2 Years After My Real People Thesis

In 2017, I wrote out a “thesis” (I know, very VC of me).

In it, I wanted to record to both the world and to myself, a promise that I was going to focus on founders building companies that give real people more agency over their lives.

Since I wrote that thesis, I’ve: completed 2 seasons of my podcast, had 1000s of discussions of entrepreneurs, made 394+ new investor “friends”, and supported 120+ companies in the Precursor portfolio. I’ve had all of my systems on overdrive to manage this growth both personally and professionally so thought it was time for some reflection.


Update #1: The underlying premise of my focus on “real people” still holds true to me.

This is unsurprising as I’ve spent the last 10 years of my career on this same beat. Whether it was advocating for low-income tax filers to the federal government or building a better CSR practice at a mid-stage company, I’ve always been interested in how to create systems that make this economic project of capitalism work better for everyone.

This is where I get the most energy, am most compassionate and think most creatively. In the words of Frida Kahlo:

Like Frida, I can get pretty insufferable — to others and myself — if I spend too much time thinking about things that are generally in vogue with cultivated people. Generally, I categorize these things in the following camps:

  1. Lofty ideas that have no likelihood of implementation — ie any conversation had at burning man
  2. Mediocre ideas that can squeeze more out of the “maker class” to make the “thinker class” richer

Update # 2: BUT, my thesis is too broad.

If I would have taken a look at the few companies I was really excited about  I would have seen the trend clearly, but alas here we are. Better late than never. Both of the companies are focused not just on helping real people access more agency, but on fundamentally altering economic systems. Essentially, this is a version of the old adage:

Give Someone a Fish, and You Feed Them for a Day. Teach Someone To Fish, and You Feed Them for a Lifetime

How do these companies address economic systems change?

  1. Red Bay Coffee: They source coffee directly from the communities making it via direct trade. Their company is also a co-op where employees have ownership.
  2. Lacquerbar: They are focused on giving nail technicians — a group of workers who have been historically treated very unfairly — access to premier education that will help them access new opportunities within their industry. This access also unlocks a new more equitable way of building and operating nail salons.

My focus is here because my interest is here. I’m interested in solutions that fundamentally alter our economic system for the better. The incremental bores and frustrates me. Thinking in big picture gives me hope.

An additional piece to this is if you’re building an economic systems change, you have to be targeting the long-tail, a harder to reach population that has been negatively impacted by this system. I think this is a competitive advantage and a huge moat because aggregating this long tail is so difficult that others can’t figure it out and won’t be able to copy you.

I have, I think, a good eye for how this can be done in asset-heavy businesses; however, I think that this can be done in asset-light businesses as well.

I am on the hunt to find them so that we, at Precursor Ventures, can invest! If you are building one of these companies, please reach out.

Update #3: I’m realizing that my interests are different than most VCs which makes it even harder.

I’m trying to support the creation of something that is fundamentally different and untapped. This means that there are few current proxies for their success. When I was feeling down about this, it was really helpful to read this from Paul Graham at YC.

…the average investor is, as I mentioned, a pretty bad judge of startups. It’s harder to judge startups than most other things, because great startup ideas tend to seem wrong. A good startup idea has to be not just good but novel. And to be both good and novel, an idea probably has to seem bad to most people, or someone would already be doing it and it wouldn’t be novel. That makes judging startups harder than most other things one judges. You have to be an intellectual contrarian to be a good startup investor. That’s a problem for VCs, most of whom are not particularly imaginative. — Paul Graham

One thing I didn’t realize though was how difficult it would be to divert capital from a widely acceptable “good” investment to a very polarizing “amazing/terrible” investment.

This is ironic because I think it is this polarizing nature of companies that can become the bedrock of its success. Revolutionary ideas are hated by some and loved by others. That’s how some of the greats were made.

Google revolutionized access to information.

Apple revolutionized access to computers.

Square revolutionized access to banking.

Amazon revolutionized access to commerce.

Shopify revolutionized access to building online stores.

I’m looking to do something on the same scale and think that for it to be done, it can’t be left up to broad consensus.

So that’s where I am now… if this feels incomplete, it is because it is. Still working through this and looking forward to reporting back on more findings in the coming years 🤓

My User Guide

How I approach my work within venture capital

Ah‚ you’re part of something way bigger
Bigger than you‚ bigger than we
Bigger than the picture they framed us to see
But now we see it
And it ain’t no secret‚ no

— Beyoncé Knowles-Carter, “BIGGER”, The Gift Album

I recently realized that when I enter conversations with other VCs, I have a pretty complex background song playing. It’s not always Bigger by Beyoncé, but it usually has a similar tune. 🎶

To help people understand how to work with me and get the beat down of the song playing in my head, I decided to create a user guide. A “user guide” (or manifesto or first principles) is a list of your own values.

I decided to create a User Guide when I realized that I’m pretty complicated & putting my values down where everyone could reference them could be a useful resource to decrease stress & anxiety of interactions

Here is my first stab. I hope you’ll treat it as a living document that reflects the living, evolving person I am.

Let’s begin with a quick summation of my life story:

I grew up in San Diego, CA

I spent summers in West Virginia with my mom’s side of the family — that includes, but is not limited to 11 uncles, 1 aunt and 20+ cousins

I graduated from Duke University with a major in public policy, just 4 years after the lacrosse scandal

I drafted legislation for the City of New York + lobbied the federal government to pass it

I conducted tax preparation services for low-income New Yorkers, supported a multi-city roll-out of a city program & raised money from private sector organizations like Nike to invest in New York City’s public schools

Then my background starts to get boring…

I went to business school at Berkeley-Haas

Then it gets exciting again!

After business school, I helped Charles Hudson manage and operate Precursor VC

Cool cool cool, if you have read this far, thanks for getting up to speed – we are now the same page.

So let’s get into the question I really came here to answer: “what is my relationship to venture capital”.

Short answer: It’s complicated 🤷🏾‍♀️

Long answer:

1. Venture Capital has a transformational ability to support and finance companies that are building scalable solutions for people and places that have been systematically under-invested in. That excites me more than anything which is why I’m here. 🎉

More background on my POV: Why I’m Betting on Real People

2. At the same time, the relationship between capitalism and black people in the US has been fraught since slavery.

a. Black people were brought to the US to build foundational pieces of the economy (agriculture, railroads, construction) while venture capitalists’ invested in them and reaped the rewards.

References: Without Slavery, Would The U.S. Be The Leading Economic Power?

b. After emancipation + reconstruction, many black people had the capital that they accumulated stripped away from them leaving us with today’s issues of extreme wealth inequality between races.

References: 8 Successful and Aspiring Black Communities Destroyed by White Neighbors

References: African American Homeownership Falls to 50-year Low

c. There has been little action taken to decrease this inequality and instead, immense work has been done to reinforce a brand of meritocracy. As a result, the word “meritocracy” and the assumption that folks with power deserve it or earned it hurts me.

References: The Perils of Meritocracy

3. This informs my own imposter syndrome as a black woman in VC — I know that 1M+ black or brown people could be great at this job and yet somehow because of my own luck, I have ended up here. So I take great care to try and call in those left outside of the room & make their voices heard.

a. My imposter syndrome has nothing to do with a lack of pride and confidence in my own work. I work very hard. I produce high-quality work. I am really proud of it. I am very quick to anger when I am around people who don’t have high integrity around their own work product.

b. You can read more thoughts on my ideas of imposter syndrome here.

4. I struggle with the evangelization of technology and startups. Startups/tech/entrepreneurship is hard, but it is not the hardest job. Having family across the country with many different socioeconomic status’ keeps me grounded. A harder job to me is trying to making ends meet while working for less than minimum wage in the only job available to me in the small town where I live. I’m not in venture capital because it’s the hardest work available, I’m doing it because it has the widest impact.

5. We are all complicit in an economic system that has caused significant trauma on people, communities and countries across the world.

My favorite book that discusses this is American Spy — review by NPR here: ‘American Spy’ Is A Unique Spin On The Cold War Thriller

6. In order to be a productive member of society, being a thoughtful investor is not enough. The work starts with you. The arc of the universe does not bend towards justice if nobody does the work to make it so. How are you building a pattern of reflection and growth? How are you living your values? Do you wonder how what you say/do impacts others? What are you hoping to accomplish in this lifetime? How are you actively working to raise your own consciousness so you don’t become a reactive pawn in a greater system created by other people? These are questions I struggle with daily. One of the ways I work towards addressing them is by building a full life outside of my day job. I am an active supporter of Beyond Emancipation, the North Carolina Bail Fund, Esq Apprentice and am getting more and more involved in my own community of Longfellow, Oakland.

a. One of the best places to start is with your own language. How are you talking about people who are different than you? I was just introduced to this quote by Toni Morrison that says: “Oppressive language does more than represent violence; it is violence.” It is so true.

b. Another great place to start is with your own community. What are you doing to support people in your community who have different backgrounds than you? Do you volunteer? Do you donate? Do you support taxation that goes to critical infrastructure that you and others need?

7. I think that listening to people different from you, and changing your opinion accordingly, is the biggest act of courage you can take. This is based on my love for humility. It is my favorite trait (right above gratitude) and one I try to practice often. Humility isn’t a widely appreciated trait in VC because it is at odds with industry standards of conviction, assertiveness and self-righteousness which makes this work hard sometimes.

a. One of my other favorite traits is kindness. I just don’t know why people chose to be mean. I just don’t have it in me and it makes me sad when people chose meanness over kindness and compassion.

b. My third favorite trait is thoughtfulness. I am not one to make decisions in the moment. I need time to think and reflect before making decisions.

8. The hustle culture of entrepreneurship and tech is problematic. It is particularly problematic for communities of color where the old adage that “you must work twice as hard to get half as much” rings true. That isn’t a life I wish to cultivate or to exhault. It leads to burnout and breeds exhaustion which can create even more anger amongst underrepresented communities. I recognize the privilege in this lifestyle choice and also believe that my ancestors wouldn’t want me to live in a way that hurts me if I don’t have to. I approach my life and my work within VC with this lense and work hard to build boundaries so that I can have a full work and home life. Please don’t try to e-mail me on weekends and please please please don’t follow me on instagram 🙃

a. That being said, one of the values that I hold deeply is that in order to be successful, you must be proactive. If you are reaching out to me cold and would like to speak with me, I expect that you have your questions prepared. If I have invested in your company, I expect that you will treat me as a valuable resource who can help guide you. One of the most frustrating experiences I have had, and would like to prevent, is feeling like the person I’m talking to isn’t taking full advantage of my time and and/or isn’t taking responsibility to make their situation better. One of the quotes I try to live by is: we all have agency over our own lives and I have continually developed a practice of proactiveness. In order to work together effectively, I need to see you model proactiveness as well. I try really hard and work best with people who are also trying really hard.

References: Black Workers Really Do Need to Be Twice as Good

10. Being a black woman doesn’t mean I have all the answers to inequality within this industry or outside of it. Please read a book (or an article) before asking me any questions pertaining to inequality, white supremacy, racism, etc.

References: How To Be A Better Ally: An Open Letter To White Folks

a. I am still very much a beginner in learning about the different struggles that other communities of color experience. And welcome more resources that I can use to improve.

Some of my favorite books have been:

In the Midst of Winter —From Isabel Allende, a Novel of Three Immigrants and a Brooklyn Misadventure

Pachinko —Culture Clash, Survival And Hope In ‘Pachinko’

Exit West —Escaping A World On Fire In ‘Exit West’

Long Story, Short: I love venture capital and technology, but my relationship to it is complicated. This industry was not created in 1976 with the invention of Apple. Books are important, history is important and without those two things you can become an actor in a greater narrative that you didn’t know existed — I try my hardest not to be that actor, but mess up sometimes. When I could do better, I expect you to call me out and I promise to listen. To earn my respect, I expect you to try hard too. I also expect you to mess up sometimes — at which point, I will call you out on it and expect for you to listen. We’re all human.

First Draft Written: August 9, 2019

Updated: March 11, 2020

Updated: March 12, 2020

Updated: January 13, 2021

Updated: January 27, 2021

Updated: January 28, 2021

Updated: January 29, 2021

Updated: April 23, 2021

Grace Hopper, Female Founders & Structural Inequality

#GHC18
I recently got the opportunity to speak at THE Grace Hopper Conference 🎉. It was my first time attending and I didn’t quite know what I was in for.

I was blown away by the brilliant women I met there and the investment poured into the 3-day affair to make sure that they were supported. Parties, panels, job offers… You name it, Grace Hopper had it!

And to top it off, the programming featured legends like like Anita Hill, Emily Chang, Priscilla Chan and Gwynne Shotwell.

Our Panel
I joined a mix of investors and entrepreneurs to talk about Female Founders. We focused on the structural barriers facing female founders. We were pretty divided on this issue which made for a really juicy conversation.

Some of the investors argued that the venture capital firms are beyond repair and that we need to start from scratch. Some of the entrepreneurs argued that if we don’t improve the cultural realities that many entrepreneurs have to face, we won’t improve the outcomes for female founders.

I thought everyone on the panel had a point. The journey ahead is going to require a unique way of thinking.

Which reminded me of the importance of exploring how other historically underrepresented groups have addressed similar barriers. Being an African-American woman, the one that resonated most quickly to me was that of black people entering into higher education.

Learning from the Journey of Others
While I was at the conference I couldn’t help but getting struck with a little deja vu (twice!).

1. Grace Hopper felt like the National Black MBAA. The National Black MBAA was founded in the 70s to black MBA graduates access positions at top companies. I attended one NBMAA conference when in business school. I received a job-offer from Kimberly-Clark on the spot!

Grace Hopper encouraged the same behavior. There is a resume database set up in advance and it is common practice for recruiters to seek out female talent. I saw recruiters from Google, PayPal, Slack, etc. giving offers on site to women who they found to be qualified candidates.

2. Governor Jerry Brown signed an affirmative action policy. He passed legislation in California that mandates every board of a public company to have at least one woman. This sounded really familiar. Almost like affirmative action.

Affirmative action is intended to promote the opportunities of minority groups within a society to give them equal access to that of the majority population*.

All of this deja vu worries me because time hasn’t treated NMBAA and affirmative action well. Attendees at the NMBAA are now about 25% white and most growing industries like tech companies don’t make time for it. Prop 209 was signed into place in 1996 to overturn affirmative action.

So, I think it is important to see this moment of focus on and empowerment of women as fleeting – unless we take serious steps to ensure it is sustained. Giving one woman a job in tech and another a board seat will not save us. This was clear over this past week with the Kavanaugh confirmation. Just because we had enough women in the Senate to overturn Kavanaugh, didn’t mean we had enough votes to keep a sexual predator out of the Supreme Court.

We need to take our action a step further. Increasing diversity is a necessary, but not sufficient step to creating more equality.

What is it about government and corporate institutions that makes diversity so difficult, and how can we change that?**

*https://web.archive.org/web/20150518061955/http://blogs.law.harvard.edu/sharamkohan1/affirmative-action/

**More on this in upcoming articles! Still teasing through my thoughts. I always welcome your opinions, you can find me here on Twitter @sydneypaige10.

Why I Decided to Become Pipeline Angels’ 1st VC-in-Residence

In September, I added another job to my title. I’m still the Investment Associate and Head of Ops at Precursor Ventures and have now joined Natalia Oberti Noguera and her team at Pipeline Angels as their first ever VC-in-Residence.

It started with a simple e-mail. I’m not yet an accredited investor, but I was inspired with what Natalia was building. So I filled out the Pipeline Angels application and included a short note about how excited I was to get involved wherever I could be useful. Luckily, my application aligned with a new idea Natalia had brewing to get more women like me involved in Pipeline Angels.

Natalia and I hopped on the phone and she shared her vision for extending her pipeline initiative to not just help women and non-binary femmes become angel investors, but also help women, non-binary people, and men of color become GPs at investment firms.

The road to GP is usually paved with a stint in angel investing and a demonstrated ability to bring quality LP leads to the table.

But these prerequisites to the job require one huge piece that many women and non-binary femmes lack → access to capital.

As a VC-in-Residence, her vision was that I would be given the opportunity to learn both. Through working on a team alongside angel investors, I would get to learn the ins — and — outs of the angel investment process, support their decisions on who to invest in and be a contributing member of their investment team. Through working with accredited investors, I would be able to build relationships with women and non-binary femmes who could be tomorrow’s LPs.

As Natalia put it: Pipeline Angels created the role of VC-in-Residence to inspire our members and broader network to help change the face of venture capital by becoming LPs in VC firms led by #morevoices.

I’m grateful for Natalia’s vision and even more grateful for Precursor Ventures’ sponsorship. Professional
development opportunities in venture capital are few and far between. I’m lucky to have found a crew that understands the importance of growth.

Interested in learning more? Check out Megan Rose Dickey’s feature about the VC-in-Residence role in TechCrunch.

Why I Decided to Become Pipeline Angels’ 1st VC-in-Residence

In September, I added another job to my title. I’m still the Investment Associate and Head of Ops at Precursor Ventures and have now joined Natalia Oberti Noguera and her team at Pipeline Angels as their first ever VC-in-Residence.

It started with a simple e-mail. I’m not yet an accredited investor, but I was inspired with what Natalia was building. So I filled out the Pipeline Angels application and included a short note about how excited I was to get involved wherever I could be useful. Luckily, my application aligned with a new idea Natalia had brewing to get more women like me involved in Pipeline Angels.

Natalia and I hopped on the phone and she shared her vision for extending her pipeline initiative to not just help women and non-binary femmes become angel investors, but also help women, non-binary people, and men of color become GPs at investment firms.

The road to GP is usually paved with a stint in angel investing and a demonstrated ability to bring quality LP leads to the table.

But these prerequisites to the job require one huge piece that many women and non-binary femmes lack → access to capital.

As a VC-in-Residence, her vision was that I would be given the opportunity to learn both. Through working on a team alongside angel investors, I would get to learn the ins — and — outs of the angel investment process, support their decisions on who to invest in and be a contributing member of their investment team. Through working with accredited investors, I would be able to build relationships with women and non-binary femmes who could be tomorrow’s LPs.

As Natalia put it: Pipeline Angels created the role of VC-in-Residence to inspire our members and broader network to help change the face of venture capital by becoming LPs in VC firms led by #morevoices.

I’m grateful for Natalia’s vision and even more grateful for Precursor Ventures’ sponsorship. Professional
development opportunities in venture capital are few and far between. I’m lucky to have found a crew that understands the importance of growth.

Interested in learning more? Check out Megan Rose Dickey’s feature about the VC-in-Residence role in TechCrunch.