Jeff Sheldon - Creating a Unique Brand by Following a Dream

My Big Story

How a graphic designer turned a t-shirt making experiment into a full-time, successful business, creating products, loyal fans don’t want to live without


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Today’s guest is Jeff Sheldon, founder of Ugmonk, a brand that creates smartly designed apparel, work, and lifestyle products. Jeff’s engaging story includes the start of Ugmonk, where he experimented with an idea to bring to life, high-quality, unique items with a modern aesthetic. By designing just a few t-shirts, to see if they’d sell — a couple of years later, he’s working on this experiment full time now, running a well-loved company and brand for nine years.

Jeff and Christopher talk through Jeff’s story from a designer to a business owner, with highlights like adding a social good element to his business; why Jeff is so transparent with his followers; starting a family and balancing work-life; and the things that hold him back.

Jeff appears to be an average guy who is experimenting, learning, and enjoying his journey. Of course he is clearly talented — creating wonderful products, but he’s also proof that we can follow a dream, do what we love, and also goes to show us, nice guys actually do win.


Key Takeaways

[1:50] How would Jeff describe his work?
[4:12] How Jeff use his talents and interests to be both the designer and the entrepreneur in his business.
[7:10] This is what makes Ugmonk different than other companies or designers.
[9:17] There’s a reasons Jeff has to promote his work even when he doesn’t really want to talk about himself. Also, there are people that have inspired Jeff’s business approach.
[11:16] How did Jeff’s story begin?
[13:18] Jeff’s small community of committed fans kept him going and helped him to make the leap into full-time business.
[14:49] Jeff shares that you don’t need a huge fan following or dollars and cents to follow your passion and make it a reality.
[16:40] How doubts can surface when Jeff’s in the the thick of working in his business.
[18:40] Jeff is becoming more transparent and sharing more of the backstory from a business owner’s perspective.
[22:26] What has changed at Ugmonk over the past nine years?
[26:15] How Jeff is working toward a new product, and the challenges he faces still, with making it happen.
[28:26] Jeff talks about his interest in giving back, and why he decided to get involved in Rice Bowls charity.
[32:06] People overthink things to the point that they get paralyzed. Jeff encourages people to start small and see what people say.
[33:09] Since Jeff is so involved in his business, he talks about balancing his family and business.
[35:43] These are the things that hold Jeff back or gets in his way from moving forward.
[38:31] What can we learn from Jeff’s story?
[41:32] Where to find Jeff online.
[42:27] What did you think? Any new ideas or questions? I’m always left with new ideas and feel energized after these conversations with guests. Speaking of being energized, did you know about my Awesome Finds Newsletter? Each week I share creative spotlights, meaningful stories, and new ideas to spark your imagination. I want to share the great stuff in the world that energizes me that will energize you. Sign up and find out more at
[43:12] Call us at 1-707-347-9312 to share ideas, stories and feedback. Also, we have even more content, stories and ideas at Here’s how to connect and find out more.
[43:33] Follow Christopher online at @mechristopher on Instagram and Twitter.


Mentioned in This Episode

@mechristopher on Instagram
@mechristopher on Twitter
@accidentalinformation on Instagram
Accidental Information on Facebook
@accidentalinfo on Twitter
Email Jeff
@ugmonk on Twitter
@ugmonk on Instagram



“I’m a designer by trade and an entrepreneur by accident.”

“I have intentionally stayed small.”

“Brands mature out of that infant stage and I’ve found, ‘why should I grow out of that?’ when that’s something unique…”

“There is something unique about people saying, “I have followed your work for six years; I feel like I know you.”

“The ‘aha’ moment was really the fact that there were people out there that resonated with what I was doing.”

“My very small community of fans were the reason and the motivation to keep going.”

“You don’t need everyone to like what you’re doing.”

“If I stopped doing this, then people would miss it and that makes me feel valued; kind of in a selfish way.”

“There is something about learning something I don’t know, that I’m addicted to.”

“Solve my own problems or things that I actually want; that actually have utility and design, and do it in an Ugmonk way.”

“If you don’t start, you don’t know what will happen.”

“You don’t necessarily need all of the pieces perfect in order to try.”

“It’s all going to look different for everyone.”

“Think about it from the ‘why’ perspective; why do you want to start this?”



Take a tour of the Ugmonk Studio here

Watch the Ugmonk story