Craft Over Scale: The Quiet Pursuit of Meaningful Work with Jeff Sheldon

This week, I talk with Jeff Sheldon, designer and founder of Ugmonk. Jeff’s story is about more than building a successful brand—it’s about choosing craft over scale and staying true to what you love. We talk about why he turned down Shark Tank at the peak of a viral Kickstarter, how his childhood love of drawing grew into a career in design, and what he’s learned about perfectionism, entrepreneurship, and the emotional cost of mastery. We also explore the quieter parts of his journey: the role his marriage has played, his philosophy of work and life, and how he continues to create intentionally 16 years in. If you’re trying to make meaningful things without losing yourself in the process, this conversation is for you. Let’s get to it.

Partner Deals

Proper: Save $500 off onboarding when you mention Good Work at https://workwithproper.com.

In this episode:

(00:00) – Intro
(01:55) – Why Jeff turned down Shark Tank
(04:35) – The foresight behind saying no
(06:59) – Jeff’s philosophy of work and life
(10:04) – First steps into design
(13:08) – Nurturing creativity
(19:13) – Why Jeff doesn’t call himself an entrepreneur
(25:49) – A relentless standard of excellence
(34:46) – The emotional cost of mastery
(42:48) – Doing vs. learning on the internet
(46:43) – Partnership and support
(54:15) – Keys to a lasting relationship
(01:01:00) – Winning his first t-shirt contest
(01:04:31) – From $18k goal to $430k raised
(01:08:06) – Gather vs. Analog
(01:16:08) – Success without wealth
(01:22:30) – The tradeoffs of a bespoke business
(01:25:03) – Lessons from early struggles
(01:32:36) – Holding to an ethos in a bigger culture
(01:35:56) – Becoming world-class
(01:39:34) – Jeff’s most beautiful future
(01:40:35) – Who Jeff is becoming

Key Takeaways

Learn to Say No, Even to Big Opportunities. Jeff turned down an invitation to appear on Shark Tank at the height of momentum from a Kickstarter campaign. He recognized that scaling too quickly or chasing exposure would pull him away from the creative work he loved. Don’t say yes just because something looks glamorous—say yes only to opportunities that align with your long-term goals and values.
Build Your Work Around What You Love. From his earliest days designing t-shirts, Jeff built Ugmonk around his passion for design and making things he personally enjoyed. Instead of separating work from life, he intentionally blended them so that his daily work reflects his interests and creativity. Design a career where your work fuels the life you want, not just your weekends.
Excellence Comes From Competing With Yourself. Jeff attributes his high standards to an internal drive—not to beat competitors, but to improve his own craft. Whether sketching for hours as a kid or obsessing over tiny product details, he always aimed to push his personal bar higher. Compete against your past self, not others, and let curiosity and craftsmanship set your standard.
Progress Requires Doing, Not Just Learning. Jeff pointed out how easy it is today to consume endless YouTube tutorials or courses and feel like you’re making progress—without ever starting. He stressed that the only way to grow is to put in the reps, fail, and try again. Stop over-preparing and start creating; action beats theory every time.
Strong Partnerships Make the Journey Sustainable. Jeff credits much of his success to the support of his wife, Mandy, from folding shirts in their apartment to encouraging him through setbacks. They’ve built trust over years and learned to navigate differences through tools like the Enneagram. Behind every thriving entrepreneur is often a partner who provides stability, encouragement, and balance.

Quotes

“I feel like the competition is against myself to be excellent. And then the rest of it is more subjective for people to say this is excellent or this isn’t. And that shows through, hopefully, in my work today and the products that people have sitting on their desk that I’ve designed. They’re seeing that excellence and seeing that refining of the details and the obsession over the smallest thing.” ~ Jeff Sheldon

“I would say I’m wealthy in that sense of the way the business has integrated with my life and the life that I want to live and that I get to be home with my kids, having dinner with my family. I get to spend the time with them. I get to do the things that I want my life to look like and be able to afford that.” ~ Jeff Sheldon

“A light bulb went on when I started to realize the exact same kind of emulation that I was doing with these pencil drawings would happen when I started to open up my first Adobe Illustrator or Photoshop, and didn’t know what any of the tools meant, but I saw the examples that people were creating with them and I was like, man, I wonder how are they doing that in Photoshop?” ~ Jeff Sheldon

“Mandy has played a huge role in supporting me and has always been encouraging me to keep going. It’s never been like this voice of doubt that’s coming over my shoulder that’s constantly pushing back. She’s always been really supportive and encouraging, and I know that not everybody has that, but that’s a huge asset to have.” ~ Jeff Sheldon

Links