How One Founder is Transforming Family Offices and Expanding Innovation Through Multiple Ventures

Family offices are undergoing a profound transformation. Families of substantial wealth are choosing direct investments, giving them greater control and cost savings over traditional investment models. This transition, however, brings unique challenges, especially for families seeking to manage wealth while balancing an array of financial, social, and legacy-oriented goals. 

One entrepreneur taking a unique approach to meet these needs is Brian Gaister, cofounder of Pennington Partners & Co., SaaS Ventures, and PTM Partners. Through his companies, Gaister is reshaping wealth management for families by building integrated platforms that offer highly specialized financial administration, investment opportunities, and strategic advisory services.

A Holistic Approach to Family Wealth Management

Gaister’s inspiration for Pennington Partners began with his own family’s experiences and his career advising ultra-high-net-worth families. 

Family offices often need more than a traditional investment advisor can offer.

He explains. 

With his cofounder, Rodd Macklin, he created Pennington Partners in 2016 to address the nuanced needs of families with significant wealth by combining financial oversight, personal wealth services, and collaborative investment opportunities into a single platform. They designed the firm around three core pillars, each addressing specific aspects of family office management and financial growth.

1. Household Financial Administration Services

Pennington’s first pillar is a comprehensive financial administration service, which provides families with everything from complex partnership accounting to personal bookkeeping and medical claims management. Gaister notes that families often have a variety of financial advisors and investments, making centralized oversight crucial. The firm’s tools allow families to track all their investments and expenditures from a single dashboard, offering clear insights into cash flow and investment performance. By handling personal bookkeeping and bill payment, Pennington enables its clients to focus on higher-level decisions while gaining a full understanding of their financial position.

2. A Bespoke Multi-Family Office

The second pillar of Pennington Partners is a bespoke multi-family office, designed for founders, CEOs, and high-net-worth families. Pennington provides an alternative to “one-size-fits-all” investment models, which can often feel limited for families with complex asset portfolios and distinct needs. Unlike traditional advisory services, Pennington fosters deep partnerships with its clients, working alongside them to craft strategies that align with their goals and values. The firm’s collaborative model—similar to Michael Dell’s private investment office, MSD Capital—creates mutual benefits for multiple entrepreneurial families under one umbrella, maximizing expertise and shared investment opportunities.

3. Tax-Advantaged Alternative Investment Platform

Gaister’s third pillar addresses a rising demand for tax-advantaged and alternative investment opportunities. This platform provides access to venture capital, real estate in opportunity zones, and income-generating investments with tax benefits, allowing families to grow wealth efficiently. Pennington’s portfolio includes investments across sectors such as software, logistics, and ESG (environmental, social, and governance) technology. By focusing on these sectors, Pennington ensures that their clients have access to meaningful opportunities with both economic and social impact, an aspect that Gaister and his clients highly value.

Investing in Innovation with SaaS Ventures

Gaister’s work extends beyond Pennington Partners through SaaS Ventures, a venture capital firm specializing in early-stage software companies located in undercapitalized, second- and third-tier U.S. cities. By investing in regions often overlooked by traditional venture capital, SaaS Ventures aims to uncover innovative tech solutions at lower valuations, benefiting both the companies and investors. SaaS Ventures focuses on e-commerce, logistics, cybersecurity, and ESG tech—industries where Gaister sees transformative potential.

Creating Social Impact with PTM Partners

Through PTM Partners, Gaister bridges the gap between real estate investment and social responsibility. PTM specializes in opportunity zone projects that align with government efforts to revitalize underserved areas. By identifying properties in growth-focused regions, PTM delivers economic returns while fostering meaningful community development. For Gaister, these investments reflect a broader commitment to balancing wealth creation with positive societal impact.

Shaping the Future Workforce

Gaister is deeply committed to addressing the workforce challenges of the future. Through organizations like Catalyte and Genesys Works, he supports initiatives that provide underserved populations with skills training and job opportunities in technology. Catalyte trains individuals from diverse backgrounds to become developers, placing them on new career trajectories, while Genesys Works offers high school students internships that often lead to high-paying jobs post-college. “Empowering people with new skills will drive productivity and inclusiveness in the digital age,” Gaister asserts.

A Legacy of Purpose and Innovation

Gaister’s endeavors stem from a personal passion for helping others, a commitment he developed as a member of an entrepreneurial family. Active in the Jewish Federation’s National Young Leadership Cabinet and a supporter of initiatives like the United States Holocaust Memorial Museum, he connects deeply with the value of tikkun olam—repairing the world.

His investments, both financial and personal, represent a forward-thinking model that integrates wealth management, business innovation, and social responsibility. As he continues to expand Pennington Partners, SaaS Ventures, and PTM Partners, Gaister’s work serves as a powerful example of how successful entrepreneurs can use their resources and vision to create lasting, positive change for generations to come.