Best Of DealQuest: The Power of Freedom in Business & Life

In this Best Of episode, I’m revisiting the highlights of our past episodes where freedom was a central theme in business and life. Over the years, our incredible guests have shared their unique perspectives on how true freedom—whether financial, geographical, or emotional—can transform both personal and professional growth. As an entrepreneur, achieving freedom isn’t just about stepping away from the 9-to-5 grind; it’s about designing a life that’s authentically yours and aligned with your values.

We'll delve into the diverse perspectives of entrepreneurs on what freedom means to 33 of past DealQuest guests: David Wood, Natasha Miller, John Warrilow, Phil Fiore, Bob Oros, Thomas Samuelson, Claire O'Keefe, Gabriel Galvez , Channing Hamlet, Nick Cavuoto, Scott Hallman… Whether you’re a seasoned entrepreneur or just starting out, this episode is packed with inspiration to help you embrace freedom in all aspects of your life.

EPISODE 163 WITH DAVID WOOD

The idea of emotional freedom, which David Wood defines as the ability to truly understand yourself, both the parts you love and the parts you're not so proud of. David explains that while financial freedom, geographical freedom (the ability to work from anywhere), and time freedom (being able to choose when and how you work) are all incredibly important, emotional freedom is the most powerful one.

He emphasizes that emotional freedom starts with self-awareness—the ability to recognize and acknowledge what's really going on inside you. Once you have this awareness, you can take steps to share it with others in a way that builds connection. This leads to a more fulfilled life, with deeper connections and a greater sense of freedom in every aspect—personal, professional, and emotional.

EPISODE 175 WITH NATASHA MILLER

Freedom is not just about luxury or living a life of leisure; it’s about having the autonomy to pursue your passions and creativity without being weighed down by financial stress or external dependencies. Natasha Miller highlights that true freedom comes from being able to do what you love, when you want to do it, without the constant worry of money or security. Success, in her view, is the ability to live authentically and creatively, which provides a deeper sense of fulfillment than material wealth or lavish lifestyles.

EPISODE 197 WITH JOHN WARRILLOW

True freedom is about having the flexibility to prioritize what matters most to you, like spending time with family, without being restricted by obligations to others. John Warrillow highlights that as a "freedom fighter" entrepreneur, his greatest motivation is the ability to choose how he spends his time, especially when it allows him to experience moments that bring personal fulfillment.

EPISODE 203 WITH PHIL FIORE

True freedom comes from unleashing your creativity and allowing yourself to think freely. Phil Fiore explains how, as an entrepreneur, he was able to break free from the intellectual confines of his previous role and embrace a more liberated, creative mindset.

EPISODE 209 WITH BOB OROS

True freedom is a privilege that should never be taken for granted. Bob Oros emphasizes the importance of appreciating the ability to make choices each day, especially in business. The freedom to chart your own course and make decisions is a powerful gift that can shape the direction of your life and work.

EPISODE 219 WITH THOMAS SAMUELSON

Freedom in business is about owning your success and working on your own terms. Thomas Samuelson explains how his career, where compensation was directly tied to performance, taught him the value of self-reliance and peace of mind. True freedom allows you to control your destiny, without being dependent on others for your pay or success.

EPISODE 221 WITH CLAIRE O'KEEFE

True freedom is having the ability to give back, pursue your passions, and explore the world. Claire O'Keefe emphasizes how financial success has empowered her to make a difference, travel, and stay true to her roots. Achieving freedom is not just for personal gain, but for contributing to others and embracing life's opportunities.

EPISODE 226 WITH GABRIEL GALVEZ

True freedom is the autonomy to grow, explore, and create your own path. Gabriel Galvez emphasizes that freedom isn't just about having choices—it's about using those choices to evolve, learn, and make a meaningful impact.

EPISODE 236 WITH CHANNING HAMLET

True freedom as an entrepreneur comes from owning your decisions and learning to prioritize. Channing Hamlet reflects on the importance of taking responsibility for both your successes and mistakes. The key to sustaining freedom is making intentional choices about what to commit to and what to delegate, empowering you to control your time and energy.

EPISODE 240 WITH NICK CAVUOTO

True freedom comes through redemption after setbacks. Nick Cavuoto highlights that moments of crisis, like losing a million dollars, can lead to transformative growth. The key is not staying stuck in the aftermath, but embracing the opportunity for redemption. This process of overcoming challenges and learning to trust, rebuild, and move forward is essential for personal and business success.

EPISODE 248 WITH SCOTT HALLMAN

True freedom comes from the ability to learn, apply knowledge, and use it to improve your life and the lives of others. Scott Hallman emphasizes that freedom is not just about choice, but about using the freedom we have to continuously grow, create balance, and make intentional decisions that allow us to live life fully. If you're feeling trapped in your work, remember, there are choices you can make to create more freedom in your life.

EPISODE 253 WITH ANTONY NITKOS

True success and freedom are measured by happiness, both in what you do and how you make others feel. Antony Nitkos teaches that the real measure of success is not money, but whether you're content with your actions and relationships. In the end, it’s not about material wealth, but the memories and positive impact you leave behind. Freedom means living authentically, with happiness as the ultimate goal.

EPISODE 256 WITH JESSICA POLITO

True freedom in business comes from knowing when to delegate and relinquish control. Jessica Polito shares that while entrepreneurship may initially offer the freedom to manage every aspect of a business, true liberation arises when you partner with others or bring in support to handle tasks you don't enjoy, allowing you to focus on what you love. This creates more time for personal priorities, such as family, without sacrificing professional success. Balancing work with personal life can be achieved by making strategic choices to free yourself from unnecessary burdens.

EPISODE 257 WITH JAY GOLDMAN

The value of freedom becomes truly apparent when compared to a lack of it. Jay Goldman’s story highlights how his parents made the life-changing decision to emigrate from apartheid-era South Africa to Canada, seeking a better life where freedom and equal opportunity were accessible to all. The lesson is that freedom is not just a given, but a privilege that should be cherished. When we take freedom for granted, we miss the deep significance it holds in shaping our opportunities, choices, and quality of life.

EPISODE 260 WITH MATTHEW KHALILI

True freedom is about controlling your time and choices. Matthew Khalili emphasizes the importance of achieving a lifestyle where you can make money without direct labor and prioritize spending time with family and pursuing your passions. While reaching this level of freedom requires effort and perseverance, it serves as an aspirational goal for entrepreneurs, showing that freedom comes from creating systems that allow you to focus on what truly matters.

EPISODE 264 WITH SALVATORE BUSCEMI

True freedom comes from the ability to make a meaningful impact. Salvatore Buscemi highlights that while financial success is a part of freedom, the real fulfillment lies in using that freedom to contribute to causes that positively affect millions of lives. He emphasizes the power of making impactful investments, especially in industries like life sciences, where the potential to change lives is significant.

EPISODE 265 WITH KEVIN STANSFIELD

Freedom is about having the power to choose how you live and work, but it also involves balance. Kevin Stansfield shares that true freedom comes from the ability to choose what you want to do, when, and with whom. However, he also emphasizes that too much freedom can lead to a lack of structure, and having a sense of responsibility or purpose is essential. Freedom and hard work can coexist when you have the choice to manage both effectively, creating a fulfilling and balanced lifestyle.

EPISODE 268 WITH BRETT MARTIN

True freedom is the ability to be fully self-expressed without fear of judgment or self-censorship. Brett Martin emphasizes that the highest form of freedom is not just about external circumstances or autonomy, but about being authentic and free to express yourself openly. He highlights that we often hold ourselves back due to societal pressures or personal fears, and overcoming these limitations is key to experiencing true freedom.

EPISODE 269 WITH DAVID BACH

True wealth is not just about money, but about designing a life that aligns with your values and dreams. David Bach stresses the importance of prioritizing family, experiences, and personal fulfillment over financial gain alone. By preparing for years to take a year off and live in Florence, he exemplifies how financial freedom enables you to live authentically and pursue what truly matters.

EPISODE 271 WITH BRIAN MEAGAN

True freedom comes from the ability to design your own path and make decisions on your terms. Brian Meagan highlights how his journey as an entrepreneurial lawyer has allowed him to break free from conventional expectations, both in terms of work structure and client relationships. By embracing autonomy and using his legal expertise to empower others, he underscores the importance of becoming a "freedom facilitator" — helping others achieve their own freedom while building a life aligned with their values.

EPISODE 272 WITH HARRIS BOLCH

Freedom is not just about independence but also about creating harmony and unity in all areas of life. Harris Bolch emphasizes that true freedom enables us to operate at our highest level by fostering peace and balance both at home and in the workplace. When we create a harmonious environment around us, it empowers us to thrive and reach our full potential.

EPISODE 273 WITH RYAN TANSOM

True freedom is multidimensional, encompassing time, money, relationships, and purpose. Ryan Tansom highlights Dan Sullivan’s Four Freedoms, emphasizing that freedom is not just about managing time but also about choosing the right people to interact with, engaging in meaningful work, and pursuing personal goals. To make a real impact, it's essential to first secure these foundational freedoms, which allow you to focus on what matters most and reach your full potential.

EPISODE 274 WITH ELLIOT CALLAN

Freedom is about living life to the fullest in the present, not postponing joy and fulfillment for later. Elliot Callan shares how he and his wife decided not to wait for retirement to experience the things they love—like traveling, enjoying great food and wine, and staying physically active. By designing their lifestyle now, they are able to prioritize their passions and create lasting memories, demonstrating that true freedom lies in embracing what brings you joy and fulfillment in the moment.

EPISODE 276 WITH MAT PUTRA

True freedom is the ability to choose how you spend your time, money, and energy. Mat Putra highlights that entrepreneurship has given him the power to make decisions based on his values and priorities, such as spending time with family or taking spontaneous vacations. The ability to say "no" to things that don't align with your goals or happiness is a key component of freedom, enabling you to live life on your own terms.

EPISODE 277 WITH GINA COCKING

Freedom comes with responsibility and pressure. Gina Cocking emphasizes that while having the autonomy to make choices and shape the direction of her business is empowering, it also brings challenges. The freedom to lead and succeed requires hard work, accountability, and the constant awareness of potential risks and consequences. True freedom involves embracing both the opportunities and the pressures that come with it.

EPISODE 278 WITH NOAH GRAFF

True freedom is a mindset. Noah Graff highlights that freedom isn’t just about money or time, but how you perceive and handle your situation. Regardless of external circumstances, if your mind is clouded by worry or limited thinking, you won’t feel free. To achieve true freedom, it's essential to cultivate a mindset that embraces abundance, choice, and the ability to let go of limiting beliefs—because even with resources, freedom is only realized when you believe you have the power to choose how to live your life.

EPISODE 280 WITH JON PROTHRO

True freedom is about the ability to work with people you enjoy and having the time to spend with your loved ones. Jon Prothro emphasizes that freedom isn't just a concept but a lifestyle that allows you to prioritize relationships and work in environments that align with your values. It’s not just about financial independence, but creating the space to nurture personal connections and do meaningful work with people you trust and respect.

EPISODE 281 WITH JOGN AUSTENSEN

True freedom comes from the ability to make life-changing decisions that align with your personal values. John’s decision to leave the corporate world for greater independence has been a source of fulfillment, and he encourages others to pursue the same freedom, regardless of external pressures.

EPISODE 282 REMASTERED EPISODE 69 WITH MIKE MICHALOWICZ

Freedom is the ability to express and serve others authentically, without being constrained by rigid protocols. Mike highlights that true freedom allows individuals to discover their unique way of making an impact, which is the ultimate form of personal expression and service.

EPISODE 284 WITH STEPHEN SPEAR

Freedom encompasses both personal autonomy and the protection of fundamental rights, such as the ability to work and provide for one’s family without excessive interference. Stephen emphasizes the importance of preserving constitutional freedoms, particularly the First Amendment, as essential to maintaining a free society.

EPISODE 285 WITH SCOTT BUSHKE

True freedom is not just about having time or money, but about finding balance between the two. Scott emphasizes that freedom allows you to help others, have personal fulfillment, and live life to its fullest, such as being able to spend quality time with family and pursue passions like coaching basketball.

EPISODE 286 WITH RICHARD PARKER

Freedom is the ability to make choices that not only benefit yourself but also positively impact those around you. Richard highlights that true freedom enables you to elevate others, just like Sidney Crosby elevates his teammates, and to make meaningful contributions in all aspects of life, including personal relationships and business.

EPISODE 289 WITH DARREN HOROWITZ

Freedom involves self-forgiveness, growth, and being true to who you are. Darren believes that true freedom comes from learning from past mistakes, embracing your authentic self, and sharing your journey to help others, driven by passion rather than money.

EPISODE 290 REMASTERED EPISODE 102 WITH DAVID CALLOW

The freedom of entrepreneurship lies not just in owning your time and decisions but in empowering others to create solutions that enrich lives. By providing tools and resources, entrepreneurs can build businesses that create jobs and positively impact communities.

EPISODE 292 REMASTERED EPISODE 75 WITH JESSE COLE

True success is the combination of freedom, fulfillment, and making an impact. When you create something larger than yourself that challenges the status quo, it not only fuels your passion but also leads to greater freedom and the opportunity to share success with others.

EPISODE 293 WITH SONNY VAN DE BEEK

Freedom is about choice—having the ability to live to your full potential and sometimes overcoming your own limitations. As a leader, your actions and energy influence others significantly, so be mindful of how you build your company and the impact it has on your team, families, and communities.

This episode is a must-listen for anyone looking to redefine their relationship with work, freedom, and success.

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Listen to the Full DealQuest Podcast Episode Here: https://podcasts.apple.com/us/podcast/dealquest-podcast-with-corey-kupfer/id1451959848

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Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

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