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.

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.

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.

The Power of Language

In the venture capital industry, there are so many “buzzwords”. Almost all of them can be found on Twitter with a hashtag attached: #blockchain, #ai, #futureofwork. These shortcuts are helpful to manage the overwhelming amount of “new, exciting ideas.”

VCs try to put these buzzwords on products and ideas in order to group their thinking. If something is in a specific buzzword category, you can quickly come up to speed on the market, KPIs — basically, the things that matter. If something is outside of that category, it takes a more time to understand the entire diligence process.

This can lead to the known buzzword > the unknown unique idea.

This is disconcerting for a number of reasons — including the confirmation bias effect, and the creation of herd mentalities. Unfortunately, I have seen this trickle down to entrepreneurs who are looking to hire quickly and exclusively look at candidates who have previous experience in similar companies with buzzwords they can understand.

The biggest downside of doing this is you miss out on swaths of the population who could:

  1. Be uniquely qualified for these opportunities and,
  2. Bring with them a level of critical thinking that often comes with having perspectives across industries.

I wanted to create a thesaurus translating public sector experiences to private sector buzzwords

As a veteran of the public sector myself, I know that my transition to the private sector was made infinitely easier when I figured out how to talk about my past in language that private sector people understood.

The main audience for this includes:

1. Entrepreneurs who are looking at candidates and don’t know how to decipher their background.

2. Public sector candidates looking to make the switch and exploring ways to talk about their experiences

3. And, to help inform the public about how to interpret similar work done across industries who use different vernacular or “buzzwords”.


Development/Gifts (i.e. Chief Development Officer)

What does this mean? This person has a history in fundraising across multiple stakeholders — foundations, HNIs, and private companies.

How does it translate? Business development or growth hacking

Outreach (i.e. Public Outreach Associate)

What does this mean? This person has a history in managing a brand.

How does it translate? Marketing, product marketing or content strategy

Program (i.e. Program Assistant)

What does this mean? This person has a history in managing cross-functional teams.

How does it translate? Analyst, business operations, project management

Membership/Volunteer (i.e Membership Coordinator)

What does this mean? This person has a history of building communities.

How does it translate? Customer success

Social (i.e. Social Worker)

What does this mean? This person has a history in developing a deep understanding of their clients needs and providing them with support to address these needs.

How does it translate? Therapist, venture capitalist ( ?)


I hope this helps! Are there other experiences I should include? Let me know by leaving a note below or e-mailing me at sydney@precursorvc.com.

The List of Black Women in VC

A compilation of black women who work in the venture capital ecosystem

When I first arrived into the venture community, my first instinct was to find my people.

The List of Black Women in VCWhen I first arrived into the venture community, my first instinct was to find my people. As an outsider in this new, foreign space, it was important that I build a sub-community within venture in which I felt safe.

So, I started building the Women of Color in VC network with Siri Srinivas. Since our first dinner last November, I have had the privilege of getting to know so many amazing women.

However, in this post, I want to highlight the black women in venture. We are here and the numbers are growing.

It is important that we recognize, listen to and encourage these women as we look towards building an inclusive venture ecosystem.

I’m hoping this list can be particularly helpful for:

Startups building boards

VCs adding new GPs or Venture Partners

Conference Organizers developing rosters of panelists and keynote speakers

I look forward to seeing these amazing women represented more in the venture capital community and growing this list exponentially in the years to come.

Investors

Kesha Cash — Managing Partner, Impact America Fund

Lisa Lambert — Managing Partner, The Westly Group

Daphne Dufresne — Managing Partner, GenNx360 Capital Partners

Tracy Gray — Managing Partner, The 22 Capital Group

Arlan Hamilton —Managing Partner, Backstage Capital

Shauntel Poulson — General Partner, Reach Capital

Karen Kerr — Senior Managing Director, GE Ventures

Lisa Coca — Managing Director, GE Ventures

Richelle Parham — Partner, Camden Partners

Danielle Morris — Partner, Jumpstart

Monique Woodard — Venture Partner, 500 Startups

Anne Richie — Venture Partner, Jumpstart

Ulili Onovakpuri —Principal, Kapor Capital & Venture Partner, Fresco Capital

Brittany Davis — Principal, Hello Angels

Nicole Walker — Principal, Baird Capital Ventures

Gloria Ware — Principal, Jumpstart

Stefanie Thomas —Senior Associate, Impact America Fund

Megan Maloney — Associate, General Catalyst

Jillian Williams — Associate, Anthemis Group

Sydney Thomas — Associate, Precursor Ventures

Adina Tecklu — Analyst, Canaan

Sydney Sykes — Analyst, NEA

Sonya Powell — Analyst, Jumpstart

Ita Ekpoudom — EIR, Plum Alley Investments

Candice Mathews — Executive Director, Hillman Accelerator

Roxann Stafford — Director of Programs, Matter.VC

Lauren Booker Allen — Senior Manager, Omidyar Network

Kimberly Marshall — Senior Program Officer (Tech Investments), Gates Foundation

Ebony Pope — Senior Manager, Village Capital

Marilyn Waite — Senior Manager, Village Capital

Diane Henry — Angel

Lauren Bias — Angel

Kathryn Finney — Angel

Gayle Jennings O’Byrne — Angel

Lorine Pendleton — Angel

Lisa Skeete Tatum — Angel

Operators

Saydeah Howard — SVP of Talent and Venture Services, IVP

Mandela Schumacher-Hodge — Portfolio Services Director, Kapor

Onyedikachi Achilike — Program Manager, Newark Venture Partners

Abyah Wynn — VP, Trimantium Capital

Timmeko Love — Business Development, Mayo Clinic Ventures

Kendall Sherman —Community Manager, Flybridge

Natanya Montgomery — Knowledge Coordinator, First Round

Did I miss someone? Please let me know! You can reach me here: sydney@precursorvc.com

Timeout — Why did I want to become a VC again?

It has been a week in the Valley for the books.

As all of the industry’s ugliness comes to light, I am forced to call a time out and reflect on why I wanted to be in this business in the first place. Underneath the surface of this question, lays an even bigger question: What does a successful VC look like to me?

From my discussions with GPs, it seems like everyone has their own definition. To some, a successful VC is the one who has the fancy startups next to their name on their Twitter handle (i.e. early investor in @Uber). To others, a successful VC is one who took their learnings from their time at a16z and applied it to start their own company. And to a few, a successful VC is one who built a generation of companies that will contribute to a more healthy workforce.

To me, I have realized that so much of what I want out of being a VC is not the picking, not the glamour and glitz, it’s the boring, unsexy part of being an ecosystem builder. This may in large part be a function of my background. Working across almost 5 different industries — federal government, local government, philanthropy, CPG, startups and now VC — will do that to you. I see implicit connections that require fluency in the language of different institutions.

This fluency inspires me to build bigger, larger, more stable bridges, than narrow silos.

That doesn’t mean that picking great companies doesn’t matter. If you want to stay in business past Fund I, it definitely does! But I refuse to pick companies or entrepreneurs who are not as committed to building the type of VC ecosystem that is required for it to flourish — diverse, empathetic even when it hurts and driven to do things the right way, not the fast way.

My thoughts are that these are the kinds of people who, once successful, will remember what being without power felt like so well that they never corrupt themselves with it.

I’m excited to see what happens as the bad actors are excluded from the party, leaving space open for the many different types of VCs to finally get their invitations. The ones who are here not just for the power, but for far more interesting, nuanced and inspiring reasons.

What does an associate actually do?

Now I’ve really got to figure out what’s going on.

Prior to joining Precursor Ventures, my research into Venture Capital had focused on the high level — I followed partners, kept up to date on trends and explored startups I thought were interesting.

In informational interviews with associates I focused too much on questions like, “How did you get this job?”, “What should I prepare for in the interview?”and not enough on questions like, “What do you do all day?”

Once I got the job ( ?) and started asking my peers the third question, I realized the answer varies widely across firms. This is especially true when you take into account the size of the firm. Associates at firms that employ 100s of people have positions that look much different than those at firms that employ <5 people (like ours!)

So I’m going to focus on what associates at firms with <5 people do. As a startup, my role ebbs and flows with the needs of the organization. Overall though, associate roles at small firms can be bucketed into three areas: ops, sourcing, diligence.

Operations

In a company with fewer than 5 people, we mirror a lot of the companies we back in that, we are essentially a startup ourselves. So what is operations? Think bizops and you’re about there. In most small firms, the major functions like Finance, Design, Web Development are outsourced and it is the associate’s role to consult, review and improve these areas.

However, the breadth of the operations work can be expansive — from exploring investor CRM systems to building community efforts for the portfolio.

Sourcing

Associates are often tasked with searching for startups that the firm might be interested in investing in. In order to accomplish this, we need to first get a strong pulse of the markets the firm invests in. That means taking many meetings with people who have different vantage points of the same market — founders, other VCs, experts and customers.

Diligence

Once the startup is found, a lot of research has to be complete in order figure out if the startup has the potential to become a dragon or unicorn. In the Pre-Seed stage, the majority of that research is done on the people and the ideas, not the numbers. So we take time to dig into the founders’ history — who knows them well? How do they rise to challenges? What do their relationships with their co-founders look like? — in order to build a strong understanding of their ability to execute against their vision. We also dig into the ideas by asking questions like, “Are there customers searching for this solution already?”

If I had to pick one thing I didn’t realize would be a big part of my job though, it would be networking. Venture Capital is such a small industry that it still operates a little bit like a club. In order to get in, you have to make yourself known and be known. If you’re an extrovert (like me) that can be a lot of fun!

I hope this was helpful and would love to get your feedback. What did you think?