Katelin Holloway Of 776 Advises Youths To Follow Curiosity And Ditch Standardization

Through the first week of November 2022, the Web Summit held in Lisbon, Portugal, brought together more than 70,000 people from across the globe. Perspectives on the opportunities and challenges facing business, innovation and government were discussed.

Beyond speaking engagements, the Web Summit featured pitch competitions and afterparties, including one with David Guetta and Armin Van Buren.

Benzinga attended and spoke with Katelin Holloway, a founding partner of Seven Seven Six. Here’s the conversation that transpired.

The following text was edited for clarity and concision.

Q: Hi there, nice to meet you. Care to start off with an introduction?

Holloway: I forged my first work permit, actually. So, I've been working since I was 13 and had pretty much every job there is. The reason I talk about all that is because these different stages and transitions have provided me with a lot of perspectives.

What was your early career experience like?

My early career was about paying the bills. I worked in law enforcement and banks, as well as food and retail. I was a teacher, too, at one point.

How did the teacher thing happen? That's quite the pivot.

My dream was to come to San Francisco and be a designer.

However, the economy crashed and I went back home and became a substitute teacher. Given a teaching crisis, I stepped up and became a fully-credentialed teacher.

What was it like teaching? Was your experience positive?

It was the most difficult job I ever had. There is an incredible amount of responsibility with it. The young kids really destroyed me because you’re so responsible for their basic foundations. After moving up to high school where those basic foundations are set, the pressure eased.

After teaching, I ended up moving to San Francisco and worked all over the place to pay rent. I worked in hedge funds and advertising. Advertising was a job that I hated, though.

What made advertising so bad? Never took it as a terrible career.

It was the culture. I was not putting goodness into the world, I did not like the product and the people around me were not kind. Later, I learned that’s what we called values misalignment.

I ended up leaving that job and went into a bit of a crisis. That was a pivotal moment. Up to that point, I was trying to pay the bills, as well as follow the title and money.

So, what did you do after leaving this job? Did you reassess your life?

I basically took a list of things I didn't like and looked for the opposite or inverse. I sought a place where I felt the people I worked with would care about me, that we are putting goodness into the world, and, most importantly, a place where I can learn continuously.

That resulted in me taking a pay and title cut. I moved to Pixar where I started as an executive assistant. That is one of the best positions to be in to build relationships with senior executives and develop insights into how that industry worked. That turned out to be a good decision.

Why were you so satisfied with that decision to join Pixar?

I learned every day and got to work on different films, teams and departments. I think that one of the reasons it was so impactful for me was that I joined the studio before the acquisition by Walt Disney Co DIS. I was present as the studio was articulating its culture. This was the first time I was actually exposed to institutional or intentional culture building.

You start thinking about where the bathrooms are, among other things of that nature.

Anyways, they were so supportive of my development and really cared about giving me the tools to be successful no matter what my role was. I moved around a lot and, before I left, I was where I wanted to be, embedded in the story team, working with the talent to bring stories to life.

Why would you leave a role that you were so passionate about?

I got a book deal to go write a tween novella. I threw caution to the wind and quit my job, despite having the best seat in the house and incredibly deep and important relationships with mentors like Edwin Catmull, who wrote the book Creativity, Inc.

I got writer's block, though, and went back to work in tech so that I could pay rent and unblock.

Oh, that’s interesting. What did the technology role entail?

I was more or less an executive assistant. A dear friend who had worked at Disney and was a children's book author introduced me to her boyfriend who had just raised a Series B. This was at the birth of Web2. She said: “Katelin, you've had every job on Earth, and you’re a seasoned operator. Come and share some of that Pixar fairy dust.”

And so, I worked 10 hats as we built the company. I gave myself the title Director of Creative Solutions or something. And a few months into the gig, I was in a board meeting and realized that I was the human resources lady. It sucked.

Oh, that's an interesting turn. Why did human resources suck to you?

I cared a lot about building a culture and developing our people. I care a lot about how people showed up in our product and how their fingerprints impacted the way our products were being built. However, I hated human resources because of the tactics.

I convinced my boss that we should stop calling it human resources. Instead, we were going to call it people culture. I wound up being the very first person in Silicon Valley where my title had the word culture in it.

What did you do differently under that new title?

We outsourced or figured out how to do things more effectively. I did that for about four years and I became one of the godmothers of taking human resources out of the back room and bringing it into the boardroom. I was at every board meeting and they supported me.

Then, I got into the speaking circuit and started building something called HR Open Source. It was all of the basic practices. We thought that if we were going to start this revolution, then we should be sharing our tool kit.

Were those the only things you were working on at the time, though?

I call that the beginning of my investing career, too, although I didn't recognize it at the time. In offering many young human resources tech companies product input, I wound up on a bunch of cap tables without investing a single dollar. I started seeing financial gains from that personally. That was kind of fun, but I loved spending time with those founders because they were building the products that I needed.

I’m sure that was just an extension. You must have felt satisfaction from your people culture role?

I was an executive in people culture for well over a decade and led the way on new policies. A lot of them had to do with women and moms just because of my own lived experience. That said, a lot of things that I'm really proud of in the space around diversity, inclusion and belonging came from my last operating gig at Reddit where I met Alexis Ohanian.

See Also: What Is Venture Capital?

Tell me a little bit about what it was like at Reddit. What was your impact?

Alexis hired me as employee 75 to do the big turnaround. We were in the news for all the wrong reasons, and it was a really hard time for the company. They were spun out of Condé Nast, which had acquired them. It was a make or break it moment in the company's history.

At that point, the company was 10 years old and they had never had anyone in a leadership role running HR. They had someone on the back end crossing T's and dotting I's. They didn't have anyone that was really thoughtful about building their culture.

It was truly an opportunity of a lifetime and such a rewarding job. We built a phenomenal team and I led that company up to about 750 employees globally. And on the eve of the IPO, I felt like my work there was done.

Why did you feel that your work was done at Reddit?

My cup was full and I started out properly angel investing on the side and assisting founders. I felt like I could have a bigger impact.

If you think about diversity, equity and inclusion from day zero, does that change your output? Does that actually change the financial outcomes of the business? I had seen it firsthand over the last decades as a builder. Up to that point, every company that I touched became more successful because of our people and the way we designed our culture.

Long story short, that's how I decided I wanted to do investing, and that's what I'm doing now with Alexis at Seven Seven Six.

What’s your advice for youth who may be in school or in their early career?

My advice is to follow your curiosity. With every twist and turn in my career, I followed curiosity. I wanted to know more because I had burning questions. I would go to bed at night thinking about things for too long and my brain would not stop racing. I’d start pulling threads and would wind up in a room filled with a ball of yarn that I didn't know I was interested in.

What are you focused on in your current role at Seven Seven Six?

We're a startup ourselves. We're two years old. I am focused heavily on the operations of the firm. So we just doubled our team size. I am very focused on our culture and the development of our people. I'm investing, actively, and supporting our existing portfolio companies.

Are you doing things differently in this tougher market environment?

I was taught very much, culturally, in my household to do a lot with very little. And so I am very unfazed by what's happening in the market because I always look ahead. We've always been intentional, thoughtful, disciplined and pragmatic in our investing.

Can you elaborate on how you’re supporting founders right now?

It just requires a lot more hands-on strategic attention. For instance, we’re making more pointed introductions and helping reverse engineer. You can’t parade around as if you’re in a suit made out of money, too. Sure, there was money to fix you, before. Things have changed.

In terms of the business model, how do you work differently from other VCs?

I actually don't know that much about what other VC firms do because I've not been in the industry. Nor was I tracking. That’s similar to how I didn't have any background in human resources before getting into human resources.

I actually think that there's a competitive advantage in not knowing the system and rules. Then, you're really building from the first principles. I think there’s a good balance between Alexis and I as partners in the firm. He's been doing this for a long time, and I can pick at things.

For instance, why are talent partners sitting in the back of companies? I think they should be front and center. We should be creating a journey that looks a lot different than anything I've experienced on the operator side.

In what ways are you rewriting the script for VCs?

Financial incentives and alignments. Why shouldn’t you give everyone carry? It’s just one of those things. I’ll do my research and come up with harebrained ideas.

When you’re looking into the future, what do you see in terms of the market environment and how do you position yourself to take advantage of any new opportunities?

I'm really excited about this particular contraction because it's going to weed out the people that were in it for the cash grab. Everything became a fad or trend which I think is healthy in general to have more awareness around blockchain technologies and the things yet to be innovated.

I'm excited about the contraction because I like to do more with less. Constraint, coupled with a healthy dose of creativity, can go a long way. I think that we will actually see more innovation.

Why should we expect to see more innovation during this downturn?

Pixar taught me this. When I joined the story team, they asked me to draw a dinosaur. So, I'm sitting there and trying to think, what's the coolest dinosaur? Then, they said: “Okay, how about you draw a robot dinosaur with a tail coming out of its forehead?” I was actually able to create something because they gave me constraints. That's the whole rule of creativity. When you have too much open space, it's overwhelming. I think we're going to see that in Web3.

Is regulation something you get excited about, given that?

With rules in place, then you can challenge and push the constraints.

Does this market feel like the tech and telecom boom and bust of the early 2000s? Also, do you get excited when people dismiss the innovation ongoing as nonsense?

There are a lot of similarities, yes. Also, I love it when people are distracted by the nonsense because I can make the investment or talk with those founders and learn, early.

What’s your approach with founders? Are you actively seeking investment opportunities or do they come to you?

We're super open. So I am of a school of thought similar to hiring. We do everything in the open. So, we open resources the way we're building things and operating.

Many things feel broken, traditionally. Most VCs don’t even post their open roles. So, how does anyone break into the world of venture if they don’t know that a role exists?

I think that we take a lot more pitches because we are open with our deal sourcing. We don't go in to have them prove themselves. Unconventionally, we go in to learn.

How do you evolve with the times, given all this disruption? The way our education system works is changing. Cultures in the workplace are changing.

I don't talk about college the way my parents talk to me about college. I want my kids to love learning and not chase a college logo or standardized path. There is a ton of value in lived experiences, too, and our society is evolving to a place where education is now distributed. Though we’re more agile and move quicker today, I feel a bigger shift coming.

More from the Web Summit: Crypto A 'Bottoms-up Movement' That's Too Big To Kill, Says Web3 Innovator Edge & Node's Tegan Kline

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