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Cowboy Ventures
Venture capital firm · Founded 2012 · Active in 2026
Cowboy Ventures is a venture capital firm based in USA, founded in 2012. The page below shows 4 Power Law outcomes from Cowboy Ventures's portfolio — 4 unicorns ($1B+ valuation) and 0 additional thoroughbreds (companies that crossed $100M+ in revenue without yet reaching $1B+ valuation).
Outcomes are concentrated in Other · Edtech · Other B2B Software; top portfolio geographies are USA. Cowboy ranks #385 in Global in the 2026 Dealroom Power Law Investor Ranking by cross-stage outcomes.
Cowboy’s biggest exits.
Cowboy portfolio companies worth $1B+ that have IPO’d or been acquired. Each shows its valuation at exit and, in grey, its current value if still public.
Cowboy’s selected top holdings.
An estimate of Cowboy’s largest live positions — disclosed shareholding × Dealroom’s latest valuation — across 3 companies where Cowboy is a named shareholder, worth about $648M in estimated equity value.
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1
Guild Education
7%
$4.4B
$308M
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2
Drata
9%
$2.0B
$180M
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3
Branch
4%
$4.0B
$160M
Estimated value = Cowboy’s disclosed ownership % × Dealroom’s latest company valuation; direct named stakes only, exited positions excluded. Figures are indicative, not reported marks. See the underlying cap tables on Dealroom →
The 4 Cowboy Power Law outcomes ($100M+ revenue or $1B+ valuation).
Snapshot of where the outcomes are concentrated by country, sector, and stage entered.
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USA4
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Other1
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Edtech1
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Other B2B Software1
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Cybersecurity1
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Series A1
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Seed3
Cowboy's 4 Power Law outcomes.
How does Cowboy stack up?
Cowboy in orange, your selection in blue and other colours. Pick from the global roster of 35 peer investors — scope by startup location or hit "Find similar shapes" to auto-pick the three closest. The funnel matrix mirrors the spider chart on the ranking page; the line chart shows each firm's share of unicorns minted in the selected startup location — peaks reveal vintage years.
Share of new unicorns per year
% of global unicorns minted that year, year by year · hover the chart to see which unicornsStage focus
Companies by entry stage and outcome tierSector focus
Companies per investor across the 10 highest-volume sectorsWhere Cowboy's portfolio founders come from — and where they studied.
15 founders across the 4 Power Law outcomes — split by country of origin, university attended, and the company they worked at before founding. Stanford University Graduate School of Business and Instructure are the deepest single pipelines.
Key people at Cowboy.
Market sentiment
What the market is saying about Cowboy Ventures
An AI-synthesized read of the highest-engagement posts about Cowboy on X over the past 7 days. We rank by likes & retweets, ignore corporate channels, and surface the themes that broke out from real people.
Reading the room on X — pulling top posts and synthesizing themes…
Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour
In the news
Latest news about Cowboy Ventures
Recent press, funding announcements, and portfolio moves mentioning Cowboy — pulled live from Dealroom's news feed.
Want the full picture on Cowboy Ventures?
The Dealroom platform tracks every round, every co-investor, and every portfolio company in real time — across 25,000+ investors and 3M+ companies globally.