Headshot of Charles drawn in an illustrative style

Issue 3


Taking Business Personally: A Conversation with Charles Broskoski

written by Meghna Rao

art by Lisa Yu Li

Meghna Rao is an editor and writer from Queens, thinking about diaspora and technology.

Charles Broskoski is the co-founder and CEO of Are.na, an online Montessori school for adults.

This interview has been edited for clarity and length.

Here’s a story you might find familiar: you sign up for a startup service one day. Let’s say, for the sake of this example, that it’s a social media network that lets you upload and share photos with your friends. You find this fun. You take photos of silly moments, moving moments, beautiful moments. The images spawn a culture unique to the platform. Memes become self-referential. More friends join, and so do extended family, celebrities, your favorite magazine.

One day, a few years down the line, you look up and realize that it’s no longer the same service you signed up for. Your feed shows more brands than family, and you learn about your newborn cousin two weeks late. The people you’re following are posting sponsored content, or they’re not posting at all. You’ve been given an endless scroll, so you find yourself falling through hours of recommended videos of strange recipes and struggling to exit.

It’s this feeling that Are.na, a platform for connecting ideas, is trying to avoid — and it’s doing so by eschewing traditional expectations of startup growth.

Are.na is 12 years old, just a few months younger than Instagram. I found my way to the platform on a friend’s recommendation when I needed a place to put all the weird and varied media that influenced my internet brain — TikToks, screenshots, PDFs. You can use Are.na to link all of your weird online stuff, my friend told me. You can organize it into channels and browse through other people’s weird online stuff.

In some ways, Are.na felt familiar to other startups I’d encountered — easy to use, obvious how to sign up and unsubscribe, transparent about how they’re building their product. But there were other parts that were unfamiliar. Namely, that there are no ads on Are.na, that there are still active users from a decade plus, and that the startup limits its expansion plans to grow mostly by word-of-mouth.

It’s a small startup that is growing at a steady pace. It currently has 25,000 monthly active users (MAU),1 0.00125 percent of Instagram’s reported 2 billion MAU as of October 2022. Around half of Are.na’s active members pay for premium services. As of July 2023, those subscriptions come out to around $70,000 monthly recurring revenue.2 They hope to reach $75,000 by the end of July, and update this goal each month.

A little over half the money goes to payroll (two full-time and four part-time workers). The remaining goes to everything else needed to run a business — servers, website hosting, software, taxes and other fees. They’ve never raised formal venture capital, but in 2018 participated in a ~$270K equity crowdfunding round that allowed people to invest to own a small stake of Are.na. Each new thing the team builds, co-founder Charles Broskoski tells me, is to ensure that the people using Are.na continue to like the product and stick around — that means monthly updates like fixing search bugs, editing design details, and adding features to the mobile app.

This is what Are.na believes in: Superfast is not the only pace for growth. It is possible to sustain and grow a digital business without throwing venture capital (VC) money at it. You can still build something lasting on the internet that looks the way you want it to. Eventually, Broskoski hopes Are.na will become the “next ​​Nishiyama Onsen Keiunkan,” a hot spring spa founded in Hayakawa, Japan in 705 A.D. — a sustainable business that is around for the long-haul.

Meghna Rao: You’ve answered this question in other places, but I think it’s important to ask again. How did you start Are.na?

Charles Broskoski: I think it’s important to say first that the throughline of this story — my thesis — is that more people should be starting businesses on the internet. It’s doable within certain parameters. And I want people to know that what they see when looking at Are.na today is just the result of a series of situational decisions we made along the way.

I have a background in art. Specifically, art on the internet. I had been hanging out on the internet on a platform called del.icio.us,3 which was the first social bookmarking website.

You could save links. You see a timeline of your bookmarks, and get a sense of where you were ten days ago, and what it led into next. You could see who else had saved the things that you thought only you were interested in, and you could also see the trajectory of what they were thinking about.

Similar to Are.na in some ways. But unlike Are.na, there wasn’t a social, communication component, right?

Exactly. Like Are.na, Del.ici.ous was first and foremost a personal utility. You could tell if you would get along with someone or not based on what their perspective was pointed towards. And I made friends with someone named John Michael Boling. There wasn’t really a direct message function but we’d follow each other’s work.

John was also making art at the time. We were both part of a scene. But then Yahoo bought del.icio.us, and there was no sense of what to do next. It wasn’t a political position, it was just like — OK, I guess we’re done here. We were like, they’ll fuck it up now. And they did; they did all of these things that made it unusable.

Everyone left. John Michael was badgering me to start my own version of del.ici.ous, and he wasn’t a programmer but he’d show me all these mockups and screenshots. He was looking everywhere for a short, interesting URL to purchase, and he found Are.na.

Then there was me — I was starting to feel weird about doing art commercially. I’d recently had a solo show, and it didn’t make me feel good. When I got back, John Michael had met this person he knew through his sister, J. Stuart Moore.4 He was the dictionary definition of an eccentric millionaire. He’d started a company in the ’90s, made a ton of money, and retired. They got to talking.

We were in agreement on some things. Like, there was so much stuff on the internet, we loved learning and engaging with work online, and we wanted to figure out a way to harness that more directly. We all went along with it. We hired three of our friends, all artists. Damon Zucconi, who is an artist and brilliant engineer and Dena Yago, also a brilliant artist who worked on K-HOLE.5

So Are.na really got its start because of J. Stuart Moore’s investment and his belief in your work.

It wasn’t even an investment. We were employees. I was paid a salary. I also had that odd experience of making more money than I’d ever had before, after being primarily an artist and making zero money.

So many artists experience that surge when they get a full-time tech job.

Yeah, and Stuart hired all artists. We had very specific ideas about what we wanted. Our bar was basically — can we get all of our snobby, intelligent friends to use it without it being a favor to us? Can we make something actually useful for them?

We could, and this was a huge win but Stuart didn’t see it like that. Still, we were like — no, this means something.

Stuart wanted there to only be certain types of acceptable content. Not frivolous memes. He thought the platform would be better if we controlled what went into it, but we were the opposite. As people who were embedded in this world, we knew — you never know what will lead you into something good and serious. Sometimes you have to take weird, windy paths. We thought it would be better if we just attracted smart people to it.

Our approaches started to diverge. And to Stuart’s merit, instead of firing us, he said — you guys care a lot about this. So I’ll give you the company.

Stuart changed my life with that decision. But suddenly I had a startup. None of us ever wanted that for ourselves. I’ve had a website since I was 13, and Damon and I are self-taught programmers, but prior to this we didn’t have any desire to be entrepreneurial.

We languished for maybe a year. We kept the servers on. Our friends were using it, some really actively. But it was extremely small-scale. There was no business model.

Everyone else was losing interest — except for me and Chris Sherron, who did all of the design. Together, we formed a new company and transferred all the intellectual property. We formed it as a Delaware C-Corp. I got a job because I wanted to get better at programming. And I convinced Daniel Pianetti, who I met through Are.na and who had all these ideas for what he wanted for the platform, to work with us.

Were you nervous at all? Scared that you had a company on your hands now, and that you had no experience?

Yeah, I was. The adjustment took a long time. But Are.na will be 12 years old in August. I wouldn’t be running a business if it weren’t for Are.na. It’s a very personal business, meaning that it is something I want to see in the world; it is a tool that I would personally be devastated if it were to not exist.

I think we have so many examples of assholes starting businesses, and if they’re the majority of examples, we’re only going to have shitty businesses. I want to see people with very specific perspectives and opinions on how to manifest things into the world. More people should take business personally.

You’ve only ever crowdfunded. Were you tempted to take traditional VC money and grow faster?

Yeah, when we formed a new C-corp it was in the middle of the [early 2010s] startup boom, and so many people were raising money on nothing. I even figured that we could try raising a little. We tried to apply for accelerators, but nothing ever felt right. It all felt off brand, you know?

We got a grant from the Knight Foundation in 2016. It was $35,000, which wasn’t much, but it was wind in our sails. And that money felt on brand.

We started to ask ourselves — what wouldn’t we be embarrassed by? That became our guiding star.

So it took a series of small yeses and nos to help shape Are.na into what it is today.

Exactly. The set of decisions that helped us develop what we wanted to do. We would talk to people — VCs, accelerators — and I think it never worked out because we didn’t want to do anything embarrassing. We didn’t want to feel bad or make a decision that felt wrong.

When did you cross the threshold into being comfortable enough with Are.na to sustain yourself?

So recently. I stopped doing freelance work to offset my salary two years ago.

It was hard getting to the place where we are now, where we feel comfortable. And I’m really happy we did. It feels so much better than if we were on the hook for something, or working with someone we didn’t like.

How do you measure Are.na’s success since you’re not following the traditional startup growth playbook?

We’re pretty in-touch with people. If someone writes in to help, it’s either me or Daniel who’s answering the email. We have a Discord where people tell us about what’s going wrong. I run our social media accounts. All of this makes our surface area of being connected to people very large, and people can express their satisfaction or dissatisfaction easily. So we always have a gut feeling about whether things are going right or wrong. But also, the only metric we really pay attention to is revenue. For us, it’s the highest bar. It sounds crass, but if someone is willing to pay for Are.na, that’s huge. Sometimes, we also track page views. No demographic or location. We don’t have time for all that.

But certain things — personalized feeds, maybe — help manage larger platforms as they grow, right?

It’s funny, I’ve never bought the idea that personalized recommendations are a response to growth. I feel like that’s an excuse to build an endless (addictive) content stream that’s financed by ads. Because we grow at a slower pace than most social platforms, and because we are fairly close and available for feedback to the people who use Are.na the most, we can do this more organically, for now.

End-experience wise, I really can’t imagine a world where something like an algorithmic feed is the best response for many more people using Are.na, because it really kind of defeats the purpose of the whole thing. My feeling is that algorithmic feeds are just disrespectful; they disregard all the nuance in taste a person has. For applications with heavy personalized recommendations (I’m thinking about some streaming services, or even TikTok), I would personally be so much happier and interested with a truly random output.

To date, the biggest product change we’ve done with growth is to make sure the infrastructure can perform with increasing load. That was a large amount of work. We started it because people were complaining about slow load times, and we experienced it ourselves, as users.

Do you ever worry that a much faster competitor will come in and make the same thing and beat you to it?

No, not at all. The reason the quality has remained so high on Are.na is because we grow slowly, and we have the patience to do that. And that’s why I think we can be in this for a long time: the primary goal is not to to make a shitload of money.

Having a strong point of view about this type of thing is a meaningful differentiator. A lot of other platforms are diluted; their ethics do not translate to their product choices. People who discover Are.na are like, wow, finally, something with a different perspective than Facebook. I’m old enough to remember when the internet was like school, when there were plenty of places that would help you think and grow. Even though Are.na has grown, the way that people are thinking on there is still so interesting. The places where people’s gazes are pointing to are fascinating.

The goal is to be good. You know? That bar, for what “good” is, keeps going up. And for us, the only way to be good is not to grow fast. That’s just how it is. We’re not really interested in becoming like Facebook, TikTok, or Instagram.

I think it’s a foreign idea for people to hear that they don’t need to just go with an erratic, crazy pace of growth. I like your roadmap — your next steps are mostly just ways to make people who use Are.na happier.

Yeah, exactly. Why can’t there just be more normal, functioning small businesses on the internet? Why does it have to be this narrative of we’re going to be billionaires and start a dynasty of unhappiness? Why can’t we just keep our expectations at realistic, human-scale levels?

I know we’re not for everyone. But the people who are attracted to Are.na in the first place are those who care about that type of thing. And I think that will eventually make a big difference.



  1. “Active users” considers people who interact with a piece of software over a set time.

  2. Monthly recurring revenue (MRR) is a common metric that subscription businesses use. It’s the predictable income they’ll make from monthly subscriptions.

  3. Del.ici.ous was founded in 2003 by Joshua Schachter and Peter Gadjokov. It raised a rumored $2M in April 2005, and was acquired by Yahoo for a rumored $15-$30M by December 2015. After exchanging hands several times, the company was acquired by Pinboard in 2017 and subsequently shut down. It’s currently read-only.

  4. J. Stuart Moore co-founded IT consulting firm Sapient in November 1990. In 2014, Publicis purchased Sapient for $3.7 billion, or $25 per share.

  5. K-HOLE was an artist collective operating 2011-16, issuing trend forecasting reports that mixed parodies of consumerism with personal observations about culture. These reports eventually landed them with work for big companies like Coach and MTV. K-HOLE invented the term “normcore.”

headshot of Meghna Rao


Meghna Rao

Meghna Rao is an editor and writer from Queens, thinking about diaspora and technology.

headshot of Charles Broskoski


Charles Broskoski

Co-founder and CEO of Are.na, an online Montessori school for adults