A few years ago, Dropbox redesigned its website and revenue dropped by thirty percent. It was an all-hands-on-deck moment: people working weekends, everyone hunting for a systemic failure.

The culprit turned out to be a pricing page — specifically, the white space between the feature list items was slightly too generous. Angel Steger noticed that her eye kept landing on the white instead of the words. They tightened the gaps, and the revenue came back.

That’s the kind of thing Angel notices, and it’s not an accident. Currently the VP of Design at Wealthfront, She trained as an architect at RISD, where the first question in her first architecture class wasn’t about buildings. It was “What is a drawing?” — the sort of question that makes you realize every tool you reach for carries a point of view you probably haven’t examined.

Angel’s path into tech was less deliberate. By her own account, she mouthed off to her boss, got fired, and spent the severance on O’Reilly books, taught herself to code, and became the first designer at MySpace — where the head of engineering proudly informed her that they had never had design and never would need it. She went on to become the first product designer at 23andMe, learned usability from Larry Tesler, and led design teams at Pinterest, Dropbox, and Meta before landing at Wealthfront.

In this conversation, we get into what architecture teaches you about solving one problem at a time, why she tells her team to go lower fidelity, how a default chart setting can push someone into a financial decision they’ll regret, and what she looks for in a portfolio — high craft, high intentionality, and no boiled broccoli.

Bio

Angel joined Wealthfront in November 2023 and leads product design, content design, and creative teams, bringing 20+ years of experience building and leading customer-centric, business-focused design and product teams. What makes her perspective rare is the through-line she draws between business model and design quality — she's a practitioner who built her career arguing that growth design, done with rigor and craft, isn't a compromise but the highest form of product work. Beyond Wealthfront, she holds advisory positions at AudiencePlus and Ameelio, and previously held leadership design roles at Meta, Dropbox, and Pinterest, where major growth and user engagement initiatives were implemented. She guided Wealthfront's design organization through its December 2025 IPO, in which Wealthfront's shares began trading on the Nasdaq Global Select Market under the ticker "WLTH" — the first robo-advisor to go public.

Show notes and links

Do > Show > Tell —

LinkedIn — https://www.linkedin.com/in/angelsteger/
Reforge — https://www.reforge.com/experts/angel-steger
Medium — https://medium.com/@angelsteger
Pixelated Path: "From Architecture to UX Design Leadership" —

Pixelated Path

From Architecture to UX Design: A Conversation with Angel Steger

What can architecture teach you about digital design? More than you might think…

Listen now

2 years ago · 2 likes · Chris Abad and Angel Steger

Some additional thoughts from Angel below:

1. Re: architecture. The third thing is the trial-by-fire nature of architecture school. You don’t get taught anything—you are merely handed problems, and are forced to come up with your own tools to solve them. That was incredible training for tackling very high level problems that a lot of people get scared or overwhelmed about. You get very good at breaking down complexity into something that can get executed.

Architecture is a team sport. You can't build a building alone — mostly you're building the dream of a building, together. That's why we ask, "what is a drawing?" It's a story, a point of view, built to become a shared vision. I struggled with individual work, but in groups I could pull good ideas out of the room and synthesize them into something people rallied behind. I'd end up leading without meaning to. My comfort was in the collective, never in coming down the mountain with two tablets.

2. Interviewing. Why the counter-intuitive portfolio (show what you’re proud of, not just “what’s relevant”) worked for me at Wealthfront: it showed that I’m the kind of design hire that thrives by coloring outside the lines—and made it very clear that hiring me is to hire someone who doesn’t just sit at the table, but actively builds tables, and invites others to build with me. If the hiring team wasn’t on board for that, we both got great signal right away that this wouldn’t work. There is nothing that chips away more at your wellbeing than to be forced into a role that runs counter to your values, your nature, and your strengths—and nothing better than to be set up to be your fully activated professional self.

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What Portfolio Club taught us about designing a great portfolio

Of everything you’ll ever design, your portfolio is the hardest to see clearly: you’re too close to judge it the way a stranger would. It’s also easy to spend your energy on styling and lose sight of whether the work itself is presented well. And before styling even matters, there’s the technical work of building the site, which stalls plenty of good portfolios in a Figma file. Claude Code and tools like it can clear that path without taking over your creative decisions, and we’ll walk through how later in this guide.

This guide draws on Design Better’s Portfolio Club critiques, where designers who’ve hired at Apple, Google, Adobe, and beyond review real portfolios on camera. Matt D. Smith, Bob Baxley, Daniel Burka, Brooke Hopper, Jared Erondu, Dan Harden, and Joey Primiani have each spent an hour with us, and their perspective runs through everything below, so you see your own work the way a hiring manager will.

Your portfolio may be the most valuable tool in your career, which matters now, with designers anxious about what AI is doing to the job market. The best answer to that anxiety is action, not reassurance. Build the portfolio. Find the job you want. Stop worrying about the changing world. Start designing for it.

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Portfolio design principles

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Like a lot of parents, Eli struggled over the years to get his kids more into reading and away from screens. He wasn’t necessarily on the search for a technological solution, but then an interesting device came our way: the Yoto Player, a screen-free audio player for kids. Eli’s 10-year old son has been loving to read along to the Harry Potter books (and he often finds him after he falls asleep, and the player is still going).

The story behind Yoto is from a similar moment of parental struggle. About a decade ago, Ben Drury was shopping for a stroller in a London department store and found one with an iPad mount built in. For a newborn. He remembers the reaction being physical — this is just wrong.

But if you’re expecting an anti-screen crusade, that’s not quite what happened . The line Ben uses is: we don’t say screens are bad, we say audio is good. Listening is good for creativity and imagination — and there’s research going back to the 1980s to back that up.

Ben is the co-founder and CEO of Yoto, makers of a kids’ audio player that works by dropping a physical card into a small speaker. Before Yoto Ben spent about a decade building a B2B digital music platform called 7digital which he took public. What he learned from that experience proved helpful as he and his co-founder started Yoto.

Ben and his co-founder became parents at roughly the same time, and wanted a way for their kids to connect with music and books like they did in childhood. So they started hacking on Raspberry Pis with no hardware experience whatsoever. How hard could it be, right?

Turns out, it’s pretty hard. They took a restrained approach. Yoto is a cube, because it was the simplest shape they could think of. It uses NFC cards that have a Pokemon card feel. The 16 by 16 pixel display presents pixel art that gives Yoto a fun personality.

In this conversation, we get into the design principles that came out of Montessori, their experience working with Pentagram on product design and branding, why Paul McCartney became an early angel investor, and what changes when you go from a Kickstarter that raised fifty thousand dollars to nine-figure revenue.

Bio

Ben Drury is the co-founder and CEO of Yoto, the screen-free audio player that lets children control their own listening by dropping a physical card into a speaker. Before Yoto, he spent roughly a decade building 7digital, a B2B digital music platform he took public. He and his co-founder started Yoto in 2017 with a Kickstarter campaign and no hardware experience between them; today the company employs about 220 people across six countries, sells in 1,900 Target stores in the US, and counts Paul McCartney among its early angel investors. He lives in London with his wife and two sons.

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The designer Stefan Sagmeister isn’t known for being subtle. A poster he created in 1999, for an AIGA lecture he delivered in Detroit, was carved with an X-acto blade into his chest and torso. One prominent feature was a consistent motto of his, Style = FART.

He later created a whoopee-cushion with the same slogan.

So Sagmeister might appreciate our conversation with Jeff Hammoud, Chief Design Officer at Rivian, who takes a similar stance on design vs. styling.

As designers, we often put a lot of ourselves into our work. Then that work, whether its a concept, a prototype, or a beautiful comp, gets flattened on its way to the real world. Maybe your work wasn’t a car design. Maybe it was an app, a rebrand, a prototype that never survived the handoff to engineering. It comes out the other side and you barely recognize it.

Our conversation with Jeff — recorded live in Miami during Art Basel, in the Rivian Pavilion — was in many ways about how to keep that from happening. Jeff runs a design org of around 140 people spanning interior, exterior, color and materials, digital, and a dedicated studio engineering team. And the red thread running through what he told us was a provocative idea about what design even is.

Listen to the episode

Jeff Hammoud, Rivian CDO: Spotify, Apple Podcasts, Substack, Youtube

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Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain.

We’re working on putting together some scholarships for this event. Please fill out the short form below if you’re interested:

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Constraints are the job

Jeff’s never been drawn to concept cars. To him they’re “gratuitous” — beautiful ephemera that typically never make it to manufacturing. His definition of a designer hangs on the presence of constraints:

“Can somebody design something without any constraints? Yes. And I think working within constraints is really what makes us good designers. Otherwise, we’re just stylists. Can you make a car look pretty? Yes. But can you make it aerodynamic? Can you make it meet the engineering requirements for safety? Can you make sure all the design provides good fit and finish? It’s manufacturable. How do you reduce costs in it without it looking cheap? Those are all the things that are really important as we’re looking to design a vehicle.” — Jeff Hammoud

That’s the “one rule” underneath Rivian’s process: the design team never shows something it doesn’t intend to actually build. And the way they protect that intent is structural. A dedicated studio engineering team sits inside the design org, adjacent to the designers, giving early feedback on manufacturability so the debate over what’s buildable happens before it ever becomes a fight:

“We’ll never show something if we don’t have an intent to really make sure that, if we’re saying we’re going to build this, it looks just like what we show.”

Most of us have lived the opposite. You’ve seen the stunning concept, then the production version that makes you ask, “what happened?” Jeff’s answer is that the gap between concept and reality is where design actually happens, if you’re set up to do it.

The cautionary tale

If you want to see Jeff’s philosophy proven in the negative, look at a story Tony Fadell told us about General Magic — the legendary early-’90s startup where the team that had built the Macintosh set out to build what was essentially the iPhone, but fifteen years too early.

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This is a special bonus episode, an interview with Rivian’s Chief Design Officer, Jeff Hammoud. We’ve got all the audio here, but it’s worth heading over to our Youtube channel at dbtr.co/youtube to watch the video.

We recorded this one live in Miami, in the Rivian Pavilion during Art Basel, with a R1T truck in a new eggplant-purple called Boreal parked just over Jeff’s shoulder.

Jeff runs a team of about 140 people across Irvine and Palo Alto — interior and exterior designers, color and materials, digital surfacing, perceived quality, even an in-house painter and a clay milling shop. And he has a strong opinion about what all that machinery is for: constraints are what separate designers from stylists. Anyone can make a beautiful concept car, but making the production version look like the concept is the challenge.

We talked about why Rivian keeps making colors most people won’t buy, and how limited-run “Studio Originals” work like sneaker drops. Jeff makes the case that AI is going to level the playing field in design — shifting the advantage from whoever illustrates best to whoever has the better idea. We got into which controls stay physical and why, the haptic halo wheels coming in R2, and how scent ties a car to memory.

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

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A field guide to AI prompting

This week, we’re sharing a chapter from Think. Prompt. Create, a book written by Joey Primiani’s, a member of the Design Better community.

Most of the anxiety we hear about AI isn’t really about AI. It’s about not knowing where to start. People tell us they’re worried about their jobs, but when we ask what they’ve actually tried, the answer is usually “not much yet.” The fastest way out of that spiral is the least comfortable one: open the tool and use it badly a few times until you get better at it.

Joey Primiani has put in thousands of hours doing exactly that. He’s a longtime Design Better subscriber, and he just published Think. Prompt. Create: A New Way to Build Software — a book about how to actually work with tools like Claude Code, not just poke at them. It’s a solid on-ramp if you’ve never touched one of these tools, and specific enough that people who already have will still walk away with something. We asked if we could run a chapter. He said yes.

What follows is Chapter 4, “The Art of the Prompt: Talking to Your AI Partner.” It offers a clear breakdown of why some prompts get you exactly what you wanted and others get you three hours of cleanup.

Get Think. Prompt. Create on Amazon →

Chapter 4: The Art of the Prompt, Talking to Your AI Partner

by Joey Primiani

Here is a secret that most Claude Code tutorials bury: the quality of your output is almost entirely determined by the quality of your input. Claude Code is extraordinary, but it is not psychic. It can only work with what you give it. Every frustrating session, every confusing output, every “why did it do that?” moment can almost always be traced back to an ambiguous or incomplete prompt.

The good news: prompt writing is a learnable skill, and the principles are simpler than you might think.

The Five Pillars of a Good Prompt

After thousands of hours working with Claude Code, I have distilled effective prompting into five principles. Master these and you will consistently get better output than most developers.

1. Be Specific About Outcomes, Not Steps

The single biggest beginner mistake is trying to be too prescriptive. People write prompts like:

“Create a function called getUserData, make it async, use the axios library to call https://api.example.com/users/{id}, and return the user object.”

When what they should write is:

“Add a function that fetches a user by ID from our API (https://api.example.com/users/{id}) and returns the user data. We’re already using axios elsewhere in the code.”

The first prompt is a recipe. The second is a goal. Claude Code is a senior developer, give it goals, not recipes. It will make better implementation decisions than you will if you try to micromanage every detail.

The exception: when you have specific, non-negotiable technical requirements, spell them out. “Use async/await rather than promises” or “the function must handle the case where the user doesn’t exist by returning null, not throwing” are legitimate constraints, not micromanagement.

2. Provide Context, Liberally

Claude Code knows your code only as well as it has read it. For a fresh session, that means Claude Code knows only what is in the files in your current directory. For a continuing session, it knows what it has read during the session.

When your request depends on something Claude Code may not have seen, tell it explicitly:

“In our app, authentication is handled by the AuthService class in src/services/auth.js. Given that setup, add an endpoint to /api/profile that returns the current user’s profile data, requiring authentication.”

You just told Claude Code: go read that file, understand how auth works, then implement the endpoint in a way that is consistent.

You can also directly ask Claude Code to read files before proceeding:

“Read src/database/schema.sql and src/models/user.js, then help me add a ‘last_login’ field to the users table.”

Claude Code will read both files and use them to inform its answer.

3. State Constraints Upfront

Every project has constraints, technology choices, coding conventions, performance requirements, compatibility needs. Front-load these in your prompt rather than waiting for Claude Code to make the wrong assumption:

“We’re using vanilla JavaScript with no frameworks. Our database is SQLite through the better-sqlite3 library (not async, it’s synchronous). Add a function to insert a new order.”

Without that context, Claude Code might produce async SQLite code, or use a different library, or assume you are in a React project. With it, you will get exactly what fits your stack.

This is also why the CLAUDE.md file is so valuable, it provides standing constraints for every session without you having to repeat them.

4. Use Examples When the Format Matters

If you have a specific output format in mind, a particular data structure, a specific visual style, a certain code pattern, provide an example:

“I want to add error handling to this function. We handle errors like this elsewhere in the codebase: try { const result = await doSomething(); return { success: true, data: result }; } catch (error) { logger.error('doSomething failed', { error: error.message }); return { success: false, error: error.message }; } Please use the same pattern.”

Examples are unambiguous in a way that descriptions rarely are. Show, do not just tell.

5. Ask for Explanation When You Need to Understand

This is underused. Claude Code is not just a code generator, it is a teacher. If you want to understand what it is doing:

“Add the search functionality, and after you write the code, explain how it works in plain English, pretend I’m a beginner developer.”

Or at any point in a session:

“Before you write the code, explain your plan, what files you’ll touch, what the overall approach will be.”

This second one is especially useful for complex changes. If Claude Code’s plan sounds wrong to you, you can redirect before any code is written.

Prompt Patterns That Work

Here are specific prompt structures that consistently produce excellent results:

The “Context + Goal + Constraints” Pattern

[Context: describe the current state]
[Goal: describe the desired outcome]
[Constraints: technical or stylistic requirements]

Example:
"Our checkout form currently collects name, email, and address.
I want to add a phone number field that is optional.
The field should validate that the input is a valid phone number if provided, and we should use the same input component style as the existing fields."

The “Negative Space” Pattern

Tell Claude Code what to avoid:

“Add a caching layer for our API responses. Do NOT introduce any new dependencies, use only what’s already in our package.json.”

“Refactor this function to be more readable. Do NOT change its behavior or its interface, existing callers should not need to change.”

The “Scope” Pattern

When you want a focused change, explicitly bound it:

“Only look at the src/components/Header.jsx file. Don’t change anything else. Make the navigation links highlight when the current page matches.”

The “Thinking Out Loud” Pattern

For complex architectural decisions:

“I want to add real-time notifications to our app. Before writing any code, think through the options, we could use WebSockets, Server-Sent Events, or polling. Given that we’re on a serverless platform, explain which approach makes most sense and why.”

This produces a deliberate reasoning process rather than the first implementation that comes to mind.

Multi-Turn Conversations

Claude Code is not a single-shot tool. Some of the best work happens over multiple turns:

Turn 1: "I want to add user authentication to this app. What are the main
         things we need to implement?"

[Claude Code responds with a list: password hashing, session management,
login endpoint, registration endpoint, protected routes…]

Turn 2: "Let's start with user registration. Implement the registration
         endpoint and the password hashing."

[Claude Code implements…]

Turn 3: "Good. Now run our test file (! npm test) to make sure we haven't
         broken anything."

[Tests run, output shows…]

Turn 4: "The test for the user model is failing, the error is [paste error].
         Fix it."

This is how real development works. Not one big prompt, but an ongoing dialogue that iteratively builds toward the goal.

Prompts to Avoid

Just as valuable as knowing what works is knowing what does not:

Vague directives: “Make this better.” Better how? Faster? More readable? More secure? Be specific.

Too many things at once: “Add user authentication, redesign the homepage, fix the search bug, and add PDF export.” Pick one thing. Doing too many things in a single prompt produces muddled output and makes it hard to isolate problems.

Prompts without context in a fresh session: “Fix the bug in the user model.” What bug? Which file? Claude Code has not read your code yet.

Emotional framing: “This is terrible, please fix everything.” Claude Code does not have feelings (in any meaningful sense), but vague negative framing does not give it actionable direction. Say what you want, not how you feel about the current state.

The Feedback Loop

One of the most powerful things you can do is close the feedback loop by having Claude Code verify its own work:

“After you make the change, run ! npm test and show me the results.”

“After building the form, open a quick server with ! npx serve . and tell me the URL so I can test it.”

“Check if there are any obvious issues with the code you just wrote before I test it.”

That last one, asking Claude Code to review its own output, catches a surprising number of issues. It is not infallible, but it adds a quality gate with zero effort on your part.

Giving Good Feedback

When Claude Code produces something that needs adjustment, your feedback prompt is its own kind of craft:

Imprecise feedback: “This doesn’t look right.”

Better feedback: “The layout looks wrong, the button is appearing on its own line but it should be inline with the text input, side by side.”

Best feedback: “Here’s a screenshot of what I see [description or file], and here’s what I expected. The button should be to the right of the input on the same line, not below it. Can you fix the CSS?”

The more specific and visual your feedback, the more precisely Claude Code can target the fix.

The “Staff Engineer” Prompt

This is one I use regularly when I want the highest quality output:

“Approach this as a staff engineer who cares deeply about code quality, maintainability, and avoiding over-engineering. [Then your request.]”

Or even more specifically:

“Before writing code, think about whether there’s a simpler approach that achieves the same goal. I’d rather have 10 lines of boring code than 50 lines of clever code.”

The Claude model responds to framing. Invoking quality-conscious, experienced-developer framing tends to produce exactly that kind of output.

If this chapter was useful, the rest of the book goes deeper: how to structure CLAUDE.md files, when to trust Claude Code’s judgment versus your own, and how teams are changing their workflows around it entirely.

Get Think. Prompt. Create on Amazon →

Until next week, write your next prompt like you’re briefing a senior engineer, not filling out a form.

— Aarron & Eli

If you’re not already a Design Better paid subscriber, get 20% off an annual subscription and get access to all our Portfolio Club events and recordings. You’ll also be invited to the Design Better Slack community where you’ll find great designers and past guests on the show providing design advice.

20% off annual subscription

Thank you to Jalen Igbeare and Tom Grimm for sharing their portfolios.

And thank you , , , , , and many others for tuning our live video with and !

In 2011, I came into Silicon Valley as a bit of an outsider. Up to that point, I’d worked at small companies designing physical products like underwater camera equipment, and then started an underwater photography magazine. Neither was a big moneymaker (surprise!), so after our daughter was born, I thought I’d try my luck in the software design world.

My first interview, a year prior at a quickly growing and now notorious company I won’t name, was an immediate culture shock.

“You should wear a suit,” my wife told me.

“No, too formal. I’ll wear a sport jacket and jeans,” I replied, full of my perceived wisdom.

When my first interviewer showed up looking like he’d slept under his desk, with basketball shorts, dirty gym socks, and no shoes, I knew I’d never get the job.

But I was determined to figure it out, and by the next year I got into a startup accelerator at the venture capital firm Innovation Endeavors. Eric Ries had just published The Lean Startup, and everyone in the SV ecosystem was quoting it. MVP (minimum viable product), the pivot, build-measure-learn: this terminology became the operating language of the startup world.

The words were useful but overused, and I like to think I was a little ahead of the curve when I designed some t-shirts poking fun at them in 2013. (HBO’s parody Silicon Valley wouldn’t come out until the following year.)

The most important product you’ll ever design

What struck me even then was how much of the Lean Startup methodology paralleled the human-centered design thinking I’d been trained on at Stanford: iterate fast, work with users, learn from failure, build empathy.

That overlap, it turns out, was no accident. Eric’s new book, Incorruptible: Why Good Companies Go Bad and How Great Companies Stay Great, is his reckoning with what happens after you build something great. A surprising amount of it speaks directly to designers. We talked with Eric about why speed was never the real problem, why the value a company creates comes from the design of its products, and why the single best way to use AI might be to refuse to let it do your work for you.

Listen to the episode

Eric Ries: Spotify, Apple Podcasts, Substack, Youtube

Already a paid subscriber? Follow this link to set up you premium feeds on Apple, Spotify or any other platform from your phone or computer.

Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain.

$100 off the event for those who book their own accommodation. Use code DBFRIENDS at this link:

Reserve your spot →

A second code for $15% off (also offsite accommodation) is available for Design Better premium members. Link and code after the paywall below at the bottom of this post.

Design thinking as the bridge

One of the things I most wanted to ask Eric about was the parallel between lean startup and design thinking. His answer was that the bridge was deliberate. He’d studied design thinking closely, and built relationships with its leaders, precisely because he’d noticed how much these allied disciplines distrusted one another:

“The agile thinking people and the scrum people and the design thinking people didn’t get along, and the scrum people and the DevOps people didn’t get along. I feel like there were all these people who I consider we should be natural allies fighting with each other because we have our own tribal identities and our own separate cultures.”

What lean startup offered, in his telling, wasn’t a new methodology so much as a shared language. It was a way for people who care about craft to be heard in rooms where the only accepted currency is ROI:

“If you ever tried to convince an executive that they should care about story points or burndown charts, even development velocity charts — let alone, God forbid, design integrity — good luck, right? Because they’re stack ranking by ROI. And you’re in there being like, let me explain to you why rounded corners are better for skeuomorphism. Like, what are you talking about?”

The consequence, Eric argues, is that the people who care about quality — designers, engineers, anyone with a craft — get pushed to the edge of the business conversation, their concerns treated as “parochial or almost a little bit juvenile.” And he thinks that’s exactly backwards:

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Fifteen years ago, Eric Ries handed a generation of founders a playbook. When Eli was in a Palo Alto-based startup accelerator in 2011, The Lean Startup felt like the only book anyone in that ecosystem was talking about. It was in the middle of a wildly optimistic moment for tech. Marc Andreessen declared that “software is eating the world,” social media was blooming, and there was a widespread belief that technology was about to democratize everything and bring us closer together. Concepts like the MVP (“minimum viable product,”), the pivot, and build-measure-learn became the operating language of Silicon Valley.

But a lot of the companies built on those ideas went on to get corrupted by forces Eric hadn’t yet named. His new book, Incorruptible: Why Good Companies Go Bad and How Great Companies Stay Great, is his reckoning with what happens after you build something great — and how to keep it from falling apart.

Buy the book

In this conversation, we get into why speed itself wasn’t the problem, but treating a rising stock price as proof of health is like assuming more exhaust means a faster car. Eric explains why doing the right thing 100% of the time is actually easier than doing it 98% of the time, and how companies behave like superorganisms with their own emergent character — a point he illustrates with a genuinely mind-bending study about ants solving a puzzle that no single ant ever could.

We talk about the “harder is easier” principle through stories from Patagonia and the long-term stock exchange he built as a design challenge, and why the value a company makes comes from the design of its products. And because we couldn’t resist, we get into AI slop, LLM psychosis, and Eric’s clear, simple antidote: never ask these tools to make you an artifact — ask them to teach you how to make one yourself.

Bio

Over the last two decades, Eric Ries’s ideas about continuous innovation, long-term thinking, governance, and market reform have reshaped company building and management practices. He is the creator of the Lean Startup method, and the author of the New York Times bestseller The Lean Startup; The Leader’s Guide; and The Startup Way.

As a founder, he has put his own ideas into practice with The Long-Term Stock Exchange (LTSE); Answer.AI, an AI R&D lab; the Lean Startup Co, which teaches and supports the implementation of Lean Startup; Virgil, a legal services startup; and IMVU, where the ideas that became the Lean Startup method were forged. On his podcast, The Eric Ries Show, he talks to guests including world-class technologists, thought leaders, and executives working to build profitable companies for the long-term benefit of society. Eric has served as an entrepreneur-in-residence at Harvard Business School and IDEO. He lives in the San Francisco Bay Area with his wife and three children.

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And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.

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Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

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When I was in college, I took a great printmaking class with the artist Enrique Chagoya. There were no assignments — he just taught various techniques, we’d present our work, and he’d offer a helpful critique afterward.

One of the many wonderful things about printmaking is the physicality of it: using a cutter to gouge out little strips of linoleum, inking the block with a roller, running it through the monotype press.

When pushing the gouge through block material, if your hand slips, you’ve ruined the line you spent twenty minutes sketching out. It’s slow. It’s a little dangerous (well, you can cut yourself). You can’t undo it. And that resistance is what makes the finished print feel like it came from somewhere. The mistakes can often make the finished work more interesting.

We tend to treat friction as a defect. Much of modern design has been about sanding it down: fewer steps, fewer decisions, less waiting. But the more I’ve made things by hand, the more convinced I am that friction isn’t the obstacle to meaningful work. It’s often the substance of it.

Carving a linoleum block with my daughter Phoebe around 10 years ago

That idea came up during our conversation with Ian Bogost, game designer, writer at The Atlantic, and author of the new book The Small Stuff. Ian has spent his career studying the designed life of ordinary things, and his book is essentially an argument for engaging with the small, textured, slightly effortful moments of daily life with curiosity and openness. It’s different than friction, though: he calls it gratification.

Listen to the episode

Ian Bogost: Spotify, Apple Podcasts, Substack, Youtube

Already a paid subscriber? Follow this link to set up you premium feeds on Apple, Spotify or any other platform from your phone or computer.

Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain.

$100 off the event for those who book their own accommodation. Use code DBFRIENDS at this link:

Reserve your spot →

A second code for $15% off (also offsite accommodation) is available for Design Better premium members. Link and code after the paywall below at the bottom of this post.

Friction and gratification

Holding a warm, hand-thrown coffee mug in your hand. Sharpening a carpenter’s pencil with a pocket knife. We usually treat the moments of sensory satisfaction that Ian calls gratification as rare, something you have to work yourself into a special state of mind to access. Ian argues the opposite. They’re not scarce at all. They’re everywhere, and the only thing standing between us and them is attention.

“One of the things I try to do in the book is to reframe that idea of, call it mindfulness, or noticing, into something that’s more like acceptance — just accepting these sensory gifts that the world is always delivering to you. And that transforms them from something scarce into something excessive. There’s just a surplus of them all the time. If you miss one, it’s no big deal, because another one will arrive right at its heels.”

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We’ve been to a lot of conferences over the years. You know the format: a speaker on a stage, a sea of seats, a hallway where the real conversations happen if you’re lucky enough to catch someone before they’re whisked away.

This isn’t that.

We’re partnering with our friends at September Works on the September Work(shop) Leadership Excursion, a two-day gathering of just forty design leaders in Sonoma this fall. The programming is intentionally conversation-first, which means the people you’ll hear from aren’t speakers who parachute in for a keynote and disappear—they’re part of the room. You’ll share meals with them, debate with them over a glass of Sonoma wine, and pick up threads from a morning session over dinner that night.

The theme: coalition building

Here’s the thing we keep hearing from design leaders: creating the design is often the easy part. Getting everyone behind it—your executive team, your cross-functional partners, the skeptics down the hall—that’s where it gets hard.

So we’re spending two days on coalition building, with voices from business, the arts, and politics who’ve done it in wildly different contexts:

Sheryl Cababa — Design strategist, founder of Optimistic Design, and author of Closing the Loop, on what a systems lens reveals about the art of bringing people together.

Bill Burnett — Executive Director of the Stanford Life Design Lab and author of Designing Your Life, on craft and meaning when the tools are changing this fast—and how to build something people want to be part of.

Molly Moon Neitzel — Founder of Molly Moon’s Homemade Ice Cream, who built a business and then used it to help change a city’s minimum wage policy. She’ll share who she had to bring together, who surprised her, and what didn’t work.

Paul Dichter — Writer and producer on Stranger Things, on what a decade inside that writers’ room taught him about turning colliding ideas into something greater than any one person could make.

Andy Allen — Founder of Not Boring Software, on building with conviction and how the community around his work shapes what he builds (and vice versa).

Andrew Evans — A designer-turned-magician, on the real-time trust that forms between a performer and a room full of strangers who’ve agreed to believe.

Why keep it small?

Because forty people can actually talk to each other. Small-group sessions and built-in community time mean you’re not collecting business cards—you’re building the kind of relationships that outlast the event. The whole thing feels less like a conference and more like a working session with people you genuinely want to think alongside.

And the setting doesn’t hurt. We’ll be at The Stavrand in Sonoma, with good food, a wine tasting excursion, a sit-down three-course dinner, and a few surprises we’re keeping under wraps.

The details

• When: September 28–29, 2026

• Where: The Stavrand, Sonoma, CA

• Who: Forty design and business leaders working to make design more impactful inside their organizations

• Tickets: Two options—$3,300 includes lodging at The Stavrand, or $2,200 if you’d rather book your own accommodation nearby. Both include all programming, meals, dinners, and the wine tasting.

Spots are genuinely limited (forty means forty), so if this sounds like your kind of room, don’t wait. We’ve already booked many of the tickets, with folks from Fortune 100 companies and brands you know and love.

We’ve got two discounts available for Design Better listeners and members.

The first is $100 off the event for those who book their own accommodation. Use code DBFRIENDS at this link:

Reserve your spot →

The second is $15% off (also offsite accommodation) for Design Better premium members. Link and code after the paywall below.

Need to make the case to your team? There’s a justification letter on the event page to help.

We miss seeing you in person. This is our excuse to fix that.

— Eli & Aarron

15% off tickets (book your own accommodation) for Design Better Premium Members

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A few years ago, Ian Bogost wrote what he thought was a throwaway Atlantic piece about how electric vehicles would finally kill the manual transmission. It went off like a bomb — and the reaction told him people weren’t mourning a car part. They were mourning the feeling of dropping a gear into place, a small moment of sensory connection quietly disappearing without anyone choosing to give it up.

That feeling is the subject of his new book, The Small Stuff. Ian calls it gratification — distinct from happiness or satisfaction, it’s the immediate sensory delight of communing with ordinary things: the ridged coffee cup, the click of an elevator button, the tink of ice in a water bottle. And he diagnoses what he calls dematerialization: the slow way efficiency, automation, and software have severed us from the physical texture of daily life.

A game designer, longtime Atlantic contributor, and philosopher of the everyday at Washington University in St. Louis, Ian has spent his career — across books like Persuasive Games and Play Anything — arguing that the systems we build carry values whether we intend them to or not. Here he turns that lens on the ordinary objects most of us stopped noticing long ago.

For designers, this is becoming more and more relevant. Ian argues that somewhere between the mid-90s and now, user-centered design quietly mutated into outcome-oriented design — we kept the language of user experience while the goals drifted toward the organization instead of the person.

But this isn’t nostalgia or a plea for friction. Gratification, he insists, is easy. It’s already happening to you all the time. The designer’s job isn’t to add friction, but to notice where the sensory life has quietly drained out of the things we build, and to re-introduce it. And the challenge he leaves us with is deceptively simple: get curious.

The Small Stuff is out now. You can find Ian at bogost.com.

Bio

Dr. Ian Bogost is a writer, designer, and scholar of media and technology. He is the Barbara and David Thomas Distinguished Professor and Assistant Vice Provost at Washington University in St. Louis. At WashU, he is appointed in three colleges and the co-executive director of the Office of Public Scholarship.

Bogost is also a contributing writer at The Atlantic and the founding partner of Persuasive Games LLC, a game and design studio. He is the author of 11 books, most recently The Small Stuff: How to Lead a More Gratifying Life. Bogost’s award-winning games and artworks, which include Cow Clicker and A Slow Year have been played by millions of people and held in permanent collections around the world, including at the Smithsonian American Art Museum.

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

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Turn It Over

This week on the show: Aaron Draplin, founder of Draplin Design Co., on origin stories, junk stores, and the kind of generosity that never makes it into a design portfolio.

Listen to the episode

Aaron Draplin: Spotify, Apple Podcasts, Substack, Youtube

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When Aaron Draplin was about ten, his dad snuck him through a fence into Detroit’s Olympia Stadium, the old home of the Red Wings, a few weeks before the building was demolished. They found their way into the locker room and his dad got down on his hands and knees and started ripping up the carpet. Draplin asked what he was doing.

“Aaron, this could be the carpet that Gordie Howe’s balls dripped on.”

They hauled out armloads of carpet, cut it into squares, and loaded a couple hundred loose bricks into the back of a minivan. For years afterward, his dad handed the pieces out to Red Wings fans like sacred relics. Draplin still has his.

That’s the kind of household Draplin grew up in. His dad pulled moldings out of Detroit houses before they were torn down, chased garage sale signs down dirt roads on the promise that this one could be the one, and once talked his way out of a hardware store with a pocket of things nobody had rung up. Decades later, Draplin still can’t walk past an estate sale without lifting one small thing into his own pocket, just to keep the tradition going.

He’s now one of the most recognizable names in American graphic design: the founder of Draplin Design Co., the guy behind Field Notes, a run of Nike and Ford work, and a U.S. postage stamp. We pulled three things out of this conversation that go beyond “cool logo guy.” How he thinks about identity. How he actually built his design education. What he thinks he owes the people around him now that he’s made it.

Learn how to make design more impactful in your org at a 2 day event in Sonoma, CA

Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Speakers include Paul Dichter, lead writer on Stranger Things, Bill Burnett, author of Designing Your Life, and Sheryl Cababa, author of Closing the Loop: Systems Thinking for Designers.

Learn more and register

1. He never ignored where he’s from

Most creative people, at some point, decide their origin story is something to outrun. Draplin didn’t. During his junior review at art school, a panel dressed him down for wanting to do “pedestrian” commercial work, like designing catalogs for a company such as Cabela’s, instead of chasing the high-concept polish that was fashionable in 1998. He didn’t take the hint. “I wanted to go into function,” he said. “You had to go make Cabela’s catalog for guys to buy big elephant guns. And that’s a vital job.”

What he’d actually grown up around wasn’t polish. It was hardware store aisles sorted into little bins of nails and screws. Garage sale tables covered in baby clothes and rusted signage. An extra refrigerator in the garage that his dad kept stocked with beer, joking, “Wisconsin might get tired of the jokes. If they ever invade over Lake Michigan, at least I have enough beer to get us through.” Salvaged Victorian oak furniture, scavenged lead type, Coca-Cola signs pried off buildings on their way to the wrecking ball. That was Draplin’s visual diet, and instead of trading it in for something with more art-school pedigree, he kept it.

“I didn’t need to detach from something to get to the next better thing.”

Read more

Hi folks! Aarron and I are taking a short summer break, so we’re rewinding to one of our favorite episodes from the end of last year with Aarron Draplin. Enjoy the episode, and we’ll see you next week with a new episode!

A larger than life figure in the creative world, Aaron Draplin has been designing everything from logos to posters since 1995. Few designers are as prolific as Aaron. He’s the founder of Draplin Design Co. (DDC). Priding himself on craftsmanship and quality, the DDC has made stuff for Field Notes, Esquire, Nike, Red Wing, Burton Snowboards, Ford, and he’s even designed a US stamp.

We caught up with Aaron in person at The James Brand studio in Portland, Oregon, where he walked us through an origin story that begins with a meteor in Navajo country and winds through the skate parks of Michigan in the 80s, the snowboard culture of the 90s, and eventually to one of the most recognizable voices in American graphic design.

But this isn’t just a conversation about making cool stuff—though there’s plenty of that. Aaron opens up about the work ethic he learned from his parents, and why being prolific isn’t about perfection—it’s about experimentation, and loving your work enough to show up every single day.

We talk about collecting, organizing thousands of ideas, and what it means to run a design practice where you can still work on your own terms. And throughout it all, Aaron brings the humor, the heart, and the hard-won wisdom of someone who’s never forgotten what it’s like to work a crappy job—and who reminds himself every day just how cool a life in graphic design really is.

Bio

Aaron Draplin was born in Detroit in 1973 and raised in the small village of Central Lake in Northern Michigan—population 800. After a brief stint at Northwestern Michigan Community College, he moved west to Bend, Oregon at 19 to chase the snowboarding life, and started designing graphics for Solid Snowboards. To fund his winters, he worked summers as everything from a traveling fair pizza wagon cook, to a dishwasher in Anchorage, Alaska.

He eventually returned to the Midwest to finish his design degree at Minneapolis College of Art and Design, before heading back west to become art director of Snowboarder Magazine in Southern California. In 2002, he moved to Portland to work as a senior designer at Cinco Design, where he worked on brands like Gravis, Helly Hansen, and Nixon.

In 2004, Aaron founded Draplin Design Co., working with clients ranging from Nike and Patagonia to Sub Pop Records and the Obama Administration. In 2009, he co-founded Field Notes with Jim Coudal and Coudal Partners—a collaboration that would become one of the most successful and beloved stationery brands in America. That same year, he gave his first public talk, which spiraled into a speaking career that’s now reached over 580 engagements worldwide.

His book Pretty Much Everything was published by Abrams in 2016 and is now in its 13th printing. At 51, Aaron continues to run his fiercely independent design practice from a backyard shop in Portland, Oregon.

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

Design Better Tea is also great on ice! 🧊 🫖

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Years ago, two friends in Philadelphia went looking for a parking lot. They’d been staring at the same six words on the back of their favorite jazz records for years — recorded by Van Gelder in Hackensack, and one Saturday they drove out to find it. They tracked the address down in a 1955 phone book. They pulled up expecting something. What they found was a parking lot for Hackensack Sports Stadium. No sign. No plaque. Nothing to mark that Rudy Van Gelder had turned his parents’ living room into a recording studio and quietly helped capture some of the most important American music of the century.

Chris Entwisle and Mark Havens had a quiet ride back down the turnpike. It’s also the reason WAIL: The Visual Language of Prestige Records exists. Unlike Blue Note, Prestige never got its design mythology — despite cover art that’s just as striking and just as durable. Entwisle and Havens spent two decades tracking down original pressings and interviewing designers before that history disappeared for good, and what they found was a label that ran, in one historian’s words, “like a mom-and-pop store” with no budget, no briefs, no marketing department and somehow produced a visual identity coherent enough to still echo through design today.

If you find yourself wanting for a fresh approach to your work, the Prestige record catalogue is a treasure trove of inspiration on how to use color, typography, and imagery in innovative ways.

Listen to the episode

Chris Entwisle and Mark Havens: Spotify, Apple Podcasts, Substack

Already a paid subscriber? Follow this link to set up you premium feeds on Apple, Spotify or any other platform from your phone or computer.

Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain — see the lineup and reserve your spot.

1. Nobody was hired to be a graphic designer

Let’s start with who these designers/artists actually were, because none of them set out to make album covers. Reid Miles trained at Chouinard and wanted to be an art director. Tom Hannan studied under Hans Hofmann and considered himself an abstract expressionist painter first. David X Young came to New York from Cape Cod to paint alongside Franz Kline and Willem de Kooning at the Cedar Tavern. Esmond Edwards was a freelance news photographer who talked his way into a session by offering to drive the musicians out to New Jersey.

Bob Weinstock, the label’s founder, didn’t have an art director because he didn’t have a staff to spare one. His hiring process was a portfolio and a hunch. “Tom Hannan just knocked one day and said, ‘Hi, I’m an art director,’” Weinstock remembered. “Bob Parent was a jazz photographer who was always hanging around. Whenever you needed a picture, you’d go to him.” There was no brief, no comp, no client approval — Weinstock vetted everything the same way, whether it was the music or the cover art. “I viewed it all as art,” he said, “the music and the covers.”

Prestige had none of that scaffolding, and it produced Esmond Edwards — a self-taught photographer who became, in Entwisle and Havens’s words, the label’s de facto creative director simply because he kept showing up and getting better.

“I viewed it all as art—the music and the covers.”

—Bob Parent

That freedom produced work that never even got the label’s blessing. David X Young — a Cedar Tavern painter who ran a jazz loft in the Flower District before he ever touched a record cover — designed this portrait of Lester Young for a rival label, Clef Records, using cut paper and a single word. It was rejected. Entwisle and Havens tracked down the original artwork decades later; it had never been printed.

The absence of a house style wasn’t a failure of management. It was the whole point. Each designer’s background — painter, photographer, sign-maker’s son — shows up directly in the work, because nobody was hired to execute someone else’s system. They were hired to have a point of view.

2. Limitations created opportunities

Reid Miles wasn’t even a jazz fan and he said so himself. What he loved was the blank 12-by-12 canvas and the fact that Prestige couldn’t afford to pay for art. “I only had type to work with,” he said, “and being a good designer, I guess I took advantage of the opportunity.” The result was the Thelonious Monk Quintets cover: the word MONK, split across two lines, filling the entire square in black type so large it reads as pure shape before it reads as language.

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Years ago, two friends in Philadelphia — both designers, both obsessed with jazz — kept noticing the same notation on the back of their favorite records: “recorded by Van Gelder in Hackensack.” So one Saturday they drove out to find it. They tracked down the address in a 1955 phone book, pulled up — and found a parking lot. No sign, no plaque, nothing to mark that Rudy Van Gelder had once turned his parents’ living room into a recording studio there, capturing some of the most important American music of the century.

That quiet drive home planted the seed for a twenty-year project. Mark Havens and Chris Entwisle are the authors of WAIL: The Visual Language of Prestige Records — the first real look at the design history of a label that, unlike Blue Note, never got its design mythology, despite cover art that’s just as striking and durable. They tracked down original pressings, interviewed the designers before that history disappeared for good, and uncovered how a label run, in one historian’s words, “like a mom and pop store” — no budget, no briefs, no marketing department — produced a visual identity coherent enough to still echo through design today.

Buy the book

What we love about this conversation is how much of it comes down to constraints driving creativity. Reid Miles couldn’t afford imagery, so he made typography the art. Tom Hannon had no budget for stock photography, so he shot the musicians himself. Designers got an album title and nothing else, and turned that absence of direction into creative freedom — because Bob Weinstock “viewed it all as art,” the music and the covers alike. This is a conversation about jazz, but it’s also about what happens to creative work when nobody’s watching too closely, and why limitations so often produce things that last.

Bios

Chris Entwisle is an artist and illustrator. For over thirty years, he has used his passion for both jazz and postwar graphic design in his illustration work. Entwisle has a BA in graphic design from Rutgers University. He and his wife live in the Philadelphia area.

Mark Havens is an artist and educator with a dual background in graphic and industrial design. His work has been exhibited internationally and is held in both public and private collections. Out of Season, his first major monograph, was described by the New York Times as “a decade-long elegy.” Havens is a professor of industrial design at Thomas Jefferson University.

Premium Episodes on Design Better

This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.

And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

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The Design Better summer reading list

As you head out on holiday this summer, it’s always nice to have a couple good reads tucked in a bag to pass the time. Our reading list this summer has nothing that would pass as homework. While you may not want to read books that take you back into work mode, these titles will get your wheels turning in new ways that just might make you look at design and technology with fresh eyes.

Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain — see the lineup and reserve your spot.

Aarron’s summer book recommendations

Frankenstein by Mary Shelley

Hollywood has done this book a disservice. The monster of film and Halloween costume is not the creature Shelley actually wrote: he is articulate, heartbroken, abandoned by his creator, and adrift in a world that refuses to see him. The real horror isn’t the monster. It’s Dr. Frankenstein’s hubris — his willingness to wield the power of technology without once pausing to consider what he’d set loose.

Two hundred years after its publication, that question feels newly urgent. The dialogue alone is worth the read. And it’s hard not to be a little awestruck knowing Shelley wrote it at 18, during the Napoleonic Wars, in an era when publishing was nearly impossible for women.

It’s a classic for a reason.

Zen and the Art of Motorcycle Maintenance, by Robert Persig

On the surface, this is a book about a father and son riding motorcycles across the American Northwest. Underneath, it’s one of the most serious attempts anyone has made to answer the question: what is quality, and why does it matter?

Pirsig’s narrator is obsessed in the best way with the relationship between a person and the thing they’re caring for. A motorcycle maintained with genuine understanding runs differently than one maintained by the manual. The difference isn’t mechanical. It’s philosophical. When you truly know something, you stop working on it and start working with it.

He calls this “gumption”, the psychic fuel that keeps a craftsperson going when the work gets hard. It’s not enthusiasm. It’s the willingness to stay present with a problem until it opens up.

That idea feels worth examining right now. As more creative work gets handed off to tools that can approximate quality without understanding it, there’s something clarifying about a book that insists expertise is not just useful, it’s a form of care, a discipline, and maybe even a moral obligation.

The Three Body Problem, by Cixin Liu

It’s easy, lately, to lose faith in us. The news does not help. And yet.

Liu Cixin’s novel — the first in a trilogy that became a global phenomenon — opens during China’s Cultural Revolution and builds toward one of the most unsettling premises in science fiction: an alien civilization has spotted Earth, and they’re on their way. They’ll arrive in four centuries. Humanity has until then to prepare.

What follows is a profound argument about what we actually are. The alien threat is assumed to be technologically insurmountable. Certain humans, confronted with this, decide the species isn’t worth saving anyway. It’s a seductive kind of despair, the feeling that our failures are too deep, too structural, too human to overcome.

The book demolishes that conclusion.

What makes us formidable turns out not to be our tools. It’s the way we think, our capacity to reason under pressure, to cooperate across impossible distances, to refuse the obvious answer when something in us insists there’s another one. Curiosity. Stubbornness. The willingness to stay in the problem.

A great summer read, and a useful corrective for anyone who’s been spending too much time doom scrolling.

Eli’s summer book recommendations

Endymion by Dan Simmons

This was a recommendation from DB guest Paul Dichter (Stranger Things writer). It’s part of Simmons’ Hyperion series, which I loved as a teenager. I’d revisited some of the earlier books in the series, but this is my first time re-reading Endymion, which explores themes that seem very relevant right now. It’s set in the far future, and explores what forms AGI might take, and what happens when technologies have their own motivations, and what happens when some are taken away from us.

Make Something Wonderful by Steve Jobs

A physical copy of this book was gifted to our graduating class of design students at Stanford this year. Hard copies can be hard to come by (though you can find them on eBay) but you can find the whole thing online for free too. As a kid who grew up playing games like Karateka, Lode Runner, and others on the Apple II, it was a nostalgic journey to read the oral history, emails, and other communications that his archive collected for this book. As a designer, it was interesting to see how much he cared about the design of his products from the very beginning (this quote is from a talk he gave at the Aspen design conference in 1983): We have a chance to make these things beautiful, and we have a chance to communicate something through the design of the objects themselves.

Rumpole on Trial by John Mortimer

This one is a bit far afield from the design and tech world, but sometimes we need a break from such things, and summer seems like a good time.

I'm not typically a fan of legal dramas, but I am a fan of British humor, and the poetry-quoting, “Chateau Thames Embankment” drinking barrister Rumpole is so entertaining that he makes even the inherently dry legal system in the UK entertaining.

“The main aim of education should be to send children out into the world with a reasonably sized anthology in their heads so that, while seated on the lavatory, waiting in doctor's surgeries, on stationary trains or watching interviews with politicians, they have something interesting to think about.”
—John Mortimer

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Niyati Gupta describes her career as one long experiment — deliberately putting herself in uncomfortable, ambiguous situations and treating every move as a personal learning loop. That instinct took her from a bachelor’s in design inside one of India’s most prestigious engineering colleges, where almost nobody understood what design was, to a research role at Carnegie Mellon where she studied health info needs for low-literacy users in rural India, to Autodesk’s bio-nano innovation lab building molecular visualization tools for scientists — and eventually to Google, where she joined the Next Billion Users team.

That team’s mission was to ask an open question: where would the next wave of users come from, what did they need, and what products didn’t exist yet to serve them? Niyati ran immersion sprints in the Philippines, India, Indonesia, and Mexico — shadowing users, building prototypes in the field, testing them in the wild, and bringing those insights back to a team that was building products like Camera Go and Google Files from the ground up. And she’ll tell you that the swim lanes between designer, engineer, and PM felt just as artificial out there in the field as they do today with AI accelerating everything.

These days she’s a senior product designer at Netflix, working on commerce and partnerships — which means thinking hard about discovery, about fandom, about how you help someone decide what to watch on a Friday night without making them feel like the choosing is harder than the watching. It also means designing across a ten-foot TV screen, a phone, and every device in between, and trying to make all of it feel like one seamless experience.

In this conversation, we get into what the Next Billion Users work taught her about designing for people who aren’t like you, how she thinks about influence as a designer — and why she’s convinced the title was never where the influence actually lived — and what Netflix’s design culture looks like from the inside, including how they run crits and how they think about A/B testing.

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Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

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