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

The New Fund Manager Survival Guide

How I Built a VC Firm and Track Record at the Same Time

If you would have told me in 2016 when I made the decision to build Precursor, that by 2022 I would have led 15 Deals and that Precursor would have $100M+ in AUM, I honestly wouldn’t have been surprised. I am like that – I take a goal, cloud everything else out, and run towards that goal until I’ve exceeded it.

There are though, many things that surprised me along the way. It was a long journey, one that cost me a lot of blood, sweat and tears and I’m proud of myself for persevering through it all. *queue Beyonce’s Be Alive*

So much of my work in the early days was about building, learning and operating under extreme uncertainty – constantly. When I made the decision to build Precursor, Charles Hudson (who ran point on LP relationships and who was the only other FT person at Precursor) had raised about $5M, and each dollar raised was a struggle. I was also one of very few (but not the only!) Black women in venture.

If I’m honest, the lack of awareness of all of the things I needed to accomplish to reach my goal was a blessing. I don’t know if I would have taken the role if I knew the steep mountain climb ahead of me. I picked a really difficult path.

Essentially, my task was to:

build a Black-owned VC firm (at a time when there are very few)

that was both Pre-Seed + diversified (at a time when both Pre-Seed and diversification was not accepted as a strategy – highly concentrated Seed funds was and continues to be all the rage)

with very little capital (and no trust fund to back me up if I failed)

do it twice as well as anyone else (in an attempt to pre-empt/mitigate the bias that I knew the firm would receive)

all while also launching my own career in investing (something I knew very little about)

To accomplish all of this, I broke the steps down into measurable, daily goals which then compounded into quarterly goals and then eventually voila – there was a website, investments, mark-ups, mark-downs, fundraises, onboarding processes, LP letters, employees, investment memos… the list goes on.

When I was first thinking of this post, the song that came to mind was Seasons of Love (if you haven’t watched Tic Tic Boom yet, what are you doing?!!). How do you measure a year when building a company? I thought I would break it down into Fund cycles because each Fund has felt like its own distinct journey.

Fund I Learnings: 2016-2018

What Have I Gotten Myself Into?

This is the chapter during which I literally had no idea what I was getting myself into. You might remember this blog post of mine during that time: What Does An Associate Actually Do?

I finally got the “dream job” that my nobody – my MBA School classmates and career counselors included – really believed that I could get. I remember many an advice session with folks who made it clear that given my nonprofit background, this aspiration of mine made little sense and shared opinions like “why don’t I try instead to focus on selling toilet paper or razors and if I’m lucky maybe even get a consulting gig?” I did end up selling toilet paper at Kimberly-Clark in Neena, WI for a while, and it was horrible, but I digress.

But now what? What do I do with this new job? With this new really heavy responsibility? I had never seen a VC firm built before, and didn’t have anyone close to me who had much of an experience in VC. I had no idea where to begin. So I started step by step.

Before I get into the steps though, I’d like to paint more of the picture for you about what venture was like in 2016. There were only a handful of firms who had a chokehold on the market and it very much felt like a white boys club. I remember one of the first events I went to – one for LPs to meet emerging GPs. Throughout the entire day, I only remember seeing two women on panels – both of whom were white – and the overall tone of the event felt very didactic. If you built your firm this specific way, you had a chance to pitch to these specific 5-10 LPs, and only if one of them said yes could you be successful. Anyone outside of that norm was highly critiqued. I took it all in and tried really hard to show that I belonged, but to be honest, I felt like I was drinking from a very large water hose and felt like I was always behind – I didn’t know the latest VC Twitter convo or go to the most recent happy hour w/ Elon Musk or have a background in PE/Banking/Stanford to discuss.

I took a breath and started from the beginning. Which I outlined as follows:

  • How do I find awesome companies? I’ll start by finding them with a podcast. I was hypersensitive to the fact that I was a black woman and a newcomer in VC and I wanted to be sure that if I was asking a founder for their time, that I had something to provide in return. I also wanted to use this podcast to prove people wrong. I got so much negative feedback about my thesis in the early days. I knew awesome companies were building in the thesis I created so I used this podcast to demonstrate that. My cousin helped me produce the podcast and I buit it out on free software in the early days of podcasts. It was a challenge, but it’s been awesome to follow-along these companies’ journies because I now have a track record through the podcast as well.

  • How do I find investors I trust? I’ll start by building a network of Women of Color in VC. The idea was sparked by a random lunch discussion with another woman of color in VC. We wanted to create a space for women of color to feel connected to each other. These relationships could result in job offers, deal flow, advice sharing. We planned, scheduled and got sponsors for quarterly dinners for about 2 years.

  • How do I build OS for a VC firm? I’ll start by finding the right tools we need and then, once I’ve figured them out, I’ll publish my findings. It was really hard to find the right tooling in 2016. So much of VC was manual because in a lot of firms, each partner was doing 1-2 deals a year. So they didn’t need software to see a complete collection of holdings year over year. The only real software we were using was Sevanta – which was very old school. Precursor was different. We needed software to account for high volume dealflow and deals. It should also sustain our really large and growing network since we relied so much on coinvestor information as well. So much was trial and error (this continues to be the case honestly) but I was proud to build out our foundational stack which became – Affinity + Airtable.

  • How do I build a deck for LPs? This was pre-Canva and I have no consulting experience which is where all of my MBA friends got their powerpoint skills. I didn’t have the patience to learn powerpoint from scratch and luckily we consulted with Moxie Method who created a powerpoint deck structure with our specific branding, so some of the foundational work was done. Now what do we include? At the beginning, it was such a whiteboard session. Would LPs be interested in founder diversity? Maybe co-investor metrics? How about follow-on timing? In the early days, I workshopped the AGM and LPAC meetings for weeks. I don’t think I can say now for sure that there is a recipe for success here, but we found a template that worked for us and continued to iterate over time.

  • How do I fundraise from LPs? I’ll start by leveraging my previous fundraising experience in the nonprofit space. I realized once I started there, that so many of the same funders I approached at the Fund for Public Schools were also investing in VC as an asset class. As I zoom out, it makes sense – philanthropy was part of the hedge fund/family office/ foundation investment strategy. VC is also a part of their investment strategy. I don’t know for sure, but I wouldn’t be surprised if the same overall percentage of capital is given to philanthropy as well as VC. Because VC is such a high risk strategy, the investment dollars might return $0, which is the same return as philanthropy.

  • How do I value companies? I had only taken the online version of Venture Deals before – which talks about how to value companies in a theoretical manner, but this did not prepare me for how to value real life companies with real life founders building our real life future. I had so many questions – and continue to have these questions – because I don’t think that valuing companies is a science, it is more of an art and it is an art that holds a lot of bias. The below tweet is from very recently, but the underlying premise holds true throughout the ages.
  • How do I build cap tables? I’ll start with google. While I had taken one financial modeling class in business school, it really only gave me the basic tools to build out an excel spreadsheet. The free tools I found on google were worth their weight in gold as I learned how to read and design cap tables. Some of my favorites were Captable.io (now LTSE), Funders Club and Corporate Finance Institute.

  • How do I build a website? I had never built a website from scratch before. But I had built out some templatized pieces of a website before (thank you, Fund for Public Schools for that opportunity!) I learned via trial and error how to upload photos on our website which was particularly challenging – we were attempting to showcase the faces of our founders to demonstrate that we backed different people compared to others. To help out with the pieces of the website that I simply couldn’t figure out, we employed a contractor – Kenneth Lim – who was immensely helpful.

  • How do I build a scalable support network for founders? So much of the support we would need to provide founders would need to be scaled. The vision early on was not how do we support 1 founder or 2 founders, but how to support 15, 20, 100. We have now grown to over 500 founders. In 2016, believe it or not – Slack was not a big deal! It was not widely used and was still very much a startup. We created a founder Slack early on with the hopes and dreams that it would become a self service like product. What we found was that because the founders we were working with were Pre-Seed, they had a lot of operational, administrative questions that could easily be answered in a place like Slack – like what PEO are you using? or, how are you paying your intl employees? or, does anyone have extra office space in FiDi? All we needed to do, in many cases, was get founders together. So in the early days, it was a lot of dinners and lunches.

  • How do I write investment memos? In the early days, we did invesment memos for all of our rounds done via an SPV. I mirrored my investment memos based off of the public policy memos that I used to do at Duke University (who knew that Public Policy degree would be helpful in finance!). I am so grateful for that training. It allowed me to structure memos as a 1-pager, why did we invest initially? what has been their progress since the initial investment? why do we want to double down on this investment?

  • How do I read, review and issue term sheets? One of my first projects at Precursor was to analyze our terms sheets across the portfolio and put together a spreadsheet so we could catalogue with whom do we have side letters. I spent a lot of time reading and reviewing term sheets over and over – in those days priced rounds were the norm even at Pre-Seed/Seed – and understanding the nuances between what a Cooley term sheet looked like from a Fenwick term sheet and everything in between. There wasn’t much I could find on google that helped me here and instead, so instead, I took my skills from working with a lawyer in NYC and read each document closely and intently, over and over again.

  • What is crypto? One of the first things I got excited about when I joined Precursor was crypto. I spent months digging into it. I was obsessed with the idea that blockchain could really help the government operate more effectively. You wouldn’t need to sign 10 different piece of paperwork if all of your information was stored on the blockchain. I got really far down the rabbit hole learning about ideas that were getting implemented in Dubai! This was my first experiment on getting up to speed quickly on an area I previously knew nothing about and it was envigorating.

  • How do VC finances work? I was in charge of managing our first audit and also the fund’s budget. It was a lot to manage on top of all of the other things, but was great to get a very clear-eyed understanding to exactly what it costs to set up and manage a VC firm.

  • How do I take care of myself emotionally and financially? So much of the early days was really hard. I spent a lot of my time doing my own work and in addition to that supporting Charles as he was on the front lines of fundraising and had to shoulder a lot of the financial burden of starting Precursor. I shouldered my fair share as well – taking a lower salary, working extremely long hours and not having much of any of the traditional support system you receive in corporate life – whether that was the HR benefits or the peer colleagues. I found that so much of that early work was instrumental in giving me a clear eyed view into what it means to be a founder and I rely a lot on that experience to help me as I counsel founders today.

Fund II Learnings: 2018-2020

Focus on The Founders

As I began to find my footing, I started to think through where I really wanted to spend my time in venture. I had always had a clear vision about the types of founders I wanted to back and the types of companies I wanted to champion. Now how do I start working towards that more focused goal?

  • How do I deepen my relationship with investors? I decided to join the NextGen VC Board to help me develop a stronger network with investors. I applied with the help of Anarghya @ Maveron and interviewed with Sunil @ Ubiquity and Roseanne @ Renegade. I got the opportunity to explore how to cultivate events and experiences that would allow me to build a community who I could rely on throughout my venture career. Over the course of my Board tenure, I planned many a wine bus trip and happy hour and it was a lot of fun!

  • How do I communicate my values? In my previous career, I never had to worry about this as much. In the public sector, you know that everyone who is there has a principle value of service. Now I was in VC where a lot of people valued wealth over all things and I didn’t know how to relate to these people. I decided to create a user guide to help me navigate these new waters.

  • How do I get into the flow of information? I was given an opportunity early on to join calls that Charles was a part of. I would send him an e-mail at the end of each week, letting him know which calls I’d like the join in the following week and he would let me know which ones I could join. I was so swamped in the first two years that I didn’t take advantage of this much. In Fund II though, I was oftentimes in back to back meetings with Charles all day for days at a time. Listening to the questions he asked founders/LPs/other investors, listening to the concerns founders/LPs/other investors had and trying to soak up as much as I possibly could. I also created our IC meeting during this time to create some structure as well.

  • How do I get leverage? As I transitioned into a new role, I had to figure out how to make sure all of the previous things I was doing before got done. We were still barely $50M AUM which meant very limited management fees, so I was cost conscious when I thought through how to get leverage. I reviewed most of the tasks I was doing before to explore which I could automate (Zapier became my best friend!) and which I needed another human to do. There was more than enough work for another full-time person and because we didn’t have a hiring manager, that meant I had to learn how to become the hiring manager. I drafted the job description, posted the role across LinkedIn, Twitter and elsewhere and singlehandedly reviewed over 300 applicants – taking phone interviews with about 100. I tried as best as I could to limit bias in the process and we ended up hiring an amazing person for the role – Ayanna Kerrison – who is still with us today.

  • How do I create a more inclusive ecosystem? Something that I recognized early on was that the many of the types of companies I wanted to invest in were led by Black and LatinX founders. However, my experience was that there was a perceived increase risk of those founders – honestly for no good reason. But the perceived increase risk of those founders led investors to increase their diligence of these founders and worry significantly about the ability to syndicate those deals. So in order to generate more awareness of who was already doing these investments, I decided to create a list of investors doing this work. It was very challenging work for me. Because there was no public information on this, I had to poll investors I knew one-by-one on how many investments they had made into companies founded by Black or LatinX people. I polled 100s of investors and with that data created The Interrupters List to shine a light on those who were doing this work to inspire others to follow their lead.

  • How do I move from reactionary to strategic? As processes were nailed down and things felt like normal, I wanted the firm to move into a more strategic place. I built out our quarterly offsites to make space to talk about things impacting the firm more generally and how we could get ahead of the next thing. The first quarterly offsites were very open-ended where I tried to bucket our conversations into categories and discuss topics pertaining to those categories.

  • How do I continue to build a name for myself so the right founders can find me? I spent a lot of time trying to figure out how to make sure founders could find me. I continued working on my podcast, spoke at SXSW, spoke at Grace Hopper, participated in interviews and traveled to Australia! The hard work paid off. I sourced about 200 companies the first year, and over 600 the second year!

  • How do I do my job well and also be thoughtful about my own boundaries? I’ll be honest, I am still working through this in therapy. I don’t know if you saw Encanto, but my life growing up was a combo of both Mirabel and Luisa – so I am very used to over-giving. When you are in between two roles as I was – helping Ayanna get up to speed and helping Charles work with founders/LPs – it is hard to figure out where my role started and where my role ended. I was pulled in a lot of directions and was still figuring out my voice in this ecosystem and learning how to say no.

  • How do I manage my own anxiety as I manage the uncertainty of this new role and the uncertainty of Precursor? At this point, Precursor still felt very much like a startup. In addition to that, because I was so great at my previous role, I was promoted into a role I didn’t know if I was good at! I joined Pathwise to help provide me with a trusted community so that I could be more thoughtful about how I was showing up in spaces around me. It was such a great group of people to learn from and I got the opportunity to practice showing up as my authentic self in this industry which was really useful and helped me build my own confidence.

  • How do I start prioritizing myself again? I spent so many hours in the early days on all things Precursor. Days, nights and weekends were booked, and I rarely if ever took a vacation that lasted more then 2-3 days. I realized this was unsustainable and had a hard conversation with Charles. I also realized in this time, that in so many of my previous roles before Precursor, I burned out after two years and then found a new role at a different company, where I would rinse and repeat. I didn’t want that to happen here and wanted to address it in advance. I decided to take more time off, spend time exploring other projects that gave me joy and also got more deeply involved in my community.

Fund III Learnings: 2020-2022

Building my Track Record

I picked a really hard asset class to build a track record when so much of how this industry defines success for track records is: did the company raise lots of money from <enter cool multi-stage firm’s name here>. Deciding to invest in pre-seed companies, which predominately have the highest risk of all, means I’m asking for a lot of heartburn. Especially compared to folks who have instead decided to focus on Seed/Series A deals where there is more data and more infrastructure to a company that you can evaluate. In addition, lots of the pre-seed companies I invest in are pre-product, which means that it can take them the full 18-24 months to get to a strong Seed round and years after that to get to a strong Series A. So how do I do this, in an industry that is fueled by so much hype, growth at all costs stories, and generally keeps a short memory?

  • How do I define success for myself? First things first, I needed to build a strong internal compass. This feeling of groundedness would keep me from flying too far into the wind anytime a challenge arose, and could also help me stay laser focused on what really mattered. To me, success is building multi-billion dollar businesses alongside founders who care deeply about the people they are building their product for, and through their work are committed to making life better for the 99%. There are millions of ways to accomplish this and I can’t get distracted about other metrics of success, until the end goal is achieved.

  • How do I invest in a pandemic? Being able to begin my checkwriting career in a pandemic was both a blessing and a curse. A blessing because I got to see more companies than ever before because so much work was done on zoom. I saw about 2K companies over the course of this time! A curse because the founders I was backing were still largely first time founders, so guiding them on how to build a company in a global pandemic was challenging to say the least.

  • How do I transition from asking for sponsorship for my decisions to becoming a decision maker? This one was so hard! I have never had a leadership role in my work like this before. In my 10+ year history of working, I have never been the boss. So when I had to transition into this leadership role, I had to shed a lot of the “asking for permission” behavior that I had learned that had gotten me to this point. I had to learn to trust my own judgement and to stand strong in my own opinion even when faced with opposition.

  • How do I invest in our team? We grew a lot during the pandemic. I found us a great CFO and also supported a new analyst search. Charles hired a Chief of Staff as well. We were no longer a team of 2 or 3. There is something about becoming a team of almost 10 that really makes you think about company building. I launched a series of conversations around – how we wanted to work going forward, what additional benefits we’d like to see, and how we could start incorporating more effective communication strategies like getting trained on how to provide feedback and building out more effective meetings. I am grateful for The Grand (full disclosure: they are a Precursor portfolio company) for their wisdom here and I also listened to a lot of Brene Brown’s Dare To Lead Podcast at that time to inspire and inform new stragies.

  • How do I continue to uplevel? As I grew into this role, I felt more and more overwhelmed. I joined Kauffman fellows which helped me identify more insights about myself. I realized that in order for me to uplevel, I needed a crew. A group of people who I could be completely honest and vulnerable with who I knew would have my back. My forum in Kauffman has become that and I’m grateful for all of the other programming Kauffman has provided as well.

  • What do I need to do my best work? Now that I have more reponsibility on my plate, what do I need to be successful? This answer is still evolving, but I realized the big thing I needed was space. Space to think, space to give me time to respond vs react, space to write, space to continue honing my own voice and trusting my own decisions. I started working with a FT EA, made the decision to work from home for the forseeable future, made the decision to get a coach (thank you, Jen for helping me find her!) and doubled down on learning how to say no. I also now try very hard to make sure I have spaciousness built into my calendar like No Meeting Mondays and budgeting time for daily breaks.

  • How do I guide founders on my own? As I made the move to invest in companies myself, this meant that I was the deal lead for all things related to that portfolio company. I generally spend about 1hr a month with each founder and also make myself available for adhoc concerns. If the company needed guidance on fundraising, they called me. If the company needed leads for a new hire, they e-mailed me. If the company had product ideas they wanted to explore, they told me. I was now the main point of contact for each founder I worked with and I wanted to be able to show up for them in a way that was authentic to me. I built out a one-pager on all of the things I wanted to be able to offer, and focused a lot on how I wanted to be seen as their coach – I decided to invest in their companies to guide them on their growth, not to fix them.

  • How do I build a thesis more publicly? After a year of investing, I decided to launch a Precursor substack with my own writing about my thesis. I used a lot of the learnings I gained from working with founders to fuel a hopeful and honest view on why I was excited about backing companies building for the long-tail. It took me about two months to build out this thesis and I’m so grateful for many of the founders in the portfolio who helped me draft and edit it!

  • How do I build networks within this thesis? I decided to build the SMB Syndicate with a few friends after I was told many times that SMB tech was too small of a market. I knew this wasn’t true and so I decided to collaborate with like minded individuals to showcase the great work going on in SMB tech. SMB tech fits squarely into my thesis so I also wanted to build this group as an excuse to share deals and collaborate on deals with others investing in the same space.

  • How do I let go of the sef-limiting beliefs holding me back? I talk to my mentor, Miriam Rivera, about this all the time. As the saying goes: what got you here, isn’t going to get you to the next chapter. So much of what propelled me to this place was my own fear and anxiety that I wasn’t doing enough. I needed to do more and more and more to catch up! Now though, I’m setting the pace. The new work that I do now requires attention, strategic thinking and concetration. That means focus. Which means I can’t be trying to do everything anymore. Another belief that I’m working on shedding is this belief that in order for anything to be worth it, it must be a struggle to achieve. I’m allowing more ease into my life which is a daily practice.

  • How do I want to show up in the world? I am still figuring this out, but I know that so much of how I show up in my the world must be grounded in both my own sense of self, sense of community and sense of justice. I wrote some thoughts on how I am grappling with my newfound power, and I hope to use this power for good by also spreading it among organizations like Colorwave and Project Include.

Light work*

Through this essay, I hope that I have illuminated some of the many pieces of my story and through that illumination, I hope that it helps light the path for others as they find their way and build towards their own vision.

*conclusion inspo: Yrsa’s Substack Article titled Light work

How I Got More Involved in My Local Community and Government

Growing up, community work was always on my schedule. Whether that was volunteering as a liturgist at my church, delivering meals via meals on wheels, running behind my mom as she raised money so other kids in San Diego could get scholarships to college, I was always involved in my community. As I grew up, to address this part of my identity I conflated my work and my community service. Working in the government and nonprofit sectors made this easy to do. It wasn’t so easy when I transitioned into the private sector in 2014. I didn’t make time for this again if I’m honest until 2016 when he-who-shall-not-be-named was elected President.

I remember a rush of interest from friends and colleagues on how to impact national elections. Writing letters to Senators, signing petitions, and wearing pussy hats became normalized. It felt like I had regained some sense of community activism in my life too. This collective work felt good despite the fact that I (like many people) was put on an emotional rollercoaster. Part of the emotional rollercoaster was dedicating so much of my community service work to national causes. I didn’t realize how much this would have on my mental health, but the lack of agency that I had and the inability to see my impact on a real level made it all more exhausting.

It was around this time that I began to explore how I could become more involved in my own local government. The problems facing the entire country – 300 million people!! – are so big, so broad and so thorny that I thought maybe I could see the needle move on my efforts if I decreased the scope of the problems was looking to have an impact on. I am from San Diego, CA – a city that boasts a population of almost 1.5M, yet most of the work I did there was focused on a very small community surrounding the church I was raised in and the nonprofits my parents got us involved in from an early age. Oakland is barely 450K people so I thought to myself, of course, I could make a dent here on a community in The Town if I really tried. This effort reminded me of the bell hooks quote in All About Love where she says: “I like living in small towns precisely because they are most often the places in our nation where basic principles underlying a love ethic exist and are the standards by which most people try to live their lives. In small towns where I live (now only some of the time) there is a spirit of neighborliness – of fellowship, care, and respect.”1

I started off by joining a nonprofit board in Oakland. I found the application online! It was an interesting experience where I was able to work with Beyond Emancipation – a nonprofit committed to helping foster youth build essential skills. The impact I was able to have was amazing, but the workload was too much. After a bit of reflection, I realized that part of the reason the workload was too much is that I took on too much instead of delegating. But I needed to quit to get that perspective and I’m proud of all of the progress they’ve continued to make.

After the pandemic started I began to reconsider my relationship to public policy once more. I started by talking with neighbors about ideas to build out a mutual aid program for those in need and at the same time, I began joining in on Oakland city council meetings to listen and learn more about what our public officials did. I also spoke up during public comments to vocalize my opinions about police brutality in Oakland.

Both of these efforts led to some really awesome results. The first was that the mutual aid program gained steam and a small group of 4 helped fundraise over $10K for neighbors in need. Our giving drive even gained us a spot on local television! I am so proud of the work we were able to do. The checks we sent out allowed people to pay rent, buy groceries, pay past-due bills. It was amazing.

After joining a few City Council meetings, a friend shared that Oakland actually had a variety of public commissions and boards that allow you to get deeper engagement into city policies. The applications were online and so I applied to the Oakland Public Safety and Services Oversight Commission.

I honestly had no idea what I was getting myself into and I’m grateful I didn’t (this is the story of my life honestly: pick a goal to achieve first, get overwhelmed by all of it figure out the details later). I was signing up for 2-years of public service which included, but wasn’t limited to, 1 meeting per month that lasted anywhere between 2-4 hours – this meeting was usually held on Mondays at 6:30pm, which meant that I was sometimes in meetings during a workday until 10pm at night. In advance of the meeting, you are sent pages and pages of documents to review. In order to come prepared to have a productive conversation, you needed to read these documents. The Oversight Commission I was on was tasked with reviewing $30M+ in spending a year – that is a really big deal! To honor that, I wanted to do my job well.

What I learned quickly after a few meetings, was that because the turnover of the Commission was so high, many meetings could feel like we were starting from scratch. You don’t realize how meeting only 1x per month can impact your ability to be fully prepared and present until you find yourself asking the same question across multiple months. It was at this time that I decided to build out a presentation that could tell the story and impact of the Measure our oversight commission was created to oversee – Measure Z – over its entire history. I joined the Oversight Commission almost 7 years into its implementation and so had a lot of data to work with.

A few other Commissioners and I spent 6+ months pouring over the 7 years of data to compile this presentation. We gave this presentation to the City Council in December. Looking forward to seeing how this progresses!

  1. All About Love – bell hooks. Page 100.

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!

Why Being a Capitol Hill Intern is the Perfect Pre-VC Job

My first office job was as an intern on Capitol Hill. (My first job was selling Cutco knives to my neighbors, but that’s another story!)

I can’t imagine a better training ground for my work in VC. Why?

  1. As a Hill intern you have to respond to every constituent email. That means sometimes 100s of e-mails a day. Yes you can build out a template, but each one needs to feel personalized. People are e-mailing you about very personal and important topics – climate change, healthcare reform, their own experience with discrimination, the list goes on. As a VC, I am now responding to 100s of e-mails a day and doing the same thing. I am creating some templates to help me shortcut the timing required to get back to every single person, but I’m also personalizing every e-mail so that the folks who reach out know it’s a person who is responding back. They’re e-mailing me asking for funding to support a company they might have put their life savings into – they deserve a response that has some care given to it.
  2. As a Hill intern, you have to manage many stakeholders all the time. When I was interning for Congresswoman Barbara Lee, the Republicans had just taken control of the House. That meant that Congresswoman Barbara Lee had to manage these new colleagues of hers, and also the expectations of her very liberal constituents who elected her. Plus she had just taken the role as Chairwoman of the Congressional Black Caucus (CBC). This does not include the other leadership positions she had at that time – so she had to manage the relationships with the CBC on top of the other positions she held in the House. She was pulled into a hundred different directions daily. She was an amazing role model for me to watch. As a VC, it’s very similar. You have the expectations of your investors (or LPs), your co-investors, your portfolio, your teammates… Managing all of these stakeholders while also staying true to who you are and what you came into office (or into VC) to do is hard and also one of the most important responsibilities of the job.
  3. As a Hill intern, you have to play the long game. There are no metrics for success. You spend most of your day writing e-mails, drafting PR statements (I got to help draft the one Congresswoman Barbara Lee wrote after Michael Jackson died), and just generally helping. The path towards working on policy and legislation often times requires first working on consituent related problems. Congresswoman Barbara Lee is a great example – she worked for Ron Dellums for years before exploring a Congressional seat. You are required to do work that serves others before you become a decision maker. This concept of servant leadership teaches you how to stay focused on the collective instead of yourself. Which is honestly a great pre-requesite for any leadership position, but I think it has definitely served me well in VC!

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

Why I Decided to Do Kauffman + How I Found the $$$ to Pay for it

I am so excited to be a part of the Kauffman Fellows Program! I did it for a variety of reasons, which I’ll try to outline here.

First, though, I want to tell you about my biggest pandemic learnings. The answer to why Kauffman starts there.

Pandemic Learnings

The pandemic gave me a lot of time and space to reflect on how I was previously operating in the world and explore how I might design a life that fits me post-pandemic. I realized that I was very reactive, almost constantly, in pre-pandemic life and I wanted to build more intention into my life. After this reflection, I started to explore what I used to do in pre-pandemic life that doesn’t suit me.

The first thing I came up with was networking. I realized I get very serious anxiety around networking in its traditional sense. Attending events, especially nighttime events, was devastating to my sleep. It takes me hours to process events because I am very hypervigilant in large groups, which means that the cost of a nighttime event is a nighttime of sleep.

The second thing that came up was my commute/working life in SF. I am based in Oakland. I love Oakland so much!! I love the new friends and communities I have been able to build because of the pandemic-induced WFH situation. I am now more deeply connected to my neighbors, local businesses + city government. I won’t give that up. My ability to live in a neighborhood whose values align so deeply with my own, to have Black neighbors, to have the kids on the street look out for me to see if I’m hanging out on my porch swing… it’s really beautiful. I now know the true opportunity cost of my commute/working life in SF. While Precursor plans to open an office eventually, I don’t expect to be there for more than a few hours on 1-2 days a week and plan to use that time specifically for team building.

There are a few reasons why I think it took me so long to realize these qualities about myself. One of them is that there is a prevailing notion in VC that younger VCs have infinite time and energy because they don’t have children, spouses, etc. This is compared to older VCs who have families and can’t possibly be expected to go to another networking dinner. I fundamentally disagree with that. Young VCs might be caring for aging parents, might be volunteering in their community, might be struggling mentally/emotionally and this expectation that their time is less valuable than older VCs’ time is dangerous.

As a result of this reflection, I decided to replace the very transactional nature of many of these coffees and lunches and happy hours with anyone who e-mails me w/ an @vcfirm.com e-mail address with an experience that gives me an opportunity to build relationships with people who are taking the time and effort to really get to know me and who are excited about improving themselves. Which brings me to Kauffman. I am so excited to join this group of folks who are building intentional relationships with each other in a way that is less transactional.

Growth Mindset

Another reason I joined Kauffman, is because while I have a really strong perspective on what types of companies I am passionate about investing in, I know that there are still things I don’t know about this business and myself. I am looking forward to using this space, as a Kauffman Fellow, to be, in many ways, a learner. There is a lot of talk about how Black women need the same opportunity to fail as white guys. I think what we also need to explore is the concept that Black women need the same opportunity to be seen as learners instead of as experts. There is so much research that shows that Black girls in education spaces are adultified. While I’m no longer a child, I think the corollary here is that as a Black woman, I’m often expected to enter new spaces and know all the things all the time – to never slip up. This is a trap. I deserve the space to be seen as a learner and to be given the grace that learners are given. I am grateful to be at a fund that gives me space to learn, make mistakes and grow within the fund. I wish that for all Black women in VC.

The Cost, Though

I want to be honest about how I paid for it. I am not rich, plus Precursor is not a $1B+ fund, so I had some really hard decisions to make.

$80,000 is the cost of Kauffman. Let’s not beat around the bush here: that price tag is really really steep. This leads to an exclusion of folks who might find the experience useful, but just can’t figure out how to make the numbers add up. Many Black people in venture are at less established funds that are unable to foot this large bill on their behalf and they don’t have access to the family wealth to put down this capital on their own. I know this to be true, not just because of the data, but because that is my story. To me, that $80K might as well be $1M. I don’t have $80K and have no way of borrowing it from family. So after I applied and got accepted, I asked for help. I reached out to people and organizations who have been supportive of me over the last 5 years and I was met with such generosity. I was able to get $10K from an 😇, $20K from a sponsor organization and $40K from Kauffman. Precursor paid the remaining $10K.

I am so lucky. I know that. I am brainstorming ways to make this experience more accessible to those who are not as lucky. More updates on that later this year! If you’re interested in collaborating on this and have ideas, let me know! You can reach me at sydney@precursorvc.com.

Thanks for reading! Looking forward to continuing to share more about my experience in the program over the coming months and years!

References and motivation to write this:

  1. Nick Caldwell’s “Happy to Be Here” YouTube clip

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…
Sydney Paige Thomas