I co-founded Cowboy Ventures and All Raise – Aileen LeeFeatured

Hi Elpha! I'm Aileen Lee, an investor and co-founder of Cowboy Ventures, a seed-stage focused fund. We back exceptional founders who are building technology products that re-imagine work and personal life. In 2017, I co-founded All Raise with 30 other senior women, including @jesslee and @anuhariharan, to accelerate measurable success for female founders and female investors. So far, 200 female venture capitalists and founders have delivered more than 1,000 hours of mentorship in addition to boot camps, peer support groups, events, and more.Prior to founding Cowboy and moving to seed stage investing, I was a series A/B venture investor at Kleiner Perkins Caufield & Byers since 1999, working with a range of consumer, enterprise, media and greentech companies including Rent the Runway, Shopkick, Good Technology, Bloom Energy and more. I'm also the proud mom of 3 kids plus a dog, chickens and bees, and wife to CTO and co-founder of a VC-backed tech startup.Ask me anything about being a VC, starting a fund, championing for change with a non-profit or something else!
Thank you for spending time with us, Aileen! Please post your questions for Aileen before Thursday. She may not have time to answer every single one, so upvote the ones you’d most like her to answer.
Thanks @aileenlee for doing this. In this round that I'm raising for, pretty much all of the female-focused funds turned me down without a call because they don't have expertise to evaluate my tech. To be fair...very few people have a computational cybersecurity expert on board. This didn't stop male VCs from finding someone to vet my tech & move things forward. But my company landed dead in the water, despite my keeping the round open longer *expressly for the purpose of adding women to my cap table.* Do you feel there's a pink ghetto for female founders/funders? I felt like if I was launching a subscription box or D2C bra company, I would have more traction with female funders. More traction with women funders would also help me find/attract more women to my C-suite. I'm a fierce STEMinist committed to walking my talk, but despite my best efforts & a year into operation, I'm still the only woman at my own company.Any and all advice will be really appreciated. Thanks!
I support you!
@Carenna Thanks! And um..."support" like "moral support" or support like "here's a $500k check." ; )
Morally, I have encouraged many women to build solid relationships with money and business and it can be really wonderful when you have your thinking in a good place.
Agreed! And thank you. I'll take all the support I can get!
I am eagerly awaiting the answer to this! Haha.
Great question! I looked at ANOVA's website, and I wonder if the "pink ghetto" occurs esp in fields that are traditionally heavily male - like hardware, cybersecurity, networking, etc. For example, I worked on a Google Fiber-based hardware networking product at Google and definitely felt the lack of women. On the one hand it played to my advantage because I exceeded expectations. On the other hand, interacting with my colleagues required a lot of tact and finesse. Speaking as an angel investor - I know it's important to align your pitch with the interests of the investors. I'm part of an MIT Angels group - and the startups that come through there skew heavily towards deep tech ones. If you're still raising I'd be happy to take a look at your pitch deck and submit it to MIT angels? Lmk!
@yoyothesheep Yes please! sending you a dm now. And thank you. experience mirrors yours in those "one of these things is not like the others" work situations. Being a woman has never worked to my advantage in fundraising though.
I'm in a similar boat and therefore very keen for the answer to this one! Thanks @Gentry for asking it.
Gentry, we're in the same cybersecurity market (but different sub-market). Let's help each other!
@fannysurjana With pleasure. What can I do? How can I help?
For starter, let's be connected on LinkedIn :) I'm part of Women in Security and Privacy & Women in Information Security but it's not as active as I expected. I'm still looking for a good, active online Women Founders/Leaders in Cybersecurity. Premise is that people who successfully invested in women like us would like to rinse & repeat.
@fannysurjana I'm in Women in Defense (the programming is A+) but online isn't at all focused on investment/startup growth. I only know of two women who sold their cybersecurity companies, one has been extremely helpful, the other has been extremely cagey. I agree with your thesis/premise! Given the buzz around cybersecurity and documented advantages for investing in women-led companies, one would think both genders would be throwing money at us, right?
hi @Gentry - thanks for the question! We have a long way to go, but think female founders have a better chance than ever to raise VC funding from all genders and all kinds of funds, in all kinds of spaces. Don't think the founders have to be doing 'pink' (ugh) things to raise VC money, and they also can raise from generalist tech funds in addition to female-focused funds. That said, women are maddeningly still only ~10% of the partners at VC firms, and ~70% of firms don't have ANY female partners at all - so founders only have a 1 in 10 chance of meeting with a female partner unless they are deliberate about who they try to meet with. It's awesome you went out of your way to meet with women and get them on your cap table, and hope you don't stop trying - thank you - we need more women in VC at all firms and all levels, and more successful female founders. Were you able to meet with female VCs who focus on enterprise sw, frontier tech and/or security sw at the more generalist tech VCs - they do exist! Some people i might seek out who have security expertise are Chenxi Wang at Rain Capital and Theresia Gouw at Aspect; or Jocelyn Goldfein at Zetta, Stacey Bishop at Scale, Maha Ibrahim at Canaan, Ann Miura Ko at Floodgate or Sarah Guo at Greylock who focus on enterprise SW; or Dayna Grayson at NEA who does industrial and enterprise sw. We also do lots of enterprise SW at Cowboy and have 1 security investment, and we along with the aforementioned and not complete list of women vcs do technical diligence all the time :)Hope that helps!
@aileenlee Totally helps! Thank you! I had great, erudite conversations with Jocelyn & Ann Miura. I will check in with the others and build on your suggestions....maybe the others would be interested in vetting deep tech for the female-focused funds who are don't have in-house expertise. I would help with that!We need more women at the top in tech! (And tech financing)
@jordyn you're recruited/required to help me with this. ;)
Count me in!
As a female VC, what is one thing you wish female founders would do more when they pitch? One thing you wish they would do less?
I'm eagerly awaiting the response to your question!
TBH I don't notice as many opportunities for improvement as i might have 5 years ago. We're also fortunate to get pitched by lots of female founders who do an awesome job. That said, some things for female founders to think about:- put early in the preso how large the addressable market is to get the audience excited. Institutional VCs are usually looking for addressable markets of $5bn at a minimum- some say that female founders tend to pitch smaller ideas than men. Make sure to share a big mission or vision early on - one that sounds like could grow into a large, $1bn + company some day. - that said - try not to overreach or over spin / stretch the truth - it risks your credibility. Women are not given the benefit of the doubt that men are, so it gives your audience a reason to ding you :(- know you numbers, and don't say "i'm not good with numbers"- give examples where you've hustled to figure out something- practice your pitch a LOT! It will give you confidence and help calm nerves, and also allow you to be yourself and feel natural about telling the story.
Thank you so much for the pointers! Also an important reminder that as women, we're much more subject to expectations of "straddling the line," i.e. don't pitch too small or too big, be confident but not TOO confident, etc.
A couple of questions, feel free to answer any or all of them! 1. How do you think VC will change over the next 5 - 10 years?2. What is it like being a female VC now that there is a huge push towards diversity in this space?3. How can someone who has VC experience (fellowships & internships) stay engaged with the community while working at a startup?
1) I wish i knew how VC will change over the next 5-10 years. If you have some predictions please share them!2) Think it's a better time to be a female VC than ever. Doesn't mean it's easy. Women still have to deal with sexist comments, not being included in events or in deals, a boys network, being underestimated, over scrutinized, paid less, being given the benefit of the doubt less, and so much more. But now that founders, other VCs and LPs realize there have been issues, more people can do more to be part of the solution. Plus our numbers have grown and women and men are more supportive of women in the field which is great!3) stay in touch w/ your friends in VC; share ideas / opportunities; offer to help with diligence etc? thanks for the questions!
What sectors or technologies are you most excited about and why?
Hi! There are MANY areas of new tech startups we're excited about at Cowboy Ventures. Just a few:- "unsexy tech". There are a lot of areas within companies that are not as visible to the customer (backoffice operations, finance, HR functions, logistics, infrastructure, data & analytics infrastructure...) that still operate using outdated software, spreadsheets and even pen & paper. The folks who have to use this old software and old processes will be so much happier and more productive when they get fast, mobile friendly, data-driven modern enterprise software with great UX. my partner Ted wrote a post about this in more detail here - "Learning loop", machine learning-driven software that leverages data to provide new insights and/or save time and money. We're investors in some exciting machine learning and AI-driven enterprise software companies like Textio and but it's just the start. We're excited to find more opportunities that leverage underlying or proprietary data to offer smarter software that learns as it is being used, saving users time and offering new insights. - New consumer digital communities. Social media products have become so pervasive and yet they have left many feeling less happy, less connected, and even unsafe; plus they've been taken advantage of to spread misinformation and hate. After over a decade of the first widespread social media products, feels like there's a big opportunity for new, next gen digital communities which take the learning of the first social media products and make them better for users.- New direct to consumer brands. There have already been so many great successful ones in the past decade but there's always room to delight customers with products that are more convenient, deliver better value, or upgrade daily experiences to provide more delight.- We would also like to see technology that helps the aging population. The developed world is getting older and while startups have often been founded to solve millennial or gen-z problems, we believe there's a great opportunity to serve the growing number of older folks for health or just lifestyle & entertainment.- Would love to know what areas you think we're missing or should be paying attention to in addition to the above!
Thank you so much for joining us for an AMA and for all the work you do in VC and with allraise - you are breaking ceilings for all of us here.When joining a fund, do you think one should take into account whether they already have a female partner (for career progression, mentorship,...)?
Seconding the breaking ceilings remark!
Sounds like a totally awesome family! I am curious about the details of your job transitions between school, Kleiner and Cowboy. What has each step looked like for you - interviews, networking, going rogue? Would you change anything in your career path? I'm Chevonae, a VC analyst in Toronto.
Why should female founders raise VC money for some businesses vs. angel funding/social impact investment vs. making money? What are the main distinctions for those who should or should not try pitching to VCs for capital vs those who are looking for smaller funds or different types of funds to help grow their business?
Any suggestions on how to deal with Ageism in the investor community and do you think it is an uphill battle to get funding when you are over 40?
I have three questions for you:1. How often does All Raise Seed Bootcamp transpire?2. Does Cowboy Ventures have additional info you prefer to see in the investor deck, other than what has been outlined by All Raise below?Decks should be no more than 15 slides. Please include the following in your deck: Problem, solution, market size, business model, traction to date, competition, vision, team, financial projections, fundraising history and seed round goal.3. Does Cowboy Ventures fund pre-seed?
First off, thank you for supporting women entrepreneurs. And thank you for being so successful at it! I am impressed with the family, kids, and dog, and most of all for the chickens and the bees! I am curious about how you run pitches at your office location. Do you have companies come in and present back to back the same day? Or is it more of a serendipitous process through which founders come and present when requested? What is the biggest technology failure that affects your own productivity? What would you like to see change/evolve in the next five or ten years? Is there a specific product/tech that you would like to have NOW?What concerns you the most in your day-to-day? How can the entrepreneurs in your community help you so that in turn you can better help them? Thank you!Flavia SparacinoCEO, BEAM ConferenceSanta Monica, CA
When you work with startups and social capital raising what valuation methodologies do you prefer and what key metrics are you looking for with startups post MVP launch with product in market.
Thank you for all you’re doing to promote inclusion in all aspects of this startup ecosystem.I am truly humbled and in the fortunate position as a startup founder to have been approached these past few weeks by VCs inquiring to meet and speak about my startup. I am not actively raising as of yet, but I have read about two schools of thought on 1. developing relationships with VCs is beneficial, and how 2. speaking with VCs too early is a mutual waste of time. I am leaning towards option 1. What are your thoughts on this, and how do you think the best way to leverage these meetings are? Thank you in advance for your feedback.My name is Joana Gutierrez and I am the founder of PINYA. At PINYA, we are transforming the trillion dollar hospitality and commercial property industry by rewriting the rules of how people come together.
What were your biggest challenges when starting Cowboy? Wondering if there’s any overlap between the task of creating a company to build product vs. creating a company to invest in product companies. Thanks in advance; excited to get your take!
1. Do you think lack of engineering skills, and resulting lack of traction because female founders do not have a built/robust prototype, are significant contributors to why women raise less money?2. Let's say, hypothetically speaking, a large tech company was willing to 1: donate developer hours to help female founders build prototypes or 2: donate small sums of money (~$20k) to help female founders hire someone to build a prototype - would this be impactful - and based on your past experience, data, etc- be solving a major problem in the system? Thanks so much for your thoughts!
I'm currently a part of the ongoing AllRaise bootcamp and a big believer in your mission. In a way, my company practices empowering women as well through our partnerships and thinking about the problem at its roots - most of our partners are women led or husband/wife small businesses and our programs actively encourage young girls to try STEM related activities. How can I, and others interested in AllRaise's mission get more involved, if we aren't at a stage where we can contribute as a mentor yet?
First off - I've been following your work for the past few years, and HUGE SHOUTOUT for all that you've done to evolve the investing landscape, especially around accessibility for women!As an angel investor, I'd love to hear your thoughts on1. What are some industry trends you're particularly excited about, both from a personal and an investor perspective?2. What are major gaps you still see in encouraging more women founders/investors, and what can we here do to help? (This is obviously a big topic so feel free to abbreviate!)Thanks so much! 💪
I feel that almost every company is a technology company nowadays. Therefore, as technology is becoming a commodity, businesses are starting to compete on business model innovation. Is there any interesting business model which you would like to see more?
Aileen, thank you so much for opening up your experiences and expertise to us. How, as a younger non-white woman, did you cross the "credibility chasm" that Neha Narkhede of Confluent describes? When the current value you bring to the company does not yet match your current/future potential, and you needed champions/mentors/supporters to help you through it?
I am cofounder of a B2B startup that is interested in selling software component for fashion e-commerce. Is direct email to CEO and President good approach to reach the retailers? What is the best and easy way to reach the decision maker of clothing retailers?
Thank you very much for being here, and for creating All Raise! I am working on an idea to build a product to help people improve social and emotional skills, skills important for people's personal and professional success and happiness. What are your thoughts on this space, and what are the most important factors that contribute to startups' successes based on your observations?
My team and I are building a microsaving platform to help youth save money and we are eyeing expansion into a digital bank in the future. May I know what will be your advice to scale in fintech as it is heavily regulated industry and every new market has a set of regulation on it's own, limiting the rapid scalability of the company.
Who are your favorite angel or early stage investors in B2B/Enterprise Software? Who are your favorite thought leaders in this space? Thank you for sharing your time with us!
Aileen, at the risk of echoing what others are saying, your work in this space is incredible and I'm grateful for the fact that you exist in this world. I'm the CEO and Co-founder of AuCoDe, an AI-based Fintech startup that detects online and social media controversies which can affect equity prices. (...and also a proud mom of one, with #2 on the way!)As a seed round investor, what is your reaction to startups that have raised non-dilutive capital from federal grants and other, similar sources? Does it make it more likely or less likely for you to invest in them?Thanks for offering your valuable expertise and insights in this wonderful forum. This is part of what makes elpha incredible.
Hi Aileen! Thanks so much for hosting this Office Hours. I'm Christine, co-founder of cannabis and hemp infused ingredients brand Potli. We're currently raising a seed round, and often hear that based on revenues we're just "too early" for a lot of VC's. We respond by pointing to our recent growth and pipeline, but what else would you suggest we speak to and focus on?
Hi Aileen, I'm supporting the closing of a seed round for a martech business, deep in corporate social responsibility and impact, with a female co-founder called Cheerity. They're so close to meeting the round, is revenue generating, and has amazing traction with organizations like the United Nations. Would you have any interest investing? Please email me at [email protected] to learn more. Thank you, Erika
Thanks for doing this @aileenlee! Do you a good Keto bread recipe you really love and want to share with us?
Hi @Aileenlee! Thanks for all your hard work to support female founders and investors. My consumer hardware startup is based in Puerto Rico and in the process of proving product-market fit. Our unit economics are pretty astonishing, we're convinced that we have first-mover advantage, and there's an opportunity to parlay that into first-scaler advantage within 3 years in an enormous global market.With that said, I'm still a female founder with Hispanic co-founders based outside of Silicon Valley and there's no direct flight for west coast investors and future board members. Is early traction going to be enough to allow us to raise serious venture capital? What do we need to do to level the playing field and get people excited to venture beyond Sand Hill road?
Hi Aileen. Firstly, thank you for taking the time to host this session for us. :)I am currently working to build a founding team for my startup and would like to understand what leads to a successful pre-seed round.My vision is to create a digital + experiential cannabis community. An important resource for the community will be connections through an app/website, which is costly, time consuming and requires a team of experts to build. And as a non-technical founder, this is an area that I cannot figure out on my own. Since I will need funds to bring on that founding team + build a prototype/MVP, what do you recommend for:1) The best strategy for pre-seed funding2) Are there specific investors I should reach out to? 3) What are the most important things these investors are looking for and want me to address?Or, do you feel it is better for me figure out another solution and seek seed round funding after there is traction in the marketplace?Looking forward to your insights! Thank you so much.
Hi everyone – Thanks for all your amazing questions! Aileen will be replying to questions that have already been submitted, but isn't taking new ones. Hopefully even if she doesn't reply to your specific questions, insights she offers in other replies will be helpful to you, too!
thank you Cadran. Should we expect more responses in the next days or was there just limited time to answer selected questions?
Hi! Yes she did earlier this week!