Investor Profile: Chicago Ventures — Thesis, Cheque Size & How to Apply

If you are researching Chicago Ventures funding, you are looking at one of the most consistent lead seed investors in the United States. Founded in 2012 and based in Chicago, it leads seed rounds before a company's potential is obvious. Here is how to get funding from Chicago Ventures, what its funds have paid, and which companies it backed early.

Thesis: overlooked teams, anywhere, before it is obvious

Chicago Ventures was launched to fill an acute market gap: early-stage capital flowed as if innovation were restricted by geography, raised and distributed within a few select area codes. Its answer is that enduring companies can be built anywhere, by anyone. It invests in overlooked teams, leads seed rounds before it is obvious, and serves as an active, operationally-involved partner during a company's earliest days. It invests off the coasts, backing toys, rebuilds, spin-outs, small markets and unproven founders.

Sectors, stages and cheque size

Chicago Ventures is a seed and Series A investor across supply chain, logistics and warehousing, healthcare, fintech, consumer media and entertainment, data management, proptech, mobility and enterprise tools. Its third fund, Fund III, closed at $63 million in 2021, targeting 25 investments at an average cheque of $1.5 million to $2 million. Its second fund, closed in 2016, included a $60 million main fund and a $6 million sidecar fund. A current total fund size beyond Fund III is not publicly disclosed.

Notable portfolio companies

Its own companies page lists Cameo, G2, project44, SpotHero, HealthJoy, Sunbit, M1 Finance and Kin. Exits include Tock (Squarespace, 2021), Troops (Salesforce, 2022), Truss (Avison Young, 2020) and Pluto TV (Viacom, 2019). At its 2021 fund announcement, the firm said its portfolio companies had raised more than $1.5 billion in follow-on capital, with 17 companies valued over $100 million.

Partners and team

At its Fund III announcement, the firm promoted Peter Christman and Lindsay Knight to partner and named Jackie DiMonte as a new partner. Christman leads investments in enterprise workflow and consumer access companies, while Knight leads post-investment operations, talent and business development. DiMonte, an engineer by training, joined from Hyde Park Venture Partners and is based in Austin, where the firm had made 10 investments since 2015.

Programs, credits and perks

Chicago Ventures does not publicly list an accelerator program or a credits and perks package. Its published value-add is operational partnership: high-conviction investing, board seats, straight-talking advice, talent help and business development support through its post-investment team. Founders should judge it on that partner model and its lead-seed record, not on a published perks bundle.

How to apply for funding from Chicago Ventures

Start on the firm's official site, chicagoventures.com, and use its contact route, ideally with a warm introduction from a portfolio founder, a Chicago ecosystem contact or a co-investor who has worked with the firm. Pitch as a lead-seed candidate: explain why your company is overlooked, why it can be built where you are, and why a $1.5 million to $2 million lead cheque fits. Show early evidence and a clear plan for the seed capital.