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