How Carina Diamond Turned Mentoring Into a Business Model

The Dakota Wealth Management CXO has a plan of succession — not just for her firm, but for the financial services industry as a whole.


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Carina Diamond often likens herself to a shark. But her colleagues and mentees say that while “Big C’s” large book of clients and her six-foot frame can be intimidating, she’s actually better described as a caretaker and a generous guide.

Dakota CEO Peter Raimondi describes her as “a high-level entrepreneur” and “a business-builder.” Brett Orvieto, a mentee who is now a managing partner at Dakota, says that despite Diamond’s big book of business, she still “works hard all the time. From my office, we see her doing well and not resting on her laurels. It’s a lead by example type of thing — we just try to keep up.”

Growth is essential for most businesses, including wealth managers. “You have to be a shark, you have to be constantly moving forward because you have to eat. If you’re not moving forward, you start to diminish, and that is true of everyone on our team,” says Diamond, who was RIA Intel’s Industry Advocate of the Year winner for 2022.

Diamond got her start on the trust side of a bank in northeast Ohio. When it was going under, she was having difficulty finding a job. It wasn’t for a lack of trying — more than 30 firms reached tried to woo her, but Diamond didn’t believe that any were a good fit.

Then, in 2001, at a Cleveland Browns football game, her friend Mark Goldfarb asked her if she wanted a job at the wealth management company he’d recently started. Diamond said she’d give it a shot.

The stint turned into fifteen years. At the end of that run, when Goldfarb was selling his company, Diamond decided to go independent. She started her own RIA, Springside Partners, and grew it to $250 million in assets in three years. But as a solo entrepreneur, she missed collaborating with and mentoring colleagues. Diamond also wanted her staff to have equity in the firm. But at Springside, that wasn’t possible.

Then she met Dakota CEO Peter Raimondi. Diamond was particularly drawn to Raimondi’s ideas about making staff shareholders in the company. After a third meeting at Diamond’s offices in Akron, Springside became a part of Dakota. Diamond says she “was able to bring equity to everyone that completely deserved it.”

Raimondi says that “Dakota” is a Native American word that means “friends and allies.” “That’s really what this business is — folks working together for a common purpose: to satisfy client goals financially and employee goals professionally,” he says. Raimondi wanted Diamond to assume an executive role at Dakota, because he felt that she epitomized that ethos, so she became chief experience officer as a way to give the idea full-time support.

The key to Diamond’s success as CXO has been her ability to leverage a belief that humans are programmed to want to help. She supports and encourages her colleagues and clients to be more vulnerable — vulnerability provides information, she says, and that gives them a path to help themselves and one another.

To illustrate her approach, Diamond likes to tell a story about how her new neighbors once helped her carry three tons of rocks for her yard, hauling them bag by bag to the front of her home from pallets that the company had left on the street. Because she was new to the neighborhood, she had tried to move the sacks of stone by herself. As her new neighbors drove by and saw Diamond struggling, “they must have wondered, who is this crazy woman?” she says with a laugh. Not only did they help her with the rocks, they also brought cold drinks and dinner.

That experience parallels Diamond’s professional life. First, her neighbors helped because she allowed herself to be vulnerable about what she didn’t know by showing the neighbors how ill-prepared she was for yard work; and second, she was able to silence her ego and accept their help. Her neighbors helped because Diamond, even in her role outside of work as a novice landscaper, created the conditions to get the support her project needed.

Since joining Dakota two years ago, Diamond’s leadership and what Raimondi calls her “high-level entrepreneurial skills” have helped the firm triple both its assets and its staff. “I am sort of the conductor. I make sure we have good content, but I trust others to own that content. I establish the broad parameters and tell the team what we need, and then I believe in my colleagues and empower them.”

She says her monthly business development call with her team is critical to Dakota’s growth, because it gives her the opportunity to listen to her colleagues’ problems and ideas. Diamond surrounds herself with a diverse group of intelligent people, and she stresses that she doesn’t want to be the smartest person in the room. As she puts it, she tries to “give [her staff] the opportunity, keep it open-ended, and get out of the way.”

Giving people autonomy comes with challenges. But Diamond’s approach to mentorship has created a strong talent pipeline. Marc Servodio is one example. Before Servodio founded his own firm, Vita Advisors, he was a finance student at the University of Akron and worked as an intern for Diamond at Springside. He eventually became more involved in the business and client side of the firm and then decided to join full-time after graduation.

Diamond always made herself available for Servodio’s questions and talked to him about the firm’s clients and her rationale for various key decisions. She also regularly invited Servodio to client meetings, even during his undergrad internship, as a way to give him a feel for the meetings and some face time with clients. Although he didn’t know it at the time, Diamond soon began preparing Servodio to take on more responsibility, giving him a larger role in meetings and the opportunity to actually present to clients.

Servodio says that Diamond was essentially training both sides of the table — her advisors and the client. He calls the process, “Carina 101.” He says that if it hadn’t been for his time apprenticing under Diamond, he wouldn’t have his own firm, and he might not even be working in finance. “A lot of my classmates at [Akron) are no longer in the industry,” he says, explaining that once they had secured a job after graduation, they were immediately expected to start producing. As he puts it, they were “just-graduated 20-year-olds advising 60-year-old retirees.”

Diamond says that she is unusual because she’s all about abundance. “I’m not scared of others meeting my clients,” she says, “because I don’t ever want clients to think it’s just me. It takes a village to deliver high-end financial advice.”

Diamond started her mentoring practice in part because of a shortage of good people applying for jobs in the industry. She linked up with the University of Akron and, as was the case with Servodio, began to hire their accounting and financial planning students as interns. She also got involved with Diversitas, a partnership with twenty-four universities that’s designed to improve diversity, equity, and inclusion in financial planning and wealth management.

Diversitas also works to shift the perception of the wealth management industry from a sales- and product-oriented profession to one that helps people with their financial goals and legacies. “In order for the financial planning and wealth management industry to better serve the changing investor population, its talent pool needs to better reflect the client base that it will serve in the future,” Diamond says. “Our profession will die if we don’t have enough diversity.”

Diamond sees her mentoring work as a moral obligation to both the firm and the profession. “When you’re trained in financial planning, one of the biggest things you learn is to make sure your clients don’t run out of money,” she says. “It’s kind of the same thing when you’re running a business — you need a plan of succession. What are we doing to make sure that our practice doesn’t run out of talent? Mentoring is the solution to the succession issue. Every time I invest in a young person, I am investing in them, and our relationship, but also in the continuity of the firm.”

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