Hi friends,
It's been seven months since my last newsletter. I was speaking to a friend last night about how I don't feel like the internet is a safe place to publish anymore. She was encouraging me to write more and publish more. To her chagrin, I explained to her how I can't be as open and vulnerable on the internet anymore. I am nostalgic about the days when you could write and publish into the void without a slew of trolls, misinterpretations, and criticism. I've been thinking a lot about the term "calculated vulnerability". I've seen a lot of my peers write after the resolution of a something hard (overcoming an illness, shutting down a startup, IVF etc) after a happy ending, neatly packaging their vulnerability in a bow. But what if that happy ending doesn't come? Do you just stay in a purgatory? Do you just stay in silence? I've been wondering about what my "resolution" will be so I can start publishing again. This self-imposed hiatus is basically me waiting for a satisfactory resolution in order to start writing again.
Today I've decided to start writing again without a resolution. I want to remind myself why I started in the first place. I published my
first Medium post about my hair falling out in my first PM job as a catharsis. I write in order to remind myself that I'm not alone in my struggles. My first post resonated with others who were also struggling as first time PMs, experiencing a sense of otherness in their tech jobs.
Today I'm writing to you from that same place where I started, writing for relief. I didn't imagine I would be here a year ago. A year ago, I left my job at Tumblr to pursue the world of venture capital. I gave myself the gift of time to pursue my passion and intellectual curiosity in venture. I wanted to help ecosystem change. I wanted to prove an investment thesis that would reconcile social good with economic gains. I wanted to allocate capital to underserved founders. I wanted to prove people wrong when they told me it would be impossible to fundraise money as a solo first time partner. I went through a slew of VC interviews as a "token hire", each time more disillusioned. I've sat through countless meetings with GPs (general partners) that ended with the words "Let's keep the conversation going." I've had married investors hit on me while giving me career advice. I tried to start a fund with AngelList as an emerging fund manager but they lied about the half a million dollars I would be allocated (Arlan Hamilton openly spoke about the fall out in the StartUP podcast). I flew back to SF five times in the last six months. I tried to enter into a long term partnership with someone but that didn't work out. I became an insomniac and my anxiety triggered a social withdrawal and mental breakdown. At my worst, I started to retreat from friends and family until I would start feeling "better" and that spiraled into a three month long depressive spell where I binged on Gossip Girls (a very good show btw). My heart problem relapsed due to stress. I thought that if I kept going, meeting new people, and fundraising that I would catch a break. I failed. There I said it. I failed in starting a fund. I failed in fundraising $10M. I underestimated how rigged this system is against new agents. At the end of the day, venture is a fundraising game. It's not about how good of an investor or operator you are, it's about how deep inroads do you have to deep pockets. I learned that hard work and not giving up is not enough in this space. I learned that being an evidence-based thinker works against you in a purely relationships world. I failed in taking care of myself and focusing on my own health and wellbeing. I failed to listen to my inner voice when it told me that my inner self was morally incongruous with everything around me. I failed at extricating myself from a miasma of hopelessness, blinded by ambition and hunger.
It's hard for me to admit failure because I'm not very good at giving up. My dad told me that he knew VC wasn't right for me but he couldn't tell me otherwise because of how willful and stubborn I am. Up until now, when something doesn't go my way I just double down and work harder until I will it into the right outcome. I think this is why I enjoy PMing--I love shaping and molding reality with all its complex variables into what's in my mind. Now I'm learning to unwire my brain and learn to walk away from things that are no longer serving me. Learning when to quit is just as important as persisting but society doesn't tell you to "give up". In fact, I think this whole advice about "don't give up" is bullshit for people who are persistent. We should be telling people to walk away more often from situations, relationships, jobs that are no longer serving them. I want to be a
better quitter in life.
Growing up is realizing which parts of you have gotten you this far and no longer serving you. We all have maladaptive parts that have benefited us up until a certain point. I'm trying to identify and discard the bits and pieces of myself that are no longer necessary. I think it's easy to become accustomed with discomfort, upstream effort, pain, and suffering. At my lowest point as a solo entrepreneur I remember telling myself that it's suppose to be hard, rationalizing the pain and suffering. I told myself that if it was easy then everyone would do it. I was so lonely and disillusioned and yet I still kept going because everything I had achieved in life has been based on upstream effort. Yet, at what point is something
too hard? At what point do you walk away? For me, it was a wake up call when I started getting chest pains, heart palpitations, and shortness of breath--the VC life was literally killing me because my heart was failing.
Living life in 2-D is measuring your self-worth based on the tangible value and output you create but what about the third dimension of life? What about all the things you can't show with money, status, and things? I've been thinking about how since moving to New York I have nothing to show tangibly about my own growth but I know inside that the delta between SF Bo and NY Bo is huge. That delta is a new dimension and vast expanse in my life where creative pursuits intersect with chance encounters--where serendipity and magic happens. Society has such a good ruler for success but we don't have an alternative metric for measuring an examined and fulfilling life. Lately, I have been feeling a sense of loss about the conscious and unconscious sacrifices I have made along the way for success. 22 year old Bo didn't imagine how much I could accomplish by the time I turned 30 but I also feel so behind in other parts of life. My sense of collective loss is hard to put into words. This Medium
post by Katie Thurmes on life after entrepreneurship really resonated with me. I love how she talks about living a three-dimension life, making space for people you care about, embracing downtime, and letting mind and body return to its natural rhythm--all things I've neglected for too long.
In an effort to grow more holistically, I'm starting a section in my newsletter about things I love, food for thought (readings), and companies/brands I believe in (investment opportunities).
Things I love:
- I've been loving this
UMA oil at night. In an effort to turn off my brain, I dab a bit of this oil on my wrist and inhale before I go to sleep. It's a love this nightly ritual.
-
TiroTiro Floreo earrings: I picked up these shiny babies at the West Coast Craft fair in SF last month. I've been following Teresa's jewelry making journey for years. I love the evolution of her concentric semicircles into a more polished and elegant aesthetic. She's a badass single mom living in Portland, OR.
-
Kosas 8th Muse Blush and Highlighter Compact: I screamed when Sheena sent me this to try out with her entire line of products. I have to say this cream blush makes me never want to go back to powder again! The highlighter is a more natural milky shimmer than the Glossier Haloscope. I've been a Kosas fan girl since day 1 and love Sheena's vision for minimal clean beauty. They just raised their
Series A funding too!
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Shine is a daily mindfulness app I use in the morning instead of meditating. It's a conversational bot that texts you in the morning with words of affirmation, thoughtful articles, and audio clips! They just raised their
Series A funding as well.
Food for thought:
-
Downstream Effort TED talk: a wake-up call for me on how tap into downstream effort to achieve your goals
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The Hidden Pleasures of Life by Theodore Zeldin: 28 philosophy essays about the questions in life you have a 5am with a friend. I love Zeldin's incisive intellect and critical commentary on modern society. I would love to grab dinner with him one day and just pick his brain!
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Einstein by Walter Isaacson: I found a signed first edition of this book in a free box of books in Soho. It was kismet that brought this book found me!
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The Artist's Way: how to tap into your creative force and recapture your sense of childhood wonder again.
Companies/Brands I believe in:
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Are.na - I'm excited to be joining as an advisor to Are.na! They just closed their
seed round on The Republic. I love how Are.na is both a productivity tool for thinkers as well as a social network. It reminds me of early Tumblr when you could find a safe space on the internet without distractions. I'm excited to be helping the team with growth and product best practices. I highly recommend this collection on
Yuppie Dystopia.
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SkinAllies: My friend Nu founded Skin Allies to help women and men find effective, clean, and scientific skincare products. They are a science-backed company that focuses on curating new emerging clean beauty brands. You get a monthly subscription box tailored to your skincare issues. I'm impressed by how thorough their questionaire is down to your zip code and sun exposure. They are also
fundraising their seed round on The Republic.
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HoppStudio: these are the most comfortable and shoes ever! I love Eree's one woman shop based in Brooklyn. I own four pairs of her shoes. She makes me realize that comfort and fashion are not mutually exclusive.
So what's next for me? I'm returning back to my PM roots with stronger convictions, values, and morals. I am a builder who wants to work on problems that have widespread social implications. I'm not longer searching for the next sexy project or company. I want to work with good people, plain and simple. I want us to move away from the "time spent model" to "time well spent model". I want to regain my trust for mankind again. I want to wash away my disillusionment and return to a glimmer of the blurry-eyed-22-year-old in San Francisco with a sense of possibilities. I want to remember why I started.
Until soon,
--bo
