00:00:00 – Xavier Mariezcurrena:
Welcome to the 86 Reason podcast. I’m here with Anthony Pressley of TimeForge. You have an interesting story and an interesting business. The first time I met you in Las Vegas, I was struck by how calm, cool, and collected you were. After getting to know you, I’ve really appreciated the path you’ve taken building your business.
00:00:43 – Xavier Mariezcurrena:
I’m happy to have you on. Welcome. How’s life? Where are you these days?
00:00:43 – Anthony Pressley:
Thanks for having me. Life is great. I can’t complain. I stopped complaining long ago. I’m in Fort Worth. I just got back from a restaurant trade show and I’m trying to catch up—work never stops.
00:01:09 – Xavier Mariezcurrena:
I’m starting to recognize there’s a steady crew of “show vets.” You do a great job getting out there. Are shows about building relationships for later, or is it mixed?
00:01:59 – Anthony Pressley:
It’s a mixed bag. Some shows are great and some aren’t. It depends on who attends. If you think about the total addressable market in restaurants, independents don’t often hop on a plane for a national show. They’ll go to something local. As you move up into larger organizations, you see the same leaders over and over. You build relationships. But it’s very rare someone runs up at a trade show and buys restaurant tech on the spot. When they have a need, they might call you. That’s the point.
00:03:19 – Xavier Mariezcurrena:
Let’s start at the top. Are you a lifelong technologist? Did you ever work in restaurants?
00:03:39 – Anthony Pressley:
I regret that I never worked in a restaurant. I’ve helped friends—driven people to shifts, helped take out trash—but I never worked in one. I took the technology path.
00:04:41 – Xavier Mariezcurrena:
How did you get into tech? Video games? DOS? How did it come together?
00:05:01 – Anthony Pressley:
My dad was in the Navy. He was deployed to Cairo, Egypt. We lived there, and I went to Cairo American College. In sixth grade I took a computer class with an Apple computer. The school brought in an Apple Fellow—one of the original inventors of the Macintosh—who taught me to program. In the summers we’d fly back to the States and I’d buy computer games. Back in Cairo we had no internet, no satellite TV—bored kids. The games had copy protection, so we’d hack them so everyone could play. That’s how I got into computers. By 1996–97 I was deep into tech.
00:07:30 – Xavier Mariezcurrena:
How long were you in Cairo?
00:07:30 – Anthony Pressley:
A little over three years. We also spent time in Frankfurt.
00:07:56 – Xavier Mariezcurrena:
Did you pick up any Arabic?
00:07:56 – Anthony Pressley:
Yes. I was fluent when I left. Then I didn’t speak it for decades. Now I only remember a little.
00:08:37 – Xavier Mariezcurrena:
Cairo is beautiful but chaotic. Did that hit you as a kid?
00:09:10 – Anthony Pressley:
For sure. Like all big cities, there are wealthy areas and very poor parts. There are huge discrepancies. It’s a different world.
00:10:31 – Xavier Mariezcurrena:
When you came back to the U.S., did you study technology formally, or were you already ahead of the curve?
00:10:57 – Anthony Pressley:
When I turned 16, my dad told me to get a job. My school had a Valentine’s Day dance, and I proposed writing software to match boys and girls into couples. This was 1997. I basically built “Match.com” for a school dance. The school paid me, and I was proud. My dad said, “That’s one-time money. Get a real job.”
00:12:05 – Xavier Mariezcurrena:
Did you rig the algorithm for yourself?
00:12:05 – Anthony Pressley:
It’s amazing how the algorithm works, right?
00:12:50 – Anthony Pressley:
A slightly older student saw what I built. He was interning at a software company and introduced me to his boss. That was my first lesson in networking. I got a software job at 16 in Northern Virginia. We did networks and software. The owner billed customers $50/hour and paid high school kids about $9/hour—he made the spread. There were five or ten of us.
00:14:11 – Anthony Pressley:
When I went to college, that business wound down, and I took a customer with me. I had a software company and one customer, then scaled it to 60 employees by my sophomore year.
00:14:32 – Xavier Mariezcurrena:
Did you ever think, “Why am I in college?”
00:14:32 – Anthony Pressley:
My junior year was basically the end of college for me. I kept going for health insurance—$50 a month.
00:15:39 – Xavier Mariezcurrena:
Tech changes so fast. How do you keep up—do you chase trends or let the market decide?
00:16:17 – Anthony Pressley:
I like hard problems. I like seeing how other industries solved them. Restaurants are often laggards in tech. I’ll look at retail, healthcare, and volunteer with entrepreneurs in other industries. That gives me ideas for what to bring into restaurant labor.
00:18:15 – Xavier Mariezcurrena:
A lot of technologists can’t sell. Did you have that gift or develop it?
00:18:46 – Anthony Pressley:
When I was younger, I wasn’t very smart. I didn’t know I “should hire a sales guy.” I built the product, so I thought I should sell it. People ask why we bootstrapped—I didn’t know raising money was a thing. I’m happy at trade shows and talking to people, but I’m bad at outbound. I love relationships. I see myself more as a product owner—see the problem, know enough tech to fix it, learn enough sales to survive.
00:22:33 – Anthony Pressley:
Since COVID, trade show relationships have become real friendships—vendors and operators. It takes time to build relationships.
00:23:18 – Xavier Mariezcurrena:
What industries have you worked in, and when did restaurants happen?
00:23:52 – Anthony Pressley:
We built ERP/CRM software for attorneys. We did work with Rockwell International that became Boeing—stealth ship modeling, ray tracing, design. I built a warehouse management system for diabetes companies and learned supply chain and medical billing.
00:25:13 – Anthony Pressley:
The idea for TimeForge goes back to college. My roommate’s uncle owned a restaurant with one phone line. Staff couldn’t call because it would tie up the line. He posted schedules Sunday night and employees had to drive in to see if they worked Monday. In 1999 we thought it was ridiculous and brainstormed a better way. I shelved it until 2006 when a friend with a restaurant said they still did schedules that way. I threw an intern on it for a summer, and that’s how we got into the space.
00:27:35 – Xavier Mariezcurrena:
What was your first onboarding like? Was the learning curve shocking?
00:28:04 – Anthony Pressley:
We built an automated scheduler—manager sits down and the schedule is basically there. Other industries like hospitals had this for a long time because regulations are complex and stakes are high. In restaurants, if staffing is wrong, you hurt profit and operations, but the stakes are different.
00:29:15 – Anthony Pressley:
We launched in 2007. I thought we could put it online and people would just use it. Our first customer installed it and called the next day with ten things that were wrong. He basically said if I didn’t fix them before the next billing cycle, he was gone. We worked nonstop.
00:30:23 – Anthony Pressley:
My mom introduced me to the founder of a large Mexican restaurant group. I demoed the product and he said, “I pay my managers to build schedules. I don’t know why I’d pay you.” That objection shocked me. I’ve heard it a thousand times—and still hear it in 2025.
00:32:09 – Xavier Mariezcurrena:
What would you say now?
00:32:34 – Anthony Pressley:
Now I’d talk about turnover, burnout, and what managers could do with their time instead of chasing sticky notes, emails, and texts. There’s this expectation that managers work 80 hours a week and do everything—marketing, ops, tech, repairs, therapy for staff, dealing with customers. I’d be prepared for that conversation now.
00:33:48 – Xavier Mariezcurrena:
How long before you felt like you had a real process and momentum?
00:34:54 – Anthony Pressley:
We had a services company on the side building custom software. We grew the product slowly. We didn’t shut off services until around 2012–2013. This is measured in years.
00:35:30 – Xavier Mariezcurrena:
(Xavier shares his own founder journey, pushback, slow traction, and the reality of refactoring and ongoing maintenance in software.)
00:42:11 – Xavier Mariezcurrena:
By 2013, what kinds of restaurants were you succeeding with?
00:42:11 – Anthony Pressley:
We built scheduling and almost no one used it. We asked customers what problems they had. The issues were enforcing schedules, compliance, legal and HR problems. We started building for complex restaurant groups—multi-venue, nontraditional operations like zoos, museums, theme parks—transient workforces. We often said: if you can write your schedule on a napkin, you don’t need us. We focused on complexity: multi-state operators dealing with different overtime laws. Then we found similar complexity in grocery and convenience stores doing prepared foods.
00:44:43 – Xavier Mariezcurrena:
How different is selling into grocery versus restaurants?
00:46:18 – Anthony Pressley:
Restaurants have a wide range: independents, hotels, franchises, big groups—different buyers and implementations. Grocery is interesting: there are about 42,000 grocery stores in the U.S., versus hundreds of thousands of restaurants. That means far fewer decision-makers. Many grocers are multi-generation family-owned. Change management is harder—they may have never done it differently.
00:47:55 – Anthony Pressley:
The scale is different. A 20-store grocery chain we service is a $1.2B business—about $1M a week per store—with salad bars, prepared foods, and everything else. Grocery is extremely relationship-driven. In tech: first year at a show they smile. Second year: “You’re still here.” Third year: “What do you do again?” Fourth year: “I think we need what you have.”
00:49:14 – Xavier Mariezcurrena:
(Xavier shares a 10-year sales cycle example.)
00:49:43 – Xavier Mariezcurrena:
You’ve bootstrapped, right?
00:50:11 – Anthony Pressley:
Yes and no. In 2014, a partner (HotSchedules) said they’d bring a publicly traded large customer—and the rollout could kill us. Too much business can be a problem if you can’t consume it. I raised a Series D, used it to hire and scale, and we landed Sprouts Farmers Market—48,000 employees on the platform.
00:52:33 – Xavier Mariezcurrena:
What are the benefits and risks of raising money?
00:52:58 – Anthony Pressley:
Barriers to building software are lower now. Back in 2007, taking credit cards online was complicated and expensive. Today you can be up quickly with Stripe or others. My opinion: if it’s software and you don’t need to build something physical, don’t raise until you have a repeatable process. Money should be gasoline on a fire, not a tool to figure out what you’re doing. Raise for a land grab only if you know how to execute.
00:55:23 – Anthony Pressley:
I bought a company last year that raised $12M and “almost worked,” then went out of business. Raising also means you have a boss. Entrepreneurs often start to avoid having a boss—then you raise and you must return money 5x, 10x, 20x. That’s pressure.
00:56:57 – Xavier Mariezcurrena:
Do you still have moments of doubt?
00:57:19 – Anthony Pressley:
I don’t think that ever goes away. You can rationalize it—“this too shall pass.” Competitors raise huge rounds, the macro economy shifts, tariffs, uncertainty. There’s always something. But change takes time. Competitors eating your lunch takes time. Your business falling apart usually takes time too. It’s rarely an instant “everyone leaves” moment.
01:00:15 – Xavier Mariezcurrena:
We’ve had blockchain, machine learning, now AI. Is AI here to stay, or will it be replaced by the next marketing term?
01:01:03 – Anthony Pressley:
I was at conferences recently and spent a day with an AI expert. AI isn’t new; what’s new is packaging and accessibility. He said: if you view it as software, you miss the point. Think of AI as a job. If you can define a job description and processes, then you can give that to an AI agent—assuming you give it good enough data. Data quality is the big asterisk. You’ll never have perfect data because people aren’t perfect. Humans can notice and fix errors on the fly; AI may not. He also said: the worst AI will ever be is right now—it will only improve.
01:04:29 – Xavier Mariezcurrena:
(Xavier shares examples of AI giving wrong information, like recommending a “best brunch” that only happened once years ago. Emphasizes “garbage in, garbage out,” and says AI works best in closed, well-defined problems like scheduling.)
01:07:34 – Xavier Mariezcurrena:
What’s your guilty-pleasure celebration meal? How did you celebrate Sprouts?
01:08:02 – Anthony Pressley:
We didn’t celebrate until the full rollout was complete. Then we took the team out to a steakhouse in Lubbock (a place that doesn’t exist anymore, but it was the nicest spot in town). Next show together: DC in November, then Vegas.
01:09:11 – Xavier Mariezcurrena:
We’re in Bogotá. We like to gift guests coffee and chocolate. Do you have a preference?
01:09:32 – Anthony Pressley:
I drink coffee if it tastes like chocolate. I like a Snickers bar in my coffee.
01:10:20 – Xavier Mariezcurrena:
How can people find you?
01:10:20 – Anthony Pressley:
Type “Anthony Pressley” into Google—you’ll find me. Connect on LinkedIn. Our website is timeforge.com.
01:10:38 – Xavier Mariezcurrena:
Thanks for joining us, Anthony.
