S Squared Technology

Ken Squire, the firm's founder, serves as portfolio manager with final authority over all position sizing and portfolio construction. Squire developed his analytical approach as a technology analyst at Gotham Capital under Bill Ackman. Co-portfolio manager Steve Somers supports research generation and portfolio monitoring.

The firm's idea generation is rooted in a private-market diligence framework applied to public equities. Squire evaluates companies by mapping competitive moats, total addressable market, and founder-led governance structures rather than quarterly earnings momentum. The concentrated 15–25 name portfolio reflects a bottom-up process where each position must survive an extended research cycle.

The firm invests exclusively in publicly traded equities, but it approaches each holding as if underwriting a late-stage venture round. The average holding period exceeds three years, consistent with a permanent-capital mindset rather than a trading-oriented strategy.

The strategy spans enterprise software, artificial intelligence and machine learning, digital health, and financial technology. The firm avoids sectors where innovation cycles are driven by commodity pricing or regulatory approval rather than product velocity and market adoption.

S Squared operates as an investment partnership — structurally a hedge fund — but its permanent-capital posture and concentrated, low-turnover book blur the line between a traditional long/short fund and an innovation-focused holding company. The firm does not market to institutional allocators and maintains minimal public disclosure.

High-conviction positions can exceed 10% of the portfolio when the research supports an outsized allocation. The deliberate concentration — typically 15–25 names — means sector and single-stock risk is an intended feature of the strategy, managed through deep fundamental work rather than broad diversification.

The firm manages capital for a tight group of partners and high-net-worth individuals rather than institutional fund flows. Without a need to market quarterly performance or compete for public pension mandates, Squire invests in staying below the radar and letting the portfolio speak through long-term compounding.