Freight 360
It's the Freight360 podcast from Freight Broker Sales tips to Sports Talk. This podcast is all about helping you grow as a Freight Broker with your hosts, Nate Cross and Benjamin Kowalski. New episodes every Friday and our Q&A series "The Final Mile" every Tuesday.Join us as we dive into the freight industry to provide you with the latest in Freight Broker education and industry news.If you have a question you would like answered on our show visit the website below or leave a comment wherever you get your podcasts.Visit our website www.freight360.net for o...
Freight Claims Explained | Episode 347
A rejected load can quickly become a five-figure loss, and the outcome often comes down to documentation, evidence, and how the claim is handled from the start. We break down freight claims, OS&D, cargo insurance, reefer issues, USDA inspections, carrier cooperation, and the practical steps brokers can take to prevent small mistakes from turning into expensive disputes.
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<...The Pipe Stake Hustle That Won A Customer | Final Mile 146
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
🏗️ Pricing steel coil loads and accounting for added challenges
🚛 Fair owner-operator splits, insurance, and operating under your MC
📞 Overcoming the “customer-routed” or “vendor-routed” objection
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Your SOPs Only Work When You Enforce Them | Episode 346
One bad shortcut can turn a routine load into a claim, stolen freight, or a cash-flow disaster. We break down how brokerages should handle policy violations, strengthen SOPs, use technology to reduce risk, and determine when mistakes are correctable versus grounds for immediate termination.
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Real-World Crisis Calls In Freight Brokerage | Final Mile 145
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
⚠️ Handling carrier threats professionally
✅ Building defensible carrier vetting
📈 Responding to rising rate pushback
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Freight Brokerage Finance From Startup Costs To Profit | Episode 345
Freight brokerage is often called a sales game, but the brokers who last understand the finance behind every load. In this episode, we break down margins, startup costs, cash flow, hiring, compensation models, and the money decisions that help brokerages survive rate swings and grow profitably.
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How Much Risk Can A Broker Really Ignore | Final Mile 144
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
🚛 Why brokers hide commodity details from new carriers
⚠️ What brokers fear most with new MCs
📋 Can brokers verify cargo exclusions before onboarding carriers?
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Modern Day Carrier Vetting That Protects Freight Brokers | Episode 344
DOT Blitz Week inspections sideline roughly one out of every three trucks, tightening capacity and driving spot rates higher across all equipment types. In this episode, we break down what those out-of-service numbers really mean, how broker liability and negligent hiring are evolving after recent court rulings, and why your carrier vetting process needs to be practical, documented, and built around the data brokers actually have access to.
We also cover how to interpret CSA scores, where carrier vetting tools like Highway and RMIS help or fall short, and how to build a scalable compliance workflow that...
Who Pays When Freight Rates Rise | Final Mile 143
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
📈 Are shippers absorbing higher freight rates?
📞 When brokers ghost detention rate updates
📞 Five-month broker wants honest progress gut check
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Broker Liability After The Supreme Court Ruling (with Danielle Spinelli) | Episode 343
The Supreme Court’s 9-0 decision in Montgomery v. Caribe Transport II, LLC just changed the liability conversation for freight brokers, especially around negligent hiring and what “reasonable care” really means. We sit down with Danielle Spinelli from GenLogs to break down the ruling, the limits of carrier safety data, and why brokers need a documented, provable carrier vetting process before claims, insurers, shippers, and regulators start asking harder questions.
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Is AI In Your TMS Helping Or Risking Everything | Final Mile 142
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
📄 Starting A Brokerage + Factoring Questions
🚛 Handling Carrier Deadhead Pay Requests
🤖 Using AI To Automate Brokerage Operations
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What Contingent Cargo Insurance Actually Covers | Episode 342
Most freight insurance problems start long before a claim ever happens. In this episode, we break down contingent cargo insurance, coverage gaps, excluded commodities, theft claims, and why many brokers and carriers misunderstand what’s actually protected when freight moves. We also cover practical risk management strategies for verifying coverage, handling high-value freight, and avoiding costly surprises when a shipment goes sideways.
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If The Carrier Breaks Down, How Do We Settle The Bill? | Final Mile 141
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
🚛 Carrier Breakdown Payment Dispute
🏢 Selling An Inactive Trucking Authority
📉 Broker Lowered Rate After Agreement
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Reco...
How To Scale A Brokerage With SOPs, Outsourcing, And Applied AI | Episode 341
Your brokerage doesn’t need more shiny tools. It needs systems that actually match the reality of freight operations. In this episode with the Togo crew, we break down why so many logistics AI tools fail, what automation actually works for brokers, and how SOPs, process mapping, and smarter staffing can help teams scale without sacrificing service.
We also look ahead at the future of AI in freight brokerage, including data ownership, vendor lock-in, and why smaller brokerages that start building now may have the biggest advantage.
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...Tracking, Check Calls, Sending Photos. Is It Too Much? | Final Mile 140
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
🤝 Co-brokering with different factoring companies: possible?
⚠️ FreightGuard report removal help needed
📡 Carrier frustrated with tracking, communication overload
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Carrier Sales: Stop Losing Money On Loads | Episode 340
Margins don’t randomly drop to 3% - it usually comes from poor carrier sourcing, weak vetting, and sloppy execution. Tighten your carrier sales process, use real market data, and guide shippers with clear options to protect both margin and service.
At the end of the day, pay for the right carrier, manage risk proactively, and avoid cutting corners that turn small issues into expensive problems.
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Buying A Trucking Company Can Reset Your Credibility | Final Mile 139
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
Changing factoring companiesThe impacts of selling an MCRail rates vs. Van ratesDefault settings in your TMSSupport Our Sponsors:
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Scaling A Freight Brokerage | Episode 339
You can have authority, a license, and customers—but still not have a real brokerage, just a founder doing everything until growth turns into chaos. Scaling usually fails not from lack of freight, but because the operation can’t handle the volume without structure, clear roles, and strong leadership.
We break down how to build processes, avoid common hiring mistakes, and stop being the bottleneck so your business can actually grow.
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Spot Market Pricing For Freight Brokers | Final Mile 138
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
💰 Carrier rates, margins, shipper pricing basics
⏱️ Handling unexpected 24-hour trailer drops
🔍 Alternatives to Highway for carrier vetting
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60 Minutes Investigates Chameleon Carriers - Here’s The Real Story | Episode 338
We break down the 60 Minutes investigation into chameleon carriers and the Super Ego allegations, adding real-world industry context on what’s legit vs. outright fraud—and why weak onboarding and identity verification create major vulnerabilities.
From rate con fraud to ELD manipulation, we cover how these schemes work and share practical broker SOPs and vetting strategies to catch red flags early and protect your business.
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How To Price RFP Freight When The Market Flips & More Q&A | Episode 337
Freight markets flip fast—one week you’re competitive, the next you’re underwater—so we break down how to price RFP and contract freight, manage risk, and avoid paper rates. We also cover tracking tech that actually works, plus the realities of being a 1099 agent and what separates brokers who thrive from those who burn out.
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Rate Cons That Prevent Surety Bond Claims | Final Mile 136
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
⚖️ Fining Carriers The Right Way vs Wrong Way
🚛 Dispatch Services: Pros & Cons
🌴 Florida Peak Season Strategy
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How To Teach A Dispatcher To Cover Loads Without Guesswork | Episode 336
Most brokers don’t stall because they can’t sell—they stall because they’re stuck doing ops and don’t know how to train help without losing quality. This episode breaks down how to hire and train a dispatcher so you can scale without burnout.
We also cover the current market—tight capacity, rising rates, and spot vs. contract tension—and walk through a practical dispatcher workflow, carrier sourcing, and negotiation tactics that actually work in today’s environment.
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"Cash App Me The Money And Trust Me Bro" | Final Mile 135
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
💸 Getting Paid via Cash App? Is it normal or a red flag for carriers?
📊 Best Way to Find Loads? Are load boards enough or is there a better strategy?
⚖️ Broker Bankruptcy? File on the bond only or use a collection agency too?
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Your “Full Integration” That Does Nothing | Episode 335
“Integrated” freight software isn’t always as seamless as it sounds. We break down where TMS integrations fall short—and how those gaps can lead to stolen loads, compliance misses, or hidden service issues.
We cover what to ask about carrier vetting tools, why timing and visibility matter, and how terms like API vs. webhook impact real-time data. Bottom line: messy data doesn’t get fixed by better tech or AI—it just scales the problem.
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Factoring Fees, Fuel Surcharges, And Freight Weight | Final Mile 134
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
💳 Best factoring companies and typical freight broker factoring rates
⛽ What happens to fuel surcharges when diesel prices rise
⚖️ Why shipment weight matters so much to motor carriers
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Preventing Claims Nightmares With Simple Proof | Episode 334
A single freight claim can wipe out a month of profit if the basics aren’t handled right. In this episode, we break down why claims spiral—unclear ownership, weak documentation, missing PODs, and insurance blind spots—and share real examples of where things went wrong and how to prevent them.
We also cover the key checkpoints at pickup and delivery, how FOB terms affect responsibility, and why relying on contingent cargo or reefer breakdown coverage can backfire. The solution: tighter carrier vetting, clearer rate confirmations, and a solid claims playbook to protect your margins.
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How Clear Policies On Detention And Layover Save Headaches | Final Mile 133
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
⏰ Shipper delay until night — driver left. Is TONU owed?
📅 Broker changed appointment mid-load — who owes detention?
💸 $400 for 1,200 miles with driver assist — fair?
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What Not To Do And How To Make Shippers Want To Call You Back | Episode 333
🤝 Build Trust First: Sales in freight brokerage are built on genuine conversations, active listening, and understanding customer expectations. By avoiding “commission breath,” communicating transparently, and building real personal connections, brokers can create long-term relationships and a healthier sales pipeline.
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Contracted Lanes In A Volatile Freight Market | Final Mile 132
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
📦 Contracted lanes worth it in today’s freight market?
📈 Cheap freight ending — raise rates and reset expectations
🏢 Using spouse’s authority vs getting your own MC?
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How Tight Capacity, Changing Rules, And Smarter Vetting Is Reshaping Freight Brokerage | Episode 332
Freight is tightening for real reasons as enforcement and compliance crackdowns pull trucks out of circulation and spot rates start outrunning contract freight. We talk about balancing strong carrier vetting with practical flexibility, and why automation still needs human judgment when capacity gets tight. We also break down how to reset shipper pricing using real market data and a simple “What, So What, What Now” discussion, plus practical ways to win more freight through better execution and smarter prospecting.
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Who Pays When A Load Falls Apart? | Final Mile 131
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
🪪 Why brokers request driver CDL
📊 Essential TMS reports to run
🚛 In-transit breakdown: who pays loss
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...Should You Be A Freight Broker In 2026? | Episode 331
We weigh whether 2026 is the right time to start or double down on a freight brokerage, then map the forces moving the market: rising spot rates, falling volumes, and compliance crackdowns that are shrinking capacity. We dig into fraud tactics, why over‑automation backfires, and how small daily habits turn volatility into opportunity.
• rising spot rates against lower shipment volumes
• compliance enforcement and capacity exits
• reefer and van spot rates nearing or beating contract
• produce season impacts and regional tightness
• where automation helps and where it fails
• fraud patterns, carrier vetting, and human checks
Hiring An Agent Or Growing Solo | Final Mile 130
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
🚛 Should a solo broker hire an agent?
🆕 When would you use new carriers?
💳 How to build brokerage credit fast?
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How Smart Freight Brokers Turn Follow-Ups Into Revenue | Episode 330
Cold calls get attention, but follow-up is where deals are won. We break down a simple, repeatable system to turn first touches into trusted shipper relationships using sharp recaps, smart timing, and notes that make every call build on the last.
We cover how to log key personal and operational details in your CRM, set the next step before hanging up, use market signals to add timely value, and communicate early and honestly when conditions shift—so you move from “price check” to trusted partner.
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Motor Carrier Insurance & More Q&A | Final Mile 129
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
🚚 Can shippers use load boards?
📝 Any autos vs scheduled autos COI?
📦 Claim filed 2 weeks post-delivery?
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Freight Market Turning Point (with Dean Croke from DAT) | Episode 329
In this episode of the Freight 360 podcast, hosts Nate Cross and Ben Kowalski discuss the current state of the freight market with Dean Croke from DAT. They explore recent trends, regulatory changes affecting the industry, and safety concerns on the road. The conversation highlights the impact of enforcement on carrier attrition and the upcoming produce season, emphasizing the need for improved driver training and awareness.
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How Many Cold Call Should New Freight Brokers Make? | Final Mile 128
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
❄️ Why post undeliverable loads during lingering winter storms?
🚚 Are vans or reefers rejected due to age?
📞 What activity and call expectations exist at large brokerages?
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Prospecting New Shippers Without The Pressure | Episode 328
Your rate isn’t your edge—your communication is: we teach a pressure-free prospecting system that starts with real shipper problems, builds trust early, and works when storms, tight capacity, and chaos hit. You’ll learn how to call with relevance (not price), tune delivery and silence, handle “not onboarding,” pivot by season/equipment, and use tools like DAT and Blue Book to turn market reality into opportunity. If you want to prospect without sounding salesy and build a pipeline that calls you back, press play—and share it with a teammate.
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Tips for New Freight Brokers | Final Mile 127
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss:
💸 Tax tips for brokers?
🧠 Where do you get sample rate cons?
🧾 What TMS auto-creates rate cons/forms?
📂 What broker forms do you keep?
🚛 How do you vet carriers?
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Building A Freight Sales Team | Episode 327
A brutal ice storm is set to ice over the South, squeezing capacity, delaying service, and pushing rates from Texas to the Carolinas—so we start by breaking down what that really means for freight. Then we get into a numbers-first playbook for building a brokerage sales team that performs under pressure: W-2 vs agent economics, onboarding timelines, call and CRM metrics that matter, clear GP milestones, and disciplined coaching so your team can turn disruption into durable shipper relationships.
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