I kept waiting. For a year and a half, I waited. The revenues kept trickling down. It was this long terrible process, losing half overnight but then also roughly 3% a month for a year and a half after. It got to the point where we couldn’t pay our bills. That’s when I reached out again to Matt Cutts, “Things never got better.” He was like, “What, really? I’m sorry.” He looked into it and was like, “Oh yeah, it never reversed. It should have. You were accidentally put in the bad pile.”

Two weeks later traffic went back to how it was. But in those two years, the ad revenue market had changed. Even with the traffic, we were making half as much money because the market had kind of died in the interim.

You mentioned making a lot of money from 2009 to 2012. You were a business that was built solely on a different platform that you didn’t control. How did you make a lot of money, treat your employees well, but not save for a the rainy day?

I would say early on it was a pretty healthy mix of revenue at the start. Some revenue came from Amazon. Any mention of a book or something got associate fees. I was represented by an ad company that was specializing in banner ads on blogs. Then Google. Those things were kind of even. They were 30% or so of income each.

But by 2010 or ’11 it was like 95% of the money was coming in from Google, and other ad companies were dying or being bought out. I remember showing friends how my revenue was from a single source, going, “This is nerve wracking,” and them going, “Oh my God, you should never be in this position. You should diversify. Burn money on something else in the hopes that someday it pans out, like try something else. This is terrible. The day they turn it off, you’re dead.” And then that’s what happened.

Did you try to diversify and work on something else?

We tried little things. We boosted the Amazon stuff a little bit. In 2010, the iPad came out. Make an iPad magazine was a popular idea at the time and we spent some time and money on paying another company to build an app. Then again, nobody ever made much money on an iPad magazine, so it’s probably a good thing that I never went too far down that path.

I think I knew the writing was on the wall before 2012. I saw it in the abstract. We’re going to hit a wall someday. Someday this is all going to go away, and then one day you wake up. Oh, shit. Today’s the day.

ask.metafilter.com’s Traffic

But I thought it would be a slow descent, not a wall. Early on, I got advice from a friend who was making a lot of money on a big web property. I remember asking him, “What do you do when it starts making serious cash?” He just said, “Plunge it back into the business. Pay people crazy amounts. You’re either going to give it away as taxes back to the government, or you could give it to them. Don’t be a jerk and hog it all yourself! If you make a million dollars, don’t keep $900,000 of it and pay $100k to employees. Pay them as much as you possibly can and it’ll help the business and be your way of re-investing.”

And that’s kind of what I did. Staff got paid well. We had benefits galore. I think I tried to spend as much of the money as possible on the business in this way. Everyone had nice chairs and dual monitors and new iMacs.

I would say definitely the biggest regret is not having a stockpile. I read somewhere that I should have 6 months of expenses in the bank but it seemed impossible. Ideally, you can sleep at night if you have 6 months of salary in the bank for everyone. I don’t know why I didn’t make that a priority. At most, we always had one or two months of payroll sitting in the bank, and that was it.

Why didn’t you think about having a savings account? Keeping a savings account is plunging it back into the business; it’s making it sustainable.

I didn’t think of it that way, stupidly. I don’t mean to sound like a goofy politician but I came from meager means. My parents always had shitty small businesses that never made much money. I didn’t have any adults, like country club adults, around me to to tell me, “Oh, you should have a lawyer for that, you should incorporate as this in this state and you could avoid this tax.” I didn’t know anybody like that. I was financially illiterate until my early 20's.

I felt like I stumbled around getting conflicting advice from people. It took me years to find people that taught me about real business adulthood. It felt like being at a kid’s table until then.

Getting a really good accountant, getting a good business lawyer, having some sort of business mentors in your life is amazing. My parents were not it, and none of their friends were. It took me years to find a good investment person who knew great accountants, lawyers, and everything. My shit was in order by 2011, but only because I’d stumbled upon a good network of people that knew things I didn’t have access to before.

It’s easy to say in hindsight that if I had known any of that stuff in 2005, things would’ve been drastically different. But weirdly, people hardly ever write about it honestly online: how to be a business-y adult, or when they do write about it, they write for an audience of people who already know. People tend to talk about it in a shorthand. Because everyone knows this, right? Wrong.

If you have no idea what an S Corp is, there’s not a lot of hand-holding help for you out there. I was a stupid, bumbling idiot combined with money. My spirit animal was Kenny Powers instead of Warren Buffett.

The one year anniversary of you stepping down from MetaFilter just passed. How did that come about? How’d you decide to leave and how did it survive you leaving?

In 2014, I realized I was completely burned out. I was working 40 hours a week in the trenches moderating the site but then also running the organization around it too. Before I oversaw the site and there were 6 employees that did the moderation work, the day-to-day grind. After I took on one of those roles and then also did everything else — it ended up being 60 or 80 hours a week of work. I became miserable and anxious for a couple years.

Then a company approached me and said, “Oh hey, do you want to run community for this other site that’s big and popular? We’ll just buy you and make that happen.” That was their first step but I knew it was outrageous. The deal never worked out, thank goodness, but they gave me the idea. Maybe I could hire someone to replace my hours, and then decrease my daily involvement, and transition away. It was the first glimmer of hope that maybe I could go do something else instead of being miserable working 80 hours a week.

I realized early on with MetaFilter that it’s a weird beast, being a community site. It’s not mine, I just participate on the site. Yeah, I built it, but people there make it great — both the staff and the members. I felt like if I left, it would go on and be fine without me. There’s a great staff that has been there for years and years that know how to keep it up.

So after that other opportunity died down I emailed Stewart, the CEO of Slack. I’d known him for years. I said, “If there’s ever anything there, let me know. I really love using Slack and would love to help build it.” He eventually got back and said, “Let me think. If I see something I’ll send it your way.” Shortly after they asked me to join as a writer and I said yes.

I asked one of MetaFilter’s part-timers if they could work full-time and they said yes. I accepted an offer on a Friday and started work the following Monday for Slack.

How’d that work out? How has you leaving affected the site? How’s MetaFilter doing a year later?

My ultimate goal was for the staff to run it and keep it out of my hair. In my ideal world, they’d call me once every three months when something insane happened. And the staff has done an incredible job, going beyond my wildest dreams. They’ve taken everything off my plate. I’m lucky. I’ve been telling friends it’s like I own a restaurant in LA — I don’t get to eat there or have to run the kitchen anymore but I’m some sort of silent owner. I would love to transition my ownership legally to the staff somehow. Still working on how to do that.

Revenue went up by a bit after I left and they’ve stockpiled that cash. They’re only spending money on salaries. 90% of the cost of running the site is salaries, but those are fixed. It’s been stable. They have six months in the bank now, which is incredible. They’ve since added features to the site in my wake, which I love seeing.