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FAQ

  • What types of companies do you invest in?
    • We invest in US-based, software oriented companies. Our sweet spot is co-leading or leading seed rounds (usually a round of $1-5m).
  • Is there a good way to know if my company is a fit for Cowboy to invest?
    • If you have a technology-driven solution to a big and/or growing market, are based in North America, haven’t yet raised a seed round, want to have a trusted, collaborative relationship with your early stage investors, and believe you’re building a company that could have a ‘VC-scale outcome’, we’d love to talk with you about what you’re building.
  • In what areas do you invest?
    • We invest in enterprise and consumer oriented software-driven companies. We have team members with specialties in areas including vertical AI, data privacy, tech infrastructure, developer tools, education technology and digitally-powered new consumer brands.
    • We also love to invest in companies that will build important new categories of software. Just because we don’t have an active investment in your category, doesn’t mean we aren’t interested. Our team members have had long careers in tech and have worked with many different types of companies - we’re interested in a wide array of software oriented technology.
  • How much do you typically invest?
    • Our initial investment is usually between $500k - $3M. We also reserve funds for follow-on investments in the series A and beyond.
  • Do you lead funding rounds?
    • We love to lead and co-lead seed rounds. Our focus is being super trusted, involved investors to help founders be more successful and more supported than they would be otherwise. That means being a sounding board on priorities, helping make key hires, helping with product and go to market planning, making customer introductions, helping with marketing and positioning, helping prepare for a next round of funding, and being there for the highs and the lows. That’s where we shine.
  • Do I need a warm intro to pitch my company?
    • No, you don’t need a warm intro. While we appreciate the hustle it takes to find a mutual connection, we also know the ‘warm intro’ can make it harder for folks to get access to capital. We do review and try to respond to every cold inbound - email us at Hello@Cowboy.vc.
  • What are your criteria when evaluating a prospective investment?
    • Our diligence process is organized around areas we call our four Ps: People, Potential, Product and Plan. 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.
  • What is your due diligence and investment process?
    • We like getting to know you, and we want you to get to know us. We are a small and nimble team so we can move quickly.
    • In advance of an initial meeting, we’ll try to review any materials a founder has shared to help us understand the business and opportunity. Once we have an initial meeting and we’re excited to learn more, we typically dig into the space by spending more time with the founders and talking to others who will help us learn more. We might ask for customer or other professional references. At some point, we’ll usually ask the founder to meet with our whole team for discussion about the opportunity. We also want founders to ask us questions to understand what it’s like working with us and what they can expect in joining the Cowboy community.
    • If it’s a fit, we’ll discuss potential terms and timing with the founder ahead of providing a term sheet. We know every process is different so we leave time each week in our calendars to ensure we have capacity to move as quickly as we might need for new investments.
  • How do you help companies after investing?
    • Our focus is being trusted, involved partners. We come in with our sleeves rolled up, ready to help founders see around corners and respond to the many challenges that come with building in the early stages.
    • We operate as a collective team, meaning that founders have access to the knowledge, experience and network of everyone on our team. Tactically, we can help by being a sounding board on assumptions and priorities, helping make key hires, helping with product and go to market planning, making customer introductions, helping with marketing and positioning, helping prepare for a next round of funding and more.
    • We won’t always have an answer, but in those cases, we usually know someone who does. Perhaps most importantly, we’re here to support our founders during the highs and lows of the startup journey. We know running a startup company can be hard. We don’t want to hear that you are killing it. We want to know how you are doing.
  • What key theses are you exploring currently?
    • Each Cowboy team member is exploring different themes and areas of interest at different points in time. Check out our blog, individual investor pages, and follow us on Twitter to learn more!
  • Are you hiring?
    • We are a purposefully small team but will hopefully add awesome new teammates in the future. Check out our careers page and follow us on Twitter for the latest.
  • Are your portfolio companies hiring?
  • Why the name Cowboy?
    • Cowboy Ventures was originally a placeholder name during our first fund raise in 2012. Names and words are important, and we thought we’d come up with a more “serious” name after raising the fund. After buying many urls, we realized Cowboy represented exactly what we were looking for – a spirit of the west, integrity, independent thinking, resilience, substance without formality, and being willing to brave the frontier with few resources and a small team. Cowboy Ventures also had a sense of humor as a name; and it evokes family, as it is a name conjured by founder Aileen Lee’s daughters and is the name of her son.