Last2First Podcast

Jason Burns

Welcome to Last 2 First, the podcast dedicated to exploring the final mile in logistics and the unique challenges faced by business owners in this vital industry. Each episode features insightful conversations with industry experts, entrepreneurs, and thought leaders who share their experiences, strategies, and innovations shaping the future of final mile delivery. Join us as we dive into topics like optimizing delivery routes, enhancing customer satisfaction, navigating regulatory hurdles, and leveraging technology for efficiency. Whether you're a seasoned logistics professional or a business owner looking to improve your operations, Last 2 First offers valuable insights and actionable advice to help you lead your business to success. Tune in and discover how to turn the last mile into your first priority!

  1. The IC Legal Trap That Can Kill Your Delivery Business

    11h ago

    The IC Legal Trap That Can Kill Your Delivery Business

    Most final mile operators think their IC contracts protect them. They do not.Transportation lawyer Doug Grawe breaks down what actually keeps your business safe and what quietly puts it at risk. TIMESTAMPS00:00 - Intro and Welcome03:45 - Doug's Path Into Transportation Law09:30 - No Single IC Definition17:00 - How TPAs Actually Work25:00 - Government Audits: What to Do34:30 - Arbitration and the Supreme Court44:00 - Lease-to-Purchase Programs52:00 - Uniforms and Control Issues58:30 - Two Things That Protect You Most1:02:00 - Where to Find Doug Doug Grawe is the founder and CEO of The Grawe Group, a legal and consulting firm focused on the transportation industry. With 15 years as in-house general counsel for a major trucking company, Doug now works with carriers, DSPs, and final mile operators to protect their independent contractor programs from misclassification claims, government audits, and legal exposure. In this episode, Jason and Doug cover the full landscape of IC legal risk in final mile delivery, from the basics of classification tests to Supreme Court cases currently in progress. Key takeaways:There are up to five different definitions of "independent contractor" per state, varying by agencyTPAs are a powerful tool, but only if you actively use them to build proofGovernment inquiries, even small ones, should go to a designated person immediatelyLease-to-purchase programs carry hidden legal risk if the economics do not hold upThe two things that reduce your legal risk more than anything: treat people well and pay them fairly Connect with Doug at thegrawegroup.com. Listen to The Grawe Pod for more expert content on transportation law, finance, and operations. 📌 Shoutout to our Sponsors!Dropoff Inc.https://www.dropoff.com/info@dropoff.com+1 888-376-7633 GigSafehttps://www.gigsafe.com/+1 407-496-9882 Deliver Differenthttps://deliverdifferent.com/ SCIhttps://sciadmin.com/ CXThttps://cxtsoftware.com/

    1h 2m
  2. From $2,500 in the Bank to $250M in Revenue: Matt Silverberg’s Last Mile Playbook

    May 26

    From $2,500 in the Bank to $250M in Revenue: Matt Silverberg’s Last Mile Playbook

    Matt Silverberg walked into a failing $10M courier company with six months of runway, $100,000 in monthly losses, and zero logistics experience. He walked out years later as CCO of a $250M global healthcare logistics powerhouse. This episode is the full story. In this conversation, Matt takes us from his days as a clinical psychology student covering radiopharmaceutical routes at night to building one of the most recognized brands in last-mile healthcare logistics. He breaks down the M&A strategy that took Associated Couriers from $30M to $100M in two years, what it really costs to over-promote loyal employees, and why he believes most business owners leave serious money on the table when they exit. Episode highlights:• The $2,500 payroll crisis: how Matt handled $350,000 in payroll due with almost nothing in the bank • Special Permit 8308: the rare certification only 3 companies in the US hold and why it matters for the radiopharmaceutical market • The M&A playbook: how Matt structured rapid acquisitions across the US and Europe • Exit planning: what buyers look for and how to position for a premium valuation years in advance • Why loyal employees can become your biggest operational liability if you are not paying attention If you are building a courier or logistics company and thinking about what comes next, this episode is required listening. Connect with Matt and explore exit strategy support at the L2F Huddle: l2fhuddle.com 📌 Shoutout to our Sponsors!Dropoff Inc.https://www.dropoff.com/info@dropoff.com+1 888-376-7633 GigSafehttps://www.gigsafe.com/+1 407-496-9882 Deliver Differenthttps://deliverdifferent.com/ SCIhttps://sciadmin.com/ CXThttps://cxtsoftware.com/

    1h 14m
  3. Michael Frankel: Why Most Entrepreneurs Get This Completely Wrong

    May 19

    Michael Frankel: Why Most Entrepreneurs Get This Completely Wrong

    What does it take to grow a family-run logistics business from just a handful of drivers to nearly 2,000 across the U.S. and Canada? In this episode of Last2First, Jason Burns sits down with Michael Frankel, President of Sir Lancelot Courier & Delivery and COO of PDX, for a conversation packed with real operator insights, lessons learned, and plenty of laughs. Michael shares his journey from working in nursing home administration (yes, really 😅) to helping build one of the most respected delivery operations in the industry. In this episode:✅ How PDX scaled from 6 drivers to nearly 2,000✅ The power of customer service in building long-term growth✅ Dedicated driver models vs. on-demand delivery✅ How technology and automation are changing logistics✅ Why final mile operators should rethink insurance and risk management✅ Captive insurance explained in plain English✅ The future of robotics, AI, and delivery automation✅ How family businesses can compete in a changing industry This episode is equal parts strategy, storytelling, and straight-up operator talk. If you're in logistics, final mile, courier, transportation, or supply chain—this one is for you. Subscribe for more conversations with the leaders moving this industry from LAST to FIRST. #Last2First #Logistics #FinalMile #SupplyChain #Transportation #entrepreneurship  📌 Shoutout to our Sponsors!Dropoff Inc.https://www.dropoff.com/info@dropoff.com+1 888-376-7633 GigSafehttps://www.gigsafe.com/+1 407-496-9882 Deliver Differenthttps://deliverdifferent.com/ SCIhttps://sciadmin.com/ CXThttps://cxtsoftware.com/

    1h 3m
  4. 65 Years, 3 Generations & One Accident That Changed Everything

    May 12

    65 Years, 3 Generations & One Accident That Changed Everything

    65 years. Three generations. One leader's turn to modernize or get left behind. In this episode of Last of First Podcast, Jason Burns sits down with David Hardy, President & CEO of Bonnie Speed Logistics, one of the longest-running courier companies in Ohio, founded in Cleveland in 1959. David's path was anything but straight. Hampton University. Purdue chicken processing lines. New Jersey food manufacturing. Then home — to take over a legacy business that needed a new culture, new systems, and a bold new vision. We get into:Taking over a 65-year family business and rebuilding the culture from scratchOutsourcing night dispatch AND accounting — what changed immediatelyBuilding Cleveland's first DC Level 3 EV fast charging station as a new revenue streamThe 2016 accident that rewrote his entire approach to risk & complianceWhy routes beat on-demand every time for margin and predictabilityThe medical linen vertical nobody else in the last mile is talking aboutA real conversation about legacy, leadership, and what it takes to drag a family business into the future. 👉 Subscribe for real last-mile logistics strategy and courier business growth insights👉 Comment "LEGACY" if you're building or running a family business👉 Comment "ROUTES" if predictable margin is your focus right now 📌 Shoutout to our Sponsors!Dropoff Inc.https://www.dropoff.com/info@dropoff.com+1 888-376-7633 GigSafehttps://www.gigsafe.com/+1 407-496-9882 Deliver Differenthttps://deliverdifferent.com/ SCIhttps://sciadmin.com/ CXThttps://cxtsoftware.com/ last mile logistics, courier business, logistics entrepreneur, family business, delivery service business how to grow a courier company, medical courier business, last mile delivery margins, outsourcing dispatch, logistics route vs on demand, how to run a family logistics business entrepreneurship podcast, family business legacy, third generation business owner, founder stories, CEO mindset, Black owned business EV charging stations logistics, medical linen delivery, Bonnie Speed Logistics, Cleveland courier company, outsourcing night dispatch, logistics compliance risk, nuclear verdicts trucking, last mile route business

    1h 8m
  5. From Miami Courier to 13,500 Members: The Steve Howard Story

    May 5

    From Miami Courier to 13,500 Members: The Steve Howard Story

    33 years. One partner who went bankrupt. Millions left on the table. And zero regrets. In this episode of Last of First Podcast, Jason Burns sits down with Steve Howard — 2026 CLDA Hall of Fame inductee, former owner of Esquire Express in Miami, and current Director of eCommerce Solutions at WCA, the world's largest freight forwarder network with 13,500 members across 197 countries. Steve built his courier business from scratch at 23 years old with nothing to lose — legal courier work, medical runs during Hurricane Andrew, air cartage, big & bulky e-commerce — and watched margins get gutted by three PLs, commoditization and Chinese-backed competitors willing to lose money just to grab market share. He's seen it all. And he's not holding back. We get into:✅Why he walked away from a 33-year business and never looked back✅How Hurricane Andrew turned a cargo van into his biggest account overnight✅The three PL model that squeezed his margins from 24% down to 4%✅What Chinese-backed delivery companies are doing to last mile pricing right now✅Why volume without value will eventually destroy your business✅How WCA connects last mile carriers directly to freight forwarders — and why the margin difference is massive✅The partner who went bankrupt and left him holding millions in SBA loans✅A masterclass in survival, reinvention and knowing exactly when to walk away. 👉 Subscribe for real last mile logistics strategy and courier business growth insights👉 Comment "MARGINS" if the race to the bottom is hitting your business right now👉 Comment "WCA" if you want to learn more about unlocking international freight opportunities CHAPTER MARKERS00:00 - Introduction & CLDA Hall of Fame Moment03:30 - His Dad Surprises Him at the Ceremony07:00 - What Is WCA? 13,500 Members, 197 Countries12:00 - World Parcel Alliance: Cutting Out the Brokers18:30 - Starting Esquire Express at 23 in Miami24:00 - Hurricane Andrew and the Diesel Run to South Miami Hospital29:30 - First eCommerce Client: IKEA in 199934:00 - How 3PLs Crushed Final-Mile Margins40:30 - Chinese Competitors Charging $2.20 Per Delivery46:00 - The Business Partner Collapse That Cost Him Everything54:00 - Why He Finally Sold Esquire Express After 33 Years60:30 - Every Account Must Stand on Its Own65:00 - His "Last to First" Moment 📌 Shoutout to our Sponsors!Dropoff Inc.https://www.dropoff.com/info@dropoff.com+1 888-376-7633 GigSafehttps://www.gigsafe.com/+1 407-496-9882 Deliver Differenthttps://deliverdifferent.com/ SCIhttps://sciadmin.com/ CXThttps://cxtsoftware.com/ Primarylast mile logistics, courier business, logistics entrepreneur, delivery service business, freight forwarder network High-Intent Searchhow to sell a logistics business, last mile delivery margins, courier business exit strategy, freight forwarder last mile, WCA logistics network, how to grow a courier company, logistics gross margin benchmarks Discovery / Viralentrepreneurship podcast, business exit story, founder stories, CEO mindset, how I built this, logistics Hall of Fame, built from scratch Episode-Specificrace to the bottom logistics, three PL margin squeeze, Chinese delivery companies US market, CLDA Hall of Fame, WCA World Cargo Alliance, Hurricane Andrew Miami, air cartage logistics, SBA loan business failure

    56 min
  6. She Left Wall Street & Built a Medical Courier Empire

    Apr 21

    She Left Wall Street & Built a Medical Courier Empire

    What if you could build a profitable business from scratch—without experience, tech skills, or a huge investment? In this episode, Rebecca Massicotte, founder of Red Fox Medical Courier, shares how she went from Wall Street burnout to building a multi-city healthcare logistics company—serving critical patient care operations across the U.S. You’ll discover: How she started with just a website and one clientThe truth about the medical courier industry (and why it’s booming)How she scaled to 25+ cities and 100+ driversThe mindset shift that took her from “delivery service” to patient care businessHidden opportunities in last-mile logistics most people overlookThis isn’t just a business story—it’s a masterclass in thinking bigger, moving faster, and building something that actually matters. 👉 Whether you're an entrepreneur, looking for a new income stream, or curious about the logistics industry… this episode will open your eyes. KEYWORDS Primary last mile logistics, medical courier business, courier company, delivery service business, logistics entrepreneur, healthcare logistics High-Intent Search how to start a medical courier business, how to scale a courier company, courier business tips, logistics company growth strategy, how to grow a delivery business, operations management small business Discovery / Viral entrepreneurship podcast, business success stories, founder stories, startup to scale, CEO mindset, real business talk, woman entrepreneur, Wall Street to entrepreneur

    1h 4m
5
out of 5
9 Ratings

About

Welcome to Last 2 First, the podcast dedicated to exploring the final mile in logistics and the unique challenges faced by business owners in this vital industry. Each episode features insightful conversations with industry experts, entrepreneurs, and thought leaders who share their experiences, strategies, and innovations shaping the future of final mile delivery. Join us as we dive into topics like optimizing delivery routes, enhancing customer satisfaction, navigating regulatory hurdles, and leveraging technology for efficiency. Whether you're a seasoned logistics professional or a business owner looking to improve your operations, Last 2 First offers valuable insights and actionable advice to help you lead your business to success. Tune in and discover how to turn the last mile into your first priority!

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