An Ode to Those Who Came Before

Those who met me when I got my start in venture almost 6 years ago, probably remember the bright eyed bushy tailed Sydney. Back then, I told everyone who would listen that I was intent on starting my own fund one day. I initially said that it would be within 2 years of my venture career, then 2 years became 3, 3 became 4 and eventually the itch to start something of my own dulled into a feeling that most days I could forget, if I didn’t think about it too much.

What I realize now, was that as I uncovered the complexities required to start a fund, I got scared about what wanting more for myself would cost. Scared that I couldn’t build the type of fund that I wanted to authentically, scared that I would make a mistake, scared that it was all too much for me to take on.

That changed in 2020.

The reckoning that venture underwent that year and in the years since cannot be understated. White women, Latinx people and Black people are launching a new generation of new funds, and every few months it seems, a new barrier is broken. Getting a front row seat to this radical shift has been a privilege. From the first $1B Black owned fund to the largest woman founded firm, the world is changing in front of my eyes and the “no limits” mantra is truer than ever before. Additionally, since 2015, the barrier to entry in venture has continued to fall – thanks to organizations like Carta, Angellist, Flow, Allocate, Recast, Raise, Bridge, Coolwater, Strut and others – and I am watching new entrants do things their own way. The stronghold that the old (white) boys club had on the venture ecosystem is loosening.

The movement gave me so much hope and pushed me to think critically about what I wanted in my venture career again. Once I started leading my own deals and working directly with founders who I admire, the flicker in my belly officially transitioned to a flame. I was so inspired by them! The founders who I get the privilege of working with are putting their livelihoods on the line to build new institutions that serve the communities they care the most about. Why aren’t I doing the same?

I’m so excited to reimagine what is possible for myself once more. #LFG

Who I’m Supporting on Giving Tuesday

Giving Tuesday is one of my favorite days. I remember running campaigns for it when I used to work in non profit at The Fund for Public Schools. It is a great day to think about opportunities to invest in your neighborhood and community. To that end, I wanted to surface the nonprofits that I have a monthly subscription to with the hopes that it will help others learn about them and get inspired to subscribe to a nonprofit that is doing work that they care about.

Chapter 510 – I learned about this organization while I was at the OMCA visiting their Afrofuturism exhibit. I loved Chapter 510’s focus on helping children dream and create art.

Capital B – I am a Pre-Seed investor by day, so it’s only right that I give to a nonprofit who is still in pre-launch phase. I love the vision for what they’re building and think that it is urgently needed. A safe and accurate place for news created by and for Black people.

Oaklandside – Really love reading the writing of amazing journalists like Azucena Rasilla and Ashley McBride who both keep me up to date on what is going on in Oakland and keep me grounded in the historical context of it all.

NPR – I recently did a review of the podcasts I listen to and almost all of them are NPR produced. Invisibilia, Rightnowish, Planet Money… I’m especially a huge fan of the work KQED is doing to elevate the voices of marginalized folks.

I’m also really grateful to be on the board of two non-profits who I also think are doing great work and I want to shout them out here too!

Colorwave – They are helping Black and Brown people access technology careers that many previously thought were unattainable by giving cohorts access to community support and technical training. I wish I had something like Colorwave when I was first transitioning into tech!

Project Include – They are helping the tech industry become more inclusive through research, training and accountability. It’s led by the inspirational Ellen Pao. Their most recent report on discrimination against disabled people was powerful – I learned so much!

OMCA’s Afrofuturism Exhibit: My Photo Journal

When you first walk into the museum, you are presented with this photo on the wall. What a powerful image! I had seen this photo a few times in advance in some of their publications and the IRL version did not disappoint. What does this image conjure for you? For me, it reads like a promise. A small whisper that says, “don’t despair too much, I promise you that you will survive.”

After waddling around a bit to find the special exhibit and finding out some really intriguing information about California’s history with impressionism, I finally found it. The main event! When you walk in, you first hear the sound which might have felt amplified because it was so dark. The first piece of artwork you are presented in the music. It acts beautifully in concert with a chalk based mural on the wall. The second thing you encounter is non other than the grandmother of Afrofuturism herself, Octavia Butler.

A few new things I learned about Octavia Butler during this visit:

  1. She is from California like me!
  2. She left this one journal entry that I hadn’t seen before. I love the focus on intensity and think that it’s something you feel in her writing. Sometimes it’s so intense that it’s uncomfortable and I think that’s her point.

After you walk past Octavia Butler, you continue to be a part of amazing art. I was honestly overwhelmed by it all and I will have to go back again and again to get the full experience of it. I eventually though walked into a spaceship-like structure and was presented with the following playlist. I continued to listen to it even after I left the exhibit and wanted to share (I particularly liked Tainted Love by Gloria Jones).

I kept walking around and stumbled upon this presentation and I loved it because it reminded me of my own family’s journey. I had not seriously considered us migrants before, but it’s so true we are. What courage it takes to move across the country away from everything you previously knew – particularly in those times. While we moved to San Diego, I think that the same sentiment holds.

This was the last exhibit on the way out of the exhibit and I loved it so much! It was a reimaging of the cable news network focused on Black news created by Black people about Black people. I must’ve sat there for at least 20mins watching. It did not disappoint. I wrote a little bit more about why it didn’t here: https://airtable.com/shrhzzigJpWTNZIGM

As you exit, you’re presented with this message above the wall. I don’t know how you can’t walk of that feeling all of that energy. I cried as I walked out, as to be expected!

If you’re in Oakland, you can check out the exhibit by purchasing tix here: https://museumca.org/exhibit/mothership-voyage-afrofuturism

Birthday Reflections

One of my intentions for the year of 2021, has been to fail more in public. While it wasn’t an official reason why I started to roller skate, now thinking back on it, given that intention, I can’t imagine a better sport to pick up. The entire assignment when learning how to roller skate is to fall often and very publicly. So far, over the past 3 months since I started I have had 1 twisted ankle, 1 sprained ankle, 1 bruised hand, a very bloody finger and lots and lots of other falls that luckily didn’t do much damage to my body, but definitely hurt my pride!

There have been good things too though. Like, I can skate backward now, I am able to do crossover steps and I can stop without just falling down (sometimes!). I am working up to being comfortable enough on skates that I can join the group in the middle of the skating rink (I have learned that there is always one!) that is doing some funky line dance. That is the goal to hit by the end of the year.

This challenge was particularly interesting to me because I grew up a trained dancer and gymnast. I began both of these sports almost at the same time that I could walk so they were natural to me. While dance and gymnastics were both physically challenging and required serious training, I rarely got hurt – I’ve never had one broken bone and rarely got sprained ankles. I tried my hardest not to let anyone see me sweat, never let anyone see me fall, never make a mistake. That is the expectation when you are on stage – to present a routine extremely physically challenging effortlessly, with a smile. I realized only recently how much of that dogma I internalized and roller skating is my way to find my way back.

Happy 33rd birthday to me!

What Happens To Me When I’m the Only

The first time I can remember being the Only Black girl in my class was gymnastics. My parents started me in gymnastics when I was 3 – they were determined to make me the next Dominique Dawes. I don’t remember much about that experience except that I hated gymnastics. My teacher – who was a white woman – was so hard on me. I remember one time when I was probably about 5 or 6 years old, I burst into tears because the teacher pushed me to do an umpteenth push-up. I was tired. The teacher told me to stop crying because my parents were not paying to have me go to gymnastics and cry.

The second time is dance. I have spent more time in dance than any other career in my life. I was a professional dancer from 3-15. Professional means – I spent on average 4-5 hours a day at the dance studio, traveled across the country to participate in competitions and won enough trophies to cover an entire apartment. My entire career at the dance company I danced with, my sister and I were the only Black kids. This meant exposure to extremely harmful language like – a white girl, who was my classmate, telling me that she was Blacker than I because she was better at dancing Hip Hop than I was (!!!) This also meant the mundane things like trying to get my hair in a bun or choosing “nude” tights were more complicated. So I was constantly negotiating with myself and others how I was “allowed” to operate in this space.

The third time  I can remember was in the National Charity League (NCL). It was one of those high society organizations that my mom somehow got me into. I don’t know how because we didn’t live in or near the same zip code as anyone else in the group. The group was all white girls. They lived in North County in places like La Jolla or Del Mar or Rancho Santa Fe ( if you know San Diego, you know these are the rich places to live). I lived in a weird part of the city that was standardly middle income – our neighbors were teachers, doctors and a guy who ran a dog sitting place (he was the coolest!). NCL became a place where I turned into a full-time observer because it was made clear that I was an outsider – most discussions inevitably turned to conversations about friends of theirs who went to the same Montessori middle school. So at every NCL event, I felt like the purpose of my presence was to be their audience.

Throughout college, I was the “only” a few times. A few classes at Duke, a semester abroad in Scotland, nothing really to write home about. And after college graduation, I went into the public sector where I was surrounded by an amazingly complex set of people who came from all walks of life. It’s only recently that I realized how rare that is. In the public sector, I never really feared for my own safety and I always felt taken care of. It wasn’t perfect (if it was, I’d still be there!) but I think back to that experience as extremely formative and without it I’d never be where I am today. I was forced to consider every angle of every policy – it was invigorating and played to my strengths (I am a deep thinker and love that about myself). And constantly asked to build policies that focused on the most vulnerable first. I loved that work and I was only able to do this deep thinking effectively because I was in institutions that invited vulnerable or minoritized populations into them. I was never an “only”. I was in the public sector for about 5 years before returning to school. I went to Berkeley-Haas for my MBA in 2014.

After business school, the number of times and spaces where I existed as the “only” grew exponentially. I can’t even count the number of times I have been an “only” after arriving on campus. I hadn’t given myself the space to reflect on who I become when I am the “only” until recently and I realized that I should outline exactly what the costs are to being the “only” so that I can remember them and so that others can understand.

Being the Only Black girl in places comes with a set of serious risks. The most significant one for me is – you are highly visible. Visibility is not great because it usually comes with tokenization. An example of tokenizing behavior is when the people around you no longer expect to be held accountable to individual racist acts they perform because hiring you or being associated with you absolves them from any wrongdoing. (to be clear, we live in a country where white supremacy is extremely pervasive, we all need to be vigilant against racist behavior because it is everywhere and in everyone) Instead of receiving protection yourself, you are being used as a shield to protect others around you.

Additionally, when you are highly visible, your moves are more public. Your mistakes are often more public too. You are less able to enjoy the anonymity that is sometimes required for you to have the courage to get back up after you fall down – if fewer people see you fall, there are fewer judges around to tell you how you should get back up. Because most white people live segregated lives, I assume that when I’m the only Black girl in a place, I’m also the only Black girl these white people know. That triggers, for me, a complex layer of processing I can’t fully describe; I feel an intense expectation to then become a representative of my intersectional identity instead of an actual human. A human with human emotions, wants, needs, expectations, worries, anxieties.

Work that inspired this/ vibez with this one:

  1. Economic State of Black America
  2. “We reject pedestals, queenhood, and walking ten paces behind. To be recognized as human, levelly human, is enough.” – The Combahee River Collective Statement. I love this because I think a lot of people think that being “the only” comes along with the assumption that you’re “the best”. I don’t think I’m the best and think there are a lot of people just as great. Why would I want to be somewhere that puts me on this pedestal? And doesn’t putting me on this pedestal just make it easier to fall off?
  3. “won’t you celebrate with me” – Lucille Clifton
  4. Cluster Hires” – I don’t want to offer any broad takeaways or, “here’s how to fix this” statements, but this is interesting research.
  5. Nikole Hannah-Jones’ epic statement.
  6. The work of Heather McGhee. You can check her out by reading her book
  7. The White Space

Meditations on Power

I have a confession to make. I have put this off as long as possible. I have skirted around this admission and have finally decided to own it. Today is the day to announce: I am a powerful woman. And, if I’m honest, I’ve always wanted to be one. I remember being young and just so angry. Angry at the way I was treated unfairly by my dance teachers, angry at my parents for controlling my every move because they were terrified of letting a Black girl loose in this world, angry at my classmates who didn’t seem to understand why I got into ivy league schools even though I had 2x amount of extracurriculars than them and also a better GPA. I was so angry so often and nobody seemed very interested in listening. The most grating (and most common) response I would get to my anger was laughter or some semblance of “isn’t she so cute”.

If I could just get them all to listen to me… I have such important things to say!

So, I devised plans in secret. I would work at a nonprofit for a while to get me closer to my dream of being in politics. Then I realized that those in power at my nonprofit were actually business people! So I decided to go into business. I got into business school, and looked around again. Who, I asked myself, is running stuff here? How do I get to actually have a say? I didn’t have to look far to find VCs. Once I got into the VC world, the question was again, what do I have to do to prove to people that I have something to say? That I have something to contribute? That my vision for the future of business is important?

At the same time, I was also trying to figure out how would I start building wealth. I decided that real estate was the surest path. So I started negotiations early with my Berkeley landlord. After spending $50K+ in rent to him, he will sell me this duplex I’ve rented out for 5 years, right? Right?? Wrong. After this multi-year plan of mine died, I had to start from scratch. I found a house that I fell in love with in Oakland, and after two excruciating months, it was mine (well really it’s the bank’s for a few more decades, but for all intents and purposes, it is mine).

Now, I find myself with decision-making authority at a $100M+ fund, a house, a garden and honestly, a life I always dreamed of. I have more than enough.

Which means, by my own definition, I’m a woman with power. Because I have been so obsessed with this goal in mind, and so consumed by feeling like I didn’t have any, I have probably thought more about this topic than most. How do I honor the trust that people gave me to have this power? How do I not hoard the power I have? How do I create more space for more people to have more power?

And because I am a woman who is so used to feeling powerless, I am not a woman with power who is fearless. I still have a lot of fear. I don’t think I have accomplished anything so far without feeling a healthy amount of fear.

This fear may stem from the fact that I have so many critiques for myself. Before anyone else has something to say about my own work or accomplishments to try to humble me, I have probably already said it to myself. So when I see other people who I think of as whole – not as mythical characters, but real people – and also in power get critiqued by others, I’m reminded of myself. I was and am that person who is critiquing, and I’m also the person in power. It’s a weird place to find yourself in.

I think of this book I’m reading – Cracking Up: Black Feminist Comedy. And so much importance is put on the audience. While the Black woman is on stage, making the jokes, the audience has the power to laugh or boo or be silent. This is particularly true at The Apollo – there was an awesome meditation on it in A Little Devil in America. When we acknowledge that our power is only – as Brene Brown put it – power with instead of power over, who do we become? How do we facilitate meaningful feedback? How do we build trust? How do we forgive even when people have taken advantage of us because they saw us as means to an end and not as humans? How do we shed all of the ridiculous expectations that come with being the first or only and recognize that much of that is a trap created for us to fall into – to become mythologized to the point of no longer being human with flaws, interests and ideas?

Writing inspiration/other people’s work that vibez with this one:

  1. I want to watch this every week honestly. Kathleen Collins is a genius: https://vimeo.com/203379245
  2. I first heard of power with vs power over in a Brene Brown podcast, but this is a more succinct summary of the description: https://sustainingcommunity.wordpress.com/2019/02/01/4-types-of-power/
  3. How do I stay aware of my own “Goliath”-ness so that I never fully become them? This speech was at my college gradution on that exact topic: https://www.youtube.com/watch?v=3oMvVtIQuMk
  4. One of my favorite writers, Chimamanda’s recent post: This is Obscene. I have so many thoughts. Probably could be it’s own post.
  5. Ralph Waldo Emerson’s quote: “Let me never fall into the vulgar mistake of dreaming that I am persecuted whenever I am contradicted.” I love that this beautiful quote was buried in one of his journal entries.
  6. Weary” – Solange
  7. The Other Black Girl – Honestly I recommend the whole book, but this quote from this interview gets to the heart of why the book resonated so deeply with me: “The traits Nella would need to be a good editor – sensitivity to the world, the ability to feel and react deeply – are the opposite of what she needs to successfully navigate publishing to become an editor. I’m interested in the ways your book discusses compromising your authenticity and numbing yourself for survival.” I think this is true of VC too, the traits necessary to be a good VC require sensitivity to the world so you can feel it all and diagnose what is going on and how to plug into it. Yet VC is also a business. How do you square the two?
  8. This whole thread on Twitter…

From CTRL to HeauxTales

I have listened to Jazmine Sullivan’s Tiny Desk Concert more times than I can count. If you haven’t watched it yet, do yourself a favor – it is below, you’re welcome!

I love it. The storytelling and honesty are unparalleled. I was introduced to her new album via her TinyDesk, and when I started digging into the entirety of HeauxTales, I was similarly blown away. She is sharing such vulnerable stories from women – rarely shared – and with so much empathy for the women. Usually I think when these stories are shared, they are accompanied by some level of shame (a number of people have written about this better than I have – this one from Pitchfork was my favorite) and she shared stories in a way that showed the full humanity of each person. So amazing.

I haven’t loved an album this much since SZA’s CTRL. When it came out in 2017, I think I played it every day for weeks – maybe even months?! The main difference that I saw between the two albums is that HeauxTales is a women-only album. There are no men on the tracks. I love the focus that gives to the listener. While CTRL doesn’t have any songs only by men, it does have a number of songs with prominent male rappers featured on them. I distinctly remember reading this one critique of CTRL that the men who were featured took too much control (hehe) over the lyrics and transformed some songs that were supposed to be liberating for women into something else entirely.

Ok, but back to the similarities. The songs that I hear talking to each other on both albums are Girl Like Me & Normal Girl. What I hear from both is this pressure to be who they think the person in their life wants them to be; instead of focusing on becoming their authentic selves. I take it out of the romantic context and see both songs talking about the pressure to conform. I can relate so strongly to this.

The specificity of both of their albums – each focuses on specific stories shared by women – also gives them a weightiness. I am a Revisionist History superfan right now and it reminds me of what Malcolm Gladwell shared in the episode The King of Tears. A reason why country music moves us so much is the specificity of the story told in the lyrics. This is completely different from traditional pop songs that are generalized to mean everything to everyone. He highlights how rap music actually mirrors country music in this way – it’s specific and thus more powerful. He didn’t dig into neo-soul in his podcast (which is the category I put Jazmine and SZA’s album into), but I think if he would have he would have seen a similar trend in neo-soul as he did for rap and country.

Both albums also come at a point of significant transition for me. During CTRL, I was just getting started at Precursor. HeauxTales comes at the tail end of a pandemic where a lot of transition. Very grateful to have this music to guide me during this time.

What album got you through a big transition in your life?

Why I Joined Colorwave’s Advisory Board

I am so excited to announce the I joined Colorwave’s Advisory Board! Colorwave is a two-part solution to accelerate equity and economic freedom in the tech and startup industry for Black, Latinx, and Native Americans. Our fellow program bridges the gap by giving early career professionals of color the training they need and connecting them with leadership opportunities at VC-backed private companies. We are also building partnerships with organizations that are looking to hire this talent into their leadership.

This is a full circle moment for me. In the summer of last year, I tweeted:

https://twitter.com/sydneypaige10/status/1277665275626713088?s=20

I realized through my responses that nobody else had solutions either. I’m so grateful that around this same time, these leaders came together to start building this.

Leandrew – who is an entrepreneur we backed at Precursor – asked me to join right around the same time as Jose Lopez in November of last year and we’ve hit the ground running. In only a few short months, I’ve been so overwhelmed by the fellows themselves. All 22 of the fellows who we are working with in this first cohort are brilliant and any startup would be lucky to have them.

I’ve also been so grateful by the outpouring of support by the ecosystem. From Mandela at Founder Gym who brought her wisdom to bear to build out the curriculum to VC partners like Lerer Hippeau who quickly signed as supporters to invest in this pipeline of black and brown talent to industry experts like Aston Motes who have offered their time and energy to talk with the fellows about what it’s like to be the first and only at a venture-backed startup. It’s been such an honor to work with this team!

Intersectionality in 2020

I had found that the art of simplicity 

Simply means making peace of your complexity 

India Arie, Wings of Forgiveness

As I write this:

If this year has taught us anything, it is our lives are inextricably intertwined. We are called to take actions to protect one other at a level I’ve never personally experienced. What a lesson to learn.

My hope is that this lesson has taught us that intersectionality is not only important when talking about how different women have different levels of access, privilege, etc, but that intersectionality applies to all things.

Real change happens at the intersection. How do we continue to build bridges so that we are walking towards that intersection instead of away from it?

Nothing without intention

Do nothing without intention

Solange, Do Nothing Without Intention

Sydney Paige Thomas