Why I’m Reimagining America’s Healthcare System

I grew up in the healthcare system. As long as I’ve lived, my dad has been a kidney doctor. I remember spending days I took off from school for being sick in his doctor’s office and following behind him as he would greet his patients one by one at a dialysis clinic. I remember watching him take tests to continue his board certification. I remember the lovely nurses who gave me all my shots and took extra good care of me because I was Dr. Thomas’ daughter. It was fun!

I also remember the day my dad came home and told me he didn’t want me to be a doctor. He said that his work was not like it used to be. It was harder and harder to make a living and really impossible to make a life (he was on call all the time).

Despite this lifelong education in healthcare, when I got into venture, it took me a while to start getting excited about healthcare investing because I felt like there was just so much to learn. Like you couldn’t invest in healthcare unless you had spent 10+ years working full-time in a healthcare system. It reminds me of a quote in Angela Davis’ book – Freedom is a Constant Struggle – where she talks about the challenge of getting people interested in building solidarity movements for the people of Palestine. She says: “too often people feel that they are not sufficiently informed to consider themselves an advocate of justice”. And it is so sad.

How much should you really need to know to be an advocate of justice? When a system deliberately obscures how it works so much so that getting involved in it feels “overwhelming” – who does that benefit? The advocate or the status quo?

All that being said, I did start reading about the healthcare system more generally. I was introduced to An American Sickness by a friend of mine and it was such a wild read. My final conclusion was that every single piece of healthcare is intricately linked to another piece in order to reinforce the underlying system. It is impressive and really terrible for citizens. I recommend it to anyone looking for window into the healthcare system.

This inspired me to focus on companies that were building radical healthcare solutions. It bears mentioning the definition of radical which is: of, relating to, or proceeding from a root. In order to fundamentally disrupt our current healthcare system -which is generating unheard-of profits to healthcare leaders while still inflicting economic uncertainty on the masses – we have to get to the root cause of it, which for me meant investing in companies that are challenging the current system with alternative systems.

How to support Black Women emerging managers in VC

There has been a lot of ink spilled on how to support emerging managers more generally in VC. A lot of it is written by First Republic Bank’s Samir Kaji. I am really grateful for his writing and think it adds a lot of value and context to this conversation!

One thing that I think is missing from this conversation is the discussion on how to support Black Women emerging managers in VC. I think that Minda Harts writes a lot about how to support black women in the work place generally so that should also been used as a preface to this article – if you have not read The Memo by Minda Harts book, stop now and pick it up! It also adds a lot of value to this conversation and is useful context to have before engaging here.

Also for context, I am writing as experience as a Black Woman in Pre-Seed investing. What Black Women in Series A/B/C+ investing need might be different.

As an emerging manager and a Black Woman, I have been thinking really deeply on ways that I have had people show up for me to get to this point and ways that I wish people would have showed up for me. I wanted to write this down to share tips with people who are exploring ways to support other Black Women in VC. The hope is that every Black Woman in VC who comes after me has an easier ride. Because frankly, these past 4+ years have been a rollercoaster!

1. Answer their e-mails or LinkedIn messages – better yet, e-mail them!

One thing that I still have a chip on my shoulder about is the list of people who when I was first starting out in this industry did not respond to my cold e-mails or LinkedIn messages. I also still remember, fondly, those who did respond. One of those folks was Scott Belsky. I cold e-mailed Scott Belsky and he responded with a single line that included “sending my best”. And let me tell you, that was all the encouragement I needed at that moment. I was so bolstered by that because someone who I saw as “powerful and successful” took time to invest in e-mailing me back.

I wish though, when I was first getting started, that more GPs at funds e-mailed me first. I know that it is not every day that a black woman gets hired in VC, and I think it’s important that the greater VC community – including but not limited to the Black VC community – pays attention to, and celebrates those hires. My request is not even that you do something big like “grab a coffee” or “go on a walk” with that new hire. Instead, it is that you share a little bit of encouragement. These can make a world of difference. An e-mail letting folks know that you see them. Letting them know that you are wishing them well. Letting them know that you are grateful they are in this ecosystem. These are the things I hope younger Black Women in VC get from allies.

2. Support the deals they bring to the table

One of the pieces of advice I got when I first got into VC is that – succeeding in VC is relatively easy, all you need to do is “find good deals”. That advice really rubbed me the wrong way. Because in VC, who decides what is a “good deal”? As the old saying goes, one person’s trash is another man’s treasure. I think it is true especially in VC. And in early-stage VC, whoever has the purse strings gets to be the final say on whether or not that is a “good deal”. Because if folks have uniformly agreed that a deal is “bad”, then more often than not, the company does not get access to the capital they need to prove these folks wrong.

So my advice to people who have the purse strings is, critically evaluate what you think is a “good deal” vs. a “bad deal”. For many, I assume that part of the calculus of whether or not the deal you have been presented with is good vs. bad is whether or not you trust the person who has presented you the deal. Why do you trust this person’s opinion so highly? Is it useful to trust this person’s opinion so much more than others’ opinion? Especially on a company that is building a future that none of us can predict?

I think once people critically examine why they green light some deals over others, the bias will start to expose itself.

How can you offer the same benefit of the doubt to people outside of your “circle”? I think one way is to trust that they are bringing some unique insight to their deal that you are not capable of having because of your differing backgrounds. Once you acknowledge their insight, put capital behind it. Let their insights guide deals that you wouldn’t have otherwise invested in and see how they do.

When reflecting on your carrier as an ally, I hope that one of the things you factor in is not how many IPOs or shots on goal you achieved, but how many GPs have you created. How many ideas have you greenlit from URM communities? How much power have you given away in order to create a more equitable (and honestly more interesting!) world?

3. Sponsor their promotions

Over the past four years, I have had the privilege of watching more black women enter venture. I started tracking the growth of this community in 2017 here. One of the things that has been really amazing to watch is the promotion and growth that I’ve seen folks go through from Analyst to Principal. The thing that has been missing though, is the promotion to GP. In almost every case, Black women have only received a GP title if they have started their own funds. This is unsustainable. Partly because, given the wealth inequality in the US, Black women generally have 10x less capital themselves and generally less access to capital than their white male peers.

So why have I yet to see one large VC firm sponsor a black woman’s promotion to a GP? This is unsettling and worrisome to me. I am looking forward to watching this change happen sooner rather than later. A great example of what this could look like is what Jesse at Flybridge built with Lolita Taub. I think it’s such an amazing example of what sponsorship looks like and how it can leverage the skillsets of both parties to create something were 1+1=10.

Individuals > Symbols

A few weeks ago, two big things happened. Beyonce dropped Black Is King on Disney+ and an article came out that shared that Kamala Harris has been undermined by the VP Search community for being “too ambitious”.

The attacks on both Black women started immediately. From Beyonce’s art getting critiqued as celebrating imperialistic, capitalist societies to Kamala getting the feedback that she is just too conservative and also too ambitious to serve as a VP pick.

I got really angry by these critiques. Part of it is that, I identify with both of them as a Black woman who also has chosen to work within imperfect systems. (Frankly, if you are a Black woman who participates in the US in any way – buys food/clothes/shelter, you have chosen to work within an imperfect system, but I digress…)

Part of what I (and I assume Beyonce and Kamala) deal with when you choose to become leaders within these systems is the psychological trauma that often occurs as “the only”. We chose to stay within these structures in order to make them more perfect for the many who are kept outside of them.

This labor is painful, mostly invisible and, more often than not, unpaid.

As a result, I’m deeply skeptical of outside critique on this labor. I have received too many disingenuous critiques to take them seriously. I will never forget the feedback I received when I decided to boycott UC Berkeley-Haas School of Business because they only admitted 5 Black kids into the MBA Class of 2020. My classmates and members of the Berkeley-Haas administration shared with me that boycotting isn’t nice or effective, completely dismissing the years I spent on campus working within the system of Haas to help it become more inclusive. It turns out that the boycotts were effective because they figured out how to admit significantly more Black students the following year. I believe that they were most effective because they were done by a previous student who had deeply studied the institution. I knew which media outlets to leak the story to, I knew which people on campus would be my allies, I knew how to navigate the politics among those on campus who would be my detractors.

This is one example of countless others I can point to over my career and I’m sure many fellow Black women have similar stories.

So, before I accept any inkling of negative feedback of Black women who are leaders within imperfect systems, I have come up with a list of questions first to qualify this feedback. Through the qualification process, I hope that it helps all of us understand more deeply how connected we truly are.

The main questions, I have are:

How do we ensure that we are holding every person within the system equally accountable?

Is your critique of this black woman a critique that you also have of every other person who has operated in this way within this system? If you don’t know the answer to that question, why have you chosen not to research others within this system? Do you have unreasonable expectations of the labor of black women compared to the labor of white men?

What about the critique that you have of this other person are you also perpetrating? How are you holding yourself accountable?

Another way of putting this is: What are you asking this person to do/expecting this person to do that you haven’t done? Why haven’t you done it?

There is an episode of The Good Place where they figure out that nobody has been admitted to heaven for the past 500 years. Essentially, they realized that even people who were trying to be so perfect weren’t able to earn enough points to get into heaven because of the negative externalities that their efforts created. I thought it was such a great illustration of how we are navigating a deeply complex world and have to make trade-offs every day.

When we rush to judge without the full context – of both the other person and also of ourselves (true self reflection is hard and too rare), it makes me queasy. I’m not saying that full context removes accountability, I’m saying that full context forces us to move from treating the other party as a symbol to an individual. It also forces us to explore and recognize our own agency.

Reflections on Imposter Syndrome

A few things happened yesterday that got me thinking about this. The first is seeing this post by Jenna Wortham on Twitter. She is referencing the fact that many media companies are now realizing that they have created hostile work environments for black people.

The second was an interesting conversation with my friend who mentioned that she didn’t understand why more white people did not see the importance of racial equality. I responded that this was probably a response born out of their own insecurity. For if there was racial equality and they didn’t have white privilege, where would they be? Would they be worse off than they are now? (answer is probably yes)

This got me reflecting on my own issues with imposter syndrome. And now I think I have a deeper clarity about what that means for me. So many black people have been excluded from racist institutions. As a result, so much greatness has been excluded from racist institutions. Because I have succeeded in spite of this, I am left with a less great competitive set. So my imposter syndrome comes not from the fact that I don’t belong with these other white people, it comes from the fact that maybe none of us belong. Maybe there is a completely different set of black, white, asian and latinX people who – if we had anti-racist systems – would be standing in our places.

So my imposter syndrome is actually not about me feeling less than great. I think I am pretty great actually. It’s about the sadness I have that I could be greater, could get better, could be more challenged if I was given the opportunity to compete with the best. And I believe that many, if not most, of the best are left out and/or pushed out because of racist policies and institutions.

None of us in any of our industries can write ourselves down as the best, the greatest or a member of the “midas list” until the industries themselves are anti-racist. To do the former before the latter is untruthful.

The Allure of the Black Messiah

“You’re organizing people to be self-sufficient rather than to be dependent upon the charismatic leader…the most important thing was, and still is in my mind, is to develop people to the point that they don’t need the strong, savior-type leader.” – Ella Baker, 1968

“The good news is that racist and anti-racist are not fixed identities. We can be a racist one minute and be an anti-racist the next. What we say about race and what we do about race in each moment determines what, not who we are. I used to be racist most of the time. I am changing. I am no longer identifying with racists by claiming to be not racist. I am no longer speaking through the mask of racial neutrality. I am no longer manipulated by racist ideas to see racial groups as problems. I no longer believe a black person cannot be racist. I am no longer policing my every action around a white or black judge trying to convince white people of my equal humanity; trying to convince black people I am representing the race well.” – Dr. Ibram Kendi from How to Be Anti-Racist.

This past week was devastating. With the killings of Breonna Taylor, Ahmaud Avery, George Floyd and the countless others who we will never know, it seems like white america has finally decided that black people are important to listen to.

Black people have been and will continue to be important to listen to. I worry though, that in an effort to offload the work of critical thinking, white (and black) people will gravitate to a Black Messiah. Someone who tells them exactly what to think so that they don’t have to think for themselves at all and also helps them offload some of the guilt of participating in a racist society for so long which prevented them from listening to and believing in black people in the past. The work that needs to be done cannot be offloaded onto a black messiah. The work is deep, personal and painful reflection on how your behaviors have contributed to (& if you’re white), and benefited from) white supremacist institutions.

How I Built a Track Record in VC Without any Money

One of my goals is to use my voice more. That means owning things I’ve learned with hopes that it can help others. This feels very uncomfortable to me! Anyone who knows me knows that I am more of a show, not tell type of a person. But as I’ve grown more comfortable in my skin, I have realized that I must tell my own story. This gives me serious anxiety – but alas, every time you try something new, it feels unnatural and uncomfortable. So in the name of growth, I’m working through it. A few days ago, I listened to Brene Brown’s new podcast on FFTs (f*cking first times) and that gave me the extra bit of courage I needed to post this.

I hope this post is useful to any and everyone who is trying to figure out ways to demonstrate both to themselves and to others that they are great investors. Without further ado, here we go!


A few weeks ago, I was really excited to see Nate Maslak — co-founder of Ribbon Health — announce his Series A led by A16Z. I met him for the first time almost two years ago when I invited him on my podcast, “Be About It

I created the podcast to show the world that the companies that fit my thesis could be successful. 

My thesis has focused on companies that are building products that give real people more agency over their lives. This can be financial agency, time agency or mental/physical agency.

By demonstrating that my thesis worked, I would also be building my track record. 

What is a track record? It is a scorecard of your investments. It is used by LPs (your investors) to determine whether or not you are a “good investor”. Generally, “good” means that your investments continue to grow in value. 

As CEO/Founder of this podcast, I was in charge of sourcing companies, ensuring they fit my thesis, finding times to meet with these companies, coming up with thoughtful interview questions and also running all of the mechanics behind the scenes to make the podcast live. I purposefully chose founders who were Pre-Seed because that is Precursor’s focus and also because it holds the most risk. If I could demonstrate to myself and the world that I could pick Pre-Seed companies that would advance, then I must be pretty good at finding outstanding founders & companies. 

After spending over a year and countless hours on the Be About It podcast, I was privileged to share time with 15 founders — all of whom I continue to be inspired by. Here is how their companies have grown:

Season 1 (2017) Companies

2017: 7 were Pre-Seed

2019: 3 were Pre-Seed and 4 were Seed

2020: 3 were Pre-Seed and 4 were Seed

Season 2 & 3 (2018) Companies:

2018: 4 were Pre-Seed and 4 were Seed

2019: 1 was Pre-Seed, 3 were Seed, 4 were Series A and 1 shut down

2020: 1 was Pre-Seed, 1 was Seed, 5 were Series A and 1 shut down

One thing I wasn’t expecting was my own growth between my first podcast and the second. In Season 1, I learned so much and brought that into Seasons 2 & 3. You can see it clearly in the numbers — Seasons 2&3 had a higher graduation rate than Season 1. 

The portfolio continues to mature and I’m excited to add another to the Series A list with Ribbon! 

The thesis behind my podcast — to find companies building meaningful businesses that provide mass markets access to what previously was held by only a few — is the same one I hold today as I enter into a full-fledged investing role at Precursor with the ability to make my own decisions and trust my gut. 

It’s exciting to enter into this new role with this track record and I look forward to building upon it — with dollars this time — in the coming years. 


The key things that I think are important to building up your track record without money are as follows:

  1. Develop and publish a thesis on what types of companies you like and why
  2. Publicly name companies that fit this thesis
  3. Wait a few years… (I never promised this was going to be quick!)
  4. Follow-up and see if those companies are doing well! 
  5. If they’re not doing well, write an article stating what you think went wrong and start at #2 on this list again.

A few examples of people/organizations that I think have done this well are Ben Thompson at Stratechery and Scott Galloway at No Mercy/No Mallice.


I hope this inspires many of you — particularly those who might not have the accredited investor title or the VC job —  an alternative way to create your own track record ❤ 

Have you also come up with a novel way to build a track record for yourself with limited resources? Or, do you have a company you’d like me to chat with that fits my thesis?

If so, I would love to hear from you! 

You can always reach me on Twitter: @sydneypaige10 or via e-mail: sydney@precursorvc.com


Note #1: More inspiration to everyone building, striving and creating who are also worried about owning their own success 🙂


Note #2: More deep dives into the creation tools behind the Be About It podcast if you’re interested here.


Note #3: There were a few additional founders I chatted with and unfortunately their interviews never made it onto the podcast. I’m still a huge fan of them! I didn’t enter them into the calculations above since I never formally processed their interview. 


Noted #4: Due to technical difficulties, currently, only Seasons 2 and 3 of Be About It are public.

How I’m Managing My Anxiety During Today’s Uncertainty


Since COVID-19 took hold, I’ve been given the privilege of working from home. Now that I have a little more time (no more commute, no more travel between SOMA and Embarcadero and Union Square for meetings, no more “get ready for work” time), I’ve been able to reflect on what I’ve enjoyed in this moment.

That focus on enjoyment has helped curb my anxiety during a time when everything is changing even more rapidly than usual.

I decided to share a list of my favorites here with hopes that it helps some of you as well!

The inspiration behind this list is the amazing Mari Andrew who is able to capture life’s agonies, joys and reflective moments in a way that is viscerally relatable.

#1 Dancing all night to jams that remind me of childhood alongside Janet Jackson and Oprah

Thank you, DJ NICE!

#2 Catching up with another person in VC who has decided that this is the time to invest in companies focused on doing good

#3 Scheduling calls with my best friends in Beirut, Los Angeles and NYC to really check-in on each other

#4 Checking my neighborhood facebook group and learning that my neighbor is offering to pick up and deliver groceries for the most vulnerable in our community

#5 Learning that my cat hates slack notifications just as much as I do

(this is not my cat)

#6 Seeing the flood of announcements on Twitter that people are donating money to charities

#7 Being able to join my dance class with my favorite dance teacher from the comfort of my living room + not feel guilty for ducking out early!

#8 Taking an extra moment between e-mails to really understand the feelings behind my reactions instead of just reacting


Given that my inspiration is Mari Andrew, I felt like I had to end with one of my favorites by her from her book, “Am I There Yet?

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 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.

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.

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.

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

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.