Climbing The Ladder/Essays & Confessions

The Toast’s Daniel M. Lavery On Work, Writing, And The Cost Of Creative Freedom

By | Monday, December 07, 2015


As someone who sits squarely in the middle of the “young, New York-dwelling woman” and “writer who writes primarily on the internet” venn diagram, the fact that I am a Daniel M. Lavery fan is probably the most unsurprising thing about me. Daniel, and his brilliant, hilarious website The Toast, are two of the things on the internet that consistently inspire people with the possibility of having it all, creatively. His work is concrete evidence that you can be funny, smart, creatively uncompromising, and still turn a profit. And in a world where more and more media outlets are forced to sacrifice creative integrity or niche appeal at the altar of business, The Toast’s very particular sense of humor and tight-knit, hyper-engaged community feel like a bit of an internet oasis.

But the truth of how The Toast manages the business of creativity is, as with nearly any publication, not a perfect straight line towards success and independence. Their path has been a mix of hard work, financial benefactors, and smart business decisions, which are all pretty par for the course. But what’s unusual about Daniel, and The Toast in general, is how willing they are to be open about the financial realities of creative work. Where most people like to keep their financial skeletons firmly in the closet, Daniel is perfectly fine talking about them, even the things that don’t fit the perfectly-flattering, bootstrapping narrative so many entrepreneurs love to follow.

I spoke to him recently about creativity, the nitty-gritty of running a website, and all things money. Please enjoy an edited version of our conversation below.

The Financial Diet: Were you always a writer? Did you have any other jobs, or did you just go straight into writing after school?

Daniel M. Lavery: So, no, I have not always been a writer. (Though I am a relatively young person, so it’s not like I had decades of experience in another industry.) I graduated school in 2009, and spent about a year and a half waiting tables. Then I got a job in publishing, academic publishing, where I worked for almost three years. And maybe a year and a half into that, I started writing on the side — mostly for free, for smaller/obscure websites who would be interested. So for that year it was things like “writing Vampire Diaries recaps for a small pop culture website based in DC,” things like that. So it wasn’t really until the last year of my publishing job that I really started getting paid to write, and by the time I left that job to freelance, I was making close to what I was making in publishing, through freelancing. So I kind of got to a point where I didn’t have a ton of money, but I could definitely live off of it if I wanted to quit my job — so that gave me about a year bridge between the two.

So that gave you essentially a year where you had a whole second income to prepare?

Yeah! At the time, I was making about $35,000 a year plus benefits, which isn’t bad. And I actually had two weekend jobs in writing (weekend editor at Gawker, and weekend editor at The Gloss). So that meant Monday to Friday I had my regular job, Friday evenings I would prepare my writing for The Gloss, Saturday and Sunday I would work for Gawker, and my other freelance writing I would do on weekday evenings.

So during that transition time, did you make it a point to live any differently, or save more money, or anything like that?

So I mean, I was also living in San Francisco at the time, and between all my jobs I was making a little under $50,000, maybe $55,000 for a few months, so while it was great to have that extra money, most of it went to rent. (And savings, of course, because I knew if I wanted to leave to write full-time, I’d need a good amount of savings.)

Did you have a specific savings goal in mind?

I wanted to have about a six-month cushion of all my bills and day-to-day needs, which I think I got pretty close to — I had about a five- or six-month cushion. And I was really lucky, in that I graduated with no student debt. And I cannot overstate how significant that has been in my life in terms of how I can make career decisions. I’ve just never had to worry in that way, which is impossible to overstate. I don’t know, if I didn’t have that, if I would have been able to quit my job when I did, or at least I would have had to be much more cautious.

So how long were you a freelance writer before you started the site?

Oh my goodness, so briefly. So I quit my job in publishing, and about two weeks later a friend at Yelp told me about a job there as copy editor, and it paid like $50,000, which was huge to me at the time. So I took that job, and about two weeks in, got a job offer from The Atlantic to join them as a staff writer, so I quit Yelp after about three weeks. I was not a good investment for them. But this was also at the time that I was developing the idea of the website with Nicole [Cliffe, her partner at The Toast]. So I was talking to The Atlantic about doing both, and it became really clear that it wasn’t going to be possible.

So I had to make a decision about which opportunity I would take, which was a tough couple of days, in terms of making that choice. I mean, if you had told me before [conceiving of The Toast] that that I would have been offered a staff writer position at The Atlantic, I wouldn’t have thought twice about it, I would have just said yes. And it was a bigger paycheck, more prestige, a lower chance of failure. So it was very hard to move on from that opportunity, but I ultimately did, and all told, I was a freelancer for about five months.

So the woman that you started The Toast with, Nicole, she’s more of a businessperson than a writer in terms of her function?

The way that we kind of describe it is that there are two ways of being a businessperson, and you’re either a Bert or an Ernie. And I’m an Ernie to the core. And Nicole is an Ernie at heart who takes on Bert tendencies when she’s around another Ernie. So Nicole is a wonderful writer, she wrote every day at The Hairpin, which is how I came to know and love her. But she definitely handles more of the business things now, because all I’m good at is writing, whereas she is good at both. She handles a lot of the day-to-day business of the site, and all the different aspects of running it.

Now, she has stated before that her husband has been sort of able to fund The Toast into existence in some capacity. Was she looking to invest money specifically in a media project, or did it just kind of happen as an idea and then she happened to have the resources?

So Nicole and her husband both met at a hedge fund, and they both brought a lot of robust financial health to their marriage. And when Nicole and I knew that we wanted to start a website together, it wasn’t just a case of her wanting to get into the web publishing game, as that’s generally not a good way to make a quick buck. So when we founded the company, she pledged $100,000, and we ended up using less than half of that to get the site started. And we were turning a profit within three months.

And, you know, I love that she was able to talk about her husband and their shared resources, and how that’s been a safety net for us, because if I had started by myself this would have been a totally different experience. For example, when we did our redesign, we could have totally emptied our coffers to do it, but we didn’t have to because we had that husband to back up that purchase. But it’s not as if every month he’s signing our checks. So he is a safety net, and Nicole is very transparent about that, but she has also brought money to that table, too, and I think that’s some of her natural Canadian self-effacing nature.

I think sometimes people really don’t like talking about where their stability comes from, or what’s holding them aloft in some precarious financial way. And she just wanted to be really open about the fact that, look, we do okay, but if we didn’t have that resource, it would be a lot harder to deal with the fact that about a quarter of our readers use AdBlock. It would have been harder to pay all of our freelancers during a lean month, or get through August, which is a notoriously a slow month for sites. So we’re not making huge money, but we’re earning our keep, and it’s not as though we’re being totally floated by this rich, handsome sponsor.

When you say you were profitable within three months, I’m assuming most of that is coming from ads?

Yes, and it’s a conversation we’ve been having more and more recently, in terms of how we can provide alternatives to our readers because obviously a lot of them are using things like AdBlock, and while we do some sponsored content, we just don’t do a ton of it. So we are constantly talking (like everybody else) about how to keep up with that, because we don’t ever want to put intrusive or unattractive ads up that might make us more money but really hurt the user’s experience. It’s not worth it to us, and we’re really based on our community, we’re not some big site that’s pushing out just tons of content, we have a much more niche thing. We’re trafficking in loyalty. So we thought, what do we hate? Pop-ups, autoplays, pre-rolls, etc. And so anything that we wouldn’t want, we wouldn’t push on our readers — which does mean that, at times, we are turning down more money that we could be making. But part of being independently owned and operated means that we can make that call, and that’s hugely valuable to us.

There’s obviously a big conversation on the internet right now about writers getting paid, and the ethics/politics of working for free. I’ve always been of the opinion that in some cases, writers should work for free when they are just starting out and really could use the platform or piece for their portfolio, and it’s something that was hugely instrumental to me getting started as a writer, and many other people I know. Where do you fall on this, especially now that you are on the other side of it, paying writers?

Yes, as far as the conversation, I see more of it now that I’ve been an editor as well as a writer. It was very important to us from the beginning that we pay writers, we’ve always paid them. We don’t offer them competitive rates with something like the Times, sure, but we always pay. And yes, you can see in terms of traffic, like “Oh, we paid $75 for this and it’s not getting any traffic, it didn’t earn itself back.” So I do understand why smaller places might not pay everyone, and it’s not as though they have fat coffers of money and choose not to pay out of wickedness. I understand that.

I definitely wouldn’t say that it’s great to work for free, particularly past a certain point in your career, but I think it’s also crucial to understand the environment that you’re working in. The truth is that it’s not always easy to earn money writing online, and there are different trade-offs for everyone, but for me in my personal experience, I did some writing for free for about a year. And for some places, I still would, but I also got to a point where I started charging, and that was a good thing for me. I think writing for free can be helpful for a little while, but it will come to a point where it’s no longer helpful.

And regardless of where you are, I think it’s always important to ask for money. The worst thing they can say is no, and it’s important for you to make the decision of whether or not it’s worth it for you to do that work. You have to look out for yourself in the marketplace.

When you said that Nicole pledged that $100,000 up-front, was a big part of that pledge initially to be able to pay writers out of the gate?

Yes! Because we did, we did pay them from day one, and obviously we were paying people before we had ad revenue. And we initially started out paying everyone $100 across the board, regardless of the length of the piece, and we quickly realized that we were losing a lot of money on that, so we shifted to the sliding scale. So we have several rates, and we also do some profit-sharing with frequent contributors who have asked for more money. And it’s allowed us to find a balance between “giving people money” and “not losing money month after month on work that’s not earning itself out.”

And we’ve talked about getting funding, but we’ve really just realized how nice it is not to need it. We could go out and seek a million dollars or whatever, and we could hire really great staff writers with good salaries and invest in that, but then we would have to be beholden to our investors, and do things differently, and really chase after certain numbers and targets. And so one of the things that’s great about our site is that we offer ourselves total creative freedom.

But you know, for example, Nicole has never taken a salary from the site. She’s never paid herself. And on the one hand, she’s really lucky that she’s able to do that, but on the other hand, that’s years of free labor, 40-50 hours a week. And that’s just a reality of one of the ways we’ve been able to save money to pay writers. I started out making $2500 a month, and that was my only job. I haven’t had health insurance until this year, and I lived in a windowless studio for the first two years of the site. So, you know, I want to be a good mix of transparent and realistic, and I want to share the ways in which we’ve been lucky, but also the ways in which we’ve had to cut corners. And we do pay our other employees and contributors, just to make that clear, but Nicole still insists on not taking anything so that the money can go elsewhere.

What is something that you know about making a living at creative work now that you are running a site, that you didn’t know when you were just a writer, and you wish that more people were aware of?

Gosh. Well, I don’t know if there was anything I wish more people were aware of, because every creative career can be very, very different. But you know, I sure understand now what people were talking about in terms of the post-recession, “hustle” economy, where everyone has multiple gigs, multiple streams of income, rather than just one steady job. Even today, with the book, and my Slate column taking over Dear Prudence, having different jobs now is still very helpful, and it’s always been important to embrace the “fits and starts” nature of creative work. And I think that that’s something I didn’t realize, even when I was starting The Toast. I didn’t realize that I would need multiple sources of income to move past “just being able to pay the bills.”

Even running the site, I have to make a lot of financial decisions that just come with being my own boss, starting a company, and being the one to make those sacrifices. I want to create a site where the next generation of employees can be more comfortable, and I won’t have to ask them to make those financial sacrifices — we’re not a big player by any means, but we can work towards that stability.

Well, if you’re not competitive in terms of pure revenue, I think The Toast is arguably in a better place than some of the bigger sites that are beholden to investors, who live and die by their traffic, who are forced into layoffs or huge restructuring at the whims of the board or what have you. And that allows you to do the creative work that you want to do, on your own terms, which is obviously a hugely attractive part of the job.

One of the things that is great, when we talk to freelancers, or when we’re looking to bring on a more regular contributor, is that “Yeah, we’ve got numbers goals we’d like to hit, but we also want you to write whatever you think is interesting, and we’ll see if it pops.” There are a lot of things we do that we would not have been able to describe effectively or sell to a more “mainstream” site, and yet they’re some of the most popular pieces we’ve had. We never would have found that out if we didn’t have the freedom to do these more experimental articles.

And ultimately, looking a year or two ahead for The Toast, even if it feels in competition with making more money, I want to keep that tone. I think if we lost or sacrificed that, we would lose what we have. There are other sites that are better at being very profitable and doing more [generally popular] work, and it’s not for us to ape them. And we do make small but reasonable steps towards paying people fairly and making good, lasting hires. And while I don’t want to leave any time soon, I also don’t want to be three years down the road and totally burned out on The Toast, saying “we have to hire my replacement tomorrow.” I want to be able to put a structure in place slowly so that it can flourish on its own, and plan that out thoughtfully.

My dream is that The Toast can continue on for another five to 10 years with a small, reasonably well-paid staff, and I think that’s possible. I think that we’re on our way there. We are doing better as a site than we were a year ago, or two years ago. We’ve been able to get raises. We’ve been able to pay freelancers. And my doing better in outside projects is better for the site because it means I don’t have to depend on it for all my income. I was slated to get a raise last month but I talked to Nicole and I said, “look, I just got this new gig, let’s use that money for something else,” and we found something great to use it for. And that feels so good, to be able to help the site like that. Because there have been times that I have had a sudden expense, and Nicole would wire me money. I have been able to depend on her as a safety net with little loans over the past two years, which I’ve always been able to pay back, but still. It’s great to grow past that.

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