Perspectives on the art of work: a conversation with Arjun Dev Arora

In this series, I share my journey to connect with - and learn from - people who have succeeded at the intersection of team performance, personal development, and innovation. 

In this installment, I talk with Arjun Dev Arora.

Arjun is a Partner at 500 Startups. He was Founder and CEO of ReTargeter, and more recently co-founder of Immediately. Arjun got his operating start in business development and strategy at Yahoo! Real Estate. Today, in addition to his work with 500 Startups, he is also an advisor and investor to various startups in Silicon Valley: you may recognize a few, they include names like AngelList and Change.org.

He’s passionate about leadership, growth, philosophy and startups. His motto: Pay it forward.

He paid it forward to me talking about some of the subjects I’m passionate about - teamwork, vision, productivity, and what I call “the art of work.” His perspective resonates. If you know our ResultMaps mission and our community, you’d think I scripted his answers. I hope you enjoy.

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Scott: I've got team questions. I've got personal focus and productivity questions. Lots of questions... I’ll start with this one. Your personal experiences, especially in a situation like what I'm imagining at 500 Startups, is probably similar to when I was at GrowthX or now at ResultMaps in that there is a lot going on. How do you prioritize your time in a day? Do you have a methodology you like or a routine you go through?

Arjun: Over the last, I'd say, 10 years, I've developed a pretty consistent schedule that I try and maintain, at least when I'm here in San Francisco, it’s come through a lot of trial and error.

I know everyone says don't look at your emails first thing in the morning; I do it anyway. It works well for me. But I think it's come through practice and not getting triggered by messages. It's probably just from experience of dealing with a lot of crazy stuff. But I wake up in the morning, and I look at my email first thing.

Then I usually work for an hour from home in the morning, and then I usually try to walk to the office. I typically take one to two calls while I do that. That gives me an opportunity to get some fresh air, wake up, get a cup of coffee on the way, and have some conversations. Typically, it's just time where I'll chat with founders, try and be helpful with portfolio companies, meet with people who are new folks who just kind of want to get in touch, or be helpful to the ecosystem.

I get into the office typically somewhere between 8:30 and 9:15, and I'll work for a couple of hours. 

I go to the gym before lunch, and that's an hour in my day. That’s something I’ve been pretty religious about for the last seven or eight years. It's a good way to kind of reset, do some thinking, do some strategy kind of work, think about priorities for the day, think about issues. I always get those kind of insights in the shower, on the run, or whatever it is, so that's valuable. Then I'll either have a lunch meeting or typically eat at my desk. And, usually, my afternoon is filled with in-person meetings.

Then in the evening, I'll usually go out and try and connect with someone over a drink or over dinner, or both in some cases, just as an opportunity to build and maintain the network, which I think is so important, particularly in my role. And then, I'll either kind of take it easy or do some additional email from home, trying not to do more than three hours. So it's a pretty full schedule, and keeps me engaged and busy.

Scott: You said make sure you spend time on the ecosystem on the walk to work. Can you tell me a little bit more about that?

Arjun: It's basically working ... quick calls with portfolio companies, companies that I invested in or companies that I am advising, new founders who I haven't invested in that want to get to know me or vice versa. Or it's somebody who used to work for me in a previous gig who's trying to figure out what they're doing next, and they wanted to spend 20 minutes chatting about, "Hey, you know me. You've worked with me. I'm thinking about doing this (new endeavor). What do you think? Who are people that you know that might be open to chatting with me? What are the venture firms that are hot right now?" That sort of stuff, I think that's the situation on those kind of conversations.

Scott: I like the creative ways you make time to connect with others and offer your perspective. You said it took you years to develop a system that worked for you...and you do have this broad background with a few pivots along the way. Tell us a little about the journey that produced your perspective.

Arjun: Totally. I'll start from the beginning. I studied electrical engineering and computer science, at UC Berkeley, so a pretty technical background. I then took a bit of a sharp left turn and went into investment banking, but still focused on the tech space. I eventually spent a couple of years at Yahoo! and ended up running business development for Yahoo! Real Estate. At the time- 2007 to 2009 - it was the largest online real estate site in the US. It was a great opportunity in the early days of web 2.0, and a chance to help bring listings for real estate agents online. 

From there, I started my first company called ReTargeter in the online advertising space. We bootstrapped that, got it to tens of millions in revenue, and just under 50 people here in San Francisco. It was one of Inc.'s fastest growing companies in 2013, and I eventually sold that in 2015.

And then another short stint at a company called Immediately as a late kind of co-founder. That one ended up getting acquired.

About seven years ago, I started doing a lot of angel investing and advising. Today I’ve invested in or advised personally over 60 companies. Some of the more familiar ones: AngelList, Change.org, Branch Metrics, and others.

At 500 Startups, I now lead our efforts globally for fundraising and investor relations for the firm, as well as, of course, continuing to invest in great founders.

So that's the short story.

First and foremost, [what the best teams have] is a clear understanding of the values that are important to that team. Second is an understanding of the mission or the vision of what they're trying to accomplish.

Scott: With your background, I'm guessing you've been in a lot of different situations. And with the number of investments you have, you've probably seen teams in varied situations. What characteristics do you see consistent in the best teams?

Arjun: Absolutely. I think one, first and foremost, is a clear understanding of the values that are important to that team. Second is an understanding of the mission or the vision of what they're trying to accomplish. Basically, everything, foundationally and systemically, has to be correct before you can make any meaningful moves from there. So to put first-things-first: they have a clear sense of the mission or where they're headed and then a clear set of values: How are we going to operate together, and how are we going to operate separately?

[the best teams] have a clear sense of the mission or where they're headed and then a clear set of values: How are we going to operate together? How are we going to operate separately?

I think the best teams are very, very clear about those things.

From there, I think there's a communication infrastructure and architecture that needs to be deliberately crafted by the leader, in order to ensure that there's the right level of communication happening in and amongst the team. That can look like regular weekly check-ins. It can look like slack channels. It can look like updates after meetings. It can look like transparency into everybody's calendar. If you want to go really extreme, it's transparency into even kind of some level of personal calendar as well, just so people can kind of have a sense of what's going on. These are the things that I think are really important.

And then from there, I think just regular time spent together, getting to know people, getting to know the team, things that aren't necessarily purely work-related. Assuming the mission is clear, the values are clear, there's a communication infrastructure that lets everyone know what's going on, that goals are being hit. Then you just want to make sure that you build trust and you have just a real human connection in and amongst the team because that will allow you to get through some of the harder times, because if you're doing anything of note, you will have them.

Scott: Most definitely. Are you comfortable giving some examples of your favorite teams?

Arjun: Yeah. It's a great question. I guess I can speak from my personal experience. When I was at Yahoo! Real Estate, Steve Schultz, who was later the COO of Check, which got acquired by Intuit, was there, and he is who I learned a lot of my style of early team-building. He was just abundantly clear on how to document, and on what we were trying to accomplish. Everybody had three priorities. We communicated regularly on a weekly basis in a standing meeting, and we had fun together, and he trusted the team. And I think trusted the team to execute against the goals that he had given, and that was kind of my first example. I was relatively young at the time, and I was deeply appreciative and grateful for his example and leadership that he shared in setting up a good infrastructure for a small, tight-knit, intelligent, hard-working team. It was great.

Now I think in the external or kind of public sense, I think what Airbnb has done and how they've operated has been a really good example of execution that both gets the job done, and also creates an environment that people are excited to come to work to.

Scott: Any of your own companies that you feel the teams have really done well?

Arjun: The AngelList team is unique because they're pretty decentralized. They have a very clear set of values in how they operate, and they don't need to meet in the office every day. But they've figured a clear communication infrastructure and they have a six year vest on their employee stock, so they're building something for the long term. They're very respectful of everybody's personal time and space, as long as they're getting their work done. 

Another, younger kind of company that I think has done a good job is RapidAPI. They were in our 500 Startups seed program a couple years ago. They're a team between Israel and San Francisco, with a very young founder, and what I really appreciate about him is that he's incredibly open to learning and recognizes the importance of effective team-building. From day one, he has implemented a really tight communication infrastructure with his cross-border team, and been able to execute really well, so I've been impressed by the work he’s done.

Scott: This is great. You mentioned mission, values, communication. These are mission-critical topics in my world, and I want to dig into those a little bit. First, out of curiosity, do you feel the interplay is between those elements and a team's ability to innovate?

Arjun: One of the values that has to be really important if a team is looking to innovate is the actual trust in the team. If you have a team where ideas are judged as stupid or it's all the boss's opinion sort of thing, then innovation doesn't really happen. There has to be an openness to allow for new ideas, crazy ideas, and those ideas have to be not necessarily tied to the person from whom they're coming. If there's a structural impediment to that, it can be incredibly problematic.

One of the values that has to be really important if a team is looking to innovate is the actual trust in the team.

The other thing, from a structural perspective, is having space. If you're back to back all day in meetings and calls, conversations, getting pinged on email, phone, you don't have the space to kind of let innovation and inspiration kind of strike. That's problematic. 

And finally, really spending the time to understand your customers' needs. I think the best innovation comes from a deep, deep understanding of customers, whoever those happen to be. If you don't have that level of understanding, then even if it's a brilliant stroke of inspiration, then it's art and not innovation, because it doesn't solve a problem. 

Scott: Do you have any observations on what makes communication effective? 

Arjun: Ultimately, I think it's a focus on the truth with a capital T. If you are concise, consistent, and you're really focused on telling it as it is, not trying to sugarcoat it, especially internally with the team -- that sort of clarity is really critical in communication.

I really value - and this may be a personal thing - conciseness. There may be a better way to say this, but information density, high information density, is really important. There can be a lot of fluff in communication, and that ends up wasting people's time and taking away from the essence of the message.

Scott: Tell me a little bit about what motivates you personally. Do you see yourself as being on a mission?

Arjun: Yeah, I think for me there really is.

I think entrepreneurship, and what's happening with technology as a whole really, is an incredible opportunity. As cheesy as it sounds it's an opportunity to build a better world, and build a more equitable and fair world, to bring opportunity to a lot more folks.

I think particularly at 500 [500 Startups], given our global approach to things, that is even more true than elsewhere, but I think even then, the technology ecosystem, the entrepreneurship ethos that exists, particularly being at the seed stage or at the early stage of giving people that chance and that opportunity to build something great, believing in folks before others do, is certainly, I think, my mission.

Additionally I think creating organizations that are healthy, for lack of a better term, is another key part of what drives and motivates me -- especially being able to be involved at the early stages with companies as they're starting to get things going and are starting to really set their culture -- is an incredible opportunity.

Having the ability to influence somebody who may build the next Lyft, Airbnb, Stripe, and helping them think through issues around how to create a great workplace, create an effective team, reward and compensate employees in a way that's fair, to do the things that allow them to be proud of the work they do and build their own self-confidence and self-awareness. That's a phenomenal opportunity, and I don't take that lightly. 

Scott: You said "healthy." I like that term applied to teams and organizations. I'd love to know what that means to you in an organization, to build a healthy organization.

Arjun: A healthy organization is one in which people are respected. That is step one, and that means people inside and outside the organization. There's a clear set of values on how things operate. I think a lot of politics and pain in organizations comes from when people say one thing, but mean another, or things change and people don't get a heads-up, or things change and even the team doesn't know that things are changing. I think a strong awareness of what's happening is really important, and then a clear set of values and a focus, really, on helping people improve personally. And understanding that if people are growing personally and professionally -- that the organization will be growing personally and professionally. I think it can be simplified in just that, frankly.

A healthy organization is one in which people are respected. That is step one.

And then just making sure there's no things that are not healthy, like politics or lack of clarity or kind of weird backstabbing-type behavior, anything like that. But again, I think if there's transparency in clarity and values, those sort of things disappear. You shine the light on that, that stuff goes away pretty fast.

Scott: That is excellent. I have a question about getting out of politics -- one of our community members asked about it. Have you ever had to really get a team to improve, get them to be more open, coax them? It could be yours or someone else's you were mentoring, but any techniques you've seen that have been particularly effective?

Arjun: I think in the end it's spending really quality time with each of the individuals on the team and understanding their personal motivations -- it’s critical. Why are they doing this job? Is it just for a paycheck? Do they want to grow? Do they want to learn about the venture industry or ad tech? Do they want to build a career where they're going to succeed in sales, if they're a junior salesperson? Do they have a sick sibling at home who they need to take care of and that's important for them? Really understanding what the needs, wants, and desires of the individuals on the team are, and then aligning those with the goals of the organization as a whole, and the team as a whole, is critical.

I think the first thing a leader can do to turn around an organization is really understand each of the individuals on a very one-on-one basis. Then, with that understanding in mind, develop a clear mission and vision that is attainable with the team that's at hand. The next step is working with everyone to commit to getting to that vision, with an understanding of where they are and what they want, and doing that is a clear way to move things in the right direction.

I think the first thing a leader can do to turn around an organization is really understand each of the individuals on a very one-on-one basis.

Scott: This resonates with so much of the knowledge we are trying to amplify with ResultMaps - the aligning teams around values and personal and professional goals. People are going to think I scripted this. It’s great to hear your take on all of it.

Arjun: I've lived it. I've learned some lessons the hard way.

Scott: Thanks for talking with me today.

Arjun: You bet.