Today he runs UserOnboard, a one-person consulting operation that helps software services better acquire new users. Samuel has built a cult following in an oft-overlooked aspect of design by publishing teardowns: witty, step-by-step critiques of the onboarding flow for popular software services, such as Slack, Buffer, and Twitter. The teardowns are equal parts insightful and cheeky, revealing invisible pitfalls through the lens of consumer psychology.
Relaying the story of his first public teardown, Samuel remembers waking up to a sense of dread after posting it online. “I woke up the next morning, and in my inbox was an email from one of the founders of the company. I was sure that it was going to say: ‘Hey, thanks a lot for airing our dirty laundry,’ or ‘At least give us a heads up before you post it,’ or ‘Who are you and what’re you trying to do?!’ And it couldn’t have been more opposite. The founder’s tone was: ‘Thank you so much, we’ve already made the changes you’ve recommended. Looks like you’re writing a book. Can we help promote it?’”
I’ve always been very intentional in the audience I’ve crafted. I wanted the relationship to be a celebration of our similarities as people, as opposed to trying to cultivate some sort of aura.
To this day, none of the teardowns have received negative feedback. Samuel admits that the relatable, empathetic tone he uses may have something to do with the lack of backlash.
“I don’t want to come in and just trash other designers’ work. There have been so many times where I’ve encountered something that looks ugly as hell, or just looks wrong, or feels bad, but it just works really well. Coming out of it from a place of humility, where I’m like, ‘Look, I can’t comment on whether this is the “right” design decision or not. But as a user going through this, I was confused, or unclear on what was happening,’ I’m trying to provide constructive recommendations and just convey my experience—more than coming in and objectively saying something was good or bad.”
And perhaps it’s this humility that endears Samuel to his audience, too; he’s conscious of appearing relatable while carving a niche as an expert. “You look at “thought leaders” who seem like prisoners of the mystique they’ve created about themselves,” he says. “They can’t just be seen as a fallible human being. I’ve always been very intentional in the audience I’ve crafted. I wanted the relationship [with fans] to be a celebration of our similarities as people, as opposed to trying to cultivate some sort of aura.”
Frustration triggered Samuel’s fascination with user onboarding. Working as a developer, coding websites directly from pictures left him feeling disgruntled; Samuel would often identify flow and usability issues, the majority of which weren’t considered important enough to rectify. “I had to grit my teeth and code up something that I didn’t feel served the end user,” he recalls. “I wanted to really get in earlier on the decision-making process, and realized what I was frustrated with was called user experience design.”
And after years of honing his professional expertise at various agencies and startups, Samuel was chosen for a three-month marketing apprenticeship (“I left my full-time job to become a thirty year-old intern, basically”). The foray into marketing products for other people inspired Samuel to create a book on user onboarding. But as the sole income earner of his family, taking the time off to write presented a huge risk.
A graphic from Samuel’s book, The Elements of User Onboarding
“When those three months [of the apprenticeship] were over, we had a little bit in savings. We calculated that if we went three months without me earning anything, then we’d have just maxed out our credit cards at that point. If the book launch didn’t go well, I’d have to go find consulting work. At the time I was the sole breadwinner of the family, so we were effectively cutting out the safety net, but we decided to tighten our belts to see if this could work. We knew that if it worked, it had the potential to really change our lives. And if it didn’t, then we’d just try to scramble and recover afterwards.”
Samuel recalls going into the morning of the book launch thinking “If I’m going to get $200 out of this, I’m going to be so screwed." But his efforts in building an audience for his site, UserOnboard, paid off.
He made $7,500 on launch day; $20,000 that week.
Producing new teardowns for popular software services helped to grow the business. Book sales increased, his audience grew, and consulting work continued. “It’s turned into definitely what I’d call a financial success. But the launch itself was a little bit shaky, I guess.”
Today Samuel consults for some of Silicon Valley’s best-known successes, but he prefers to remove himself from the daily bustle, and keeps Portland as his home base. “There’s a flow of ambition and tension to certain cities. It’s easy in the software or tech world to get really caught up in what we’re doing, and look at so-and-so’s Series B as a really important event,” he says. “But if you take a step back and look at the person using the software—and not just the software—it’s always helpful to remind yourself of the human element.”
Portland itself may feel unhurried, but it doesn’t exempt Samuel from the endlessness of the entrepreneurial workday. He admits that a sleep disorder makes his work schedule “extremely ad-hoc,” and says he worked “some crazy long hours” while writing the book.
“I really underestimated how hard it would be to sit down and try to formalize some sort of vocabulary around something that no one has really covered yet,” he says. "There were times where I would work until I fell asleep at my computer, and wake up finding myself on the couch, and just get back to work. There were some really, really long days there. But I also didn’t want to let myself get too distracted.”
Samuel continues to work out of the standalone garage he converted into an office long ago, though the couch in there is strictly for impromptu napping and not the few hours of shut-eye that barely masqueraded as real sleep during his book-writing period.
He prefers to dive into work first thing in the morning. “I try to stay off of anything that divides up my attention early in the day. Your batteries are recharging as you sleep, and you wake up, [and] get lost in the minutiae of little things like email. It was hard to get that cohesive mindfulness back after it was lost.” Downtime is filled with reading (“A lot of my design philosophy is informed by reading things in a similar space, but not about software: about human psychology, brain science, architecture.”), watching basketball, and caring for his four-year-old son.
A fundamental question is: If your product was a person, would you enjoy having a conversation with it? Products with personality shouldn’t be so rare.
Just as psychological insights can be applied to manipulate the actions of others, so too can the elements of user onboarding be used to regress the lives of users. According to Samuel, the most notorious of perpetrators to use this method are apps and services that proactively strip time from users.
“Stealing time from people is something I find so concerning. I’ve been thinking about casinos, and slot machines, and apps that are predatory of people’s time and money, like Farmville. It’s the most advanced user experience design in a way that’s not aligned with making people more successful. Money can be abundant, and it can come and go, but people are all losing time at the same rate.”
In Samuel’s paradigm, everything in the world is a user experience waiting to be improved. Booking a ‘beautiful’ vacation rental online, only to arrive and find that the rental’s amenities were less than satisfactory, left Samuel wanting (“There was so much friction to the experience”). When asked if there were a real world user experience he’d like to fine tune, he’s quick to reply: “Airports, for sure.” A recent collaboration with Code for America resulted in Samuel turning his teardowns towards public services; Citizen Onboard is a site that uses teardowns to examine how well government services work, so that they may be improved.
Samuel’s altruistic approach to applying user onboarding for the betterment of the individual is a gratifying antithesis to the fear that we are but puppets whose right-swiping fingers are influenced by the invisible strings of user experience design.
“If we want to be providing this transitional experience for someone and improving their lives, why are we measuring things like time spent on site? We should be getting people off the site and living the good life, instead of trying to keep them on our site for our own purposes.”
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