Interview with Anuj Abrol, Former Chief of Staff for Justin Kan

This article is part of a series revealing the stories of early employees from the most successful tech companies of the past few years. You’ll walk away having learned about what these individuals experienced, what they wish they knew, and the advice they’d give to others joining high-growth startups. Key takeaways are at the top and you can find the full interview below. 

This interview is with Anuj Abrol. Anuj grew up in the Midwest, worked at McKinsey after school, then became Chief of Staff to Justin Kan (co-founder of Twitch). During that time, Anuj worked on a number of initiatives related to Atrium, a law-tech startup Justin had started. Below is an edited version of a conversation he had with us here at Compound. 

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Key Takeaways

• On what Anuj learned from Justin Kan – “Justin taught me the importance of being able to tell narratives. Whether it was in board meetings, recruiting calls, all-hands, fundraising, or sales, Justin’s superpower was telling narratives. Great narratives are powerful - they attract people to join you on your journey. This turbocharged the company. It helped us acquire customers, talent, and funding in a significantly more efficient manner. This also allowed Justin to not be in the weeds as much. It free’d him to focus on the most important problems.”
• On focusing on a single value proposition – “One of the main reasons that Atrium struggled is we didn’t have a clear value proposition. We were trying to win on a variety of dimensions. We competed on ease of use, having the best-trained staff, having the quickest service, having the lowest prices, the best tech, etc. We learned that our customers – oftentimes early-stage startups – would go to great lengths to minimize their cost. We didn’t work because our margins were not healthy enough. I can never know for sure, but if we would have competed on cost with a “good enough” service, that might’ve worked for the early stage segment.”
• How Anuj learned about early-stage investing – “I had the fortune to invest $1-2M per year into startups on behalf of Justin. But in the beginning, I had no idea what I was doing. [...] Like any good former management consultant, to help answer the questions I created a research project for myself where I wrote guides on these topics. [...] I wrote them for my own understanding and those I was able to interview. We published them on the Atrium blog. A few examples were The Founder’s Guide to Markets and The Founder’s Guide to Understanding Investors. They helped me understand how to invest and they also helped founders navigate the fundraising process. ”
• How Silicon Valley rewards ambition – “Atrium was a massive swing. Unfortunately, it didn’t work out. It’s natural to be ashamed of failure. I felt it. But when Atrium shut down, there was a lot of love for Atrium, the team, and Justin himself. Seeing the support first-hand made me realize how much this ecosystem rewards trying something ambitious even if it ends up failing.”

Tell me about your background and how you started working for Justin Kan

I grew up in the Midwest just outside Flint, Michigan. I used to be a golf caddy and the people I would caddy for were local business leaders. They might own a car dealership, or a small OEM manufacturer, or one time I even caddied for the then CEO of Ford. These people were all I knew what “career success” looked like. But I couldn’t see myself doing that with my life. 

I didn’t find a calling until I got to college and learned about the world of startups. I worked at a couple and had two of my own. While they didn’t work out, I loved building and the hustle. After college I hustled to work at McKinsey to develop a business toolkit that I could apply later in my career. After 2 years at McKinsey, I knew I wanted to get back into startups. I was looking for a high-growth role or to work with a high-growth person. 

I had actually started a relationship with Justin Kan before he started Atrium. For a while in 2016 he was posting these startup tips on his Snapchat stories and I would comment on them. He would post stuff like, “If you’re looking for a co-founder, here’s what to look for.” Or, “Here are some resources on how to learn to code.” Back then, that stuff was super helpful to me. Sometimes he would post questions or advice and I would respond back. After a couple months, he liked what I had to say and gave me his email.

At the time, Justin had another Chief of Staff, Nick Cortes. Nick was also from McKinsey and so when they were looking for someone to hire, I was able to leverage my background. I emailed Justin a few times and he ghosted me. But on the fourth time I told him I was in San Francisco and a minute later he responded and asked if I wanted to come to his house. So I did and 6 months later I ended up joining him.

What was your first project working with Justin?

I was an employee of Justin Kan Enterprises. My mandate was basically to help Justin achieve his goals – that was the highest level description. 

The first project I worked on was to help Justin with his angel investing. I had the fortune to invest $1-2M per year into startups on behalf of Justin.

But in the beginning, I had no idea what I was doing. This was my first time ever investing in startups so being the good consultant I was, I developed a framework for investing. Justin had the deal flow solved – he could effectively get into any deal he wanted. But then there’s the question of picking startups. I had to figure out our strategy. What should we look for in these companies? How’s the game played? How do the top investors differentiate themselves? 

Like any good former management consultant, to help answer the questions I created a research project for myself where I wrote guides on these topics. I consumed every piece of VC content I could find - tweets, podcasts, books, blogs - you name it. I wrote them for my own understanding and those I was able to interview. We published them on the Atrium blog. A few examples were The Founder’s Guide to Markets and The Founder’s Guide to Understanding Investors. They helped me understand how to invest and they also helped founders navigate the fundraising process. 

What was Atrium most focused on as a company?

Atrium focused on different things in different company stages – I was there for two years and there were three different things we focused on.

When I was interviewing and right when I joined, there were fewer than 10 people. The company was just focused on the operational basics. Justin had raised money on an idea, a pitch deck, and his co-founders, and they needed people to start building things. 

During the first half of my tenure, the company was then focused on growth. It was about securing clients and seeing if we had a value proposition that people wanted to engage with. 

And then during the second half of my time there, we knew people would adopt the service, but we hadn’t figured out the business model yet. A lot of focus was on contribution margin and making sure that we weren’t just selling $1 for 80 cents. It was around the time that we brought on Joanna (who was early at Facebook) as COO to help us with this. 

Justin used the term “service-market fit” a lot internally. We knew that people needed legal services and that we could provide a better experience, we just didn’t know if we could do it with positive unit economics. 

What were you most proud of to have worked on while at Atrium?

The Chief of Staff is there to execute on the needs of the person that you’re working with, without an agenda of your own. The person you are helping needs to trust you fully. I felt like I did that. I took pride in it. One of the projects that I did was quarterback the Series B fundraise from start to completion. It included everything from crafting the narrative, to identifying who would be the best partners for us, to all of the little stuff like making sure demos were ready and that executives had answers prepared for questions. 

There were two things I was proud of about this fundraise. First, we did it quickly, making sure not to distract the team. Raising money is this funny thing that while it is an opportunity for external validation, it’s a distraction for the team. We wanted to minimize that distraction by doing the raise from start to wire as in as minimal time as possible. Second, Justin had this saying, “create a market for yourself,” which basically meant that if you had more than one offer available, you had more control over your own destiny than you thought. 

There is a quote Sun Tzu is known for, “every battle is won or lost before it is ever fought.” Some may view it as extreme, but that’s how I viewed my role. At that stage, we needed more than a narrative to raise. Meticulous preparation from the team catalyzed us to create a market for our term sheet. 

What did you learn most from working closely with Justin Kan?

The most important thing I learned was just that if you have a personal brand, it can be a hack when starting a startup. At the end of the day product-market fit matters most, but having a personal brand makes all of the other important stuff (hiring, fundraising, finding initial customers) a lot easier. 

Justin also had founder-market fit with Atrium. He was a serial founder and investor, and had used startup legal services many times. He was building something for himself. And because he knew other founders and investors, it was a lot easier for him to get funding and to find customers at the beginning. 

Justin taught me the importance of being able to tell narratives. Whether it was in board meetings, recruiting calls, all-hands, fundraising, or sales, Justin’s superpower was telling narratives. Great narratives are powerful - they attract people to join you on your journey. This turbocharged the company. It helped us acquire customers, talent, and funding in a significantly more efficient manner. This also allowed Justin to not be in the weeds as much. It free’d him to focus on the most important problems.

Finally, working with Justin and Atrium taught me that Silicon Valley rewards ambition. Atrium was a massive swing. Unfortunately, it didn’t work out. It’s natural to be ashamed of failure. I felt it. But when Atrium shut down, there was a lot of love for Atrium, the team, and Justin himself. Seeing the support first-hand made me realize how much this ecosystem rewards trying something ambitious even if it ends up failing. 

While I learned a lot from him, I also learned that he’s a human just like the rest of us. He’s very smart of course. But coming from the midwest, it was very easy for me to think of notable founders and VCs as fictional characters in startup lore. In reality, they’re everyday people just like you and I. 

What advice would you give to someone starting as a Chief of Staff?

As a consultant you would gather all of your thoughts, then make a deck, then present the recommendation. And the first couple of times that’s what I did. But at a startup you just have to act – if you see something, you go do it. 

One example of this was around meeting hygiene. Some of our meetings had a clear goal, clear agenda, and everyone was paying attention. But then other meetings were unstructured and people were wondering why they were even there. Sometimes a great idea would pop out of them, but they would be better suited towards an off-site or a walking meeting. As Chief of Staff, I had the influence to clean this up. Get the right people in the room, make sure that each meeting was well-run, and have clear action items after it. Taking action on things like that would be the advice I’d give to someone starting out. Going back to the Sun Tzu quote, execution is won in these details.

If you were to build another legal startup, what would you do differently?

One of the main reasons that Atrium struggled is we didn’t have a clear value proposition. We were trying to win on a variety of dimensions. We competed on ease of use, having the best-trained staff, having the quickest service, having the lowest prices, the best tech, etc. We learned that our customers – oftentimes early-stage startups – would go to great lengths to minimize their cost. We didn’t work because our margins were not healthy enough. I can never know for sure, but if we would have competed on cost with a “good enough” service, that might’ve worked for the early stage segment.

If I were to take the Atrium opportunity and approach from first principles, I’d start with ‘how can you improve those margins?’ The real money in legal work is doing specialized work for bigger companies. 

There could be opportunities going the reverse way. Start by offering the suite of services to bigger clients. Have a roster of legal talent that customers trust. This could work because a viable minimum product in this market requires one to offer the whole menu of services - customers want to stay within the law firm. Over time there could be opportunities to increase margins. Atrium found success in upskilling paralegal talent on the backend. The questions here are ‘can this be venture backable without significant tech? How much value can tech drive?’ I am unsure, but now with advances in AI, I hope someone finds success. Making operating startups frictionless is great for the world.