On May 8, 2025, the CFA Society Chicago welcomed Stacy Devine, CFA, Gil Calderon, CFA, and Lauren Bugay, CFA as a part of The Vault Series to discuss Family Office investing. Stacy, Gil, and Lauren shared insights into their career paths and the unique nature of family office investing. The discussion highlighted the evolving relevance of CFA charterholders in private wealth management, particularly in single and multi-family office settings. Each panelist brought a distinct perspective, having transitioned from traditional finance roles to family offices where they now lead or support complex, multi-asset investment portfolios.
Stacy Devine, Chief Investment Officer at RPTC, detailed her path from public accounting and sell-side equity research to the single family office space. She earned the CFA charter while taking a career break which broadened her perspective and skill set for the investment industry. This also enabled her to shift from public equities to full asset class coverage, eventually leading to managing investments for a single family office. She emphasized the many responsibilities of the role across the firm beyond investing, such as operations. She pushed for strong infrastructure early — citing the implementation of Addepar as a critical project when she joined RPTC.
Gil Calderon, Chief Investment Officer at Five11 Partners, recounted his journey from leveraged finance at CIBC, followed by a serendipitous entry into the family office space during the 2008 financial crisis. He had planned to pursue an MBA, but instead, he hesitantly accepted an opportunity to join a family office. Despite his initial apprehension for an unfamiliar industry, he turned it into a successful career path. Shortly after joining, Gil’s manager encouraged him to earn the CFA charter, which equipped him with the necessary skills to thrive in the versatile family office environment. After nearly 16 years with two single family offices, he transitioned to Five11 Partners, a multi-family office that aims to offer institutional-quality investments and a single point of contact for ultra-high-net-worth clients frustrated with fragmented service models.
Lauren Bugay, Managing Director at Duchossois Capital Management, shared her career progression from investment banking at William Blair to working directly with the Duchossois single family office, initially in an M&A role for one of their operating businesses. In 2012, after the family sold most of its businesses, she helped transition the enterprise into a formal investment firm. Her decision to pursue the CFA charter was driven by a desire to better manage the public equities side of their portfolio. Today, Lauren oversees both public and private equity, and she reflected on how building the family office from scratch involved significant strategic planning and talent alignment.
A key theme across the panel was the personalized and flexible nature of family office work. Unlike traditional institutional investment roles, family offices offer the chance to engage across all asset classes, influence strategy from the ground up, and build deep relationships with a small group of stakeholders. The panelists underscored that every family office is different—some operate like private equity firms, others like multifaceted family service providers, but all require high-level investment acumen, discretion, and adaptability.
This panel discussion reinforced the growing importance of the CFA charter outside of traditional asset management. With the expansion of private wealth and the increasing complexity of managing multi-generational capital, family offices offer rewarding, intellectually rich career paths for CFA charterholders. Whether in single or multi-family setups, the family office space is proving to be a dynamic and fulfilling arena for those interested in investment strategy, wealth stewardship, and holistic client service.
The discussion centered around the evolving and increasingly significant role of family offices within the investment landscape — particularly in regions like Chicago, where there are more than 50 such offices each managing over $1 billion in assets. The moderator highlighted the growing relevance of these entities for CFA charterholders and young professionals seeking meaningful careers, citing rising academic interest and initiatives like University of Chicago Booth’s new “Family Office” course. As the industry grows, there’s a push to explore family office operations in more depth, with an emphasis on transparency, investment strategy, and team structure.
The panel then gave the audience a glimpse of their respective roles and firms. Lauren provided insight into a family office that maintains a 100% equity allocation, equally split between public and private investments. On the private side, her office participates in venture, growth equity, and buyout funds, while also engaging in direct co-investments. Public equities are actively managed, supplemented by a small portion of passive index funds to maintain balance and liquidity. The strategy is intentionally risk-on, built to preserve and grow multi-generational wealth. Transparency, both internally and externally, is emphasized as key to forming strong relationships with other family offices and investment partners.
Gil brings a multi-family office perspective, emphasizing how unique each family office is in its investment preferences and constraints. His experiences span from highly diversified portfolios to offices that deliberately exclude certain asset classes, like venture capital or private equity, based on the founder’s background or existing exposures. The approach is highly customized—some families seek to maintain wealth conservatively, while others have a higher tolerance for risk. Gil highlighted how the investment process for each family office is deeply personal, emotional, and often driven by practical considerations, like liquidity needs and prior industry ties.
Stacy elaborated on the complexities of managing portfolios for families with significant operating businesses and legacy assets, like sports teams or concentrated stock holdings. Her office employs a predominantly passive strategy for public equities, aligning with their belief in efficient markets, while leveraging internal deal flow for direct private investments. Like Lauren and Gil, she emphasized the lean staffing typical in family offices, which forces CIOs and investment professionals to be highly hands-on.
Th panel emphasized that the culture within family offices is critical—turnover is rare, and hiring is often relationship-based. The shared sentiment across all panelists is that despite the high level of assets, most family offices operate with small, tightly-knit teams, making agility and deep portfolio knowledge essential.
The panel addressed the challenge of keeping up with fast-moving geopolitical, technological, and macroeconomic trends—despite operating lean teams. Gil highlighted that staying informed requires constant reading, consuming financial media, and leaning on his network to help digest complex global developments. The generational divide around assets like cryptocurrency was discussed as a common tension, with younger family members often favoring new asset classes while older generations remain skeptical. Gil emphasized adapting to each family member’s preferences through education and tailored exposure. Stacy added that successful family office professionals must love to learn, be able to separate signal from noise, and proactively respond generational trends such as blockchain. Lauren stressed the importance of leveraging her network to quickly gain insights on investment opportunities, while maintaining a disciplined, long-term approach rather than chasing trends.
When asked about resources and tools, panelists acknowledged a hybrid approach. Lauren mentioned that while their family office ensures adequate resourcing, they take a pragmatic approach, relying on both legacy systems and newer tools like AI where appropriate. Stacy, who came from a banking background, shared how she relies on her professional network for quick answers. The panelists agreed that despite managing lean organizations, they will add tools where necessary to stay informed.
In discussing family office dynamics and advice for younger professionals entering the field, Gil emphasized the importance of understanding each client’s true investment personality—often uncovering mismatches between how families describe their investments and how they have actually invested. This introspective discovery is crucial to building portfolios aligned with real risk tolerance. Family dynamics deeply influence investment strategies, especially under stress, like during market crashes. For younger professionals, the panelists recommended seeking family offices with mentorship, transparency, and a collaborative environment where they can learn broadly—not just about investments, but also about behavioral finance and long-term planning. They also highlighted culture fit being essential, as openings are rare and usually filled through trusted networks.