Pennington Partners & Co

Pennington Partners & Co

Pennington Partners & Co was founded in 2016 by Brian Gaister and Rodd Macklin, two operators who exited privately held companies and real estate ventures before building a multi-family office designed around founders, CEOs, and multi-generational families. The firm emerged from the thesis that entrepreneurial wealth creators need an investment partner who has navigated the same liquidity, tax, and governance challenges — not a generic private bank. Gaister concurrently leads the affiliated venture platform SaaS Ventures and the real estate development firm PTM Partners, embedding operating-company DNA into the family office. The firm deploys across private equity, venture capital, real estate, and private credit, blending direct co-investments and SPVs with fund-of-funds commitments. Confirmed portfolio holdings span early-stage to buyout: the firm reports positions in the iShares Bitcoin Trust and iShares Ethereum Trust, while Gaister’s SaaS Ventures arm backs early-stage enterprise software and cybersecurity companies. Real estate investments, often executed through joint ventures, include the mixed-use Soleste Grand Central in Miami, 2000 Biscayne Boulevard with Kushner Companies, Edge Collective in St. Petersburg, and the Watermark project in Washington, DC. Geographic focus covers North America, Europe, Asia, and the Middle East & Central Asia. Pennington Partners won the Family Wealth Report Award in 2023 for Best Multi-Family Office up to $2.5 billion in AUM/AUA, an acknowledgement of its traction with founder-led families. The firm operates from Bethesda and a secondary office in Houston. Beyond the core MFO, Gaister maintains active roles in YPO and the Jewish Federation National Young Leadership Cabinet and serves on the investment committee of the Bender JCC of Greater Washington, signaling institutional connectivity rather than passive membership. The firm’s platform includes a tax-advantaged alternative income program called PPA, complementing the core family-office operating partnership. The structural differentiator is the operating-company layer: Pennington Partners is not merely a wealth allocator but a co-investor that originates deals through its own development and venture entities, then syndicates them internally. This hybrid architecture — part family office, part GP — lets founder-clients invest alongside principals who have their own capital in every deal, creating an alignment mechanism that pure-fee MFOs cannot replicate. The firm’s continued development of large-scale ground-up projects in Florida and the Mid-Atlantic reinforces that it behaves more like an owner-operator than a consultant.