Aileen Lee
Founder and Managing Partner @ Cowboy Ventures
Palo Alto, United States
Aileen Lee is a seed investor at Cowboy Ventures in Palo Alto focused on E-Commerce and Software. Aileen is the founder of Cowboy Ventures, a seed-stage focused fund. They seek to back exceptional teams building technology that re-imagines work and personal life in large and growing markets - what they call "Life 2.0". She was formerly a partner with Kleiner Perkins Caufield & Byers, and the CEO of RMG Networks. A graduate of MIT, Aileen has an MBA from Harvard Business School and is a Henry Crown Fellow of the Aspen Institute.
- Total investments:
- 68
- Last investment:
- Lead investor:
- 25%
Last updated:
For AI agents: llms.txt
Industries Aileen Lee invests in
Stages Aileen Lee invests in
Countries Aileen Lee invests in
Contacts
| Type | Contact | Validation |
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| Work email | ||
| Personal email | ||
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Investment Focus
Industry
- E-Commerce 10 (15%)
- Software 5 (7%)
- EdTech 4 (6%)
- Shopping 4 (6%)
- SaaS 3 (4%)
Stage
- Seed 23 (34%)
- Series A 17 (25%)
- Series B 11 (16%)
- Series C 6 (9%)
- Series D 2 (3%)
Country
- United States 32 (47%)
- Turkey 1 (1%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
| Uplimit is where anyone can learn the most in-demand skills and actually put them to work. Where leading organizations build technical skills at scale. It’s where industry-leading instructors show how they tackle real problems, with real methods. And where the perfect combination of teaching best practices, top practitioners, technology, andcollective peer learning makes real growth accessible to us all. | $11M / Series A / Jul 23, 2024 | ||
| Tally is a consumer tech company pioneering full-service financial automation. Founded in 2015, we built the first automated debt manager to help people overcome credit card debt and put billions of dollars back in people’s pockets. Tally’s vision is to automate people’s entire financial lives, so they can stress less about money and do more ofwhat they love. | $80M / Series D / Oct 03, 2022 | ||
| CoRise is where anyone can learn the most in-demand skills and actually put them to work. Where leading organizations build technical skills at scale. It’s where industry-leading instructors show how they tackle real problems, with real methods. And where the perfect combination of teaching best practices, top practitioners, technology, andcollective peer learning makes real growth accessible to us all. | $8.5M / Seed / Sep 28, 2022 | ||
| Uplimit is where anyone can learn the most in-demand skills and actually put them to work. Where leading organizations build technical skills at scale. It’s where industry-leading instructors show how they tackle real problems, with real methods. And where the perfect combination of teaching best practices, top practitioners, technology, andcollective peer learning makes real growth accessible to us all. | $8.5M / Seed / Sep 28, 2022 | ||
| Hone is a live learning platform for management training that cultivates soft skills with hard data. Hone blends the best of expert-led small group training, peer learning, continuous reinforcement, and a technology platform to develop better leaders, managers, and teammates for today’s workplace. | $30M / Series B / Aug 19, 2022 | ||
| Most Marketing teams can’t play a meaningful role in breaking through to target accounts because the 1:1 marketing strategies that work don’t scale, and what scales doesn’t work.Mutiny helps B2B companies generate pipeline and revenue from their target accounts through AI-powered personalized experiences, 1:1 microsites, and account intelligence.We are backed by Sequoia Capital, Tiger Global, Insight Partners, and Y Combinator. | $50M / Series B / Apr 20, 2022 | ||
| GetSetUp is an online platform and community that helps older adults enjoy more fulfilling, independent, and socially connected lives through learning. GetSetUp offers on-demand, engaging learning experiences that range from teaching everyday technical skills to enrichment-focused courses taught by passionate instructors. | $10M / Seed / Nov 22, 2021 | ||
| Hone is a live learning platform for management training that cultivates soft skills with hard data. Hone blends the best of expert-led small group training, peer learning, continuous reinforcement, and a technology platform to develop better leaders, managers, and teammates for today’s workplace. | $16M / Series A / Nov 02, 2021 | ||
| Most Marketing teams can’t play a meaningful role in breaking through to target accounts because the 1:1 marketing strategies that work don’t scale, and what scales doesn’t work.Mutiny helps B2B companies generate pipeline and revenue from their target accounts through AI-powered personalized experiences, 1:1 microsites, and account intelligence.We are backed by Sequoia Capital, Tiger Global, Insight Partners, and Y Combinator. | $18.5M / Series A / Sep 15, 2021 | ||
| Guild Education's lifelong learning platform offers classes, programs and degrees for working adults, with a path for them to move forward in their education and career. Guild offers these adults support from start to finish, with their technology platform for discovery, learning, and organizing the experience, and extra support with theirtech-enabled student advising model.Founded in 2015, the company is headquartered in Denver, Colorado, United States. | $150M / Series E / Jun 02, 2021 | ||
| See all 68 investments → | |||
Co-Investors
About Cowboy Ventures
Cowboy Ventures specializes in financing businesses operating across multiple domains, including enterprise solutions, financial technology, software infrastructure, digital security, healthcare, and consumer platforms. Aside from delivering early capital infusions, the enterprise offers advisory assistance to corporate founders to aid with executive recruitment, product management frameworks, scale strategies, and follow-on fundraising initiatives.
Cowboy Ventures Contacts
| Name | Phone | Socials | |
|---|---|---|---|
Caroline Duffy
Partner
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Jillian Williams
Principal
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Aileen Lee
Founder and Managing Partner
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Chad Sanderson
Scout
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Donna Boyer
Wrangler / Venture Scout
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FAQ
What does Aileen Lee invest in?
Aileen Lee invests primarily in E-Commerce, Software and EdTech startups, most often at Seed and Series A stage. Most of the 68 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
How do I contact Aileen Lee?
Public channels for Aileen Lee include LinkedIn, X (Twitter) and Facebook. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.
When did Aileen Lee last invest?
The most recent investment recorded for Aileen Lee closed in Jul 2024. Shizune tracks 68 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Oct 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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