Chicago Ventures

Chicago Ventures Research Investment Thesis Chicago Ventures is a seed-stage venture capital firm founded in 2011 and headquartered in Chicago, Illinois. Their core thesis is captured succinctly in their tagline: "We lead, early." They believe that enduring companies can be built anywhere, by anyone — not just in Silicon Valley — and they focus on founders and industries that are overlooked by coastal investors. Chicago Ventures serves as operationally-involved partners during a company's earliest days. They prefer to be the first institutional investor and take an active, hands-on role alongside founders during the most critical phase of company building. Their investment philosophy centers on high-conviction bets in underestimated teams building in markets they understand deeply. Sector Focus Chicago Ventures invests across several interconnected verticals, with particular depth in: Healthcare and Digital Health: One of their largest portfolio concentrations includes HealthJoy, NOCD, Andros, Rise Science, Dina (care coordination), PulseData (value-based care analytics), Visibly (online vision testing), Wider Circle, and Hint Health. They have a long track record backing digital health innovation. Fintech and Payments: The firm has backed AeroPay (contactless bank-to-bank payments), Sunbit (a unicorn doing point-of-sale financing), Meritize (education lending), M1 Finance (investment platform, IPO), FranShares, Lucro, BlueTape (construction material financing), and InstaSwitch. Supply Chain and Logistics: A major focus area including Project44 (a unicorn providing supply chain visibility), CognitOps (warehouse automation), GoodShip (freight orchestration), OneRail (final-mile delivery), ShipTrac, and Leverage. Enterprise Software: G2 (the software marketplace), GAN Integrity (compliance management), Savvi AI, Chowly (restaurant POS integration), and many vertical SaaS tools. Legal and RegTech: A growing focus area with ILS (Intelligent Legal Solutions — fund automation for lawyers) and Entegrata (Azure lakehouse for the legal industry). Industrial Tech and Construction: GreenLite (AI-powered construction permitting), BuildForce, Part3, and LandscapeHub. Consumer Media: Cameo (personalized video platform), Pluto TV (exit, acquired by Viacom/Paramount), and Protégé. Proptech: Prefix (home maintenance), Kin (homeowners insurance), SpotHero (parking, exit), and Promenade. Stage Focus Chicago Ventures focuses primarily on Seed-stage investments, consistent with their brand positioning as "We lead, early." They occasionally follow on into Series A for their top performers. With $80M raised across Fund IV and the Opportunity Fund (closed November 2024), they have fresh capital actively deploying into early-stage companies. Check Size Based on portfolio analysis and Tracxn data, Chicago Ventures typically invests: Seed: $500K–$5M (average seed round ~$2.85M) They target meaningful ownership as lead investors at the seed stage Lead Tendency Chicago Ventures consistently positions itself as a lead investor. Their branding explicitly says "We lead, early" and their history shows them leading seed rounds across the portfolio. They co-led Annie's $4M seed with Las Olas VC (November 2025) and led the $3M+ seed round for ILS (March 2026). Recent Activity Chicago Ventures closed Fund IV and the CV Opportunity Fund for a combined $80M in November 2024, signaling active deployment capacity. Recent investments include: March 2026: Led $3M+ seed round in ILS (Intelligent Legal Solutions) — AI-powered software for investment fund lawyers, automating side letter management and MFN processes November 2025: Co-led $4M seed round in Annie — AI coworker platform for dental practices, co-leading alongside Las Olas VC September 2025: Participated in GreenLite's $49.5M Series B (portfolio follow-on) — AI-powered construction permitting, led by Insight Partners Portfolio Highlights Unicorns: Project44 (supply chain visibility), Sunbit (point-of-sale financing), and others totaling 7 unicorns from the portfolio Exits: 29 acquisitions including Pluto TV (acquired by Viacom/Paramount), Tock (acquired by Squarespace), and Cameo still active. SpotHero, Data.world, Shiftgig, Catalytic, and many others have also exited. IPO: M1 Finance went public as a portfolio company. Active growth-stage companies: G2, Telnyx, ZenBusiness, Kin Insurance, AeroPay, NOCD, HealthJoy. Team Chicago Ventures operates with a tight partnership model: Stuart Larkins, Partner: Key figure in the firm's operations, editor of Chicago Ventures Medium publication Rob Chesney, Partner: Partner driving investment decisions Eric Duboe, Partner: Promoted to Partner, focuses on evaluating seed-stage enterprise software investment opportunities and providing portfolio support Lindsay Knight, Partner: Partner and co-editor of Chicago Ventures content/thesis writing Kevin Willer, Venture Partner: Former Google for Startups lead, brings deep Chicago ecosystem connections Ford Johnstone, Associate: Early-stage sourcing and diligence Emma Lawler, Entrepreneur in Residence: Operator-in-residence supporting portfolio Geographic Focus Chicago Ventures was founded on the premise that great companies can be built outside Silicon Valley. They invest across 20+ cities, with a particular emphasis on the Midwest and underserved startup ecosystems. Their portfolio spans Chicago, Utah, Southeast, and beyond — with a notable recent investment in Annie (Lehi, Utah). Decision Process The firm operates as a partnership with multiple partners (Larkins, Chesney, Duboe, Knight) making collective investment decisions. They are known for high-conviction, early commitments before a company's success becomes obvious. Founder Preferences Chicago Ventures seeks founders building in industries where the partners have deep knowledge. They explicitly favor overlooked founders and teams — those not getting attention from coastal VCs. They value operational founders with deep domain expertise and appreciate the "unfair advantage" founders bring to their markets.