Upheaval Investments

Riley Florsheim serves as Co-founder and Chief Investment Officer, leading investment decisions. His brother Steven Florsheim is Co-founder and Principal Owner. The daily division of responsibilities between the two brothers is not publicly detailed, but the concentrated leadership structure suggests decisions remain closely held rather than committee-driven.

Steven Florsheim is a member of the family that founded and built the Florsheim Shoe Company, one of America's historic footwear manufacturers. The wealth generated from that enterprise provides the capital base for Upheaval Investments. The firm operates independently of the original shoe company, which has changed corporate ownership multiple times.

All available evidence points to a proprietary capital structure. The firm has no publicly listed funds, no SEC filings as a registered investment advisor, and no investor relations presence. A business relationship with Lawrence Levy of Levy Family Partners suggests occasional co-investment with other families, but Upheaval itself does not appear to accept third-party limited partners.

The firm maintains a developed blockchain and crypto portfolio, though specific holdings, custody arrangements, and entry points are not publicly disclosed. The presence of a meaningful allocation alongside traditional real estate assets indicates a deliberate digital-asset strategy rather than passive exposure.

Known holdings include The Redbury South Beach, a commercial property in Miami Beach, Florida, and Esperanza Resort in Cabo San Lucas, Mexico. The cross-border nature of the resort investment demonstrates willingness to operate internationally. No additional properties or total real estate portfolio valuation have been disclosed.

Yes. Steven Florsheim is a member of YPO Chicagoland, a chapter of the Young Presidents Organization that connects chief executives and principal investors. For family offices and closely held investment firms, YPO chapters frequently function as deal-sourcing networks, offering direct access to other business owners seeking capital or partnership. It is reasonable to infer that part of Upheaval's venture pipeline originates through these relationships.

The Florsheim family, including Jennifer Friedes, supports several Chicago-based organizations: College Possible, which focuses on college access for low-income students; PAWS Chicago, a no-kill animal shelter; and Steppenwolf Theatre Company, the Tony Award-winning ensemble theater. These appear to reflect personal and local civic commitments rather than a formal, firm-branded foundation.