Kristen Hawley on Inventing the Restaurant Tech Newsletter

Tell me about your first-ever job. 

Oh, I was a nanny and then a babysitter, sort of an under-the-table thing. Does that count? I was a regular babysitter for a family with three children in Pennsylvania, where I grew up in Harrisburg, kind of near Hershey. I was a nanny and babysitter for these three kids, where the oldest was not that much younger than me. We’re all friends now. Two of the three have children of their own, and one of those kids actually babysat for my own kids when I was in New York City. That was my first unofficial job, I guess. And then I worked at the mall. 

Where did you work at the mall? 

The Limited. I was terrible at it. I was a terrible salesperson. I was like, “Oh, you don’t need this.” 

What got you interested in hospitality? Were you always into restaurants and food? 

No, I started just being interested in features journalism. I worked at magazines in New York for Hearst. I sort of fell into food lifestyle and digital, back in 2007 when they were pulling Hearst off of iVillage. I floated around and then ended up working full time at Country Living magazine. 

Was that when Hearst still had entirely separate print and digital operations?

Yeah, it was weird. I had two bosses, so I sat with the magazine, but I reported 50% to the editor in chief and 50% to the digital director. Which meant no one was paying attention to what we were doing. But it was also really fun because we had this great digital media org with one or two editors per title, and we were all pretty young and excited, and we got to sort of do whatever we wanted. 

Then I helped launch delish.com, which was my first official food role. I wrote a blog about Top Chef. When Delish launched, it was kind of cool! It has pivoted to be more of a utility and recipe situation since then, along with viral stuff. So I was working at Delish in 2009 when I got laid off along with everyone else. 

And so I moved to California, to San Francisco. I was like, oh, I like it here, I’ll do freelance or something for a year. I’ll figure it out. I had never really lived anywhere else besides the East Coast. I ended up working as tech editor at Popsugar. 

I started to notice how because San Francisco was such a tech town at the time—every town was a tech town in 2010—the restaurant experience was different. People had different expectations of restaurants.  

What do you mean? Give an example from those days.

Like, people expected to be able to tweet at a restaurant and get a reservation. 

Hah! Okay sure, why not.

Or even just people having their phone out at the table, or taking photos. This was real early stuff, but it was changing the way that these businesses worked. You had “tech culture,” you had the Mid-Market neighborhood and all these restaurants opening there. It felt like this really great moment, and the vibe was different than it was in New York. 

My husband worked at Twitter at the time, and he said, “You should start a newsletter. People have been doing newsletters!” So I started one using Gmail and MailChimp and sent it to some friends. A couple friends in the right places sent it to some other people, and it just grew from there. 

Who was the audience back then?

That newsletter was meant for people who understood technology and also loved restaurants. I had come from New York, where it was a hospitality town. I never worked at a New York City restaurant, but I went to a lot of them. 

If you go back and look at the old newsletter, it wasn’t that great. I’ve pulled them down, though I have a personal archive. But it was a collection of really interesting observations about how things were changing because of the internet. Most of that original audience was my friends, who worked in technology and had a basic understanding of how tech worked, and then were just interested in restaurants and how they worked. 

A couple friends had a company that got acquired by OpenTable, and my newsletter became required reading for most of the OpenTable product org because their head of product really liked my writing. So it morphed from there into a resource for the burgeoning restaurant technology industry. 

Restaurant tech is a pretty niche media beat even now, so it must have been practically nonexistent that far back.

Yeah, I was just pulling something out of nothing, I guess. But it really did feel like things were changing in the hospitality industry.

So after you become required reading at OpenTable, did the newsletter suddenly become lucrative?

Oh, it was absolutely not. I was not working a full-time job then—I was contracting with an agency that did social media marketing. I had also just gotten married. Those things are not unrelated. I was able to focus on this work because I loved it. I supplemented by doing some creative work … like, I wrote tweets for a couple of chefs. Then I started to slowly, slowly get some freelance assignments, mostly industry blogs for tech companies, and then a little bit of B2B. I even did some contract marketing work for OpenTable, which was funny because I had to promise I wasn’t going to write about the stuff I heard there. I mean, I wasn’t trying to do heavy journalism and break stories. I was just writing a newsletter I thought was cool. 

What year are we up to, at this point?

This was 2014 or 2015. I was doing the newsletter weekly to keep myself honest because I wanted to do more freelance work. Having a newsletter, once a week for several years, earned pretty decent credibility to get back into magazines, to get back into writing. It was still a slow climb back in. 

In 2016, a friend of a friend connected me with Rafat Ali, the CEO of Skift, a B2B travel media company who was hoping to get into food. They flew me to New York and said, “We’d love to acquire your newsletter.” I was six months pregnant at the time, so I was like, “I can’t do this right now, but yes, we’ll figure it out.” This was in July or August, and they had their big event coming in September. I told them I could commit to this, but I’m not coming on full time until March because I’m having a baby, and I’m going to stay home with her, and then I’ll come in when she’s three months old. 

So Skift essentially paid me to write the newsletter. They “acquired” it at that time, though we hadn’t signed anything. But they paid me as a contractor to continue writing it, and they paid a freelancer to do it while I had the baby. And then I came on as a full-time employee in March 2017, and they officially acquired it. I was given a full-time job with benefits, and essentially a signing bonus where I turned over my original mailing list. 

How long had you been doing the newsletter by then?

Three and a half years.

And how big was your mailing list when you sold it to Skift?

Oh, low four figures. It was intentional growth. My open rate was over 50% at the time. It was built to be a useful and important read. And right when it got acquired, actually, I was on a Fast Company list of newsletters that make you smarter. I almost fell off my chair, I was so excited. It meant that I was creating something that people found valuable, and these weird insights I was pulling out of my own personal experience at the time were resonating.

How did Skift want to incorporate what you were doing into their strategy?

Skift was interested in growing more into the business of restaurants and hospitality. I was brought on to build a restaurant vertical for them. At first, it was just me. Eventually I had a team. It was meant to eventually be as big as travel, if not bigger. 

So what happened?

I did it. I accomplished it. Mission accomplished! It was called Skift Table, and it was about the restaurant industry. It was extremely successful because it was a forward-looking B2B publication. But the thing that got us is that the travel industry and travel tech are extremely different than the restaurant industry in terms of size, and in terms of how much money they have to spend. And there were some legacy B2B media in restaurants that are still there, and very widely read, and didn’t necessarily need to be “disrupted.”

I believed—and I still believe—that we were building a wonderful resource and thinking about things differently. People knocked off our stories all the time. We were approaching hospitality from the lens of technology and the future, and it was really great. It just wasn’t making the kind of money that travel was making for many, many, many reasons that don’t even matter now.  

I only have an outsider’s view of Skift’s business model, but I assume they were trying to sell ads, sponsorships, events, that sort of thing?

Sponsorships, a little bit of ads ... they have a robust sponsored content business with really wonderful content. They do great work. That was the model. But by and large, it was at a level that the hospitality industry wasn’t prepared for at the time. 

How long were you at Skift, all told?

I kind of started in the summer of 2016, and then it ended in May 2019. So it was a roughly three-year engagement, with two and a half of those being full time. 

With the newsletter being part of the Skift Table vertical, was it still going out weekly?

No, we went from weekly to biweekly to daily, and it was very different when it was a daily, with a lot of links to the site. I had a team of three, and a lot of the travel editors came over to pitch stories when they fit into dining hospitality, which was really helpful. The Wednesday newsletter was more longform and analysis. That was my favorite one to write, because it was like the old way. 

So over your time there, how much did the mailing list grow?

There were over 20,000 subscribers at the end, maybe more. 

Wow. So about 10x growth over that period. 

Yeah. Whooo! Ooof. 

Sorry, I know this is a little painful to talk about.

Oh yeah, it’s painful!

Were these paying subscribers or free subscribers? 

We did not have a paid newsletter model. They were all free subscribers. Skift had a marketing team, they had a growth team. They had a lot of things that I don’t have access to now. The open rate remained quite high. It was not 50%, but it was very high. And we got great feedback. 

What happened when it shut down? 

I was in New York when they called me and told me they were done. I got to drink a bunch of champagne and bought plane tickets to London and went to see a friend. I had had a second baby, and she was about five months old when I got laid off. It was rough because I had been working extremely hard to get Skift Table into a place that they wanted, but requirements at home were higher than they had ever been. And as plenty of parents do who are in charge of big projects, when I did have time off, I didn’t enjoy it properly.

I decided to take real time off with my baby because I felt like I had lost some. So I took the whole summer from May through August, and we did some traveling and just spent time with my two girls who were two years old and six months old at the time. 

But the work at Skift felt unfinished for me. There was some talk of giving me back the subscriber list. That never happened for a couple of reasons, and that was a little bit frustrating for me. I still owned the original list though, so I started over. 

I’ve been in the position myself—more times than I care to admit—where a project I felt invested in got shut down, with the employer having no intention to do anything further with it, and yet there never seems much of a path to discuss how such a project might be at least partially released to the care of those involved to take a stab at continuing it independently. I’m curious to know how that conversation went when you left Skift.

The leadership was very aware that Skift Table was essentially my third baby. I cared deeply for it, and I worked my tail off to nurture and grow it. I think their position was like, “We’re not trying to do something terrible to  you. It’s not a viable business for us, but we want you to be able to continue this on your own.” I think it ended up getting stuck in legal terms of service. They gave me some options about how I could access the mailing list, and send the list members a note, and ask them to convert to my new list, which I did one time. I appreciated the offer, and I understand where it came from. Unfortunately, it couldn’t work out the way I wanted it to, and it was not worth fighting to get it. 

That’s unfortunate, but it certainly could have been worse.

It was not an angry departure. I understood why they did it. The company leadership has continued to be supportive—they still tell people, “If you’re looking for the future of dining, call Kristen.” So we don’t hate each other. I am bummed about it, and it hurt, and it sucks. But you can only do what you can do, so felt it was time to cut it off and just start growing again.