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

She Was Humiliated at Work — Then Built an Empire | Jen Conkey

Jen Conkey once had just 35 cents in her bank account. Today, she manages more than $160 million in assets across multiple industries. In this episode of Out of the System, Leo Climaco and Jen Conkey discuss investing, financial freedom, entrepreneurship, wealth building, and creating income-producing assets. They discuss: • Growing up between two very different financial realities and the lessons that shaped her mindset • Leaving a 22-year corporate career to pursue financial independence • The moment she quit her job after being publicly humiliated in front of her team • Why job security is often an illusion • Her philosophy of living on 70%, investing 20%, and saving 10% • The strategy of buying assets first and allowing them to fund your lifestyle • Building a portfolio of more than 2,500 real estate units • The four asset classes she invests in: real estate, oil and gas, self-storage, and dividend-paying investments • Why adaptability will be one of the most valuable skills in the age of AI • Creating long-term wealth through discipline, strategy, and consistent action This episode explores investing, financial literacy, entrepreneurship, and the mindset required to build lasting wealth and financial freedom. Follow Out of the System: Instagram ⁠@leoclimacopodcast⁠ TikTok ⁠@leoclimacopodcast⁠ YouTube ⁠@leoclimacopodcast⁠ Official Website ⁠Out of the System⁠ Jen Conkey: Instagram ⁠@jenconkey⁠

How a Brazilian Woman Broke Into Hollywood Without Asking for Permission | Carolina Brasil

She left the ballet stage, built a fashion brand, became a film producer — and now has two films headed to Cannes. In this episode of Out of the System, Leo Climaco sits down with Carolina Brazil — ballerina trained by the Royal Academy of Dance in London, former fashion designer, entrepreneur, and Brazilian film producer with more than 12 projects to her name. Born and raised in Ipanema, Rio de Janeiro, she built multiple careers by following one simple principle: never wait for permission, and always leave a seed of love wherever you go. They discuss: • How she built a ballet studio with 180 students at just 19 years old • Her transition from fashion to independent filmmaking and what it meant to leave ego behind • The two films she is taking to Cannes and a feature film about a director on the autism spectrum • Why she brought ballet to Rocinha when everyone said it was impossible • Her relationship with God, faith, forgiveness, and the importance of letting go • The philosophy behind being “Unstoppable” and why your first attempt doesn’t have to be your best • Reinvention, creativity, and building across multiple industries with purpose A powerful conversation about reinvention, faith, creativity, love, and building a life led by purpose. Follow Out of the System: Instagram: https://www.instagram.com/leoclimacopodcast/ [https://www.instagram.com/leoclimacopodcast/] TikTok: https://www.tiktok.com/@leoclimacopodcast [https://www.tiktok.com/@leoclimacopodcast] YouTube: https://www.youtube.com/@leoclimacopodcast [https://www.youtube.com/@leoclimacopodcast] Official Website: http://leoclimacopodcast.com [http://leoclimacopodcast.com/] Connect with Carolina: https://www.instagram.com/carolinabrasilofficial/ [https://www.instagram.com/carolinabrasilofficial/]

He Almost Became a Millionaire — Then Lost Everything in Crypto. | Karl Smith

He was just cents away from reaching $1 million. Then the market turned — and he watched it all disappear right in front of him. In this episode of Out of the System, Leo Climaco sits down with Karl Smith, better known as K Smith Inspires — entrepreneur, mentor, speaker, and creator of the Reinvention Blueprint. The son of Haitian immigrants, raised in Miami, Karl went from spending two years broke in direct sales (while everyone laughed at him) to earning six figures by age 21 — only to learn the hard way the difference between making money and keeping money. They discuss: • How he spent two years making nothing before his first major breakthrough • Losing nearly $1 million in crypto — and why he realized he needed equity • His time on a reality show that made him “the most hated man in America” • The “50-meter headlights” mindset: how to keep moving forward even when you can’t see the full path • Why selling is simply influence — and influence is leadership • The Warren Buffett story and the power of compound interest • His study of billionaires and the one trait they all share A powerful conversation about failure, reinvention, sales, money, and building from the ground up. Follow Out of the System: Instagram: @leoclimacopodcast TikTok: @leoclimacopodcast YouTube: @leoclimacopodcast Official Website: Out of the System Karl Smith: @ksmithinspires #OutOfTheSystem #KSmithInspires #Entrepreneurship #Sales #Mindset #Reinvention #LeoClimaco

She Turned Trauma Into a Luxury Empire in Miami | Gloria Garcia

Gloria Garcia, known as Glowstar, became a mother at 17 after surviving a childhood marked by abuse, abandonment, and adversity. In this episode of Out of the System, Leo Climaco and Gloria Garcia discuss resilience, healing, entrepreneurship, personal transformation, and breaking generational cycles. They discuss: • Growing up between Colombia, the Bronx, and some of Miami’s toughest neighborhoods • The abuse she experienced within her own family and the challenges of being unheard • How becoming a mother at 17 changed the direction of her life • Building a luxury hospitality business centered on relationships and exceptional experiences • The mindset that helped her overcome adversity and keep moving forward • Her healing journey through therapy, biohacking, and holistic wellness practices • Recovering from a heart attack and a serious car accident • The inspiration behind her upcoming book, Pain Into Power • Transforming trauma into strength and purpose This episode explores resilience, healing, entrepreneurship, and the power of rewriting your story despite the circumstances you were born into. Follow Out of the System: Instagram ⁠@leoclimacopodcast⁠ TikTok ⁠@leoclimacopodcast⁠ YouTube ⁠@leoclimacopodcast⁠ Official Website ⁠Out of the System⁠ Gloria Garcia (Glowstar): Instagram ⁠@glostar⁠

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 Website ⁠Out of the System⁠ Dan “Big D” Sikowski: ⁠@_big_dan_official⁠