Hey folks,
Welcome back to Everyday Empires, where I chat with everyday people building ventures of their own and unpack how they did it.
Today, I’m excited to share something new with you. Usually I bring you written interviews, but today I’m bringing the first episode of the Everyday Empires Podcast. You can watch and listen above or via the Substack app. I’m also planning to upload to YouTube, Apple Podcasts, and Spotify, but that might take a day or two. Let me know what you think 🫶🏼
For this episode I sat down with Matthew Smith, founder of Wimp Decaf Coffee Co.
He’s led design at several startups, founded multiple ventures including Really Good Emails, and most recently led design as a partner at Bunsen Studio, a powerhouse creative studio serving science and frontier technology companies. Matthew is one of the best designers in the world and a veteran entrepreneur with experience across a range of industries.
This summer, when I saw him post about starting a decaf coffee company, my initial thought was something like, "wait, what?” Then I clicked through to the Wimp Coffee website and it all made sense. The brand work, from the name to the illustrations and the copywriting was all just so good. This wasn’t your ordinary coffee company. Through Wimp, Matthew was branding his own values. He was rejecting hustle culture, following his intuition, and betting on himself. Most importantly, he was having fun.
I smiled, nodded, and subscribed to the mailing list. And then the goods kept coming. The email drips were a masterclass in brand building. So on launch day I purchased my first bag of Wimp Coffee (the Kahlo roast), and then I did what I do best here at Everyday Empires and sent Matthew an email asking if he’d like to chat so I could get the backstory and learn how he brought Wimp to life.
We talked about
The “why” behind Wimp and the problem with decaf coffee
The first steps he took to go from an idea to a real company
Why he started with brand
The timeline from idea to launch
Why he left a role he loved to start Wimp
How he uses AI for decision-making and idea validation
Links and resources
Decisive by the Heath Brothers. Matthew refers to this book when talking about making key decisions, such as which business idea to pursue.
Made to Stick. Another book by the Heath Brothers that Matthew mentions.
The Focus Course by Shawn Blanc. Matthew mentions how it was through this course that he had the epiphany that Wimp could be his main thing, and ultimately decided to leave his role at Bunsen to pursue Wimp.
jetpacksandrollerskates is the illustrator Matthew hired to bring Kuma, the Wimp mascot, to life.
Matthew’s business partners: Matt Patch (the roaster), Elijah Richards (the e-com guy), and Liam Tucker (the dev guy).
“Meet the next Liquid Death,” an interview with Matthew that goes deeper on the brand work
Keep reading for a written version of our chat (edited for brevity) and my key takeaways…
The “why” behind Wimp Decaf Coffee
Ken: What sparked the idea for Wimp?
Matthew: I’ve always loved coffee but struggled with the effects of caffeine. After I quit drinking alcohol, caffeine started to feel like another source of anxiety and stress. One day, I was sweating while just typing on my computer and realized I needed to make a change. Cutting out caffeine led to better sleep and less stress, but decaf options were terrible. Most decaf uses low-quality beans and harmful chemicals like methylene chloride, which made me think—why isn’t there a decaf coffee that’s high-quality and free from all that junk? That’s when Wimp was born. I saw brands like Athletic Brewing and Liquid Death blowing up in niches, and thought: why not decaf?
Cutting out caffeine led to better sleep and less stress, but decaf options were terrible… that’s when Wimp was born.
Starting with brand
Ken: A lot of entrepreneurs focus on building a product first, but you started with branding. Why?
Matthew: For me, brand is what makes something real. The typical advice is to build a prototype or MVP first, but branding helped me clarify what Wimp was about. It gave me direction, and it was fun—something that energized me after long days in my previous agency life. I wanted Wimp to embrace the idea that decaf isn’t for the weak—it’s for people who value being present, connected, and balanced in life. The name “Wimp” flips the narrative on its head, and our mascot, Kuma, a playful bear, embodies that spirit of fun.
The decision to go all in
Ken: You were successful in your design career. What made you decide to leave it behind for Wimp?
Matthew: It came down to realizing I wasn’t on the path I wanted for the next five years. I was in a course with Shawn Blanc, working on my agency, when he asked us to envision our ideal work life in five years. When I looked at my current trajectory, it didn’t align. I wanted more control, fewer meetings, and to work on projects that truly inspired me. Around the same time, I was tinkering with the idea of Wimp, and it hit me—this wasn’t just a side project, this was the thing. I decided to take the leap and build something that aligned with my values.
I knew I had to change because the path I was on wasn’t going to lead me to the future I wanted. I realized Wimp wasn’t a side project—it was the project.
From idea to launch
Ken: What were the first steps you took to make Wimp a reality?
Matthew: I spent six months playing around with branding, building a Pinterest board, and sketching out ideas. I reached out to an illustrator I admired and to bring our mascot, Kuma, to life. The moment I decided to go all-in, I started looking for the right people to work with—like a skilled roaster and an operations guy to handle e-commerce. I wanted to work with people who were smarter than me in their respective areas.
Using AI to make decisions
Ken: You mentioned using AI to validate ideas. How do you incorporate it into your process?
Matthew: I use AI to interrogate my ideas. I’ll ask it to challenge my assumptions, using frameworks from books like Decisive by the Heath Brothers. AI helps me look at things from different angles, asking questions like “What would make this idea a ‘yes’ or ‘no’?” It’s like having a thousand brains on tap to help me stress-test ideas. AI doesn’t replace talking to people, but it’s an incredible tool for brainstorming and validation.
Key takeaways
1. Lean into your story
Matthew’s personal journey—getting sober, quitting caffeine, and improving his mental health—directly influenced Wimp’s mission. He leaned into the narrative of decaf being for “wimps” and flipped the script, making it a lifestyle choice that prioritizes presence and well-being.
2. Brand before product can be a winning strategy
Most entrepreneurs rush to build a product, but Matthew started with brand. By creating a brand that resonated with his values and vision, Wimp’s identity became crystal clear before a single bag of coffee was roasted. This strategy gave him a clear direction and helped build early momentum.
3. Trust your gut, but validate with AI
Matthew uses AI as a decision-making tool, asking it to challenge his assumptions and validate his ideas. By leveraging frameworks from books like Decisive, he ensures his decisions are well-rounded and thoroughly thought through.
4. Take the leap, even if you’re a beginner
Though Matthew had no prior experience in the coffee industry, his design and branding expertise gave him the confidence to dive in. He surrounded himself with experts, from roasters to e-commerce pros, and wasn’t afraid to start from scratch.
That’s a wrap
A massive thank you to Matthew for sharing his time with me! Before you go, visit the Wimp website, scope out the branding, order some decaf, and give them a follow:
The Wimp website: https://www.wimpdecaf.com/
Matthew’s favorite roast: The Kubrick
Follow Wimp on Instagram
Follow Matthew on LinkedIn and Twitter where he regularly posts from behind the scenes as they grow Wimp
If you enjoyed this, you can support Everyday Empires by taking a moment to:
❤️ Like this post to get it in front of more future founders
💬 Reply or comment to share your thoughts or ask a follow up question
📤 Forward this post to someone who’d benefit from it
See y’all next time,
Ken
Everyday Empires: Matthew Smith of Wimp Decaf Coffee Co.