This week on How Success Happens, I got to sit down with Emmy-winning designer and Queer Eye star Bobby Berk. Bobby is someone who is really, really, really good at making everything look stylish, comfortable, and beautiful. If you watch the video above, you’ll see that it is not exactly my strong suit, but he made a strong case why I, and any fellow slobs out there, might want to clean up our acts.
Bobby has built a seriously successful brand around his skills in front of and behind the camera: he has a new show, Junk or Jackpot?, he runs his own design firm, he wrote a bestselling book, and has a growing portfolio of boutique retreat properties, including the insanely gorgeous Casa Mallorca and Casa Tierra. In short: Bobby Berk works!
We broke down his journey so you can redesign your own plan for success in three, two, one!
Listen to Bobby’s Episode
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Three Key Insights
1. Your Space Is Quietly Making or Breaking You
Bobby doesn’t see design as “throw pillows and pretty paint”—he sees it as mental health infrastructure. “I wrote a whole book about how good design is good for the mind,” he says, explaining how light, color, and organization directly affect your mood, focus, and ability to function. He tells a great story about being five years old in Missouri, hating his all-red bedroom without knowing why, and using his birthday checks to buy blue curtains and bedding because “blue made me feel better.” His message to people who feel intimidated by design: it’s not about making your place look like a magazine—it’s about creating a space that actually supports your life, scientifically and emotionally.
Takeaway: Treat your home or workspace like a tool for your mental health—change one thing (light, color, or clutter) this week to make it easier to feel and work better.
2. Use Bad Jobs as Your Best Business School
Bobby left home at 15, never finished high school, and bounced from telemarketing to Bed, Bath & Beyond to a furniture company that routinely bounced paychecks. On payday, he says it became “a race to the bank” because if you didn’t cash your check first, it would bounce. It happened so often that check-cashing places eventually banned the company’s checks altogether. At Bed Bath & Beyond, he was fired for using the company fax machine to send his resume to West Elm, a story he now laughs about but clearly used as fuel. Those awful experiences shaped how he leads: “I learned that I would never treat my team like that,” he says. In good financial times and during times of stress, he puts a premium on making sure his team feels safe and secure.
Takeaway: Instead of just escaping bad employers, document what feels wrong and turn it into a personal rulebook for how you will treat your team and run your own business.
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3. Say Yes, Then Figure It Out
When Bobby launched his design firm, his first big client asked if he could handle full ground-up home design—construction documents, permits, the whole thing. “I didn’t know how to put together construction documents, but when they asked me if I could do it, I said, yes, of course I can do it. And I figured it out,” he says. He’s careful to add a caveat to that philosophy: “If you’re in an interview to be a doctor and you’re not a doctor, you should definitely say no.” But for most entrepreneurial opportunities, especially early on when you lack a “proper” pedigree, he believes the key is to make people want to work with you by being kind, humble, and relentlessly resourceful.
Takeaway: When a stretch opportunity comes along that’s safely learnable, say yes first—and commit to figuring it out fast and delivering like a pro.
Two Free Resources to Learn More
- You can follow Bobby’s design, wellness, and retreat adventures—along with his properties like Casa Tierra and Casa Mallorca—on Instagram.
- Learn more about how your workspace’s design affects your ability to collaborate effectively.
One Question to Ponder
If you redesigned just one part of your life—your space, your schedule, or your work—so it genuinely supported the person you want to become, what would you change first and why?
Email your answer to howsuccesshappens@entrepreneur.com, and I’ll read some of my favorites on a future episode.
About How Success Happens
Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.
What part of Bobby’s story do you want me to dig into more in future episodes—his retreat properties, his hiring philosophy, or his “say yes and figure it out” approach?
This week on How Success Happens, I got to sit down with Emmy-winning designer and Queer Eye star Bobby Berk. Bobby is someone who is really, really, really good at making everything look stylish, comfortable, and beautiful. If you watch the video above, you’ll see that it is not exactly my strong suit, but he made a strong case why I, and any fellow slobs out there, might want to clean up our acts.
Bobby has built a seriously successful brand around his skills in front of and behind the camera: he has a new show, Junk or Jackpot?, he runs his own design firm, he wrote a bestselling book, and has a growing portfolio of boutique retreat properties, including the insanely gorgeous Casa Mallorca and Casa Tierra. In short: Bobby Berk works!
We broke down his journey so you can redesign your own plan for success in three, two, one!
