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…

Risk Analysis: Failed Company Early Employee vs. Founder

One of the weird things about being in VC now for almost 5 years, is that there are some topics on VC Twitter that feel like groundhogs days. They are debated in earnest at least once a year, and nobody in that conversation seems to remember or care that this happened exactly the same way a year prior. I think this probably happens in many crevices of the internet, that is just the one that I occupy most time in so I see it very plainly.

One of those groundhog day topics is the VC Twitter version of oppression olympics. It’s the discussion about what is riskier: to be an early employee or to be a founder. The funny part about this topic is that most of the people who weigh in are founders. They weigh in as if they can speak for both founders and employees even though they have only been founders. In many cases, they are airing out their own traumatic founder experience and can’t imagine someone else saying that their experience could be more (or equally) difficult. Especially if those people are their own previous employees who they paid when they were depriving themselves of any salary. I get it, being a founder is an extremely isolating, expensive, and overwhelming experience. And I don’t want to take that away from anyone.

My experience though has only been as an early employee at Pre-Seed/Seed* companies that failed. The conversation I think we aren’t having enough is how to process your work product and history after a company you worked for fails. Especially as that pertains to your own feelings of self-worth. From my perspective, in every early startup I worked for, I was underpaid, overworked, and had few (or 0) coworkers to lean on or to learn from. If I had to pick the most important part of the riskiness equation though that made the early employee role that much more risky for me is that in those roles, I didn’t actually learn any skills. Instead, because I was constantly reacting to ever changing inputs, I had to rely on what I already knew to produce some semblance of a useful output. If I didn’t know something, Google was my best friend. The expectation at an early stage company is that as the company grows, the resources it has grows. Those resources can be used to help you hire a team, to get you access to information databases, to increase your pay. But what happens if those resources never arrive?

As a non-technical early employee, so much of the work that I did at the startups I worked for was very tedious, very unsophisticated labor. The lasting impact, in many cases, was nil because things changed so constantly. You didn’t know if anything you built or created would last until the next week. In my first role, I was in charge of supporting one person on the team to help her collect data into her spreadsheet to track the sustainability of the company. Then I moved into a more R&D role to explore a product launch (the product never materialized). In my next role, at a second startup, not a single one of the projects I managed actually materialized. So after a few months of that, the CEO transitioned me into more of a sounding board/advisor role where I was basically just performing emotional labor. Even in my early days at Precursor, I spent much of my time building (and then scrapping) CRMs, and tracking down a lot of paper trails. The administrative labor was overwhelming.

The hard part too about the employee vs. founder conversation is there is a strong bias towards founders. They are the avengers, the masterminds, the leaders. So as a result, “failed founder” has a certain gravitas to it that failed employee does not.

In my work as an early employee, on the good days, what I gained was perspective. I was given a spot in a growing ecosystem that I cared a lot about and so I was able to use that vantage point to better understand how I wanted to navigate that ecosystem. On the bad days, I was so exhausted by my ever-growing workload that I was in a constant fight or flight mode – unclear where I could even fly towards…

Obviously, things turn out well in the end. The third startup – Precursor – ends up not failing, my role expands and I get to grow in my own skills and experience. But I want to be honest about my early experiences so that others know what the real cost of joining an early company can be. I am also using my new position as an investor in companies to coach founders I work with on how they can be more thoughtful about their early employees and my hope is that this next generation of early employees receive the skills, experience and knowledge they need to fly towards something amazing.

*I can’t speak to the risk/reward profile to employees who join Seed+ companies

Inspiration from this post comes from:

1) a few conversations I’ve had with our MBA interns who are thinking about that first employee role at startups

2) a few conversations I’ve had with our founders – many of whom who have been founders before, but few of whom have been early employees are failed companies before

3) Yoni’s recent post – so honest, loved it!

4) Karla’s recent post really spoke to me and this is exactly the type of leader I hope to become, which requires being honest about the work I’ve done and how it impacted me

5) Ashley Ford’s interview on Brene Brown’s podcast about her memoir. Her decision to own her own story despite whether or not it implicated others is powerful and I plan to do the same. My story is mine.