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Chicago Ventures CV Fund IV & CV Opportunity Fund

Geography
United States
Stage
Pre-Seed
Fund size
$80M
Focus
AI/ML, Digital Health, Mobility & Transport and SaaS
Signals
Published
Share
N°01 / About

About Chicago Ventures CV Fund IV & CV Opportunity Fund

Chicago Ventures CV Fund IV & CV Opportunity Fund is a venture capital firm based in United States, focusing on Pre-Seed stage investments. The fund actively supports founders building innovative solutions in AI/ML, Digital Health, Mobility Transport, SaaS, providing strategic guidance and capital to help startups scale.

N°02 / Thesis

Investment Focus

Location / RegionUnited States
Funding StagePre-Seed
Industry Focus
AI/ML
Digital Health
Mobility & Transport
SaaS

Investor Signals Profile

active

Sweet Spot

AI-native insurtech, logistics, or fintech founder targeting underserved, data-rich risk

insurtech
AI-native underwriting
consumer fintech
catastrophe-exposed markets
logistics & supply chain tech
logistics data platforms
specialty services AI
healthcare cost containment
agent-native infrastructure
AI inference platforms
autonomous agents as customers
platform native integrations
seasonal demand arbitrage

Bullish Signals

Portfolio co Kin in 14 statesexternal
Kin covers 50%+ US home insurance marketexternal
AI-native portfolio co scaling fastexternal
Kin enters Oklahoma — zero new insurers in yearsexternal
HintHealth DPC membership up 837% since 2017external
Sunbit: Forbes Fintech 50 three years runningexternal
Freightpipes 2nd AI acquisition, all-cashexternal
GoodShip lands Prime Inc. as anchor partnerexternal
Telnyx: 14K+ customers, 100M+ daily API requestsexternal
G2 launches MCP integration with Claudeexternal
BookCameo integrated directly into TikTokexternal
Project44/LSP44: NPS swung from -35 to +39Chicago Ventures Twitter
LSP44 largest logistics data graph, now standaloneChicago Ventures Twitter
Freightpipes hired Stripe VP—revenue engineering muscleChicago Ventures Twitter
Freightpipes AI Theft Prevention: 1.5B shipments monitoredChicago Ventures Twitter
Kin $1.9B catastrophe reinsurance, 25% cost cutChicago Ventures Twitter
Kin auto: $6M premium in 5 months, 250K policiesChicago Ventures Twitter
Sunbit: 5.5M+ customers, 40K+ merchant locationsChicago Ventures Twitter
OneRail: 4K+ store locations, Inc. Best Workplaces 2xChicago Ventures Twitter
Healthjoy: 24.5% specialist cost cut, 50%+ lab reductionChicago Ventures Twitter
Guthrie AI $4M Seed—bid turnaround weeks to daysChicago Ventures Twitter
CoPilot Search: WSJ-featured hidden fee exposé, FTC dataChicago Ventures Twitter
AI agent auto-signed up for Telnyx, provisioned API keyChicago Ventures Twitter
Telnyx agent-native onboarding with AgentMail—first-class AIChicago Ventures Twitter
Freightpipes Mo AI analyst: hours-long analysis to secondsChicago Ventures Twitter
Kin California expansion: condo + flood, no 30-day waitChicago Ventures Twitter
BookCameo Yahoo Sports: fantasy football orders +300%Chicago Ventures Twitter
Buildforce: 2M+ electrician hours, $10M Series A national pushChicago Ventures Twitter
Telnyx sovereign GPU in Dubai—regulated-industry AI computeChicago Ventures Twitter
HintHealth all-in-one clinical+billing+ops for 50 statesChicago Ventures Twitter
LSP44 launched profitable, 9 of top 10 LSPs already usingChicago Ventures Twitter
Guthrie AI Virtual Bid Assistants: early users bid 70% moreChicago Ventures Twitter
Entegrata: 20 customers, 10 Am Law 200 firms in 2026Chicago Ventures Twitter
Project44 Intelligent TMS: G2 Leader, 4.7/5, 733 reviewsChicago Ventures Twitter
Project44 TMS fastest-growing, shipper revenue +57% YoYChicago Ventures Twitter
Project44 TMS only 4 of 11 vendors earned Leader statusChicago Ventures Twitter
Project44 TMS: 93% users say headed right directionChicago Ventures Twitter
BookCameo Yahoo Fantasy: 300% fantasy revenue growth YoYChicago Ventures Twitter
BookCameo: 10M+ videos facilitated, August peak demandChicago Ventures Twitter
BookCameo fantasy average request $100 vs $79 platform meanChicago Ventures Twitter
BookCameo turned dead season into Thanksgiving-level forecastingChicago Ventures Twitter

Contrarian Signals

Heavy catastrophe exposure in portfolioexternal
Freightpipes thesis tied to geopolitical disruptionexternal
LSP44 took 4 years to achieve +39 NPSChicago Ventures Twitter
Auto cross-sell early—long tail to home base maturityChicago Ventures Twitter
Agent infrastructure still nascent market, long burn-down aheadChicago Ventures Twitter
Freight AI split-out model unproven at scale long-termChicago Ventures Twitter
Seasonal arbitrage risky—August to January sustain challengeChicago Ventures Twitter

Founder Do's

Target underserved or avoided markets
Use data to outprice legacy insurers
Build AI-native core product
Show deliberate geographic expansion logic
Enter markets with structural disruption (weather, trade routes)
Invest in LSP/carrier network effects over years
Measure NPS obsessively—transform negative to positive
Spin winners into independent businesses when ready
Design for autonomous agents as first-class customers
Launch profitable spin-outs from data platforms
Embed natively into existing workflows (e.g., fantasy platforms)
Unlock seasonal demand through native integrations

Founder Don'ts

Avoid broad market assumptions
Don't ignore catastrophe-prone niches
Don't skip human support layers
Don't rush spin-outs; build moat first
Don't treat agents as second-order use case
Don't miss ecosystem embedding opportunities

72 signals on Chicago Ventures CV Fund IV & CV Opportunity Fund

41 bullish · 7 contrarian · 12 pitch do's · 6 don'ts · 6 GP profiles, each with its source. From €9/month, cancel anytime.

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Facts

Fund Overview

Fund Size$80M
Saves0
Website
LinkedIn
People

Key People

Rob Chesney, Stuart Larkins, Eric Duboe

Jett McCandlessFounder/Leadership
Lucas WardFounder
Vinay MathurCTO
David CasemCEO
Mackenzie O'ConnorCOO
Steven GalanisFounder/CEO
N°04 / See also

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