Category: Entrepreneurship

Entrepreneurship

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let me know how i can be helpful

If you have taken a look at VC Twitter recently, you might have noticed the debate taking place around this one phrase: “let me know how i can be helpful”.

Back story: Many VCs end conversations with entrepreneurs who they decide not to invest in with this phrase. It feels terrible to learn that your startup isn’t going to get money from a potential investor. But it can feel like salt in the wound where the person you just spent 1, 2 or 3+ hours with, gives you an open-ended phrase of “support”. The more generalized the feedback, the less actionable — particularly for first-time founders who don’t know what to ask of investors who have passed on investing in their company.

To help entrepreneurs understand what they can come to me for, I hope in this article to outline exactly how I can be helpful.

I’m your girl if you’re looking for an investor who:

1 Is Obsessed with Customers — Particularly those at the Long-Tail. My entire career has been spent trying to figure out how to serve the “hard to reach”. I think figuring out how to communicate and serve this population is one of the biggest challenges organizations face (the government included) and I have gone through many rabbit holes unsuccessfully trying to figure out how to do this well. I would love to help you avoid some of those!

2 Has a Very Different Opinion than Most Investors. As you might have guessed from my answer to the first point, I have spent the majority of my career in the public sector. I’m also black. I also identify as a woman. I also live in Oakland. I did not go to Stanford. I’ve never worked at Google, Amazon, Uber or Facebook. Can I stop now? Essentially, name one thing that you think most investors have in common and I probably don’t have it. So I’m here for you if you are looking for feedback from someone outside of the status quo.

3 Can Provide Feedback Based off of Employee Experience. I have never started my own company. I have also never been a CEO. This I think gives me tremendous empathy for the employee experience. As you are building your company and have questions around employee compensation, roles & responsibilities and want to think through ways to push back against some of the “tried and true” methods and and want to fundamentally re-think how you can organize your organization that both empowers employees to do their best work and also creates a safe environment, I’m your girl.

4 Has an Eye for Process Optimization. When I first joined Precursor, I had to envision all the ways to create processes for the firm that could scale not to 1–10 companies, but from 1–100+ companies. I love thinking through big-picture process design that helps you identify and build towards the goals you seek. As I have been involved with supporting founders at the Pre-Seed stage, what I’ve found is that the beginning stage of beginning a company is a lot of admin — so much admin. So I am happy and excited to help you brainstorm best practices here.

5 Is Obsessed with Complex Partnership Strategies. I have never worked in an industry where I had only one stakeholder. That sounds like the good life! In one of my first roles, I was in charge of preparing public schools over summer so they were ready to open in the fall. I had to think about the Principals, the students, the parents, the district office and many others. I’m used to making sense of, organizing and processing these complex maps and am happy to help you think through how best to do that for your company.

6 Has Relationships Across Diverse Talent & Investors. I never sought out to be “the only” in venture. I know there are amazing people of color investors, engineers, PMs and founders, and when I first got to this industry I looked to build coalitions to meet and support them. I’m happy to help bring these relationships to bear wherever it can be beneficial for all parties involved.

7 Has Seen Over 100+ Fundraising Strategies. Precursor has grown now to serve a lot of companies. Out of Funds I and II, we have invested in over 100 companies. I have seen a lot of permutations of startup growth — from fundraising strategies, decisions to grow to profitability to shut-downs. From this bank of information, I think I’ve developed a healthy amount of knowledge on how to explore any combination of these steps. Always happy to chat through and guide founders through the buffet of options available to them.

8 Listens a Lot More than She Talks. I love to listen and try to come with an open mind to most conversations while actively questioning opinions and ideas. Talking is less interesting to me because I know there is so much that I have to learn.

9 Brings Her Full Self to Conversations. The experience of building something new, asking for help and working with investors puts founders in a deeply vulnerable position. I am still figuring out my footing in service of founders, but one thing I try not to ever do is to compartmentalize your experience or mine in a way that makes things “easier”. I’m here for the messy, the random and the real-life conversations that creep into the everyday life of trying to do something revolutionary — build something from scratch.

10 Can Get You Some Sweet Software Discounts 🙂 I’m good at getting discounts.

Please don’t come to me for:

1 24-hour Support. I’m human, just like you and need sleep so I can be my best self for you, my family, the Precursor team and my community. I’m probably not the best person to support you if you want to talk to me at 3 am, again at 6 am and then once more at noon. To get the best out of me, expect extremely quick responses from 8am-8pm and a delay outside of those times.

2 Immediate Feedback. I’m a deep thinker and journaler! I pride myself in having thoughtful, well-researched feedback for questions or concerns you might be facing as a founder. To that end, to get the best out of meeting with me, send me a few questions in advance that you’d like to discuss and I’ll come prepared.

3 Sunshine and Fairytales. I am very direct and don’t like to pretend about anything. If you are very conflict-avoidant, I might not be a great fit for you.

4 Anything Bro-y. I just can’t with that life.

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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

After that I was promoted to lead and invest in deals at Precursor VC

Now I’ve launched my own VC firm

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

Updated: June 5, 2022

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How to Tackle the Long Tail

I’m now two seasons into my podcast “Be About It” where I interview founders who are solving meaningful problems.
So far, I’ve had 15 amazing founders on my podcast. Each one is solving a real pain point experienced by 80% of the USA — individuals making under $100K and small business owners.

Across the founders I interviewed, there was a single pervasive concern. When you target such a large population, how do you actually reach them? Reaching the top 20% is not easy, but it is relatively straightforward. The toolkit for most includes some cocktail of Facebook/Google ads, App Store hacks and modern design.

Reaching individuals and small business owners located in the remaining 80% is much more complicated.

Their interests are varied, they are not all located in one online community and are very hard to please because they have to see immediate ROI in their purchases.

They do not have excess capital to be as patient as the top 20%.

I saw this first hand when I was working in the NYC Department of Consumer Affairs in the Mayor Bloomberg years. There, I was tasked with managing the product launch of SaveUSA across New York City. SaveUSA was created to demonstrate that a progressive tax policy that incentivized low-income tax filers to save some of their tax refund could impact the wealth gap.

Essentially, I was in charge of finding people to give free* money to. Easy right? No. From the marketing — where do you find low-income tax filers? — to the onboarding & engagement — how do you keep these tax filers engaged over a series of months?, my experience at SaveUSA was a deep dive into the complexities of targeting a diverse population.

In SaveUSA’s NYC campaign, here’s what really worked for us:
Meet folks where they are. I learned how to do taxes (*shout out to VITA*) so that I could help folks with their tax filing and then enroll them into the SaveUSA program. This helped us understand exactly what the main pain points were for tax-filers and address them immediately. Also doing someone’s taxes really builds their trust.
Be respectful of their time. When we incorporated an ability to sign-up for SaveUSA into the flow of tax filing — which was difficult because a critical piece of signing up for SaveUSA included opening a new bank account — we saw a huge increase in take-up rate.
Speak to their best selves. One of the selling points that worked best for us during SaveUSA was speaking to the tax-filers’ best selves. This is especially hard in a culture that treats poverty as an illness. But framing questions around: “How can we figure out how to pay the most critical bills now and save the rest?” instead of “Why haven’t you paid those bills yet?” worked wonders.

It was enlightening to hear additional techniques on how to engage this segment from the founders I talked to on the podcast.

Here are the top 3 recommendations I learned from the founders I interviewed:
Do your research. Jimmy Chen at Propel shared how important it is to conduct deep customer interviews to understand how to build the most intuitive product possible. 🎧
Don’t reinvent the wheel. Chai Mishra at MoveButter discussed how important it is to work within the ecosystems that exist for the communities you are trying to serve. 🎧
Build a movement. I learned from Beatriz Helena Ramos at Dada how to help creators build communities among themselves in order to catalyze an even larger movement. 🎧

I am inspired that people are proactively exploring the long tail wave of consumers and coming up with creative solutions. At the end of the day, it reminds me that the most important thing founders can build is a strong community.

If you’re interested in learning some of these hacks, check out the past couple of seasons of “Be About It.” You can listen to it anywhere — from Soundcloud, Breaker to Apple Podcasts.

I’d love to hear from you! What have you learned from the founders in the episodes? Do you have ideas of founders I should talk to? Leave me a comment below or reach out to the podcast on Twitter @thebeaboutitpod.

*The money was not technically free. The participants received a 50% match for every dollar they saved for 6 months, up to $500.

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How Can VCs Make Entrepreneurship Suck Less?

So much ink has been spilled on how difficult entrepreneurship is.

And rightfully so! The more I talk to entrepreneurs, the more respect I gain for them. Living years without a paycheck, managing investors who are telling you to run fast in 10 separate directions and working with a team who is there because they believe in you when you aren’t sure if you believe in yourself is physically, mentally and emotionally exhausting. Yet, much of the VC rhetoric I hear praises someone’s ability to go through this process. They glorify the struggle. They say that if it was easy, everyone would do it.

But I think there is a fundamental problem in the entrepreneurship ecosystem today.

It is becoming so hard and so irrational to start companies that the people who we need the most (i.e. rational, smart people) are opting out. I am inspired by this post on Why More Women Don’t Run for Office. So much of what Raina Lipsitz discusses can be applied to entrepreneurship.

It doesn’t make any sense for highly qualified women (particularly women of color) to start companies.

After foregoing wages that they need to feed their families and communities, they are going to go through a round of disappointing interviews with VCs that will give them a 1-2% chance of receiving funding.

If we continue to structure a path to successful entrepreneurship as we do, we will continue to get the egomaniacs to enter and succeed.

Do you only want Travis Kalanick 2.0 running the companies of the future? I don’t. So how do VCs make entrepreneurship easier? I think there are a few fundamental things that VCs can do to make entrepreneurship more friendly. We should normalize taking a meaningful salary.

  • I have seen burn rates all over the place. Entrepreneurs I’ve talked to are everywhere between living at the poverty line to living in the SOMA Grand. This is crazy.
  • Why isn’t there more excitement amongst VCs to help entrepreneurs meet the lowest rank of Maslow’s Hierarchy of Needs? Why isn’t there more acceptance of the fact that the opportunity costs to these individuals is high already – with or without a salary?

We should treat entrepreneurs with humility.

  • As Kanye put it – You Ain’t Got the Answers, Sway. Entrepreneurs are building from scratch. Yes, we may have seen things similar to what they’re creating in the past, but almost everything since then has changed. The timing, competitors, funding environment.
  • We have so much to learn from each and every entrepreneur that walks through our doors. And the only way we’ll succeed in our jobs is if we take each opportunity to soak up the knowledge from these founders seriously and respectfully.

We should not ask entrepreneurs to sacrifice their lives for their companies.

  • When we’re doing this, what we’re saying is – making me money is more important than anything else you could be doing.
  • NYTimes describes this phenomenon in a recent article: “The guy is developing an app that lets you visualize how a coffee table from a catalog might look in your living room. I suppose that’s cool, but is it really more important than seeing your kids? Is the chance to raise some venture capital funding really “the ultimate reward”?” 

What is the ultimate reward is deeply personal to each person. But I hope that as VCs, we empathize with entrepreneurs who may have thoughts, lives and dreams outside of building the company we invested in. They are better entrepreneurs for it.

Sydney Paige Thomas