About Me

Building A Legacy With Heart And Hard Work

Welcome to the world of Michael Upshire, a testament to the power of resilience, ambition, and transformative thinking. Born into humble beginnings in the bustling city of Chicago, my life’s journey is a story of metamorphosis—from a life of limited means to becoming a beacon of success in the entrepreneurial world. Alongside my wife, the co-pilot of my dreams, we’ve built a family-oriented business empire. Our foundation rests on pillars of trust, dedication, and relentless hard work. It’s not just about doing business; it’s about nurturing relationships and fostering growth in every interaction.

Empowering Transformation Through Entrepreneurship

My vision is to create a world where ambition and action converge to transform dreams into reality. I see a future where individuals from all walks of life are equipped with the knowledge, resources, and confidence to venture into the realms of financial coaching, car-sharing, real estate, and freight brokering. It’s about fostering a global community that thrives on mutual growth, innovation, and sustainable success. I envision a society where success is not just a privilege for the few but an attainable goal for many, driven by the power of informed entrepreneurship.

Guiding Aspiring Entrepreneurs to Tangible Success

My mission revolves around the core purpose of guiding and mentoring aspiring entrepreneurs to achieve tangible success in their endeavors. Through personalized coaching, strategic advice, and the sharing of my own experiences and lessons learned, I aim to demystify the path to business success. I am dedicated to providing the tools and insights necessary for navigating the complex landscapes of various industries. My focus remains steadfast on nurturing talent, unlocking potential, and helping individuals and businesses thrive in a competitive world.

Creating a Legacy of Shared Success and Growth

The cornerstone of my goal is to create a legacy that transcends individual achievements – a legacy marked by shared success and collective growth. It’s about more than just reaching financial milestones; it’s about building a community of empowered, knowledgeable, and successful entrepreneurs. My aim is to raise the bar of what’s achievable, inspire continuous learning, and encourage a culture of sharing and collaboration. Ultimately, my goal is to witness a world where each entrepreneur I mentor becomes a beacon of success and an inspiration to others, thus perpetuating a cycle of growth and success.

Empower your ambition 

Unlocking Potential, Nurturing Growth, and Paving Pathways to Success

Step into a world where your aspirations meet our expertise. From uncovering hidden investment gems to cultivating robust business strategies, and nurturing personal growth, our services are designed to elevate every aspect of your professional journey. Each offering is a cornerstone in building a future defined by success, innovation, and personal fulfillment.

Investment Opportunities

Gain access to top investment opportunities, enhancing your portfolio with strategic, profitable choices.

Networking And Community Building

Build a powerful network and community, fostering lasting relationships and collaborative growth opportunities.

Personal Development

Enhance your personal growth, unlocking potential for greater professional success and fulfillment.


Empower your business with expert consulting, driving innovation, efficiency, and sustained growth.

My Services

Transformative Services: Elevating Your Business and Investment Journey

Discover a suite of specialized services designed to revolutionize your entrepreneurial and investment endeavors. From the intricacies of freight brokering and car-sharing enterprises to the sophisticated realms of investment and business consulting, Michael Upshire offers expert guidance to navigate these dynamic industries. Each service is tailored to empower your success, whether you’re building a business from the ground up or elevating your investment portfolio. Embark on a transformative journey with us and unlock your full potential in today’s competitive landscape.


Step into the vibrant realm of freight brokering with Michael’s seasoned expertise. Turn your interest in logistics into a thriving enterprise. With his mentorship, delve into the core aspects of the freight industry, from establishing strong network ties to navigating complex regulations, and managing a diverse fleet efficiently. Begin your venture in freight brokering and steer your way to success now.

Rental Cars

Dive into the thriving world of car-sharing with Michael’s expert guidance. Transform your passion for reliable transportation into a flourishing business. Under his mentorship, you’ll master the essentials of the car-sharing market, from fine-tuning your listings to effective fleet management, and building a dedicated customer following. Start your journey in the car-sharing business and drive towards success today.


Venture into the lucrative world of investments with Michael’s strategic insights. Transform your financial goals into substantial wealth. Under his guidance, uncover the secrets of successful investing, from navigating the complexities of the stock and real estate markets to identifying high-potential opportunities. Embark on your investment journey with Michael and chart a course towards financial triumph and stability today.


Immerse yourself in the realm of business consulting with Michael’s unparalleled expertise. Elevate your entrepreneurial vision into a reality. Through his mentorship, grasp the nuances of effective business strategies, from optimizing operations to scaling for growth and market leadership. Initiate your consulting journey with Michael and navigate the path to business excellence and innovation today.

My podcast

Risk Takers Podcast: Unleashing the Power of Bold Entrepreneurship

Tune into the ‘Risk Takers Podcast’ where audacious dreams meet actionable insights. Hosted by Michael Upshire, this podcast is a treasure trove of inspiration and practical advice for aspiring entrepreneurs and seasoned business professionals alike. Each episode delves into the heart of business acumen, from navigating the complexities of various industries to balancing professional success with personal growth. 

risk takers only 

Take Action

Ready to elevate your entrepreneurial journey? Step into a world of opportunity with Michael Upshire. Here, ambition meets expertise, and your dreams of success get a roadmap. Whether you’re seeking guidance in the freight industry, looking to dive into car-sharing, or wanting to navigate the complex world of investments, Michael is here to guide you. Transform your vision into reality with tailored strategies and actionable insights.


Client Success Stories

Hear directly from those who’ve journeyed with Michael Upshire and experienced transformative success. Each testimonial is a story of ambition realized, a testament to the power of dedicated mentorship and strategic guidance. From fledgling entrepreneurs to seasoned business owners, these success stories illustrate the impactful change Michael brings to every venture. Be inspired by real-life examples of how your aspirations can turn into tangible achievements.

” I can’t recommend Michael’s coaching services enough. He helped me turn my financial life around and launch my own successful financial coaching business. His guidance, support, and expertise have been invaluable, and I now feel in control of my finances with a bright future ahead. “

Sarah J.

Financial Coaching Client

” I struggled for years in the real estate industry before discovering Michael’s coaching services. He taught me everything I needed to know about real estate wholesaling, property flipping, and investing. With his help, I started closing deals and earning profits in no time. I am extremely grateful for his expertise and guidance, and I highly recommend him to anyone looking to succeed in the real estate industry. “

John D.

Investment Client

” Starting a car-sharing business seemed impossible until I began working with Michael. He helped me optimize my listings, attract more customers, and grow my business. Thanks to his guidance, I now have a steady income from car-sharing and am excited about my business’s future. “

Tom L.

Car Sharing Client

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