Choppin' It Up

SUMMARY:

In this episode, host Will Jenkins sits down with Megan Masud and Sarah Hanna, Co-Founders of Competum Collective LLC, to share their entrepreneurial story and mission to improve the lives of drivers in the logistics industry.

They break down how Competum Collective is tackling critical gaps with mental health support, compliance education, affordable healthcare options, and substance abuse resources. From navigating the healthcare side of trucking to creating safe, judgment-free spaces for carriers, Megan and Sarah discuss the lessons they’ve learned, the resilience required to build a business, and their vision for expanding nationwide.

This conversation is packed with insights for anyone in logistics, trucking, compliance, or entrepreneurship.

TAKEAWAYS:

• Megan Masud and Sarah Hanna met unexpectedly and founded Competum Collective LLC to transform driver support.
• Mental health programs for drivers are at the center of their mission.
• Compliance education helps carriers avoid preventable issues.
• Their services include affordable healthcare and substance abuse resources.
• Strong industry relationships have fueled their growth.
• Competum Collective creates safe spaces for drivers to seek help without judgment.
• They pivoted their model based on market research and feedback.
• Entrepreneurship requires grit, adaptability, and persistence.
• Their expansion plan will bring essential services to drivers nationwide.

CHAPTERS:

00:00 – Introduction and Backgrounds
10:16 – Career Insights and Lessons Learned
13:48 – The Birth of Competum Collective
18:21 – Services Offered by Competum Collective
19:54 – Navigating Compliance for Independent Contractors
21:38 – The Impact of Substance Abuse Programs
23:09 – Proactive Measures for Driver Safety
26:43 – Building Relationships in the Industry
29:57 – Leveraging Subscription Services for Drivers
32:41 – Overcoming Challenges in Business Development
37:14 – Personal Growth Through Reading and Reflection

EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

Be sure to follow and tag @JourneyDelivers on LinkedIn and Instagram! 

SUMMARY:

In this episode of Choppin’ It Up, Will Jenkins sits down with CJ Johnson, founder of BWS Logistics, a 3PL known for handling the tough stuff, like fragile freight, complex consolidation, last-minute loads, with ease.

CJ shares how growing up in Chicago and handing out pizza flyers laid the groundwork for his entrepreneurial grit. From switching majors in college to honing his sales game at Sears, every step helped prepare him to launch BWS after a failed partnership deal.

They dig into how BWS built its reputation on trust, relationships, and proactive communication—and why CJ still believes human connection will always outperform automation in freight.

TAKEAWAYS: 

• The best training ground is real-world sales 
• Relationships still win in logistics 
• BWS makes the complex simple for shippers 
• You only need one door to open to build something big 

CHAPTERS: 

• 00:00 – Intro 
• 02:06 – Growing Up in Chicago 
• 04:00 – Pizza Flyers and Early Hustle 
• 06:49 – College Pivot: Biology to Tech 
• 11:15 – Sales at Sears: Real-World Education 
• 13:42 – Getting into Freight 
• 18:05 – When a Deal Fails, a Business Begins 
• 20:37 – Building BWS Logistics from the Ground Up 
• 23:56 – What Makes BWS Stand Out in 3PL 
• 28:02 – Lessons in Leadership and Entrepreneurship 
• 35:46 – Freight Market Insights and Advice

EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

Be sure to follow and tag @JourneyDelivers on LinkedIn and Instagram! 

SUMMARY:

In this episode of Choppin' It Up, Will Jenkins interviews Elizabeth Moscoso, President of Moscoso Express, a trucking company specializing in air freight. Elizabeth shares her journey from childhood involvement in the family business to leading the second generation of the company. The conversation explores the evolution of the trucking industry, the importance of technology, and the challenges of leadership. Elizabeth emphasizes the significance of team retention, problem-solving, and building personal relationships in the business. She also offers valuable insights on maintaining quality customer service and the importance of believing in oneself.

TAKEAWAYS:

• Moscoso Express started with humble beginnings and has evolved over 20 years. 
• Technology has significantly changed the logistics and air freight industry. 
• Building personal relationships is crucial in the trucking business. 
• Team retention is key to maintaining quality service. 
• Problem-solving is emphasized over strict adherence to SOPs. 
• Transparency within the team fosters a positive work culture. 
• Understanding cash flow is essential for business success. 
• Delegation is important for entrepreneurial growth. 
• The air freight niche requires attention to detail and adaptability. 
• Believing in oneself is fundamental to achieving entrepreneurial dreams.

CHAPTERS: 

• 00:00 Introduction to the Journey 
• 02:31 Overview of Moscoso Express 
• 03:03 The Roots of Moscoso Express
• 06:20 Evolution of the Business 
• 09:10 Air Freight and Technology 
• 11:57 Staying Nimble in Business 
• 14:33 Team Retention Strategies 
• 17:53 Corporate Experience and Its Impact 
• 21:12 Challenges in Leadership 
• 24:01 Building Relationships in the Industry 
• 27:25 Quality Support and Customer Service 
• 28:28 Advice for the Younger Self

EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

Be sure to follow and tag @JourneyDelivers on LinkedIn and Instagram! 

SUMMARY:

In this episode of Choppin' It Up, host Will Jenkins sits down with Kevin McMaster, SVP of Sales and Operations at Flock Freight. Kevin shares his story of immigrating to the U.S. and building a standout career in freight, from his early days at Coyote to leading teams at Flock. He opens up about the challenges he faced, the mentors who shaped him, and the mindset that helped him grow into a top performer. Will and Kevin dig into the competitive nature of sales in logistics, the shift from individual contributor to leader, and what it takes to build and scale a freight organization. They also talk about the power of relationships, leadership lessons learned the hard way, and the books that helped shape their perspectives.

TAKEAWAYS:

• Kevin immigrated to the U.S. at 13, an experience that helped build his resilience and independence. 
• He started his career in transportation in 2007 and quickly learned the value of hard work. 
• The competitive, high-performance culture at Coyote played a major role in shaping his career. 
• Mentorship was a key factor in Kevin’s growth—from carrier sales to leadership roles. 
• His time in Europe gave him an early sense of independence and problem-solving. 
• Struggles in school taught him grit and how to push through challenges. 
• Prioritizing customer service became a cornerstone of his sales approach. 
• Kevin’s competitive mindset was clear: “I wanted to emulate number one—and beat number one.” 
• He believes you need to do the job you want before you get the job you want. 
• Building strong, authentic relationships is essential in leadership. 
• Success comes from organizing and executing around what the business truly needs. 
• Some challenges—like the infamous "$10 books"—still persist in the freight world. 
• "If you go and book the volume, the money will come." 
• He was scared to leave Real Time Freight for Coyote, but believed in himself and took the leap. 
• Mistakes are part of the process: “It’s okay to not get it right.” 
• Flock’s success isn’t about one person—it’s about the team and the mission. 
• Belief in himself was a driving force throughout his career.

CHAPTERS: 

00:00 Introduction to Kevin McMaster 

02:53 Kevin's Early Life and Immigration Story 

11:26 Educational Journey and Career Beginnings 

14:09 Joining Coyote: The Early Days 

18:59 Roles and Responsibilities at Coyote 

25:25 Transitioning to Leadership and Career Growth

25:53 The Competitive Spirit: Emulating Success 

26:43 Leadership Lessons from Coyote 

32:57 Transitioning to Flock Freight 

41:14 Building a New Organization: The Flock Experience 

51:27 Key Takeaways and Influential Books Start your Journey at www.journeydelivers.com

EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

Be sure to follow and tag @JourneyDelivers on LinkedIn and Instagram! 

SUMMARY:

In this episode of Choppin' It Up, Rob Skelton, CEO of Third Coast Logistics, shares his journey from the military to the freight industry. He discusses the challenges he faced while starting his business, the importance of leadership and team building, and how he navigated financial management during tough market cycles. Rob emphasizes the significance of building strong relationships in the freight industry and offers valuable advice for new brokerages. He also shares insights on personal development and the impact of mentorship on success. 

TAKEAWAYS: 

• Rob's journey began with a passion for the freight business. 
• Starting Third Coast Logistics was a pivotal moment in his career. 
• Financial discipline is crucial for long-term success. 
• Building a strong company culture is essential for employee retention. 
• Mentorship can significantly impact business growth. 
• Understanding the unique nature of freight is key to success. 
• Hiring the right people is critical for a small business. 
• Rob emphasizes the importance of personal goals in employees. 
• Navigating market cycles requires strategic financial management. 
• Continuous learning and adaptation are vital in the logistics industry. 

CHAPTERS: 

• 00:00 Introduction to Rob Skelton and His Journey 
• 02:56 Early Career and Military Background 
• 06:02 Transition to Freight and Starting Third Coast Logistics 
• 09:11 Challenges and Lessons Learned in Business 
• 12:05 Leadership and Team Building in a Small Business 
• 14:54 Financial Management and Navigating Market Cycles 
• 17:52 The Unique Nature of Freight and Building Relationships 
• 20:58 Advice for New Brokerages and Personal Development 
• 23:57 Favorite Books and Closing Thoughts

EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

Be sure to follow and tag @JourneyDelivers on LinkedIn and Instagram! 

SUMMARY:

In this special Women's History Month edition of Choppin' It Up, the conversation revolves around the importance of mentorship, the challenges women face in a male-dominated industry, and the leadership lessons learned throughout their careers. Erin Sweeney, Maya Quijada and Nicki Bottan share personal stories with Will Jenkins of how mentorship has shaped their professional journeys, the significance of advocating for one another, and the trends they hope to see in the freight industry. They celebrate the achievements of women leaders and discuss the unique experiences of working in a fast-paced startup environment, emphasizing the value of community and support among women in the workplace.

TAKEAWAYS:

• Mentorship plays a crucial role in career development.
• Women supporting women is essential in male-dominated industries.
• Leadership requires vulnerability and the ability to ask for help.
• Authenticity is key to personal and professional growth.
• Advocacy is a powerful tool for empowering others.
• Creating a supportive community enhances workplace dynamics.
• Women in leadership positions can inspire future generations.
• Embracing failure is part of the growth process.
• Diversity in leadership leads to better business outcomes.
• The journey of entrepreneurship is about the people you impact.

CHAPTERS:

• 00:00 Introduction to Women's History Month Special
• 01:33 The Impact of Mentorship on Career Growth
• 06:13 Navigating a Male-Dominated Industry
• 10:12 Leadership Lessons Learned
• 15:26 Trends and Changes for Women in Freight
• 18:38 Celebrating Women Leaders in Freight
• 22:45 Working in a Fast-Paced Startup Environment
• 27:43 Unexpected Gratifying Moments in Careers
• 31:44 The Importance of Advocacy in Mentorship
• 36:12 Closing Thoughts and Community Building

EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

Be sure to follow and tag @JourneyDelivers on LinkedIn and Instagram! 

SUMMARY:

In this episode of Choppin' It Up, host Will Jenkins joins David Bell, CEO & Founder of CloneOps.ai, and Alfonso Quijano, CTO of Lean Solutions Group, to discuss their experiences in the logistics industry, focusing on the integration of AI and technology in business operations. They emphasize the importance of building relationships, understanding the logistics space, and the evolving nature of sales strategies. The conversation highlights the need for businesses to adapt to technological advancements while maintaining strong customer relationships and delivering value. Both guests share insights on their journeys, the challenges they faced, and their vision for the future of logistics and AI.

TAKEAWAYS:

• Experience is everything in business.
• Building relationships is key to success.
• AI will transform logistics operations.
• Customer acquisition costs can be reduced through partnerships.
• Understanding the logistics space is crucial for tech companies.
• Sales in logistics are becoming more sophisticated.
• Long-term strategies are essential for business sustainability.
• The speed of technology is accelerating rapidly.
• AI will help businesses scale and manage attrition.
• Fundamentals of business must not be overlooked in the AI era.

CHAPTERS:

• 00:00 Introduction to the Journey
• 01:05 Innovations in Logistics and AI
• 03:57 Building Relationships in Business
• 08:10 The Importance of Experience in Logistics
• 11:58 Customer Acquisition Strategies
• 15:51 The Evolution of Sales in Logistics
• 20:05 The Role of AI in Business
• 24:10 Long-Term Business Strategies
• 27:59 Final Thoughts and Recommendations

EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

Be sure to follow and tag @JourneyDelivers on LinkedIn and Instagram! 

SUMMARY: 

In this special edition of Choppin' It Up for Black History Month 2025, host Will Jenkins is joined by Justin Turner and Calvin Blackmon to discuss their personal journeys, the importance of advocacy in professional spaces, and the ongoing challenges faced by professionals of color. They share insights on mentorship, the freight industry, and the impact of racism in today's society, emphasizing the need for community support and understanding. In this conversation, the speakers discuss the challenges they face as Black professionals in business, the importance of representation, and the legacy of their ancestors. They share personal experiences of dealing with racism and the impact it has on their motivation and drive. The discussion also delves into the complexities of parenting in a racially diverse world, emphasizing the need for open conversations about race with their children. Finally, they reflect on their achievements and the pride they take in their journeys as successful Black entrepreneurs and executives. 

TAKEAWAYS: 

• Advocacy is crucial for career advancement. 
• Personal journeys often involve unexpected turns. 
• Excellence is required every day for professionals of color. 
• Mentorship differs from advocacy in its approach. 
• Community support can change career trajectories. 
• Racism still exists and impacts professional experiences. 
• Perception can influence opportunities in the workplace. 
• It's important to pay it forward for future generations. 
• Understanding challenges requires empathy and awareness. 
• Professional success often involves navigating biases. 
• Representation is crucial for advancement in business. 
• Racism can manifest in unexpected ways, even online. 
• The legacy of our ancestors fuels our motivation. 
• Parenting requires navigating difficult conversations about race. 
• Children need to understand their unique experiences in society. 
• It's important to control what you can control in life. 
• Success is often a result of perseverance and hard work. 
• Integrity and reputation are vital in professional spaces. 
• Embracing diversity enriches personal and professional environments. 
• Pride in achievements can inspire future generations. 

CHAPTERS: 

• 00:00 Introduction and Team Dynamics 
• 01:42 Personal Journeys and Career Paths 
• 09:29 The Importance of Advocacy in Professional Spaces 
• 15:01 Understanding the Challenges Faced by Professionals of Color 
• 23:11 The Ongoing Reality of Racism and Its Impact 
• 24:50 Facing Racial Challenges in Business 
• 28:20 The Legacy of Our Ancestors 
• 29:47 Navigating Conversations About Race with Children 
• 32:20 The Balancing Act of Parenting in a Diverse World 
• 39:47 Pride in Achievements as Black Professionals 

KEYWORDS: Black History Month, advocacy, mentorship, professional challenges, diversity, personal journeys, freight industry, career paths, racism, community support, racial challenges, representation, legacy, parenting, black professionals, entrepreneurship, integrity, diversity, corporate world, personal growth

EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

Be sure to follow and tag @JourneyDelivers on LinkedIn and Instagram! 

SUMMARY:

In this episode of Choppin' It Up , Marcus Cooksey, CEO and founder of DUKE.ai, shares his journey with Will Jenkins from a challenging upbringing to becoming a successful entrepreneur. He discusses his early education, cultural influences, and the pivotal moments that shaped his career. Marcus reflects on his experiences at Texas Instruments, his entrepreneurial ventures in the trucking industry, and the development of DUKE.ai, which aims to revolutionize document processing through AI technology. The conversation highlights the importance of resilience, adaptability, and the drive to innovate in the face of challenges. In this conversation, Marcus Cooksey discusses the journey of  DUKE.ai, a company focused on automating document processing in the freight industry. He shares insights on the challenges faced during the initial years, the impact of COVID-19, and the evolution of their product offerings, including the introduction of SLIM, a specialized AI for freight document processing. The discussion also covers real-world applications for carriers and factoring companies, emphasizing the importance of adaptability and innovation in the face of industry challenges.

TAKEAWAYS:

• Education plays a crucial role in shaping career paths.
• Entrepreneurship often stems from a desire for independence.
• Financial management is key to sustaining a business.
• Combining skills and technology can lead to innovative solutions.
• Networking and relationships can open doors to opportunities.
• Resilience is essential in overcoming business challenges.
• Identifying market inefficiencies can lead to successful ventures.
• Mentorship and influence can inspire future generations. The inception of DUKE.ai began with a vision in 2017.
• Initial R&D focused on creating a web application for document processing.
• The introduction of automated invoicing was a significant milestone.
• DUKE.ai serves both carriers and factoring companies effectively.
• Automation helps streamline back office processes for carriers.
• The importance of adaptability in the freight industry was emphasized.
• Advice for young entrepreneurs includes embracing the journey and starting early.

CHAPTERS:

• 00:00 Introduction and Background
• 02:53 Cultural Influences and Early Education
• 06:10 Career Beginnings and Early Projects
• 08:57 Transition to Texas Instruments and Key Projects
• 11:55 Entrepreneurial Journey and Trucking Business
• 15:00 Challenges in Business and Financial Management
• 17:56 Development of DUKE.ai and Future Aspirations
• 25:37 The Genesis of DUKE.ai
• 27:47 Building the Product: Challenges and Iterations
• 29:21 Navigating COVID-19: Adaptation and Growth
• 32:12 Expanding Use Cases: From Invoicing to Back Office Automation
• 34:12 Introducing SLIM: A New Era in Document Processing
• 38:22 Real-World Applications: Serving Carriers and Factoring Companies
• 40:16 Streamlining Processes: The Carrier's Journey
• 42:53 The Factoring Side: Automation and Fraud Prevention
• 47:25 Advice for Young Entrepreneurs: Embrace the Journey
• 49:50 Final Thoughts: The Future of DUKE.ai and Industry Insights

EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

Be sure to follow and tag @JourneyDelivers on LinkedIn and Instagram! 

SUMMARY:

In this episode of Choppin' It Up, Will Jenkins interviews Shannon Breen, Co-CEO and Founder of FreightVana. They discuss Shannon's journey from growing up in Oregon to his career in finance and ultimately to the freight industry. Shannon shares insights on the importance of relationships in freight, lessons learned from his time in transportation, and the challenges faced during the mergers. He also talks about the founding of FreightVana and the vision behind creating a differentiated logistics brand. In this conversation, Will Jenkins shares the journey of building FreightVana, a unique freight brokerage that combines technology and equipment to create a differentiated experience in the logistics industry. He discusses the challenges faced in the first year, the importance of customer engagement, and the lessons learned as an entrepreneur. Jenkins emphasizes the significance of authenticity and fulfillment in the workplace, and he looks ahead to future growth and opportunities for the company.

TAKEAWAYS:

• Shannon grew up in a competitive environment, influencing his entrepreneurial spirit.
• His transition to freight was driven by a friend's opportunity at Knight Transportation.
• Building relationships in freight is crucial for success.
• Discipline learned at Knight Transportation has been vital in his entrepreneurial journey.
• The merger with Swift provided valuable lessons in leadership and collaboration.
• Shannon's experience in managing large teams helped him understand business scalability.
• He emphasizes the importance of having the right people around to succeed at scale.
• FreightVana was founded with a focus on creating a differentiated brand in logistics.
• Shannon's past experiences shaped his vision for FreightVana.
• The journey of building FreightVana is seen as a return to the 'league' of logistics. Building from the ground up allows for unique differentiation.
• The first year of a startup is filled with uncertainty and challenges.
• Customer engagement is crucial for growth and validation.
• Authenticity in business fosters strong connections with clients.
• Fulfillment in work is more important than financial success.
• Embracing challenges is essential for entrepreneurial growth.
• Team dynamics can shift, and it's important to celebrate individual successes.
• Reflecting on milestones helps maintain motivation and perspective.
• Investing in technology and equipment can unlock new opportunities.
• The science of grit is vital for assessing potential and success.

CHAPTERS:

• 00:00 Introduction to the Journey
• 02:41 Background and Early Influences
• 04:53 Transitioning to Freight
• 07:07 Building Relationships in Freight
• 11:43 Lessons from Knight Transportation
• 14:07 Navigating the Merger
• 18:31 The Birth of FreightVana
• 25:10 Building FreightVana from the Ground Up
• 28:23 The First Year: Challenges and Triumphs
• 35:16 Turning Points and Customer Engagement
• 41:15 Lessons Learned as an Entrepreneur
• 45:30 Looking Ahead: Future Plans and Growth

EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

Be sure to follow and tag @JourneyDelivers on LinkedIn and Instagram!