Lofty Ventures

Lofty Ventures is a Chicago-based angel investment community and micro venture fund founded in 2014 by Christopher Deutsch and Spencer Gordon-Sand. The firm describes itself as a convergence of Chicago's best founders and resources, investing at pre-seed and seed stages in startups primarily based in the city. With a four-person team writing checks of $10,000 to $100,000, with a sweet spot of $25,000, Lofty operates at a scale designed to catalyze first rounds for nascent Chicago companies while maintaining a strong focus on supporting underrepresented founders. The firm has participated in approximately 11 tracked portfolio deals across software, SaaS, consumer goods, and healthtech sectors. The standout exit is Cubii, a maker of portable seated fitness devices, which was acquired by Gridiron Capital for a reported $100 million — the fund's most significant return to date. SHYFT Power Solutions exited in November 2024. Other portfolio companies include Gather Voices, WeCasa, UpKey, Bridge Money, Paladin, 4Degrees, Resonado, Arvist, and PairUp, the fund's most recent investment from July 2024. Beyond writing checks, Lofty runs active community programming for its portfolio, including founder dinners and the Women of Lofty initiative, reflecting the firm's emphasis on community building as a competitive advantage. While operating at angel and micro-VC scale, Lofty has carved a distinctive niche as one of Chicago's most community-oriented early-stage investment groups, helping build the city's next generation of technology companies through both capital and sustained founder relationships.