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How are rising trucking insurance costs quietly driving up your shipping rates and overall freight market pricing? In this episode, Chris Loewenberg from Cottingham & Butler get real about trucking insurance, risk management, and why so many companies treat insurance like a fixed tax instead of a controllable business asset that can either protect or bankrupt your operation!
From the dangers of static COIs and the urgent need for real-time insurance verification technology, to the impact of nuclear verdicts, new carriers, and rising insurance premiums on shipping costs and inflation, this conversation is all about practical freight brokerage insights and proactive strategies.
We also cover how partnering with specialized trucking insurance providers, building stronger safety programs, and collaborating early with insurance partners can reduce uncovered freight risk, improve pricing, and give compliant carriers and brokers a serious competitive advantage in today's trucking industry!
About Chris Loewenberg
Chris Loewenberg is a Vice President at Cottingham & Butler, the nation's largest independent insurance agency dedicated exclusively to the trucking industry. He leads inside sales and technology initiatives focused on small and mid-sized fleets, helping carriers navigate rising insurance costs, increasing complexity, and tighter underwriting scrutiny.
With a background that blends sales leadership, insurance expertise, and technology innovation, Chris works at the intersection of trucking operations, risk management, and data strategy. He partners closely with leading technology vendors across the transportation ecosystem to improve how insurance information is collected, validated, and usedβreducing manual re-keying, accelerating quote turnaround times, and strengthening trust between carriers, agents, underwriters, and technology providers.
In addition to his leadership role, Chris oversees and helps develop Cottingham & Butler's intern and early-career talent programs, working closely with universities and athletic departments to introduce students to sales, insurance, and risk management careers. He is passionate about mentoring young professionals, building high-performing teams, and creating clear development paths from internship to full-time roles.
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ππ Don't miss out on the latest market trends by subscribing to your TOP Transportation Morning Show! π
π¬π― #TheFreightCoach Morning Show is LIVE every weekday at 10:30 AM CST to break down transportation industry headlines! Mark your calendars!
To Find Out More About My Freight Services
Visit https://freightcoachlogistics.com/
π€ Shoutout to my sponsors!π
Donate to support Stacy and her family: https://tinyurl.com/36xmxcmr
ππ₯ To sign up for my Newsletter, go to http://eepurl.com/iNoHco, get in touch with me through the social media channels below, and subscribe to my YouTube Channel!π
βΆοΈ https://www.youtube.com/channel/UCjrL70IEnCfDkNaiYMar3jw
π· https://www.instagram.com/thefreightcoach/
ποΈ https://twitter.com/thefr8coach
πΌ https://www.linkedin.com/in/chris-jolly-a183aa6a/
Are you still treating maintenance as a last-minute repair instead of a long-term fleet strategy? Are mobile mechanics the missing piece to improving fleet uptime, reducing downtime, and controlling maintenance costs?
Let's hear Chris Boyce from Coltrain Onsite Fleet Care speak about how the mobile mechanic industry is growing fast and creating real career opportunities for diesel technicians while helping fleets stay proactive with preventive maintenance that actually lowers the total cost of ownership.
Chris dives into how aligning experienced technicians with the right fleets, using advanced diagnostic tools, and focusing on on-site service helps improve reliability, driver satisfaction, and operational efficiency across transportation and logistics, why tracking key fleet maintenance metrics like PM compliance and downtime is essential for optimizing performance and building strong vendor partnerships, and how Coltrain is expanding nationwide and actively hiring skilled technicians who want autonomy, career growth, and a chance to keep freight moving safely and efficiently!
About Chris Boyce
Chris Boyce brings a rare blend of hands-on technical expertise and senior-level operational leadership to the fleet maintenance industry. He began his career as a technician, quickly distinguishing himself through a strong work ethic, technical excellence, and a natural ability to lead teams. After completing formal management training, Chris successfully combined his field experience with strategic leadership skills to drive performance, accountability, and long-term growth.
Before joining Dickinson Fleet Services, Chris gained valuable experience at Ryder Transportation and within the heavy-duty truck dealer sector, beginning as an entry-level technician and working behind the wrench for 10 years, while developing a deep understanding of fleet operations, customer service, and large-scale maintenance environments. He worked his way up to branch manager, where he started his leadership journey. Following that, he served a seven-year tenure, including the last 4 years as General Manager, at Dickinson Fleet Services/Cox Automotive, where he built the foundation and led one of the company's most successful and productive regions, consistently delivering strong operational and financial results.
Now serving as Regional Vice President at Coltrain Onsite Fleet Care, Chris is known for building high-performing teams, executing at scale, and leading with clarity and purpose. He is widely respected for his ability to align people, process, and performance, and he brings a proven track record of operational excellence to every organization he serves.
ππ Don't miss out on the latest market trends by subscribing to your TOP Transportation Morning Show! π
π¬π― #TheFreightCoach Morning Show is LIVE every weekday at 10:30 AM CST to break down transportation industry headlines! Mark your calendars!
To Find Out More About My Freight Services
Visit https://freightcoachlogistics.com/
π€ Shoutout to my sponsors!π
Donate to support Stacy and her family: https://tinyurl.com/36xmxcmr
ππ₯ To sign up for my Newsletter, go to http://eepurl.com/iNoHco, get in touch with me through the social media channels below, and subscribe to my YouTube Channel!π
βΆοΈ https://www.youtube.com/channel/UCjrL70IEnCfDkNaiYMar3jw
π· https://www.instagram.com/thefreightcoach/
ποΈ https://twitter.com/thefr8coach
πΌ https://www.linkedin.com/in/chris-jolly-a183aa6a/
What's really happening with freight rates right nowβand are you pricing your lanes the right way as capacity tightens? Are new regulations and insurance scrutiny about to reshape carrier operations in 2026?
Today, I break down real-time freight market trends, including stable reefer rates on the Kansas City to Minneapolis lane averaging around $1,285, and why day-of-week pricing strategies are critical for brokers managing customer expectations and protecting margins!
We dig into the rising Minneapolis outbound reefer demand nearing $2,300, the impact of tightening transportation capacity and increased tender rejections in January 2026, plus what Florida's potential $50,000 fines for undocumented drivers and growing compliance enforcement mean for carriers and insurance risk.
Be sure to listen to hear more about the "This Week in Freight" lane analysis segment, delivering actionable DAT-powered pricing insights to help brokers and carriers make smarter decisions, while reinforcing my core philosophyβdisciplined pricing, transparency, and long-term relationship building are the keys to surviving competitive pressure and building a sustainable freight business in today's evolving logistics market!
References / Resources
ππ Don't miss out on the latest market trends by subscribing to your TOP Transportation Morning Show! π
π¬π― #TheFreightCoach Morning Show is LIVE every weekday at 10:30 AM CST to break down transportation industry headlines! Mark your calendars!
To Find Out More About My Freight Services
Visit https://freightcoachlogistics.com/
π€ Shoutout to my sponsors!π
Donate to support Stacy and her family: https://tinyurl.com/36xmxcmr
ππ₯ To sign up for my Newsletter, go to http://eepurl.com/iNoHco, get in touch with me through the social media channels below, and subscribe to my YouTube Channel!π
βΆοΈ https://www.youtube.com/channel/UCjrL70IEnCfDkNaiYMar3jw
π· https://www.instagram.com/thefreightcoach/
ποΈ https://twitter.com/thefr8coach
πΌ https://www.linkedin.com/in/chris-jolly-a183aa6a/
In this episode, The Armchair Attorney Matt Leffler discusses the upcoming Supreme Court case involving C.H. Robinson and why its ruling could finally bring clarity to freight broker liability, negligent hiring claims, and federal preemption under the F4A!
We talk about how conflicting court decisions have created uncertainty for brokers, why the industry relies on FMCSA data to vet motor carriers, and how a ruling against brokers could drive smaller players out of the market due to rising insurance and legal costs.
Matt also covers the growing tension between state tort laws and federal regulation, the role of the US Chamber of Commerce, and what brokers must do right now to manage risk - strict carrier vetting, avoiding operational control over drivers, and staying within established protocols.
This decision will shape broker liability, insurance requirements, and the future structure of the freight industry, and it's something every broker moving freight today needs to understand, so make sure to tune in!
About Matthew Leffler
Matthew is a 3rd generation supply chain executive with over fifteen years of experience in safety, law, & maintenance. Matthew currently serves as Vice President of Strategic Accounts at Contract Leasing Corp. He is also an attorney that provides legal commentary on various supply chain issues & operates a popular podcast. In addition, Matthew has served as a senior leader with some of the nation's most admired maintenance, repair, & fleet management firms. Matthew entered the industry as an attorney defending trucking companies in civil litigation in 2010, but cut his teeth helping build & later selling his family's maintenance firm, Outsource Fleet Services, Inc.
Matthew earned his J.D. from Michigan State University College of Law, Magna Cum Laude, and his B.A. from the University of Illinois Urbana-Champaign. He is licensed to practice law in the State of Illinois; U.S. District Court, Northern District of Illinois; & 7th Circuit Court of Appeals. Matthew is the proud father of Michael, Rowan, Elise, & Elijah & has been happily married to his wife, Holly, since 2008.
ππ Don't miss out on the latest market trends by subscribing to your TOP Transportation Morning Show! π
π¬π― #TheFreightCoach Morning Show is LIVE every weekday at 10:30 AM CST to break down transportation industry headlines! Mark your calendars!
To Find Out More About My Freight Services
Visit https://freightcoachlogistics.com/
π€ Shoutout to my sponsors!π
Donate to support Stacy and her family: https://tinyurl.com/36xmxcmr
ππ₯ To sign up for my Newsletter, go to http://eepurl.com/iNoHco, get in touch with me through the social media channels below, and subscribe to my YouTube Channel!π
βΆοΈ https://www.youtube.com/channel/UCjrL70IEnCfDkNaiYMar3jw
π· https://www.instagram.com/thefreightcoach/
ποΈ https://twitter.com/thefr8coach
πΌ https://www.linkedin.com/in/chris-jolly-a183aa6a/
Are you paying attention to the right lanes, the right technology, and the right relationships in this freight market?
In this episode, I break down why the AtlantaβDallas lane remains one of the most stable in the country, holding between $1,350 and $1,450 with predictable seasonal spikes, and what that means for freight brokers managing tight margins!
We also dig into how AI in freight brokerage is becoming a profitability driver, with companies like C.H. Robinson automating up to 90% of manual tasks to scale efficiently in a down market, how regulatory enforcement and falling carrier profits could trigger capacity exits and support higher rates, why fleets are slowing expansion, and how disciplined brokers can win.
Don't miss out on learning why mentorship from proven freight professionals is critical to avoiding costly mistakes and staying competitive over the next 12 to 24 months!
Resources / References
ππ Don't miss out on the latest market trends by subscribing to your TOP Transportation Morning Show! π
π¬π― #TheFreightCoach Morning Show is LIVE every weekday at 10:30 AM CST to break down transportation industry headlines! Mark your calendars!
To Find Out More About My Freight Services
Visit https://freightcoachlogistics.com/
π€ Shoutout to my sponsors!π
Donate to support Stacy and her family: https://tinyurl.com/36xmxcmr
ππ₯ To sign up for my Newsletter, go to http://eepurl.com/iNoHco, get in touch with me through the social media channels below, and subscribe to my YouTube Channel!π
βΆοΈ https://www.youtube.com/channel/UCjrL70IEnCfDkNaiYMar3jw
π· https://www.instagram.com/thefreightcoach/
ποΈ https://twitter.com/thefr8coach
πΌ https://www.linkedin.com/in/chris-jolly-a183aa6a/
If you're struggling to integrate legacy systems without killing visibility or choose the right TMS partner that actually delivers long-term value, tune in to this episode with Petra Nenickova from Legacy Supply Chain to know what real-world technology integration and digital transformation look like in today's freight environment across the US and Canada!
From managing complex legacy systems and selecting flexible, integration-ready TMS platforms to driving user adoption through frontline involvement, practical training, and ongoing post-launch support, we get into how to evaluate vendors beyond polished demos, why system integrations like EDI and APIs are non-negotiable, how to prioritize core operations at go-live, and why clear communication and change management are the real drivers of ROI, visibility, and scalable freight technology success!
About Petra Nenickova
Petra currently manages the transportation tech stack, including their TMS, and she led several TMS projects from early discovery all the way through implementation. These experiences have taught her a lot about what truly works, what doesn't, and how to guide teams through change with confidence. She's genuinely passionate about both technology and transportation, and she loves the challenge of making systems more effective in supporting real business processes while creating a positive user experience.
With a background in both frontβline operations and management, she understands the everyday challenges people face and what makes technology genuinely useful. She thrives on connecting the dots, solving problems, and helping people work smarter through better processes and better technology.
Connect with Petra
ππ Don't miss out on the latest market trends by subscribing to your TOP Transportation Morning Show! π
π¬π― #TheFreightCoach Morning Show is LIVE every weekday at 10:30 AM CST to break down transportation industry headlines! Mark your calendars!
To Find Out More About My Freight Services
Visit https://freightcoachlogistics.com/
π€ Shoutout to my sponsors!π
Donate to support Stacy and her family: https://tinyurl.com/36xmxcmr
ππ₯ To sign up for my Newsletter, go to http://eepurl.com/iNoHco, get in touch with me through the social media channels below, and subscribe to my YouTube Channel!π
βΆοΈ https://www.youtube.com/channel/UCjrL70IEnCfDkNaiYMar3jw
π· https://www.instagram.com/thefreightcoach/
ποΈ https://twitter.com/thefr8coach
πΌ https://www.linkedin.com/in/chris-jolly-a183aa6a/
Thinking about making the jump from W2 to independent freight agent, or wondering why so many agents struggle to scale and survive in the market?
Erik Larson (Sage) is back on the show to break down what it really takes to succeed as an independent agent in today's freight brokerage and logistics market, starting with mindset, capital, and a realistic business plan for the 1099 transition!
We talk about why revenue diversification is non-negotiable, how relying on one big shipper can put your entire operation at risk, and why your top customers should never control more than 10% of your revenue.
We also cover the operational reality most people underestimate: the need for a full tech stack, proper insurance, legal counsel, and cash flow discipline to handle complex freight contracts and high-value moves.
Don't miss out on hearing why partnering with a strong logistics company like SPI Logistics changed my business, reduced overhead risk, shortened sales cycles, and boosted credibility with larger shippers!
Connect with Sage
YouTube: https://www.youtube.com/@SageOutcastX
ππ Don't miss out on the latest market trends by subscribing to your TOP Transportation Morning Show! π
π¬π― #TheFreightCoach Morning Show is LIVE every weekday at 10:30 AM CST to break down transportation industry headlines! Mark your calendars!
To Find Out More About My Freight Services
Visit https://freightcoachlogistics.com/
π€ Shoutout to my sponsors!π
Donate to support Stacy and her family: https://tinyurl.com/36xmxcmr
ππ₯ To sign up for my Newsletter, go to http://eepurl.com/iNoHco, get in touch with me through the social media channels below, and subscribe to my YouTube Channel!π
βΆοΈ https://www.youtube.com/channel/UCjrL70IEnCfDkNaiYMar3jw
π· https://www.instagram.com/thefreightcoach/
ποΈ https://twitter.com/thefr8coach
πΌ https://www.linkedin.com/in/chris-jolly-a183aa6a/
Find out if EDI is still the backbone of scalable freight operations and what happens when you stop penalizing brokers for growth in this episode with our returning guest, Brad Perling of Bitfreighter!
Brad shares why their EDI-first freight technology strategy is quietly reshaping shipper integration, automated quoting, and brokerage scalability.
Brad and I talk through why EDI remains the most reliable foundation for freight data integrity, how unlimited EDI messaging pricing removes one of the biggest cost barriers for growing brokerages, seamless integration through APIs and RPA across TMS platforms and load boards, and how real-time quoting analytics are driving millions in new revenue for customers.
If you're a freight broker or shipper looking to scale without breaking your tech stack or your budget, this conversation lays out exactly why EDI (if done right) is still a competitive advantage in modern freight tech!
About Brad Perling
Brad Perling is the CEO and co-founder of Bitfreighter. With over 15 years of experience in the industry and growing 2 successful brokerages, Brad's deep understanding of logistics challenges has fueled his passion for finding better software solutions. He knew there was a need for a disruptive new model in the EDI space and was determined to create it. He has a passion for aviation and enjoys playing hockey and golf while spending time with his wife and 2 kids.
Connect with Brad
ππ Don't miss out on the latest market trends by subscribing to your TOP Transportation Morning Show! π
π¬π― #TheFreightCoach Morning Show is LIVE every weekday at 10:30 AM CST to break down transportation industry headlines! Mark your calendars!
To Find Out More About My Freight Services
Visit https://freightcoachlogistics.com/
π€ Shoutout to my sponsors!π
Donate to support Stacy and her family: https://tinyurl.com/36xmxcmr
ππ₯ To sign up for my Newsletter, go to http://eepurl.com/iNoHco, get in touch with me through the social media channels below, and subscribe to my YouTube Channel!π
βΆοΈ https://www.youtube.com/channel/UCjrL70IEnCfDkNaiYMar3jw
π· https://www.instagram.com/thefreightcoach/
ποΈ https://twitter.com/thefr8coach
πΌ https://www.linkedin.com/in/chris-jolly-a183aa6a/
Find out where the human edge and automation matter in freight brokerage in this episode with Alex Schick of Alliance Logistix, sharing how smart freight automation, carrier invoicing automation, and AI in logistics can drive efficiency without sacrificing carrier relationships or customer trust!
Alex talk through why automating tedious tasks like carrier invoicing and document collection speeds payment cycles, reduces errors, and boosts carrier satisfaction, while keeping real humans front and center for load booking and relationship management, why AI should act as an assistant (not a replacement) for brokers, fleets, and driver managers, how tailored transportation technology beats bloated all-in-one systems, and why small fleets can dramatically improve profitability through better cost management, insurance shopping, and maintenance strategies.
If you're a freight broker, fleet owner, or logistics leader trying to balance automation with personal service while protecting margins in a tight market, this conversation is full of practical insights you can apply immediately!
About Alex Schick
Alex embarked on his logistics adventure in 2007 at Intransit, which later transformed into DSV Road through several acquisitions. Starting from the bottom in tracking and tracing, he quickly climbed the ranks. By 2009, he was overseeing a small region of freight in Northern California. His responsibilities expanded significantly by 2014, when he began handling all customer bids, pricing, and rate structures for carriers. At that point, he also managed the operations side of about 40% of the branch's freight.
In early 2017, he became the branch manager, overseeing the overall strategy and direction of the entire branch. From 2014 to the end of 2018, they grew from 7,000 truckloads per year to 55,000 truckloads per year as an agency. They expanded from 6 employees to 18 and from $5 million in revenue to almost $20 million. They were a bootstrapped company growing like crazy before the tech boom hit the industry.
He left DSV in 2019 and joined Wilson Logistics in 2020. Together with his wife, Natalie, they started to rebuild. By the end of 2020, they had hired their first employee in their Wilson Agency. In early 2023, they departed the agent model and co-founded Alliance Logistix LLC. By late 2023, they ventured into asset-based trucking alongside their brokerage. Today, they have 12 employees in the brokerage, 7 drivers, and 2 employees at their asset company. They are currently handling volumes of more than 30,000 truckloads annually.
With nearly two decades of industry experience, he's committed to fostering strong relationships, building alliances, and identifying synergies with their customers and carriers. They are focused on being a lean as possible, efficient as possible, and eliminating and/or automating repetitive and monotonous tasks with technology and automation. The most important thing is that they are keeping to their roots of the family feel for their customers, carriers, and employees alike. After all, in logistics, it's all about the journey and the company you keep!
Connect with Alex
ππ Don't miss out on the latest market trends by subscribing to your TOP Transportation Morning Show! π
π¬π― #TheFreightCoach Morning Show is LIVE every weekday at 10:30 AM CST to break down transportation industry headlines! Mark your calendars!
To Find Out More About My Freight Services
Visit https://freightcoachlogistics.com/
π€ Shoutout to my sponsors!π
Donate to support Stacy and her family: https://tinyurl.com/36xmxcmr
ππ₯ To sign up for my Newsletter, go to http://eepurl.com/iNoHco, get in touch with me through the social media channels below, and subscribe to my YouTube Channel!π
βΆοΈ https://www.youtube.com/channel/UCjrL70IEnCfDkNaiYMar3jw
π· https://www.instagram.com/thefreightcoach/
ποΈ https://twitter.com/thefr8coach
πΌ https://www.linkedin.com/in/chris-jolly-a183aa6a/
Are you confident your compliance program would hold up under an FMCSA audit, and are you scaling your fleet without scaling your safety and risk management? Rob Carpenter from Trucksafe is back to discuss why organized compliance, defensible training, and real accountability are no longer optional in trucking!
We explore how poor paperwork and weak policies can turn routine inspections into costly enforcement actions, why nearly 80% of driving skills are learned on the job (and how this creates serious legal exposure), and the growing accountability gap where drivers face severe penalties while carriers often escape consequences.
We also cover FMCSA compliance reviews, ELD scrutiny, the role of technology in growing fleets, and why proactive safety training reduces accident severity and litigation risk.
As regulatory scrutiny increases and bad actors face more exposure, carriers that invest in scalable compliance programs, driver training, and transparent documentation are the ones best positioned to protect their business and stay competitive in today's freight industry!
Connect with Rob
ππ Don't miss out on the latest market trends by subscribing to your TOP Transportation Morning Show! π
π¬π― #TheFreightCoach Morning Show is LIVE every weekday at 10:30 AM CST to break down transportation industry headlines! Mark your calendars!
To Find Out More About My Freight Services
Visit https://freightcoachlogistics.com/
π€ Shoutout to my sponsors!π
Donate to support Stacy and her family: https://tinyurl.com/36xmxcmr
ππ₯ To sign up for my Newsletter, go to http://eepurl.com/iNoHco, get in touch with me through the social media channels below, and subscribe to my YouTube Channel!π
βΆοΈ https://www.youtube.com/channel/UCjrL70IEnCfDkNaiYMar3jw
π· https://www.instagram.com/thefreightcoach/
ποΈ https://twitter.com/thefr8coach
πΌ https://www.linkedin.com/in/chris-jolly-a183aa6a/
From the publisher's feed

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