didn't have any kids, and now I have four, and the oldest is turning 11 this year. Uh, you know, we didn't have an office. We weren't in Montana. It was me living in an RV and. Somewhere between Bozeman and Milwaukee at times, and you were in Seattle.

Like it's, it really is amazing to kind of look back over the last 10 years and think about the amount of things that have happened over the last 10 years and then sort of appreciate that the same amount of change and, you know, evolution and growth can happen over the next 10, which is what's exciting.

It's so easy to be like, oh, we'll just keep doing the same thing, but we won't. We're gonna, we're gonna continue to grow.

Maddy: Yeah, and I, I think you know this too, that we as humans kind of live in this like seven to 10 year cyclical process within ourselves, and when we think about the future, we really can only think about five to seven years out. It was always very hard to picture when we first started at XY what. Year 11 would look like, and I certainly wouldn't have pictured this.

And leaving XYPN and resigning from this incredible opportunity is bittersweet, to say the least. But I feel that pull again of it's, it's time for the next big iteration of the next 10 or so years, and looking back at what we've accomplished has given me a lot of confidence in seeing what could possibly happen in the next step.

Alan: I believe it's strength to strength. He talks about that sometimes change is initiated by being pushed, and so this could be, you know, you've been fired or you have to relocate for your partner or something like that. You get pushed out of the nest, if you will. Sometimes you get pulled. There's this amazing opportunity and you just can't say no to it.

And so you kinda get pulled into this next step. Other times you just change for the sake of change because change is what you want and you don't actually have a, what, what some might consider a good reason.  but you don't need one like that. That's the point. And so I think that's hard for me.

I always want a grand plan. I need the next thing before I stop doing the current thing. But,  you know, recognizing that you're, you're absolutely right that change is inevitable and that cycle. Is, is just how we all live.

Maddy: Mm-hmm.

Alan: So let's go back 11 years ago now.  in, well, from the date of this recording in I believe eight days we will, or nine days, we will hit our 11 year anniversary of when we launched XYPN.

Uh, and so, you know, for listeners' benefit, April 4th, 2014 is when we launched XYPN and immediately we were just sort of inundated with interest. Now it's funny because the interest then, you know, compared to now is just so small, but it was just me and we immediately said, we've gotta hire somebody.

And the story goes that Michael asked me, he said, you know, you need to write a job description. I said, I don't have time to write a job description. He said, well, what? I said, I don't even know what to call this position. And he said, well, what do you need them to do? I said, I don't know. I just need them to get shit done.

Like that's just what I need. They just gotta do stuff. And he's like, all right, well, why don't you just call it that? And so we posted for the director of Get Shit Done. And in that interview process we met you. And so tell us a little bit about, sort of from your perspective,  I guess your journey to, to coming to XYPN and how'd you hear about us?

and ultimately what made you decide to take the leap and join a one month old company?

Maddy: In hindsight, it really is, is a different perspective for sure. Uh, but when I was 26 and had the ability to join this company, I did not think twice about it.  and I wouldn’t if I had to do it again. But I was a disgruntled paralegal. I was going into the office every single day working with an organization that I supported, but felt a bit misaligned in.

There was no upward trajectory for me there, and I was trying to figure out how to pay my student loans and live my life in Seattle off of a very small paycheck. And I became somewhat addicted and a hobbyist of my own personal finances. And I started blogging and the blog no longer exists and it just kills me.

I don't have any of this content that I wrote for years, but,  I maintained a blog about personal finances and I learned about the CFP curriculum and I was just like, there's my career path. That's what I've gotta do. Uh, I didn't want to go to law school anymore. I wanted to get out of what I was doing, and I started networking and I just, I remember the feeling of hunger in me that time of my life was so strong that like something had to change, something had to change and I was willing to talk to anyone about it. And it was really the first time I had these awkward conversations with people in the industry that just were icky and they thought I wouldn't understand. And finally through lots of networking, I stumbled across a woman who has been a long-term mentor of mine, and she was a founding member of XY and she was able to make the introduction to us.

And I don't think I understood the opportunity when I made the application video and jumped on the team, and I'm so damn thankful I did.

Alan: Yeah, Google has done, I mean, they've spent hundreds of millions of dollars trying to figure out how to hire well, because it's really hard. And for listeners, as you think about hiring your first and second and third team member, it is so hard to hire and to know what you're getting in for and describe the opportunity and hire the right person and all the things.

Uh, but the one thing they have found that works exceptionally well is they would say employee referrals, so a current employee referring someone to become an employee of the company. For us, we didn't have any employees, and so it was a referral from a member who truly, you know, Kate really understood our mission and what we were trying to do, and she could probably see that I was drowning and needed help, and it was like, all right.

She'll make the right connection. And so, you know, that was it. It's really interesting. You know, why I would encourage folks to leverage your network because that's how you find really, really good people. And a lot of our team members have come from, you know, either they were members, they're friends of members, they are married to a member.

They, no, one of our team members, we've had couples working here before. So it's, it's really kind of cool to see.

Maddy: Yeah, absolutely.

Alan: So I also like to think about that first month. You know, I had never managed anybody before. The biggest company I ever worked at had five employees, not a great working, working environment.

So I didn't even know anything about running a business. Well, I guess I knew some about running a solo business, but not with employees. I'd never run payroll for anybody else. For me, you know, part of my personal story is I was going through a pretty messy divorce at the time. And so I was sort of like between homes, I didn't know where I was gonna end up. And then we hired and then you joined the team. And so it's like, all right, so what do we, what do we do? And so I did what anyone does. I bought a Google Chromebook on uh, on Amazon and shipped it to your house, and I don't know how many years did you work off of that?

Maddy: I was like four or five. I mean, I think we were really rocking the Chromebook for a long time. We didn't need anything more.

Alan: No, we did it, it was great. I remember thinking like, oh, this is great. We can't use desktop software. You can't download docs to your web or to your computer because it's a Chromebook. It can't do - So funny how that works, but I'm curious sort of what your early memories were both positive and negative.

I mean, it wasn't all rainbows and unicorns. Like what were those early memories of like, you know, was it. Hey, this is amazing. Or was it, oh my gosh, what did I do? Or sort of a mixture of both.

Maddy: It was a mixture of both. And it's so funny, Alan, to be having this conversation because part of my offboarding with XY is that I need to go through my Google Drive and, you know, Maddy, 11 years ago, didn't have the kind of naming conventions I have now, and I have. Endless amounts of things on my Google Drive that have been like an archive of our work together.

And so I've been looking at those, you know, notes with conversation. With Alan notes, you know, 20, 20 14, and it's wild to see. You would call me once a day and wherever I was, I would be taking the call and I'd have my Chromebook and I put you on speaker phone and rapid fire the way that you are, you know, just boom, boom, boom.

Here's all the things we gotta do. And I just took notes and we'd hang up and it would be like, I have 24 hours to get most of this shit done. And it was so fun and I've always prided myself on, you know, with good leadership and direction. I can execute really well and I really was attracted to your clarity on what needed to get done.

I wasn't in the position early on to be able to like, drive the direction of the organization, nor were you interested in me doing that. But you had real understanding of what you needed to take off your plate at that time and delegate. And I was hungry for any kind of work. And now to think that there's over a hundred teammates doing it.

Parts of the work that we were doing originally is just wild. But it really is true that so much of what the tech team's working on is, is what we did manually many years ago. And the freedom that you gave me to work on my own terms was, I think, what allowed me to realize I have a totally different amount of skill to provide an organization.

'cause with that kind of privacy and my ability to be where I needed to be to get the work done, allowed me to work at a higher level than I'd ever worked sitting in an office chair from nine to four / five. And that's where I think the magic for me really came up in both how I want to manage at XY and in the future and how I want to be managed, which is I know myself best and if I can choose when I do the work,  I can do pretty damn good work.

Alan: Yeah, Dan Sullivan with Strategic Coach has aligned that there's no incentive, like no alternative. And I felt that way. Like I wasn't great at delegating. I just didn't have an alternative 'cause I couldn't get it all done. And I look back on that now and I'm, I'm actually really grateful because I do think had I eased into it, I would've had a hard time letting go of things, just because I'm like: I would rather just do it myself than spend the time to train somebody else to do it. But like, that wasn't possible. There wasn't enough time. And honestly, we didn't even know what we needed to do. Like what did it take to onboard a member? Like we were making it up as we went.

And it's incredible now to think about, you know, the processes that you and I had. You know, I remember getting like four members in one month and we were like, oh my gosh, what are we gonna do? Like, we can't onboard four people in a month. Uh, and I'm sure advisors feel that way. If you got four new clients in one month, you would feel completely overwhelmed.

Uh, and we had a month, it's been a couple years ago now, but uh, we had a month where we had 63 new members join and we were fine. You know, we like, we hit it because those things scale. And the same way an advisory firm may get 63 clients in one month, one day but you can't do that day one.

Maddy: Yep.

Alan: So I think your journey really encapsulates one of the real challenges and realities of businesses that grow and continue to grow.

Now, if you just grow to three to five people, this is not going to apply to you, and that's totally fine. That’s awesome to build that type of business we chose to grow. But the challenge is how to help your early team members who are generalists, become specialists.

Because as you grow, there's less room for generalists doing a little bit of everything, and we have to start defining the hats you wear, the seats you sit in the work that you do, and some people cannot make that transition. You made that transition very successfully. So can you talk about, I. Sort of the, the, I guess the couple major roles that you've had here and we can kind of talk about like how you went from the generalist who was, get everything done to the business coach who's very focused on sort of one particular area in helping our members.

Maddy: A majority of my role after being the director of getting Shit Done, which did become a general, you know, was a generalist title, and as we added marketing and sales and some of these other departments compliance early on, I did need to niche a bit in terms of what my focus area was and it made sense for me to own member success, which really was anything that touched the member.

Once they became members was my jam. So from the partnership engagement to tracking the data around churn, to making sure that our members onboarding and offboarding was accurate,  to owning the community and things like that was really where I spent a majority of my early years. That position stayed for multiple years as we grew XY from, you know, a dozen teammates to, you know, 20 or 30 teammates at that point, and I really loved that role. That was my first taste of real management in a position of, you know, hiring the individuals and actually having them report to me.  and I really learned that I loved management at that time and I was really taken with the kind of impact scaling a business through great teammates can have. I just loved building the culture internally. So there's actually times where I, you know, you had asked me, do you want to work? On the XYPN team, or do you want to work with the XYPN member? And I did continue to go back to the member because I just loved our community so much but then we, you know, we staffed the team to own the different departments of membership and eventually I moved.

And the senior director of member success, which included a bit more broad ownership and had to work among different leaders at that time. But,  I think it was right around 2021 right after Covid.  I had, I think one of my harder years at XYPN was during the Covid years. Managing through that was, was one of the hardest things we were going through, a big strategy change.

Considering a couple options that were very difficult for me to synthesize in my mind of the impact it might have on membership and what that could do for them, for me and the community. And I found myself really burnt out. And I remember going to lunch with you and talking about it, and you at that point actually flirted the idea of you could be a coach.

And it just didn't stick to me.  and instead I moved into kind of this, this unique position you, you all developed for me, which was the vice president of getting shit done, which at that time was. A connector and a liaison between all the different department heads of our business lines to make sure that they were aligned and hiring the right people.

I spent a lot of time on XY tax solutions,  and they gave me a year and a half of breathing room and I can't thank you enough for that opportunity to be able to, to continue to contribute, but have no direct reports. Get a minute away from the eight years of management I had had before that and, um.

From there moved into the executive business coach role, which at that point in time, when I accepted that position, it never, I'd never felt more aligned with the position as I do with the business coach role.

Alan: Yeah, like I said, it is a tough transition because you know, when you're just starting out and you're hiring your first team members, again, you've gotta do a little bit of everything. That's just the nature of the job. You can't say, well, I only do membership. I don't do marketing. It's like, no, we all do everything.

But the other reality is that as you hire your second and third and fourth and fifth person, the whole goal is that they are taking things off of employee number one's plate. Like they're taking over the marketing, they're taking over the sales, they're taking over the onboarding, whatever the things are.

And it, you know, and I remember conversations with you early on where it can feel like you're taking my job from me. What am I gonna do? And it's like, well, the. The whole point is that we've gotta specialize, we've gotta start focusing because it's, you know, this, you had like what are now probably 20 full-time jobs at XYPN underneath one, accountability.

And that is something that you have, you have to grow into.

Maddy: And that I think speaks to just like the maturity level that I have experienced over the years and. When I was 26 and I was given this director of getting shit done role. I owned everything. And so it was an ego hit when you said, we're hiring a marketing teammate. I'm like, what? I'm doing the newsletters, you know, and you're, you're very protective of your work early on.

And it's, you know, having spent this amount of time in an organization, I can just see how. How I've had these ups and downs of where I really grew and where I really understood how you run an organization without ego and how you can step aside and say it's time to, to welcome someone else on the team.

And I, I applaud you for your ability to do that early on and give those examples. And it, I think, took me and other teammates a little bit of time to really get behind this vision that no, we are growing and our roles will continually change and we've got a. It's nothing against us. It's about how to run a successful organization.

Alan: Yeah, and especially in the early days, I took it personally when people would, would leave and go to, to new opportunities. And what I learned was just some people are really built for the zero to 10 employee journey and they want to be part of that. Some are built for it, you know, and some folks that you hire when you have 50 team members should have never been on the team when you had.

Five. Uh, and you're one that has been able to grow from one to, you know, over a hundred now and again, we'll talk about your, your next opportunity where in a way you're kind of going back to the one the one stage, which is awesome because you, you know, now what it takes to, to do that. And so, you know, for one of the things that you mentioned was sort of that time where you had sort of this, I don't know, uh.

Ill-defined role, if you will, the vice president of getting shit done. and really we thought of that as, hey, Maddy is a Swiss Army knife. Uh, we got a lot of different things, she's got a lot of different tools in her tool belt and we have a lot of problems like covid was happening and uh, you know, stuff with service lines and challenges.

We were, I was trying to grow up as a CEO, like just organizationally. We had a lot of challenges and so what we. First, you know, what we saw an opportunity was like, Hey, Maddy can kind of bounce around to different messes. If you will help us clean those up, help us get realignment. Uh, and what that ended up being was a little bit of space for you.

And I'm, I'm curious for you to share a little bit about. The space that you've had with particularly, I'm thinking with sabbaticals since you know, this, this decision to move on you said kind of happened during a sabbatical and the sabbatical program is something I'm really proud of and something I hope that more and more of our members will embrace.

So can you just talk about your experience with getting space, whether that be sabbatical or sort of that, that role for the year and a half and how that allowed you to sort of get to where you are.

Maddy: Yeah. And I'll start with the VP of Getting Shit Done It. It was by no means an easy job. I was walking into a kind of triage mode on a number of fronts. But what shifted for me was that the people management and needing to communicate strategy down through my direct reports had become very difficult for me and to manage emotionally, to be able to check out when I needed to, to be able to take a breath.

I felt a huge amount of accountability,  that I felt like just wasn't aligned with where I was at that point in my life. And,  by going into the VP of getting shit done, it did allow me to get that breather of, of just having. Not so many one-on-ones, not so many people issues, things like that.  and I really love getting shit done.

I mean, that, that really is a muscle of mine that I enjoy. And so it felt like a great space for me to be able to prove that I still had valuable experience to offer to the organization and speak at a leadership level, but not do some of that mundane stuff that started to weigh me down over the years.

 but at year five I took a sabbatical and it was probably a very difficult time for me to take a sabbatical 'cause I had a very young team. We were, I was the first teammate outside of you to take one. We were testing it. Could Maddy go away for five weeks. I remember coming back, there was work for me to do, but nothing had imploded and it had only taken me like an hour to get through my emails.

 and I prepared for a whole year for my team to be able to own that.  yet here I am as an individual contributor, taking my 10 years, you know, anniversary sabbatical, which. Equated to about 10 weeks over a holiday break and,  it was. I continue to thank you for the sabbatical program because it was life changing and it was an unbelievable amount of generous time for me to really be myself for the first time ever.

And I've told a lot of people this, that I went right into work after college. I worked every, every summer through, you know, sixth grade until college. So I never really had any time off and outside of my five week sabbatical, I'd never taken extended time off. And this 10 weeks, um. I started it with a 10 day silent meditation course and it was during day five where I was sitting silently of course.

And  I felt a release come over me of an identity that I felt very tied to for a very long time, which was Maddy at XYPN.  and I felt a big level of spaciousness come over me in confidence that I can have an identity that is a different one and it. I left that, that meditation sitting that day being like, oh man, I might be okay leaving XY at some point.

And I had never felt that before where,  I never wanted to leave XY, I still don't want to leave XY, you know, but there's there, there was something that shifted in me where the time off, and it was only in the first couple weeks of my sabbatical that I really realized,  that I think I have another couple trips around the sun with different organizations and  yeah.

Alan: People think of that as a negative of like, oh no, we don't want Maddy feeling like she could leave. But the, the worst pressure that I have ever felt in the organization or in just sort of in my working career is when. I feel like I can't take a breather because if I do, the whole thing's gonna fall apart.

That I'm holding, I'm holding all the cards, I'm holding, you know, I'm spinning 42 plates at once, and I, I don't have a choice. And that is it. It feeds the ego of like, I'm important, I matter. They can't do this without me. It also absolutely fuels the stress because. They can't do it without you. You have to be the one you, you can't get sick, you can't be home when your kids are sick.

You can't take a vacation. And I remember, you know, the sabbatical program, just for listeners' benefit, what we do here is: at the five year mark all of our team members, everyone's eligible for this. You get five weeks and $5,000 and it is paid. These are the questions I always answer.

Our team continues to get their salary. They get a $5,000 bonus to help pay for the sabbatical itself. And whatever those activities are or however you're gonna spend that time at 10 years, it's 10 weeks, $10,000 at 15 years, which no one's hit yet, you know, continues to go.

And I remember. I was walking around the TD Ameritrade conference. I was on the phone with Michael and Raul our, our first COO, and I said, I want to do a sabbatical program. I don't even remember where the idea came from. I probably read it in an article, and I remember Raul said, there's no way we can do that.

We can't afford to have Maddy gone for a month. And I responded with that is a fantastic reason to do it because if we can't afford to have Maddy gone for a month, then we can't afford to ever have her gone. And that was really the, that was really what convinced us that we needed to have this was, Hey, we need to build to a point where Maddy feels like she can be gone for a month for whatever that is.

Uh, and us be okay. And, you know, you mentioned this, but I only took my sabbatical when you did because you came back from your sabbatical. And you, and you asked me, when's yours? And I was like, whatcha talking about? Like, I don't, I don't get sabbaticals. And I don't know if you remember this, but you said, if you don't take one, no one else ever will. and I, that hit me because I was like, I really want everyone to benefit from this program, but like, I don't, I've never taken even a week off much less a month, and, but I saw you do it. You had never taken, you know, a week off, much less a month. and so I appreciate you modeling for me how that could be successful and also pushing me to do it because I think the sabbatical has been.

You know, I don't want to overstate it, but I think it's been life changing for a lot of our team members who have taken it and it's been a wonderful piece for our culture and building the business.

Maddy: And I just so appreciate, Alan, your commitment to it. And as you and I had our conversation just a few weeks ago about my decision to move on, your first response was, this is why we do sabbaticals, Maddy. And there was like, it just was like the softest response to a resignation that someone could have.

And I think, you know, leaders are defined by the number of leaders they help produce. And if your teammates choose to exit after a 10 year run with you to go impact the world in a different way, take pride in it. And I think that's, you know, what, what both you and Michael have done with my choice to leave, that it wasn't, you know, how do we get you to stay or don't go, or things like that.

It was real like this is why we do this is that you don't want teammates that are, you know, meandering through work. You want teammates that are really bought in. And trust me, after my five, my five year sabbatical, I came back like, I'm here for the next five. Like, let's go. I got the clarity and headspace I needed.

And so I just thank you for that and you're, I've watched you over the years build a company so that you can be a great employer and I have no doubt you're the best employer in the state of Montana, let alone, you know, in the country.

Alan: Well, thank you for that. And I don't want my softness to imply that I'm super sad and bummed that you're leaving. And it’s not about that. It's not about like, oh, if I was upset, you know, I would've fought harder. And anything like that. I mean, the reality is everyone, including founders, leave the company at some point. As they say, every business owner exits sometimes willingly, sometimes on a stretcher. But in the end, we all leave our business because the one inevitability is we all die and it's morbid, but it's the reality and it's going to happen. And so every, you know, if you're, if you're thinking about starting a business one day, you will exit your company.

It's hard to imagine, but you will, and every single employee with your company will leave one day. They can leave on good terms, they can leave on bad terms, they can leave willingly, they can leave unwillingly. Uh, but it is going to happen. And so we just have to embrace the fact that this is life, this is the cycle.

And if you can keep someone on your team for three years, that's a win. And I think that's one of the misnomers in our industry is that advisors hire people thinking that they're gonna be there for their entire career. Like every job is like a career long marriage and like, that's not how this works.

Like that, that, that's not it. Uh, we could do a whole different episode on that, but.

Maddy: Yeah. Yeah. But I do talk to advisors a lot about it is that, you know, they hire someone so they can double their business and it's like, wait a second that you're walking out onto no man's land, because if that person leaves, you've got double the business and only you to run it. And so there is these like stress tests that you can put in.

Like sabbatical programs to make sure that your company is safe if a teammate needs to exit for a while or take an emergency break for a few months. And I, I think we should always be,  holding things less tightly around that this has to be this way the rest of our lives, as opposed to building a really,  fluid organization that can support ups and downs like we have over the years.

Alan: Yeah. And it's funny how things are serendipitous, so, right. Uh, I think the day before you, you met with me to let me know that you were gonna be moving on. I had read a report, it was like a LinkedIn thing up in the top corner with their news articles and it was talking about Skype being shut down by Microsoft.

So Microsoft bought Skype years ago for like $11 billion. They're sun setting that program. And they had a quote from the co-founder, which so often I see the co-founders be like, oh, I can't believe they're shutting down my baby. They ran into the ground. They did all, they made all these mistakes, and what he said was, I'm sad that it's happening.

I'm sad that, you know, he's not with the company anymore. But he said, I'm sad that they're, they're getting rid of the thing that I built, but the thing I'm most proud of. Are the 1900 Skype alumni that have gone on to start businesses and to have an impact on the world. and I read that, and then the next day you sat me down and gave me the news.

And I remember just thinking like. Maddy's one of our 1900. Like we're not at 1900 yet. But like I hope that I, I hope to be able to look back and say that we, we had 1900 people who were part of our team and have gone on to do amazing work. Whether that's being a founder or being employee number one, or being a, a wonderful parent, whatever that journey is that's something I think we can be proud of.

Maddy: Totally.

Alan: So, I guess let's skip to or, or sort of move to like what's next for you, Maddy. We sent on an email to all of our members announcing this, but we didn't say where you were headed. So can you just talk about what's next for you? What, what's getting you excited about this next phase in your journey?

Maddy: Sure. Not everyone knows, but I am a child free woman and I have chosen not to have children throughout my life. And that has been part of an identity that I've found myself aligned with and also kind of shaping and really impacting the future that I can have, both in terms of what kind of work I can do, how I want to spend my time, how I want to financially plan for myself and things like that. But questions around kind of estate planning do change for people like me and people who are older than me that don't have next of kin. And so,  over the past several months, I've had a. A couple conversations with Jay Zigman, who's the founder of Child-Free Wealth, and he's really carved out a niche around child-free people, childless people.

 and I'm not involved in the financial planning firm at all, but he is spooling up with one other, couple other teammates.  the ability to. Provide financial and medical power of attorney services to people without kids, which does not exist in the industry at this point. And don't ask me why. It's just that it doesn't.

And as I've spent more time learning about the space, I can hear it in conversations even unprompted that advisors have nowhere to send their widows or people without kids to do this. And so it's not just helping them craft those documents, it's actually providing a service of support to them in an ongoing fashion.

I’m really drawn to bringing this to the market, to changing the way trust services are provided and built. It is an opportunity to be at a startup again on the ground floor. I'll be running sales and marketing over there and helping the team get in front of the right audiences and sell the message of why this is so important.

Alan: So really this is trustee services, or maybe we'll have Jay on at some point to talk to us about it as well. But like are these are trust services or trustee services or

Maddy: Some of it is traditional trust service. Yes.  I won't be working at the trust company. The trust company is, is a, is a third party,  to us. But the product that we are building is a technology and the service offering to provide ongoing relationship with the individuals. In the case that they do need trust services executive services or any of the,  kind of hourly offering of financial and medical power of attorney services in case of emergencies or in the case of you just need the trust come over.

So a lot of studies are coming out, people are interested,  trust and will just came out with a big study that over a third of people would rather have a fiduciary work. Fiduciary organizations act on their behalf versus a family member. The tides are changing a bit in terms of, you know, just the complexities of what it's like to ask your partner to make these decisions when they're grieving the kind of elder abuse that can happen if you don't have the right people and,  structures in place to protect you.

So, um. It's just a space that I've actually been very drawn to. And as I learn about the aging solo population, I have a lot of empathy for them. And it is an existential crisis. And,  I never thought I could be more passionate about XY in my life. And here I am being extremely passionate about another organization.

And I think that is a, a a, a hat tip to XY and allowing me to live in a space where I know I'm, I'm jazzed about. Something. And I, I've held that bar very high and,  I've had opportunities throughout the years to, to jump to other places and I haven't even given 'em a fair shake. 'cause I, I, it just doesn't ja jazz me up the way,  this new opportunity does.

Alan: Yeah, I mean, look, had you told me like you were gonna go sell insurance for you know, like, I, I would've

Maddy: Could you.

Alan: a little bit. You'd probably be pretty good at it, but,  I would, you know. But this is so, and obviously you can do whatever you want to do with your career, but it's so mission aligned. I mean, part of our core values here at XYPN is being mission driven and people get that confused when they, when they see mission driven, they think everyone comes in bleeding, the XY, pns, blue and green, and they just love what we do.

Very, very few team members know when they're joining this organization, what we actually do. Even people from the industry don't really get it. It's not about being mission-driven to XY PNS mission. It is about being somebody who is mission-driven, who wants to be part of something that's both. Build, building a successful business, but also doing good, something that has a positive impact on the world.

And that's it. You know, at least from, from what you've described to me, this opportunity sounds exactly in line with that and not. Too dissimilar to the journey we've had at XY of, you know, something that seems so obvious and no one's built it. Why not? And getting it launched and you know, you're gonna get, you know this, you're gonna get a lot of hate because some folks are very, very cruel and mean to, to folks who choose to be child free or who are child free.

Um. And we got a lot of that too in the early days, and that's just part of a mission-driven company is that you're just gonna, you're gonna make some people mad and that's okay. And you've been through this journey. You know what to expect.

Maddy: And I just can't reiterate enough how lucky I feel to have woken up every day for the past nearly 11 years and loved the work I was doing. and as I was in the meditation course, it talks a lot about doing work that does well by people and being in industries that are positive for the world.

And here I am, I'm not, you know, working for an alcohol industry. I'm not working for, you know, an insurance company that's, you know, monopolizing off of the backs of people instead. I've been working every day for a mission that feels deeply aligned and a child-free legacy has offered another additional point of alignment for me, both in terms of my identity and the work I want to do.

 and I, I hope the rest of my life I get to be someone that has worked at mission-driven organizations. And I think the more advisors can think about getting clear on what their mission is and their impact and how they impact the lives of their clients, the better you can pitch the organization to your future hires and allow them to get jazzed by all the work they do.

Alan: So, switching gears a little bit, like what, what about personally, you know, you live in Bozeman, you're here at the office you're here at hq, if you will. What, what do you, I guess, what's coming up for you personally going forward with this new opportunity?

Maddy: I'll be vulnerable. Although I felt very clear about my decision there's some imposter syndrome coming up. There's some anxiety that's coming up. I've always prided myself in being able to get lots of sleep and finding myself waking up in the middle of the night with some heart palpitations, just about the big shift.

And part of what draws me to make this change is that I think from my perspective, my ego needs a shift. And again, that kind of came back to some of the meditation, that work that I was doing in sabbatical of. I felt very comfortable at XY and there's something about comfort that is deeply healing for me.

But I think I also healed through my time at XY and now I'm ready to become uncomfortable again. And I think I want my life to be kind of some ups and downs like that. And,  I won't lie the emails in my inbox that say your departure interview from XY and you know, being told I need to turn in my.

Credit card and my keys and my parking spot, and I can't come into the office anymore in less than a week. It makes me very, very sad. It's bittersweet. I found myself tearing up at the end of a coaching call yesterday. I found myself tearing up in a different point yesterday.  it's been a huge, huge, beautiful opportunity to do what we've done and I'm so proud of it.

Alan: Yeah, and I just want to be clear for listeners, Maddy is welcome into the office any day. We just have a lock system, so you don't have a key card anymore, but you are always welcome back into the

Maddy: Thank you.  but from a personal perspective, the first question most people ask is: are you gonna stay in Bozeman? And I, again, thank XY for the opportunity to move out of big city life and into a place like Montana that feels,  deeply calming to my body and my nervous system. And I feel so lucky I get to walk my big, beautiful dogs outside in the mountains every single day, multiple times a day.

And that's not gonna stop.  I'm gonna continue to take care of my heart and my mind and my soul every day. And my partner and I are really established here and,  really feel like Bozeman's home for now. And,  I feel lucky to have a reason to be here.

Alan: As we come to the end of the episode it is, again, it's bittersweet. It's hard to say goodbye because I'd love to just keep this going 'cause we could, you know, we could talk for days about the, just the journey. And again, hindsight's 2020 we, we kind of tend to remember the rainbows and unicorns portion of it and not the hard part, but it has been hard.

It's been, there's been a lot of tears shed and it has been difficult and it. But also it's been worth it, right? Like we, we've, I, we both feel like we did good work. We've helped people, whether, you know, whatever we go on to do after this, it's like at least we had, you know, my, I I've always said that part of being mission driven here is that we all just want to have some small positive impact.

Make some dent. The universe and it's really exciting to, you know, it makes me happy to be able to look back over the last 11 years and see the more than a dent, the crater that you've made in XYPN and the work that we've been able to do and all the value that we've been able to provide to our members and all the people we've been able to help because of that.

Maddy: Yeah, it's, it's really unbelievable to look back at some of the old newsletters we wrote to members and the old town halls that we hosted and. We all kind of, you know, within the first few years, knew, knew something was up. And now to see the numbers of the advisors who now get to employ people, show up differently that they're to themselves and their families.

 you know, my favorite memories of XY are always XYPN live. And just being able to feel the kind of movement that happened here and the kind of,  culture that we were able to create. And it. It continues to be a culture that will exist long after either you and I are at the organization because of just the beautiful momentum that is getting these advisors together.

 and it has not been easy. There have been lots of times where I thought I would jump and when I'm so thankful for is that,  despite those ups and downs, I always felt like XY had been good to me and I wanted it was a place that I wanted to be. And I feel like I am now in a place where I feel. So confident in the team and so confident in the organization that it doesn't need me anymore.

It feels kind of like full circle and the right time to leave.  and that I think is, wouldn't have been able to be said, had I exited three years ago, or something like that.

Alan: Yeah, totally agree. And I, I thanked you when you, when you did resign, that you waited until we got to a point that we could, we felt like, okay, we'll be okay. Like, we're gonna be sad, we're gonna have a hole that we've gotta fill, or there's gonna be a hole we can't fill. Um. Because I can't replicate 11 years of culture history and knowledge and that sort of thing with a new team member.

But we're gonna be okay. And again, like that's, it seems like that would be a negative, but it is such a good feeling. You know, you convinced me to take my first sabbatical. I'm gonna be taking my second sabbatical here this summer. I'm gonna be gone for 10 weeks. So if, if anyone listening is like, I could never take time off, I'm like.

I'm the CEO of two companies with I think 140 team members between the two. And I'm gonna take 10 weeks off. So chill out like you can do it.  and it's just so important to feel like, all right, I can do great work, but I, I don't have to be the only one. And so,  again, I highly encourage anybody who's thinking about it.

Now, if you're a solo advisor, I get it. Sabbaticals are tough. Uh, but as you begin to grow a team, hopefully you can get that disconnect time.

Maddy: Mm-hmm.

Alan: And with that, I'll say this is not goodbye because Maddy is still going to be in our world, in our ecosystem. Uh, I am sure that we will still see you at XYPN live maybe as a vendor instead of as the mc or maybe both.

I don't know what the plan is. Um. But we'll still, Maddy will still be around you. We'll still get to see her. Uh, for any of you who over the years have, have worked with Maddy or connected with Maddy or, or have that relationship don't worry. She's not, she's not going to sell insurance,

No, I am not, and I'm, I will be around. I do welcome any reach out over LinkedIn or personal email.  I really can't. I've loved the XYPN team, but everyone who's ever met me knows that I just love our membership, so. So freaking much, and it's hard to go through the list of members and think that I won't be working with you day to day.

But,  I will always be your fan and a cheerleader for you and can't wait to, to watch you from the sidelines change, continue to change the industry.

So I'll ask you the final question, Maddy, and that's 11 years ago. If you could go back and give yourself a piece of advice that Maddy, that was in Seattle that got a Chromebook in the mail from a company that got started a month ago, if there's a piece of advice that you wish you could go back and give that.

That younger version of yourself that you think would've helped you in this journey? Something maybe that you're taking to your next adventure that you think is gonna really help you in that journey?

Maddy: It is such a good question. Anytime I think of myself 11 years ago, I get emotional just because I was so different and that's just what's so wild about it and still very much the same person, but so much has changed. I think I would've told her to be more confident in how I showed up. And,  I, I fell into a rhythm with you that you snapped.

I jumped, you said this. I did it. You know, and that worked really well for the first several years, but some of my hardest points at XY was trying to level up into the position of we need you to lead. With your own ideas, Maddy, and push back on the ideas that are coming to you. And,  I think 11 years ago had I brought a little bit more business acumen and confidence into the conversation,  XY may maybe would've been a little different in the, and who knows, but that, that's certainly a new hat that I'm gonna be wearing at x at child-free legacy that I need to be very confident in my decisions.

And, not fall into the employee mindset of having strong personalities around me that are saying we should do this and me immediately deferring.  I have a lot of experience now to offer and,  I think 11 years ago I had experience to offer that, that I maybe didn't share as professionally as I needed to.

So, just a little pep talk to 26-year-old Maddy.

Alan: I love it. Well, Maddy, thank you so much for taking the time to come on the show and kind of reminisce with me on your journey and sort of do this sendoff and we're gonna miss you. And we've loved having you here. I've loved working with you for the last 11 years, but I'm so excited to see this next part of your journey.

So thank you for the time.

Maddy: Thank you, and thank you audience. It has been a total honor to be the host of this podcast for as long as I have. Thank you, Alan, for everything.