Cowboy Ventures is a seed-stage firm, founded by Aileen Lee, that backs founders with a unique insight into solving an important business problem in a potentially large and growing market ($Bns). It is purpose-built for working with founders at seed and has a specialty investing 'pre-product' (~70% of investments). Diligence is organized around its 'four Ps' - People, Potential, Product and Plan - and it backs both seasoned, 'pedigreed' founders and first-time founders from non-traditional backgrounds across enterprise and consumer software.
A unique insight into solving an important business problem - founders who deeply understand a real, painful problem in a large market, often one incumbents structurally can't address.
“Founders who have a unique insight into solving an important business problem in a potentially large and growing market ($Bns).” — Announcing $260M in new capital with Cowboy Fund IV & Mustang I
“We're looking for founders who have a unique insight to a problem, are targeting in a large and growing market, are obsessed with building an outstanding product and customer experience, and have a plan to execute on their opportunity.” — How we work
“The infrastructure to match skilled, high quality people with these opportunities and manage and pay them is missing.” — The future of independent workers: why we invested in Contra
“Companies are not asking how AI can replace workers, they are asking how technology can help them operate when they simply cannot hire enough skilled people.” — Caroline Duffy
An outstanding product and customer experience built on a technology-driven solution; founders obsessed with product quality. AI-native solutions should deliver better outcomes faster, more scalably and at lower cost.
“We're looking for founders who have a unique insight to a problem, are targeting in a large and growing market, are obsessed with building an outstanding product and customer experience, and have a plan to execute on their opportunity.” — How we work
“AI presents an opportunity to offer solutions that deliver better outcomes, faster, more scalably, and at lower cost.” — Aileen Lee
“a technology-driven solution to a big and/or growing market” — How we work
“We're looking for teams who understand that agent security is not an extension of LLM security.” — Rohan Puranik
A large and growing market measured in billions ($Bns); they like big or not-yet-clear TAM where a category can be created. Market sizing should be grounded in real revenue/spend, often illustrated with a single striking number.
“Founders who have a unique insight into solving an important business problem in a potentially large and growing market ($Bns).” — Announcing $260M in new capital with Cowboy Fund IV & Mustang I
“Professional services in the US drive an estimated $3.2T in annual revenue and employ about 14% of the working population.” — Aileen Lee
“Consumers are a massive market - spending over $16T per year in the US alone.” — Aileen Lee
“We've loved backing 'category creators'- founders have an innovative idea in a potentially big, but not yet clear TAM.” — Marking Cowboy Ventures' 10 Year Anniversary
Because ~70% of investments are pre-product, hard traction is not required - but where it exists, strong pre-launch demand signals matter. For consumer, they want clear understanding of unit economics and engagement metrics.
“70% of our investments are pre-product.” — How we work
“Without officially launching, Contra already has garnered hundreds of thousands of users who have signed up to create a new professional identity.” — The future of independent workers: why we invested in Contra
“It's important to understand unit economics and measure conversion funnel, engagement time, frequency and LTV.” — Aileen Lee
“Sometimes we invest after the founders have figured out some early product / market fit. We've also developed a specialty investing 'pre-product'” — Marking Cowboy Ventures' 10 Year Anniversary
People are the first 'P'. They back both seasoned/pedigreed founders and first-time founders from non-traditional backgrounds, prizing unique insight, passion, deep domain empathy and relevance to the problem. Note: most successful founders historically were in their 30s-50s.
“We support seasoned, 'pedigreed' founders as well as first time founders from non-traditional backgrounds.” — Announcing $260M in new capital with Cowboy Fund IV & Mustang I
“When we met Ben Huffman (CEO) and Gajus Kuizinas (CTO), we were immediately impressed by their deep empathy for the challenges independent workers face.” — The future of independent workers: why we invested in Contra
“When we met co-founders Ali and Amr, we were blown away by their passion, expertise, and vision for the future of real estate.” — Announcing Cowboy Ventures' Investment in Getaway: Investments with a View
“The most successful founders were in their 30s, 40s & 50s; Facebook was a once-in-a-decade outlier.” — Marking Cowboy Ventures' 10 Year Anniversary
A plausible path to a VC-scale outcome with sound unit economics; for consumer, products that grow frequency and spend over time. They like models that democratize access and deliver outcomes more scalably and at lower cost than incumbents.
“Great products grow consumer frequency and spend over time” — It's Time For A B2C Comeback In the Age of AI. But it won't be easy
“believe you're building a company that could have a 'VC-scale outcome'” — How we work
“AI native companies will figure out and execute many of the 'jobs to be done', 24/7, in a more scalable, lower cost way.” — Aileen Lee
“We're excited about fintech solutions that democratize access and make things more efficient, understandable, and engaging.” — Announcing Cowboy Ventures' Investment in Getaway: Investments with a View
A defensible wedge against incumbents - often grounded in the fact that incumbents can't disrupt their own people-powered models - plus 'hairy execution' that builds a real moat. Watch out for free general AI tools raising the bar for purpose-built products.
“With so much existing revenue at risk, it will be hard for incumbents to change their longstanding cultures and disrupt their people-powered business models.” — Where we're looking to invest: AI-powered professional services, a $3T opportunity
“Hairy execution builds a great moat” — Aileen Lee
“Leading AI products like ChatGPT and Claude currently offer consumer utility for free” — Aileen Lee
“We're looking for teams who understand that agent security is not an extension of LLM security.” — Rohan Puranik
A clear platform-shift catalyst - usually that LLMs and AI agents make newly possible what wasn't before, opening a timing window where incumbents are exposed and category creators can emerge.
“Historically, the best consumer companies emerged 2-10 years after the 'big bang' of a platform shift. We're in that window now.” — It's Time For A B2C Comeback In the Age of AI. But it won't be easy
“LLMs and AI agents change what's possible. AI can read unstructured documents and extract what matters, track down and synthesize information, reason through multi-step workflows, handle ambiguity and escalate edge cases.” — Aileen Lee
“The shift from LLMs as chatbots to LLMs _powering agents_ changed everything.” — Rohan Puranik
“GitHub was built for a world where humans write code. That world is ending fast.” — Kathy Huang
Founders raising their first institutional seed - typically a $1-5M round - who haven't yet raised a seed round, with a credible plan to execute on the opportunity (the fourth 'P'). Cowboy writes initial checks of $500k-$4M and leads.
“have a plan to execute on their opportunity” — How we work
“usually a round of $1-5m” — How we work
“$500k - $4M” — How we work
“haven't yet raised a seed round” — How we work
“Professional services in the US drive an estimated $3.2T in annual revenue and employ about 14% of the working population.”
“Companies are not asking how AI can replace workers, they are asking how technology can help them operate when they simply cannot hire enough skilled people.”
“The shift from LLMs as chatbots to LLMs _powering agents_ changed everything.”
“GitHub was built for a world where humans write code. That world is ending fast.”