Finding Founders Andy Sparks of Holloway

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. 

Most of the individuals I photograph and laugh with are unlike anyone out there. YES, they can painfully exemplify nerdy or spectrum stereotypes.  But we’ve all seen the Instagram quotes.  You don’t change the world doing whatever every one else has done.  And therefore, those who change it must likely be different or a little crazy.

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.

I spent a few hours photographing Andy in his office across from AT&T park and hours chatting excitedly about what’s to come, best meals we’ve had and what to do around the city.  My first Founder of the year, Andy Sparks.

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:

• Ignoring and numbing discomfort and frustration is one of the most toxic behaviors to an organization. If a group of people can’t have productive and safe conversations about their disagreements or discomfort, that group of people will never achieve their goals.
  
• The difference between saying, “hire slow” and actually taking the time necessary to make the right hires is like watching a montage of an LA to London flight and actually sitting on the plane the whole time. The people you hire onto your team in the early days must share your values and have a reason to work at your company beyond money or a convenient commute.
  
• Teams need their leaders to set objectives and provide context on what’s important. If leaders don’t set objectives and trust their people, teams lose focus (or focus on the wrong things) and organizations quickly become dysfunctional.
  

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:

• First, I thought about all of the wicked problems the world is facing today like climate change. I want to be able to sit down with my grandkids and tell them I didn’t sit on the sidelines. I want to be able to say I did my best to work on the hard stuff, even if I don’t succeed.
• Second, I wanted to find something I could devote myself to for ten years or more. When you think past a decade, it makes it easy to rule out a lot.
• Third, I wanted to start a for-profit business, because I think revenue is a proof you’re creating value. There are some logical cracks in this argument, but I think it’s sound for the most part.

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.

You’re the first person writing a book for it.  Tell us about it.

Actually, Josh Levy was our first author. The Holloway Guide to Raising Venture Capital will be our second title. Our Guide to Equity Compensation is about thirty pages if you print it out, but our draft of our Guide to Raising Venture Capital is more than 150 pages, so it’s a whole new beast.

This is the first time I’ve written anything longer than a blog post in my career. I write about 100 days a year in order to think through problems, though. Even with all this practice, writing 100+ pages was a huge challenge. Josh was immensely helpful in pushing me to think through the structure of the Guide. Getting the table of contents right was the hardest part. Once I knew what I wanted to write about, there were days it just poured out of me. The funny thing about writing about something you have practical experience with is that you don’t know how much you know until you see all of it sitting on a screen, page after page, in front of you.

Writing on this specific subject has been a lot of fun, too. I moved to San Francisco almost seven years ago. I didn’t know anything about startups or raising venture capital. I learned everything I knew by reading Venture Deals, the Venture Hacks blog, Mark Suster, Fred Wilson, and by talking to a web of helpful people like my friend Danielle Morrill. $20M+ later in venture capital raised, I’ve seen the dark side of VC but also benefited tremendously. The main challenge I’ve had in writing this piece is in reflecting how VC can be toxic, but it can also be a great tool if used properly.

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?

People can email me at andy@holloway.com or follow me on Twitter at @SparksZilla.

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.