Out Of The System

Leo Climaco
  • 5.0 (2)
  • Entrepreneurship
  • Updated Weekly

Out of the System – Stories from Those Who Broke the Rules and Won Empowering entrepreneurs who choose to walk a path outside the norm. In this segment, we dive into real strategies, insights, and success stories that challenge the traditional system and push your business to the next level. From innovative marketing tactics to authentic leadership principles, we provide practical advice for those ready to grow with independence and intention. 🎧 Tune in weekly to gain the knowledge and inspiration you need to accelerate your journey to success on your own terms.

  1. 1d ago

    The heart attack that turned a broke man into a millionaire | Dan Sachkowsky

    Dan “Big D” Sikowski made millions before the age of 24 — and lost it all in the same year. In this episode of Out of the System, Leo Climaco and Dan “Big D” Sikowski discuss entrepreneurship, leadership, discipline, legacy, and the realities of building successful businesses. They discuss: • How Big D built and sold multiple companies after a childhood marked by rejection• The “ignorance on fire” mindset that helped him make millions in construction and direct sales• Why money, status, and external success left him feeling unfulfilled• The heart attack at age 40 that completely changed his perspective on life and business• Transitioning from operator to CEO through systems and processes• Breaking generational cycles and creating a meaningful legacy• The difference between motivation, desire, and discipline• Why authenticity matters more than image in entrepreneurship This episode explores business growth, personal transformation, leadership, and what it truly means to build a life of purpose and impact. Follow Out of the System: Instagram⁠@leoclimacopodcast⁠ TikTok⁠@leoclimacopodcast⁠ YouTube⁠@leoclimacopodcast⁠ Official Website⁠Out of the System⁠ Dan “Big D” Sikowski:⁠@_big_dan_official⁠

    1h 5m

  2. 5d ago

    From Depressed at 14 to Meeting Trump | David Townshend

    David Townsend grew up surrounded by addiction, depression, and adversity. At 14 years old, he found himself in a dark place, searching for a way out. Instead of following the path that consumed many people around him, he chose a different direction. Today, he is a journalist, biohacker, entrepreneur, and founder of Soulmatch AI, connecting with presidents, global leaders, and some of the most influential people in the world while helping others build deeper human connections. In this episode of Out of the System, David shares his journey of overcoming depression, building meaningful relationships, and creating a mission-driven company focused on connecting people at the soul level. They discuss: • Healing depression naturally and overcoming adversity at a young age• Growing up around addiction and choosing a different path• His encounter with President Trump and leaders from across Latin America• Building Soulmatch AI and the future of human connection• Biohacking, longevity, and optimizing performance• Open-mindedness and why it is one of the most underrated skills today• Artificial intelligence, prompt engineering, and the future of work• Conscious capitalism and solving global challenges through innovation• The difference between being a human doing and a human being This episode is about resilience, human connection, entrepreneurship, personal growth, and creating a life beyond your circumstances. Follow Out of the System: Instagram@leoclimacopodcast TikTok@leoclimacopodcast YouTube@leoclimacopodcast Official WebsiteOut of the System David Townsend:@davidtownshend1

    53 min

  3. Jun 2

    The Woman Who Built a Vodka Empire for Athletes — No Partners | Grace Gillespie

    Grace Gillespie spent four years researching and developing a cleaner vodka after noticing that many of her fitness clients were going to drink regardless of what they were told. Today, she is the CEO of Muscle Vodka, owner of three distilleries, and has expanded into 37 U.S. states and 14 countries—all without investors or business partners. In this episode of Out of the System, Grace shares her journey of building a global spirits brand from scratch, her commitment to discipline and faith, and the mindset that helped her create a company she owns 100%. They discuss: • The four-year research and development process behind Muscle Vodka• Building and scaling a spirits company with no outside investors• The challenges of operating in one of the world's most regulated industries• Private labeling for celebrities, NFL and NBA athletes, and influencers• Sales, persistence, and lessons learned from her father• Her perspective on GLP-1 medications and the pursuit of shortcuts• Faith, fear, and maintaining conviction through adversity• Extreme discipline, fitness, and pushing personal limits This episode is about entrepreneurship, ownership, discipline, faith, and what it takes to build something entirely on your own. Follow Out of the System: Instagram@leoclimacopodcast TikTok@leoclimacopodcast YouTube@leoclimacopodcast Official WebsiteOut of the System Grace Gillespie:@fitnessbygrace1

    1h 11m

  4. May 29

    Child Actress, Hollywood Abuse & Spiritual Healing | Hilary Momberger

    In this episode, Leo Climaco sits down with Hilary Momberger-Powers for a profound conversation about childhood trauma, survival, healing, spirituality, and the journey of reclaiming your life after unimaginable adversity. Hilary was the voice of Sally in Peanuts (Charlie Brown), appeared in more than 100 commercials as a child, and later worked as a script supervisor on over 350 productions, including major Hollywood projects such as Fast & Furious and The West Wing. Behind the success, however, was a story of abuse, addiction, neglect, and resilience. They discuss:• Growing up with a narcissistic and alcoholic mother• The hidden realities of being a child actor in Hollywood• Childhood trauma and its lasting impact on identity• The three core trauma responses: people pleaser, loner, and controller• How unresolved trauma quietly shapes adult behavior• The concept of "Trauma Uber Drivers" and subconscious patterns• Addiction, overdose, and hitting rock bottom• Forgiveness, acceptance, and healing family wounds• Spirituality as a path to recovery and transformation• Lessons from Kabbalah, Christianity, Islam, Hinduism, and Sufism This episode is about resilience, healing, self-discovery, and finding meaning beyond even the most difficult life experiences. Follow Leo Climaco: Instagramhttps://www.instagram.com/leoclimacopodcast/ TikTokhttps://www.tiktok.com/@leoclimacopodcast YouTubehttps://www.youtube.com/@leoclimacopodcast Official Websitehttp://leoclimacopodcast.com Hilary Momberger-Powers:https://www.instagram.com/hilarymombergerpowers/

    2 hr

  5. May 26

    I Invested in 70+ Startups. What Nobody Tells You About VCs | Andrew Ackerman

    In this episode, Leo Climaco sits down with venture capitalist Andrew Ackerman for an honest conversation about startups, investing, founder psychology, and what really happens inside the world of venture capital. Andrew has invested in more than 70 startups over the last 20+ years, reviewed over 10,000 pitches, and witnessed companies like SeatGeek go from near collapse to becoming one of the largest ticket marketplaces in the United States. They discuss:• Why VCs are perceived as “assholes”• The psychology behind investor decision-making• What “come back with more traction” actually means• How startups can validate ideas with almost no money• Why every startup is only as strong as its weakest link• Coachability and the mindset investors look for• The reality of power law investing• Why market downturns create opportunity• New York vs. Miami and the current startup ecosystem• Politics, culture, and navigating modern entrepreneurship This episode is about venture capital, resilience, founder mindset, and understanding how the startup world really works. Follow Leo Climaco: Instagramhttps://www.instagram.com/leoclimacopodcast/ TikTokhttps://www.tiktok.com/@leoclimacopodcast YouTubehttps://www.youtube.com/@leoclimacopodcast Official Websitehttp://leoclimacopodcast.com Andrew Ackerman:https://www.instagram.com/andrewbackerman/

    1h 33m

  6. May 22

    EN: $500 Start, 5,000 Doctors, MAHA Movement | Sam Tejada

    Sam Tejada joins Leo Climaco for a conversation about health, prevention, entrepreneurship, and the reality behind the modern medical system. After 12 years working as a firefighter paramedic, Sam realized most emergency calls were tied to chronic illness, poor lifestyle habits, and a healthcare system focused more on treatment than prevention. He later founded Liquivita with only $500 and built one of the leading IV therapy companies in the country. They discuss:• The reality behind the healthcare system• IV therapy, peptides, TRT, and longevity• Plastics, hormones, and declining health• Nutrition, food quality, and chronic disease• Building Liquivita from the ground up• The future of wellness and prevention This episode is about awareness, prevention, and understanding how health, discipline, and lifestyle choices shape long-term quality of life. Follow Out of the System: Instagram@leoclimacopodcast TikTok@leoclimacopodcast YouTube@leoclimacopodcast Leo Climaco@leoclimaco Sam Tejada@sammy_tejada

    1h 12m

  7. May 19

    Diving 20m at 75km/h: "Water Feels Like Concrete" | Ginni van Katwijk

    Ginni Van Katwijk joins Leo Climaco for a conversation about fear, discipline, identity, and living on the edge — literally. One of only a few permanent female athletes in the Red Bull Cliff Diving World Series, Ginni shares what it takes mentally and physically to jump from 20 meters into water at extreme speed. They discuss:• From gymnastics to professional cliff diving• Fear, pressure, and trusting your body• Why missing the Olympics changed her life• Internal discipline vs. external expectations• Aging, identity, and purpose in extreme sports• Learning to enjoy the process, not just the outcome This episode is about courage, mindset, and learning how to live fully even when fear is part of the journey. Follow Out of the System: Instagram@leoclimacopodcast TikTok@leoclimacopodcast YouTube@leoclimacopodcast Leo Climaco@leoclimaco Ginni Van Katwijk@adventures_with_ginni

    1h 12m

  8. May 15

    Walking America with $400 + NHL Zamboni Driver | Jack Kadis & Joseph Bennet

    Jack Kadis and Joseph Bennett join Leo Climaco for a conversation about risk, creativity, purpose, and building a life outside the system. Jack is walking the full perimeter of the United States on foot — starting with only $400 and no real plan.Joseph works as a lead ice technician for the Florida Panthers while chasing his dream of becoming a filmmaker. They discuss:• Walking across America one day at a time• Fear, kindness, and human connection on the road• AI, content creation, and the future of work• Entrepreneurship, personal branding, and Gen Z ambition• Creativity, filmmaking, and unconventional careers• The difference between hype and real execution This episode is about freedom, adaptability, and creating your own path — even when nobody understands the vision. Follow Out of the System: Instagram@leoclimacopodcast TikTok@leoclimacopodcast YouTube@leoclimacopodcast Leo Climaco@leoclimaco Jack Kadis@jlkadis Joseph Bennett@joeyjb06

    1h 21m
See All (174)

Ratings & Reviews

5
out of 5
2 Ratings

About

Out of the System – Stories from Those Who Broke the Rules and Won Empowering entrepreneurs who choose to walk a path outside the norm. In this segment, we dive into real strategies, insights, and success stories that challenge the traditional system and push your business to the next level. From innovative marketing tactics to authentic leadership principles, we provide practical advice for those ready to grow with independence and intention. 🎧 Tune in weekly to gain the knowledge and inspiration you need to accelerate your journey to success on your own terms.

Information

  • Creator
    Leo Climaco
  • Years Active
    2024 - 2026
  • Episodes
    174
  • Rating
    Explicit
  • Copyright
    © Leo Climaco
  • Show Website
    Out Of The System

You Might Also Like