If I Had to Launch My Planning Career Again, This Is Where I’d Start

Every young advisor eventually asks the same question:

Where should I start?

Broker dealer or RIA?
Big firm or small firm?
Join something established or build something from scratch?

In this episode, James answers a listener question that goes deeper than structure. It’s not just about whether RIAs are “better” than broker dealers. It’s about something far more practical: where will you get the reps, the mentorship, and the growth opportunities that actually shape you into a great advisor? 

Drawing from his own early career — starting in operations, moving into paraplanning, and slowly earning the opportunity to lead meetings — James breaks down what truly accelerated his development. It wasn’t designations alone. It wasn’t the “perfect” firm structure. It was reps. Conversations. Real clients. Real objections. Real responsibility.

He also addresses a second critical question: how firms like Root can onboard clients confidently before delivering a full plan. The answer lies in a powerful progression: Do → Show → Tell. When you’re new, you demonstrate value by doing the work upfront. As credibility builds, you show proof. And eventually, brand trust allows you to tell clients what to expect with confidence.

If you’re early in your advisory career — or mentoring someone who is — this episode provides clarity on how to choose the right environment, how to think long-term, and how to grow into the advisor you actually want to become.

This isn’t about finding the perfect firm.

It’s about finding the right place to grow. 

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The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

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Transcript

Listener Question From Justin

SPEAKER_00 0:00

Hi, and welcome back to another episode of the Root Ready Podcast. I'm your host, James Cannol. Today we are answering a listener question, and this question comes from Justin. Justin says the following Hi James, first and foremost, I'm only five episodes in and I've absolutely loved all the content I've consumed so far. I think this is exactly what I've been missing in my career. I do have some questions I think would be relevant for the podcast. The big one, I think that all the content you put out is great and aligns with the values I hold, but a lot of broker dealers and RIAs don't hold such values. Where do you recommend starting out yet? Can you run a practice like this at a large broker dealer, or is root the only one of its kind? Do you recommend just starting your own RIA because it'd be better than a broker dealer? What I'm asking is, do you think it's worth it to start anywhere, just to start in the industry, and make it better over time if you have limited options? Or do you think there's a better way? I know root seems to be the best way in my mind, but beyond root, what do you recommend for young advisors who are hungry to do the right thing for clients? In the Sequoia system, I noticed assets transfer after the kickoff meeting and before the planning meetings. How do you get clients to trust you without showing them their plan? Is it brand recognition? If that's the case, one, kudos to you for doing so. And two, how does someone else replicate that? Justin, thank you for the question. By the way, some of you maybe saw Justin on LinkedIn posted a very cool recap of a lot of the uh Root Ready episodes that have been posted. So check that out if you've not already seen it. But the question here, I'm gonna distill down into two different parts. Number one is what's the best way to get your start in this industry? How do you find the type of firm that will support the growth that you're looking to have to become the type of advisor that you want to become? And then number two is more specific to Root Sequoia system. It's our process for onboarding new clients and making sure that we're building that comprehensive plan for them in a very standardized way that allows us to really personalize the experience for the clients. So, first, I'm going to address how do you get your start? So I think I'm very biased here, but I would like to think that this is the case. Root's going to be one of the best places. A lot of people can come and be able to get the type of the support they need to be an Osm advisor. Between the support we offer from our structure, our developments, our trainings, having ahead of planning, ahead of investments, ahead of advisor coaching, all designed to support the growth of our advisors. Yes, I think that root is going to be the best place to do this. However, I'm going to give guidance here that has nothing to do with root. And there's many different ways that you could enter this industry and have a lot of success in this industry. I'm not going to pretend to know all of those ways or to say that one path is the exact best path for every single person listening. But what I can do is address Justin's questions through the lens of my own personal experience in this industry. When I started in this industry, I was 21 years old when I started as an intern. And I interned both for an independent wealth management firm as well as for Merrill Lynch. Hated my Merrill Lynch internship, really liked my internship with the independent firm. So when I graduated college, so I did college and then stayed for business school, I was 22 years old and I started in this industry with the independent firm. So not the Merrill Lynch, not a big bank. But here's the thing: the independent firm that I started with, independent is kind of relative. Everyone kind of calls themselves independent in the same way, if you'll notice, everyone kind of says they're a fiduciary. So sometimes these words don't really mean uh what you think they might mean or what I think they might mean. But this firm that I was with was associated with a broker dealer. So there was an RIA component of it, but it was the broker dealer's RIA. Here's what was beneficial to me, though, about that. I had no idea what a broker dealer was versus what an RIA was when I started in this industry. All I knew is I'm working here at this firm and there's people that are coming to us looking for guidance about what to do with their money. So I didn't know, nor do I really, I guess, care. Maybe I should have cared, or maybe I would have cared in retrospect if I knew that much of a difference. But in some regards, I'm glad I didn't know some of this. I wasn't focused on the right structure, the right firm, or the right whatever. I was just focused on saying, here's clients coming to us. They're looking for help. How can I best help? So that's where I started. But on top of that, I did not start as an advisor. So when I started with the firm I started with, it was a very, very small firm, a tiny firm. I think that AUM was maybe in the single digits, somewhere between the five to$10 million mark when I started. It was one single advisor. That advisor was a firefighter. So his full-time job was being a firefighter, but he had two days fully on at the station or three days fully on at the station, which meant that he needed someone back at the office to be able to, quite frankly, just do receptionist duties, to do operations duties, to do client service duties. So that's exactly what I started as. It was not as an advisor. So yes, I had finished my degree. I had graduated from business school with a concentration in finance, but I had no idea how to be an advisor. I didn't know anything about the CFP curriculum yet. I didn't know anything, most importantly, about how to lead a meeting or how to have that confidence to be able to guide an actual client to what they wanted to accomplish. So I started out very much just doing paperwork, doing operations, doing receptionist type duties, kind of holding down the office as an office manager of types. And after a year or two of doing that, then I started doing some paraplanner type duties, some associate advisor type duties. Then after one or two years of doing that, I started doing some advisor type duties. And one of the things that was unique about the firm that I was with is we were part of what was called at the time the Dave Ramsey Endorsed Local Provider Program. Now it's called Dave Ramsey Smart Vester. So many of you have probably heard the name Dave Ramsey. Dave Ramsey has this program where if you pay to be part of a system and if you align with some of the values that he has or some of the philosophies that he has, you can be part of his network. And to be part of his network means you pay a monthly fee. And in exchange for that, you get leads that reach out to Dave Ramsey saying, I live in this zip code and I'm looking for help with financial advising. Dave Ramsey's team gets that, and those leads get routed to you. Now, we maybe had 40, 50, 60 leads a month coming in. So to me, again, who cares if I was in a broker dealer setting? Who cares if I was in an RIA setting? And I shouldn't say who cares. Yes, it matters. I had no idea the history of the two. I had no idea what the two even meant. I just knew I'm working at this firm, and this firm isn't called broker dealer, it's not called registered investment advisor, it's called Seaside Wealth Management. I don't actually know what's happening on the back end, but I do know there's 50 people reaching out each month. And now for a while, my boss was taking all those, but then it got to the point that there's a lot, or I would start taking some of them just to help out with some of this. And here was the most important thing for me. I got a huge amount of reps in doing that. A large number of phone calls, just calling people, asking questions, understanding how we might be able to help. And that was probably the single best thing that was helpful for me. So, Justin, I'm gonna circle back and answer your question in a more direct way, but I'm gonna, again, just paint a little bit more of a picture of my experience in this industry so I can see what was helpful to me and what might be helpful for younger advisors just starting to enter into this industry. So, going back to my experience, the actual first bit of experience I had as an advisor didn't come for maybe three years into this. I forget the exact timeline, maybe two years into this at the fastest. But I started making some of these calls. I started having some of these conversations. I remember my first actual meeting with a client. My boss was coming from the fire station because, again, he was a firefighter when I started working with him. And he was gonna come down and I think he had a meeting at, I don't know, let's call it 10 a.m. But he didn't get off his shift until 8 a.m. And he worked about an hour away from the office. Something happened and he wasn't gonna make it down in time. He, I don't know if he had to stay longer to shift. I don't know if he got caught in traffic. I don't remember exactly, but I remember getting a phone call saying, hey, James, this client's coming at 10 a.m. And my immediate thought was cool, I'll call them and have them reschedule. But my boss said, no, you're gonna take that meeting. And I was so grateful that happened. I remember being terrified walking into that meeting, but I'm so grateful that happened because I'd been making some of these calls, I've been doing a lot of the pair planning work, I've been sitting in on a lot of meetings, but this was my first chance to be an actual advisor, to actually sit across from somebody and guide that meeting. They came in and I was as nervous as I could possibly be, but that meeting went fine. And then I took another one and another one and another one. And so it was this progression of starting out doing paperwork and ops and reception and office management duties to doing some paraplanning and back end work to doing some advising. And I had a very called organic growth rate through that. And I'm very grateful that my boss at the time was pushing me to do more and more. And so I didn't have a formal sales program. Now, newsflash, most RIAs don't. Most RIAs are very small firms that don't have anything in way of a formalized training program. The ones that do have formalized training, it tends to be more like sales training. It tends to be more something that wouldn't necessarily be the technical training that most young advisors are looking for. It's just how do you talk to clients? How do you do that? But this was super, super helpful for me. Because here's the reality of it. As advisors, we think training means how do I get all the technical skills, the investment skills, the planning skills? And yes, we need to get those. But I remember when I started taking calls. Hey, Mr. Prospect, this is James Cannole, call from Seaside Wealth Management. Uh, it's all you reached out. How can we help? And their thing is, well, I got a 401k. What do I do with it? Simple enough question, but I remember being on the other side of that saying, God, geez, do I answer his question? Do I ask more questions? Do I try to sell them on our service? Do I what do you actually do in those situations? So having those calls, having those reps allowed me to master the non-technical piece of this industry. And I think that non-technical piece, how to run a meeting, how to ask questions, when to ask another question versus when to pause and let the client think and let the client speak, how to overcome objections, how to deal with the emotions that so often show up, that always show up, I should probably say, when people talk about money. So having this steady stream of calls allowed me to do all that. Plus, there's another real benefit of this that in retrospect was huge for me. I'll sometimes read these studies and say, how long does it take to build a comprehensive financial plan? And advisors will say 35 hours, 40 hours, 50 hours. And part of me thinks, what the heck are you building? What on earth are you building that's taking 50 hours to put in front of your client? And sure, maybe there's the occasional highly complex case, or you do super sophisticated planning where all that work is required and it's required up front. But oftentimes I get this sense that people are doing all that work, advisors are doing all that work because they don't have the ability to help that client prioritize what to work on first. You can't focus on a million different things at once. So, yes, there might be a huge amount of stuff to do for a client, but can we start by going through the proper order of operations here? Can we start by understanding what's the biggest priority they need to focus on? Because if I'm trying to get my client to do a hundred different things at once, that's incredibly overwhelming for anybody to do. If someone came to me and gave me a ton of action items from all this stuff, I'm probably not going to do any of them. But if instead I've understood, I've worked with enough people to say, okay, here's everything going on. I can see this, but I also can clearly see this over here, this is a priority. This is red flag. We need to get this addressed right now. This other stuff is important, but I don't want to take away any time or attention from getting this one thing doubt in right now. So oftentimes the reason people are spending so long is maybe they didn't have all the reps. Maybe they've only worked with a handful of people in their career. And when you've only done that, you don't have the context to be able to say, what should we prioritize? What should we focus on first? What can be done in six months and 12 months and 18 months because it's not a huge priority. But what can we focus on? Because knowing human behavior to be what it is, we're only going to be able to focus on one thing at a time. So let's knock this out, then go to the next thing. Knock that out, then go to the next thing. And so that was a hugely beneficial thing for me to get all these reps and to be able to have a conversation and quickly get to the heart of the matter of what's the actual challenge this person is facing. Not just have them come to me and say, hey, I'm a little bit overwhelmed about my finances and say, great, I'm gonna take you through a full cash flow analysis, a full insurance analysis, a full state plan analysis, a full 401k review. Oh my goodness, you're gonna, they're gonna be a deer in the headlights. And so if instead you can learn to have those conversations, learn to ask the right questions, learn to pause, what you're trying to do is get to the heart of the matter. So all this to say, circling back to Justin's question, the huge benefit to me of this environment was reps. The reps, the conversations, talking to real people about real challenges, not just learning about financial planning and textbooks, not just reading the CFP curriculum, but having an opportunity to talk to real people and understand how to run a meeting. And here's why this is important. The analogy that I think of in my mind, because this I've had this experience, is have you ever been to a doctor or a dentist or somebody like that, where you've seen all the diplomas plastered all over their wall, but they come into the room and start talking to you and you just they you're just not communicating. They just don't know how to have that normal conversation. They don't know how to ask you questions and make you feel heard. They don't have that bedside manner that makes you feel confident in the advice they're ultimately delivering. Don't be like that doctor or that dentist. If you spend so much time getting designations, learning the technical side of this, you've mastered everything. But you can't have that conversation with the client. You can't be a human that's connecting with someone else. You're gonna be like I was when that doctor's telling me something that I know he's smart, I know he's got all the designations and the degrees. I just don't trust that he actually knows me. He doesn't actually fully understand the problem I'm coming to him with. He's relying on his smarts just to make assumptions about what's wrong with me. Now here's the thing his diagnosis was maybe perfectly accurate, but it didn't help me feel confident in what he was saying. So when you have an environment like I had, where, by the way, I was learning the technical side as well. So I wasn't just jumping into client meetings, getting on reps without any idea of what I was doing. I spent a couple years, like I said, just doing operations, just doing behind-the-scenes stuff, then starting to sit in on client meetings while I'm taking my CFP stuff. So there was this good balance of learning and doing, learning and doing. You will never do by learning, but you will learn by doing. That comes directly from Nick Murray. If you don't already, by the way, read Nick Murray's newsletters, read all of his books, probably one of the most impactful people, at least on my personal career, and then know the career of a lot of other advisors as well. So, Nick Murray, read all his stuff. But this balance of learning and doing was great. So if I was to summarize my feedback to this first part of Justin's question, here are the first few things I'd look for. Number one, I would look for a place where I could optimize for reps. To me, yes, ideally that's in an RIA environment. You might not have the opportunity or the luxury to do that. If you're operating in a broker dealer environment, that doesn't automatically mean you are a bad person. I know many, many people in a broker dealer environment that are wonderful people, providing great advice. So it's not conflate the fact that RIA is pure good and broker dealer is pure evil. Yes, RIAs, there is less of a conflict to do something that's not in the client's best interest. There is a higher legal standard that you are held to, but I know plenty of people in broker dealer environments where they're very good people, very good advisors. So if that's all you have, still do that. I'd much rather work in a broker dealer environment where I could get reps and do playing the right way with well-intentioned people than work in an RIA where there's not well-intentioned people. There's not the ability to get reps, there's not anything that's going to allow me to develop as an advisor. Number two, prioritize working at a place where you're going to get some level of mentorship. Make sure that you're not trying to learn everything from scratch. Now, my hope is this podcast can be some level of mentorship for you. My hope is the other resources, whether it's Nick Murray, whether it's Carl Richards' writings, whether it's Michael Kitzis' writings, there are now many places where, yes, an actual one-to-one mentorship opportunity is incredibly helpful. But between podcasts, between books, between resources, you have a lot more access to resources today than you did a couple decades ago. Take advantage of that. Let this podcast be part of that. Let Michael Kitz's information be part of that. Let Nick Murray, let Carl Richards, whoever it is, there's so much great content out there. Make that part of your mentorship. But if you're at a firm where you can get reps by not just doing them yourself, but by observing someone else, by having someone you can go to with questions, that can be a really strong place to start as well. By the way, quick side note here, I may or may not have released this already by the time this episode is aired, but fully intend on doing probably a bi-monthly, so once every other month, ask me anything type office hours, where I'm going to just hold an open Zoom session. The goal is for this to be for growth-minded, younger advisors who are trying to make their way in this industry, where it's just an ask me anything. Come with your questions. I'll provide whatever feedback and guidance I can. So make sure we're connected or you follow me on LinkedIn where I'll be announcing that. It may already have been announced, depending upon the timing when that happens and when this episode actually gets released. But try to prioritize a place where you're gonna have some level of mentorship, especially in those early years. Now, number three, and in some ways this could contradict number two, but I don't think it actually does. Number three is document what doesn't work about the firm that you're in. Now, I remember my firm and where I worked, and there's a lot of opportunity for me, a huge amount of reps, mentorship, the ability to get guidance from someone when I needed guidance, but I also noticed things that I wouldn't do if I were to ever join another firm or start a firm, which by the way was zero part of my intention while I was there. But I do remember thinking, ah, this probably isn't the best way to do stuff, or this isn't really something that I feel super connected with, whatever that might be. So if you're in a firm like that, or if you're in any firm, there's always opportunities to improve. Document those, write those things down. What would you do differently so that the next firm that you join, you're not joining another place where it's still making those same mistakes or still doing something the way you don't think they should be done if you're gonna make that transition. But all that to say, if I could summarize all this, this is an incredibly amazing career. And hopefully, for those of you who are newer to the career, you can do this for 30 to 40 years. So I would say that don't optimize to try to make year one the best or year two the best or year three the best. Don't feel like you have to be in the final destination of where you're gonna spend your entire career, right out of college or right in the industry. Optimize for a place you're gonna get reps, optimize for a place you're gonna get mentorship, and then optimize, and this is regardless of where you go, making sure that you're understanding what you would do better, what could be done better, so that when you find your next opportunity, that next place can fully align with the way you think things should be done. So that's part one of Justin's question. I'm gonna answer part two uh much quicker here. But Justin asks in the Sequoia system, assets transfer in after the kickoff meeting and before the planning meetings, how do clients trust you without seeing the full plan? Is it brand recognition and how can someone replicate that? The short answer is yes. Brand recognition absolutely matters here. I don't remember where I first heard this. I think it was probably Angie Herbert's and Co. Either something she wrote or something that her firm put out. But there's this concept of do, show, tell. Meaning when you're a much smaller RA, let's assume that you launched something today. Nobody knows who you are, who your firm is. There's no proof of anything that you've done. You are the brand. Every company has a brand, but for most companies, that brand is just the personal brand of the person who's leading it or the person who started it. Now, that personal brand may be great or it may not be, but when you're first starting, everything that someone's gonna believe about your firm is what they believe about you. So you don't have the opportunity to say, hey, look at this massive amount of work that I've done for clients. That's the brand, that's what you can trust. But when you first launch and you first get going, you're not gonna have this massive brand behind you, not even this massive personal brand behind you. So what do you do? You can't just show them what you've done. You can't even just tell them what you've done. You need to do it. So if a prospect comes to you, this is why most advisors, they do some of the planning work up front. Either they charge for it or don't charge for it. But what you're doing is you're demonstrating what they can expect to get from you. A few years ago, this is exactly what I was doing. I was giving away. Now you could have made the argument, I should have charge for it, fine. Whether you charge for it or don't, I was giving away a little bit of the planning work first, giving the client or giving the perspective of the client the opportunity to see what that work would look like, what it would feel like before they made that major decision to say, okay, let's work together on an ongoing basis. As you start growing, you can now shift to that show type framework. I don't have to do all the work for you, but I can show you. I can say, okay, this is the situation you're in. This is kind of where your challenges are your pain points. Let me show you a sample plan. Let me show you a sample portfolio. Let me show you a sample whatever, a sample deliverable that can show that prospective client what it might be like to work with your firm, even if that plan isn't done specifically for them. Then as you continue to get bigger, what you can do is you can start to shift to more of a tell framework. You've got enough evidence built up. You have this corpus of work that's built up, either signaled by how large your firm is, by the AUM of your firm, by the number of clients served by your firm, by the marketing material you put out about your firm. All of those things are signals about what people can expect when they work with you. So, yes, now when clients work with us, they are transferring over money, they are becoming clients before that planning work is actually done. And it's because of the tell process. We can say, this is what you're going to receive, this is what our Sequoia system is. And it's a much easier part of the sales process. Because of obviously the brand that Root now has. Now, there's still a huge element of show here. If you look at our YouTube channels, look at our social media, there's a huge amount of work that we've put out there. So it's shown prospective clients what they're going to get when they work with us. All that makes it easier for people to move forward in that sales process without needing to say we need to go through every part of the planning framework before I'm going to commit to something on a go-forward basis. So new advisors don't expect that's going to be the case for you. That was not the case for me. That shouldn't be the case for anybody. You have to kind of go through that framework of the do, the show, the tell, at least directionally to make sure that you are meeting your prospective clients where they are and their perception of what you can or can't offer based upon what they know to be true about where you are. So that's the answer to the second part of your question there, Justin. Hope that's helpful. So that is it for today's episode as we address that. If you are watching, if you have a question, you can go to the rootreadypodcast.com and you can submit your question that I will answer on a future episode. If this podcast has been helpful, please share it with another advisor that you know is looking to be the best that they can. Please leave a review if this has been in any way helpful to you. I want to make sure this is a growing resource that can help more and more people on their journey to be the best possible advisors they can. Thanks for listening, and I'll see you next time.