The Advantages of Adapting with Richer Poorer Founder & CEO Iva Pawling

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To be an entrepreneur is to be constantly adapting. In a world where the market is ever-changing, it’s important to be able to shift, to refocus and rebrand… to be ready for whatever is coming next. Iva Pawling, the Founder & CEO of Richer Poorer, a California-based inner wear company with a cult following, knows a thing or two about having to think on the fly. 

“It was completely the opposite of what we expected, and they ended up filing for bankruptcy within thirteen months of acquiring us,” Pawling said of Richer Poorer’s ill-fated acquisition. “It was just insane. It really taught me to always have a Plan B. Like… if things don’t go how you plan, how are you handling it?” 

So how did she handle it? How did Richer Poorer survive huge obstacles like a failed acquisition, over-complicated marketing tactics, and a major supply-chain stallout? Find out on this episode of The Journey.

Main Takeaways:

  • Sometimes, it’s okay to not run on pure passion: The old saying goes something like this: “Motivation is for amateurs, discipline is for professionals.” There might come a time when a brilliant opportunity presents itself, but it’s not something that completely lights your fire. It’s not your dream. There are times when you might need to look at the bigger picture and think long-term. It might not be the most exciting thing, but maybe it’s the right next step. Successful careers take both passion and smart moves done at the right time.  
  • Pay if forward: When Iva was just starting out, she reached out to a lot of her contacts, all of whom were eager to point her in the right direction. That’s because, she explained, that all entrepreneurs have had someone do the same for them when they were just starting out. The business world can be very cutthroat, but it can also be full of camaraderie. Keep an eye out for those moments when you can help someone… it will come back to you, eventually.
  • Vulnerability can be a strength: Every business will face curveballs and moments of uncertainty. Good leaders will turn to their team and ask for help with blind spots instead of pretending to have all the answers. By being vulnerable, you invite your team to find the best solution.

Key Quotes:


“I never in a million years thought I would end up here, but I am so much more passionate about what we do now than when we were making mens’ socks. I love this product so much more and can connect with it. We all want to wear something we can get really passionate about.” 

“We pulled on some resources in the meantime… just contacts and cold calling people and asking them for help. That’s one of the biggest pieces of advice I give people starting out: ask entrepreneurs how they’ve gotten to where they are… it’s other people helping them It’s a natural ‘pay it forward’ feeling.” 

“Navigating through a few years of those transitions really taught me to always have a Plan B. Like… if things don’t go how you plan, how are you handling it?”

“We want to be the brand that people always come back to, that they know and that they like… when they’re feeling the best and most comfortable and doing the things that they love… they’re doing it in Richer Poorer.”


Iva Pawling is the daughter of immigrants and she and her sister Gorjana had an interest in brands and fashion from a young age. She started Richer Poorer with co-founder Tim Morse in 2010, a brand that creates men’s and women’s classic basics with elevated style. The innerwear brand’s mission since its 2010 start has been to create wardrobe staples with a California influence, that make dressing easy and living even more so. Richer Poorer is based in San Juan Capistrano, California and sold in over 800 retailers internationally.

This season of the Journey is produced by Mission.org and brought to you by UPS. To learn how UPS can help your small business, go to UPS.com/pivot.


Episode 116