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Cowboy Ventures is a seed-stage venture capital firm that primarily invests in US-based, software-oriented technology companies, often leading or co-leading initial rounds. The firm is largely sector-agnostic but focuses on identifying underserved markets and aims to be a deeply involved, trusted partner to founders, providing strategic support beyond capital.
Average disclosed round size is $27.9M (across 48 rounds with reported amounts).
Portfolio
54
Fund Size
$260M
Top Stage
Seed
Last 12 Mo
1
Team
Portfolio Breakdown
Stage Distribution
Sector Distribution
Investment Activity
DealsAvg Round Size
Portfolio
54 investments
| Company | Round | Amount | Date |
|---|---|---|---|
 CrunchBase | Series C | $30M | Nov 2025 |
 Uplimit | Series A | $11M | Jul 2024 |
 Homebase | Series D | $60M | Apr 2024 |
 Vic.ai | Series C | $52M | Dec 2022 |
 Drata | Series C | $200M | Dec 2022 |
| TTally Technologies Inc. | Series D | $80M | Oct 2022 |
 LaunchNotes | Series A | $15M | Jun 2022 |
 Mutiny | Series C | $50M | Apr 2022 |
 Arcol | Seed | $3.6M | Mar 2022 |
 The Landing | Seed | $3M | Dec 2021 |
 Contra | Series B | $30M | Nov 2021 |
 Byteboard | Unknown | — | Oct 2021 |
| Vic.ai | Series B | $50M | Sep 2021 |
| Homebase | Series C | $71M | Jul 2021 |
| Drata | Series A | $25M | Jun 2021 |
 Guild Education | Series E | $150M | Jun 2021 |
| NNewness | Seed | $3.5M | Feb 2021 |
| Drata | Seed | $3.2M | Jan 2021 |
 Effx | Seed | $3.9M | Jul 2020 |
 ChartHop | Seed | $5M | Feb 2020 |
| CrunchBase | Series C | $30M | Oct 2019 |
 Mon Ami | Seed | $3.4M | Oct 2019 |
 Passbase | Seed | $3.6M | Sep 2019 |
 NakedPoppy | Seed | $4M | Jul 2019 |
 Tally | Series C | $50M | Jun 2019 |
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Top Co-Investors
Scale Venture Partners7 shared
Redpoint Ventures6 shared
Kleiner Perkins5 shared
Salesforce5 shared
Lightspeed Venture Partners5 shared
GGV Capital5 shared
First Round Capital5 shared
Bloomberg Beta5 shared
Harrison Metal5 shared
Emergence Capital5 shared
Shasta4 shared
Slow Ventures4 shared
Iconiq Capital4 shared
Felicis Ventures4 shared
SV Angel4 shared
Upside Partnership4 shared
Andreessen Horowitz3 shared
GSV3 shared
Khosla Ventures3 shared
Baseline Ventures3 shared
Last updated: 10 April 2026