The Diamond Podcast for Financial Advisors

Mindy Diamond Financial Advisor Recruiter and Consultant

Launched in 2017 as Mindy Diamond on Independence, the show has taken on a broader perspective beyond the independent space to include topics, insights, and candid conversations around financial advisor transitions, growth, and an ever-changing industry landscape. Each episode is designed to offer objective guidance and actionable advice with some of the industry’s brightest movers and shakers.

  1. 3d ago

    Build, Grow & Transact: From Breakaway to Transaction in 3 Years

    Patrick Larkin, Partner & Practice Leader, Cerity Partners Three years after launching his independent RIA, Patrick Larkin merged with Cerity Partners—but not because that was the original plan. He explains how ownership changed the way he viewed enterprise value, optionality, and the future of his business. In Summary Going independent is often viewed as the destination. Patrick Larkin discovered it was just the beginning. Louis sits down with Patrick, Partner and Practice Leader at Cerity Partners and former founder of Oak Hill Wealth Advisors, to discuss an unconventional journey: leaving Wells Fargo to build an independent RIA, then choosing to merge that business just three years later. Rather than following a predetermined exit strategy, Patrick shares how ownership fundamentally changed the way he thought about enterprise value. A conversation with a prospective acquirer revealed that buyers weren’t interested in purchasing a book of business—they were looking for a business. That realization reshaped how he invested, hired, delegated, and ultimately positioned his firm for the future. The conversation from our Build Grow & Transact series also offers a candid look at life after a merger, from evaluating cultural fit and partnership to balancing autonomy with the resources of a larger organization. More broadly, it illustrates how ownership creates optionality—and why the most valuable decision an advisor makes may not be the one they originally envisioned. The Storyline After spending nearly 15 years building a successful practice at AG Edwards, Wachovia, and Wells Fargo, Patrick Larkin launched Oak Hill Wealth Advisors in 2022 with a simple objective: build a business on his own terms. Like many advisors, he expected independence to be the final destination for a long time. But then there was the realization that ownership changes more than economics; it changes perspective. And it became the beginning of an entirely different way of thinking. As acquisition inquiries arrived sooner than expected, Patrick realized something that fundamentally changed his strategy. Sophisticated buyers weren’t evaluating his client relationships as a book of business; they were evaluating Oak Hill as an enterprise. That insight shifted his priorities from maximizing short-term profitability to building a business that could thrive beyond its founder. Just three years after launching, Patrick chose to merge with Cerity Partners—not because he was looking for an exit, but because he believed it strengthened the future for his clients, his team, and his family. Louis and Patrick explore what led to that decision, how ownership increased the value of his business almost immediately, why he compares independence to an IPO, and what advisors should consider if they hope to create options for the future—even if they don’t yet know what that future looks like. Topics Covered Building enterprise value versus maximizing annual income Creating optionality through ownership Leaving Wells Fargo to launch an independent RIA Why buyers value businesses more than books of business Evaluating strategic partners and acquisition opportunities The economics of independence and business valuation Life after merging with Cerity Partners Balancing autonomy with enterprise-scale resources Leadership, succession, and building beyond the founder Long-term ownership and partnership models > Download a transcript of this episode… Listen and Learn Highlights for Advisors Why did Patrick decide to leave Wells Fargo? (11:07) Patrick explains why growing frustrations around control, firm priorities, and the ability to build his business eventually outweighed the comfort of staying put. How did going independent immediately change the value of his business? (21:42) Patrick introduces one of the episode’s biggest ideas: why launching Oak Hill felt like taking a company public and how ownership increased the firm’s value almost overnight. Why did Patrick sell only three years after becoming independent? (20:03) An unexpected conversation with a prospective acquirer completely changed how he viewed enterprise value and accelerated his long-term thinking. What separates a business from a book of business? (21:42) Patrick discusses why recruiting advisors, delegating client relationships, and investing beyond himself made Oak Hill more attractive to strategic buyers. Why Cerity Partners? (26:48) Rather than focusing on valuation, Cerity emphasized culture, partnership, and long-term alignment—qualities Patrick says ultimately mattered most. What is life actually like after a merger? (37:57) Patrick offers an unusually candid perspective on autonomy, leadership, and why he says he hasn’t second-guessed the decision once. Key Takeaways Ownership creates opportunities that often aren’t visible until after independence. Enterprise value is built by creating a business that can thrive beyond its founder. The first acquisition conversation can be valuable even if no transaction occurs. Cultural alignment may ultimately matter more than valuation when selecting a long-term partner. Independence doesn’t eliminate future options—it expands them. Strategic transactions can strengthen outcomes for clients, employees, and owners simultaneously. The goal isn’t simply to own a business; it’s to create choices for what comes next. https://youtu.be/f7FGLGjBbyo Quotable Moments “The day Oak Hill launched felt like the business had gone public.” “Potential acquirers weren’t interested in buying a book. They were interested in buying a business.” “Ownership isn’t simply about control. It’s about creating optionality.” “The fear of leaving is almost always worse than the actual experience of leaving.” FAQs Why did Patrick Larkin merge with Cerity Partners only three years after launching his RIA? Patrick explains that independence changed how he viewed enterprise value. After learning what sophisticated buyers were actually looking for, he intentionally built Oak Hill as a business rather than simply managing for annual profitability. Why does Patrick compare independence to an IPO? Because ownership immediately transformed the economic value of his practice. Rather than participating in an internal succession model, he owned an independent enterprise that carried substantially greater market value. What changed after Patrick became independent? Beyond gaining control, he began making decisions through the lens of enterprise value—investing in advisors, systems, and infrastructure that would make the business less dependent on him personally. What made Cerity Partners stand out? Patrick cites the firm’s culture, partnership model, meritocracy, long-term vision, and ability to combine local autonomy with enterprise-level capabilities. Is this episode only relevant for advisors considering selling? No. The broader lesson is that ownership creates flexibility. Whether an advisor ultimately remains independent or joins another organization, understanding how enterprise value is created can influence decisions from day one. What is the biggest lesson Patrick hopes advisors take away? That independence isn’t simply about leaving a firm. It’s about creating the ability to choose what comes next on your own terms. Patrick explains that independence changed how he viewed enterprise value. After learning what sophisticated buyers were actually looking for, he intentionally built Oak Hill as a business rather than simply managing for annual profitability. Because ownership immediately transformed the economic value of his practice. Rather than participating in an internal succession model, he owned an independent enterprise that carried substantially greater market value. Beyond gaining control, he began making decisions through the lens of enterprise value—investing in advisors, systems, and infrastructure that would make the business less dependent on him personally. Patrick cites the firm’s culture, partnership model, meritocracy, long-term vision, and ability to combine local autonomy with enterprise-level capabilities. No. The broader lesson is that ownership creates flexibility. Whether an advisor ultimately remains independent or joins another organization, understanding how enterprise value is created can influence decisions from day one. That independence isn’t simply about leaving a firm. It’s about creating the ability to choose what comes next on your own terms. Related Resources From Start-Up to $31B Behemoth RIA: The Catalysts Behind the Growth of Mega-Firm Cerity Partners Ownership Matters: What Advisors Need to Know When Evaluating Firms Top Tips for Setting Your Business Up for Success Years Before a Move Patrick Larkin Partner and Practice Leader Patrick is a Partner and Practice Leader in the Lansdowne, VA office. He is a member of the Lansdowne Practice, where he works closely with families, foundations, and non-profits to help them define and achieve their financial goals with clarity and confidence. With a deep specialization in retirement income distribution planning and complex risk and wealth management strategies, Patrick is known for helping clients simplify complicated financial decisions, reduce uncertainty, and build sustainable, long-term plans. His approach emphasizes fiduciary responsibility, transparency, and personalized guidance — ensuring clients always feel informed and empowered. Prior to joining Cerity Partners, Patrick was the founding member of Oak Hill Wealth Advisors, where he built a highly respected independent advisory practice that earned the trust of families, professionals, and mission-driven organizations across the region. His leadership was instru

  2. Aug 6

    Why AI Matters Now: How a $1.5B RIA is Building the Firm of the Future

    Ryan Belanger — Founder & CEO, Claro Advisors Most firms are adding AI to existing workflows. Ryan Belanger chose a different path, acquiring a fintech company and rebuilding Claro Advisors around an AI-native platform. He explains why he believes the future belongs to firms that rethink how they operate, not just the tools they use. In Summary Most firms view AI as another technology investment. Ryan Belanger sees it as a business strategy. Louis sits down with the Founder & CEO of Claro Advisors to discuss why his $1.5 billion RIA acquired a fintech company, built an AI-native operating platform, and believes the firms that gain the biggest advantage won’t simply adopt new technology—they’ll rethink how their businesses are built. The conversation also explores the broader philosophy behind that decision. Ryan shares why he’s consistently chosen unconventional paths—from recruiting younger advisors and embracing a partnership model built around ownership to investing in proprietary technology instead of relying on third-party solutions. For advisors, the bigger question isn’t simply how AI will change their workflow. It’s how it may change what it takes to build a durable, differentiated advisory firm. The Storyline Every generation of wealth management has been shaped by a different competitive advantage. For some, independence paved the way to build unique branding and a bespoke client experience. Inorganic growth and M&A gave many firms access to scale and growth. Today, many believe the next advantage will come from artificial intelligence. But simply adopting AI may not be enough. Ryan Belanger has spent his career challenging conventional thinking. He left Morgan Stanley in 2012, well before independence became mainstream. He built Claro Advisors by investing in younger advisors instead of competing for established producers. He embraced a partnership model centered on advisor ownership rather than restrictive employment structures. And when AI began reshaping the industry, he made another unconventional decision: instead of licensing another technology platform, Claro acquired a fintech company and built its own AI-native operating system. Louis explores the reasoning behind each decision and the philosophy that connects them. Ryan explains why he believes proprietary technology will become a defining competitive advantage, how Claro’s AI platform, Claire, is changing advisor workflows, and why the biggest opportunity isn’t replacing advisors; it’s giving them more time to do the work clients value most. The conversation also tackles practical questions facing every advisory firm: how to integrate AI responsibly, where human judgment continues to matter most, and why the firms best positioned for the future may be the ones willing to redesign their businesses instead of simply adding another layer of technology. Topics Covered AI-native advisory firms Acquiring a fintech versus licensing technology Building proprietary advisor technology Advisor productivity and workflow automation Recruiting and developing younger advisors 1099 partnership model and advisor autonomy Enterprise building and long-term differentiation AI governance and advisor trust The future of wealth management technology > Download a transcript of this episode… Listen and Learn Highlights for Advisors Why did Ryan launch independently long before it became common? (7:30) Ryan explains why leaving Morgan Stanley in 2012 wasn’t simply about independence—it was about creating a better business model while betting on himself. Why recruit emerging advisors instead of established producers? (15:00) Ryan shares why investing in younger advisors has become one of Claro’s greatest competitive advantages and succession strategies. Why would an RIA buy a technology company? (23:45) Rather than licensing another platform, Ryan explains why Claro acquired NDVR to build proprietary technology that could fundamentally change advisor workflows. How does Claire actually help advisors day-to-day? (33:00) From meeting preparation and client follow-up to portfolio management and workflow automation, Ryan walks through how AI is saving advisors meaningful time. Will AI replace advisors—or make them better? (36:30) Ryan discusses where AI belongs, where human advice remains essential, and why he believes technology should enhance – not replace – the advisor relationship. What does the advisory firm of the future look like? (38:20) Ryan shares his long-term view of how AI, proprietary technology, and advisor expectations will reshape wealth management over the next decade. Key Takeaways Ryan believes firms that build AI into the foundation of their businesses will create greater long-term differentiation than those simply adding new software. Claro’s acquisition of a fintech company reflects a strategy of owning core technology rather than relying exclusively on third-party vendors. AI is most valuable when it eliminates administrative work, allowing advisors to spend more time serving clients. Recruiting younger advisors and investing in long-term talent has become a defining part of Claro’s growth strategy. Advisor autonomy, equity participation, and technology can create stronger retention than restrictive employment models. Human relationships remain central to wealth management, even as AI becomes increasingly capable. The firms that adapt fastest may be those willing to rethink their operating model—not just their technology stack. https://youtu.be/7XvSXi0PzXI Quotable Moments “I wanted to build something that was integrated instead of just layering another tool on top.” “We’re trying to make really good advisors become super advisors.” “Clients still want advice from a person—but they’re going to expect that person to know how to use AI.” “The firms that win won’t necessarily be the ones using the most technology. They’ll be the ones building differently.” FAQs Why did Claro Advisors acquire a fintech company? Ryan believed owning proprietary technology would create greater long-term differentiation than licensing another collection of third-party tools. What is Claire by Claro? Claire is Claro Advisors’ AI-powered chief of staff, designed to automate advisor workflows, prepare meetings, organize client information, and streamline operational tasks. How is Claro using AI differently than many RIAs? Rather than layering AI onto multiple disconnected applications, Claro built an integrated operating platform where AI has access to the advisor’s workflow, planning, portfolio, and client information. Will AI replace financial advisors? Ryan believes AI will automate much of the administrative work advisors perform today, but that clients—particularly those with more complex needs—will continue to value human advice and relationships. How does Claro recruit advisors? The firm emphasizes advisor ownership, partnership, equity participation, technology, and operational support instead of relying primarily on acquisition-based recruiting models. What does Ryan believe will differentiate advisory firms in the future? He believes proprietary technology, integrated AI, and the ability to improve advisor productivity will become increasingly important competitive advantages. Ryan believed owning proprietary technology would create greater long-term differentiation than licensing another collection of third-party tools. Claire is Claro Advisors’ AI-powered chief of staff, designed to automate advisor workflows, prepare meetings, organize client information, and streamline operational tasks. Rather than layering AI onto multiple disconnected applications, Claro built an integrated operating platform where AI has access to the advisor’s workflow, planning, portfolio, and client information. Ryan believes AI will automate much of the administrative work advisors perform today, but that clients—particularly those with more complex needs—will continue to value human advice and relationships. The firm emphasizes advisor ownership, partnership, equity participation, technology, and operational support instead of relying primarily on acquisition-based recruiting models. He believes proprietary technology, integrated AI, and the ability to improve advisor productivity will become increasingly important competitive advantages. Related Resources Why AI Matters Now: Filling the Estate Planning Gap with Wealth.com Emotional Intelligence: The “Untouchable” Differentiator in an AI World Diamond Consultants Annual Advisor Transition Report Ryan Belanger Chief Executive Officer & Founder Ryan founded Claro Advisors in 2012 after seven years at Morgan Stanley. He named the company after a Latin phrase “to make clear in the mind.” All Claro advisors strive to give their clients clarity and transparency, core tenants of the firm. Claro is continuously recognized within industry for its growth and thought leadership. In 2004, Ryan received a BA in Economics from The College of the Holy Cross and in 2009, he earned the Certified Financial Planner™ distinction. He is most proud of his philanthropic activity. Along with his wife Rachel, they started a foundation that raises money for genetic research in the name of their late daughter, Bella. Their focus is on extreme rare disease. Ryan resides in Boston’s Back Bay with his wife Rachel and their three children. He enjoys exercising, golfing, reading and spending time with his family. He has been featured in numerous magazines and industry publications and is regularly on television sharing his market thoughts. NOTE: The views and opinions expressed by the guests on this podcast are their own and do not necessarily reflect the vi

  3. Jul 30

    IBD vs. RIA: A Special Industry Update on Independence

    With Josh Tomolak, Vice President of Independent Advisor Services, Diamond Consultants Louis Diamond and Josh Tomolak unpack today’s IBD vs. RIA landscape, explaining what has changed, where each model excels, and how to determine which path best supports the business you want to build. In Summary The independent wealth management landscape has changed dramatically, making the decision between an independent broker dealer (IBD) and an RIA more nuanced than ever before. Louis Diamond welcomes Diamond Consultants’ Vice President of Independent Advisor Services, Josh Tomolak, for a practical discussion of how the independent space has evolved, what truly differentiates the IBD and RIA models today, and how advisors can evaluate which path best aligns with the business they want to build. The Storyline Not long ago, the decision to become independent was relatively straightforward. Advisors either remained with a traditional firm or pursued independence through one of a limited number of models. Today, the conversation is far more complex. Independent broker dealers have significantly expanded their capabilities, offering stronger technology, larger transition packages, greater flexibility, and even pathways to RIA ownership. At the same time, the RIA ecosystem has matured into a sophisticated marketplace supported by multiple custodians, outsourced service providers, institutional capital, and enterprise platforms that rival many of the industry’s largest firms. As these developments have unfolded, the traditional distinctions between an IBD and an RIA have become less obvious. Advisors evaluating their options are no longer simply asking whether they should become independent—they’re asking which model best supports the clients they serve, the business they envision, and the lifestyle they want to create. In this Industry Update, Louis and Josh unpack the realities behind the IBD vs. RIA decision. They discuss where the two models overlap, where meaningful differences still exist, and why factors like service, technology, economics, operational responsibility, enterprise value, and long-term optionality often matter more than labels alone. Whether you’re considering changing independent firms, launching your own RIA, or simply want a better understanding of how the independent landscape has evolved, this conversation provides an objective framework for evaluating today’s choices—and preparing for tomorrow’s opportunities. Topics Covered Independent Broker Dealer (IBD) vs. RIA models The evolution of supportive independence Technology investments across the independent space Transition support and advisor mobility Capital solutions and recruiting economics Business formation and enterprise value Launching an independent RIA Multi-custodial platforms and open architecture Minority investments and succession planning Future trends shaping advisor independence > Download a transcript of this episode… Listen and Learn Highlights for Advisors Why are already-independent advisors reconsidering their current model? (5:27) Josh explains why service, technology, economics, and growing optionality are causing advisors to reevaluate their existing affiliations. How have independent broker dealers and RIAs become more alike? (19:28) Louis and Josh discuss the growing convergence between the two models and why the distinction is becoming less obvious than many advisors assume. What really separates an IBD from an RIA? (25:04) A practical discussion of autonomy, compliance, flexibility, custody, economics, and advisor experience. What misconceptions keep advisors from launching an RIA? (36:29) Josh outlines the “Four Pillars” of launching an RIA and explains where advisors tend to either overestimate or underestimate the operational realities. Which advisors thrive most in each model? (33:12) The conversation explores why there isn’t a universally “better” model—only one that’s better aligned with an advisor’s goals. What trends are quietly reshaping independence? (42:13) Minority investments, enterprise value, business formation, and changing revenue models may have an even greater impact than advisors realize today. Key Takeaways Independence has evolved from a destination into an ongoing strategic decision. Independent broker dealers have significantly improved technology, transition support, economics, and flexibility. The RIA ecosystem has matured into a highly sophisticated marketplace with broad outsourcing and support options. Choosing between an IBD and an RIA should begin with long-term business objectives—not industry perceptions. Building a valuable business depends more on business structure and scalability than simply growing assets. Advisors considering independence should evaluate models with an open mind rather than relying on outdated assumptions. The next decade will likely bring continued convergence between independent business models. https://youtu.be/jHDVso2TsmQ Quotable Moments “The question is no longer, ‘Do I want to go independent?’ The question is, ‘What kind of independence makes the most sense for my clients, business, and goals?’” “Business formation is far more important than assets under management.” “The way you build your business will ultimately determine how valuable that business becomes.” “Everything in an RIA is going to cost you either your time or your money.” FAQs Is there still a meaningful difference between an IBD and an RIA? Yes. While the two models increasingly overlap, they differ in areas such as flexibility, compliance structure, operational responsibility, economics, and control. Why are more independent advisors changing firms today? Improved technology, stronger transition support, evolving economics, and better service models are prompting many advisors to reassess whether their current platform still fits their business. Is launching an RIA easier than it used to be? Yes. Supportive independence, outsourced service providers, and improved custodial resources have significantly reduced many of the historical barriers. Does every entrepreneurial advisor belong in the RIA model? No. The best fit depends on an advisor’s appetite for ownership, customization, operational responsibility, and long-term vision. What matters more: assets under management or how the business is built? Josh argues that scalable business formation often has a greater impact on enterprise value than AUM alone. What’s the biggest mistake advisors make when evaluating independence? Starting with assumptions instead of objectives. The most effective due diligence begins by defining the business you’re trying to build, then identifying the model best suited to support it. Yes. While the two models increasingly overlap, they differ in areas such as flexibility, compliance structure, operational responsibility, economics, and control. Improved technology, stronger transition support, evolving economics, and better service models are prompting many advisors to reassess whether their current platform still fits their business. Yes. Supportive independence, outsourced service providers, and improved custodial resources have significantly reduced many of the historical barriers. No. The best fit depends on an advisor’s appetite for ownership, customization, operational responsibility, and long-term vision. Josh argues that scalable business formation often has a greater impact on enterprise value than AUM alone. Starting with assumptions instead of objectives. The most effective due diligence begins by defining the business you’re trying to build, then identifying the model best suited to support it. Related Resources IBD vs. RIA Comparison Guide IBD vs. RIA Revisited: Two Independent Pathways for Advisors to Consider NOTE: The views and opinions expressed by the guests on this podcast are their own and do not necessarily reflect the views and opinions of Diamond Consultants. Neither Diamond Consultants nor the guests on this podcast are compensated in any way for their participation. View the transcript of this episode… IBD vs. RIA: A Special Industry Update on Independence A conversation with Louis Diamond and Josh Tomolak, Vice President of Independent Advisor Services at Diamond Consultants.      Louis Diamond: Welcome to the latest episode of our podcast series for financial advisors. Today’s episode is IBD vs. RIA: A Special Industry Update on Independence. It’s a conversation with Josh Tomolak, our Vice President of Independent Advisor Services. I’m Louis Diamond, and this is the Diamond Podcast for Financial Advisors. Mindy Diamond: At Diamond Consultants, we help elite advisors identify the right environment for their businesses to thrive, whether that’s at a wirehouse, boutique, or independent firm. With nearly three decades of experience, we’ve guided thousands of advisors and represented more than a quarter of a trillion dollars in assets transitioned. And each year, one in four advisors managing a billion dollars or more who change firms are our clients. Our process is education driven and based on building relationships, starting as your strategic partner well before you’re even thinking of a move. To schedule a confidential conversation, call us at (908) 879-1002. Wondering why advisors change firms and where they’re headed? Are transition deals going up or down? Those very questions and more inspired us to create our annual advisor transition report. It’s the award-winning data-driven resource designed for advisors that connects the dots between the motivations around movement and the firm’s appetite for top talent. Arm yourself with the knowledge you need to make sm

  4. Jul 23

    Build, Grow & Transact: $3.5B Cyndeo on Thinking Like a $25B Firm

    Matt Kilgroe — President & CEO, Cyndeo Wealth Partners Matt Kilgroe shares how Cyndeo Wealth Partners grew from a newly launched $1.2B RIA to a $3.5B enterprise, and why the next challenge isn’t independence, but building a firm capable of reaching $25B.  In Summary Five years after launching Cyndeo Wealth Partners from UBS, Matt Kilgroe returns to the podcast to discuss what happens after independence. Rather than focusing on the transition itself, Louis and Matt explore the next phase of growth: scaling an advisory business, attracting talent, developing niche expertise, taking on outside capital, and building an enterprise designed to last. Along the way, Matt shares how Cyndeo expanded from $1.2B to $3.5B, why serving professional athletes required a different business model, and what led the firm to partner with Rise Growth Partners as it looks toward a $25B future.  The Storyline For many advisors, independence is viewed as the finish line. For Matt Kilgroe, it became the starting point. When Cyndeo Wealth Partners launched in 2020, the goal wasn’t simply to leave the wirehouse behind. It was to build a business with the flexibility to grow in ways that simply weren’t possible before. Five years later, that vision has evolved into something much larger. Cyndeo has nearly tripled in size, expanded its niche serving professional athletes and entertainers, recruited advisors, added specialized operational talent, and recently welcomed Rise Growth Partners as a minority investor to help accelerate its next phase of growth. The conversation explores what changes when firm leaders stop thinking like advisors managing successful practices and begin thinking like CEOs building enduring enterprises. The discussion spans succession planning, capital strategy, recruiting, organizational design, and the mindset required to scale from billions to tens of billions—all while remaining focused on clients and culture.  Topics Covered Building an enterprise beyond independence Scaling from $1.2B to $3.5B in assets Organic growth versus recruiting Serving professional athletes and entertainers Why fiduciary independence matters for niche client segments Building operational infrastructure for growth Partnering with Dynasty Financial Partners Minority capital and Rise Growth Partners Succession planning and employee ownership Thinking from $3.5B to $25B > Download a transcript of this episode… Listen and Learn Highlights for Advisors What did Matt learn after transitioning nearly 98% of his clients? (06:20) Why client relationships—not firm logos—proved to be the firm’s greatest asset during one of the most challenging transitions imaginable. How did Cyndeo nearly triple in size in five years? (16:10) Matt discusses the combination of niche specialization, disciplined organic growth, recruiting, and operational investment that fueled the firm’s expansion. Why has Cyndeo become a destination for professional athletes? (17:15) The conversation explores how deep industry expertise, fiduciary flexibility, and specialized service created a business that would have been difficult to build inside a wirehouse. Why bring on a minority capital partner when the business was already thriving? (24:15) Matt explains why succession planning, future recruiting, and long-term enterprise growth made outside capital the right decision. How should advisors think about ownership versus compensation? (35:40) A candid discussion about enterprise value, equity, and why many advisors underestimate the long-term economics of ownership. What does it actually take to scale toward $25B? (42:20) From hiring executive talent to expanding geographically, Matt shares how he’s thinking about the next chapter of Cyndeo’s evolution. Key Takeaways Independence creates opportunities that extend well beyond higher payouts, including enterprise value, recruiting flexibility, and ownership. Scaling a business requires investing in operational leadership, not just adding advisors. Specialized client niches demand expertise that goes well beyond investment management. Outside capital can accelerate growth when it’s aligned with long-term strategy rather than an exit. Building an enduring enterprise requires thinking differently about succession, talent, governance, and equity. https://youtu.be/WRYJd9Lkt7o Quotable Moments “Don’t rent your practice. Own it.” “You can’t work in those niches and not be a fiduciary.” “We’re not done.” “The road from $3B to $25B is going to really compound on your equity.”  FAQs Why did Cyndeo decide to take on a minority capital partner? To support its next phase of growth, strengthen succession planning, recruit additional talent, and benefit from the experience of leaders who have successfully scaled wealth management businesses before. How did Cyndeo grow from $1.2B to $3.5B? Through a combination of consistent organic growth, specialized client niches, advisor recruiting, and investments in operational infrastructure. Why is serving professional athletes or other niche client segments different from serving traditional wealth clients? Niche client segments often face unique financial decisions involving private investments, business opportunities, and career transitions that require specialized knowledge and a fiduciary framework. What advantages did independence create that weren’t available inside a wirehouse? Matt points to greater flexibility around private investments, the ability to build specialized client experiences, reward employees with equity, and create an enterprise with lasting value. How should advisors think about building versus joining an independent firm? The discussion highlights the tradeoffs between creating your own firm and joining an established independent enterprise, emphasizing that ownership and long-term equity often matter more than headline payouts. What does Matt believe is required to build a $25B firm? A willingness to invest beyond advisors alone, adding executive leadership, expanding geographically, recruiting strategically, and maintaining a long-term enterprise mindset. To support its next phase of growth, strengthen succession planning, recruit additional talent, and benefit from the experience of leaders who have successfully scaled wealth management businesses before. Through a combination of consistent organic growth, specialized client niches, advisor recruiting, and investments in operational infrastructure. Niche client segments often face unique financial decisions involving private investments, business opportunities, and career transitions that require specialized knowledge and a fiduciary framework. Matt points to greater flexibility around private investments, the ability to build specialized client experiences, reward employees with equity, and create an enterprise with lasting value. The discussion highlights the tradeoffs between creating your own firm and joining an established independent enterprise, emphasizing that ownership and long-term equity often matter more than headline payouts. A willingness to invest beyond advisors alone, adding executive leadership, expanding geographically, recruiting strategically, and maintaining a long-term enterprise mindset. Related Resources Article: Your Practice Isn’t Worth What You Think Most advisors misjudge their business’s value, not because of the number, but because of the framework. Learn what really drives enterprise value. Rise and Reinvent: Joe Duran on Building and Rebuilding World-Class Firms He’s built and rebuilt some of the industry’s most successful firms and now he’s helping others do the same. In this episode, Joe Duran, the founder of Rise Growth Partners, shares lessons from building, selling, and starting again, and how staying curious and adaptable fuels lasting success. Matt Kilgroe President/CEO Prior to launching Cyndeo Wealth Partners in 2020, Matt ran advisory teams at Merrill Lynch and UBS Financial for 29 years. Providing guidance, counsel, and strategy for families the firm serves is Matt’s passion. In addition to his role as an advisor, Matt works in a leadership capacity for Cyndeo while also helping with business development. Matt has been recognized by Barron’s as a Top 1000 or Top 1200 Advisor consistently since 2009. In 2020 Forbes named him to their “Best-In-State Wealth Advisor” list. A graduate of Eckerd College, Matt has served on the Board of Trustees at his alma mater since 2012. His three children are his pride and joy. Daughter Carrington owns Sunstate Yoga studio in St. Petersburg, son Kent is a financial advisor with Cyndeo, and daughter Jillian recently graduated Florida State University. An athlete in college, Matt continues to enjoy staying in shape, playing basketball, and bike riding. NOTE: The views and opinions expressed by the guests on this podcast are their own and do not necessarily reflect the views and opinions of Diamond Consultants. Neither Diamond Consultants nor the guests on this podcast are compensated in any way for their participation. View the transcript of this episode… True Alignment: Advising Business Owners on Wealth, Significance, and Value A conversation with Jason Diamond, Nick Hubert and Taylor Gentry – Founding Partners at Panoramic Capital Partners. Jason Diamond: Welcome to the latest episode of our podcast series for financial advisors. Today’s episode is True Alignment: Advising Business Owners on Wealth, Significance, and Value. It’s a conversation with Nick Hubert and Taylor Gentry, Founding Partners, Panoramic Capital Partners. I’m Jason Diamond and this is the Diamond Podcast for Financial Advisors. Mindy Diamond: At Diamond Consultants,

  5. Jul 16

    Lessons from the Links: From Golf Pro to $5B Family Office Partner

    With Constantine Hatzivassiliou—Partner, Certuity Golf taught Constantine Hatzivassiliou how to perform under pressure. Building a nearly $5B multi-family office taught him that the best advisors become the first call when life, not just the markets, gets complicated. In Summary Many advisors spend years mastering investments, but for affluent families, portfolio management is often just the starting point. Jason Diamond welcomes Constantine Hatzivassiliou, Partner at Certuity, to discuss how his journey from aspiring professional golfer to leader of a nearly $5B multi-family office shaped his approach to client service. Their conversation explores why trust is earned long before a crisis, how family office services evolve naturally from client needs, and why the advisor’s role increasingly resembles that of a quarterback coordinating every aspect of a family’s financial life. The discussion also examines organic growth, referrals, fiduciary advice, private equity’s impact on the RIA landscape, and the qualities that allow advisors to become indispensable over decades—not just market cycles. The Storyline Many advisors spend years perfecting investment management. But as clients become more successful, the job changes. The questions become bigger than portfolio construction. A business is being sold. A family dynamic shifts. A tax issue emerges. An estate plan needs updating. Suddenly, the advisor isn’t simply managing assets—they’re coordinating decisions, relationships, and emotions. For Constantine, that broader role was shaped long before he entered wealth management. As an aspiring professional golfer, he learned lessons about discipline, preparation, and performing under pressure that continue to influence how he serves clients today. Jason and Constantine explore how Certuity grew from approximately $210 million in assets to nearly $5B, not through acquisitions but through referrals and a service model built on becoming indispensable to the families they advise. Constantine explains why he believes the best advisors function more like quarterbacks than portfolio managers, orchestrating the many moving pieces that come with significant wealth. The conversation also examines the evolution of the multi-family office model, the role of fiduciary advice, the impact of private equity on the advisory landscape, and why experience, judgment, and trust remain the qualities clients value most. Ultimately, this episode is about what it takes to become the first call when life – not just the markets – becomes complicated. Topics Covered Lessons from professional golf that translate to wealth management Building Certuity from $210mm to nearly $5B in assets What distinguishes a multi-family office from a traditional RIA Why referrals fuel long-term organic growth Becoming the “first call” for affluent families Fiduciary advice and the evolution of the advisory profession Family office services beyond investment management Private equity and M&A in the RIA space Developing the next generation of advisors Trust, relationships, and lifetime client service > Download a transcript of this episode… Listen and Learn Highlights for Advisors How did professional golf prepare Constantine for advising wealthy families? (3:45) Constantine explains why competing under pressure taught him discipline, emotional control, and process—qualities that now guide every client relationship. How did Certuity grow from $210 million to nearly $5 billion? (8:00) He shares why nearly all of the firm’s growth has come organically through client referrals rather than acquisitions or aggressive recruiting. What separates a multi-family office from a traditional advisory firm? (11:45) The conversation explores how expanding into trust, estate, tax, and family office services became a response to client needs—not a business strategy. Why should advisors think of themselves as quarterbacks? (20:00) Constantine recounts a client business sale that fell apart at the closing table and explains why advisors often become the person holding everything together. How does Certuity view private equity and acquisitions? (36:20) Jason and Constantine discuss when outside capital can make sense—and why Certuity has chosen a different path centered on client alignment. Why do wisdom and experience still matter in an AI-driven world? (29:30) Despite advances in technology, Constantine argues that judgment, trust, and perspective remain the qualities affluent families value most. Key Takeaways High-net-worth clients increasingly value coordination, judgment, and perspective over investment selection alone. Family office services often evolve naturally as advisors respond to increasingly complex client needs. Sustainable organic growth is rooted in trust, which explains why referrals account for the overwhelming majority of Certuity’s new business. Golf and wealth management share the same disciplines: preparation, emotional control, patience, and executing under pressure. The most valuable advisors become trusted partners during life’s defining moments—not simply portfolio managers. Technology continues to reshape wealth management, but experience and wisdom remain difficult to replicate. Building a lasting advisory business requires investing in culture, succession, and the next generation of talent. https://youtu.be/m72Hq6bMTo4 Quotable Moments “The best advisors aren’t simply managing portfolios. They’re the first person clients call when life gets complicated.” “A bad shot in golf is the equivalent of a bad day in the market. You can’t let one dictate everything that comes next.” “More often than not, we’re not just financial advisors—we’re financial therapists.” “Growth gets the headlines. Trust is what makes it possible.” FAQs What is a multi-family office? A multi-family office delivers integrated services beyond investment management, often coordinating tax, estate planning, philanthropy, business planning, and other complex financial matters for affluent families. Why has Certuity grown primarily through referrals? Constantine attributes the firm’s growth to deep client relationships, a collaborative service model, and becoming the trusted advisor clients recommend to others. How does golf relate to wealth management? Golf reinforces discipline, emotional control, preparation, and performing under pressure—all qualities Constantine believes are essential for effective advisors. What is Constantine’s perspective on private equity in wealth management? While he understands why many firms pursue private equity, he believes every strategic decision should ultimately be measured against what best serves clients. What qualities distinguish exceptional advisors today? According to Constantine, exceptional advisors become trusted coordinators of a client’s financial life—bringing together specialists, solving problems, and providing perspective during life’s most important moments. A multi-family office delivers integrated services beyond investment management, often coordinating tax, estate planning, philanthropy, business planning, and other complex financial matters for affluent families. Constantine attributes the firm’s growth to deep client relationships, a collaborative service model, and becoming the trusted advisor clients recommend to others. Golf reinforces discipline, emotional control, preparation, and performing under pressure—all qualities Constantine believes are essential for effective advisors. While he understands why many firms pursue private equity, he believes every strategic decision should ultimately be measured against what best serves clients. According to Constantine, exceptional advisors become trusted coordinators of a client’s financial life—bringing together specialists, solving problems, and providing perspective during life’s most important moments. Related Resources Emotional Intelligence: The “Untouchable” Differentiator in an AI World Intentional Growth: How Top Advisors Build Businesses That Last The 10 Characteristics of the Most Successful Teams Constantine Hatzivassiliou Partner  Constantine Hatzivassiliou is a Partner at Certuity, a nationally recognized multi-family office serving affluent families, entrepreneurs, executives, foundations, and endowments. He advises clients on the complex financial, tax, estate, and business planning decisions that accompany significant wealth, helping families coordinate all aspects of their financial lives through a comprehensive family office approach. Drawing on more than two decades of experience, Constantine works closely with successful business owners, corporate executives, and multi-generational families to simplify financial complexity and align investment management, tax planning, estate planning, philanthropy, and family governance strategies. As a Certified Exit Planning Advisor (CEPA®), he frequently assists entrepreneurs in preparing for liquidity events, business transitions, and the long-term stewardship of family wealth. His clients often view him as a trusted advisor and strategic sounding board, helping them navigate important financial decisions with the perspective of both a family office professional and a coach. Prior to joining Certuity, Constantine held advisory and banking positions with The Bank of New York Mellon, Bernstein Global Wealth Management, and Pacific Mercantile Bank. Before entering the financial services industry, he was a Golf Professional and member of the PGA of America, experiences that continue to shape his disciplined, competitive, and relationship-focused approach to advising clients. Outside of his professional responsibilities, Constantine is passionate about ment

  6. Jul 9

    Emotional Intelligence: The “Untouchable” Differentiator in an AI World

    With James Woodfall, Communication and Behavior Specialist, Raise Your EI As AI makes expertise more accessible, what becomes an advisor’s true advantage? EI expert James Woodfall explains why authentic human connection may be the one thing technology can’t replicate. In Summary As artificial intelligence reshapes how information is delivered, financial advisors are being challenged to rethink what truly differentiates their value. Mindy Diamond sits down with James Woodfall, a former wealth management business owner turned emotional intelligence expert and founder of Raise Your EI, to explore why emotional intelligence may become one of the profession’s greatest competitive advantages. Together, they discuss how rapport, curiosity, and authentic human connection influence trust, referrals, leadership, and client loyalty and why those skills can be developed just like technical expertise. The conversation also examines the difference between AI’s “synthetic empathy” and the authentic relationships clients continue to value—and why that distinction matters to financial advisors now more than ever.   The Storyline For decades, advisors have built successful businesses by combining technical expertise with thoughtful financial guidance. But as AI makes information more accessible and planning tools more sophisticated, expertise alone is becoming less of a differentiator. James Woodfall believes the future belongs to advisors who master something technology cannot authentically replicate: human connection. Drawing on his experience as both a former wealth management firm owner and a specialist in communication and behavioral science, James explains why emotional intelligence isn’t simply a “soft skill.” It’s a business skill that affects nearly every aspect of an advisory practice—from building trust and earning referrals to leading teams and helping clients make difficult decisions. Mindy and James explore why asking better questions matters more than having better answers, how curiosity creates stronger relationships than scripts ever can, and why advisors who create memorable client experiences may find themselves even more valuable in an increasingly automated world. The conversation ultimately reframes AI not as a replacement for advisors, but as a catalyst forcing the profession to rediscover the uniquely human qualities clients have valued all along.   Topics Covered Emotional intelligence as a business skill Building trust through rapport and curiosity Authentic empathy vs. synthetic AI empathy The psychology behind client decision-making Why referrals are rooted in emotional outcomes Coaching advisors to improve communication Leadership and emotional intelligence AI’s impact on advisor differentiation Creating premium client experiences Future-proofing advisory businesses > Download a transcript of this episode… Listen and Learn Highlights for Advisors Why do better questions lead to better financial advice? (6:10) James explains why financial planning is only as good as the conversations that precede it—and why understanding a client’s fears and aspirations leads to better outcomes than simply gathering financial facts. How does emotional intelligence translate into business growth? (15:30) Rapport isn’t simply about making clients feel comfortable. James discusses why advisors who build trust quickly tend to earn more referrals and become significantly more referable. Can emotional intelligence actually be learned? (37:05) Contrary to popular belief, emotional intelligence isn’t an innate personality trait. James explains why it is a trainable skill and how advisors can intentionally improve it throughout their careers. What makes authentic empathy different from AI? (39:10) One of the episode’s most compelling discussions explores the difference between AI’s ability to simulate empathy and the authentic emotional connection that develops between two people. Why should advisors think more about experience than efficiency? (45:10) Clients don’t always pay more for information. Often, they pay more for confidence, judgment, reassurance, and the experience of working with someone they trust. Will AI replace advisors or elevate the best ones? (46:55) James shares why he believes AI is more likely to automate routine work while making relationship-centered advisors even more valuable. Key Takeaways Emotional intelligence is a measurable business capability—not simply a personality trait. Stronger client relationships begin with curiosity rather than advice. Advisors who solve emotional concerns make it easier for clients to recommend than advisors who simply deliver technical expertise. AI may replicate information, but authentic trust remains distinctly human. Premium advisory relationships will increasingly be defined by the experience clients receive—not just the answers they’re given. Emotional intelligence improves leadership, client retention, referrals, and advisor well-being. The firms that embrace both technology and human connection will likely be best positioned for the future. https://youtu.be/xlQMQm6mqtc Quotable Moments “Rapport building is one of the foundational things for trust building.” “It’s not real empathy. It’s synthetic empathy.” “If all of our decisions were made on price, Ferrari wouldn’t have a business.” “The advisors who create authentic human connection may be the ones who remain untouchable.” FAQs What is emotional intelligence, and why does it matter for financial advisors? James defines emotional intelligence as the ability to recognize, understand, and influence emotions in ourselves and others. For advisors, those skills strengthen communication, trust, leadership, and client relationships. Can emotional intelligence actually be developed? Yes. Unlike IQ, emotional intelligence can be improved through intentional practice, feedback, coaching, and greater self-awareness. Why do referrals have so much to do with emotional intelligence? Clients often remember and recommend how an advisor made them feel more than the technical work performed. Solving emotional concerns creates stories clients naturally share with others. What does James mean by “synthetic empathy”? AI can recognize language patterns and respond empathetically, but it doesn’t genuinely experience human emotion. James argues that authentic empathy remains one of an advisor’s greatest competitive advantages. How should advisors think about AI? Rather than viewing AI solely as a competitor, advisors should use it to improve efficiency while investing more time in conversations, judgment, and relationships that technology cannot fully replace. What is the biggest mindset shift advisors should make? Stop viewing emotional intelligence as a soft skill. Treat it as a business skill that directly influences growth, leadership, client loyalty, and long-term differentiation. James defines emotional intelligence as the ability to recognize, understand, and influence emotions in ourselves and others. For advisors, those skills strengthen communication, trust, leadership, and client relationships. Yes. Unlike IQ, emotional intelligence can be improved through intentional practice, feedback, coaching, and greater self-awareness. Clients often remember and recommend how an advisor made them feel more than the technical work performed. Solving emotional concerns creates stories clients naturally share with others. AI can recognize language patterns and respond empathetically, but it doesn’t genuinely experience human emotion. James argues that authentic empathy remains one of an advisor’s greatest competitive advantages. Rather than viewing AI solely as a competitor, advisors should use it to improve efficiency while investing more time in conversations, judgment, and relationships that technology cannot fully replace. Stop viewing emotional intelligence as a soft skill. Treat it as a business skill that directly influences growth, leadership, client loyalty, and long-term differentiation. Related Resources Why AI Matters Now: Filling the Estate Planning Gap with Wealth.com The Paradox of Choice Traps Successful Advisors Freedom vs. Familiarity: Is It Worth Disrupting Comfort for Something That Might Be Better? Guest Bio James Woodfall, founder of Raise Your EI, is a former financial planner who now advises financial services and firms on how they can leverage emotional intelligence (EI) to improve individual and organizational performance. He is the co-author, with Cliff Lansley, of “The Heart of Finance,” which teaches finance professionals to develop the emotional intelligence needed to build effective and profitable client relationships. NOTE: The views and opinions expressed by the guests on this podcast are their own and do not necessarily reflect the views and opinions of Diamond Consultants. Neither Diamond Consultants nor the guests on this podcast are compensated in any way for their participation. View the transcript of this episode… Emotional Intelligence: The “Untouchable” Differentiator in an AI World A conversation with Mindy Diamond and James Woodfall, Communication and Behavior Specialist at Raise Your EI.      Mindy Diamond: Welcome to the latest episode of our podcast series for financial advisors. Today’s episode is Emotional Intelligence: The “Untouchable” Differentiator in an AI World. It’s a conversation with James Woodfall, Communication and Behavior Specialist from Raise Your EI. I’m Mindy Diamond, and this is the Diamond Podcast for Financial Advisors. At Diamond Consultants, we help elite advisors identify the right environment for their businesses to thrive, whe

  7. Jul 2

    The Advisor Transition Playbook: The Latest on Due Diligence, the Move, and Everything In Between – Part 2 – Best of Replay

    A Special Industry Update, With Jason Diamond and Mindy Diamond Jason and Mindy Diamond revisit how advisor due diligence is evolving—from AI and enterprise value to firm stability, ownership, and optionality—and why those questions matter more than ever. In Summary Due diligence has always been about finding the right fit. But what advisors are evaluating has expanded considerably. In this replay of an Industry Update, Jason Diamond and Mindy Diamond revisit The Advisor Transition Playbook to explore how advisor priorities continue to evolve. Beyond the traditional reasons advisors consider change, they discuss newer factors shaping decisions today—from artificial intelligence and enterprise value to ownership structure, firm stability, and long-term optionality. The conversation reinforces that while every advisor’s motivations are personal, the evaluation process has become far more strategic. Today’s advisors aren’t simply comparing recruiting deals or platforms. They’re considering how today’s decisions may influence the value, flexibility, and future of the businesses they’re building. The Storyline For years, advisor movement was largely driven by familiar themes: bureaucracy, management changes, technology frustrations, and the desire for greater independence. Those factors remain important. But the conversations Diamond Consultants has with advisors today increasingly include questions that rarely surfaced just a few years ago. How should AI factor into firm selection? What is the long-term value of building enterprise value instead of simply maximizing a recruiting package? How important is a firm’s ownership structure? And how should advisors think about stability in a marketplace where acquisitions, recapitalizations, and private equity investment have become commonplace? Jason and Mindy revisit the transition framework introduced in Part 1, focusing less on the mechanics of making a move and more on the evolving criteria advisors are using to evaluate their options. The result is a broader discussion about due diligence—not simply as a transition exercise, but as an ongoing strategic process for advisors seeking to build their best business life. Topics Covered Advisor due diligence Traditional vs. emerging drivers of advisor movement Artificial intelligence in wealth management Enterprise value and advisor ownership Recruiting deals versus long-term economics Reverse due diligence Firm ownership and stability Private equity in wealth management Advisor optionality Building a long-term advisory business Blubrry Player > Download a transcript of this episode… Listen and Learn Highlights for Advisors Why are the traditional drivers of advisor movement still relevant? (4:00) Jason and Mindy revisit the longstanding push-and-pull factors that continue to influence advisor decisions, from bureaucracy and management frustrations to the desire for greater ownership and control. How has AI become part of the due diligence process? (13:50) The discussion explores why advisors increasingly expect firms to demonstrate a clear AI strategy—and why investment, integration, and vision may become meaningful competitive advantages. Why should advisors care about enterprise value, even if they don’t technically own their business? (24:30) Jason and Mindy explain why more advisors are evaluating decisions through the lens of long-term business value rather than solely short-term economics. What does reverse due diligence really involve? (37:15) The conversation highlights why advisors should evaluate prospective firms with the same rigor firms use when evaluating advisors. How does firm ownership affect advisor optionality? (38:00) Private equity, acquisitions, and changing ownership structures have made it increasingly important to understand what happens if a firm’s strategy changes after an advisor joins. Why has due diligence become more strategic than ever? (45:30) The episode concludes with a broader discussion about defining one’s “best business life” and making decisions that align with long-term goals rather than reacting to short-term frustrations. Key Takeaways The reasons advisors evaluate change have expanded well beyond traditional frustrations such as bureaucracy and compensation. AI has become an increasingly important component of firm evaluation, not because it replaces advisors, but because it can enhance productivity and client service. Enterprise value is becoming a consideration even for advisors who currently work within employee models. Reverse due diligence is just as important as a firm’s evaluation of an advisor, particularly when assessing ownership structure, capitalization, and long-term stability. The most effective transition decisions balance immediate economics with long-term flexibility, ownership, and optionality. Every advisor’s definition of success is different, making clarity around personal goals the foundation of any due diligence process. https://youtu.be/WZbUZJZK1yc Quotable Moments “Every advisor deserves to live their best business life.” “Just because you’re frustrated doesn’t mean you should move. You need something worth moving toward.” “The question isn’t simply what you’re paid today. It’s what you’re building over time.” “Knowledge is power. Understanding what your business is worth should be part of every advisor’s decision-making process.” FAQs Why are more advisors expanding their due diligence beyond compensation? While transition economics remain important, advisors are increasingly evaluating technology, AI capabilities, enterprise value, ownership opportunities, and long-term flexibility as part of the decision-making process. How should advisors evaluate a firm’s AI strategy? Rather than looking for finished products, advisors should assess whether a firm has a clear vision, meaningful investment, and an integrated approach to using AI to improve advisor productivity and client experience. What is reverse due diligence? Reverse due diligence is the process of evaluating a prospective firm as thoroughly as the firm evaluates the advisor. It includes understanding ownership structure, financial stability, culture, technology, leadership, and long-term strategy. Why does enterprise value matter for employee advisors? Even advisors who do not currently own their businesses may benefit from understanding how different business models create opportunities for ownership, long-term value creation, and future monetization. How has private equity changed advisor due diligence? Private equity has introduced new opportunities for growth and capital, but it has also made it more important for advisors to understand ownership structures, investment horizons, and what future transactions could mean for their business. What does Diamond Consultants mean by an advisor’s “best business life”? It refers to aligning an advisor’s business model, goals, client experience, compensation, flexibility, and long-term vision in a way that best supports both the advisor and the clients they serve. While transition economics remain important, advisors are increasingly evaluating technology, AI capabilities, enterprise value, ownership opportunities, and long-term flexibility as part of the decision-making process. Rather than looking for finished products, advisors should assess whether a firm has a clear vision, meaningful investment, and an integrated approach to using AI to improve advisor productivity and client experience. Reverse due diligence is the process of evaluating a prospective firm as thoroughly as the firm evaluates the advisor. It includes understanding ownership structure, financial stability, culture, technology, leadership, and long-term strategy. Even advisors who do not currently own their businesses may benefit from understanding how different business models create opportunities for ownership, long-term value creation, and future monetization. Private equity has introduced new opportunities for growth and capital, but it has also made it more important for advisors to understand ownership structures, investment horizons, and what future transactions could mean for their business. It refers to aligning an advisor’s business model, goals, client experience, compensation, flexibility, and long-term vision in a way that best supports both the advisor and the clients they serve. NOTE: The views and opinions expressed by the guests on this podcast are their own and do not necessarily reflect the views and opinions of Diamond Consultants. Neither Diamond Consultants nor the guests on this podcast are compensated in any way for their participation. Related Resources The Advisor Transition Playbook: The Latest on Due Diligence, the Move, and Everything In Between – Part 1 Annual Advisor Transition Report Top 10 Tips for a Strategic Due Diligence Process Should I Stay or Should I Go? View the transcript of this episode… The Advisor Transition Playbook: The Latest on Due Diligence, the Move, and Everything In Between – Part 2 A Special Industry Update with Jason Diamond and Mindy Diamond. Jason Diamond: Welcome to a replay of one of the most popular episodes from our podcast series for financial advisors, The Advisor Transition Playbook: The Latest on Due Diligence, the Move, and Everything In Between. It’s Part 2 of a 2-Part Industry Update with Mindy Diamond. I’m Jason Diamond and this is the Diamond Podcast for Financial Advisors. Mindy Diamond: At Diamond Consultants, we help elite advisors identify the right environment for their businesses to thrive, whether that’s at a wirehouse, boutique, or independent firm. With nearly three decades of

  8. Jun 25

    Build, Grow & Transact: Americana’s $12B Path from Breakaway to Enterprise

    Jason Fertitta – CEO & Partner, Americana Partners Jason Fertitta shares how Americana Partners grew from a $2.6B breakaway team to a $13B+ enterprise by focusing on ownership, enterprise value, strategic acquisitions, and long-term growth. In Summary Many advisors view independence as the ultimate objective: a chance to gain control, improve economics, and build a business on their own terms. For Jason Fertitta, independence was only the beginning. Louis Diamond speaks with the CEO and Founding Partner of Americana Partners about the firm’s evolution from a $2.6 billion breakaway team in 2019 to a national enterprise managing more than $13 billion today. The conversation explores the decisions that fueled that growth, the mindset required to build long-term enterprise value, and why Jason believes advisors should evaluate success through the lens of net worth rather than annual income. Along the way, they discuss recruiting, acquisitions, private equity, professional management, and the tradeoffs that come with building something intended to outlast its founders. The Storyline The independent channel has matured. A decade ago, many advisors pursued independence primarily for greater autonomy, higher payouts, and control over the client experience. Today, a growing number are approaching the decision differently—viewing independence as a platform for building enterprise value, attracting capital, completing acquisitions, and creating businesses that can scale beyond the founders themselves. Jason Fertitta’s journey reflects that evolution. When he and his partners left Morgan Stanley in 2019, Americana launched with approximately $2.6B in client assets and a vision to build a nationally recognized wealth management firm. Seven years later, the firm oversees more than $13B, employs roughly 100 people, operates across multiple markets, has completed several acquisitions, and brought on Lovell Minnick Partners as its first institutional investor. Throughout the conversation, Jason offers a transparent look at the realities of enterprise building. That includes reinvesting profits rather than maximizing income, hiring professional management long before it feels necessary, embracing acquisitions as a growth strategy, and making decisions based on long-term value creation rather than short-term economics. For advisors considering what comes after independence, the episode provides a practical framework for thinking about ownership, scale, capital, and the future value of their business. About the Build, Grow & Transact Series for Advisors Build, Grow & Transact explores what happens after independence. The series features advisors and firm leaders who viewed independence not as a destination, but as the foundation for building something larger. Some launched firms from scratch. Others scaled through recruiting, acquisitions, or strategic partnerships. Many eventually faced decisions around capital, ownership, succession, or liquidity. While every story is different, they share a common thread: a willingness to think beyond the transition itself and focus on creating long-term enterprise value. Through candid conversations with founders, builders, and industry leaders, the series examines the decisions, tradeoffs, and lessons that come with growing an advisory business into an enduring enterprise. For advisors contemplating independence, actively building a firm, or considering what comes next, Build, Grow & Transact offers a look at the paths others have taken—and what they’ve learned along the way. > Download a transcript of this episode… Listen and Learn Highlights for Advisors Why did Americana grow from $2.6 billion to more than $13 billion? (06:16) Jason explains how a combination of organic growth, advisor recruiting, acquisitions, and long-term strategic planning helped accelerate the firm’s expansion. Why do clients often do more business with independent advisors? (12:17) Jason shares his perspective on why clients frequently deepen relationships after an advisor leaves a wirehouse environment. What role have alternatives played in Americana’s growth strategy? (14:40) The discussion explores how differentiated investment access can help advisors stand apart in an increasingly commoditized marketplace. When is it time to build a professional management team? (18:36) Jason explains why Americana invested heavily in leadership, operations, and infrastructure from the very beginning. Why did Americana bring in private equity capital? (25:16) A candid discussion about growth capital, M&A opportunities, and the decision to partner with Lovell Minnick Partners. How do you evaluate enterprise value versus annual income? (20:16) Jason offers one of the episode’s most important lessons: building wealth through ownership can look very different than maximizing current compensation. What makes a successful acquisition target? (39:51) Jason outlines how Americana evaluates M&A opportunities and how acquisitions fit into the broader client experience. Is it better to build your own firm or join an existing platform? (45:40) The conversation closes with Jason’s perspective on the trade-offs between launching independently and joining a scaled independent enterprise. Topics Covered Enterprise value creation Independence and ownership Organic growth strategies Advisor recruiting RIA acquisitions Private equity partnerships Professional management teams Alternative investments Family office services Building a national wealth management firm Key Takeaways Independence can be a starting point for building an enterprise rather than the final objective. Long-term wealth creation often stems from ownership and equity appreciation, not from maximizing annual income. Reinvesting profits into leadership, infrastructure, and talent can accelerate enterprise value. Organic growth and acquisitions can complement one another when supported by a clear strategy. Outside capital can be a growth catalyst when aligned with management’s long-term vision. The most scalable firms are often built around client needs rather than predefined acquisition targets. Advisors have more options than ever before, ranging from building independently to joining established platforms. https://youtu.be/_12jZJFsi4U Quotable Moments “Even to this day, I don’t make anywhere near the amount of income that I made when I was on Wall Street. But my net worth is up tenfold.” “If you want to create value for yourself and your partners and grow your balance sheet, you can do it in a much more tax-efficient way in the independent world.” “I’ve never thought about how much of the company I own. I’ve thought about what my slice is worth.” “We want to build something our children would be proud to say we helped create.” FAQs Why are more advisors viewing independence as a business-building opportunity? The independent channel increasingly offers opportunities to create enterprise value, pursue acquisitions, attract capital, and build scalable businesses beyond a traditional advisory practice. How can advisors increase the enterprise value of their firms? Enterprise value is often driven by factors such as growth, profitability, leadership depth, recurring revenue, client demographics, infrastructure, and scalability. What role does private equity play in wealth management firms? Private equity can provide capital, strategic guidance, operational expertise, and acquisition support while helping firms accelerate growth initiatives. How do RIAs use acquisitions to grow? Many firms use acquisitions to expand geographically, add specialized capabilities, deepen client services, and accelerate asset growth. Why are professional management teams becoming more common among RIAs? As firms scale, dedicated leadership across operations, finance, compliance, and business management enables advisors to focus more effectively on clients and growth. Is launching an independent firm always the best path? Not necessarily. Some advisors prefer to build their own enterprise, while others may achieve their goals more effectively by joining an established independent platform that already provides scale and infrastructure. The independent channel increasingly offers opportunities to create enterprise value, pursue acquisitions, attract capital, and build scalable businesses beyond a traditional advisory practice. Enterprise value is often driven by factors such as growth, profitability, leadership depth, recurring revenue, client demographics, infrastructure, and scalability. Private equity can provide capital, strategic guidance, operational expertise, and acquisition support while helping firms accelerate growth initiatives. Many firms use acquisitions to expand geographically, add specialized capabilities, deepen client services, and accelerate asset growth. As firms scale, dedicated leadership across operations, finance, compliance, and business management enables advisors to focus more effectively on clients and growth. Not necessarily. Some advisors prefer to build their own enterprise, while others may achieve their goals more effectively by joining an established independent platform that already provides scale and infrastructure. Related Resources From Ex-Morgan Stanley Advisor to One of the Biggest Breakaway Stories of 2019 with Jason Fertitta (Podcast Episode) Intentional Growth: How Top Advisors Build Businesses That Last (Article) M&A Readiness Assessment (Tool) Guest Bio Jason Fertitta Jason is currently Chief Executive Officer / Founding Partner of Americana Partners. Jason was a Managing Director in Morgan Stanley’s Private Wealth Division for eleven years. He joined Morgan Stanley in 2008 after six years with Lehma

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About

Launched in 2017 as Mindy Diamond on Independence, the show has taken on a broader perspective beyond the independent space to include topics, insights, and candid conversations around financial advisor transitions, growth, and an ever-changing industry landscape. Each episode is designed to offer objective guidance and actionable advice with some of the industry’s brightest movers and shakers.

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