Second Mountain Financial

Second Mountain Financial

Michael Sonnenfeldt founded Second Mountain Financial in 2020 after two decades of convening wealthy entrepreneurs through Tiger 21, the members-only peer network he established in 1999. The firm traces its capital base to Sonnenfeldt's own liquidity event from the sale of Emmes & Company, a distressed real estate investment firm, and the deep trust of Tiger 21's 1,000-plus members. Second Mountain operates as a deal-by-deal investment platform rather than a traditional blind-pool fund, allowing participants to opt in to individual opportunities vetted by Sonnenfeldt and his team. The firm structures direct investments across a narrow set of asset classes: commercial real estate, energy transition infrastructure, private credit, and secondary-market special situations. Unlike a broad-scope family office, Second Mountain functions as a curated co-investment vehicle where Tiger 21 members — and select outside investors — access deals typically reserved for institutional players. Known commitments include multifamily and industrial real estate acquisitions in secondary US markets, alongside targeted renewable energy project finance. Sonnenfeldt has publicly emphasized climate investing as a core thematic pillar, aligning the platform with the Environmental, Social & Governance priorities common among Tiger 21's membership base. Second Mountain's investment committee draws on the operating experience of serial entrepreneurs who sit within Tiger 21's network, creating a de facto sourcing funnel that originates deal flow from member-owned businesses. The platform maintains its primary presence in New York and does not publicly disclose aggregate committed capital. Sonnenfeldt remains the public face of investment decisions, supported by a lean team that leverages Tiger 21's operational infrastructure without commingling membership dues and investment activities. The firm's structural differentiator is its origination model: Second Mountain accesses proprietary deal flow through a gated community of 1,000-plus ultra-high-net-worth individuals — a model that most investment platforms try but few achieve at scale. Sonnenfeldt has structured succession around a partnership of senior Tiger 21 members rather than a traditional family-office trust architecture, keeping the platform aligned with active wealth creators rather than passive inheritors.