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Investors / Cowboy Ventures / Compare with Pioneer Square Labs

Cowboy Ventures vs Pioneer Square Labs

Cowboy Ventures lists 74 portfolio companies and has joined 5 funding rounds; Pioneer Square Labs lists 46 companies and has joined 7 rounds. Cowboy Ventures comes in most often at Seed (60% of its entries), Pioneer Square Labs comes in most often at Seed (86% of its entries). 1 company is on both portfolios, among them LumaTax.

74Portfolio companies46
5Funding rounds joined7
2Rounds led2
4Rounds, last 12 months3
$5M to $20MTypical round it comes in at$5M to $20M
0%Sites no longer answering0%
Show as a table
Cowboy Ventures and Pioneer Square Labs, head to head
Cowboy VenturesPioneer Square Labs
Portfolio companies7446
Funding rounds joined57
Rounds led22
Rounds, last 12 months43
Typical round it comes in at$5M to $20M$5M to $20M
Sites no longer answering0%0%

Where they come in

share of entries by stage
Pre-seed0%0%
Seed60%86%
Series A40%0%
Series B0%14%
Growth0%0%

Cowboy VenturesPioneer Square Labs

Show as a table
Entry stages of Cowboy Ventures and Pioneer Square Labs, share of entries
Cowboy VenturesPioneer Square Labs
Pre-seed0%0%
Seed60%86%
Series A40%0%
Series B0%14%
Growth0%0%

Themes

share of checked companies
AI & Machine Learning18%21%
Fintech13%15%
Enterprise Software12%13%
Healthcare & Biotech9%6%
Education7%0%
Space & Defense4%6%

Cowboy VenturesPioneer Square Labs

Show as a table
Themes of Cowboy Ventures and Pioneer Square Labs, share of checked companies
Cowboy VenturesPioneer Square Labs
AI & Machine Learning18%21%
Fintech13%15%
Enterprise Software12%13%
Healthcare & Biotech9%6%
Education7%0%
Space & Defense4%6%

Companies both back

1

Shared companies are those both firms' own portfolio pages list, each checked against the company's site. The same comparison through the API is POST /v1/overlap, for up to 20 firms. How the data is graded

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Compare Cowboy Ventures and Pioneer Square Labs as data

Pull both portfolios and every co-investor through one API key or MCP, and lay up to 20 firms side by side with POST /v1/overlap. A free account adds Ask AI searches and alerts when either firm adds a company.

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  • Ask AI5 plain-English investor searches a day
  • Full listsEvery portfolio row and two-firm overlap
  • API and MCP100 REST or MCP calls a month, one key
  • AlertsFollow 5 investors for portfolio and fund changes
VCinfo API
$ curl -H "X-API-Key: YOUR_KEY" \
  https://api.vcinfo.io/v1/firms/cowboy.vc/portfolio

# also
GET /v1/firms/psl.com/portfolio
GET /v1/firms/cowboy.vc/coinvestors
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