Rob Chesney
US & Canada (North American HQ'd, domiciled teams); Chicago HQ
$500,000 - $2,000,000
Chicago Ventures gives founders better odds by backing builders in industries others overlook, on the belief that enduring companies can be built anywhere, by anyone. The firm leads pre-seed and seed rounds before it's obvious -- typical first check $500K-$2M targeting 10%+ ownership at first close -- takes board seats, and acts as an active, operationally-involved partner from day one, with high-conviction fast decisions and hands-on talent, customer, and follow-on introductions after the check clears. Generalist by mandate, it has its deepest pattern recognition in fintech, supply chain, healthcare, construction, and legal tech. For founder matching, CV is strongest for North American founders in overlooked or unglamorous markets -- especially vertical SaaS in industrial and regulated niches -- with earned grit and inside-out market insight, who genuinely want an involved lead with a board seat rather than passive capital.
