Skydeck is a Chicago-based venture capital firm investing across the United States, primarily in Seed and Series A companies, with additional later-stage co-investment activity. It targets businesses with diverse, high-growth revenue streams, strong management teams, and alignment with reputable lead investors. Initial checks are typically $750K to $2M, with follow-on capacity. Its portfolio and investment activity span AI and machine learning, education, fintech, enterprise software, logistics, marketplaces, SaaS, supply chain, transportation, energy, and manufacturing.