2018 Life Audit and Year Review 🗓

As I look back at the end of 2018 I reflect with gratitude on the hardest and most tiring year of my life. In 2018 I took a sabbatical, tried my hand in investing, formed a consultancy, lived bicoastally, went through my own heart of darkness journey, fell in love, moved to Brooklyn, and started a new job at Bravely. Events don’t mark life — it’s the memories and lessons that serve as meaningful milestones and we can only connect the dots looking back. Joan Didion wrote about how our memories are unreliable. What we thought, at the time, was important ends up only being blip in our timeline and what we dismissed as trivial often affects us in magnitudes.

While looking back on my 2018 recap of memories and major life events I stumbled across the following themes:

  1. Sometimes you have to fail to know what you want
  2. Fewer genuine connections win over many superficial connections
  3. Build your tribe
  4. Sit and breathe through your discomfort
  5. Growing up is letting go of what no longer serves us

Sometimes you have to fail to know what you want: my journey into MicroVC

I’m a stubborn and strong-willed person so when given the gift of time during my sabbatical I decided to pursue what I’ve wanted for a long time — invest in underserved founders. In the last seven years through my writing and speaking on diversity and inclusion, product management, and liberal arts thinking many founders have come to me seeking angel investments. The deal flow I saw came from diverse founders who didn’t feel like they fit into the Silicon Valley mold. The founders who approached me often were women and underrepresented minorities attempting their first startup. There was a blind spot in the market. It seemed like the right timing to attempt my own fund in light of SV’s purging of bad actors (Justin Caldbeck and Dave McClure et al.), I wanted to test out my thesis that we should bet on more product-minded diverse founders.

Many people told me it was dumb for me to raise money especially investing in diverse founders. They told me I can’t raise money without an institutional investment track record, they told me it is impossible to reconcile social impact with a prove economic model, and they told me to go work a VC firm instead of create my own model. I ignored such advice.

I wanted to create a fund targeting diverse minded product founders dedicated to humanizing technology. I flew to SF every three months to fundraise. I had dozens of pitch meetings with LPs and founders. I was promised half a million dollars from AngelList that never actualized (Arlan Hamilton spoke out about this in the StartUp podcast). I tried to make it on my own without AngelLists’ money burning through my savings before realizing that the microVC game is financially impossible for those who don’t have a financial safety net.

You don’t make salary for years and your management fee is 2% out of whatever you raise for the lifespan of the fund. 2% out of $1M is only $20K over two to three years before you go out and raise another fund. It makes sense why people who raise their own funds do it after they have exited because they have the luxury of not needing income for years. In order to make more income you need to raise larger amounts in successive funds in order to pay yourself larger management fees. VC in a nutshell is a fundraising game. More money raised equals more hits and more luck service area. The best investors don’t win on merit but rather fundraising and more hits. I thought through strong will, grit, and intelligence alone I could raise enough money and crack into the VC world. I wish I had been prepared for the harsh realities of LPs being skeptical of investing on a social mission or betting on underserved founders (women and POCs). I wish I had read Elizabeth’s Yin’s blog post about the harsh realities of raising a microVC fund. But sometimes you have to try something and fail to know what you want. But I don’t regret trying.

After eight months working on the Product Fund I didn’t close on my $10M target demo fund. I missed the tangibility of willing nothing into something, I wanted the clear inputs to outputs ratio I loved in product management, I craved working on a team, I craved operating. I am a builder at heart. I loved the mental gymnastics of investing but hated sitting on the sidelines watching companies grow. I wanted to roll up my sleeves and get dirty again so I went back to product with stronger convictions, beliefs, and values.

Fewer genuine connections trump many superficial connections

During my eight months of microVC I met over 80 VCs and hundreds of founders. You never know when a coffee meeting or lunch will yield anything but a genuine connection goes a long way. In a transactional world where time is money and every opportunity cost calculated, I learned in VC that building fewer but real, genuine connections based on shared values and principles is more important than building thousands of superficial, transactional relationships. Some would argue I’m crazy for not “spraying and praying” but I do believe that cultivating deep, genuine, authentic connections differentiates one investor from another, one human from another. It’s the long game that matters.

The most surprising conversations came from unexpected encounters. My Twitter fam supported me during the darkest and lowest times. I was deeply inspired by the philosophical mind of Kanyi Maqubela who told me to shift my perspective and look horizontally to see a multitude of options lie before me. Steve Schlafman and I co-supported and collaborated on our respective funds. I learned a great deal during Office Hours with Steve and Bo meeting NYC founders, hearing their pitches, and offering tactical advice and coaching.

Build your tribe

It’s only during hard times do you truly discover who your true friends are. I wrote about cultivating authentic friendships in Silicon Valley after leaving my job at SigFig and losing my work identity. A winnowing process always happens during precipitating events in life. Major life events separate the wheat from the chaff: real ride or die friends from the fair-weather friends. I use to be so sad about parting connections bonded by convenience, shared lifestyle, work — too attached to let go of what no longer served me. However, after many life pivots later, job changes, and heartbreaks I’ve learned to let go of friends who can’t bond over hardships, know struggle, or share common values and beliefs. If we were to never change then we would still be friends with the same people from third grade. In a way, I think the evolution of friend groups — not the complete dissolution of all groups — is a good marker for personal growth.

Sit and breathe through your discomfort

During my last trip to SF I took my first Kundalini yoga class at my old studio. Kundalini is a school of yoga dedicated to breathing exercises which activate dormant energy in your body specifically the spine. It’s considered one of the most potent and dangerous forms of yoga because it helps you tap into repressed emotions, your subconscious, blocked energy, and psychosomatic symptoms. During my first class at Laughing Lotus I experienced the discomfort of breathing so hard that my throat became parched and my legs cramped up before falling asleep. In the middle of a kriya (breathing exercise set) I felt the sharp, painful realization that making the career pivot to VC, ultimately, wouldn’t make me happy, or solve my problems. After months of vacillation, it was a strong moment of clarity. My legs began to go numb and I felt an upwelling of emotion rising from within. The emotion that poured out of me was the physical manifestation of “I’m not enough”. I had lived so much of my life proving other people wrong, accomplishing more, and reaching the next goal in the pursuit of enough. So much of my identity had been shaped fighting for my independence, overcoming biases, and reacting to microaggressions. I always pursued more to prove to others and myself that I am enough. But the constant pursuit of more accomplishments, shiny titles, brand affiliations, wealth meant nothing if I didn’t believe and feel at my core that I was enough. Looking to external validations and social reinforcement would never fill my own well. Since that class I’ve been actively writing “I am enough” on my mirrors, saving the mantra on my phone screen, and practicing the tenets of Marissa Peer’s talk.

I don’t think practicing Kundalini yoga proved anything I didn’t know. But, it did teach me to sit with discomfort and not take action. I had to breathe through my emotions, activate years of repressed memories and feelings, and just sit with it.

Growing up is letting go of what no longer serves us

2018 was the year I started to exorcise my greatest demon — anxiety. Anxiety has been with me my entire life. It’s what makes me great and pushes me to constantly achieve and do more. I channel my anxiety into productive discomfort but it’s also a crippling force in my life. At the trough of my fundraising I became an insomniac awake at 4am with a sinking sense of fear and loneliness.

My anxiety is a double edge sword. She is what makes me ME in so many ways. I plan ahead, risk mitigate, and anticipate the worst case scenarios as to avoid them. But she has also hinders me for trusting a good thing when I see it. Falling in love and coexisting in a healthy relationship for the first time in my life has helped me to trust and not lean into my anxiety. The overactive mind of mine helps me write a whole blog post in one sitting when I have a good story in me but at the same time it is what causes me crippling self-doubt, impostor syndrome, and anxious negative downward thinking spirals. Sometimes my anxious thoughts are so real that I choose to believe them over reality.

I’m learning to face my anxiety with more honesty, vulnerability, and fortitude. Instead of leaning into her, I challenge my anxiety, I tell myself “I’m doing that thing I always do where I think X is going to happen…” I to react less to my anxiety. I choose to take a walk and look at the colorful leaves on a tree in Madison Square Park instead. I try to take a couple steps and breathe. I choose to breathe and do a sun salutation in the bathroom. I choose to tell people when I’m feeling anxious as to not hide my anxiety any longer. My anxiety is a part of who I am but it does not define me. My anxiety is what helped me get to where I am but she is no longer serving me. I thank her for the extra motivation, productive discomfort, and bid her farewell because she no longer serves me.

May you let go of what no longer serves you in 2019.

May you sit and breathe through your discomfort in 2019.

May you build your tribe in 2019.

May you cultivate more genuine connections in 2019.

Thank you Joshua Fulfs, Zane Shannon, and Reggie James for the encouragement and editing of this piece ❤

— bosefina

Product-focused investor empowering underestimated founders. Writer. Advisor.