I'm talking career, work life balance, and my path into investing – Cat Lee, Investor at Maveron & former Head of Culture at Pinterest.Featured

catcatcat·Sep 24, 2018·83 replies

Hi I’m Cat. I’m an angel investor, passionate about investing in companies for and by women. I’m also taking a 6-month sabbatical from the working world to travel (Antarctica, Easter Island, China, etc.) and learn new things (learning Chinese)!Previously, I was Head of Culture at Pinterest. Over the last six years, I wore many hats at Pinterest. Before taking on culture, I led Global Partner Marketing and was our first Head of Growth. I helped scale Pinterest from 25 million to more than 100 million monthly active users, and I helped the organization grow from 40 to over 1300 employees. Before joining Pinterest in 2012, I worked on the Facebook platform team starting in 2008. I have an MBA from University of Michigan and a BS in Computer Science from Stanford.Ask me anything about angel investing, traveling, company culture, product growth, marketing, building and scaling a team, or something else! It’s my first AMA (*super nervous*), but I’m excited to engage with this community! I’ll be in Taiwan and about to depart for Singapore when answering your questions!

catcatcat·Sep 28, 2018·4 replies

Hi All - Thanks so much for all the wonderful questions. I did my best to answer as many as I could before I arrived in Singapore, but unfortunately, couldn't get to them all! This was a lot of fun! Thank you to Leap for kicking off this wonderful series! ♥️🙏 ~Cat

zari·Sep 28, 2018

Your answers have been a treasure trove - we're so appreciative! Thank you @catcatcat !!!!!

cadran·Sep 28, 2018

Thank you so much for all the incredibly thoughtful replies. I'm so glad we had you here to kick off the series.

galbendor·Sep 28, 2018

Thank you @catcatcat for sharing your experience and insights, this is incredibly valuable to us enterpenuers. Enjoy Singapore and the rest of your travels!

daniella·Sep 28, 2018

Thank you so much Cat! There are so many great insights in there I will be bookmarking!

rhondacollins·Sep 24, 2018·1 reply

Can you say more about how you helped scale Pinterest from 25 million to more than 100 million monthly active users. Anything that might be useful for startups scaling from 1,000 users?

catcatcat·Sep 26, 2018·2 replies

Hi @rhondacollins - Thanks for your question! Answered a similar question above (see here)A few other specific things that come to mind:* Understand the people who love your service/product today. How did you get to 1000 users? What do you believe are the key drivers of their engagement and how have they come to hear of your product? How do you get more of them? Directly engaging with your most active users often provide valuable insights on how to grow. In the early days of Pinterest, Ben & Enid engaged directly with our Pinner community and kicked off a "pin it forward" campaign with SF blogger, Victoria Smith (https://www.sfgirlbybay.com/2010/05/12/this-time-lets-pin-it-forward/). At launch, Pinterest was invite-only and grew by word-of-mouth through the blogger community. As we scaled beyond invite-only, we worked closely with user research to uncover new opportunities to provide more value to users and to grow faster.* Be disciplined in measuring and understanding your growth strategy and metrics. Develop a consistent framework/dashboard for tracking growth. Break down your growth funnel and as much as possible, make it easy for everyone at the company to have context and understand the key growth drivers. * Create a culture of learning and moving quickly. It's important to have every team member understand the key priorities, outcomes/goals you're hoping to achieve and principles behind all decisions. At Pinterest, having this info meant anyone could propose/set up/run an experiment (a template guided your thinking -- early screenshot here: https://imgur.com/a/55qzVS4) and make a call. Create a system/cadence that enables quick learning, communication and action. * There were several key moments & levers that impacted our growth from 25 million to 100 million monthly actives: (1) Launching our mobile apps -- within 24 hours of launching our Android, iPad and 2nd iPhone app, Pinterest's mobile traffic eclipsed our web traffic. (2) Investment in SEO as an acquisition and re-engagement channel. (3) Hundreds of experiments across the signup process, onboarding flow, email, and notifications. (4) International. Localizing topics and home feeds by market. Happy to dive further into any of these areas if you'd like more specifics!

julietoberding·Sep 26, 2018

Hi Cat,Thanks for taking the time to answer our questions.I'm interested in more specifics on frameworks for growth in an early startup where users are in the double digits and you want to move to the 1000's:"Create a framework for growth and know your numbers cold -- what is the one or two metrics that matter? how do they relate to other metrics? Make it easy for everyone to have context around these metrics."Thanks so much for your time.Best,J

jadashapiroboober·Sep 29, 2018

Thanks for this info! As we are working on my startup, boober, to scale up after matching 1000 families to same-day, in-person lactation support, this information is relevant and helpful!

amy·Sep 24, 2018·1 reply

Hi Cat! Thanks so much for doing this AMA - your background is a fascinating startupy mix: CS + MBA + Metrics & Growth + People & Culture + Angel!How did you decide to move from being Pinterest's head of growth to being their head of culture? What would you say were Pinterest's biggest 'people' challenges and how did you tackle them? Was there anything that you had a vision for changing that you couldn't get institutional buy-in for, and what was your biggest People accomplishment there?Also - what were some of the small but impactful things you did in the early days of Pinterest's growth that might be actionable for all the early-stage founders here on Leap?

catcatcat·Sep 26, 2018·1 reply

Hi Amy! Thanks for the questions!My career choices within Pinterest (and Facebook) have always been guided by a combination of opportunity, where I could deliver the highest impact, and where I would continue to grow. My move to culture was prompted by a conversation with Ben (Pinterest's Co-founder and CEO). We had a discussion about culture and some of the challenges that we were facing as we continued to scale into a global organization with 1000+ people in over 13+ office locations. My passion for our culture and his encouragement won me over. He shared that he thought I could apply the unique context I had as an early employee (joining as an early product manager at ~35 people) and what he saw were my superpowers (positivity, naturally embodying Pinterest's brand values, and getting stuff done) to be the caretaker of our culture.In this role, my primary focus was to understand our culture and bring more intentionality to everything we do:* what do we value? * how do we work together? * how do we make decisions?* who do we hire? * what makes people successful here? My playbook? Build bridges. Get curious. Take action.Regarding institutional buy-in, there weren't too many roadblocks that prohibited me from taking action and trying new things. I had built a lot of relationships/goodwill over the years by working across many different teams at Pinterest. I had great partners within our People/HR, Internal Comms, Brand, and Leadership teams to work with. In addition, there was context shared about the role (announced to the company by Ben and I had a lot of autonomy reporting to our co-founders).Some of my personal highlights while serving as Head of Culture:* Partnering with our user researcher and people analytics teams to "study us" and better understand our culture -- Learned a lot from over 60 qualitative interviews with our employees across tenure, function, location, employee surveys and over 30+ meeting observations* Working with our leadership team on "faster, better decisions" to communicate decision-making principles* Hosting our bi-annual hackathon (aka make-a-thon) with Pinners (involving a Pinners' choice award bringing to life our values of "Put Pinners First")* An even bigger and better Knit Con that included our Pinners. There may have been a surprise Hamilton flashmob that I helped orchestrate (what is Knit Con? see here: https://newsroom.pinterest.com/en/post/dont-just-talk-about-culture-live-it)* Partnering with our People team to kick off our first career event, "Future U," along with workshops on "Designing your life," giving people the opportunity and time to explore and more purposefully charter their work/life journeys.* Weaving in culture into Q&As (e.g., Pinterest's 8th bday with pinner stories and early employees sharing their favorite memories)* Measuring connection to our mission at Pinterest. We asked, "Are you motivated by Pinterest's mission to help you discover and do what you love?" on the quarterly Pulse survey. This metric was greater than 91% and increased quarter-over-quarter.One big learning for me is that at a certain scale or size of company, working on culture initiatives is like making long-term investments. You may not see the impact right away and while there are early/anecdotal indicators, it's way harder to measure the true impact of each initiative (unlike many initiatives on growth & revenue). Finally (whew!), small but impactful things I did in the early days of Pinterest's growth that might be actionable for all the early-stage founders here on Leap:* Cultivate a "one team" mentality. Clearly communicate & repeat the mission, strategy and goals of the company, and how growth impacts those goals. Connect the work that your team does day-to-day to what the company is trying to achieve.* Trust and empower your team to make decisions quickly (and without you)! People had a good understanding of the key priorities, well-defined outcomes and clearly communicated principles behind all decisions. Anyone could propose/set up/run an experiment (a template guided your thinking) and make a call. Create a system that enables quick learning, communication and action.* Understand what provides value to users and where users struggle/are stuck (sometimes this is better achieved through primary qualitative research vs. just looking at the data/user flows)* Create a framework for growth and know your numbers cold -- what is the one or two metrics that matter? how do they relate to other metrics? Make it easy for everyone to have context around these metrics.* Stay hungry and curious. Our team shared a Pinterest board with growth articles & tips. I also spent time meeting with other growth teams and experts (and having them visit our teams). We learned valuable lessons from these conversations!

carolinewells·Sep 26, 2018

Wow such a dense treasure trove in this response. Going in the Evernote archives stat. I think so many organizations could benefit from a "head of culture," and this is a roadmap for what the role could entail if you're trying to get buy in from the top. Thanks so much for your time and insights, Cat!

lauraspiekerman·Sep 24, 2018·1 reply

What are some things you think are critical for early stage companies to do w/r/t fostering a healthy culture? (For context: we're 11 people, seed stage)Any exercises you've found particularly helpful?

catcatcat·Sep 26, 2018·2 replies

Hi @lauraspiekerman - Understand the culture that exists today and the culture you want to encourage. Culture is the word that describes “who you are”— everything from your talents, your behaviors, your collective identity, and the unique way you work together every day. Culture can largely be summarized by answering these questions:* what do you value?* how do you work together?* how do you make decisions?* who do you hire?* what makes people successful?To get at these answers, it's helpful to have a discussion with each employee using questions like:- Why did you join?- Describe your best day/your worst day.- What keeps you here?- How much does the company's mission resonate with you personally? Why or why not?- What are your company’s core values and how much do they apply to the work you do everyday?- Who embodies the culture? Why?Find light-weight ways to continue to check-in on your culture and bring the best aspects of your culture to life everyday (e.g., monthly discussions, quarterly employee surveys, weekly Q&As, all hands, events, etc.)A few articles/videos as additional resources:* "80% of your culture is your founder" (http://firstround.com/review/80-of-Your-Culture-is-Your-Founder/)* "Making culture a tangible metric" (https://blog.ycombinator.com/making-culture-a-tangible-metric/)* Lecture 10 (YC Startup School) (https://www.youtube.com/watch?v=RfWgVWGEuGE&feature=youtu.be)* Culture and Revolution (https://a16z.com/2017/03/04/culture-and-revolution-ben-horowitz-toussaint-louverture/)* My Culture Pinterest board: http://pinterest.com/catcatcat/culture

TanyaM·Sep 26, 2018

This is GREAT information! Thank You!!!

lauraspiekerman·Sep 26, 2018

Thanks, Cat! This is awesome.

hollyster·Sep 24, 2018·1 reply

What are things that you did to help make the culture real at Pinterest? What is the #1 influence on culture at Pinterest?

catcatcat·Sep 26, 2018

Hi @hollyster! I recently gave a talk this summer at Culture Summit titled, "Culture in everything you do"* video: https://www.youtube.com/watch?v=aonwePCBLyI&list=PLwywuptFlm-KO6SVJRxdF79ylI73vvAr_&index=12&t=0s* slides: https://www.slideshare.net/CultureSummit/culture-summit-2018-culture-in-everything-you-do-107472783Bringing a culture to life/making it real is somewhat similar to my work on the growth team and thinking about the user journey within your product. Being intentional about the employee journey and how the person interacts with your company when they first hear about it from their friends, when they join, when they onboard, how they engage/hear what's going on, and when they leave summarizes the ongoing work of a culture team. Several initiatives (big & small) brought our culture to life. One of our goals was to strengthen each person connection to Pinterest's mission (Help you discover and do what you love) & values (Put Pinners First, Knit, Be Authentic, Go). Tactically, that translated to:* Creating a set of consistent, shared experiences & environments that touch everyone who is contributing to the company. We had weekly live Q&As, quarterly company-wide meetings (called "Progress"), and an annual event where we celebrated our culture & creativity (Knit Con: https://newsroom.pinterest.com/en/post/dont-just-talk-about-culture-live-it)* At these moments, our mission was repeated. Ben started repeating the mission & why it matters, every single week, every single all hands. Ben & Evan often shared why the mission matters to them personally. Ben asked his leaders to do the same within their teams and soon enough, managers began doing this. It created a norm and encouraged people to have a personal connection to our mission.* Putting Pinners First. Every Q&A would close with a Pinner story (about how someone used Pinterest) ranging from the epic to the everyday. While we each can't get to know our Pinners personally (as we used to in the early days), the sentiment was brought to life/continued to scale through these stories. It also helped us feel a sense of pride in seeing how our work day-to-day tied to the lives of everyday people around the world (and humbled us when people had issues with Pinterest). We also invited Pinners to our launch events, our make-a-thons (hack-a-thons), and Knit Con. * many, many more....According to our initial research (we studied "us"), a huge influence on culture was our co-founder and CEO Ben Silbermann along with our most visible leaders. Not surprising. As a result, this role initially reported into the CEO and I spent a lot of time helping our leaders become more aware of how their actions (or non-actions) signaled cultural norms. People also cited Knit Con as the one of the cultural highlights or what made Pinterest's culture so unique.

Jiwon·Sep 25, 2018·1 reply

I am a startup founder (by woman) and my question is how do we find an angel investor who has a right fit and high potential to invest in us? Any optimized process to find the right angel investor for a startup?

catcatcat·Sep 26, 2018·2 replies

Hi Jiwon - Good question and one that I often hear from startup founders. Unfortunately, I don't know if there is a truly efficient/optimized way to do this. If there is, I'd love to know! Generally, finding the right fit is finding an angel investor who deeply resonates with you and/or your company. I always recommend finding investors who are most familiar with you/your team/your work. Here are other resources to try when seeking angels:* AngelList profiles: Most active angel investors keep their AngelList profile up-to-date. * Find well-connected & helpful angel investors. They often know of other angels who they can introduce you to. * Contact angel hubs (e.g., #Angels, Broadway Angels, Pipeline Angels, AngelTrack, Sequoia Scouts, YC Startup Investor School, XGooglers) who can often connect you to angels that are looking to invest in companies like yours* VC Wiz (don't have any firsthand knowledge of its utility, but looks useful): https://vcwiz.co/* Women in Venture list (https://docs.google.com/spreadsheets/d/10LkI_0WmVJHBR68F2eah8hqnHIk2x60YCot0K8wOu40/edit#gid=1049644618)Best of luck in fundraising. I'm happy to help and connect you with any angels in my network who might be relevant! Other founders or investors on Leap - Please contribute! I'm sure you have much more to share on this topic than me!

Jiwon·Sep 26, 2018

Cat, thank you so much for the response along with sharing the links. Very helpful. I didn't know there are so many other than AngelList. Yessss!!! I would love to ask for your help with connecting to the potential angels. If it is not too much, I will follow up with you with a brief company intro. Thanks again!!

mylegoel·Sep 26, 2018

Hi Cat!Thanks for all your time and generosity in sharing your advice and resources. I'm sifting through all your responses to apply what I can to my startup venture :-) Also, to add to your list, some other angel investor resources are 1000angels (I think US only) and Keiretsu Forum (global). I watched the CoFounders Lab Webinar today on funding your startup and Erica Duignan, Managing Partner from 1000 Angels, was on the panel (https://www.linkedin.com/in/ericaduignanminnihan/). She was super helpful. 1000 Angels https://www.1000angels.com/Keiretsu Forum http://www.keiretsuforum.com/Thanks again for all your time and great advice. Happy Travels!

michie·Sep 24, 2018·1 reply

What are the things that you are interested to invest on?What matters to you the most -- is it the founders, the idea, their location, their metrics (user/revenue), or something else? How much do you usually invest on one startup as an angel?

catcatcat·Sep 26, 2018·1 reply

Hi @chi! Thanks!As an early angel investor, I'm passionate about exploring and supporting companies by and for women. I've been really inspired by the AllRaise, #Angels, Backstage Capital and other women already doing this (and I hope to contribute to their efforts)! My vision is to see more multi-billion dollar companies founded by women and run by women. I think that vision starts with more people wanting to angel invest/fund companies by and for women and more founders wanting to close the #Gaptable. This article also fueled my fire (http://fortune.com/2018/01/31/female-founders-venture-capital-2017/).My broad criteria: People > Market > Product. I believe all of the best companies start with amazing people that have a personal connection to the mission. Something I ask is if I would be willing to drop everything and work for the founder(s) at this company full-time. Part of my thinking is because in my career, I've chosen to work at Facebook in late 2007 and Pinterest in 2012 (both cases over other similarly staged companies). Definitely a lot of luck in making these choices, but it ultimately came down to picking people & missions that resonated with me (and where I could do the most meaningful work). Outside of the business/investment fundamentals, this sentiment is similar when I'm making an angel investment. As an early angel investor, I typically invest $10k-25k and hope to do ~5 companies/year.

michie·Sep 26, 2018

Thank you so much for doing this @catcatcatThat's really is amazing that you are doing this for a cause. You made me smile just by reading your answer.Have a safe travel!!! :)

cadran·Sep 24, 2018

Hi All – as a reminder – This is our first AMA in an ongoing series with experts in our community.

lynne·Sep 24, 2018·1 reply

First off, good on you for taking some time to learn Chinese! (It's been a TODO of mine for... well... my whole life 😂)I have two separate sets of questions for you:1. What were some of the initiatives that you led as Head of Culture (and how big was Pinterest during the time)? 2. What do you think most startup employees fail to understand about their equity?

catcatcat·Sep 28, 2018·1 reply

Hi @lynne! Thanks! Let me know if you'd like tips on learning Chinese or ever want to partner up to practice!1. Covered a lot of this in earlier answers here and here2. Many startup employees often lack the understanding of how to value their equity.

stephanielu·Oct 22, 2018

Hey Cat, if you swing by Shenzhen or Hong Kong, let me know. I'm fluent in Chinese and happy to help practice, feel free to add me on Wechat at "lusteph." +I'm also an UM alumn, go blue! :)

theresarapior·Sep 25, 2018·1 reply

What did you want to grow up to be when you were a kid? What moments in your life led to where you are now, and, would you say you've 'made it'? Is there any general advice you give to people that you'd want to share here?Enjoy your travels!

catcatcat·Sep 28, 2018·1 reply

Hi Theresa - I told my kindergarten teacher that I wanted to be "She-Ra (Princess of the Universe)" when I grew up and specifically, dye my hair blond when I turn 40. Well, I've already done the latter so I'm ahead of goal. 🙂When I think about the many moments that brought me to where I am today, I'm proud and happy. I don't really think about the concept of ever "making it" because once I've reached a goal, I tend to set new ones and love the feeling of progress. I'm grateful that I've had wonderful experiences, am healthy and have the freedom to take this time off to travel. However, there's still a lot more that I see myself learning, a lot more to accomplish, and a lot more experiences to have.One piece of advice that was shared with me and currently resonating is to "Just be (yourself)" It took me a while to figure out what it meant to be me vs. what other people expected of me. Some things that helped me is working with an executive coach, reading lots of self-help/business books, meditation, and journaling. Can start a whole new thread on this topic!

theresarapior·Sep 28, 2018

She-ra yeeeessss well I'd say you hit that goal, too :D thanks for sharing your insights <3

Morgaine·Oct 09, 2018·1 reply

How do you handle cultural differences when it comes to inclusion and diversity? I'm working with a company that has a big presence in Paris and the US, but the views from SF to Paris are very different. Especially when it comes to race, age, and general diversity. They are all amazing people, but it's been a challenge to launch ID projects. Is there anything you suggest? Or thought you might have?

cadran·Oct 10, 2018·1 reply

Great question! Unfortunately the AMA has already ended. I do think this would make a great separate post on Leap though.

Morgaine·Oct 10, 2018

Haha I didn't look at the dates of the posts. Apologies! I'll make a seperate post :)

cadran·Sep 24, 2018·1 reply

Has taking a sabbatical had an impact on how you’re thinking about your career?

catcatcat·Sep 25, 2018·1 reply

Taking a sabbatical has had quite an impact on how I think about life as well as career! First, going on a sabbatical was something I was initially scared to do. It felt unconventional and maybe even a bit selfish(?). But I felt at a crossroads in my career and life. I'm 15 years into my career, 10+ years at high-growth companies (Facebook & Pinterest). I've had great opportunities, proud of what we've built, but wanted something more and felt I had more to give. On a personal note, I was also unsure if I wanted to have kids. Thanks to friends, family, and some planning, I found the courage to take the time for myself to figure it out. Hence, sabbatical.I'm grateful for having time away from the day-to-day-hustle to be more introspective, to read more, and have the opportunity to try new things. So far, it's given me the space to revisit my personal values, time to spend with the people I love, and the freedom to follow my curiosity. The time off has allowed me to reflect on who I am and what matters to me. It's allowed me to explore where to best contribute to make a positive difference in the world. I'm looking forward to a career where I can continue learning and helping others succeed. A bit vague I know, but I'm giving myself until January to let the world know what I'll be up to!

Rgbx·Sep 26, 2018

This makes me incredibly happy to read. I took a sabbatical from my last job, which led to my startup idea and ultimately quitting my full-time. I think the best thinking happens when we free up our time to think and reflect!

leighhoneywell·Sep 24, 2018·1 reply

Do you have a thesis or topic focus to your angel investing? I'm also curious how you think about deal flow - how do you source investments?

catcatcat·Sep 28, 2018

Hi @leighhoneywell! See answers above here and here.Regarding how I think about sourcing investments, I've learned that there is no one right way and that every successful investor has a different approach when it comes to sourcing. Some investors are incredibly thesis-driven and others are opportunistic. To date, I've sourced my existing investments in two ways: activating my existing networks and participating in events, programs, and forums to broaden the community of founders that I interact with. Sourcing also becomes easier as you meet and help others because they often refer you to other great people. I try to be useful given my skills, experiences, and resources. So far, it's only led to good things.

ighernati·Sep 24, 2018·1 reply

Thank you so much for doing this AMA. A lot of what makes a company successful depends on many factors. For example, I am in Ed tech and i see a lot of Angel women saying that Ed tech doesn't make money. Ed yech is 10 years behind the tech boom. We know that schools move slower than other tech company. But now schools have WIFI and Chromebooks and it's about time to have some unicorns in Ed tech to change a little. What are you thoughts on this market? What metrics do I have to show in order to be taken seriously. The market is huge but very fragmented. Thanks

melaniebanfield·Sep 24, 2018·1 reply

I have the same question. Specifically about growth projections to capture attention. I want to be realistic.

deenaminwalla·Oct 02, 2018

I would have loved an answer to this as well

caitlinscott·Sep 25, 2018·1 reply

It's amazing that you took on so many different roles at Pinterest. I currently work in social and content at an early-stage startup, but I would love to work on partnerships and event marketing in the future. What is your advice for making a move to a new team within your company? How did you prove you were able to take on a new challenge? Thank you! Enjoy your trip - it sounds fab!

catcatcat·Sep 28, 2018·1 reply

Hi @caitlinscott! There's a lot to cover on this topic. Some general thoughts (not knowing any specifics): * Share this goal with your manager. Most managers will want to learn more and help you do your best work/achieve your career goals. * Learn more about partnerships & event marketing. Meet with people on that team and understand the challenges and what skills are needed. Chat with people who do it really well at other companies (especially at a later stage than yours). * Find ways to work on projects with that team. Let the team's manager know that you're interested. If it's a fast-growing startup, chances are there will be plenty of opportunity.Other resources:- "Designing your Life" by Bill Burnett and David Evans (https://designingyour.life/)

caitlinscott·Sep 29, 2018

Thanks so much, @catcatcat!

raquelaraujo·Sep 24, 2018·1 reply

I was wondering what made you go into a more People role (like Head of Culture) coming from a STEM background, and then Growth and Marketing? Would you say that you fell into that role? or did you seek it?Also, how did you decide to become an angel investor? Was it from your role as head of culture that you felt you wanted to improve things from the top of the funnel?

catcatcat·Sep 28, 2018

Hi @racquel! More about how I ended up as Head of Culture in an earlier thread here. Regarding stepping into the role of Head of Growth, I saw a challenge/need within the company and I raised my hand to help tackle it. As for how I decided to become an angel investor, I covered my motivation here. Once I decided to start, I tried it out by first reading a lot of book/blogs and listening to a lot of podcasts about angel investing. Then, I participated in YC Startup Investor School and got into First Round Capital's first AngelTrack cohort. While doing it part-time, found that I really enjoyed it and decided to spend more time angel investing.

annieta·Sep 24, 2018·1 reply

When Angel investing, how do you think about investments not by or for women? Are you strict about how you think about other companies?

catcatcat·Sep 26, 2018

Hi @annieta! Thanks for the question! I evaluate all opportunities in a similar manner using 3 broad buckets: People, Market, and Product (in that order). While I'm most excited about supporting companies by and for women, I'm also looking at companies founded by all genders and ethnicities. I'm still honing/refining my investment thesis and criteria. So far, I'm using frameworks that I've learned and collected from various angels. My goal is to take a consistent, disciplined and principled approach with my decisions and become a better investor over time!

hollychessman·Sep 24, 2018·1 reply

Were there ever times you felt held back or treated differently because you were a woman? If so, how did you deal with them? Also, do you ever experience imposter syndrome? If so, what do you do to get past it? Thanks again and safe travels!

catcatcat·Sep 28, 2018

Hi @hollychessman! Yes, there are many times that I've felt treated differently as a result of my appearance. I often discover it much later when people are kind enough to share the assumptions they've made when they first meet me. I've dealt with these moments in a couple ways. First, tried to become more aware of how I was being perceived and proactively worked on debunking a lot assumptions in evaluative situations (e.g., first impressions). Second, I try to over-prepare and focus on the goal. Third, I've also become more comfortable with communicating/following up if I've been misjudged.Imposter syndrome -- yes, definitely! Some of the things that have helped me:* Find your cheerleaders. I've been lucky enough to have a partner, friends and mentors who often "loan" me their confidence. * Do things that scare you. I was recently inspired by Shonda Rimes, "A Year of Yes." Tame that voice inside your head! I took improv classes through SF Bay Area Theater School (bats.org). Improv greatly helped me stop overthinking things and improved my confidence.* Meditate. Found the tracks on Calm (especially around relationship with self & loving kindness) grounding.* Finding more comfort in vulnerability. Brene Brown covers this topic in depth. Her books were enlightening in helping me comes to terms with being OK with not imperfection.* Read more about & talk to people who've been there/done that. Feeling more prepared always helps me feel more comfortable applying my skills to new areas.* Now, my mental trick is to channel my inner Beyonce and to do these exercises to take up more space (https://www.ted.com/talks/amy_cuddy_your_body_language_shapes_who_you_are#t-806422) when I need to summon up more confidence.

Zahra·Sep 25, 2018·1 reply

How can I get angel investors like yourself to be interested in investing in Startups in frontier markets? I'm working on launching a venture fund in Iraq.

keturahovio·Sep 25, 2018

I'm also interested as well

tgoyal·Sep 25, 2018

I really admire your career at Pinterest and now how you are taking your experience to angel investing. I am currently raising a small angel round and have a team that I am trying to keep motivated with sweat equity and a great team experience. That being said, sometimes there are lows that I go through as a founder where I still have to motivate my team. Are there any tips you have on being able to keep up the momentum up for your team even during times that are more stressful during the early stage raises?

whitneyosei·Sep 25, 2018

Do you have any general tips for scaling a marketplace?

pennydaily·Sep 25, 2018

Appreciate you doing this for all of us. What a neat idea Leap came up with.We are having a lot of roadblocks when it comes to investors because we are the first full female owned cannabis tech company and we are NOT technical founders. However, we have an incredible remote team and adding in another co-founder just for "show" seems like nothing more than a distraction for us right now.Is it plain crazy for us to expect investors to recognize just how difficult it is to lead a remote team, perform all research testing(cannabis-we are therapist), all design, and all the business side? Meaning that they would understand we know what we are doing, we just aren't coding efficiently? We are currently in classes to code Swift but we won't be done for at least 6 months with that.We appreciate any advice you might have about communicating that effectively.Grateful for your help.

nettadobbins·Sep 25, 2018

Hi Cat! My name is Netta and I'm the CEO & Co-Founder of Minorities in Media Connect (Mimconnect for short -- mimconnect.com). We're an emerging HR-Tech and social networking platform connecting the world's diverse media professionals to each other and providing a bridge to jobs, freelance opportunities, resources and more -- increasing economic opportunity for previously marginalized groups. I have a couple questions regarding Company Culture. What's your best advice for building a company culture at a startup? Things are ALWAYS changing and what you told your team Monday may no longer be applicable Tuesday. How do you keep their spirits up and trust in you high when things change so rapidly? Also, what are your thoughts on how transparent you should be with your team? Lastly, how much equity would you recommend for your first team members? Have you seen deals that didn't involve equity but we're equally as impactful?Thanks for your help and I look forward to hearing your answers! Netta

Suja·Sep 24, 2018

How did culture impact growth at Pinterest? What is the most important aspect ( if you have to choose one) you look for when investing?

jenr·Sep 25, 2018

In regards to growth, what's something you wish had been done earlier at Pinterest to boost growth? On the flip side, is there something that could've been avoided that hindered growth? Thank you so much for your time!

ketakideo·Sep 25, 2018

Thanks for doing this AMA!1) What is the biggest diversity challenge you have faced in your career?2) What are the key things a company must consider to get their culture right?

daniella·Sep 25, 2018

It's great to have you as our first AMA guest! Your growth numbers are incredibly impressive, but would you be able to advise on your initiatives to engage and retain such a huge, varied user base?

venikunche·Sep 25, 2018

Hi Cat, Thank you so much for doing this AMA. Could you please talk about how one does Partner Marketing. Are there are any resources that I can read to learn? I am a software engineer and I am working on a startup to help underrepresented people in tech get jobs. I've been given the advice to partner with other organizations. However, I am having a hard time figuring out how one does that.

keturahovio·Sep 25, 2018

I'm currently in Nigeria. I'm building an inventory management system for SMEs in Africa. I'm looking to raise a seed round for my business for us to achieve pmf. However, I'm wondering how to go about getting warm introductions to see stage investors in the US. Any advice and would you consider investing in companies outside the US?

a0z0ra·Sep 28, 2018

Given a choice of 2 teams - everything else being equals (market etc) - which one would you invest:1) Team without good credentials, first movers and very good tractions (pass PM Fit)2) Ivy Leaguers, new to market, before tractions

Latrice·Sep 25, 2018

Thanks for making yourself available to the Leap community! Very excited about this AMA series and to engage with you. I have two questions.1.) For very early stage startups just thinking about first team members, what advice do you have to share about culture/ How should early stage startups be thinking about culture at this point?2.) Do you have any lessons learned from your personal experience, or lessons learned from your observation of startups as an investor, to pass along to us as it relates to common missteps founders make in acquiring customers?Your trip sounds fantastic. Enjoy!

TamiWilson·Sep 24, 2018

First, thank you for taking the time to field our questions.Second, so jealous....Easter Island. Definitely one of my first loves is anthropology. Easter Island is one of my “must see” places.Finally, when you look at your investments or potential investments...how much weight do you put on the age of the founders? By that I mean, is there an optimal age of founding teams that VCs like to fund. What about location of the startup? Or Non-tech founders leading tech businesses? This information helps us to prepare if these are questions we would address when pitching. I don’t believe any are barriers, just minor issues that we may need to address. Again, thank you and enjoy your travels and your sabbatical.

TanyaM·Sep 26, 2018

My question is: In your opinion, what are the most important slides in an investor pitch deck?

FayeMTomar·Sep 26, 2018

Me and my husband has this startup we've been working on for nearly a year now. I just want to know how do you think we can boost our user acquisition for a social media app? Thanks!

laurenmhastings·Sep 26, 2018

What would you say is the best way to get the attention of an angel investor?

adelaidadiazroa·Sep 25, 2018

Hi Cat! We just launched our app last week (a social travel network that notifies you when your travel plans overlap with your friends' so you can plan to meet up) and since we're still bootstrapping and a small team I'm having a bit of difficulty figuring out how to best spend my time, there are a lot of product improvements that can be made to encourage more sharing and adding of trips so that users will see the value but there is also getting the word out through marketing. I think encouraging 'virality' within the app is very important and am just wondering if you think focusing on that might be the best way to spend our time right now or now that the app is out start focusing on marketing more. Is there a ratio you'd recommend on time spent on product vs marketing strategies for this stage? Thank you so much, and yay for your sabbatical! I also took a 6 month one and it definitely had a huge impact on my life :) (it's also where I found my new business partner and came up with this idea!)Adelaida - www.nomo-fomo.comPS: So excited to read all of your answers here soon :) I have a few screenshots from your Founders Network presentation a few months back, it was so helpful! <3

juliapaulescu·Sep 25, 2018

I have a few questions for you:1. What do you wish you knew when you started your career?2. What was your greatest challenge at Pinterest and how did you overcome that challenge?3. What are the top 3 most significant lessons you learned throughout your time at Pinterest? Thank you for taking the time to do this! :)

marinafilina·Sep 26, 2018

I've got a question about an acquisition of first active users. Our startup is a mobile application for nail polish lovers and it's rather hard to make a community of users who make an original content there (I mean swatches, reviews etc.) We've got several users who are really involved and I communicate with them. But the most part of our customers are silent and not active. Do you know how Pinterest got the most first users?

manasvi·Sep 25, 2018

I'm building a platform for companies to hire candidates with culture fit first, by making it measurable and so am very curious to know how companies actually define their culture? Isn't it very subjective like everyone would say it is collaborative, give first, empathetic and so on! How does a company really measure it?

justirma·Sep 24, 2018

I was interested in two different parts of your experience. 1) In what ways or situations did having both an MBA and a CS degree help you at Facebook and at Pinterest? 2) How did you land at Pinterest? And what did you do to help you land in a Head of Growth position?

kriscorz·Sep 24, 2018

How did you learn about investing? Were there people/workshops/books you'd recommend?

jessicagrayson·Sep 24, 2018

What do you think were the most critical product changes at Pinterest to help Monthly Active Users sky rocket?

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