Elpha AMA with Cat Lee, Angel Investor and Former Head of Culture at Pinterest

by Cadran Cowansage10/1/2018

I’m the founder of Elpha, an online community for women that is built by and for women. You can read more about Elpha here. Usually conversations on Elpha are only accessible to our members, but we wanted to experiment with making some conversations available to everyone. We’re kicking off this experiment with a 6-part AMA series.

Here is our complete lineup:

  • Cat Lee: Angel Investor & Startup Coach. Former Head of Culture, Partner Marketing and Growth at Pinterest.
  • Linda Xie: Co-founder & Managing Director of Scalar Capital.
  • Jess Lee: Partner at Sequoia, Previously Co-Founder & CEO of Polyvore.
  • Anu Hariharan: Partner at Y Combinator’s Continuity Fund.
  • Aygerim Sauletkhan: Software Engineer at Apple.
  • Emily Weiss: Founder and CEO of Glossier.

Here are a few excerpts from our conversation with Cat Lee. You can read the complete AMA here.

Hi I’m Cat (catcatcat). 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!

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

catcatcat: 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!

hollychessman: 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: 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 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 when I need to summon up more confidence.

Amy: 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 Elpha?

catcatcat: 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).

Read the rest of this answer here.

rhondacollins: 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: Hi @rhondacollins – Thanks for your question! I answered a similar question above (see here).

  • 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.

Read the complete answer here.

chi: What are you interested in investing in? 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: 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.

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.

Read the full conversation on Elpha.


  • Cadran Cowansage

    Cadran Cowansage is a software engineer at YC.