AbstractOps Interview Series: Charles Yang 

by Adam Spector in

Charles Yang, a self-described “hyper-extrovert,” has the gift of gab. That ability to talk paired with genuine excitement to learn has served him well in his two years in the startup world.

Yang went to the University of California, Berkeley in search of a secure path: he’d be a doctor or he’d be a lawyer. But a detour kept him from enrolling in law school and sent him to Atrium, the Bay Area tech company offering software and in-house legal advice for startups. After a year picking lawyers’ brains, Yang made another pivot, talking his way onto the fundraise concierge team at Atrium. A fateful night of drinks and bad startup jokes eventually led him to AbstractOps.

At an early-stage startup like AbstractOps, everybody wears at least a few hats. But first and foremost, Yang is the document guy. At Atrium, he’d pore over internal documents for hours while building capitalization tables, working through compliance and due-diligence issues, and completing financings. “Not to sound like a psycho, but in my free time, I would sometimes go through some of these documents just to learn about these companies,” he says. “And I’m like, ‘Wow! It’s almost like a drama, dude.’ I couldn’t believe I had that access — what a great learning opportunity it was.”

As Operations Manager, Yang gets to employ both his deep document-level literacy and his love of client-facing work. It was a strange path from a poli-sci degree to a paralegal position to a fundraising role to one of the first hires at AbstractOps. But that path helped build a diverse set of skills that lets Yang be just as effective on a call with a client as he is deep in the weeds of due-diligence minutia.

After spending any time at all with Yang, it will come as no surprise that he’s assigned himself one more hat to wear: “I want to be the culture guy at AbstractOps.”

AbstractOps: How does someone with a degree in Political Science and Government arrive at a startup like Atrium?

Yang:

Good question. My parents are still asking that [laughs].

I started college with the concept of doing either med school or law school, and poli-sci caught my interest. The whole idea of the ruling of man was so interesting to me.

It was the epitome of what you want to study: it has history, psychology, and statistics. 

I took the LSAT when I was a junior planning to go to law school and I did well. But then about three months before graduating undergrad, I got hit up by a friend who I met in college who was then the Head of Growth at Atrium. He said, ‘I know you’re thinking about doing law. Maybe you want to experience what it’d be like to work with corporate attorneys? I know you’re a go-getter and a quick learner, and this would be a great opportunity for you to get experience in startups too.’

Going to school at Berkeley, the idea of ‘I worked at a startup’ is like a badge. At first, I was iffy, because I just wanted to get law school done with and get on my way, but then I was also like, ‘

I did switch majors a couple of times in college. Maybe it’s a good idea to test it out a little bit. Check out what lawyers actually do.’ Because I just imagined it like Suits — like, high-level negotiation.

AbstractOps: What finally convinced you to put off law school and join Atrium?

Yang:

The interview process checked a huge box for me. Out of all the internships and jobs I’d done before, it was the fastest moving. I went from initial screen call to offer within a week, and we had squeezed in two onsites and another screening call in between. It made me really excited, because I’d never experienced an organization that was able to handle that kind of initiative and action.

So, I joined the team that handled financing. I worked with startups who were raising money from venture capitalists and we specialized in it. And within a week I was there, I got put on a deal where one of the investors was the founder of Reddit and he’s responding to an email I sent. I was like, ‘Oh my god! It’s the founder of Reddit! What?!?’

I had a great team. I think if nothing else, the best thing that Atrium had going for it was the company culture was ridiculously warm. All the attorneys were happy to sit down and teach.

Any time I had a question about dilution or certain legal issues, an attorney would literally just sit down for 30 minutes, explain it, draw it out for me. Where else would you get someone to just spend time to do this for you?

For the first year or so, that was what it was like; it was just constant learning.

By my second year, Atrium had spun out a different wing for helping our clients fundraise called Fundraise Concierge. I loved client work and had experience dealing with fundraising from working on the financing team and so I hit up Jimmy, the person they were bringing up to run it and said,

‘Hey, I know normally you’re probably looking for someone with an iBanking background, but just let me know what you need help with and I’ll just deliver.’

He gave me a few side projects, I hustled for a little bit, and then he went into a meeting with an ESports company cold with just stuff I’d prepped for him and it went incredibly well. So, he brought me onboard and for the next year and a half we helped raise a couple hundred million dollars for our clients. It was a surreal experience and I’m so thankful.

My biggest strength, outside of just being lucky and being in a good spot at a good time, is that I’m a fanboy — I get excited for my clients and want to see them succeed. I felt so lucky to be a post-grad getting to see these companies getting built from the front row. And not just the front row — you get the documents, you see their internal workings, you get everything. It’s like, ‘Oh, this is how they structured this. This is how they hired this person.’ You’re just watching a life story.

AbstractOps: When did things at Atrium start to take a turn?

Yang:

I joined Atrium at about 40-50 people and, by December 2019, we were about 200 or so. At that point, we had hit a growth point where we had a decent amount of clients but it was hard to break even further upstream. Growth was good, but it wasn’t rocket jet. And that’s what every venture capitalist wants to see. So, around the end of December and early January, there was a huge pivot where the company moved all of the attorneys and legal team to external, AKA they laid off the entire legal team. It was crazy.

After that pivot, for the next two or three months, it was just mayhem. That was the most stressful time, but also I never experienced fire under my ass like that before. My job was essentially saved by switching over to Fundraise Concierge, but the whole legal team that I’d worked with was laid off.

It was heartbreaking. It was like watching your home from the last two years burn down right beside you.

That was when I started looking for new opportunities just in case the pivot didn’t work out.

AbstractOps: So, how did you eventually take the leap and join AbstractOps?

Yang:

Hari and I had been talking for about half a year at that point. We’d met at an event where we were kind of showing our clients around to a couple investors and I met Hari there and we hit it off. Hari thought I had figured out social hacking as a hyper-extrovert; I think I was a few drinks in making dumb jokes about startups.

At the time, he already had the conceptual idea of AbstractOps and we’d just get coffee and he’d ping, ‘Hey, what are some pain points from the service-provider side that you’ve seen from the client side?’ At that point, I’d already run like 50 financings so I responded, ‘Okay, these are things I’ve seen repetitively over and over.’

Hari’s first product idea was this data room: this storage of documents with the ability to disseminate the information within each one. It spoke so much to me.

At Atrium, I’d often brought up: ‘We have all these documents. If we were able to anonymize most of the information, you just have this incredible store of not just the raw data, but also the structure of how the data is linked to each other. Why aren’t we utilizing this?’ 

I’d gotten a return offer to Atrium post pivot, which I was considering, but then Hari and I were getting a drink and he just popped the question: ‘Why don’t you come work with me? I want to bring you on. I know we can’t pay you as much, but equity-wise you’ll do well.’ And I was like, ‘I’m young. I can take a risk.’

The biggest thing for me was that I wanted a better generalized learning experience. The thing about Atrium that I’ll always appreciate was I was essentially put on a fast-track to learn about so many things just by being close to all these professionals who’ve been doing it for decades. And so, I noticed the potential to grow with AbstractOps, ‘Hari has experience as an operator and Adam is incredibly process-oriented and organized. I can build something while essentially learning how to be a COO.’

You want to be the person who when a situation comes up, you know exactly how to deal with it. So, I signed on.

I took the leap from the law school path to Atrium and from Atrium to AbstractOps, because I have this mentality that I should be constantly hammering away at my perspective. I’d gotten this from older friends out in the Bay Area, a lot of whom said, ‘Take a more generalist view. Try to hop between roles. Try to figure out anything you can do just to learn it all.’

So, as I’m gaining this new knowledge and experience, it’s readjusting where I’m imagining I’m gonna be. I’m getting used to not having set plans. I remember in college I’d say, ‘in five years hopefully I’m on partner track in a good law firm.’ Now, in five years, I’m like, ‘Dude, I hope I’m just not in jail or something.’ [laughs] That’s the bottom bar I’m gonna set: not in jail. The rest will just be readjustments that come along with the more I learn.

AbstractOps: What’s different about your new role compared to what you were doing at Atrium?

Yang:

At Atrium, I started as a paralegal, and then I moved into an analyst position for the Fundraise Concierge. I had cyclical tasks that I was doing. But with my current position, Hari gives a lot more leeway and I have a lot more input. For example, when we were setting up how our data schema and docs were mapping out to information, we would sit for days on end on calls discussing why this makes more sense or why this doesn’t. And one of the things I appreciated most was when there were points I felt really strongly about based on prior experiences, like, ‘Hey, I dug through thousands of these documents. This is gonna come up,’ Hari was very open. He was like, ‘Hey, you’re right. This makes more sense. Let’s try it out.’

But the similarity between the two roles is that the client-facing nature of it makes it so exciting.

I get to sit at the forefront and watch people build cool shit. There’s nothing better than that.

AbstractOps: You’ve built this knowledge-base over the last couple of years — how does the client get access to those learnings?

Yang:

90% should be built into our system. T

he remaining 10% is that the client has access to this ProCOO with specific, high value, relevant knowledge.

As a team, we have this incredible collective pool of skills. BK is a coding wizard. Hari is an expert operator and knows a lot about equity. Adam knows a lot about products, processes, SEO, things like that. And I know a lot about fundraising, financings, and very niche things like, ‘What’s a good way for a founder to pay himself without having to pay himself for taxation?’

The documents are fully within my domain.

When we onboard a client, they give me access to their documents and I try to map out their company’s storyline and convert that into data. Using that data, we can start to make informed suggestions.

Like, ‘Hey, we noticed you’re already making this much money, your ARR is at this rate already. Why not switch over to this bank?’ Or

‘This credit card makes more sense for you.’

Or ‘We noticed you use this vendor but you should probably use this vendor instead for these reasons.’

I’m also lucky that I can utilize the network I built up at Atrium. A lot of the attorneys and managers that I’m friends with will still hop on a quick call to teach me or answer questions. So, that’s the last thing: I’m committed to that kind of lasting culture that transcends the workplace, so I want to be the culture guy at AbstractOps.

AbstractOps: Let’s jump three years into the future. What does AbstractOps look like and what it can do for the startup landscape?

Yang:

Okay, well, we just raised our B or C and teams are built out, but our company hasn’t lost our truth-telling, candid style. We’re bigger, but there’s still no corporate bullshit, even though our entire stack is utilized towards corporate compliance. So, hopefully, we’ll be around 100 people and those 100 people will be excited about where they are.

I think a lot of people fresh out of college or in junior roles in their careers don’t really realize how important it is to be in a position where you feel like you’re learning and growing.

I want us to be at a point where everyone’s still feeling up-leveled and growing.

Hopefully, in three years, we can be at that place.

And what can we be doing for the startup landscape in general? I’ve always appreciated people who build those simple tools that you go like, ‘Wow, I love using this.’ It just makes me happy. An example of that is Notion or Airtable. When I first used them, I was like, ‘Wow. This is pleasant.’ I never thought using a tech product would generate the same happiness as hearing a new song.

And those tools have now created little stepping stones that other startups can then use to build new things. I want AbstractOps to be a tool like that for other startups.