The Achieve Podcast - Kimberley Raimondo (Brookwood Investment Group)

In this episode of the Achieve Podcast, host Taylor Baker interviews Kimberley (Kim) Raimondo, CEO and founder of Brookwood Investment Group. Raimondo shares her journey from litigator to financial‑services entrepreneur, describing how she and her husband built Brookwood from a partnership into a firm that now supports over 75 advisors and 25 staff members. She attributes the firm’s 400% growth and 99% client and advisor retention to a people‑first "human alpha" philosophy that removes busy‑work and focuses on meaningful relationships. Raimondo introduces the concept of "coopetition," positioning Brookwood as a collaborative ecosystem that breaks industry silos and incubates ideas like a venture‑capital model. She discusses the industry’s shift toward consolidation and an integration model where Brookwood takes equity stakes in advisors to ensure continuity and succession. AI is a core strategic pillar: three in‑house technologists and external consultants develop automation, smart‑alpha portfolios, and data‑driven decision‑making, freeing staff for higher‑value work. The conversation covers Brookwood’s target advisors (entrepreneurial, legacy‑focused) and clients (complex needs, seeking stewardship), current growth opportunities in AI‑related investments, and future priorities such as expanding talent, increasing outreach, and deepening partnerships. Raimondo reflects on lessons learned, emphasizing the importance of appreciating successes, failing forward, and continuous evolution. Listeners are directed to Brookwood’s website and LinkedIn for further engagement.
Chapters
Welcome to another episode of the Achieve Podcast, the show where we highlight leaders, creators, and entrepreneurs, those who are building meaningful businesses, shaping their industries, and having an impact. I'm Taylor Baker Baker, your host, and excited today to be joined by Kim Raimondo, the CEO and founder of Brookwood Investment Group, and you can find them at brookwoodinvestmentgroup.com. First off, Kim, thank you for joining us today.
You're welcome. Thank you for having me. I'm excited to be here.
I am too. And so for those getting to know you, if you wouldn't mind, give us the backstory a little bit on how you got into this space and who you're currently serving, because it's a little bit of a niche.
Sure. Yeah. I was a litigator for many, many years, and then I was working as an attorney and my husband was working as an attorney and he went into the financial services space. So, in 2000, he joined the financial services space. And for the next decade or so, I watched him as he maneuvered through that space. And I thought, you know, I think I could do this differently. I think we might be able to do this in a way that I felt was a better mousetrap. And so, really, that's why I got into it. So, in 2010, we joined forces and I got into the business to help grow. To support his business originally, and then it grew into this. We realized pretty early on we had a real passion for helping advisors, and we had— we knew something about the experience because we had crafted one for him. And so we, we took what we learned along the way and we turned it into Brookwood.
That's awesome. And how big is the team organization now?
Oh gosh, so it's grown to, um, we have over 75 advisors nationwide and we have 25 people on staff. Wow. Wow.
That's impressive. So looking back for you, what would you say, what turning points have molded the way you think about running the organization?
Well, so much has changed during the time that we've been working in this business, right? I mean, in 2010, when we got started in the business, we founded Brookwood in 2021, but we had a prior partnership. So we've been in the business a lot longer than Brookwood has. But when we first got in the business, you know, it was a very different business. So 2020, I think, changed everything for everybody. And, you know, I really think that was a turning point for everybody. And so between that and what's happening on the technology side, right? I mean, we're entering into this next revolution, this evolution of, you know, the economy and of transformational change. And so things have just really accelerated and we've seen so much change in the last 6 years between, you know, remote, right? Remote offices, clients wanting to be remote, the acceleration of technology, the acceleration of AI. I mean, all of these things have really contributed to a changing atmosphere in industry. And I think just transparency in industry, wanting to have things that serve consumers better, right? Wanting more access to wealth. All of these things have really shaped and shape-shifted the way we do business. And so we're trying to be agile and respond to those things as they come at us.
Well, that's awesome. And what would you say has been driving growth for you guys mostly right now?
I think we have a very, uh, clear sense of who we are, right? We have a 400% growth rate at Brookwood, um, and we have a really high retention rate. Yeah, we have a, you know, we have a 99% retention rate both on clients and advisors. And I think a lot of that is attributed to the fact that we're a people-first organization. Regardless of what happens in the industry, we are very much a believer that the industry is a steward for clients and we are here to serve those clients in a way that's meaningful and we're here to serve our advisors in the same way. And so our ethos is really built on the idea of human alpha, right? Remove away all distraction, all the busy work, all the busy badge. You have humans. Humans are important to us. And I think at the end of the day, that's what resonates with people.
Yeah, those stats are staggering. 400% growth rate and 99% retention. That is impressive. So what would you say has been some of the key, the key secrets or, or components of, of attracting and retaining those kind of numbers?
I think, again, I really think it goes back to creating deep, strong foundations and relationships. At the end of the day, both on the client— excuse me, on the client-facing side and on the advisor side, we are very cognizant of never wanting to be transactional. This is not a transactional business. This is a relational business. And so for us, we spend time and effort getting to know the people who work with us and the people who we serve. And so the advisors that we attract are very much the same with their clients. So it's an advisor-centric, client-centric experience, and we treat everyone as we would want to be treated, right? It's a very simple rule. But, you know, at the end of the day, we want to feel meaningful and we want to feel purposeful and we want to feel connected to other people. And that's what most people want. And if you create an environment where people feel that and feel supported in their business, then I think that really helps to retain and attract talent. And, you know, my, my thought is also, you know, all of these advisors who join us, most of them are either solopreneurs or they've been part of a large organization. Both of those has its own set of challenges, right? So when you're a solopreneur, you're carrying all of the rocks in the backpack, right? Those people, those advisors have so many responsibilities. They wear so many hats. And as the business gets more complex, it just becomes more burdensome. And so our job is to take those rocks out of the backpack and allow them to be able to climb the hill a lot lighter. And that's what we do. We try to help them do that. And, you know, and then on the institutional side, I think the challenges those advisors face is that they're one of many, one of too many. And so their business becomes sort of lost in the shuffle and then they lose sight of, you know, how do they differentiate in the market? How do they become— how does their business become meaningful and impactful for themselves and their legacy? And so I think we try to solve both of those problems.
That's beautiful. I love that. And it's interesting that so many people talk about that concept, But your numbers show that you live it.
We do, we live that. I mean, we do. And I think, you know, you're only as good as your word. And I think that's the most important thing is that if you show up for people on a regular, consistent basis, people will stay. And, you know, that's the goal, right? Is to show up on a consistent basis in anything you do. And one of the other things I think that's really meaningful that we do here is we also are very much focused on the concept of coopetition. So my business leadership style is built around the framework of coopetition, and it is the antithesis of competition. So we work in an industry that's very siloed, and that silo has created competition and sort of this cutthroat idea that we can't share and collaborate and use one another to be successful. My point of view is the opposite of that. That competitors should come together to mutually benefit. And that's how you grow business. And so whether it's on the advisory side, on the strategic partner side, I'm always looking for competitors to mutually benefit. And so we get advisors together to be able to collaborate because you cannot do this business alone. Everyone grows better together. And so you cannot be responsible for knowing everything that goes on in the universe. This is not possible. You know, it's, it's, it's, it's an impossibility. To me, it's about where there's a silo, we break it down and we offer opportunity for collaboration, for partnership, for engagement. If someone has a great idea, bring it. We're not coveting great ideas. We're here to support great ideas and to be able to help them to incubate. That's, I think, also one of the things that is really interesting here is we're almost more like a venture capital group where we really incubate ideas and we support each other in the ecosystem. That we serve. So it's kind of a cool environment to be in.
Yeah, I honestly— that's a new term for me, coopetition. I, I've heard of healthy competition.
Yeah, but like, yeah, it's cooperation and competition, right? It's like we cooperate and we, you know— yeah, I love that.
That is so true. That's a good ethos to live by. So where do you still see opportunity or money on the table with this as you're building this?
Well, now, now what I think is happening in the industry as an owner-operator of a large firm, what I would say is happening is a lot of consolidation. And so with that consolidation, I think we're going to see the dissipation of the aggregator model. So where advisors used to tack on to groups for service, for compliance, for operations, for things like that used to be a tack-on service. I think now we're really leaning more into the integration model where we truly are seeking partnership with advisors. And, you know, we're taking equity in advisors to allow them two things. One is to become a true partner to the business, and two is to provide consistency. And the third thing is to provide succession and continuity because no one is immune from the need for that. And I think regardless of how Regardless of how someone feels about their business, everyone needs continuity. You know, no one should be going that alone. And I think there's a— unfortunately, I think in the market, advisors have been underserved by that, by that need. And so I think everyone is in this place where we're searching and we're going so quickly to get and adopt AI. But the real threat to the business is continuity. So I think people really need to focus on that, and I think they're afraid to make those decisions because they're big decisions to make, but it's necessary, right? And so I think we're here to sort of serve that goal and to try to help those people to get through that.
I love that. Now, you mentioned AI. There's a lot of talk around that. Where have you guys found ways internally to utilize it?
Yeah, I mean, AI is a very big initiative of ours. Um, we realize very very, uh, strongly that AI is necessary to do the business and to thrive in the business. Uh, we partner with technologists. We have 3 technologists on staff. We have consultants also who are helping to build, uh, automation and more artificial intelligence in the processes. So what we're trying to do is we're trying to cut down on the time to get work done. So one of the reasons for that not only to create efficiency, because there's a lot of talk in the market about efficiency. For me, it's about not, not just efficiency. The efficiency is a means to provide for more meaningful work. And so again, it allows us to really pursue that human alpha that we str— that we strive for. And so the more we can take off the busy badge and the task-oriented work, the more we can do purposeful work. So that's the way that I see AI becoming very useful, is allowing people to do better work and more meaningful work in their day-to-day lives and in creating more meaningful connection between the human beings that work together. So whether it's time spending more time with clients or spending more time as a group or, you know, solving higher-level problems, I think for me, AI is not a threat. It's an opportunity to basically self-actualize, to be able to do higher-level work, right? I think back to when I was younger and we used to have to remember every phone number that ever was. I don't remember any phone numbers now, right? And no one is lamenting that. It's just, it's freed me up. It's freed my brain up to do higher-level things. And I think AI is the same way. So we use it across the operations staff. We use it in our portfolio building. We've been using that for about 2 years in our portfolios. And so we use, we use technology that allows us to build what we call smart alpha portfolios. And those portfolios allow us to optimize what we feel are market conditions. And we're able to pull data very quickly through to be able to, to be able to interpret that and extrapolate out what we think makes sense on portfolios. So our CIO is very much leans heavily into that and it allows us to do that at a much higher rate of speed. Right. Because, you know, years ago you couldn't look through all the data that existed, would take so long to get through. But now you're actually We're to a point where information is becoming ubiquitous. And so that really allows us to do things at a better speed and allows for you to be able to determine more, you know, what are the risks? And you can see those things clearer in shorter periods of time. And that's really important, I think, in our business. Yeah.
Yeah.
Yeah.
So if you had to pick one constraint to focus on and solve over the next 90 days, what would it be?
In terms, in general, in the business and AI and what?
One thing for the business, yeah, that would change the trajectory of the business or improve it.
That's a really good question. I think if I could focus on one thing in the business, it would just be to be able to get the message out there quicker, to be able to get our message out there quicker, to be able to connect with more people. I mean, we're at the point where we want to be able to connect with more people and to be able to engage in more meaningful ways with both advisors and clients. So I think if I could spend time on outreach to both clients and advisors and being able to, you know, to get the word out about who we are and who we serve, I think that would be really meaningful for us. Yeah, would allow us to get to really continue to grow and grow this community. Yeah.
Gotcha. And who would you say is your ideal client, your ICP?
Um, on the advisory side is someone who's very much entrepreneurial. Someone who really has created a business that they want to leave behind or they want to continue on but continue to grow and find place where they can root themselves and feel like they can stay there for life. That's really the type of advisor we attract. And then on the client side, it's really clients who need real guidance and stewardship. People who understand the value in having people to help guide and steward you to make good decisions. That's really what an advisor should do. And so those are the clients that we seek. Yeah, people have complex problems and need some guidance solving those.
Any specific industries or space that you like to double down on?
Um, in terms of investment side or just in general, you mean? Or—
Yeah.
I mean, right now we're looking for opportunities in the market in, in the, uh, growth side of AI, right? So it's really important to be You know, unicorns are going to develop very quickly in this market. And so for us, we're looking for those unicorns while they're learning to fly. We're partnering with some really important groups that are incubating some of what we think are going to be the biggest companies in the world. And we're looking for those opportunities for clients and we're looking to help to get into those early. And so, you know, we're focused on that. And I think on the AI side, you know, we're focused on the investment opportunities and then we're also focused on trying to create efficiencies in the business. You know, those are the two areas I think mostly.
Awesome. So when you look back at your journey, Kim, the wins, the mistakes, what lessons stand out to you? And maybe which ones do you think maybe took longer to learn than they should have?
Well, I think one of the things that I would say as a business owner that I think we as business owners tend to be guilty of is we don't spend enough time to really appreciate the successes we have along the way. Always looking to get to the next summit or to the next peak. And so I feel that there's missed opportunity there. I think that people should really stop and appreciate the work and the, and, and, you know, the, the, um, the success that they've had along the way. It's easy to get lost in the next place and to not be in, in the present, right? I think that's just really an important thing to do. And I think also just know, for me, I think knowing that you're going to make mistakes along the way, just make new ones, right? I call that the idea that we fail forward. We have to be willing to take risks, but we have to take measured risks and we have to understand that you're going to make mistakes. You just have to learn from each one. And like I told my staff, right, we make mistakes, we make new ones, and we continue to fail forward in a way that's meaningful. Because if people don't make mistakes you'll never be curious, you'll never ask the right questions, and you'll be, you'll be stuck. You won't evolve. So to me, it's all about evolution, right? How do you evolve in this period of time? And in general, in life is the constant evolution. So it's about failing forward.
I love that. So last question for you, Kim. When you think about the next stages of the business, what are you most excited about?
I'm most excited about continuing to build out our team, right? Uh, to be, to be able to continue to build out top talent here that really is really passionate about what we do and wants to make a difference. I'm so excited for the people that we are going to surround ourselves with because I think that's really what's going to take us into the next, you know, it's going to take us to the next stratosphere because that's— people are so meaningful to me. And so I'm excited for, you know, people in my industry who I can be around that can help us to support advisors, support clients, and really make a difference in what we're doing.
I love that. So for those who want to learn more, who want to get involved, they can reach out on LinkedIn, brookwoodinvestmentgroup.com. Anywhere else you want to send them?
No. Yeah, yeah, happy to connect on LinkedIn. And yeah, check out our website. I am really trying to be present on LinkedIn. I have a lot of ideas that I've been sharing recently. So yeah, I'd love to people jump in the conversation, love to have conversations with people and just I just love to see what people are doing themselves. It's always interesting to hear what other people are doing and see how we can figure out ways to collaborate and, you know, get them into this cooperative ecosystem.
I love that. And thank you again for your time for joining us this morning.
Yeah, of course.
Thank you to our sponsors of today's episode as well, Achieve Fractional, which provides fractional executive leadership for growing businesses. And if you enjoyed the conversation, share it with a friend, with a colleague. If you're lost, you're not sure where you're stuck at, reach out to Kim and the team. They will guide you through. They can kind of point out the next steps, best habits. Reach out, make the conversation, and we'll see you in the next episode of the Achieve Podcast.










