Creating personal software: Plaid’s founding designer Al Hertz on designing for hospitality

“Building a startup is exactly as hard as people say—and 10x more fun.”

Aug 14, 2025

Al Hertz didn’t set out to build enterprise software. He started by designing posters for his band. But looking back, there’s been a consistent thread: building tools that help disparate systems work together—first for musicians, then developers at Plaid, and now hospitality teams at Folio.

Today, Al is co-founder and head of design at Folio, a supplier management platform that’s raised a Series A to help hotels operate with less friction and more soul. Unlike most B2B software, Folio feels delightfully human, complete with satisfying sounds when you reorder inventory and drag-and-drop interfaces that just make sense.

In our conversation, Al shares how six years at Plaid taught him to make incompatible systems work together, why hospitality and design share the same DNA, why the best co-founder relationships develop over years of working together, and how small teams can use AI tools like Cursor to punch above their weight.

🗓️ Heads up: We’re hosting a virtual session on Thursday, August 28 on how startups can find, attract, and win over great designers. We’ll share what’s changed with the talent market in 2025, with tips and examples for founders and hiring managers alike. RSVP here.

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Key takeaways from the conversation

Map your career backwards to find your throughline forward. The path to becoming a designer founder is rarely linear. Look back at your past career decisions, like Al did, to gain a better understanding of what drives you—then build your next venture around that core thread.
Learn by embedding yourself in a startup early on. You don’t have to go all-in on starting your own company right away. Finding a job at an early-stage company and experiencing hypergrowth firsthand provides invaluable insights you can apply when you launch your own venture.
The best co-founder might be someone you already know. Like Al and his co-founder Kate, growing a relationship over years gives you insight into how someone thinks under pressure. Look for overlapping interests and complementary strengths in people you genuinely enjoy working with.
B2B software can and should be delightful. Just because your customers are professionals doesn’t mean your product should be boring. Small details, like drag-and-drop reordering, subtle animations, or context-aware guidance, make enterprise software feel more human and memorable.
Use AI as a force multiplier. Startups can adopt AI tools faster than large companies. Tools like Cursor let small teams punch above their weight and prototype/ship quickly.

How did you become a designer?

I wanted to be a musician first. My small high school in Pennsylvania had computers with Adobe Illustrator, and I got hooked when I realized I could make my musical pursuits seem way more legit if I made posters, album artwork, and websites for them.

It became obvious to people in my circles that I was good at it, so I started getting asked to do projects for others. I’d say yes to random things, like building a website even though I had no idea how to write PHP. That’s how I learned.

The breakthrough moment was around 2012 when I started working with musicians like Lee Martin on projects that used new APIs in creative ways. We created this experience for a Swedish band called Little Dragon where you’d go to a website that said, “Little Dragon has something very important to tell you but they forgot your phone number.” After you entered it, it would trigger a video of the band picking up the phone, timed perfectly to when your actual phone would ring so you could hear their new song. We were recreating the intimacy of playing songs to friends over the phone.

That’s when I became hooked on capital-D design—building software that makes people feel genuinely connected to something.

Where it all began: blending graphic design, digital art, and music.

Looking back at your design journey, from Gumroad to Plaid, what’s the throughline?

Looking back, there’s been a consistent thread: building technology that empowers creative acts. Before Gumroad, it was about celebrating musicians. At Gumroad, the definition widened to all kinds of creators. With Plaid, it took a left turn to focus on developers building financial software. And now with Folio, it’s come back around to what I call “the mother art”: I love hotels and want to serve them.

One great thing I learned at Plaid is: how do you build software that makes other things in software more interoperable, especially when those things might not want to be? The financial system, especially in the United States, is not something that’s inherently open. That’s something I really wa

nted to play with, technologically speaking.

How did you decide on hospitality for Folio?

I needed to do at least two out of three things, with the third coming into sharper focus as we build:

First, I wanted something that played to my unique strengths. Specifically, making incompatible systems work together seamlessly.

Second, I realized I can work on something for years if I love who I’m working with and who I’m working for. The people working in hospitality clearly deserve great software. The nature of hospitality is service, but the people providing it aren’t getting the service they deserve from their tools.

Third—and this is the most important—hospitality is really the same as great design. I’m paraphrasing Danny Meyer from Setting the Table, but service is when something is happening to you—hospitality is when something feels like it’s happening for you. Great design is when something is done so well that it feels like it was made exactly for you, even though it’s designed for millions.

“Great design is when something is done so well that it feels like it was made exactly for you, even though it’s designed for millions.”

How did you and Kate Adamson decide to work together as co-founders?

It was very quickly clear that Kate and I decided we wanted to work together. She started at Plaid as one of the first go-to-market hires and at that time we worked a lot on special pitches. We pitched to get Apple to use Plaid for the ACH verification authentication flow with Apple Card. Plaid also had a culture around quarterly hackathons, and Kate was always one of those people that would have her own team, but she would also create like five other teams at the same time. She had so many ideas that were compelling, and it jumped out at me that she had a really powerful way of being a creative leader.

After we both had left Plaid, we decided during one of our regular breakfast meetings to build something together.

We definitely went through a maze to land on the right idea. We started with some core principles around what mattered to us. The main one was about serving local economies and small businesses. The first decision we made was not, what are we working on? It was, who are we working on it with? And that meant, what customer are we serving?

Al and Kate in the early days at Elizabeth Street Garden in NYC.

💡 What this means for you: Don’t leave finding a co-founder to chance. Make a running list of colleagues you admire and revisit it regularly. Sometimes the best partnership is hiding in plain sight among the people you already trust and enjoy working with.

How do you balance being a designer with being a co-founder?

Being a designer founder is like being a founding designer, but with even less time for design. Otherwise, it’s very similar. We’re all like: how do I find the time to do the one thing that I’m really, really good at? It’s hard to do that unless you’re incredibly intentional about it.

I have to focus on time management quite a bit and carve out time to just go design stuff—whether that’s doing research or generating ideas or polishing pixels just before launching a new feature—because I very much love jumping into code, now more than ever.

I have to balance that with my responsibilities as a founder. My role is very much focused on leading our product engineering design motions. Right now there are five of us writing code. Then we have operations and go-to-market with Kate, Gen, Greg, and Omar. We’re at an inflection point where we’re going to have to get a little bit more structured, but for the most part we’re just focused on: what’s going on this week, what are we building?

The main principle that I’m leaning on right now is that the best way to make product decisions is to visualize ideas and prototype. I’m a big Cursor stan.

A peek into Al’s Cursor workflow for Folio (look closely for a fun surprise!)

💡 What this means for you: Set aside intentional blocks of time for deep work. Treat these sessions as non-negotiable meetings with yourself. The creative breakthroughs that set your product apart are most likely to happen when you regularly make space for focused, uninterrupted design.

How do you bring soul into B2B software?

My favorite thing about enterprise software is the bar is pretty low, and that’s a great starting point. Not to make it marginally better, but to start from first principles: we want to make this super easy to use, like how everyone knows how to use an iPad without instructions.

Here’s a concrete example: You can create shopping lists on Folio, which hotels use for complex menus and inventory. We noticed these lists need to be organized by shelf order—“shelf to sheet”—so staff can efficiently gather items. We built drag-and-drop reordering, but then asked: what else might make this delightful? We added a satisfying sound every time you move items around. Small details like that make the experience feel more human.

Our customers benefit from consumer-grade design principles because hospitality requires business-to-business tools that still feel personal and intuitive.

Folio makes ordering supplies easy and delightful for hospitality teams.

What role is AI (artificial intelligence, that is) playing at Folio?

AI has helped us imbue delight into our product with the scrappy resources we have as a startup. A little over a year ago, my designer friend Stefan and I were both copy-pasting from ChatGPT into VS Code—we were laughing about doing the same ridiculous workflow.

Now with Cursor, the ergonomics keep getting better. As a startup, we can adopt these tools faster than large companies, and our nimbleness becomes a competitive advantage. AI lets our small team focus on prototyping and shipping rather than getting bogged down in repetitive tasks.

💡 What this means for you: Don’t get stuck trying to craft a perfect AI roadmap. Instead, identify the most repetitive or tedious task in your workflow and focus on automating that. Whether it’s cleaning up design specs or generating code snippets, small wins add up and free your team’s creative energy for the work that actually matters.

Any advice for your past self starting out?

I would tell myself (because this is something I was curious about) that yes, building a startup is exactly as hard as people say—and 10x more fun. It requires dedication, determination, consistency, thoughtfulness, and integrity. But it is so rewarding. The connection to people, to your customers, to creativity, to whatever motivates you…those are the big things.

The advice I’d give someone considering this: just do it and go without fear. Be aware it’s as hard as they say, but it’s also a lot more fun.