They are founders FINDING founders. Siggi came into my life as the leader of an office I took portraits for. THANKFULLY, because since I've followed her careful advice, felt her support for my work and now I live in full awe of her ability to lead an office of founders while co-owning an elite networking group of women leaders. AND she introduced me to Eva, her co-founding partner in crime. A woman I've yet to discover more about but can only imagine given the company.
Tell me more about what you two are currently working on together.
Siggi: Women in Enterprise (WE) is a community of 100+ women interested in professional development. We host dinners with about ~10 women, and we do it approximately monthly. For each dinner, we choose a topic—sometimes industry specific, like “using patient data in B2B health tech,” and sometimes cross-functional, like “enterprise product management”—curate the guest list, and lead discussions around the topics. We start the dinner with introductions (we often don’t know these people ourselves, since we find them on LinkedIn!) and fun facts; after the meat of the discussion, we finish with a round of “asks” and “offers” from everyone at the table.
The idea is that everyone is there to learn and grow, and by the end of the dinner, you will have spent two hours with this amazing group of women and would maybe feel comfortable reaching out to them in the future.
Questions are encouraged. Jargon is publicly shamed. Joking! Jargon is discouraged. :)
Eva: Well said!
Why did you decide to start this group? What excites you about investing in other people?
Siggi: In spring 2017, we were both fairly new to our jobs. It was a hot time for “women in tech” and diversity events, but we were both burned out on being invited to panels of women talking about work-life balance. The trope is that women get together and talk about work-life balance, but that men get together and talk about business. We thought that there was a time and a place, but that we were tired of it being every time and every place. We wanted to go to events that featured awesome women kicking ass professionally because they were kicking ass professionally.
We also saw that a lot of our male colleagues, peers, and counterparts (in Silicon Valley) seemed to have social networks that transacted business, and mentorship relationships with senior people that—surprise!—looked like them. We just didn’t see people who looked like us, aka women, above us, and so started to look around us.
Eva: One of our main responsibilities in venture is to source new investments, and it became clear that a network of deal sourcing/sharing existed but that we weren’t necessarily part of it. I initially tried to assimilate by attending the requisite networking events and striking up conversations at the bar, but I found it exhausting and unproductive. Moreover, I found that I started dressing differently -- more muted, more masculine; the subconscious can play funny tricks. When I found Siggi shared similar sentiments (minus the dressing habit), we decided there had to be a better way.
Siggi: Butting in here, the dress habit was true for me too, now that I think about it. A male colleague made a comment about my looking “dainty” in a dress, and I realized that “dainty” wasn’t really a word I associated with investors. So I backed off dresses for the most part.
Eva: The reality is that there aren’t a lot of women in tech, and there’s even fewer in enterprise tech (i.e. companies selling into enterprises vs. individual consumers). If we could harness this small but mighty army, we realized we could develop our own proprietary network that was meaningful to both us and our jobs.
Now, instead of the emotional drain I used to feel after forced-networking, I come away from each of our dinners feeling energized and recharged. We’ve created a community that’s not only valuable to us from a deal sourcing and diligence perspective but that is truly valuable for the rest of the community members as well. There are female leaders throughout our industry that are key decision-makers and are highly in tune with the direction of their companies and yet are isolated and fairly ignored by the broader tech community. They’re not being asked to speak at conferences and they don’t have an outlet to speak professionally with like-minded people in a similar field or function. Connecting these women—the operators, the entrepreneurs, the investors—has been so incredibly fulfilling.
Siggi: Now we’re approaching 20 dinners!
Before we dig in any further why don't we first DIVE into history about you two. Where did you grow up?
Siggi: This has always been a tough question for me to answer. :) I was a both military brat and a child of divorced parents, so we tended to move a lot. I was born in Germany, moved to Virginia, went to kindergarten in Philadelphia, and moved back to Virginia for 8th grade. In 11th grade, I became a Congressional Page and moved to Capitol Hill. After that, I didn’t want to go back to high school, so I did an exchange program to Germany before college.
Eva: Similar to Siggi, I had a fairly international upbringing. My mother is from Ireland, my father is from Hong Kong and they met in Nigeria. However, after I was born (in Hong Kong), we relocated to Northern California so that my father could attend graduate school and, eight years later, we all became naturalized US citizens. We maintained our new roots in California while spending summers visiting our family abroad.
Where did you go to college—or did you?
Eva: I went to the University of California, Berkeley for undergrad. I was self-programmed to be hard working and execution-oriented, to the detriment of exploring my passions -- so when I arrived on campus, I handed my course catalog to my older brother (also a Cal Bear) and told him to pick classes for me. I majored in Political Science because my brother thought I would find it interesting (and I actually did!), and I majored in Geography because I had optimized a lot of cross-departmental courses. Looking back, there’s a few things I would have done differently :). Luckily, I got a second chance at exploring the focus vs exploration ratio when I went to Wharton for business school.
Siggi: I went to the University of Virginia (UVA) for undergrad. I was very, very lucky that it was my state school. I studied German Language and Literature (because I liked it) and Finance (because I thought it was hard). I was right about both of those being true.
A few years later, I did my master’s degree at Boston University and went to law school at Stanford Law.
After graduation did you know your path or did you want to explore? What sort of experiences can you share that would, looking back, be relevant to who you are today?
Eva: Absolutely not. I financed my own schooling, which meant I had an administrative office job since the age of 16 -- working throughout the school year. As far as I was concerned, I was doing good work and making money. I wanted to make the transition into finance after graduation but I had little concept of my own capabilities and value, despite graduating with high honors from a top university. I was still applying to jobs off Craigslist (!!), when a friend from college offered to introduce me to a hedge fund manager that was looking to grow his team.
What I lacked in finance experience, I made up for in hustle and scrappiness. It was at this job that I had one of my most profound learnings -- in an office environment dominated by men, you will always be different … and that’s not necessarily a bad thing. I had a high EQ and I used it to my advantage -- absorbing everything around me, distilling how/why decisions were made and, in turn, anticipating future needs. Being proactive and acting without being asked is the most impactful thing you can do for your employer and the most fulfilling thing you can do for yourself. My role expanded quickly and I leveraged this growth into increasing career opportunities.
While more of my career has happened since that point (investment banking at Goldman, running operations at a startup, venture capital), I’ve maintained the same approach. Be different, and be really freaking good at it.
Siggi: Both? I definitely thought I knew my path. I wanted to go to law school and to become a big shot bankruptcy attorney for big corporations. There was something pretty glamorous to me about “crushing deals” (quotation marks intentional). I thought I’d be a courtroom attorney on some days, a corporate attorney on some days, and—I don’t know—someone walking around factory floors telling people to shut off machines on other days. I’m not sure that’s actually what bankruptcy attorneys do, but at the time, it sounded awesome.
Before I went to law school though, I wanted to grow up a bit. I liked the idea of a service program (like Peace Corps), and was introduced to Teach for America, a program where new grads and career-switchers teach in underresourced, often underperforming schools in service of closing the educational achievement gap). After school, I moved to Boston and taught 8th grade math. That is, by far, the hardest job I’ve ever had. That’s helped me keep a lot of things in perspective. If I’m having a bad day or mess something up at work, I try to remind myself just how good I have it. I have immense respect for teachers.
After teaching, I went to law school at Stanford (again, thinking I’d be a bankruptcy attorney). Yadayadayada. I’m now not an attorney at all. But that’s a longer story. :)
As far as experiences that are relevant to who I am today? In general, I’m thankful for the people who reminded me that everything I do, I choose to do, that I am responsible for my own happiness, and that it’s never too late to change your path.
Speaking of choosing your own path lets circle back to this group you've nutured. What’s been most challenging about starting it?
Eva: Launching a community and keeping it engaged is time consuming, and you’re looking at the two people that handle every bit of the coordination and logistics. While we started WE to help us with our jobs, it’s not our actual job. Yet we happily spend hours reserving private rooms, researching interesting markets and scrolling through countless LinkedIn profiles to curate the perfect balance of operator, entrepreneur and investor—it’s truly the best part of our jobs.
Also, it's important to address, what if you're not a CEO or top exec? What if you're an incoming graduate looking to build a network or curiously explore? OR you’re older and embrace the “it's never too late” philosophy and want to find a good network of women to grow more with? Is this group for you? And, if not, where can you recommend this crew look?
Siggi: Our group is geared towards women at least a few years into their career—so we can all contribute—but not so senior that we accidentally create a guest speaker/featured guest environment. We’re all peers at the table.
Eva: From our experience with other networking groups, we were cognizant of building a community of peers. We had a hypothesis that women would be more engaged and vulnerable if they were in the presence of comrades, as a wide gap in experience levels often defaults to mentor/mentee relationships. We attempt to incorporate diversity by curating dinners with guests from different educational backgrounds and focus areas but have found that a general balancing of experience levels has been helpful in fostering connections.
Siggi: We’d love to one day include women of all levels of experience, but for now, this focus is important to our building a tight, high-value community. For folks that don’t fit neatly into this group, we recommend looking for another group—check out Tech Ladies, All Raise, YC’s Leap, Women in Product, ...just to name a few—or start your own!
You mentioned that you start every dinner with a fun fact to break the ice. What’s your fun fact?
Siggi: We’ve heard everything from people’s first CDs to their bad dates.
Eva: The bad dates was such a good one! I also like asking our guests about their favorite podcast or binge-worthy tv show, as I’m always looking to add to my repertoire. My fun fact is that I have three passports, and my favorite binge-worthy show is The Great British Bake Off.
Siggi: My fun fact is that I didn’t totally graduate from high school. Also, I’m unsuccessfully managing my dog’s Instagram account. I’m struggling to be a #dogmomager!
And last what is your current good read, magazine, online inspo or podcast? What can we sink our teeth into?
Eva: Everyone should reach Michelle Obama’s biography, Becoming. I wore out my digital highlighter covering numerous quotes and passages in my kindle app. She shared so many truths about career fulfillment, personal sacrifice and the burden/blessing of womanhood. I typically listen to podcasts when I’m multi-tasking alone and want to feel like I’m in the presence of friends -- for that reason, I enjoy Forever35 and Who? Weekly. For a deep dive into the underbelly of the Internet, I recommend Reply All.
Siggi: I’m inspired by all of the female comics on Netflix right now. Check out Ali Wong and Hannah Gadsby. One of my goals for 2019 is to do more to walk-the-walk on feminism, so I’m in the middle of putting together my book list for the year. I’ll check back in!
Finding Founders is an exploration of the person BEHIND the company. Who they were, are and where they’re headed OR rather, blazing a trail to.
On that note, I’d like to introduce Andy Sparks. He’s building something that’s almost hard to understand because it doesn’t exist anywhere else, yet. Which is why I’m documenting his progress. Andy’s come a long way from his conservative, religious roots, to the giant city of San Francisco where he’s co-founded a company already. He’s learned so much and I can see the drive to build, learn and question everything. He exudes it thrillingly.
In your own words please describe yourself with three sentences.
I am a philomath—a lover of learning and studying. I’ve decided to spend my life making it easier for humans to share, criticise, and improve knowledge, as I believe that’s the root of all human progress. I like to drink my beer extra cold and try to remind myself regularly not to take myself too seriously.
Did you always know you'd start a company?
When I was in elementary school, I asked my Mom for a pen and piece of a paper while in line at the grocery store. Apparently I quickly returned the piece of paper to her with my autograph on it. I don’t think I always knew I’d start a company, but for better or for worse the only thing I’ve been sure of is how sure of myself I am.
At 23 what did you think you'd be doing or what were you going to try?
On my 23rd birthday, I watched Netflix on my laptop—perched on top of a cardboard box of my boox—and slept in a sleeping bag on a camping mat in the living room of my first apartment in the Bay Area. I had just drove across the country from Ohio by myself and was waiting for two of my best friends to join a few weeks later so we could build our startup.
At 23, I wanted my company to be successful so I could validate my own self-worth. It didn’t take long for me to learn how weak of a foundation that was to build a company on top of. I knew I wanted to lead people, I knew I wanted to make a positive impact, and I knew I didn’t want my work to make me miserable.
This is not your first company. What are three things you took away from the first company you started here in SF?
Holloway is my fourth company. The first of four was hardly a company. In college, I homebrewed beer with a friend and we had grand plans to create our own microbrewery—this was in 2008-09. I started my second company after college in Ohio in 2011 and convinced two of my friends to move to California to try and get into Y Combinator or 500 Startups. We got into the latter, but I quickly learned that it’s a fool’s errand to start a company for the sake of starting a company. My third company, Mattermark, is my proudest achievement. We build a company that, at one point, had 50+ employees and was doing $4M+ in annually recurring revenue. From that company, I took away three big lessons:
Give us some good fun facts about you.
I have a tattoo of Calvin and Hobbes on my forearm. It says, “The truth is, most of us discover where we’re heading when we arrive.”
Fun fact I wouldn't know.
In 2007, I voted Republican and planned on becoming a Christian preacher. By the spring of 2009 I was homebrewing beer out of my college apartment and wearing a headband.
If you found $100 on the ground you would ______________.
Probably not pick it up out of fear of what would be on the bottom of it
What's the last movie you saw in theaters?
I actually don’t remember.
Next travel destination for work/fun?
I go to New York City for about a week every quarter for work. Every I get back to San Francisco from New York, I’m reminded of how small of a city San Francisco is.
You have a habit you do every day or week?
I have a lot of daily and weekly habits. I get eight hours of sleep almost every night. I go to the gym three times a week and swim at least once a week. I eat lunch by myself and read a book at least once a week and I do the same at breakfast at least twice a week. I try my best not to drink alcohol during weekdays. I make coffee and a drink a glass of ice-cold water every morning. At least once a week, I write for 30-60 minutes to process my thoughts. But people with habits are annoying. They’re self-righteous and preachy. All of my habits are tools I’ve figured out how to use to keep myself from going absolutely bonkers, and I think people should figure out what works for them and then proceed to stop telling other people about all their habits at dinner parties.
Fav bar in the city?
Vesuvio. Hands down. I’m there at least once a week.
Go to Podcast or TV series.
I love The Daily by The New York Times. I listen to it almost every morning on my commute to work.
Book(s) your reading right meow?
I’m currently reading Zen and the Art of Motorcycle Maintenance. I used to cringe when people recommended this book, because it has this cult-like following that made me think it was some pop-cultural faux intellectual garbage. But then my Co-Founder, Josh, recommended it. Josh only recommends good books. Zen and the Art of Motorcycle Maintenance isn’t about zen or motorcycle maintenance at all really. It’s about a the tension between two ways of thinking, external validation, and what “quality” means.” It’s a terrific read.
I’m also about 75% of the way done with The Righteous Mind: Why Good People Are Divided by Politics and Religion. I think every single American—Republican or Democrat—should read this book. It gets to the heart of why we talk past each other when we talk about politics and religion. It’s completely transformed how I see why people are so divided, but it’s also helped me see how companies appeal to our moral sensibilities when selling products.
In case anyone wants to go deeper, I keep a full list of all my favorite things from a given year on GitHub in my “Captain’s Log.”
Alrighty! Tells us what Holloway is? How did you come up with this idea? What problems can you solve with it?
At Holloway, we publish book-length practical Guides on modern work in order to improve our collective ability to address our greatest challenges. We believe knowledge is power, and the way to liberate the modern worker is by giving them the tools to take ownership of their careers and solve meaningful problems.
Not only do we publish practical knowledge, our goal is to make it discoverable where people look for it: in Google search. Today, if someone publishes a NYT bestseller on any practical subject, people can’t find the content of that book unless they know the exact title and buy it on Amazon. We believe there’s a better path.
Before I started Holloway, I co-founded a company called Mattermark. We were fascinated by the idea that Google was only good at answering some questions. Everyone knows it’s easy to type in, “What’s the capital of Poland?” into Google and get the answer. But it’s much harder to get the answer to a question like, “How do I start a business?” At Mattermark, we helped answer all sorts of questions that investors ask, like “How many e-commerce companies have been started in California this year, and can you show me a list of all of them?”
When I left Mattermark, I thought I’d leverage all of my relationships with investors and start a new venture capital fund called Earthrise Ventures (I own earthrise.vc). Brad Feld, our biggest investor at Mattermark, convinced me to start another company instead. So I came up with three criteria for my next company:
Oh, I also only had three months of money in my bank account, so I had to get moving.
I took these three criteria and spent a month or so researching different industries. The industry I looked the hardest at was clean water. I think this will be one of the biggest issues facing humans in the next ten years. In my research on clean water, I kept finding that the best information wasn’t showing up in Google search results. The best sources of knowledge were through informal networks of human beings who I had access to because of my network of investors. I remember thinking to myself, there have to be at least five or ten other people who want to work on the clean water wicket problem, but they aren’t finding the knowledge I am.
In that moment, I knew I wanted to devote the next ten years—at least—of my life to making knowledge that is available through informal, offline networks available to everyone online. I didn’t know how I’d solve it, but I knew I felt comfortable working on this problem for ten years and failing.
Where is your content coming from? Who is writing it? How do you think people will use it? How many people work at Holloway today?
Today, we either write all of our content in-house or contract with another author or writer for some piece of a Guide. My co-founder Josh Levy wrote most of our first Guide, The Holloway Guide to Equity Compensation with the help of Joe Wallin, a well-respected startup attorney.
People read and learn in so many different ways. We hope some Holloway users will read our Guides from the top to the bottom, but we don’t expect everyone to do this. We anticipate some readers will only want a specific question answered, want to read only a chapter, or some more granular part of the Guide. So we’re building that in.
As for our team, we’re six people.
The site is up but would you consider the company running yet?
We released our first Guide in August, and we incorporated the company in November of 2016, but I still don’t consider Holloway a business. We’re a company, but not a business. A company is the primary mechanism by which people form a group to solve a problem together. A business is a revenue producing company. That is to say, once we’re producing revenue, I’ll consider Holloway a business.
Based on the past year and with the influence we realize companies can have (e.g. Facebook) what do you hope Holloway will provide for people? How do feel this can change lives? Can you see it possibly used as a tool for harm? What would you do and are you ready for that?
2018 felt, to me, like the year that the world felt betrayed by the hope it placed in technology companies. The most misunderstood thing about all of this, though, is that the system that produced Facebook is basically the same system that created the oil companies we have today. Large corporations, especially public corporations, are governed by a set of laws and rules that force them to create value for shareholders over anyone else—this is called shareholder primacy. Shareholder primacy is a bug in the source code of the modern corporation that, until fixed, will continue to produce companies that betray the interests of consumers while favoring the interests of shareholders.
At Holloway, we’ll publish book-length practical Guides on modern work in order to improve our collective ability to address our greatest challenges. Some of the knowledge we publish will address this issue head-on.
The biggest risk I see for Holloway is that we’ll publish knowledge that enables people to work together much more effectively, and some group of people who want to work together to achieve a sinister goal become more effective. I could be wrong, but I think this may be unavoidable. We can’t control what motivates people, but we can do our best to inspire people to do good and share the knowledge about how others have done that most effectively.
How can people reach you if they are interested in learning more about what your building, or investing or being a writer?
Thank you Andy! I'll follow up with you later this year to see where 2019 has taken you. OR rather, where you've taken it.
Summer Wilson - Creative Director and Photographer of Battle Cry
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