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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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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🎧 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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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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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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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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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

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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]

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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.

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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 LinkedIn

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