aileenlee

Aileen Lee

Startup wife, mom of 3, lover of music, and founder of Cowboy Ventures

THIS CHAT HAPPENED ON September 29, 2015

Discussion

aileenlee
aileenlee@aileenlee · Cowboy Ventures
Hi! My name is Aileen, founder of Cowboy Ventures - we hope to be your favorite backer of seed-stage consumer & enterprise internet software startups (like Product Hunt!). We love founders/companies re-inventing work and personal life through new tech products, we call it "life 2.0". We also had something to do with this "unicorn" thing. I've worked in a few consumer companies and also ran a digital media company; joined VC firm Kleiner Perkins in 1999.
Ryan Hoover
Ryan Hoover@rrhoover · Founder, Product Hunt
Aileen! Thanks for joining and more importantly for you and @Noah_L's support of Product Hunt. Today we launched Product Hunt Podcasts, so I'm compelled to ask you: what podcasts are you listening to? 😀
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@rrhoover goooo team PH! i am kind of a podcast newbie - was late to discover Serial and still discovering. recently listened to kara swisher's re/code decode, TED radio hour, A16Z podcast, and also listen to storynory podcasts and audible (listening to tales of narnia right now) with kids when i have them in the car...
Ray Garcia
Ray Garcia@raygcreative · Founder @teleporme
@aileenlee I am a podcast junkie and listen to about 8 hours of podcasts a day. Some of my favorite include the @jaltucher show and also @patflynn at the smart passive income podcast. Love the addition of Podcasts to PH, @rrhoover .
Corley
Corley@corleyh · COO @ Product Hunt
Hi, Aileen. Thank you for taking the time to join us today. You've had a very diverse career - how do your different experiences shape your perspective? And what is one of your most valuable lessons that you find yourself applying regularly?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
Hi @corleyh! Wow that's a deep one - some quick initial thoughts: 1) i'm from am immigrant family - my dad's side of the family was very poor in China and they went thru a lot to make it to the US and build a life here. My mom's side was a little better off but she came to the US with no family and no financial support. I feel a huge amount of gratitude and obligation to work hard and make my family's hard work worth it 2) like many people i've not really had a master plan but been fortunate to get opportunities to work with great people in growing companies, and figuring stuff out along the way 3) developing and listening to your gut is one of the things i am always trying to work on, among many other things...
Shaan Puri
Shaan Puri@shaanvp · ceo, Monkey Inferno
Hi Aileen, How do you feel about the way 'unicorn' has gone viral? If I recall correctly, you were the first to use that term to describe $1B+ companies! -shaan
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@shaanvp hey Shaan - see above - getting a little behind on answering q's so will try and add / circle back to this later if i can! (and thanks!!)
Ben Tossell
Ben Tossell@bentossell · Makerpad.co
@aileenlee Hey Aileen! Thanks for doing this. What would you say are some startups that are essential to attaining Life 2.0? And which products do you use on a daily basis to improve your life?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@bentossell thanks for the first question! i'm super psyched to be doing this. Products i use in my "life 2.0" routines - Twitter; Accompany (sorry, still in private alpha :)); Evernote; Spotify...Waze; One Kings Lane; Streak; August Smart Lock; Uber & Lyft are just some of themmm
Michael Cho
Michael Cho@michael_cho · Cofounder, YAM
Hi @aileenlee thanks for doing this! What's your advice for startup entrepreneurs with young family (my baby boy is just 9 months-old and my wife has her own startup)? How do you balance work/family, given your experience as mom of 3 and VC work life?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@micoolcho - not sure if i have good advice - my husband is cofounder of a startup (renovo motors) and i'm working on CV, we have 3 kids, a dog, chickens, dead goldfish ... it requires decent planning / time management / communication skills but so many families do this daily juggle and they have way less resources than we do, so i assume we have it easy relatively speaking?
Michael Cho
Michael Cho@michael_cho · Cofounder, YAM
@aileenlee oh no! poor goldfish! you're right my wife and i are already very fortunate...just have to make it work somehow between the 2 startups and the baby boy :)
Sean Green
Sean Green@disruptart · Founder, ARTERNAL
Hi @aileenlee thank you for taking the time to do this. For a B2B SaaS startup looking to get introduced to you and your team, what is the best approach? And, what metrics (MRR, traction, etc) are you looking for?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@disruptart as you have likely heard/read, a warm intro from someone who knows us and knows you is usually the best way to get introduced. we do read cold inbounds though at hello@cowboy.vc mamoon from S+C partnership has a great slidedeck on Saastr about key SaaS metrics - would check that out in terms of what kinds of metrics SaaS investors (including us) are looking for - although we invest mostly at seed so our metrics are usually earlier or non-existent :)
Jon Sutherland
Jon Sutherland@jmsuth · Just a lefty pushing pixels and code ✌️
@aileenlee Thanks for doing this! What products do you use for productivity (tasks, projects) in your personal and work life, and where do they fall short?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@jmsuth i/we use Accompany, Streak, Google for Business, Evernote, Slack....
Irina Jordan
Irina Jordan@irinajordan · Director of Inbound Marketing
@aileenlee From one mom of 3 to another, how do you instill entrepreneurial spirit and drive into your kids? Thanks!
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@irinajordan i'm not sure we are - please let me know if you have any suggestions!
Irina Jordan
Irina Jordan@irinajordan · Director of Inbound Marketing
@aileenlee We tap into what they love doing and let them try to monetize it: e.g. yoga, piano, selling drawings online:).
Hey @aileenlee what are your favorite books?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@alfink92 wish i spent more time reading 'long form content' :). Like to read a mix of non fiction and fiction. right now reading Judd Apatow's book of interviews & comedians - and huge fans of Tina Fey, Mindy Kaling books which i recently reread :)
Justin F Harris
Justin F Harris@justinfharris · Co-Founder, Beehive
@aileenlee Thanks for doing this and two questions for you. With your experience at Odwalla and NorthFace I was wondering how do you think social media and the voice of the digital consumer is changing product and brand marketing? How early should entrepreneurs connect with Cowboy Ventures to share their progress and connect with your team?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@justinfharris ha when i worked with North Face and Odwalla, social media didn't exist! imagine that. we invest in seed and seed-extensions so would get in touch with us early, but probably not so early that you're just noodling over an idea and haven't done anything about it yet...
Emily Snowdon (née Hodgins)
Emily Snowdon (née Hodgins)@emilyjsnowdon · Operations @ Product Hunt
Hi Aileen! Thanks for joining us today 😀What one moment is the most memorable of your career to date and why? Thanks!
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@ems_hodge ack not sure i can boil them down to just one! but being there to unveil the pre-launch Segway to luminaries like Steve Jobs and Jeff Bezos definitely is on the list as very memorable :)
Adpreneurs
Adpreneurs@adpreneurs · Founder of Adpreneurs (Make Shit Happen)
Hey @aileenlee thanks for taking part in the AMA, I remember reading that you thought immigrants play a huge role in the founding and value creation of today’s tech companies. With what's going on with the refugees globally, and the attitude towards immigrants etc, are you a) doing anything about pointing to the facts on what they could offer/benefit the country - aka Merkelfying the tech industry b) are you more inclined towards international influenced founders?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@adpreneurs not sure if i know what Merkelfying tech means - but guessing we as an industry are probably not doing as much as we could to push the powers that be to make it easier for immigrants with relevant skills work and stay in the US to drive innovation. we are inclined to back a diversity of founders - many studies show more diverse teams have better results on a number of metrics :)
Jack Smith
Jack Smith@_jacksmith · Serial Entrepreneur & Startup Adviser
@aileenlee Hi Aileen. When it came to raising the first fund for Cowboy, what sort of investors did you target (e.g. maybe it was mainly university endowment funds)? And why did you target those sort of investors?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@_jacksmith i was very fortunate to get great advice from other seed investors who had done LP fund raising before me - they mostly said that university endowments can be kind of conservative and also many are too large to write a $5m check which is what we were looking for as anchors in CV I. I'd also run sales before as a startup CEO so knew that upfront 'lead qualification' was important to hopefully minimize time spent on leads that unlikely going to close. Our investors at Cowboy did wind up being mostly institutional - a mix of great endowments, fund-of-funds and family offices, plus a select number of individuals.
Jack Smith
Jack Smith@_jacksmith · Serial Entrepreneur & Startup Adviser
@aileenlee cool, thanks for sharing
Hey @aileenlee. Greatly appreciate your time. Your portfolio is consumer focused. What are your own views around the customer experience that your portfolio companies create around the customer? Do you factor that into your investment decisions? Thanks so much! ps. love your logos that appear at the top of your website (zebra, bird, elephant, etc). any symbolism there? :)
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@m1lesv actually we're about 55/45 consumer vs entreprise investors - and for both we love to back founders who are obsessed with the customer experience. Slack (wish we were investors) is probably an easy example of an enterprise co that is likely obsessed with customer experience - and yes for consumer companies we look for founders who can talk to their vision for the brand and customer experience. (and ps thank you love our logos too. we wanted something that showed the spirit of the west & pioneering + we care about products, creativity, imagination, and have a sense of humor - so an androgynous cowboy/girl riding on a giant magical / lucky animal like an elephant or koi fish was it! helena seo did a fantastic job)
Brian Shultz
Brian Shultz@brianlshultz
@aileenlee - In this live chat, you advised to take academics more seriously. I was hoping you could reflect on your time at HBS and how it has made an impact on your life (career, personal development, etc). Thank you for taking the time to answer questions today.
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@brianlshultz ha that was just for me - not sure if that was advice for everyone else :). I know bschool nowadays if you're already in silicon valley might be a tough call - i was coming from living in Shanghai studying chinese and teaching english, and previously in investment banking, so business school was a great way for me to build a new set of learning & relationships, and transition into a new career. it was life changing!
Carlos Jaramillo
Carlos Jaramillo@cabad79 · Fundador Krecr
Hi, Aileen. Thank you for your time. What can you recommend for a person that is trying to enter the VC Business? What to focus? And how to get the best from the investments?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@cabad79 hi Carlos - the VC business is really small, possibly shrinking - so there isn't a clear career path. might look at some of the backgrounds of folks who might be similar to you and figure out what their path might have been? and working at and doing a great job at a VC-backed startup where you get a chance to work with the investors seems to be another path.
Frank Goortani
Frank Goortani@frankgoortani · LastCall.cc
Hi Aileen, What future fields most interests you for startups? In other words, what types of startups do you see yourself investing in in the next two years? Thanks!
Erik Torenberg
Erik Torenberg@eriktorenberg · Former Product Hunt
Hi Aileen! Welcome :) What advice would you give to your 25 year old self? Alternatively put, if you were 25 in 2015, what would you pursue and how would you think about career development?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@eriktorenberg when i was 25 i think i was about to start bschool. my advice would likely be to go out and work out a little less and maybe take the academics a little more seriously! :) but seriously - there were some fantastically smart and interesting people in bschool and one regret is i didn't spend more time getting to know some of the people who were more introverted and a little harder to get to know initially, there are some people i've gotten to know since then who turned out to be amazing people and friends who i didn't slow down enough to get to know back then.
Alex Carter
Alex Carter@alexcartaz · Operations @ 60dB. Ex-PH Podcasts 😻
Hi @aileenlee! As many are aware, I believe you coined the term "Unicorn" back in 2013 (http://techcrunch.com/2013/11/02...). Fast forward to 2015, I'd love to hear what new thoughts, reflections or insights you have about the term, and how you think it's impacted ecosystem (for better or worse). Thanks!
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@alexcartaz thanks for the question! it's funny yesterday i read a post by a friend in VC who wrote why he "f**ing hates unicorns". It's funny the word has come to mean much more than i think any of us expected. There is so much going on in tech right now - brutal competition, talent wars, huge opportunities to improve on cultures, inclusion and diversity, overspending/burn rates too high -... and some people attribute these things to unicorns which feels like a reach and a serious over simplication. Most entrepreneurs, team members and investors since the start of venture capital that i can think of have been hoping to found, back or be part of companies that scale and become long term titans of the tech landscape, and i don't think that's going to change. that's what i was interested in when working on the unicorn analysis - understanding what's under the hood of companies that could be on a path to be in that place.
D 0'clock
D 0'clock@d0clock · RedHare
hi aileen! outside of the tech / vc / startup space, which companies and CEO's do you regard the most highly and why?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@d0clock there are non-tech companies? ha just kidding - not sure i've studied companies outside of tech enough to give you a good answer unfortunately
Mathias Adam
Mathias Adam@madgraphism · Senior Design at @Balckpills
Hi @aileenlee, Thanks for chatting with us. I know you are a music lover, but are you a music maker or composer?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@madgraphism sadly no - have played piano, clarinet, guitar, bassoon (differentiation strategy - was not 1st clarinet in high school but was always 1st (and only) bassoon, ha) in my life and not been great at any of them.
Jacob Wallenberg
Jacob Wallenberg@jrwallenberg
Hi Aileen! I'm very interested in marketplaces, and I'm curious how you see this sector developing. Is it possible we're reaching a point where the product/service-categories of sufficient size and frequent use have been targeted, and most inefficiencies have been removed? Or are there any specific ones that you think have yet to be properly addressed?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@jrwallenberg hi! i doubt it. Assume there will always be 'creative destruction' - new companies come along to challenge incumbents, and do things in a more delightful / efficient way.
Nadav Raviv
Nadav Raviv@livenadav · Former founder & CEO @ Link Big ltd.
Hi @aileenlee :-) As an immigrant, how can i pitch to VC when they strictly ask for a local referral? (Tnx. Startup nation guy)
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@lovenadav hey see my reply above - we take 'cold inbounds' at hello@cowboy.vc but referrals work better in our experience. finding great connected advisors / mentors / legal counsel or being part of an accelerator program if you don't have great local contacts can be a reflection on an entrepreneur's hustle...
Luup
Luup@luuptv · CMO, Luup
Hi there! Thanks also for doing this - super cool. Curious to know when you think it's a good time for start ups to pivot and why? Thanks, Stu.
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@luuptv hmm if the team is feeling like what you're working on isn't working - customers don't love the product/service, aren't using it and/or the economics are just terrible, and that isn't likely to change with the capital, team and time available - could be a good time to rethink?
Steven W
Steven W@mrwongsteven · Nice guys finish lunch.
@aileenlee I read somewhere that start-ups who are seeking funding should not search for VC but instead position themselves to be found. What's your take on that?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@mrwongsteven i haven't read that! feels very zen, but not so practical maybe?
David Chie
David Chie@davidjchie · CEO, Palo Alto Staffing
Hi @aileenlee Thanks for joining this chat. It seems at the moment it's easier than it has been in the past for startups to raise money. Do you think that raising from an AngelList Syndicate vs. a more traditional seed VC impacts the ability to attract talent?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@davidjchie it might be easier than ever to raise seed, but it is getting harder to raise A, B, C and D. teams need to to think about that longer term game - this might be a horrible analogy and Noah is probably going to cringe at this - but raising seed is like getting to the field and having enough water and supplies to play an inning or two, the game hasn't really started yet :)
David Chie
David Chie@davidjchie · CEO, Palo Alto Staffing
@aileenlee @davidjchie very good point! thanks!
Mike Hince
Mike Hince@zer0mike · Freelance UI Designer Founder Howler.co
@aileenlee Cowboy Ventures is a really great name. For startups (like PH) growth is a key factor for funding. I'm interested to find out just how much growth you would need to for your pitch to stand out above the rest? ✌️thx
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@zer0mike hi Howler founder! really depends on the category / business - but for most companies, mo/mo organic growth is a very useful metric and depending on the base, 20-50% mo/mo growth can be good - retention, referral, churn are all things we look at too.
Elaine Lu
Elaine Lu@elaineluyi · Co-Founder & CEO, Visbit Inc.
@aileenlee Hi Aileen! Thanks for having this conversation with us! May you give some advices for female founders specifically? Any strengths and weakness you'd like to remind them to be aware of? Thanks!
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@elaineluyi hi elaine - i was fortunate to speak last week at a Watermark event, not sure if it's on video but we talked about this some. Because most venture investors are currently mostly male, if / when you are pitching to male investors do think you should assume there will be some differences in how they perceive female entrepreneurs. In my experience, female investors need to know their #s well, and not be perceived to be overly confident/ over stretching, and yet also be confident, yada yada... walking a bit of a finer line in my opinion than male founders, imho.
Earteza Auvee
Earteza Auvee@earteza · Team Member @Foundedx
@aileenlee Hey Aileen! This is Earteza from Bangladesh . Do Cowboy Ventures have any interest or any plan for Bangladeshi Startups ?
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@earteza hi Earteza - we only invest in US-based startups, sorry :(. Because we invest in mostly seed stage companies and like to be hands-on, we find it's much easier to work closely with companies when there aren't huge time zone or geographic distances, plus our networks of relationships - for help with hiring, customer intros, expertise etc - are mostly in the US.
Gillian Morris
Gillian Morris@gillianim · CEO, Hitlist
@earteza follow on to this one - how often do you invest outside the Valley? What are your arguments for being in/around the Bay Area?
Earteza Auvee
Earteza Auvee@earteza · Team Member @Foundedx
@aileenlee @earteza Oky Understand. Hope see you guys soon in Asia
Earteza Auvee
Earteza Auvee@earteza · Team Member @Foundedx
@gillianim @earteza yes , but there are lots more startups coming from Asia. If anyone can get the Indian Market that will be huge . 1.28 billion people's market .
Arpit C
Arpit C@irhymeth · Community and Growth at Integromat
Hi Aileen, thanks for doing the AMA. Under life.20, would you include products/services that don't completely rely on an app/smartphone? I'm talking about a service which can be availed without the use of an app or even a smartphone. Although it can be availed through an app also. Thanking you in anticipation of your answer!
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@irhymeth possibly! we don't invest exclusively in 'life 2.0' companies... but we do invest mostly in companies that are building new products & services that make life better for the user/customer whether they are a consumer or a business user - because they allow new/better capability, insight, efficiency, selection, fun, delight etc.
Erik Torenberg
Erik Torenberg@eriktorenberg · Former Product Hunt
Let's all give a HUGE thanks to @aileenlee for taking the time to chat with us, and for all her support to PH and the broader entrepreneurial community.
aileenlee
aileenlee@aileenlee · Cowboy Ventures
@eriktorenberg and the whole PH community - thank you for being a part of this, really appreciate all the great questions, honored to be here.
rwpr
rwpr@rwpr2
Hi Aileen, appreciate that you're doing a live session with Product Hunt. What is your advice to younger women out there who are deciding to make a career transition to another industry? Thanks!
Tuan Le
Tuan Le@tuanl34
Hi Aileen, What do you think is the future of sharing economy (i.e, what would the Internet 4.0 looks like, as some people now define Uber and AirBnB as Internet Marketplace 3.0?) Particularly, do you think well-funded startups which are trying to disrupt the local services space and become "Amazon for Local Services" (e.g: TaskRabbit, ThumbTack, Handy, Porch, HomeAdvisor, etc) can ultimately disrupt established online + social directory like Yelp or even CraigList? Plus, what is your thought on how the recent moves of Google and Amazon into this space would impact the valuation of those private startups, if any, as well as whether the startups in local services would have good enough business models to sustain from the heated competitions of Google and Amazon. Finally, do you think this market would be "a winner takes it all," or there would have to be several players dominating, as the pie is too big for a single company to swallow? Thank you for your time in answering this lengthy question!
kiki
kiki@maggiedorispie · Director, Yuniki
Hi Aileen, thanks for doing this session. Have you ever had a point in your career where you've felt out of your depth and how have you over come this?