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.

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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?

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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.

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AscendTMS: Click Here and use promo code RA-freight360! to get AscendTMS FREE for 90 days!

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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 before pickup?

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DAT Outgo Factoring for Carriers: Click Here

AscendTMS: Click Here and use promo code RA-freight360! to get AscendTMS FREE for 90 days!

Recommended Products: Click Here
Freight Broker Basics Course: Click Here
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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

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DAT Outgo Factoring for Carriers: Click Here

AscendTMS: Click Here and use promo code RA-freight360! to get AscendTMS FREE for 90 days!

Recommended Products: Click Here
Freight Broker Basics Course: Click Here
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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

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DAT Outgo Factoring for Carriers: Click Here

AscendTMS: Click Here and use promo code RA-freight360! to get AscendTMS FREE for 90 days!

Recommended Products: Click Here
Freight Broker Basics Course: Click Here
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🎧 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

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AscendTMS: Click Here and use promo code RA-freight360! to get AscendTMS FREE for 90 days!

Recommended Products: Click Here
Freight Broker Basics Course: Click Here
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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 or Operations role? What trade-offs have you seen in pay and work/life balance?

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DAT Outgo Factoring for Carriers: Click Here

AscendTMS: Click Here and use promo code RA-freight360! to get AscendTMS FREE for 90 days!

Recommended Products: Click Here
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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, the importance of transparency, and what’s needed for a demand-driven market recovery.

Learn More about Outgo today!

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DAT Outgo Factoring for Carriers: Click Here

AscendTMS: Click Here and use promo code RA-freight360! to get AscendTMS FREE for 90 days!

Recommended Products: Click Here
Freight Broker Basics Course: Click Here
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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

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Togo: Click Here

OperFi: Click Here

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DAT One - Brokers & Carriers: Click Here to get 10% off your first year!

DAT Outgo Factoring for Carriers: Click Here

AscendTMS: Click Here and use promo code RA-freight360! to get AscendTMS FREE for 90 days!

Recommended Products: Click Here
Freight Broker Basics Course: Click Here
Join Our Facebook Group: Click Here
Check out all of our content online: Click Here