500px: CEO Andy Yang

What is 500px?

500px is the world’s premier photography platform. Our mission is twofold: 1) to build the web’s most passionate photography community and 2) to celebrate the artists using 500px. We have 12+ million registered users from every country on earth, and we also have licensing partnerships with certain creators who upload their best images. So essentially, it is an immensely powerful platform that enables photographers to share their work with the world.

How did you become the CEO of 500px?

I moved to Canada about six years ago. At first, I started as a venture capitalist and I covered 500px as an investment and I really admired the company, its founders, and the online community they created.

Since I had always been a fan of the company, when I found myself available for roles, I joined after their series A round in 2013. This was led by Andreessen-Horowitz, which is the best venture capital firm in the world. After Andreessen-Horowitz conducted a very impressive thesis on the company, I jumped aboard as the Chief Operating Officer. And then, after six months as COO, I made the switch to CEO. Now, as the CEO, I spend a lot of time learning and it’s been a very exciting journey!

What are the best and worst parts of being CEO?

One of the best parts is the constant learning — I get to learn new things and new situations every single day. As the CEO, there’s a lot of freedom, a lot of autonomy, and a lot of impact, and I get the opportunity to recruit, work, and train with the best team that I personally curated. It’s an awesome feeling to take a step back and see an amazing company and a culture that you built.

But, this is part and parcel with some of the tougher things. For one, since there’s something new every single day, there’s no set cadence to the day. So that unpredictability is definitely taxing on the body, mind, and soul, if you will. I also have to travel a lot, which can be very challenging as I have two young kids at home and it’s hard to be away from them.

Another negative factor is that there is a lot of pressure. Being funded by a Silicon Valley-based venture capital firm comes with very high expectations. The pace is extremely fast and so you have to be mentally and physically prepared for the rigours of the job. And, in terms of matching the glamorous portrayal of being a CEO — it begins and ends with you.

Someone once told me that “you're the emotional battery for the team.” And so that means that you have to be on at all times, and you can't have a lull in energy because people are going to notice that. So you have to bring your A-game every single hour, every single minute, of every single day.

With that ownership means that you are definitely going to have to roll up your sleeves. There are days when I wash the dishes, clean up the bathroom, and then there are days where I’ll be networking with some very powerful people. So yeah, it really runs the gamut.

Do you ever set boundaries to communication, or are you always “on” and responsive to to whatever emergency there is?

It really depends on your leadership style. For me, as a person of faith, I subscribe to certain leadership. Within the team, I make myself available at all times and if I’m busy, I tell them “I'll get back to you as soon as possible.” Or sometimes if they ping me on Slack, I'll just say “I'm with my kids, I'll get back to you after I put them down for bedtime.”

So there definitely are boundaries that you set, but at the same time as a leader, I want to serve my team. And how I can best serve them is to remove roadblocks, answer questions, and provide direction. And so sometimes those questions will come all throughout the day and all throughout the night. So yes, there's definitely an always “on” type of mentality that we have at 500px. But at the same time there are boundaries that each person can set. So really it depends your personal judgment.

What is your typical week like?

It starts from Sunday. On Sunday night I’ll plan out what I want to accomplish for the week, analyze what we did last week, and see if there are any metrics from our executive dashboard to review. For those, I’ll write up any kind of pertinent questions that I want my direct reports to answer and I’ll come up with strategies to improve certain metrics.

On Monday, it's a lot of individual team meetings so I hopscotch around the different teams and staff meetings. On Tuesday, we have an executive staff meeting with our senior leadership team and I do check-ins with one of my board members.

On Wednesdays and Thursdays, we try to have no meetings, because we subscribe to the theory of deep work. And that requires large uninterrupted blocks of time to do deep work. So if it's coding, financial spreadsheets, or PowerPoint presentations, we try to reserve as much open-ended time as possible so our employees can get into the flow and really just start to create. For me personally, I take this time to have external meetings with potential clients.

Then on Fridays we have our one-on-ones. These are obviously just one-on-one meetings with each of my direct reports, where we'll talk about business issues, personal issues, and generally connect on a weekly basis. And from 2-4PM, I reserve time for office hours, where I do events or podcasts like this to meet with people in the industry! And then we cap off the week with a “power hour” at 4PM — our own internal happy hour event.

So from a team perspective, that's the normal week. However, it gets thrown off through travel, conferences, board meetings, and just the general cadence of life. So there is a lot of unpredictability.

Is the company culture mostly set by you, or was it already in place from the founders?

It's a mix of both. The founders always believed in having a serene working environment where people would be very deeply entrenched in the act of creation, whether it's creating something with code or in designing in Illustrator, the founders wanted this essence of serenity. And I was a really big fan of that environment! Since we do have an open floor plan, it is essential for people to be able to concentrate and not get interrupted every 10-15 minutes with a different question.

In terms of the makers schedule, it was based off a blog post by Paul Graham, the founder of Y Combinator. He talked about the maker's schedule versus the manager's schedule. In the manager's schedule, they're going to have meetings and you're at the whim of their schedules, so they'll schedule whenever there's an open block. But if that’s scheduled in the middle of a three-hour open window for you, the manager is cutting up your time into three one-hour chunks. That is very disruptive. And there's been multiple studies on context switching and multitasking for us to know just how destructive that is to flow and the ability to create, especially for developers.

Developers will have it all mapped out in their head of the different systems and processes, and then it'll take them 20-30 minutes to get in that flow. So if there’s a disruptive meeting in the middle, now there's only 30 minutes left in their one hour block to work. There’s only a limited amount of code you can write before you have to stop, go to the meeting, come back, and spend another 30 minutes to get into your original flow.

So that is very disruptive, and I felt coming from finance and consulting, I really appreciated having 3-4 hour blocks to work on financial models or presentations, where I could just put on headphones and jam. That's why I wanted to incorporate that ethos and behaviour into 500px. So yeah, that's definitely has been an influence of mine on the culture.

Yeah, developers can get very grumpy if you interrupt them in the middle of their work.

Yeah, exactly. And especially if you're tapping them on the shoulder or sending a Slack message. It's just very disruptive.

You came from a background of consulting and finance. How did you know that you wanted to work at a tech company — specifically a company in photography and in Toronto?

Toronto is great. I'll start with technology. I went to school at Berkeley and graduated in 2000, so tech was basically the only industry my friends were going into. So I became really interested in the industry! I've always been somewhat of the nerd, in terms of using gadgets and how things work, so I really loved technology from a personal use case perspective.

And then it unfolded into different roles within technology and I really started to understand like what I liked. I liked building communities, I liked working online, I liked e-commerce. And so a lot of these passions of mine all culminated at a place like 500px.

Six years ago, when my wife got a job at Ryerson University, we moved the whole family over from the Bay Area. So that's what brought us to Toronto, and then I discovered 500px and joined them. What attracted me is definitely the opportunity to work at a global scale, the beautiful designs, and the great user experience attracted me.

The photos are stunning as well — I'm a very visual worker and I love putting together stories through our photos and through photography. And so, using other people's photography to tell a story that I want to tell is something that definitely appealed to what I'm passionate about. Since then, I've been trying to learn and pick up photography; I've always been an enthusiast, and now I would say I'm getting a lot better. It's definitely changed how I see and perceive the world.

Let's break that journey down. You started at Berkeley and studied civil engineering. Why? How did your undergrad experience impact your life today?

These are lots of great questions! So, in high school there was a presentation of the different types of engineering and all my friends were interested in computers. They all went the electrical engineering or computer science route. And while I liked CS and computer science, I'm more of a tactile learner.

I was always interested in working with my hands, so civil engineering was the best fit for me. It’s the oldest type of engineering. I was just attracted to the aspect of building things and building roads and bridges and transportation. So that was this huge avenue for me. And there was a little bit of a rebellious streak as well — I didn't want to go into the crowd of my friends and study electrical engineering and computer science.

I was like, I'll just be a little bit different and go take civil engineering. It was also compounded by the fact that I got into Berkeley, it was the number one single engineering program in the world. So I was like, if I can learn and work from the best, that'd be great. And in terms of professional experience, my answer was construction management.

I learned a lot of project management; how to organize and marshal resources, how to deal with setbacks, scheduling, etc. It has just been this foundational training of getting things done and accomplishing a project.

So I would say my expertise is just getting things done and marshalling and scheduling resources to get that particular job, or any job, done. And that really set me on the kind of foundational points of some of the things I learned at Berkeley.

After Berkeley, I saw that you worked in consulting for a few years. Why did you choose consulting?

Coming out of a civil engineering program, I was agnostic to what I did in terms of technology. And so, consulting was a way to be an undeclared major, if you will. I got to see a lot of different projects. I was deployed to the financial services industry and FinTech is now huge. So I got this really great foundation for technology and finance and started to learn a lot from the different projects.

Consulting it teaches you a lot of the foundational skills of how to tell a story, how to get data, how to interview clients. Then on some of the larger implementation projects, I got the foundation for tech; I racked servers and I was a junior Unix system admin.

I got to learn a lot of basic tech skills as well. A lot of people these days have never seen a server or they just use AWS, but I personally worked in a data centre for about a year. So I know what people talking about and how it works — I running Cat 5 cables all over the place. It just gives me a bit more confidence to say, look, I've done those things in my life.

After consulting, you worked in venture capital for a few years. What were some of your insights?

I actually went to business school before then. Post-MBA, I was an investment banker and I learned about the financial basics; how to use Excel from a power user perspective and how to model just about anything. That really set me up to be a venture capitalist.

Transitioning from the sell side to the buy side, I was grateful to have the the financial understanding of how capital markets work. Moving more to the private capital side, I really understood how to evaluate a company, how my partners viewed specific investments, how to perform due diligence, and also how to be scrappy! You can only be a VC for so long before you get inspired by the other entrepreneurs you're meeting.

I also learned very early on in my VC career on how to listen. I knew how to discern what people were telling you and whether they were hiding something, or whether there was something there of substance.

And so, I also learned about entrepreneurship and how much I valued it and how much I valued the freedom and ability to create your own destiny, if you will. One of the key things I did early on was, right when AngelList was just starting as a platform, I would personally start screening 15-20 companies in a concentrated day. I called them super Fridays, only for me, and I would scour AngelList and book 30 minute meetings with each of the companies that seemed interesting and within our frame of investment. I’d start running through these calls and evaluating and sourcing these deals, and that honed my eye on what to look for.

When I transitioned to the accelerator, that was just more amplified. We would have these cohorts where we’d evaluate 300-400 companies at a time and then schedule them in for what we call super Saturdays or super Mondays. And then we would schedule these 20-30 minute interviews where they would pitch to our investment committee in-person, and we’d score them on a numeric scale and run them through.

So that's on the sourcing side. But then in running the accelerator, I had good mentors and we trained these companies in batches of five every six months. And so we really work with the entrepreneurs — we help refine their pitchdecks, their business model, their products, and really be in the trenches with them. You truly learn so much about the entrepreneurs and I've worked with some of the best.

So that’s been a key learning of mine — how to be an entrepreneur and how to make things succeed.

Can you expand on the listening piece? How did you know when someone was embellishing facts or if they were truly a diamond in the rough?

Yeah, it’s very nuanced. It’s almost like a lie detector — they get your baseline and then they ask you questions like what's your name, how old are you, etc.

That’s what I would do to get somebody's baseline. If they're just naturally super pumped and super positive about everything, that's their baseline. And if they’re not as pumped over a certain metric or vision, that tells you that they're unsure on this.

On the other side, if they’re generally a neutral or pessimistic person, and they get super excited about something, then you know that there's something substance there. And it makes you want to draw in and dig in more. But really, it's about getting that baseline and understand what the deviation is on certain pieces of information that they're telling you.

The other piece of it is your own due diligence. Either you use their product or, if they have a demo, go through the demo. It’s very surprising that so many VCs, at least back in the day, didn't do that before meeting with an entrepreneur. And that was insane to me. I would hopefully have the questions ready, like "hey I used your product, I have questions or feedback on these specific points” and that's what impressed entrepreneurs. They thought, oh wow, this person took the time to run through the product or go through all these extra steps.”

That’s essentially a lot of the basics. Then you could ask them more intimate questions about specific decisions they made in the product or in the business.

So now that you've come from both sides, investing and operating, which one do you prefer?

That's a really good question. I would say I'd definitely prefer operating. As a VC, you're always on the sideline. You can still help the company by making an introduction and ultimately funding the company, but there's nothing like operating because that's the true test of whether you can make the company successful or not. In terms of just the skill set of investing versus operating, for me personally I'd prefer operating even though it is much more stressful.

Would you say that operating is more work?

Yeah, it's definitely more work. It's more encompassing. Although VCs do work hard, I would say for an operator, that's how you build something of true value. You're building a company that employs people to create a product that millions of other people use around the world. And obviously, VCs enable that, they build their amazing firms, and, create monetary value for their LPs.

Ultimately it really depends on the people listening on the podcast. It depends on what type of skill set you want to build. VC is a great way to help entrepreneurs. It's definitely necessary and very needed. But at the same time, there's hundreds if not thousands of startups in Toronto that need smart people who can create products and opportunities for others.

Speaking of Toronto, do you think Canadians entrepreneurs should move to SF or stay in Toronto if they want to work in tech?

Tons of people ask me "should I move to SF?"

My answer is if you want, then do it. Because there is no substitute for the Valley. There's no place on earth that moves at the speed, thinks as big, or has as much capital as Silicon Valley. There's no replication for that. For the people who want to experience that, and it's a bucket list item for them, nothing I say is gonna discourage that.

What I do say is, if you're just looking for that type of experience, then there are companies and entrepreneurs that are just as good, if not potentially even better, that are in Toronto and that have started companies in Toronto and Ontario.

If you're just looking for that experience, you don't have to go to the Valley. But if you're seeking that quote unquote “experience” and it’s just something you have to do in your life, then nothing I do or say is gonna change that. So you should go.

Each person has to make that own decision. It’s kind of like if you're interested in investment banking — do you go somewhere else other than New York? It’s the same analogy, even though with investment banking you can do it in more places, but New York's the center of finance, Paris’s the center of fashion, there's numerous analogies and there's industries that you just can't replicate what a geography is known for.

And I feel like students should be more aware that it's not all stars and fireworks. There's like a lot of struggle. Some people find it worth it and some people don't find it worth it. It's just what they personally want.

For some people, nothing you say is going to discourage their perception of that. So they have to live their experience and make their own conclusion. I've known people that have moved there and stayed ever since, because they love it and put down roots.

I offer the alternative of, just do it and if it works out, great. If it doesn't, then come back because there's an ecosystem that's grown, I would say, 100 fold since I moved to Toronto in 2010. There’s now different types of companies, the capital — just the momentum that we have as a ecosystem and the branding of Toronto is great. There's a lot of exciting things happening and there's this next generation of entrepreneurs that are being home grown, and staying, and want to build amazing companies here.

To wrap up: is there any popular entrepreneurial advice that you strongly disagree with?

I hate to sound so politically correct but: take everything with a grain of salt. There's no playbook for entrepreneurship. You just do what it takes. There's not going to be this blog post or this advice that you're going to hear that’s going to be super applicable or amazing. Use your own judgment and then get your own experience.

When you read the timbits of advice, use your judgment and distill it to if it applies to your particular situation. You know the phrase “move fast and break things”? That works for Facebook, but it might not work for a financial services tech startup. You can't break people's wallets or money.

There's certain things that you have to make your own. That's what the prevailing advice is like — just use your own judgment to make those calls.

Last question: what advice would you give to young graduates today who are just entering the workforce?

So I know I'm going to contradict myself from my earlier answer. But, the thing that's been personally successful for me is, and I learned early on in my career, is to just be a lot like Johnny or Jenny on the spot. If there's an opportunity that other people either don't want or it's the grunt work, just raise your hand and do it.

For me, that's been what’s added the most value — to take these opportunities and then learn as much as you can and be propelled for further opportunities. A lot of these days, I find people are trying to shortcut their way or get through things as fast as possible without putting in the work and learning the rudimentary skills that it takes to succeed.

For me, it’s important to have a great attitude, a willingness to work really hard, don’t make excuses, don’t blame, and have a bias towards action. The best advice I can give is to just get your hands in there, get dirty, and don't be afraid of some of the grunt work.