The Advisor Delta™

Narrator: Welcome to The Advisor Delta™, the practice management podcast dedicated to helping investment advisors grow their business and reach their goals. Whether you’re looking to scale your practice, streamline operations, adapt to emerging technology, or deliver value to clients - this is the place for actionable insights, thoughtful leadership and innovative strategies. Brought to you by Worldsource Wealth Management. Let’s dive in!
Pooja: Welcome to The Advisor Delta™! I'm your host, Pooja Wallia, Vice President of Partnerships with Wealth Services and Solutions at Worldsource Wealth Management. Here with me today are Dale Collins and Courtney Castledine, Certified Financial Planners and owners at Prosperity Planning with Worldsource Financial Management, Inc. They're joining to talk to us about succession planning. Welcome ladies.
Courtney: Thanks for having us.

Pooja: Thank you for making the time to join us today. I think this is quite the timely topic to start discussing succession planning. I know it's always been a part of your thought process and been a natural, uh, avenue that you've thought about, but the fact that you've already incorporated this into your, into your process is actually quite astonishing and ahead of the time. So keeping all those things in mind, I think a lot of our team can learn a lot from what you've done.
Our advisors in the field can also learn about succession planning from you. We're gonna love to hear about your thought process, your journey, how you got here. And I think we'll start right from the top. So how did the two of you meet?
Courtney: Oh, the year was 1991. It was dark.
Dale: Oh, oh yeah. Um, yeah, it was 1991, May 3rd and uh, she arrived. Yeah, long before I was even a financial planner.

Courtney: For clarification, I am her daughter

Pooja: In case no one picked up on that. Yes. This is a family business. Uh, so that's great. Thank you so much for that. But prosperity planning itself, how did it start? How did you start this journey, Dale?
Dale: Um, well I was working at Coast Capital Savings.
I had been there for about 10 years. I had, uh, finished up my CFP and I was just finding it more and more difficult to give clnnts the service that I wanted to as they started to really dial down the products that I was allowed to use. And so I took the leap and left the credit union. I had two young daughters and was a single mom.
And so it was really scary, but best thing I ever did.
Pooja: And what made you set up shop specifically at Prosperity Planning and going out independently? Was it just, was an existing business that you took over? Did you start from scratch?
Dale: No. No. I, uh, I was lucky. The credit union made a mistake and left me at one desk for six years.
So I had developed quite good relationships with my clients. So when I left, they actually followed me. So I left and had a little bit of a following, and then I started growing from there.
Pooja: Did you always think that the daughters or a daughter would take over the business and be a part of it? Or did that just happen organically?
Dale: No, that was never, ever sort of in my realm of thought. Um, and then, you know, as ti it was always a family business though, so as I did silly things, like delivered pumpkins to all of my clients, of course I brought both of my teenage daughters out to help me with that task. There were, there was filing to do and walls to be painted at the new office and so they were always involved in the business.
And then Courtney went away and traveled. And when she returned home, she decided this looked like something she'd be interested in doing. And lucky for me, she started her education and now here we are.
Pooja: Wonderful. And Courtney, what was it about those travels that made you come back and think, yes, this is the business I wanna go into and I wanna work with my mom?
Courtney: Originally when I went away, it was to teach. I was pretty young and got to experience Beijing, China from 2010 till 2011, coming back and you know, doing odd jobs and going to school a little bit and then spending some time in the UK. I was just ready to start a career, I think, and so, you know, I came. To my mom to see more about what she did, and initially she told me I had to go hoof it and do it somewhere else.
Courtney: And so I think that was a really big eye-opening moment for me, just to get a feel for how hard it is. Mm-hmm. To start out in this industry and in this business. And it really gave me unique insight into what she was doing for her clients that other practices and firms and career shops really weren't doing.
And so it just gave me a lot of respect for the type of business that she had built, and the admiration just kind of grew from there. So yeah, I came back not long after and said, I cannot do this unless I can do it your way. And so we just started working together from then on.
Pooja: What a great journey and what made you make Courtney go out and try different things before coming and joining the family business?
Dale: I, I also knew a lot of the statistics about family businesses and I, I wanted her, I knew she had watched me build it, but I wanted her to, I experienced something else before. She came in and, and started to take over this practice because it's good like to, to know how things were done elsewhere. I had to do my time at the credit union and, you know, not necessarily agree with some of the practices that were happening there, which is why I left and went out on my own.
So I wanted her to have some experience to, to draw on, to see how, how we're different. Because that's what we are, we're, we're very different, uh, in our practice.
Pooja: I can see that, and I can see that when we enter your office, just the, the family environment that you've created. Even with the team that you have here, you can sense it as soon as you walk in, not just with the people that are here, but even with the environment.
It seems very serene and it seems like a lot of work has gone into creating this office, this team, and this atmosphere. So when did you start taking those tangible steps to not just creating your business, but really thinking about the sustainability and the longevity of the business, what it's gonna look like for the team here, for yourselves, and then of course your clients.
Dale: When we moved to this office space specifically, I wanted it to feel like us, and so the chandelier in the front entranceway, and it just, I wanted it to feel comfortable. When people come in, they feel at ease. Money's stressful, so. If they can have a comfortable environment to hang out in and yeah, have a good cup of coffee and uh, and hear us giggling in the back, then that, I think that makes all the difference.
Courtney: Yeah, I mean, I was here when Dale had purchased the office space between travels and, you know, some of the walls were painted by myself. And her vision was always very clear, a space that she could grow into to continue her career and, and bring on potentially other advisors and just make a nice space for her clients and future clients.
Yeah, I think it was really one of those things where you were thinking forward. Even the space we're sitting in now was purchased after and was something that, just thinking about the future and, and planning for, for the growth of things.
Pooja: That's wonderful. I do love the little touches that you have here. One of the things I noticed was even the reading glasses that you have in the boardroom so that if someone's forgotten their reading glasses, it's there for them to use with the water and the, and the pens and all of that. But what I've also noticed, and what Dale was quite proud of was the technology.
So the screens and the rotating banners. Is that something that Courtney, you're accredited with and, and really starting to bring innovation into the practice from what might be considered more traditional?
Courtney: Yes, I can definitely take, um, the credit for the technology piece. Whether I like it or not, it's something that's always been on, kind of on my end of the table.
Um, and so yeah, it really started with working through our current systems and our database and I mean, I've always sort of taken a liking to the social media piece and, and letting you know, our clients and the community know what we're up to and what we're about. That started back, I think, even before I was officially part of the business.
It. Mm-hmm. You know, fun to be a cheerleader for your mom's practice and when you're out at the, you know, charity run to, to post about it. And so that's just sort of evolved into more structure for the actual business and making sure that we're being as innovative as we can and we are utilizing technology to make us more efficient so that we can grow and have more capacity with the demands that are coming to us in our industry, there's more time that needs to be spent doing things. So the more efficient we can be, the more time we can spend doing what we wanna do, which is sitting with our clients, giving advice, and yeah, the fun part of the job
Pooja: I was gonna say, and the important stuff, right?
Courtney: So Of course, yeah. Yeah.
Pooja: What are some of the lessons that you've learned along the way that you would either do again or maybe avoid someone else who's looking at building a family business like this and really starting to think about succession planning? And I'll let both of you decide. Dale, did you want to go first? Courtney, did you want to go first?
Dale: sure yeah,
Pooja: Dale. Okay
Dale: I think. Right out of the gate. Communication has to be so open and never assume that the other person knows what you're thinking. If you're, if you're thinking that they know how long this is gonna take or how much it's gonna cost, or there's just, there's so much to talk about.
So that communication piece has to be. Just wide open and, and honesty about the, the process too, and how that's gonna work. We've been through a ton, what, on this journey of the last 10 years. So we're talking marriage, death, babies, like all of it. And in that, yeah, to, to have that open communication about where we're at and what we're trying to accomplish.
Courtney: Yeah, I think I definitely agree with all of that. And just to say that having the uncomfortable conversations
Dale: mm-hmm.
Courtney: Even when you don't want to, just making space for it as well. Right. Because I feel like we do get busy and we are wearing many hats, and so when we're being. Thoughtful in setting aside that time to plan the business or to just be mother and daughter.
Just making sure that we, that we break those, those roles apart. As hard as it is, I think we're doing really well at. Um, but it did take a lot of work. So just to be mindful of that, if you're in a, in a family practice or looking to bring family. And a really good counselor helps.
Dale: We have a monthly counseling meeting where we go in and then we just have a safe place where if there's anything that's kind of on the sidelines that's personal or work-wise, it's happening. We have a safe place to talk about it, and it's been very, very helpful. Highly, highly recommended. And it's a business write off.
Pooja: Win-win. And, and you actually answered my next question, which is gonna be there is the business side of things, but how do you take into account the family dynamic and how do you make sure that you're still mother and daughter and there is that, you know, almost an imbalance of power with the, with you're Dale, you're the mom and Courtney, you're the daughter, right? But when a business, you're partners right now. So it sounds like that started to evolve. Was it almost immediately? Well, actually I'm gonna backtrack for a second, Courtney. How long have you been with the business?
Courtney: So I started back in 2016 in a full-time role. Okay. So we're, we're coming up. We're just past nine years now, so almost at the 10 year mark.
Pooja: Congratulations.
Courtney: Thank you. Thank you. And a lot has changed since then. I mean, initially coming on in an administrative role and that turned into, you know, many different things. I mean, I joke that I'm probably one of the only people in the office that can do all of the pieces. Right. But I find that's really important as well.
Courtney: Mm-hmm. To, to understand and to see the different areas that things can, can grow, and can change and can be more efficient. It's funny that you say an imbalance. 'cause we always joke that I, I boss Dale around more than
Dale: it's so true.
Courtney: She loves me.
Pooja: For those of you listening, I wish you could see Dale's expression on her face right now.
Courtney: But I think too, just being very mindful of how much we both bring to the table, right? And you know, in the transition and in the planning and taking a step back to really see where the other person is coming from. And I think the more. Time I spend reflecting on what this transition's been like for Dale, the more empathy we can have for what the other person is feeling, what they've built.
We just can collaborate a lot better and
Dale: Right. Yeah. Yeah.
Pooja: When did you start the conversation then? So 2016, you're coming up on 10 years. Was it almost immediately? Was it a few years in? When did it start? Because I'm sure there was some organic growth, but there must have been a point in time. I don't know.
Courtney went to Dale or Daley went to Courtney and said, maybe we need to start formalizing this and start having these discussions, like you said, creating a safe space to have these discussions and making the business decisions as business partners versus the mom and daughter and having a place for that.
So when did you start to formalize the process?
Courtney: So I think we joked with clients from day one that I was Dale's exit strategy. Great. But it was really important for me to finish my education and so things really started to ramp up and we got more serious about having these conversations once I finished my certified financial planning designation.
And there was babies along the way in the marriage. So yeah, I think it's really been in the last few years here that we've kind of sat down and, and, and. Lined out a plan and a map. And it's funny because I waited so long, it feels like, and I was so eager, and then it's in front of you and you realize, you know, just how grateful you are for all of the time that you had before and how quickly it comes up, right?
So I think it's, it's definitely going quickly now.

Pooja: I bet. Dale, any thoughts to add to that?

Dale: Yeah, I, I feel like she really wanted it and, but there was lots happening. Like you. And I wanted her to have that time to have a maternity leave and to, to do those things. And, and I will always be there to backfill if she wants to go to the track, meet at the school.
Things that I had to miss out on 'cause I was working at the credit union. I just couldn't up and leave and go and do those things. So it's, um, it's, it's really, it's a neat spot to be in, I think. 'cause I mean, first and foremost, I'm her mom. I want her to be successful and I want her to enjoy this. Yeah, I'm just, I'm feel very, very, very lucky that I have someone that I totally, completely trust to take over something that I've worked so hard to build.
Pooja: That's great. And you actually hit upon a word that I was thinking about during your answer, Courtney. Uh, Dale, you just said the word trust and how have you established the trust that you need with your clients? Because a lot of your clients might see you as. Courtney the baby, Courtney, the toddler, Courtney, the teenager, handing out pumpkins as they go around, you know, every Halloween, uh, versus the certified financial planner who's now making my retirement plans that I have to trust.
And also as someone who's gonna take over the business, has this been a good way to establish trust? Is there some naysayers, perhaps some clients saying, I'm not sure. You know, Courtney's very young.
Courtney: I don't wanna speak for our clients.
Pooja: Right.
Courtney: But from our understanding, it's been, I would say, almost completely positive. I think a lot of that is time and you know that organic. Learning, bio osmosis being in meetings together over years. Um, I've been a part of the conversation for long enough that I think we've organically established that trust. It's not just, Hey, I'm Courtney. You're a new financial planner, and Dale's out the door.
We've, you know, they've had a, a two for one special for a number of years now. So I, I feel like I'm very connected with our, with our clients and yeah, that's been. Just the time piece. I feel like
But I would say, I've been a part of the conversation for long enough that I think we've established learning by osmosis, over years. It's not just, ‘Hey, I'm Courtney. You're a new financial planner’, you know, they've had a, a two for one special for a number of years now. So I feel like I'm very connected with our clients and that's just the time piece.

Pooja: That's wonderful. And was it, was it an active decision to start doing joint meetings? Did it happen naturally or was it as of the state, all meetings will be together?
Dale: Yeah, I think we, We definitely decided that she had to be in on the meetings. Because she had to get the background on these clients. And, um, because there's so much of what I know after 25 years of working with these people, of course that's in my head, it's not written down anywhere. So for her to get that information, she had to be in those meetings and then for her to speak up and add to the conversations and, and, you know. Acknowledged, and I would acknowledge that she was valuable in that conversation. She had things that I'd maybe forgotten about or things that I just had Yeah, just hadn't thought of. So it was, it was, um, it's been a, a long time of her being in the meeting, so they're very, they're very comfortable. I haven't had one single client push back and say, I'm not comfortable with this.
Courtney: And I think I'll just add to that. I mean, we're talking about people's financial plans, about their retirement, about their life savings. These are things that are going to continue on for a long time. Right. So seeing your planning practice doing, planning for their own practice, I think just speaks to the level of care that we have for them.
It's not an overnight transition. We want everyone to feel like we both know their story and what their preferences are and what their needs and requirements are in their financial planning journey, and so that's taken time, but I think it's been a really big value add for our clients.
Pooja: I love the way you phrased that. That was great because it is all about planning and sustainability and making sure everyone's taken care of. So I love the way you phrased that. Now, one of the things I always wonder about are the external people that help with a successful succession plan. Are there tax considerations? Are there legal documents?
You mentioned a therapist. I think that's amazing. Everyone should jot that one down first. What are some of those, you know, external experts that you need to bring in to start a succession plan or finish a succession plan?
Courtney: I think that was an area that we had a, a hard time. Getting guidance on initially. Because every practice is set up so differently. We've leaned heavily on, you know, our accounting firm, our lawyers, um, just making sure that we've got documentation and things set up correctly. So having those conversations ahead of time. Because. It can take years to get things set up correctly depending on your structure.
Dale: Yeah, and **we reached out to several other advisors, a couple from Worlds Source and asked how they had structured their transitions. Everybody's different though** and our structure is a little bit complicated in that we have a family trust and now we both have holding companies and so there's a lot of moving parts. So, um, having a really good accountant makes a world of difference and he is so kind and draws it out for us on these large pieces of paper or how this transaction's gonna happen.
And I have to admit, like he is showed us twice and every time I walk away with that. Piece of paper. I go, well, yeah, it's a lot of moving parts. So definitely you wanna reach out and get that guidance as well. 'cause you don't wanna make an error.
Pooja: So we were talking about external factors earlier, and one of the things you mentioned was a therapist and having a therapist on deck that helped you through this whole process, which I thought was wonderful. Are there any other external experts that you've used through this process to get you started through and towards the final stages? Whatever that looks like.
Courtney: Yes, absolutely. I would recommend that everyone reaches out to, you know, their accountant. We've had our accountant and our lawyers that have helped us, and the process is an instant.
It does take time and it's so unique. You know, every practice is different. We've, you know, had help from obviously our, our counselor. In mapping things out and, you know, reached out to World Source for Transitions. But it's hard to get a definitive, there are always a lot of unknowns and a lot of, you know mm-hmm.
Logistics that go into these transitions. And much like our client's planning, it's always gonna be different and it's going to be individual. So I think reaching out early, because some of these things can take a lot of time. If you have, you know, corporations and trusts involved, it can take a while to get things set up and to understand the structure. So.
Dale: Yeah, and we definitely, We reached out to several other advisors, a couple from Worlds Source and asked like how they had had structured their transitions. Everybody's different though, so you kind of have to, we definitely had to build our own, and the accountant was, was key in, in helping us figure out how.
Courtney was gonna buy the shares and how that was all gonna work out. The problem being two is our practice has grown so much that it, for her, she felt like she was chasing this thing that was never gonna be, it was, she was never gonna be able to catch up because it kept growing so much. So. Mm-hmm. Yeah.
Pooja: That's great. And so, just so I understand, clearly you're both volunteering your time for any other advisors that might be looking for some advice on starting their succession planning.
Dale: Oh, absolutely. Yeah. We would, we would chat with someone who's, who's starting out and, and tell them, you know, maybe some of the things that we would've done differently and yeah, and, and just encourage them along the way.
Pooja: That's wonderful. So those of you who are listening to this, you heard it here first, Dale and Courtney are here to help. What would you have done differently if you look back at the last 10 years almost? Is there anything that you would've done differently? Courtney?
Courtney: Honestly, I think where we're sitting today, I mean. I could continue on in a partnership like this for many years to come. I think we both bring, you know, so much to the table and I have a lot of fun in this role. Working alongside Dale slash Mom, I think setting expectations and milestones. Possibly earlier and just having those conversations to ensure that everyone understands how long these things can take.
I like most successors, was more eager than maybe I should have been at the onset. And you know, as I've grown into the role and understand the practice and understand how, how, how big it is, I understand how much of a commitment it is to do it by yourself. And so now I think I'm on the other side of. You know, thinking about my own successor because it is, it's a beautiful thing and I love doing it together.
So, yeah, I think it's just the time and being, giving yourself grace to, to have those conversations.
I think setting expectations and milestones possibly earlier and just having those conversations to ensure that everyone understands how long these things can take. I like most successors, was more eager than maybe I should have been at the onset and you know, as I've grown into the role and understand the practice and understand how big it is, I understand how much of a commitment it is to do it by yourself.

Pooja: Right. What about you, Dale?
Dale: Yeah, I think definitely having, having something perhaps written down or just having some timelines because there was a a point where there was definitely some frustration.
Courtney was like, this five year plan is like seven years in, dude. Like, let's get this done. Everything happens when it's supposed to and, and now we've got a, it's all documented. We know how the, the financial piece is gonna go. So yeah. But I think giving her some. Lines in the sand, I guess would've been helpful. 'cause then she wasn't just wondering when, when, when, when.
Courtney: And I don't think that's unique to us. I think that a lot of succession plans, family or not definitely have those dynamics. And I think when I started to think from Dale's perspective of what this transition was like for her and to have those conversations and to kind of dig into those feelings around.
You know, kind of giving up a piece of yourself that we started to see more clearly and more eye to eye and. To any other, you know, younger advisors who are in this position utilize the time. It is amazing time that you can't get back and, you know, taking every opportunity to get to know more about the client base and about this practice and, you know, understanding everyone on a deeper level that you're working with or working for.
It's, it's mentorship, right? So I, I think, you know, looking back. I wouldn't change things.
Pooja: Right.
Courtney: I would maybe just have communicated them clearer

Pooja: and some things are definitely in hindsight. 2020. I understand that. If you could sum up in one sentence, maybe two, what this process has been like and to encourage other advisors to start their succession planning, Dale, what would you say to them?
Dale: Oh, I would say yeah, if you can find that person and start working with them and get them involved in your practice and really get to them to understand what it's about, like what you've created, because everyone does things differently and, and it takes a long time for people to earn trust. So the more time you have to get out in front of this, the, the better.
I just feel so, so, so lucky that I have someone that again, I can totally trust to take care of my clients when I'm not here doing this anymore.
Courtney: I think instead of thinking about it as your retirement or you're, you're leaving the industry to, it's an opportunity. I mean, I feel like our practice has grown, quadrupled, and a big piece of that is the fact that we're here and we have a plan, and if your job is planning for the future.
As a, an advisor, it just makes sense to plan for your own future and for your client's future and who's gonna take care of them if you are not around to do it. So, yeah, I think it's, it's a pretty special thing and be ready to evolve. I mean, we've changed so much in 10 years, you know, the practice has changed, the industry has changed.
And
Pooja: just a little, just a bit.
Courtney: And we've had a lot of fun. I mean, I feel like we're in a place now where-
Dale: Yeah, it's not uncommon for me to walk into the office and someone will, one of my clients will look up and go, oh, you're still here as it should be.
Pooja: So ladies, one thing I want to touch upon is you've mentioned a couple of times the growth that you've seen, especially not just your own growth within the business, but now there's two of you and as a family business and as you're doing this planning and growing, are there new types of clients that you're attracting to the business because it is also a family business?
Dale: Absolutely. We've, um. Yeah, we've been really, really successful in attracting business owners that are in a similar position to us, and they're looking to us seeing that we're doing it and they are looking to us for guidance as to how they hand off their business, and not necessarily just to children, but to, you know, maybe, uh, a key person or, but that has been a huge part of growth for us.
These business owners have accumulated a ton of wealth and we're able to help them transition that either to the next generation or off to the new owners.
Pooja: How interesting. And how do you handle that type of growth and that different dynamic?
Courtney: I'll say, this one? Yeah. I, um, honestly, we did have to hit a point where we, you know, did a bit more thought into what is the right fit for us, and we had to, you know, put processes in place to make sure that, you know, not only were we attracting the right client clients, but that we were giving, you know, everyone that reaches out some advice and, and some of our time, but not necessarily taking everyone on anymore. Um, sustainability of our practice is a, is a big thought for me, especially just seeing the trajectory and seeing the growth in the 10 years I've been here, um, and knowing that, you know, eventually one day Dale will retire and it's, you know.
Courtney: Potentially going to be all on me. So just making sure that we are thoughtful in our process of what is the right fit and how do we do that in a way that people are gonna find value, even if they don't necessarily become a client.
Pooja: I cannot thank the both of you enough for making the time to sit and talk with us today. It's, it's lovely to see the two of you, but also to discuss something that these days seems to be an avoided topic. No one's talking about it enough. And to see two people do it so successfully and to have your viewpoint, especially with the family dynamic, that's always what I'm curious about.
It's been spectacular and I hope our listeners enjoyed this as well, and we look forward to talking to you again soon.
Dale and Courtney: Thank you. Thanks so much.
Narrator: Thanks for tuning into The Advisor Delta™! We hope you found today’s episode valuable to supporting your practice. For more episodes and insights, don’t forget to subscribe and visit us at www.worldsourcewealth.com. And remember, together, we can take your practice to the NextLevel™. Until next time!
Worldsource Financial Management Inc. (a mutual fund dealer) and Worldsource Securities Inc. (an investment dealer), are divisions of Worldsource Group of Companies Inc., operating as Worldsource Wealth Management. The views and opinions expressed in this podcast are those of the participants only. This podcast is for informational purposes only and does not constitute financial, legal, or professional advice. Listeners are encouraged to seek professional guidance for their specific needs. Worldsource Wealth Management does not endorse any products, services, or companies mentioned in this episode.