Expedite's Kristen Hawley on the Rise of Restaurant Tech
Rebuilding a newsletter focused on one of the newest industries in technology.
publishes restaurant technology newsletter , the latest incarnation of a beat she’s cornered both independently and in-house during a previous stint at travel media company Skift. This is Part 2 of a two-part interview—read Part 1 over on .
When did you decide to relaunch your restaurant technology newsletter on Substack?
I originally relaunched it on Mailchimp back in September 2019. I had heard about Substack, though I was concerned about the limited branding you could do on your newsletter. It still is pretty limited, and I tell them that all the time. But I went ahead and moved over to Substack in late 2019 or early 2020.
Had you worked out an approach to making it a paid newsletter, or partially so?
I wasn’t sure what I was going to do. The idea of paying for a newsletter was still pretty new. And moving was still technically tricky. In the time I worked at Skift, restaurant technology became a beat. It became a popular topic, and it became an industry with so many players and startups and established companies. I was proud of the work that I had done, and I wanted to keep doing it. I was like, “Look, no one is better than me at covering this, and I want to keep going. I’m not done.”
What did you want to differently on your own?
When I was working at Skift, we had branched out into covering not just technology, but also franchises, and corporate restaurant groups, and tons of earnings calls, and other things that mattered to the restaurant industry at large. I just didn’t have the time or attention to do those. I felt they were covered pretty extensively by other places in B2B media. I wanted to get back to my roots and be the tech person.
That was really fun, because now—as opposed to when I started in 2013—it had become an extremely established industry with a huge number of people working in it, and established players, and companies were IPOing. It was really exciting because all of these things that were bubbling up in the early 2010s were actually happening now. All the stuff we had predicted was happening—a period of changing everything. So it was really wonderful to be back on my own, to be able to explore other things untethered to advertisers and numbers and events.
It’s hard to talk about this though without being very clear that I am privileged to have a successful partner who works in technology. And I was able to take the time to build something that I found valuable without worrying about monetizing it. I was also freelancing at the time, but I would not have been able to do it without my husband’s support.
What made you choose to try Substack versus another platform?
They made it so easy to monetize. But truly the real reason is I knew people were getting deals from them. They were giving them cash to build newsletters that they thought would be successful. And I firmly believed—and still firmly believe—that Expedite could go big, and deserves to be on their radar.
It took some time for me to get it there. It was about a year after I moved over to Substack that they opened the food fellowship program. I decided to do it because, one, I saw them supporting these other creators in a way that I had never seen before. And two, because I was like, well, people tell me that this is valuable, so perhaps I can make some money on it.
What was the fellowship experience like?
The people in my cohort, they’re all phenomenal. That was the best part. You meet all these people who, like most of us, work in a vacuum, and you’re like, “Oh my gosh, we have people to talk to! We have a Slack channel!” I think everyone tried to follow the advice they were giving us to the letter because we’re like, “Just tell us what to do and we’ll do it because we want to be making money.”
“I think everyone tried to follow the advice they were giving us to the letter because we’re like, ‘Just tell us what to do and we’ll do it because we want to be making money.’”
But week after week, we were coming back to their team and saying this isn’t working, or not working well enough, or not working fast enough. And the response was, “Keep at it, it’s a slow build.” But at the same time, you hear stories of so-and-so making six or seven figures on Substack. There’s a huge discrepancy about where we are, and where these people are who Substack identifies as the future of the platform. And they’re just telling us to keep going, but we’re telling them it’s not working. That was frustrating for many of us.
Substack always seems to be struggling with these disconnects when it comes to creator relationships—they are or are not a publisher, they offer financial support in various ways in a somewhat arbitrary manner, their advice on growth seems to come from emulating top earners rather than cultivating a successful middle stratum, and so on. But I guess if the secret to success on the platform was that easy and universally applicable, they’d tell everyone, everyone would do it, and everyone would make lots of money.
I think that’s really the thing, truly. Substack is very open to criticism, which is why I’m happy to say all this very publicly. But I want to run a business. I don’t believe I am a phenomenally great writer whose art deserves to be supported. I know that I have observations and information that people should pay for because it will help them do their jobs better. And that is a viable reason to be on Substack.
What gets a little bit lost is if I’m running a business on Substack, what I need as a creative is business support. I don’t necessarily need to be told that I am a great writer. Tell me how to get in front of more people. Tell me how to get in the press. Tell me how to go viral, or tell me how I can work with other newsletter writers on Substack. It’s really hard to do that. I do a podcast with another Substack writer. I guest-write for other Substack people, and we want to do more of that.
Why do you think they don’t invest more in this kind of support?
I mean, I’ve heard what their answer is. I don’t want to blow it up.
Okay then I’ll go first. My theory is that all these things we’re talking about are not great for the profit margin of a tech company, which is mostly what Substack purports to be. Business support, audience development, marketing—these are topics that make tech executives’ eyes roll back in their heads. They don’t want to hear about this kind of stuff.
Yeah, there was an article about that—maybe it was in that New York Times newsletter piece—that mentioned somebody leaving Substack, and their reasoning was they wanted to be a business or a brand, and they’ve outgrown Substack. That is an extremely real and logical reason, and it’s one I understand. Because when I ask for things like branded support, or a custom content email, the response from Substack is, one, that’s really hard to do technically, and two, we don’t want to be a marketing company.
Ideally there would be more of a balance there. I don’t love that my newsletter has to look like everyone else’s newsletter, especially when they’re platforming people that I find problematic. My husband worked at Twitter and I worked there briefly in the comms department. It was back when Twitter was like, “We’re not a media company!” But you are. You are! So I’ve seen this happen.
Another disconnect I see within Substack—and this is not unique to them, at all—is they seem to sincerely embrace ideals that make them behave like a publisher, but they don’t want the responsibility-baggage that implies. And as you say they don’t want to be in marketing. Yet being good at all those things would serve their business positively as at actually operates, versus how they prefer to describe it. The terror of message confusion, of defining Substack by what it is not despite evidence to the contrary, seems like a needless conflict and distraction.
It’s funny because there’s so much talent on the platform, and if they would just help us rise, if they could lift up people like me that have several thousand extremely engaged subscribers—and growing, I’m straight up and to the right consistently. They gave me $10,000 and some support, and that’s great! Keep going! Keep throwing money at me, but also, listen to my feedback, and build those things into the product.
I think Substack has gotten better at it, and I see good things coming. But there’s no ideal newsletter platform. I’ve looked at all of them, and I get pitched on them all the time.
Given that you worked the restaurant tech beat independently, and then in-house at Skift, and now independent again—all while the industry itself evolved quite a bit—who do you consider your audience, now?
This is actually a big learning that I took out of the fellowship program. I desperately wanted my audience to be restaurant operators and next-generation restaurant leaders. But those people do not have time to read a weekly or biweekly newsletter. Substack doesn’t have robust analytics tools right now, but you can figure out who your audience is by looking through the list. The bulk of my subscribers are people who work in restaurant technology. And so what I can offer them is a newsletter that is about them—because everybody wants to read about themselves—but also brings humanity and hospitality back into the business.
Because when you’re sitting there working at DoorDash or Resy or OpenTable, and you’re working on all these metrics and products and technology that you know in your heart will make restaurants better, you sort of forget that this is a whole industry that’s been around for centuries operating on its own. You can’t just come in and “fix” it. So I’m trying to bring the reality of restaurant operations and hospitality to people who work in restaurant tech.
What are restaurant tech startups focusing on now?
What’s telling is that so many companies launch wanting to help independent restaurants, then they pivot to work with small and mid-size chains, and then they have to sign on a huge partner in order to fund their growth. This is exactly how the delivery industry was built. Uber Eats would not be as big as it is if they hadn’t signed McDonald’s extremely early as an exclusive partner.
“What’s telling is that so many companies launch wanting to help independent restaurants, then they pivot to work with small and mid-size chains, and then they have to sign on a huge partner in order to fund their growth.”
There are people building technology for independent restaurants, and it’s a great industry. But if you don’t have a huge addressable market, you’re not going to get the big venture funding, because the growth and the return isn’t where investors want it to be.
Tech investors must be horrified at the typical profit margins in hospitality.
I have a restaurateur friend who went through Y Combinator with a product that helps independent restaurants, and people were constantly saying, “Why are you doing that? This terrible business is never going to fly.” But you do hear about plenty of companies launching with the value proposition of giving an independent restaurant access to the same technology that chain restaurants have.
What’s your plan with Expedite going forward?
I relaunched Expedite in September with a new design, and a new cadence—I’m doing it twice a week now, one of which is behind the paywall. I got some advice from some great tech newsletter writers on Substack, and they universally say to put it all behind a paywall. That’s very hard for me to do because my paid audience is a fraction of my free audience. I’m giving myself until the end of the year, or maybe until the spring, to make sure that growth is sustainable.
What’s your ratio of paid to free subscribers now?
My paid subscriptions are about 10% of unpaid, which is standard. I don’t look at conversion rates per email, though my interview with Ben Leventhal had an insane conversion rate when I put half of it behind the paywall. I don’t know if it was because it was Ben or because it was a good interview. Probably because it was Ben. But I was shocked by that number, and I didn’t get any pushback for sending a paywalled newsletter to people, which I was also shocked about. Most people say that when you send newsletters that are only free up to a point, you get crazy unsubscribes.
I feel like putting part of a story behind a paywall has become so common it would barely register with me as a possible negative thing.
It’s very much something you want to do because it converts, but it is hard for a lot of independent creators to do because you get extremely targeted, negative feedback. But I think most people get more conversions than they do unsubscribes, and the wisdom there is like, let them go. I try not to look at my unsubscribes because it hurts, but it also doesn’t matter.
How do you approach investing your time and energy in the paid stuff versus the free stuff? What goes where?
This is another thing I learned from the fellowship program. Anything that’s a big idea of my own, or like a big analysis, or anything that can go viral—anything that could catch on—should be free. I really thought about that in the opposite way. I want to protect my thoughts! People follow me because they believe that I have good advice, so therefore I should paywall my thoughts.
But several people in my cohort said I should do it the other way. I do paywall it on the website, but you can always click through from your inbox and and see the stories. The things that are paid are columns, advice, women in restaurant technology, or stories about how restaurants work—stories that go deeper into the topics I’m talking about. This was definitely a counterintuitive strategy to what I had believed, but I think it’s the right one.
You’re presuming that’s the kind of content an industry audience might shell out for?
Yes. And I’m still in a growth phase. I do a lot of speaking and moderating at conferences, and the feedback I get is overwhelmingly, “Your stuff is great, I wish I had found it sooner.” I don’t know what else I can do! I’m writing for Food & Wine, and Bon Appétit, and the San Francisco Chronicle, and I’m getting links in Eater, and including links to the newsletter in every single piece I do, and I’m on the news.
This is not my strategy for Expedite forever. But for right now, the things that are free are the kinds of things that will attract new readers. And once they are interested in the topic, then the more in-depth pieces are the things that they should be paying for.
So what’s the overall goal with Expedite, if you can think that for ahead?
Oh, man. If it could be like 50% of the salary that I need in order to be a productive member of my family, that would be great. And right now, it’s probably 20%. It’s getting there, but it’s very slow. Am I going to keep doing this forever? I have no idea. Would I sell it again? Yeah, probably. I don’t think I would do the same thing I did last time. I think I would either sell it to a technology company and join them, assuming it’s a company I believe in. Or, if it was a publication, I’d be like, “I built this baby, and you can have it. For a price.”
Read Part 1 of this interview at.