Understanding your users’ emotional state should be every founder’s priority according to WorkMade’s Nick Simpson, who says creative decisions only fly when they take into account how they make people feel
Creative director Nick Simpson has spent the last decade building and advising emerging consumer companies, working at names including specialist skincare brand Becky, drinks supplement brand Hydrant and organic skincare brand HAOMA.
In 2022, he decided to branch out into a sector he’d never worked in before: finance. Fuelled by his own frustration at the confusing tax system in the US, he set up WorkMade – an app that streamlines the process of paying tax, aiming to make it “nearly invisible” for freelancers. In the last two years the business has been backed by tech investor M13 as well as Slack’s investment arm.
We chatted with him about being “a pretty emotional human”, and how that’s guided his founder journey as well as his approach to marketing, design and creativity.
- Emma TuckerDo you think your background and experience so far has given you a different sensibility for the creative aspect of growing a business?
Nick SimpsonYes, I definitely think the end user – whether it’s a physical good or not – is the most important. That’s always been my focus – who’s going to be on the other end of the screen and what are the emotions that person is going through?
What’s the first time this person interacts with your brand? Is it word of mouth or seeing an ad, and how do you close the entire loop? What’s the email they’re going to get? The text message? What’s their first experience, and how do you make every single step of the way magical? I think adding delight at every step is what keeps that person going, so attention to detail is important.
- ETI was reading some trend reports at the start of the year, and something that came up again and again was that people want their CEOs to be more empathetic - but that a lot of business leaders struggle with that. What you’re describing feels like a very empathetic approach to building a business and a product.
NSIt’s funny you say that, because the tagline for our pitch is ‘where AI meets financial empathy’. You hear a lot about AI and it’s often very misleading – everyone’s like, ‘we’re the next AI-this’. We never mention it, it just happens in the background. Empathy is good, I think, in most products, and it’s such a strong word.
For me, the idea of the whole product and how creativity filters through that with empathy and understanding is what people want. And I think being a founder of a business that’s come via an unconventional route is good – we’re getting to a situation where a lot of founders are people with private wealth, that come from a background that lacks any sort of empathy, or maybe have one or two failed startups and already have a network. We need different kinds of people building businesses.
- ETCan we talk a bit more about that ‘unconventional’ route you mentioned?
NSI started my first website project when I was 9, so I’ve been freelancing for more than half my life. I’m a high school dropout. I’m a college dropout. I never really enjoyed the educational track. I just love building. I want to learn and iterate, and that’s what pushed me down this path – even though I don’t really feel like a founder. I feel like an employee of my own company, because I’m always working with our team. I’ve never really understood that traditional structure in a company, so it makes it a lot easier when your team feels you’re an active contributor.
I think having that more integrated approach between myself and the team is usually frowned on by a lot of investors. And I think what’s going on in the industry right now is that founders and visionaries are being pulled away from their initial vision. They have a couple of other people running it, and they’re not supposed to give direction. So you end up with a lacklustre product.
I bet you can name two or three products you used to love, and then two or three years later they wind up changing into something you never wanted. That happens a lot, and I think it’s because founders feel they have to lead and not follow, and it’s a very old way of thinking. This approach can sometimes lead to changes that stray far from what users originally valued.
“We want an app that has thousands of people on it, but all of them still feel like they’re the only person in the room.”
- ETDo you feel like some companies have forgotten how to make digital design joyful, as well as easily usable? I feel like my own digital life, with all of the notifications and complexity, sometimes gives me such quiet rage.
NSI strongly agree. I just want to get done what I need to get done. I don’t need the jargon. I don’t want to be talked to like I’m a user, or over-explained to. I feel like if you need a guided tour, you’ve built the wrong product and you do not have a good user experience. It’s something that bothers me so much using apps – there’s so many buttons and options, and they’re loaded with features. But I’m like, why don’t we turn features into actions, where if I want to do something I can, easily? That’s how we think about it.
- ETThis might be the false memories of nostalgia, but it feels like there was a point in design where things were straightforward. But now we’re talking about feature bloat – apps don’t just do one thing, they’re super-apps. Instagram is no longer an image sharing app, it’s a messaging app, a video app, a shopping app…
NSI feel like that with our app too: we have to be able to accept in-person payments, send invoices, take payments from other apps. And all that whether you’re a dogwalker or an Uber driver. So the way we designed it for the user is that we have a lot of features, but the content is solely related to someone’s industry. We use puns and copy to make it more fun and delightful.
We want an app that has thousands of people on it, but all of them still feel like they’re the only person in the room – that’s where most of the opportunity is for AI. It would be so magical if you can go to our app in years to come, login, link your bank accounts, and we just understand you as an individual better than a bank would. It could be like, ‘oh, you’re going to Soho House again this week, it’s probably a business writeoff because you do this every week at this time’. I’m super excited for that.
“If you disappoint a user, how are they feeling? How can you make them feel better? You have to really spend time understanding people from an emotional perspective.”
- ETGoing back to all the experience you’ve had in different places, are there big lessons you’ve learned about business and creativity along the way – any hard lessons that it hurt to learn?
NSDon’t forget your user. There’s somebody on the other side of the app, and as you start building and growing you can forget about them. They are the most important thing. Every week I reach out to a random user who I think is an ideal fit for our platform, send them a text message and say, ‘Can I give you 25 bucks for a drink or coffee, and can we chat for an hour? I just want to learn about you, how you use the product and how you found it’. You’d be amazed by the things that you learn - for example someone couldn’t upload a receipt, so never used it again. It was a 30-second fix for us to resolve this, and if we hadn’t spoken to this person, we’d never have seen them again. They are our largest revenue driver to date – because of one of our smallest features that didn’t matter much to us. You learn so much by actually sitting with your users.
- ETThat’s going back to empathy again. And I love that you talk to these people for an hour, which feels like almost a journalistic way of figuring out business problems.
NSConversation is the most powerful thing in the world. So when I can hop in our product and build, I recall every conversation and the way someone felt. There’s that Maya Angelou quote about people forgetting what you did or said, but remembering how it made them feel. It’s the same with product and building brands – people aren’t going to forget. If you disappoint a user, how are they feeling? How can you make them feel better? You have to really spend time understanding people from an emotional perspective.
- ETAs a founder, you’re obviously very connected to the day-to-day reality of people using your product. But if you’re a big brand, if you’re the CMO of a huge company, is it still possible to have that level of understanding?
NSI 100% think if you don’t have an hour or even 30 minutes to get a coffee with a user, then what are you building? Where are the other hours of your day going? What are you really doing? So I would tell everybody that says, ‘I don’t have time to talk to my customers’, that that’s the single point of failure for the entire company, in my opinion.
- ETI wanted to conclude on a big, semi-philosophical, semi-business question. The economy is all over the place, businesses are running out of cash, and undoubtedly times are very hard. Why would, or should, someone spend money on creative work?
NSIt’s really all we have left. There’s always a story to be told, and we love listening to stories – that’s the one thing every human can agree on. Our whole life is built around it, and I think creativity is the conduit to making it happen. It’s the baseline for empathy, emotion, and the ‘why’ behind something. If you're not investing capital in a bigger meaning, why build in the first place?
If you look at the top 100 tech companies most recently invested in, they all look the same. This one does this, that one does that, but nothing stands out anymore. I don’t want to go to a website that’s like, ‘0% fees, interest-free, open your free LLC today’. What does that mean? I want to see me, and me building my business. I want to see how easy it is and I want to see other people like me. I want that experience, and you need creative to tell that narrative. So I’d 100% hire an agency. I’d hire 10 to get the narrative right before I even went out with a product.
And creativity takes time. Things have to grow; you don’t just put a seed in the ground, water it, and magically it’s a tree. People don’t have the patience anymore for creativity – they want to be Apple, and it’s like, great, that took them 50 years, multiple product iterations, tonnes of setbacks, creating new designs and trying to build something new. You see megabrands, and it’s a lot of work.
All our competitors will do better than us for the next three or four years, because we’re not doing what they’re doing. But we’ll be here when they’re not in ten.
