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

    203: Stack the Odds in Your Favor W/ Joseph Rutakangwa

    In Episode 203 of the Know Your Sh*t podcast, Josh Cadillac sits down with Joseph Rutakangwa to break down the mindset, structure, and decision-making process behind building a life and business on your own terms. Joseph shares how success comes from stacking the odds in your favor—focusing on what you can control, minimizing downside risk, and making intentional decisions that compound over time. The conversation dives into why most people fail by trying to be everything at once, and how understanding your strengths—and limitations—is key to long-term growth. They explore the importance of discipline, self-awareness, and learning how to “play the hand you’re dealt” while constantly adjusting your strategy. Joseph also opens up about managing disappointment, staying focused through uncertainty, and why reflection and cause-and-effect thinking are critical to improving your results. This episode is a deep dive into ownership, structure, and building a life based on smart decisions—not luck.

    40 min

  2. 3D AGO

    202: From Employee to Investor Mindset | Ken Gee

    In Episode 202 of the Know Your Sh*t podcast, Josh Cadillac sits down with Ken Gee, real estate investor and private equity expert, to break down what it really takes to scale wealth through commercial real estate and strategic investing. Ken shares his journey from starting small to managing large multifamily deals, highlighting the importance of education, calculated risk, and surrounding yourself with the right people. The conversation dives into how to analyze opportunities, raise capital, and build systems that allow you to grow beyond trading time for money. They also explore the mindset required to transition from employee thinking to investor thinking, why patience and discipline are critical in today’s market, and how long-term strategy beats chasing short-term wins. This episode is a blueprint for anyone looking to level up from active income to true wealth-building through real estate and smart investing.

    37 min

  3. MAR 18

    201: The Reality Behind Building & Business w/Pat Miller

    In this episode of the Know Your Sh*t podcast, Josh Cadillac sits down with Pat Miller, entrepreneur, builder, and seasoned business operator, for a no-BS conversation about resilience, reputation, and what it really takes to build a lasting business. Pat shares lessons from the construction world and beyond, breaking down how dealing with adversity, managing relationships, and protecting your name are non-negotiables in business. They dive into the realities behind rising costs, the unseen pressures entrepreneurs face, and why playing the long game—focusing on repeat business over quick wins—is what separates true operators from everyone else. This episode is a raw look at grit, ownership, and doing business the right way, even when it’s harder.

    56 min

  4. MAR 17

    EP 200: Stop Resisting Change—Start Winning With It W/ Meredith Elliott Powell

    In Episode 200 of the Know Your Sh*t podcast, Josh Cadillac sits down with Meredith Elliott Powell—keynote speaker, consultant, and bestselling author—to break down how to turn uncertainty into your greatest competitive advantage. Meredith shares how her career across multiple industries during times of disruption led her to one core realization: change isn’t the problem—how you respond to it is. The conversation dives into why uncertainty creates opportunity, how market shifts eliminate weak competition, and why those who lean into disruption are the ones who win. They explore the importance of curiosity, listening to real customer problems, and building strategies that prepare you for what’s coming—not just reacting to what’s happening. Meredith also breaks down how to reframe rejection, stay focused in chaotic environments, and develop the mindset required to grow when others pull back. This episode is a powerful guide to navigating change, building resilience, and positioning yourself to win in any market—no matter how uncertain it gets.

    29 min

  5. FEB 25

    199: Why Consistency Beats Talent Every Time W/ Gary Daly

    In Episode 199 of the Know Your Sh*t podcast, Josh Cadillac sits down with Gary Daly to break down the mindset, discipline, and personal growth required to succeed in sales and entrepreneurship. Gary shares how surrounding yourself with the right people, developing self-awareness, and staying consistent through setbacks are the real drivers of long-term success. The conversation dives into handling rejection, managing expectations, and building the mental toughness needed to keep showing up—especially when results don’t come immediately. They also explore the importance of passion, continuous learning, and how small improvements over time compound into meaningful progress in both business and life. This episode is a powerful reminder that success isn’t about shortcuts—it’s about consistency, mindset, and doing the work when it’s not easy.

    25 min

  6. FEB 21

    198: The Truth About PR for Entrepreneurs | Mickie Kennedy

    In Episode 198 of the Know Your Sh*t podcast, Josh Cadillac sits down with Mickie Kennedy, founder of eReleases, to break down how small businesses and entrepreneurs can leverage media and press coverage to build real credibility—without wasting money on hype. Mickie shares how he built a company that helps startups and growing businesses access real journalists through strategic press release distribution. The conversation dives into what actually makes a story newsworthy, why most companies approach PR the wrong way, and how consistent visibility can compound into long-term brand authority. They also explore the entrepreneurial realities behind running a lean team, managing yourself through setbacks, and staying in the fight when growth isn’t linear. Mickie opens up about leadership, self-assessment, and the importance of long-term thinking in building a sustainable business. This episode is a practical guide to earned media, brand positioning, and understanding how credibility—not just marketing—creates lasting success.f2q

    35 min

  7. FEB 11

    197: The Competitive Advantage of Listening w/Christine Miles

    In this episode of the Know Your Sh*t podcast, Josh Cadillac sits down with Christine Miles, founder of The Listening Path, to unpack a skill most people think they have—but were never actually taught: how to truly listen. Christine shares the deeply personal story behind her life’s work, from growing up with a mother who struggled with mental illness to building a scalable, global listening education program now being implemented in classrooms and corporations worldwide. They explore why listening is the ultimate credibility builder, how misunderstanding quietly erodes relationships (“death by a thousand cuts”), and why entrepreneurs must learn to meet the moment while keeping their long-term vision intact. Christine also opens up about resilience through chronic pain, reinvention after adversity, and the mindset shifts that helped her keep going when results weren’t immediate. This conversation is a masterclass on empathy, leadership, grit, and the competitive advantage of making people feel truly understood.

    40 min

  8. FEB 5

    196: Making Your Money Work Harder Than You Do W/ Tom Dunkel

    In Episode 196 of the Know Your Sh*t podcast, Josh Cadillac sits down with Tom Dunkel of Eagle Investments to break down the realities of building long-term wealth through disciplined investing and strategic risk management. Tom shares insights from years of experience working with distressed mortgage debt, stabilizing assets, and building portfolios designed to perform across shifting market cycles. The conversation dives into one of the biggest misconceptions in investing—how avoiding risk can actually be riskier than investing—and why learning to make your money work for you is the foundation of financial independence. They explore how market uncertainty creates opportunity, the power of compounding over time, and why consistent investment discipline can outperform even high-income careers over the long run. Tom also discusses leadership, resilience, and the mindset required to navigate market shifts while staying focused on long-term wealth creation. This episode is a masterclass on investing psychology, strategic patience, and understanding how real wealth is built—not chased.

    33 min
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5
out of 5
19 Ratings

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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