Contractor Chaos: Fixing the Last Mile's Biggest Headache with Jon Doolen
The Logistics of Logistics Podcast
Release Date: 03/25/2025
The Logistics of Logistics Podcast
and discuss a decade of Loadsmart: a look back to move forward. Felipe is Co-founder and CEO of , where they provide logistics solutions powered by industry experts and next-gen technology that lower costs, increase efficiency, and digitize transportation. About Felipe Capella Co-founder and CEO of , a leading digital freight technology company. Previously advised companies on corporate strategy and M&A in Brazil and New York for 8 years. Joined the Inter-American Development Bank in Washington to advise on sovereign guaranteed development...
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and discuss beyond the yard - how Velostics streamlines scheduling. Gaurav is the Founder and CEO of , a company on a mission to revolutionize the logistics landscape. Summary: Beyond the Yard: How Velostics Streamlines Scheduling In this podcast, Gaurav Khandelwal, CEO of Velostics, discusses how their cloud-based logistics software automates scheduling and streamlines processes for shippers, carriers, and logistics providers. Velostics aims to eliminate manual scheduling, reduce friction in the handoff process, and provide user-friendly tools for better...
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In “The 5 Failures of Final Mile,” and , Host of Last2First Podcast and Insurance Producer at CUI Agency, discuss the common mistakes that final mile companies make. About Jason Burns is a native of New Orleans and a passionate business leader in the final mile transportation industry. He is a 2006 graduate of Vanderbilt University where he was a SEC Academic Honor Roll student-athlete in football and selected as the recipient of the Head Coach’s Dedication Award. After beginning his professional career in the parking industry, Jason returned to his hometown to assume a...
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In "TIA Unpacks Freight: Tariffs, Trust, and the Fight Against Fraud," and , President and CEO of the Transportation Intermediaries Association (TIA), dive into key industry topics. About Chris Burroughs is the President and CEO of the Transportation Intermediaries Association (TIA), a position he assumed in November 2024. With over 14 years at TIA, he previously served as Vice President of Government Affairs, overseeing legislative and regulatory efforts before Congress and federal agencies. Before joining TIA, Burroughs gained valuable experience on Capitol Hill, working for the House...
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and discuss RocketFuel: Fintech for fulfillment. Braden is the Co-founder and CEO of Launch Fulfillment and RocketFuel, two high-growth companies transforming the logistics and fintech landscapes. About Braden DiCristofano is the Co-founder and CEO of Launch Fulfillment and RocketFuel, two high-growth companies transforming the logistics and fintech landscapes. Raised in Pleasant Grove, Utah, he served a two-year mission in Jacksonville, Florida, before attending Ensign College. Braden began his career in sales, gaining nine years of experience in sales and leadership—skills that laid the...
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and discuss the container payment portal and the rise of AI in freight. Jake is the Chief Technology Officer of Gnosis Freight, a logistics tech company focused on the lifecycle of a shipping container as it moves around the world. About Jake Hoffman is the Chief Technology Officer of Gnosis Freight, a logistics tech company focused on the lifecycle of a shipping container as it moves around the world. He has led the engineering team since the company's inception in 2017, bringing a deep understanding of technology and trends in the industry to bear in driving the company's technical...
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and discuss from ports to politics: decoding tariffs, ocean shipping, and supply chains. Sal is is an associate professor of history at Campbell University in North Carolina and adjunct professor at the U.S. Merchant Marine Academy. About Sal Mercogliano is an associate professor of history at Campbell University in North Carolina and adjunct professor at the U.S. Merchant Marine Academy. He holds a Bachelor of Science in marine transportation from the State University of New York Maritime College, along with a merchant marine deck officer license (unlimited tonnage 2nd mate), a...
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and discuss delivering the drinks: streamlining beverage transportation. Kristina is the Director of Operations at Bettaway, a privately held, family-owned Supply Chain Services company headquartered in South Plainfield, New Jersey. Kristina and the Bettaway team are big supporters of Wreaths Across America. About Kristina Bernarducci isn’t just building partnerships—she’s building community. As Director of Operations at Bettaway and Director of Business Development at PalletTrader, Kristina brings energy, creativity, and a drive for results to the world of logistics and supply...
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and discuss global giants - ICAT moves the world's largest cargo. Chris is the Director of Operations at ICAT Logistics Detroit where they handle the shipments that other companies don't, can't, and won't. Summary: Global Giants: ICAT Moves the World's Largest Cargo In this podcast, Chris Cser, Director of Operations at ICAT Logistics, takes us on a journey through the complex world of global logistics. Founded in 1992 in Baltimore, ICAT Logistics has expanded across the United States and Europe, specializing in handling unusual, high-value, and oversized freight that often falls outside the...
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and discuss the people-first approach to the future of logistics. Michael is a Partner at Hyde Park Angels (HPA), a leading early-stage investor based in Chicago. About Michael Sachaj is a Partner at HPA and manages and supports HPA’s investment opportunities through their lifecycle. Michael has led investment in a number of HPA’s top performing investments including ShipBob, FourKites, Paccurate, and Digit. Prior to joining HPA in 2013, Michael attended Northwestern University and worked at strategy consulting firm Booz Allen Hamilton supporting various government clients in the...
info_outlineJon Doolen and Joe Lynch discuss contractor chaos: fixing the last mile's biggest headache. Jon is a Strategy Leader at Doolen Strategy Partners that specializes in providing leadership development programs, business advisory services, and public speaking engagements.
About Jon Doolen
Jon Doolen is a seasoned business coach with over two decades of expertise in retail logistics, particularly specializing in final mile delivery and third-party logistics for home furnishings and luxury products. Jon's background includes extensive work with major names in the industry, where he's earned a reputation for solving toxic work environments, setting strategic goals for career growth, and aligning personal aspirations with professional success. His approach blends leadership development with a deep commitment to continuous learning, emphasizing integrity and wholesome values in all aspects of business and life. Jon's motivational style and practical wisdom resonate through his coaching, training programs, and writing, encouraging others to embrace change, enhance team dynamics, and achieve sustainable business outcomes. He is also a dedicated advocate for military veterans transitioning to civilian careers, reflecting his broader commitment to supporting personal and professional growth across diverse sectors.
About Doolen Strategy Partners
Doolen Strategy Partners specializes in providing leadership development programs, business advisory services, and public speaking engagements. With a focus on operations management, particularly in final mile retail home delivery, warehousing, and distribution, the firm helps businesses optimize their processes, develop strong leadership teams, and drive continuous improvement. Through strategic guidance, Doolen Strategy Partners aims to elevate business performance and foster growth in a competitive market.
Key Takeaways: Contractor Chaos: Fixing the Last Mile's Biggest Headache
- Jon Doolen and the GetDoolen Team help 3PLs and driver contractors navigate the following:
- Navigating the Contractor Conundrum: Uncover the critical gaps in business acumen, customer service, and regulatory compliance that often plague last-mile delivery contractors, and learn how these deficiencies can jeopardize your logistics operations.
- Mitigating Legal and Liability Risks: Explore the potential legal pitfalls and financial liabilities logistics companies face when partnering with under-prepared contractors, including the ever-present threat of misclassification and subsequent lawsuits.
- Safeguarding Your Customer Experience: Understand the direct correlation between contractor professionalism and customer satisfaction, and discover strategies to ensure consistent, high-quality delivery services that protect your brand reputation.
- Veteran Leadership: Jon Doolen, a U.S. Army Quartermaster Corps veteran, founded Doolen Strategy Partners, bringing military discipline and leadership principles to his business.
- Expert Leadership Development & Coaching: With over 30 years of experience, Jon offers comprehensive coaching services, including career, business, and specialized "Final Mile" coaching, focused on personal and professional growth.
- Personalized Mentoring & Brand Building: Doolen Strategy Partners provides tailored mentoring and strategies for personal brand development, resume enhancement, and interview preparation, empowering clients for career success.
- Thought Leadership & Engagement: Jon fosters leadership dialogue through roundtables, conversations, and motivational speaking, sharing his expertise and inspiring action across industries.
Learn More About Contractor Chaos: Fixing the Last Mile's Biggest Headache
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