Know Your Shit with Josh Cadillac

Josh Cadillac
  • 5.0 (19)
  • Entrepreneurship
  • Updated Weekly

I am Josh Cadillac and welcome to my podcast KNOW YOUR SHIT. I've seen great success as well as seen the bottom in 2008. The one lesson I've learned is that for you to have success and differentiate yourself from everyone else, you need to KNOW YOUR SHIT. As a successful educator and investor in real estate and crypto, it drives me nuts that people do not immerse themselves in their craft. Everyone is so busy selling that they forget the most important thing: the product. I'll talk to the most successful folks in every industry, bring them to you, and show you the common denominator.

  1. 2d ago

    Stop Letting Your Emotions Control You | Janet Livingstone (Ep. 224)

    In this episode of the Know Your Sh*t Podcast, Josh Cadillac sits down with executive coach Janet Livingstone to talk about emotional regulation, self-awareness, and learning how to manage what’s happening beneath the surface. Janet explains why suppressing emotions doesn’t make them go away and how understanding your internal reactions can change the way you handle stress, disappointment, and difficult situations. She also shares how she uses these same tools while navigating the challenges of entrepreneurship. This episode gets into knowing yourself better, quieting your inner critic, and learning how to move forward without letting your emotions take control.

  2. Sep 23

    The Sales Mistake Killing Your Growth | Greg Woodward • EP 224

    In this episode of the Know Your Sh*t Podcast, Josh Cadillac sits down with entrepreneur and sales strategist Greg Woodward to talk about what actually drives business growth. Greg shares why entrepreneurs get in their own way, how confidence changes a sales conversation, and why you should sell an idea before spending months building it. They break down prospecting, finding the right customers, keeping your sales funnel full, and why businesses make bad decisions when they rely on emotion instead of enough data. Greg also shares his own journey from losing nearly everything to rebuilding his business and creating the freedom he was looking for. This episode is about selling smarter, staying in motion, and building a business the market actually wants.

  3. Sep 17

    223: What It Really Takes to Master Your Craft | Suede Michael Hussain

    In Episode 223 of the Know Your Sh*t podcast, Josh Cadillac sits down with Suede Michael Hussain, founder of Alpenhaus Shepherds, to talk about high performance, mastery and what it takes to build something at a world class level. Suede shares how buying a protection dog that could not actually protect him pushed him to study the industry at a much deeper level and eventually build his own company around real world protection dogs. The conversation dives into the obsession behind mastering a craft, learning from setbacks and staying committed when the process becomes brutal. Suede also explains why he sees failure as a gift, why truth is essential for high performance and how learning to think about the way you think can completely change your response to problems. This episode is about excellence, discipline and the mindset required to keep improving when good enough is not enough.

  4. Sep 2

    221: Why You Keep Getting Stuck | Coach Quinn Harwood

    In Episode 221 of the Know Your Sh*t podcast, Josh Cadillac sits down with professional coach and Growth Time founder Quinn Harwood to talk about confidence, identity and what it takes to keep moving when progress feels slow. Quinn shares how his own struggles with self doubt and imposter syndrome shaped his approach to coaching and eventually pushed him to help others grow in life, leadership and business. The conversation dives into how mindset shapes behavior and how repeated behavior eventually becomes part of your identity. Quinn also shares his experience losing everything after an early business venture failed and explains why discipline, curiosity and learning to identify your own growth gaps are critical when you are trying to build something for yourself. This episode is about building confidence, staying disciplined and becoming the version of yourself capable of reaching the goals you keep talking about.

  5. Aug 26

    220: Why Following the Expected Path Can Hold You Back | Dr. Florian Ilgen

    In Episode 220 of the Know Your Sh*t podcast, Josh Cadillac sits down with keynote speaker Dr. Florian Ilgen to talk about curiosity, change and building a life around what truly excites you. Florian shares how he went from earning a PhD in chemistry to becoming a magician, mentalist and international speaker while learning how passion can make change feel less intimidating. The conversation dives into what Florian calls "fearless curiosity." He explains why people become more open to change when they stop obsessing over the outcome and reconnect with the curiosity they had as children. He also discusses how passion affects the brain and why being deeply engaged in something can make fear and mistakes feel less powerful. This episode is a conversation about embracing change, following your own path and staying curious enough to discover opportunities you may never have planned for.

  6. Aug 19

    219: Why the Best Leaders Make Themselves Obsolete | Ted Santos

    What if becoming unnecessary is actually the sign of a great leader? Josh Cadillac sits down with Ted Santos to discuss turning chaos into growth, asking the questions nobody else is asking, and building teams that can succeed without depending on you. In Episode 219 of the Know Your Sh*t podcast, Josh Cadillac sits down with executive coach, business strategist, and turnaround expert Ted Santos to explore why breakthroughs often come from questioning what everyone else accepts as normal. Ted shares how he has helped CEOs create disruptive strategies, transform company culture, and navigate periods of rapid growth and chaos. After leading businesses through both explosive growth and declining revenue, he learned that chaos is not always something to avoid. When handled correctly, it can expose weaknesses, develop stronger teams, and create opportunities for growth. The conversation dives into why the best leaders do not always provide answers. Instead, Ted explains the power of asking better questions, challenging assumptions, and helping people see problems from perspectives they may have never considered. He shares how one client initially became frustrated because Ted would not simply solve his problems for him, only to later realize those questions were helping him uncover solutions no one inside his company had considered. Josh and Ted also discuss resilience, setbacks, and how difficult experiences can shape the way people lead. Ted opens up about losing both of his parents at a young age, taking responsibility for his younger siblings, and learning that people are capable of far more than they realize when circumstances demand it. That mindset eventually became central to the way he approaches leadership, business, and personal development. This episode is a thought-provoking conversation about leadership, navigating chaos, questioning conventional wisdom, overcoming setbacks, and learning how to bring out potential in yourself and the people around you.

  7. Aug 13

    218: Are You Working Too Hard? | Liz Landry

    In Episode 218 of the Know Your Sh*t podcast, Josh Cadillac sits down with organizational leadership consultant and entrepreneur Liz Landry to explore what happens when hard work is no longer enough to grow a business. Liz shares how she entered management as a teenager, overseeing employees and millions of dollars in revenue before eventually leaving the corporate world to start her own business. Despite knowing how to operate an established company, she quickly learned that building one from the ground up required an entirely different skill set. Within a few years, she found herself working 18-hour days, seven days a week, overwhelmed by a business that depended on her for everything. The conversation dives into why entrepreneurs eventually have to transition from being the operator who carries the business to the owner who builds the people, leadership, and systems that allow it to operate without them. Liz explains why the same work ethic that helps entrepreneurs build their businesses can eventually become the thing that holds them back if they never develop new leadership skills. Josh and Liz also discuss creating freedom before retirement, learning how to lead yourself when you are your own boss, and changing the way entrepreneurs view failure. Liz explains why every failure should be treated like tuition: understand what it cost, learn the lesson, and make sure you do not pay for the same mistake twice. This episode is a practical conversation about leadership, entrepreneurship, burnout, building scalable businesses, and making the transition from constantly working inside your business to creating something that can grow without depending entirely on you.

    218: Are You Working Too Hard? | Liz Landry

  8. Aug 5

    217: How Negotiation Helped Save $100 Million | Jorge Gayle

    In Episode 217 of the Know Your Sh*t podcast, Josh Cadillac sits down with negotiation trainer, entrepreneur, and Black Swan Group expert Jorge Gayle to explore how tactical empathy, trust, and curiosity can completely transform the way people negotiate. Jorge explains why successful negotiation begins before discussing money, contracts, or terms. By addressing negative assumptions, understanding the other person’s perspective, and making people feel heard, negotiators can lower defenses and create stronger long-term relationships. Josh and Jorge also discuss how these skills apply directly to real estate, where emotional decisions, financial pressure, and a lack of trust can easily prevent a deal from moving forward. Jorge shares how he discovered the Black Swan negotiation method while serving as JetBlue’s head of procurement. After being challenged to help the airline purchase 100 airplanes while saving $100 million, he began applying the lessons from Never Split the Difference and eventually brought Chris Voss to train teams across the company. Those skills helped JetBlue build stronger vendor relationships while reaching its savings goal ahead of schedule. The conversation also goes beyond business negotiations and examines the difficult negotiation people have with themselves. Jorge opens up about leaving a six-figure career, rebuilding after losing nearly all his income, facing possible bankruptcy, and using faith, gratitude, and discipline to begin again. He also shares how running ultramarathons has taught him to accept discomfort, do the hard things first, and keep moving even when the finish line feels far away. This episode is a practical and motivational conversation about becoming a better listener, building trust, handling emotional situations, overcoming setbacks, and developing the discipline to empty the tank in business and life.

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5
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About

I am Josh Cadillac and welcome to my podcast KNOW YOUR SHIT. I've seen great success as well as seen the bottom in 2008. The one lesson I've learned is that for you to have success and differentiate yourself from everyone else, you need to KNOW YOUR SHIT. As a successful educator and investor in real estate and crypto, it drives me nuts that people do not immerse themselves in their craft. Everyone is so busy selling that they forget the most important thing: the product. I'll talk to the most successful folks in every industry, bring them to you, and show you the common denominator.

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