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Episode 280

Little Luxuries with Caleb Ulffers | Win the Day
April 21, 2026
Caleb Ulffers is a product design expert and the internet’s favorite curator of “little luxuries” that inspire millions.
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In this episode of Win the Day:

“The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius

Caleb Ulffers is the internet’s favorite curator of “little luxuries.” But before he mastered the content game, Caleb leaned into his obsession with intentional living.

As founder of Haven Athletic, a company born out of frustration when he couldn’t find his headphones in a messy gym bag, Caleb turned a duct-taped prototype (made from a Nike duffel and cereal box cardboard) into a multimillion-dollar brand. It generated over $5 million in sales, partnerships with more than 100 professional athletes across the NFL, MLB, NBA, UFC, and CrossFit, and features in outlets like Sports Illustrated, GQ, TIME, and Vice.

At his core, Caleb is obsessed with intentional living—designing products, spaces, routines, and even his own mind to create more flow, clarity, and performance. He’s helped build startup ecosystems, produced nationally recognized conferences, exited companies in health and software, and taught product design to Fortune 500 teams.

More recently, he’s grown a content audience of over 250,000 followers by sharing his taste for “little luxuries” and thoughtfully curated consumer products—building both influence and six-figure brand partnerships along the way.

In this episode:
• When it’s time for you to take a different path in your life.
• How your environment shapes your energy.
• The blueprint to consistently go viral on social media.
• Why building in public accelerates trust.

Let’s WIN THE DAY with Caleb Ulffers!

Timestamps

00:00 Meet Caleb Ulffers: from $5M gym bag company to viral "little luxuries" creator
2:19 Growing up as the youngest of four in a tiny Nebraska town
4:08 What homeschooling taught Caleb Ulffers — and what it got wrong
8:20 The Starbucks moment: when the dream you were sold turns out to be a lie
12:52 How the startup world gave Caleb Ulffers a new path after corporate life failed him
15:05 Why experience is the product: lessons from designing a world-class conference
21:30 How to go viral on social media: the content formula behind 250K followers
30:00 The exact course and cheap home setup that launched Caleb's content career
33:07 How to design your life: AB testing, personality tests, and intentional routines
37:00 Why most people consume self-help content but never actually change
38:32 Too much consumption, not enough digestion — how to learn from what you consume
42:01 Why cutting out news, negative music, and draining people will make you happier
43:15 Why clarity — not motivation — is what actually moves you forward
46:21 What winning the day really means (and how the answer changes over time)
47:38 The best coffee products worth knowing about, according to Caleb Ulffers
49:31 The two daily affirmations that will completely change how you see hard times
52:30 Rocket round

 

Resources / links mentioned:

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⚡ Caleb Ulffers website

🕺 Caleb Ulffers TikTok

📷 Caleb Ulffers Instagram

📝 Caleb Ulffers LinkedIn

🌎 Caleb Ulffers X

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Inspiring quotes in this episode:
  • "I'm working at Starbucks making $17/hour and thinking, 'This isn't the dream that I was sold. I want something more. I want something better.'" — Caleb Ulffers
  • "I had always known that I wasn't going to climb the corporate ladder." — Caleb Ulffers
  • "One of my first key lessons in product design was all around experience. I learned that experience is the product." — Caleb Ulffers
  • "The vulnerability and bringing people into the messiness and the highlight reels of what you're doing accelerates trust, because they get to see behind the curtain." — Caleb Ulffers
  • "I've even worked with AI to try to help source products. But I'm just so particular on what a little luxury is." — Caleb Ulffers
  • "March 2025, I was like, 'All right, for this month I want to do a piece of content every single day.' One of the concepts I had was little luxuries. By the end of the month, I had gotten my first two videos to go viral. I was posting every single day, just paying attention to, 'What's working? What's not? How do I ship this?' Ship a video every single day and by the end of the month, got some traction." — Caleb Ulffers
  • "I want a video every day that hits 1 million views." — Caleb Ulffers
  • "One of the biggest hacks to life is saying, 'Okay, I can wait to change until the pain is so great that I'm forced to, or I can recognize I'm right here and the pain's not that bad yet, but it will get there and I can change right now.' Look at the future of your life and see what's going to happen." — Caleb Ulffers
  • "I'm a big fan of A/B testing. I learned that in marketing. Here's one thing, what's the outcome? Here's the other thing, what's the outcome? Then which outcome do you like? That's a really powerful tool to testing all of the biohacking. Rather than just being like, 'Oh, this is what you have to do.' I'm like, 'Well, just try it.'" — Caleb Ulffers
  • "There's too much consumption and not enough digestion." — Caleb Ulffers
  • "I don't hang around with people who are constantly talking about negative things or complaining." — Caleb Ulffers
  • "I have forged this path and I've brought myself to where I am." — Caleb Ulffers
  • "Movement without clarity is near impossible. It feels muddy, it feels bad, and you don't feel confident about it." — Caleb Ulffers
  • "The phrase is: 'I believe that everything is from the creator, is good, and is there to show me what to change.' Which really reframes everything that's going on in your life. That's something that pops up every day at 8:00 AM. I look at it and I read it out loud." — Caleb Ulffers
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