Freight Agent Insider Podcast

With Levi Van Pay

The Freight Agent Insider Podcast is hosted by Levi Van Pay, a social media personality and Director of an agent based brokerage delivering weekly insights and stories, featuring the best freight agents in the industry. Made for aspiring and experienced freight agents alike, each weekly 30 minute episode tackles one key topic— from breaking into the industry to mastering negotiations— with practical tips, real-world stories, and actionable advice. Subscribe for insider knowledge!

  1. 6d ago

    Episode 61: Jordan Galloway- From Rockstar Drummer To Truck Driver | Freight Agent Insider

    This week on Freight Agent Insider, Levi Van Pay welcomes Jordan Galloway, the “Cowgirl of Cargo,” for a candid conversation about trucking, freight brokerage, entrepreneurship and building a business through relationships. Jordan shares her journey from professional drummer to truck driver to freight broker, including driving 53-footers, hauling for Anheuser-Busch and launching Galloway Coast to Coast. She explains how being a driver shaped her approach to freight, why respect and empathy for truck drivers matter and how she builds customers through face-to-face relationships instead of relying solely on cold calling. Jordan also shares her vision for building one of the most trusted transportation companies, with a focus on compassion, relationships and putting a face behind the business. 🔥 KEY TAKEAWAYS: • From drummer to truck driver to freight broker • Why driver experience creates better brokers • Building customers through relationships • Respect and empathy in the freight industry • Growing Galloway Coast to Coast with trust at the center • Advice for women entering trucking ⏱️ IMPORTANT MOMENTS: 00:00 – Intro & Freight Agent Expo 02:57 – Meet the “Cowgirl of Cargo” 04:16 – From Driver to Freight Broker 05:53 – Drummer to Truck Driver 09:12 – Starting Galloway Coast to Coast 11:50 – Respect & the Driver Perspective 17:04 – Brokers & Driver Relationships 24:04 – Building a Trusted Company 25:26 – Arizona, California & Sales 30:20 – Entrepreneurship & Hard Work 31:52 – Advice for Women in Trucking 32:59 – Closing Thoughts34:00 – Outro 🎧 Available now on Spotify, Apple Podcasts, YouTube & all major podcast platforms. 🔔 Follow Freight Agent Insider for weekly conversations covering freight, logistics, trucking, sales, leadership, entrepreneurship and business growth. This episode was brought to you by FreightDeck. It is the all-in-one heavy haul estimating tool that instantly calculates the full cost of any move. Covering permits, pilot cars, police escorts, route surveys, bridge studies and bucket trucks across every state and Canada. Discover it for yourself at ⁠thefreightdeck.com⁠. This episode was brought to you by Freight Scout. The AI platform that runs the whole load for freight brokers, from finding the shipper to getting paid. Check them out at ⁠freightscout.ai. #freight #logistics #freightbroker #freightagent #freightagentinsider #jordangalloway #gallowaycoasttocoast #trucking #truckdriver #womenintrucking #freightbrokerage #entrepreneurship #freightdeck #freightscout

  2. Oct 19

    Episode 60: Colby & Raegan Baskin Pt 2- Building a Freight Agent Brokerage | Freight Agent Insider

    This week on Freight Agent Insider, Levi Van Pay welcomes back Colby and Raegan Baskin of Cowtown Logistics for a powerful conversation about freight brokerage, the agent model, recruiting, leadership, culture and building a business through adversity. Colby and Raegan share how Cowtown went from a trucking operation with approximately 60 trucks and 100 flatbed trailers to facing $5 million in debt, selling the trucking assets and refocusing entirely on freight brokerage. Today, Cowtown is running at approximately $72 million, with a goal of reaching $100 million and ultimately building toward $250 million. The episode explores why Colby believes the agent model could have accelerated their growth, how Cowtown attracts and retains freight agents and why genuine relationships often matter more than aggressive recruiting. 🔥 WE ALSO DISCUSS: • From Trucking to Brokerage: Colby and Raegan's journey into freight • The $5K Startup: Building Cowtown from the ground up • Millions in Debt: Lessons from their trucking operation • LinkedIn & Authenticity: Growing through relationships and consistency • Recruiting & Retention: Finding and supporting great agents • Agent vs. Brokerage: Lessons from both sides of the industry • Culture & Leadership: Scaling without losing the personal touch • The $250M Vision: Cowtown's plans for the future• Advice for Young Professionals: Getting started in freight 👇 COMMENT BELOW: What matters most when choosing a freight agency—commission, support, culture or growth opportunities? ⏱️ IMPORTANT MOMENTS: 00:00 – Intro & Freight Agent Expo Announcement 03:21 – Welcome Colby & Raegan Baskin 04:20 – Their Journey Into Freight 06:40 – The $5K Brokerage Startup 07:54 – 60 Trucks, 100 Trailers & Millions in Debt 10:10 – LinkedIn & Building the Cowtown Brand 12:34 – Recruiting Large Agents 15:18 – What Sets Cowtown Apart 19:36 – Agent Retention & Support 23:34 – Advice for the Next Generation 25:03 – Agent vs. Brokerage 28:25 – Growth & Culture 31:15 – $100M Goal & $250M Vision 32:56 – Gratitude & Final Advice34:20 – Outro 🎧 Available now on Spotify, Apple Podcasts, YouTube & all major podcast platforms. 🔔 Subscribe for weekly conversations on freight brokerage, logistics, leadership, sales, entrepreneurship, freight technology, AI and business growth. This episode was brought to you by FreightDeck. It is the all-in-one heavy haul estimating tool that instantly calculates the full cost of any move. Covering permits, pilot cars, police escorts, route surveys, bridge studies, and bucket trucks across every state and Canada. Discover it for yourself at thefreightdeck.com.  This episode was brought to you by Freight Scout. The AI platform that runs the whole load for freight brokers, from finding the shipper to getting paid. Check them out at freightscout.ai #freight #logistics #freightbroker #freightagent #freightagentinsider #cowtownlogistics #colbybaskin #raeganbaskin #freightbrokerage #trucking #leadership #sales #recruiting #entrepreneurship

  3. Oct 12

    Episode 59: Ryan Nolan- A Freight Agent Legend: Leaving A Freight Legacy | Freight Agent Insider

    This week on Freight Agent Insider, host Levi Van Pay sat down with Ryan Nolan, freight agent and founder of Flow State, for an insightful and entertaining conversation about the evolution of freight brokerage, the rise of independent agents, AI automation, authenticity and what it really takes to build a lasting career in logistics. Ryan shares his journey from graduating without a clear career path and finding a freight broker job on Craigslist to spending 16 years in the industry, working across carrier sales, operations, customer-facing roles, W-2 brokerages and eventually launching his own agency, Flow State. The conversation dives deep into one of the biggest questions facing freight professionals today: Is the traditional brokerage model becoming less necessary? Ryan explains why he believes technology and automation are giving independent agents more leverage than ever before—and why the idea of a one-person $100M freight agency may not be as crazy as it sounds. Ryan and Levi discuss AI-powered freight tools, rebuilding a book of business, LinkedIn personal branding, sales, recruiting, contracts and the power of authenticity and perseverance. Whether you're a W-2 broker, freight agent, or aspiring logistics professional, this episode offers practical insights on technology, relationships and building your own path. 🔥 KEY TAKEAWAYS: • From Craigslist to Freight: How Ryan Nolan went from valeting cars and bartending to building a 16-year career in freight brokerage. • W-2 to Agent: Why Ryan spent years believing in the traditional W-2 brokerage model before eventually becoming an independent freight agent himself. • The One-Man $100M Agency: Why Ryan believes advancing technology could eventually allow a single person to build an incredibly large freight operation. • AI Is Changing the Economics of Freight: How automation can handle more of the operational work surrounding customer relationships, rate negotiations and load building. • Relationships Still Matter: Why AI may make freight operations more efficient, but cannot replace the value of owning and strengthening customer relationships. • Always Be Building: Why relying too heavily on existing customers can be dangerous—and why freight professionals should continually develop their pipeline. • Push vs. Pull Sales: How LinkedIn, personal branding and authentic content can help freight brokers attract opportunities instead of constantly chasing them. • Stay in Your Lane: Why specialization and understanding your strengths can be more valuable than competing in highly commoditized freight markets. • The Right Way to Recruit Agents: Why aggressive, pushy recruiting can damage your reputation and why authenticity and genuine relationships create stronger long-term results. • Don't Trust a Handshake: Ryan shares an important lesson about business partnerships and why entrepreneurs should invest in properly reviewed contracts. • Authenticity + Self-Development: Why being yourself doesn't mean staying the same—and how leaning into your strengths while continuously improving can create long-term success. • Perseverance Is Underrated: Ryan's advice for younger professionals on grit, gratitude, empathy and continuing to move forward through difficult times. Next Week on Freight Agent Insider 🎧 Available now on Spotify, Apple Podcasts, YouTube & all major podcast platforms. 🔔 Follow Freight Agent Insider for weekly conversations with freight agents, brokerage owners, recruiters, entrepreneurs, and industry leaders covering freight brokerage, logistics, AI, freight technology, sales, leadership, entrepreneurship, recruiting and business growth. #freight #logistics #freightbroker #freightagent #freightagentinsider #ryannolan #flowstate #resolvelogistics #freighttech #AI #artificialintelligence #leadgeneration #sales #entrepreneurship #leadership #personalbranding #remotework #supplychain

  4. Oct 5

    Episode 58: Lauren Sharpe - The Secret to Closing 8-Figure Freight Agencies | Freight Agent Insider

    This week on Freight Agent Insider, host Levi Van Pay sat down with Lauren Sharpe, Freight Agent Recruiter at HD Ships, for an insightful and entertaining deep dive into the world of agent recruitment, overcoming industry gatekeeping and scaling multi-million dollar freight accounts! Lauren breaks down her transition from corporate W-2 recruitment into agent sourcing, sharing how she overcame imposter syndrome to close $10M+ agency accounts without a traditional freight brokerage background. Lauren pulls back the curtain on what actually works in agent recruiting—from ditching transactional "pitch slaps" on LinkedIn to building long-game trust, leveraging peer alliances with competitors and navigating remote work autonomy. She and Levi address common industry misconceptions, including the myth that agent programs are network marketing schemes and why in-house recruiters provide far greater long-term alignment than third-party agencies. Whether you're a freight agent, aspiring recruiter, or brokerage leader, this episode offers practical insights on relationships, personal branding and career growth.  🔥 KEY TAKEAWAYS:  • From Corporate to Agent Sourcing: How Lauren transitioned from W-2 corporate recruiting to high-stakes agent recruitment at HD Ships.  • Closing Enterprise Accounts: Strategies behind landing a $10M+ freight agency without a prior background in moving loads.  • Overcoming Gatekeeping & Imposter Syndrome: Why relationship-building, transparency and continuous learning beat textbook operational experience.  • Playing the Long Game: Replacing upfront "pitch slapping" with authentic introductions, patient follow-ups and relationship equity.  • In-House vs. Third-Party Recruiting: Why in-house recruiters offer true alignment and long-term support compared to commission-driven external agencies.  • Ditching Traditional KPIs: How outcome-based autonomy and flexibility drive top-tier performance in remote recruiting.  • The Power of Competitor Alliances: Collaborating with competing recruiters to share insights, candidate referrals and industry best practices.  ⏱️ IMPORTANT MOMENTS:  00:00 – Intro & Freight Agent Expo Announcement (FAX27) 02:27 – Welcome Lauren Sharpe: Nicknames & TIA Phoenix Recap  03:37 – Lauren’s Background: Transitioning from W-2 Sourcing to Agent Recruiting  05:17 – Friendships & Competitor Dynamic: Levi’s Playful Attempt to "Hire" Matt Dahl  06:03 – Why Competitors Help Each Other: Industry Alliances vs. Survivor Strategy  08:19 – Social Proof & Sourcing Styles: Building Exposure on LinkedIn vs. Cold Outreach  10:43 – Landing a $10M+ Agency: Trial, Error and Ditching the Pitch Slap  12:25 – The Female Perspective in Sales: Navigating Outreach & Building Clean Relationships  14:41 – Do You Need Freight Brokering Experience to Succeed in Agent Sourcing?  18:11 – The HD Ships Advantage: Tech Infrastructure, Back-Office & Leadership Alignment  20:20 – The Referral Loop: How Time and Agent Support Generate Inbound Growth  23:14 – Addressing Outside Misconceptions: "Is Freight Agent Recruiting a Pyramid Scheme?"  24:57 – The State of the Freight Market & Why Owner-Led Recruiting Fails  27:03 – In-House Recruiters vs. Third-Party Brokers: Accountability & Long-Term Fit  29:47 – Remote Work Autonomy: Moving Beyond Corporate KPIs & 8-to-5 Clock-Ins  33:33 – Advice for Gen-Z & Young Professionals Breaking Into Logistics  36:14 – Navigating the Early-Career Runway & Advice for Junior Recruiters  37:54 – Outro & Closing Thoughts 🎧 Available now on Spotify, Apple Podcasts, YouTube & all major podcast platforms. 🔔  Follow for weekly conversations on freight brokerage, logistics, leadership, sales, entrepreneurship, freight technology and business growth. #freight #logistics #freightbroker #freightagent #freightagentinsider #laurensharpe #hdships #agentrecruiting #freighttech #leadership #entrepreneurship #sales #supplychain #remotework

  5. Sep 28

    Episode 57: Mia Mazal- Building a 200+ Person Logistics Staffing Powerhouse | Freight Agent Insider

    This week on Freight Agent Insider, Levi Van Pay sat down with Mia Mazal, co-owner and founder of Talento, bringing her high-energy perspective on near-shoring, scaling back-office operations and breaking down barriers as a young leader! In this engaging and insightful conversation, Mia shares her journey from Delaware to Miami, navigating a male-gatekept industry and building a near-shore team of over 200 people. Mia pulls back the curtain on when freight agents should near-shore versus hire in-office, detailing how specialized overseas talent can handle complex roles like drayage, LTL and engineering. She addresses common agent hesitation—from tech infrastructure readiness to English proficiency and accents—and breaks down how human talent and AI will integrate to handle operational escalations. Additionally, Mia discusses overcoming imposter syndrome, standing up to industry stereotypes and why an abundance mindset and strong alliances are key to long-term success. Whether you're a freight agent looking to delegate operations, a brokerage leader evaluating offshore talent or a young entrepreneur navigating a gatekept industry, this episode is packed with practical strategies on staffing, team culture and business growth. 🔥 KEY TAKEAWAYS:  • The Delaware to Miami Journey: How Mia transitioned into logistics and co-founded a 200+ person company.  • Near-Shoring vs. In-Office Hiring: Key frameworks for freight agents deciding when and how to delegate operations.  • Prerequisites for Overseas Staffing: Why tech infrastructure like VPNs, domain emails and telecom systems must come first.  • Specialized Freight Knowledge: Vetting near-shore talent for nuanced roles across LTL, FTL, drayage and TMS engineering.  • Overcoming Industry Gatekeeping: How Mia built confidence, stood up to age/gender bias and earned respect in freight.  • The Power of "Conference Uncles": Leveraging strong industry allies and mentors to build authority and trust.  • AI Integration vs. Human Action: How AI agents will handle entry-level tracking while human operators manage high-level escalations. • Vetting Language & Culture: Assessing written, verbal and listening English proficiency beyond paper certifications. • Identifying Hiring Red Flags: Spotting poor attitudes and job-hoppers early to build a low-turnover remote culture. ⏱️ IMPORTANT MOMENTS:  00:00 – Intro & Freight Agent Expo Announcement (FAX27) 02:21 – Welcome Mia Mazal: Pronunciations & Miami Life  04:33 – From Delaware to Colombia: Mia’s Path to Founding Talento  06:54 – What Is Talento? Niche Staffing & HR for Logistics  08:11 – Learning Freight from Scratch: Hallway Conversations & Curiosity 11:22 – Abundance Mindset: Why Competitors & Shippers Are Potential Mentors  12:01 – Beyond Back-Office: Near-Shoring TMS Engineers & Carrier Roles 14:26 – Male-Dominated vs. Male-Gatekept: Standing Up to Industry Bias 16:08 – Building "Conference Uncles": The Importance of Industry Allies 18:11 – Near-Shoring Panel Preview & When Agents Should Hire  20:02 – Evaluating Overseas Staffing: Tech Infrastructure & Career Paths  23:30 – Addressing Language Barriers, Accents and Vetting Standards  25:21 – Is AI a Threat? Integrating Automation with Human Operations  28:01 – Voice Cloning, Accent Removers and Building Genuine Trust  29:55 – Red Flags in Hiring: Spotting Wrong Motivators & Job Hoppers  31:35 – Closing Advice for Young Entrepreneurs: Finding Passion & Taking Risks  33:33 – Outro & Closing Thoughts 🎧 Available now on Spotify, Apple Podcasts, YouTube & all major podcast platforms. 🔔 Subscribe for weekly conversations on freight brokerage, logistics, leadership, sales, entrepreneurship, freight technology and business growth. #freight #logistics #freightbroker #freightagent #freightagentinsider #miamazal #talento #nearshoring #freighttech #leadership #entrepreneurship #sales #supplychain #remotework

  6. Sep 21

    Episode 56: Zach Davis Pt 3- Pitching Logistics Managers To Land Customers | Freight Agent Insider

    This week on Freight Agent Insider, Levi Van Pay sat down with "Big Sassy" Zach Davis, high-margin freight agent and multi-six-figure profit producer, making his 3rd appearance on the show! In this raw, transparent and insight-packed conversation, Zach shares his journey of relentless hard work, protecting his time to scale and doing whatever it takes to out-execute the competition in enterprise freight. Zach pulls back the curtain on winning and retaining high-volume outbound shippers, breaking down how custom-built SOPs and deep industry preparation can win over 40-year logistics veterans. He breaks down his strategy for targeting Walmart suppliers by mastering On-Time In-Full (OTIF) fine structures, reveals how to disqualify bad prospects early and shares why authentic personality beats generic sales scripts every time. Additionally, Zach dives into using AI to buy back operational time, modernizing agent recruiting tactics and navigating industry legal shifts like nuclear verdicts. Whether you're a freight broker, agent, recruiter or logistics entrepreneur looking to master high-margin enterprise accounts, leverage operational tech or build long-term client trust, this episode is packed with tactical advice on execution, sales mindset and time management. 🔥 KEY TAKEAWAYS:  • The 3-Time Guest Perspective: Zach returns to share what’s changed, how he's scaling and why protecting his time is critical. • The SOP Strategy: How creating a custom operational SOP in his back pocket landed a major enterprise shipper.  • Protecting Your Time: Learning to manage relationships and protect your schedule to scale a multi-six-figure agency.  • Mastering OTIF & Walmart Metrics: Aligning sales pitches with shipper bonus structures and late-fee fine structures.  • Re-Engaging Lost Accounts: The exact blueprint Zach used to land a high-volume outbound account twice after leadership changes.  • Disqualifying Bad Prospects Early: Asking the right questions up front to save time and focus on high-margin fits.  • Rethinking Agent Recruiting: Why traditional "pitch slapping" fails and how recruiters can actually get an elite agent's attention.  • Leveraging Operational AI: Using automation and back-end systems to buy back time for high-touch relationship building.  • Navigating Legal Risks: How elite agents view broker liability, C.H. Robinson rulings and nuclear verdicts. ⏱️ IMPORTANT MOMENTS:  00:00 – Intro & Freight Agent Expo Announcement (FAX27)  01:38 – Welcome 3-Time Guest Zach Davis: Protecting Time & Staying Locked In  02:49 – Teamwork with Drew Bertner: Sun-Up to Sun-Down Execution 03:54 – The Best Beard in Freight & Adding Wisdom Through Gray Hair  05:51 – The Low Bar in Freight: Why Extra Effort Out-Executes Competitors  06:45 – What Recruiters Get Wrong: How to Stand Out to Top-Producing Agents  11:42 – Modernizing Sales: Why Legacy Cold Calling Is Failing in 2026  15:16 – Winning a Major Shipper Twice: The Back-Pocket SOP Strategy  18:12 – Pitching Enterprise Shippers: Leveraging OTIF Fines & Bonus Metrics 21:10 – Live Mileage Challenge with Ryan Nolan  26:17 – Sales Advice for Junior Agents: Disqualifying Poor Fits Fast  27:04 – Operations Tech & AI: Buying Back Time for High-Touch Relationships  28:29 – Nuclear Verdicts & Legal Frameworks: Navigating Industry Risks  30:20 – Outro & Closing Thoughts 🎧 Available now on Spotify, Apple Podcasts, YouTube & all major podcast platforms. 🔔 Subscribe for weekly conversations on freight brokerage, logistics, leadership, sales, entrepreneurship, freight technology and business growth. #freight #logistics #freightbroker #freightagent #freightagentinsider #zachdavis #bigsassy #freighttech #leadership #entrepreneurship #sales #supplychain #otif #enterprisefreight

  7. Sep 14

    Episode 55: Dushawn Falls- From OTR Driver to Multi-Six-Figure Freight Agent | Freight Agent Insider

    This week on Freight Agent Insider, Levi Van Pay sat down with Dushawn Falls, former OTR truck driver turned high-margin freight broker agent at Trinity Logistics and founder of Tenacity Express. In this raw, transparent and insight-packed conversation, Dushawn shares his journey from driving 14-hour days behind the wheel to starting his own trucking company, transitioning into brokerage and scaling an elite heavy haul business. Dushawn pulls back the curtain on the complex world of heavy haul and building materials, breaking down why specialized freight requires trust, precision and deep carrier relationships. He reveals his secret to winning high-value shippers through in-person prospecting and the "People Lottery," explains how a chance conversation in a gym sauna led to his first massive crane project and shares how 3 AM motivational audio fueled his transition from manual labor to mental grit. Additionally, Dushawn breaks down why human reasoning beats over-hyped tech, how to navigate 40-load crane operations and why integrity and reputation are everything in logistics. Whether you're a truck driver looking to change your career, a freight agent wanting to master high-margin niches or an entrepreneur looking to scale through face-to-face sales, this episode is packed with tactical advice on execution, mindset and long-term success. 🔥 KEY TAKEAWAYS: The Driver-to-Agent Blueprint: How Dushawn translated a decade of behind-the-wheel OTR experience into a thriving freight agency. The "People Lottery" Strategy: Why being curious, getting out of the office and striking up casual conversations wins massive shippers. Mastering Crane & Heavy Haul Projects: Coordinating 40-load site projects, multi-state axle sourcing and tight delivery timelines. Ditching Cold Calls for In-Person Prospecting: Shortening sales cycles by shaking hands, visiting job sites and building real rapport. The Sauna Opportunity: The true story of under-quoting his first heavy haul job and turning a single chance encounter into a lifelong client. Human Reasoning Over Tech Hype: Why relationship-driven brokerages out-execute automated software in complex logistics. 3 AM Discipline & Mindset: How daily self-improvement, Eric Thomas audio and sales books helped Dushawn rewire his career trajectory. Building Tenacity Express: Creating a brand centered on precision, execution and an unshakeable reputation in logistics. ⏱️ IMPORTANT MOMENTS: 00:00 – Intro & Freight Agent Expo Announcement (FAX27) 01:39 – Welcome Dushawn Falls: Background & Early Days Driving for CR England & Ryder 03:11 – The Transition: From Truck Ownership to Brokerage & Trinity Logistics 06:13 – Leaving 14-Hour Driving Shifts to Prioritize Family & Health 08:25 – Moving Beyond Reefer: Finding a Niche in Building Materials & Crane Freight 09:55 – The Operational Nightmare: Coordinating 40-Load Crane Movements 13:09 – The Sauna Story: How a Casual Gym Conversation Started a Heavy Haul Career 16:47 – The "People Lottery": Using Curiosity as Your Ultimate Sales Superpower 19:41 – Why In-Person Visits Beat Cold Calls to Close Shippers Faster 22:02 – Maintaining Deep Account Relationships Without Expensive Dinners 27:32 – From Blue-Collar Labor to Mental Grit: Rewiring Your Mindset with Sales & Audiobooks 33:26 – Mentorship & Final Advice: Be Your Own Spokesperson and Talk to People 35:25 – Outro & Closing Thoughts 🎧 Available now on Spotify, Apple Podcasts, YouTube & all major podcast platforms. 🔔 Subscribe for weekly conversations on freight brokerage, logistics, leadership, sales, entrepreneurship, freight technology and business growth. #freight #logistics #freightbroker #freightagent #freightagentinsider #dushawnfalls #heavyhaul #trucking #tenacityexpress #freighttech #leadership #entrepreneurship #sales

  8. Sep 7

    Episode 54: Patrick Gray- Mastering Heavy, Open-Deck, and Oversized Freight | Freight Agent Insider

    This week on Freight Agent Insider, Levi Van Pay sat down with Patrick Gray, founder and leader in open-deck heavy haul logistics. In this raw, transparent and insight-packed conversation, Patrick shares his journey from managing restaurants to transitioning into B2B freight sales, building a team generating $200K–$250K in monthly margin and ultimately taking the leap on Valentine’s Day eve to build his own thriving brokerage business. Patrick pulls back the curtain on the gatekept world of heavy haul logistics and why specialized freight requires an entirely different operational playbook. He breaks down how applying restaurant-style hospitality anticipating customer needs and "annoying" shippers with proactive updates, built the foundation for his success. Additionally, Patrick reveals why he built Freight Deck, an in-house heavy haul software designed to turn 5-hour quoting and permitting workflows into 5-minute tasks and delivers a masterclass on how recruiters fail when pitching high-producing freight agents. Whether you're a freight broker, agent or logistics entrepreneur looking to master high-margin niches, leverage proprietary tech or scale carrier relationships, this episode is packed with tactical advice on execution, leadership and long-term reputation. 🔥 KEY TAKEAWAYS: The Hospitality Playbook: How Patrick translated restaurant service principles into high-touch freight management. Leaving the Agency Trap: Taking the ultimate entrepreneurial leap to build an independent book of business. Unlocking Heavy Haul: Navigating the steep learning curve, specialized equipment and line-haul pricing in open-deck freight. The "Annoy Them with Updates" Method: Differentiating your brokerage by over-communicating loaded statuses, PODs and transit updates. In-House Tech Superweapons: Why Patrick created Freight Deck to automate complex heavy haul calculations, permits and escort costs in minutes. The Truth About Recruiting Top Agents: Why 70% splits and basic back-office pitches fail to move the needle for elite producers. Surviving Heavy Haul Horror Stories: Managing dimensional accuracy, mountain transit load shifts and eating claims out-of-pocket to protect key accounts. Unshakable Reputation: Patrick's core philosophy on why honesty and integrity are the only long-term currency in logistics. ⏱️ IMPORTANT MOMENTS: 00:00 – Intro & Freight Agent Expo Announcement (FAX27) 01:35 – Welcome Patrick Gray: From Restaurant Service Manager to Sales 03:41 – Building a $250K/Month Margin Book & Quitting on Valentine’s Day Eve 06:45 – Finding the Niche: Transitioning into Open-Deck & Heavy Haul Freight 08:20 – Demystifying Heavy Haul: Overcoming a Gatekept Segment of Logistics 09:50 – Proactive Communication: The "Annoy Your Customer with Updates" Rule 13:55 – Introducing Freight Deck: Turning 5-Hour Workflows into 5-Minute Tasks 16:11 – Human Reasoning vs. Automation: Tech That Multiplies Broker Efficiency 20:30 – Carrier Vetting & High-Touch Safety Operations in Heavy Haul 23:00 – Permits, Escorts & Route Planning Demystified 25:35 – Pitching Elite Agents: What Recruiters Get Wrong About High Producers 29:30 – Heavy Haul Claims & Fraud Prevention: Protecting Shippers at All Costs 33:04 – Final Blueprint: Building an Unshakeable Reputation in Freight 33:42 – Outro & Closing Thoughts 🎧 Available now on Spotify, Apple Podcasts, YouTube & all major podcast platforms. 🔔 Subscribe for weekly conversations on freight brokerage, logistics, leadership, sales, entrepreneurship, freight technology and business growth. #freight #logistics #freightbroker #freightagent #freightagentinsider #patrickgray #heavyhaul #flatbedlogistics #freightdeck #freighttech #leadership #entrepreneurship

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About

The Freight Agent Insider Podcast is hosted by Levi Van Pay, a social media personality and Director of an agent based brokerage delivering weekly insights and stories, featuring the best freight agents in the industry. Made for aspiring and experienced freight agents alike, each weekly 30 minute episode tackles one key topic— from breaking into the industry to mastering negotiations— with practical tips, real-world stories, and actionable advice. Subscribe for insider knowledge!

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