We’re celebrating 300 episodes by sharing the most valuable lessons we’ve learned in building a successful freight brokerage. From finding your niche and qualifying leads to building strong carrier relationships and tracking profit—not just revenue—this episode is packed with time-tested strategies. Whether you're new or seasoned, these fundamentals will help you grow smarter and stronger in any market. Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight...
Jun 27, 2025•55 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: 📦 Recommended freight broker software tools to manage rate confirmations, BOLs, PODs, and invoices. 🚚 Strategies for pricing and moving LTL (Less-than-Truckload) shipments. 🥔 What to do when shippers underpay: Can brokers ask for more money without damaging relationships? Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! ...
Jun 24, 2025•21 min
Military logistics is one of the most complex and overlooked areas in transportation. In this episode, we break down how moving freight for the Department of Defense really works—from navigating organizations like SDDC, to managing tight timelines, limited carrier capacity, and high-stakes coordination. You'll also hear firsthand stories and relationship-building tips that can help brokers succeed in this specialized niche. Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: C...
Jun 20, 2025•53 min
Stephen Ruhe & Ben Kowalski answer your freight brokering questions and discuss: 🚆 Export & Domestic Rail Freight - How can brokers source both export and domestic rail freight? 🍁 Moving Hay from Canada to the U.S. - If you’re brokering freight like hay from Canada to the U.S., can you handle customs clearance yourself—or do you need to involve a customs broker or freight forwarder? ❌ Carrier Cancels After Booking – Now What? - What happens when a carrier books a load and then cancels ...
Jun 17, 2025•16 min
Benjamin and Stephen dive into how technology is changing freight brokerage in this episode of Freight 360: Using TMS and automation to boost efficiency Helping small brokerages adopt and improve tech Avoiding the hype and making sure systems actually work Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power - Brokers & Carriers: Click Here Recommended Products: Click Here Freight Broker Basics ...
Jun 13, 2025•1 hr 3 min
Stephen Ruhe & Ben Kowalski answer your freight brokering questions and discuss: ✅ Insurance and surety bond requirements for starting a freight brokerage in Florida 📦 How brokers find loads and the role of load boards vs. direct shippers 🚫 Handling the "we only work with asset-based carriers" objection Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power - Brokers & Carriers: Click Here R...
Jun 10, 2025•23 min
🎧 This Freight 360 episode explores winning brokerage strategies, industry risks, and economic shifts. -Securing more freight through strong communication and customer value -FMCSA identity verification changes and rising fraud concerns -Tariffs, safety budget cuts, and their economic impact -Tech, AI, and personal productivity tips for brokers Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power -...
Jun 06, 2025•54 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: 📦 Are load boards enough? — Can brokers actually find spot market loads directly on load boards, or do they first need to secure customers independently and then post the freight? 📞 Cold call math — Out of 80 outbound calls, how many typically answer on the first try? And how many return the call later? 🔁 From sales to ops — Has anyone successfully transitioned from a pure sales role into an Account Management ...
Jun 03, 2025•21 min
In this episode of Freight 360, we’re joined by Ken Adamo , Chief of Analytics at DAT, and Marcus Womack , CEO and Co-founder of Outgo, to break down the current freight market and DAT’s recent acquisition of Outgo. We discuss how this move enhances payment speed, transparency, and financial control for carriers. Topics include challenges like capacity constraints and high operating costs, plus how Outgo’s tech simplifies back-office operations and factoring. We also explore fraud prevention, th...
May 30, 2025•1 hr 10 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: Freight Broker Certificate Courses Canceling a Freight Brokerage Start-Up Covering Step Deck Loads AI for Freight Brokers Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power - Brokers & Carriers: Click Here Recommended Products: Click Here Freight Broker Basics Course: Click Here Join Our Facebook Group: Click He...
May 27, 2025•37 min
In this episode of Freight 360, we cover key issues in freight and trucking—from 4% of truckers being unlicensed to low freight volumes and economic pressures. They break down double brokering vs. interlining, highlight fraud and safety risks, and explore challenges in trailer rentals, bids, and project management Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power - Brokers & Carriers: Click H...
May 23, 2025•1 hr 2 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: MC Authority Delay? New brokerage struggling on DAT — is 1.5 years to gain traction legit? Broker Contracts Help Lawyer vs. templates — what’s best for new logistics brokerages? Insurance Needed Hard time raising liability to $2M? Here's where to look. Cameron Pechia: [email protected] Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - G...
May 20, 2025•20 min
This episode exposes real cases of internal fraud at freight brokerages—from agents moving loads under fake approvals to inflating commissions and abandoning contracts. Learn how to protect your business with better system controls, document checks, and shared account access. Plus, hear how China’s tariff cuts could shake up freight volumes—and who’s liable when customers don’t pay. Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Ge...
May 16, 2025•1 hr 8 min
In this second segment of 2 part episode, attorney and law professor Matthew Leffler joins the hosts to unpack key legal issues in trucking. They cover non-compete agreements, broker transparency, driver safety, shipper-broker contracts, and recent cases like Werner and Wabash. Leffler shares insights on legal risks, evolving regulations, and how automation could reshape the industry—emphasizing the need for education, clear contracts, and better documentation. Armchair Attorney Matt Leffler Lin...
May 13, 2025•42 min
In this first segment of 2 part episode, attorney and law professor Matthew Leffler joins the hosts to unpack key legal issues in trucking. They cover non-compete agreements, broker transparency, driver safety, shipper-broker contracts, and recent cases like Werner and Wabash. Leffler shares insights on legal risks, evolving regulations, and how automation could reshape the industry—emphasizing the need for education, clear contracts, and better documentation. Armchair Attorney Matt Leffler Link...
May 09, 2025•1 hr 6 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: 🔍 Why brokers request carrier inspections 🧑💼 Is Landstar a good choice for agents? 📦 Best load boards for freight brokers Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power - Brokers & Carriers: Click Here Recommended Products: Click Here Freight Broker Basics Course: Click Here Join Our Facebook Group: Cli...
May 06, 2025•19 min
Poor email habits can cost you customers. In this episode, we break down the fundamentals of professional email communication for freight brokers and why it matters more than you think. 🔹 Write clear, purpose-driven messages 🔹 Use subject lines and recipient lists effectively 🔹 Repackage sloppy carrier emails before forwarding 🔹 Always follow up calls with confirmation emails 🔹 Avoid costly miscommunication and protect your business Listen now and sharpen one of your most overlooked tools i...
May 02, 2025•59 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: Is there a platform where brokers can bid on available freight shipments? What should I do if someone is fraudulently using my MC number to book loads? I'm getting started as a broker, but people say I can't compete with the big guys—any advice? Responding to claims that brokers are "parasites" and the root cause of low rates in the industry. Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: C...
Apr 29, 2025•17 min
When it comes to vetting motor carriers, each freight broker has their own preferences on what to look for and what to avoid. In this episode, we're opening the hood on our own personal rule sets that we use when selecting motor carriers. Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power - Brokers & Carriers: Click Here Recommended Products: Click Here Freight Broker Basics Course: Click Here...
Apr 25, 2025•48 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: Should I be using an official quote form when sending pricing to a customer? Is it realistic to earn $1 million a year as a cradle-to-grave rep handling mostly LTL with 25% commission? When managing LTL and FTL with FedEx and UPS, should I explore alternative shipping options beyond current contracts? Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Ge...
Apr 22, 2025•23 min
In this episode of Freight 360, the hosts break down freight brokering basics with a focus on carrier selection and fraud prevention. They cover how the current economy affects the industry, share a global outlook, and dive into a real case of identity theft. Key takeaways include best practices for vetting carriers, staying ahead of fraud tactics, and the value of training and education in spotting red flags. Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT ...
Apr 18, 2025•50 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: What's the biggest challenge brokers face when it comes to shipping freight? How to find bulk carriers and handle washout requirements. GPS tracking issues: Why isn't it pinging every 30 minutes like it should? Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power - Brokers & Carriers: Click Here Recommended Produc...
Apr 15, 2025•18 min
Ever wonder why some freight brokerages thrive while others constantly struggle with cash flow problems? The answer lies in mastering the fundamentals that many brokers overlook. In this eye-opening episode, we explore the critical but often neglected basics that make or break your brokerage operation. We share real stories of brokerages that generated impressive revenue on paper but collapsed when they couldn't collect payments because of poor documentation practices. You'll discover why verbal...
Apr 11, 2025•58 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: 🔍 How to find the right companies to prospect — and who to contact once you do ⛽️ How to calculate fuel surcharge when quoting a customer 🙈 What blind shipments are and why shippers use them Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power - Brokers & Carriers: Click Here Recommended Products: Click Here Fre...
Apr 08, 2025•19 min
🚚 In this episode, we cover: ⏱ What accessorial charges are (detention, layovers, TONU, lumpers & more) 📄 How to document charges and avoid disputes 📉 Real-world examples of how mishandling accessorials hurts profits and relationships Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power - Brokers & Carriers: Click Here Recommended Products: Click Here Freight Broker Basics Course: Click H...
Apr 04, 2025•1 hr 4 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: 📞 What does “100 calls per day” really mean—total dials or the number of companies contacted? 🚫 Is there a way to get more customers without cold calling? What can a new broker do after struggling with outreach? 💸 When does a shipper typically pay a new brokerage, and how do you cover the carrier payment before you get paid? 🚛 Why would a truck driver change the MC number and company name on the side of their ...
Apr 01, 2025•25 min
Profits can vanish fast when brokers cut corners. Nate kicks things off with a wild National Guard story from inside New York prisons, then we dive into real-life brokerage disasters: a $50K trailer fail, insurance loopholes that killed claims, and a rejected tanker load no one wants to touch. If you’re in freight, these lessons could save your business. Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DA...
Mar 28, 2025•1 hr 4 min
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: Does Your Business Name Matter? – Should you change “Transportation” to “Logistics” when you become a broker? Cold Calling 101 – How to approach shippers as a new broker and what your outreach should sound like. Finding Carriers When You’re New – Strategies to build carrier relationships, even when you lack a credit rating. Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freig...
Mar 25, 2025•21 min
Get 10% off a Year of DAT: Click Here 🔹 DAT Features – Explore qualification settings, company profiles, and market insights. 📊 Leveraging Data Analytics – Use tools like Benchmark & LaneMakers to optimize operations. 📈 Navigating Market Shifts – Learn how seasonal changes impact capacity and pricing. 💰 Boosting Profitability – Improve decision-making with real-time carrier performance tracking. 🎧 Tune in now to stay ahead in the freight game! Support Our Sponsors: QuikSkope - Get a Fre...
Mar 21, 2025•1 hr 7 min
Ben & Stephen answer your freight brokering questions and discuss: Prospecting as a New Broker – Key advice for getting started and landing shippers. Using the BOL for Leads – How to leverage Bills of Lading to start conversations. Building Carrier Trust – Overcoming factoring issues and earning credibility. Support Our Sponsors: QuikSkope - Get a Free Trial: Click Here Levity: Click Here DAT Freight & Analytics - Get 10% off your first year! DAT Power - Brokers & Carriers: Click Her...
Mar 18, 2025•20 min
