Working On Your Business (So You Can Actually Leave It) with Ral West

Working On Your Business (So You Can Actually Leave It) with Ral West

In this episode of The Chaotic Entrepreneur, Kimberly sits down with Ral West to unpack a wildly impressive entrepreneurial journey—from selling blackberries as a kid to building, systemizing, and selling a multi-million-dollar travel business. Highlights include: * Ral’s first taste of entrepreneurship (spoiler: blackberries + ladders) * Building a tourism and travel business connecting Alaska and Hawaii * What it really means to work on your business instead of in it * Why systems, SOPs, and company culture matter more than hustle * Scaling a business, implementing early tech, and reducing staff while increasing revenue * Preparing a business for sale—and knowing when to exit * Life after selling: cruises, real estate, and teaching others how to build sustainable businesses Ral shares timeless principles that still apply today—no matter how much technology has changed.

Owning the Chaos: Oil Tankers, Malls, and Millions Lost with Kevin Hipes

In this episode, Kimberly sits down with Kevin Hipes, a serial entrepreneur with decades of stories, wins, losses, and wildly unforgettable experiences. From owning an oil tanker in the Caribbean (yes, really) to redeveloping struggling malls, Kevin shares what it truly means to embrace chaos—and why failure might be your greatest teacher. * Why Kevin considers chaos his best friend in business * The infamous oil tanker deal that made (and lost) millions * How keeping cash in reserve saved him during major financial downturns * Why he celebrates failures just as much as wins * The mindset shift that made him fearless: “If you’re humble, you can’t be humiliated” * Knowing when to let go of what’s no longer fun in business * Why entrepreneurship isn’t for everyone—but is everything for the right person Kevin brings humor, honesty, and perspective that only comes from living a full, messy, bold entrepreneurial life. Connect with Kevin: * Book: Book of Me: The Life and Times of Kevin Hipes, the New York Forrest Gump (available on Amazon) * YouTube: Planet Hipes Stay bold. Stay chaotic. And maybe don’t buy an oil tanker without a backup plan. Highlights:

From Street Kid to Millions: Why Chaos Is the Real Cost of Entrepreneurship

In this episode of The Chaotic Entrepreneur Podcast, Kimberly sits down with Jerry Brazie, a serial entrepreneur with an extraordinary life story and decades of experience navigating real-world business chaos What we cover: * Jerry’s journey from growing up in extreme poverty to building multi-million-dollar businesses * Why entrepreneurship is not for everyone—and why that’s okay * The uncomfortable truth: business is chaos all the time, not just in the beginning * How growing fast without understanding cash flow nearly destroyed a thriving company * Why selling isn’t enough—you have to sell profitably * The mindset shift that changed everything: “Shut up and listen” * How success can be just as dangerous as failure if you stop learning * The power of peer-to-peer groups and finding people who are smarter than you * Why entrepreneurs must be “the rock everyone crashes against” * Jerry’s mic-drop analogy: entrepreneurship is like a prize fight—everyone has a plan until they get punched in the face Jerry also shares: * Why online “overnight success” stories are mostly fiction * How chaos should be embraced, not avoided * The advice he wishes every entrepreneur heard earlier * What he’s building next with The KRONOS Group, a peer-to-peer community for business owners navigating growth and chaos Connect with Jerry Learn more about Jerry and the KRONOS Group at thekronosgroup.org

Finding the Blessing in the Chaos with Dr. Chris Zaino

In this episode of The Chaotic Entrepreneur, we sit down with Dr. Chris Zaino for a raw, inspiring, and refreshingly honest conversation about chaos, resilience, and building success from life’s hardest moments. Chris shares how a life-threatening health crisis completely rerouted his path — from professional athlete and celebrity trainer to chiropractor, wellness entrepreneur, and high-level business consultant. What started as physical chaos became the foundation for purpose-driven entrepreneurship and massive impact. This episode is packed with real talk, mindset shifts, and practical tools for navigating the messy middle of business — without pretending chaos doesn’t exist. What You’ll Hear in This Episode * How a devastating health diagnosis became the catalyst for Chris’s entrepreneurial journey * Why chaos isn’t the enemy — and how to turn it into an advantage * The difference between chaos from struggle vs. chaos from abundance * Why “no one can call BS on your story” is a powerful business strategy * How losing his presentation forced Chris into authenticity — and changed everything * Simple daily routines that ground you when business feels overwhelming * Why physical movement is one of the fastest ways to reset your mindset * The importance of celebrating wins (before burnout reminds you the hard way) * How patience and timing can be just as powerful as action * A quick-fire metaphor that perfectly sums up entrepreneurship (hint: it involves racing) Connect with Dr. Chris Zaino https://www.instagram.com/drzaino

Chaos Builds Character with Richard Blank

In this episode of The Chaotic Entrepreneur Podcast, Kimberly chats with Richard Blank, founder of Costa Rica’s Call Center. From Philly streets to tropical boardrooms, Richard shares how chaos shaped his success. They dive into bold risks, cultural curveballs, and the messy magic of running a business without losing your cool (or your humor). Highlights: * From Philly to Costa Rica — how Richard built an international call center from scratch * Why chaos isn’t the enemy—it’s the ultimate teacher * Leadership through vulnerability, apologies, and staying human * Turning flops into fuel (like that time he ran out of gas with a client 😅) * “Pura vida” vs. hustle culture—and what it really means to slow down His mantra: replace pressure with boldness and play the long game Richard is the CEO of Costa Rica’s Call Center and a master at blending culture, communication, and chaos into lasting business success. You can find him at costaricascallcenter.com [https://costaricascallcenter.com/] — mention Kimberly for personal advice