Organization · Venture Capital
Woolly Bear Capital
Woolly Bear Capital is a Chicago-based venture capital firm specializing in both secondary and primary investments. The firm focuses on providing liquidity to founders and employees of startups while investing in sectors like AI, cybersecurity, and FinTech.
Overview
What Woolly Bear Capital does
What Woolly Bear Capital is
Woolly Bear Capital is a Chicago-based venture capital firm specializing in both secondary and primary investments. The firm focuses on providing liquidity to founders and employees of startups while investing in sectors like AI, cybersecurity, and FinTech.
How it participates in the startup ecosystem
The current public profile supports funder capabilities. Each capability below is shown separately so organization identity and role-specific information do not get conflated.
Operational profile
Organization status and context
Organization status describes the entity itself. Funding and program availability appear within the relevant capability profile.
- Operational status
- Active
- Organization type
- Venture Capital
- Structured capabilities
- Funder
- Last reviewed
- May 4, 2026
Official channels
Find Woolly Bear Capital elsewhere
Open the official website or a supported primary organization account.
Capability profile
Woolly Bear Capital as a funder
Investment thesis
Woolly Bear Capital backs ambitious founders by providing both primary growth capital and structured liquidity for early stakeholders through a dual-mandate strategy.
Focus narrative
Woolly Bear Capital invests in both secondary and primary markets. Their secondary investments aim to provide liquidity to early stakeholders, allowing them to diversify their assets and focus on value creation. The firm’s primary investments are directed towards ambitious founders, helping them scale their businesses, refine products, and expand into new markets.
Value beyond capital
Woolly Bear Capital offers a unique dual-mandate approach, providing both primary growth capital and structured liquidity solutions for early employees and stakeholders. This allows founders to manage their shareholder dynamics effectively while pursuing aggressive growth strategies.
Focus and fit
- Stages
- Seed · Series A · Growth Equity · Secondary
- Regions
- United States
Availability
- Currently deploying
- Yes
Portfolio and track record
Portfolio context
Specific portfolio companies have not been publicly disclosed, but Woolly Bear Capital's Cherry Fund II focuses on providing secondary liquidity across multiple anchor portfolio companies in the B2B technology sector.
Common questions
What to know about Woolly Bear Capital
Upseed classifies Woolly Bear Capital under the Venture Capital organization type. Its current public profile includes funder capabilities.
Source and update disclosure
Know what this page is based on
Source basis
Public organization and program material, official websites, and structured Upseed records.
Last reviewed
May 4, 2026
Known limits
Capability profiles appear only when a structured public profile also contains decision-useful role evidence. Terms and availability can change.
Upseed is an independent guide. It is not affiliated with or endorsed by the organization described on this page.