Navigating Restaurant Tech’s Roadmaps with Anthony Presley

Isaac Nassimi: Do you go by Anthony or Tony?

Anthony Presley: I think that’s assigned at birth. I’m an Anthony.

Isaac Nassimi: Okay.

Anthony Presley: I respond to a lot of things though, and most of them are worse than Tony.

Isaac Nassimi: All right, Mr. Presley. I did some reading on you and you have fun, unusual roots that got you into this industry in this career track. I saw you started in game development. Can you tell me a little bit about that?

Anthony Presley: I did. Prior to that, I started in game hacking. My dad was stationed in Cairo, Egypt. He was a Navy entomologist and was studying and building vaccines. This was pre-internet, pre-iPad, all dial-up modem stuff. In the summers we’d come back to the States and buy games on floppy disks or CDs, at some point, and I’d take them back. My friends and I would take them from the States back to Cairo and then figure out how to swap them around. There was inevitably some copy protection—“on page three, paragraph six, the third word is…”—and you’d have to fill that in. That’s how they kept you from distributing copies. We figured out how to hack the games and remove the copy protection.

Anthony Presley: Then I got into game development with various engines. I had a very fun seventh grade teacher who was one of the inventors of the Mac OS and he was on sabbatical. His wife was teaching at the school I went to in Cairo. He kept me entertained because there was no TV, no internet, and I was a bored American running around Cairo, Egypt.

Christine Spang: Wow. I’m pretty sure I benefited from some of your cracking early in the days, because I used to download games with the enclosed “we included what you need” to actually make it work.

Anthony Presley: You found it. Yep.

Christine Spang: My folks wouldn’t buy me the latest computer. I just had to use the old family computer which meant you had to find old games that would work on it.

Anthony Presley: Yeah, I get that.

Isaac Nassimi: Did you have a hacker name, Anthony?

Anthony Presley: I didn’t have a hacker name, not that I can recall. That was 30 years ago. Not that I remember.

Isaac Nassimi: Don’t worry, you’re beyond the statute of limitations.

Anthony Presley: It’s true. Nobody’s coming to get me.

Isaac Nassimi: You said you worked on game engines. Can you tell me a little bit more about it? I learned to program by working on games myself and it was a great experience.

Anthony Presley: I would recommend anybody go learn software development on games. The algorithms and technical stuff you have to learn is huge—especially when you think about graphic elements inside a small, resource-constrained computer. Now my iPhone is way more powerful than anything I had at the time. I got into game development and ultimately did demos where you would build a fly-through or fire effects. Doing that on a 16-bit computer—a 286 or 386—was wild. None of them were successful, but my friends and I would play them and tweak them. It made you learn fundamentals that most modern developers coming out of a university don’t know outside of a visual editor.

Isaac Nassimi: That’s awesome. That’s how I got my start as well. You could feel when your code was slow or inefficient. In the web development world today, you have to bring something to massive scale to get that feeling. You have to benchmark it. Everyone should screw around with it. Great experience. What happened after that?

Anthony Presley: I was in college. I’d been a software consultant in high school because I didn’t want to work retail. I joined a software consulting company and we split it up when I went to college. Around my junior year, I had about 60 employees working for me. I realized quickly they did not care about me getting my degree and I didn’t care that much about going to school. So I dropped out and kept on with the software company for a couple of years. It was a good time until my clients did some stupid stuff and got in trouble with the federal government. Then I found out you should have a product and not a consulting company.

Christine Spang: Wow. Did you just say you had 60 employees while also going to college?

Anthony Presley: I did.

Christine Spang: How did things take off so fast?

Anthony Presley: We built custom vertical ERPs for an attorney. He had an advertising agency feeding horrible leads. His cost of acquisition was through the roof. I asked, “If I beat what they’re doing, would you give me your business?” I beat them, picked up all their advertising, and next thing I knew, I had an advertising and media company and we were shooting Super Bowl ads. It was crazy.

Christine Spang: It sounds like you acted with a ton of agency. What made you feel like you could do that in college?

Anthony Presley: I was just dumb. Nobody told me I couldn’t do it, so I tried. That’s one reason I like working with startup incubators—you’ve got young people who don’t know any better. They’re like, “I’m going to run through that wall.” I saw a problem a customer had and thought I’d fix it.

Christine Spang: You mentioned you learned a lesson from building this company where things got crazy in terms of product roadmap. What happened?

Anthony Presley: We started as a services company building for a couple of clients, 1998 to 2006. SaaS wasn’t a thing. I didn’t know you could charge monthly. We billed hours, projects, or milestones. When our main customer—90% of revenue—got in trouble, I went back to the drawing board: diversify revenue, spread it around, don’t have that problem again. So we went to building products.

Isaac Nassimi: What kind of products?

Anthony Presley: We built a warehouse management product for a bit. We partnered and built Smart Crop—little sensors for agriculture to monitor soil temperature, humidity, and water, and tell you when to water. Ultimately we settled on a workforce management product. I didn’t know you could raise VC money. Lubbock, Texas doesn’t have a big VC group. So we built it with services on the side, leveraged SEO, got paying customers. Then they told us why our software was the worst thing on the planet and needed to improve. They provided feedback, and we did.

Isaac Nassimi: Smart Crop sounds really cool and ahead of its time.

Anthony Presley: Very much so. Making hardware is expensive. That partner burned a lot of cash building circuit boards.

Isaac Nassimi: Software lets you ship changes daily and build the airplane while it’s in the air. Tell me what happened after that.

Anthony Presley: We grew and learned. We thought we had the coolest idea: automatic scheduling where a manager sits down and a pre-built schedule is done. We showed customers and they said, “We pay our managers to build schedules. I don’t know why we would also pay you.” That’s what we heard in 2007 and 2008. So we asked what they needed and they said, “HR compliance, clock enforcement,” and more. We built those things and got customers in restaurant and grocery.

Anthony Presley: Seven or eight years later we raised a Series A. We got yelled at in our first board meeting because we didn’t grow fast enough. We couldn’t spend the money fast enough. We scaled, ultimately sold the company in 2016, then worked for the strategic acquirer for four years and did nine M&As.

Anthony Presley: In 2020 we spun the company back out. After that I went to Custom Business Solutions where we make software for restaurants and places that sell food. I still run a workforce management SaaS company as well.

Christine Spang: So this is your second restaurant industry business?

Anthony Presley: Second—or third. I worked for Truno. We serviced and supported pretty much every grocery chain in North America.

Christine Spang: What drew you to the restaurant business?

Anthony Presley: It’s low margin, high turnover. What I like most is that operators are going to operate. You’ve been to restaurants on a Friday night where something breaks and you don’t know it broke because whoever’s running it figures out how to make it work. The gumption of everybody in the industry is appealing.

Anthony Presley: In the kitchen, half the pizza line may be broken, the grill may not work, they may run out of tomatoes, half the staff called out sick, your favorite vodka isn’t there—yet they still smile and bring you your food and hope you tip.

Isaac Nassimi: In software the worst thing is an exception—return a 500. You can’t do that in real life. You can’t kick all the customers out. Building software flexible enough to handle exceptions is hard. How did you get to the point you could handle those edge cases?

Anthony Presley: You’re correct. In software, short of hospitals or pacemakers, the bad thing is the page doesn’t load. In B2B SaaS, if it’s down for a day, the buyer comes back tomorrow. In restaurants, if you’re hungry at lunchtime on Friday and it’s down, that revenue is gone. No do-over. I’d love to say there’s a silver bullet, but it’s grit and being around a long time.

Anthony Presley: CBS has been around 30 years. Art and Jeremy Julian started it 31 years ago. There’s blood, sweat, and tears in solving Friday night problems—failover for printers, what happens when the kitchen display doesn’t work. We’ve spread to about 11,000 restaurants and they always come up with new ways to break software. There are always new integrations. We have 100+ now. ISV partners find ways to break things too. It’s constant guardrails to minimize disruption from third parties.

Christine Spang: I identify with that. At Nylas, unified API for email has endless long-tail exceptions. We still find new edge cases after 10 years. People buy platforms because you’ve accumulated expertise and learned the hard way.

Anthony Presley: Yeah. I’m curious—being around for 12 years, what have you learned that you wouldn’t know if you started over tomorrow?

Christine Spang: A hundred thousand things. First: the best way to avoid dying is to not give up. You keep showing up every day and solving the next problem. That’s what leads to success eventually.

Christine Spang: Things changed: LLMs barely existed 12 years ago. It was the golden age of SaaS. We’re a developer platform. There are best practices now for being an API provider that didn’t exist then.

Christine Spang: I’d love to understand the restaurant software ecosystem. I read your website. You have SaaS pieces. Do you ship hardware or integrate with it? What do you have to integrate with?

Anthony Presley: It’s difficult. I don’t know if it’s more difficult to sell to restaurant folks or developers. Developers say, “I can build that.” Restaurant people generally don’t pick up the phone.

Christine Spang: Developers don’t either. They hate picking up the phone.

Isaac Nassimi: Who knew these two groups had so much overlap?

Anthony Presley: There is a lot of overlap. The hard part is payments rails. In restaurants, four or five processors own the market. They certify hardware. There are PCI levels depending on volume. Devices differ for table service, drive-thru, counter. That drives platform constraints: iOS, web, Windows, Android. You can’t just pick one processor and one device.

Anthony Presley: You have enterprise contracts and SMB contracts. Hardware “free” can become a huge cost if you exit early. Gateways add flexibility but take a percentage. Other countries with regulated credit cards get more standardization.

Isaac Nassimi: I worked at an Italian restaurant using Aloha. It felt dated. Everyone thought eventually we’d use iPads. What drove adoption?

Anthony Presley: NCR/Aloha had massive penetration. About 15 years ago our founder said nobody was calling about DOS anymore. Before iPad1 we built for Macromedia Flash. Then iPad1 came out. Apple fronted us money to put a POS on iPad and we were the first POS on an iPad.

Anthony Presley: Market maturity took time: hardening devices, drop resistance, liquid resistance, Wi-Fi reliability, heat lamps. Restaurants are crazy environments. Hardware matured and guest comfort matured. Toast’s handheld devices are common now, but tipping while the server stands there is still awkward.

Isaac Nassimi: What do you think the dining experience looks like in 10 years?

Anthony Presley: A lot of work is going into getting guests back. CDPs and one-to-one marketing will push offers. If brands get what they want, RIP inboxes. Many won’t execute well.

Anthony Presley: We released a patented product around AI predicting when food will be ready. COVID brought online ordering and third-party delivery, competing with dine-in. It can slow down dining. Systems aren’t unified. If you’ve seen The Bear, it’s real. Smarter systems—sometimes basic ML—can track kitchen state for a smoother experience. Operators often don’t know what’s going on right now.

Christine Spang: How do you think about using the data you’ve aggregated to make the platform better?

Anthony Presley: In general tech, open APIs exist. In restaurant tech, it’s closed. Specs can be unavailable. There are no data standards. That makes migrations and interoperability hard.

Anthony Presley: A POS is essentially an ERP for a restaurant. It generates customer interactions, ticket items, payment tokens, reorders. We have an open API—your data is yours. Customers build all kinds of things on top—moving data, kitchen timing, drive-thru timers. We encourage it.

Christine Spang: That’s amazing. You’re creating the de facto RFC for restaurant data.

Anthony Presley: Unintentionally. From a tech background, it shouldn’t be this hard, but it is.

Christine Spang: How is AI empowering non-technical people changing what they can build with your platform?

Anthony Presley: We’re exploring no-code/low-code talking to API endpoints. We’ve been playing with Lovable.dev. Some customers use it to interact with our APIs.

Anthony Presley: Most POS users are 18–30 and not highly technical. They want a button that says: “This is Anthony’s favorite dish, birthday, last orders,” to make their life easier—not necessarily build tools.

Isaac Nassimi: People buy software if it increases enterprise value—more customers, happier customers, more spend, more repeat visits. Surfacing customer context is like a sales rep checking the CRM before a call.

Anthony Presley: Hospitality is being hospitable. Bring data to the average worker. Millions of workers, on average not technical, so tech must meet them where they are to drive enterprise value—upsells like desserts, margaritas, fries—with data.

Isaac Nassimi: Do you think restaurants become less personal, like touchless hotels? Will people order without talking?

Anthony Presley: Preferences vary. There’s room for high-touch and low-touch. Some customers put pizza-making robots in Walmart—kiosk order, robot makes pizza, no interaction. On the opposite end, fast hospitality-centric brands like In-N-Out are quick and transactional.

Christine Spang: I ordered lunch on an iPad yesterday with someone behind the glass and I wanted to talk to them. I’m not ready for the kiosk future.

Christine Spang: How have restaurant desires for tech changed? Would scheduling sell today?

Anthony Presley: Software counts have exploded everywhere. Enterprises use dozens to hundreds of tools. Restaurants and retail mirror it. All-in-one is a sledgehammer; best-of-breed adds dozens more. Managers end up managing 30–50 tools.

Anthony Presley: Scheduling is more important now. Hiring and retention are hard. You need preferences, overtime, labor law compliance. We don’t struggle to sell scheduling anymore. People want scheduling, compliance, HR, and more. Are you seeing the same in other verticals?

Christine Spang: Yes. Competition exploded, barriers to entry dropped, and AI tools speed up experimentation. Also, platforms consolidate: best-in-class starts standalone, then leaders bundle features so data is connected.

Isaac Nassimi: Companies consolidate vendor lists due to budget, overwhelm, compliance, and security. Tools try to become the hub so they’re uncuttable.

Anthony Presley: That’s happening in food too. Rudy’s is barbecue plus grocery plus fuel. Buc-ee’s blends everything. Platforms try to be the hub so they don’t get cut.

Isaac Nassimi: Let’s do Picks—something you’re excited about. My pick is a stick with an alligator clip to help clasp bracelets. Five bucks, saves five minutes.

Anthony Presley: Love it.

Isaac Nassimi: Spang, what have you got?

Christine Spang: A pizza-shaped floaty. You can get eight slice floaties that connect together. I bought the whole pizza and gave one slice to eight friends. I’m excited for a pizza party on a lake.

Anthony Presley: That’s pretty awesome.

Isaac Nassimi: Very proud—you have four times the national average number of friends.

Isaac Nassimi: Anthony, do you have a pick?

Anthony Presley: Lovable.dev. It’s super fun and frustrating. Being able to chat with essentially a product designer that can build what I want has been awesome. It produces reasonable code.

Isaac Nassimi: That’s awesome.

Christine Spang: Busy execs are grateful for AI coding tools. It allows you to ship something in the time that you have.

Isaac Nassimi: You think you’re good at delegation until you use one of these AI coding tools.

Anthony Presley: You think you give good product direction, and you don’t. My trick is to keep ChatGPT handy, have it write product specs, then dump that into Lovable.

Isaac Nassimi: You automated the whole stack.

Anthony Presley: A little bit.

Isaac Nassimi: That puts us at time. Thank you so much, Anthony, for joining us and telling us about the past, present, and future of the restaurant world.

Anthony Presley: Thanks for having me. This has been fun.