This Side Up - Logistics Tech & Design

Andrew Verboncouer, Intermode
  • 5.0 (1)
  • Technology
  • Updated Monthly

Welcome to This Side Up, the podcast about logistics tech and design. From robots and AI to cutting-edge SaaS and game-changing services, we’ll explore the big ideas—and brilliant minds—reshaping how the world moves through supply chain innovation.

Episodes

  1. Jul 28

    Turning Empty Backhauls Into a New Source of Freight Capacity with Russ Jones

    “Those trucks are empty 80% of the time on their backhauls. This is a huge waste. We’re talking about $150 billion domestically in wasted capacity.” In this episode, Russell Jones, CEO and co-founder of Private Fleet Net Zero, discusses the massive inefficiency hiding within the freight market and how his experience across startups, freight brokerage, digital matching, and private fleets led him to build a solution. Russ explains why nearly half of all trucks belong to private or dedicated fleets, yet many return empty, creating an enormous source of untapped capacity. Russ also shares how Private Fleet Net Zero precisely matches private fleet backhauls with freight buyers, helping fleets generate revenue while giving shippers access to reliable capacity at a lower cost. He explores the importance of founder-market fit, listening closely to early customers, and using proprietary data and AI to structure information, improve matching, and create efficiencies that are difficult to replicate. Tune in to learn: Why private fleet trucks return empty so often How precise freight matching can unlock underused capacity The role of proprietary data and AI in improving freight networks Jump into the conversation: (00:00) Introduction (01:11) Russ Jones’s journey across four startups (03:37) Finding large markets with clear needs (04:52) Discovering a $150 billion capacity opportunity (05:32) Validating the idea before building the MVP (06:36) Why Russ keeps returning to startups (07:49) Recruiting 60 fleets in the first year (08:24) Why private fleet backhauls remain empty (10:44) Unlocking capacity within the existing freight market (13:33) How experience created strong founder-market fit (16:02) Applying AI to proprietary freight data (17:37) Why ELD data remains largely hidden (19:25) How better incentives improve fleet safety (21:37) The future of private fleet capacity (24:32) Who Private Fleet Net Zero serves (25:43) Turning industry experience into founder advantage Connect Check out Private Fleet Net Zero: https://privatefleetnz.com/ Connect with Russell Jones: https://www.linkedin.com/in/russellkjones/ Show InformationThis Side Up Podcast digs deep into the minds of founders, builders, and operators reshaping the future of commerce and logistics. Subscribe for more conversations with industry leaders who are actually building the future. Podcast Website: https://www.thissideup.fm/ Produced by: Intermode - https://www.intermode.is/ Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

    Turning Empty Backhauls Into a New Source of Freight Capacity with Russ Jones

  2. May 14

    Why Freight Invoicing Is Broken and How AI Fixes It with Charley Dehoney of Upwell

    “Seeing  large trucking companies and even barge businesses struggling with the same mechanics on the billing and invoicing side, that's when I knew that there was a business to be built." In this episode, Charley Dehoney, CEO and co-founder of Upwell, discusses his extensive background in transportation logistics and how he identified critical challenges in the industry that led to the creation of Upwell. Charley reflects on his journey from door-to-door sales in logistics to building and scaling multiple logistics companies. He highlights how his experience with the complexities of billing and invoicing, particularly in large transportation businesses like steamship lines and trucking companies, sparked his conviction to address these issues through Upwell. Charley also shares insights into how Upwell is using AI to streamline payments and improve efficiency in the logistics industry. He emphasizes the importance of eliminating inefficiencies in the payment process and the challenges of getting accurate invoices out the door, from documentation errors to missing information. As he continues to grow Upwell, Charley is focused on helping carriers scale without expanding their back office, leveraging AI to automate complex workflows, reduce errors, and improve payment cycles. Tune in to learn: How Upwell is transforming the invoicing process in logistics The role of AI in speeding up payments and enhancing accuracy Why proper documentation and streamlined workflows are key to improving logistics payments and scalability Jump into the conversation: (00:00) Intro (02:35) Lessons from door-to-door sales experience (05:02) Football's influence on business leadership (12:24) The importance of payments in freight (14:51) From freight tech to Upwell's idea (17:45) AI revolutionizing faster invoicing processes (18:43) How Upwell works today in logistics (23:43) Shipper-level auditing and payment processes (28:42) Knowing when to leverage Upwell (30:29) Where to stay updated on Upwell Check out Upwell: https://www.upwell.com/ Connect with Charley Dehoney: https://www.linkedin.com/in/cdehoney/ Show InformationThis Side Up Podcast digs deep into the minds of founders, builders, and operators reshaping the future of commerce and logistics. Subscribe for more conversations with industry leaders who are actually building the future. Podcast Website: https://www.thissideup.fm/ Produced by: Intermode - https://www.intermode.is/ Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

    Why Freight Invoicing Is Broken and How AI Fixes It with Charley Dehoney of Upwell

  3. 12/22/2025

    $1 Billion in Freight: Inside Parade's AI Automation Engine with Anthony Sutardja

    What happens when you try to build "Uber for trucking" and realize brokers don't need replacing—they need better tools? Anthony Sutardja, CEO and co-founder of Parade, takes us through a decade-long journey from failed brokerage to $7 billion capacity management platform. This conversation goes deep on the real economics of freight brokerage: why carrier procurement eats 35% of costs ($44 per load), how 20% of carrier calls never even reach the sales floor, and why only 4 out of 100 conversations result in actual bookings. Anthony shares the data behind Parade's "Centaur model"—proving that AI + human negotiation beats either approach alone by $39 per load. We explore Co-Driver, Parade's AI system handling over 7 million conversations, the wild reality of AI-to-AI negotiations happening in freight today, and why the industry benchmark just jumped from 50 to 200 loads per week per rep. Whether you're a freight broker looking to scale, building logistics tech, or implementing AI in operations, this episode delivers battle-tested insights you won't find anywhere else. In This EpisodeWhy "Uber for trucking" failed and what Parade built insteadThe economics: $44 per load, 35% of total lifecycle costsHow 20% of carrier calls get dropped before reaching brokersThe carrier conversation funnel: 100 calls to 4 bookingsCo-Driver's AI negotiation: filtering 55% of wasted conversationsThe Centaur model: Why AI + human beats both alone ($39 proof)7 million automated conversations and countingAI-to-AI freight negotiations: The weird new reality4x productivity gains: From 50 to 200 loads per week per repAutomating $1B of the $100B annual freight brokerage marketThe path from 70% to 100% digital freight coverageWhy data freshness matters more than TMS capabilitiesBuilding carrier relationships from transactional freightThe three pillars driving rapid AI adoption in freightAbout Anthony SutardjaAnthony is CEO and co-founder of Parade, a capacity management platform with $7 billion in freight on platform. Starting a decade ago with an unsuccessful attempt at building a freight brokerage, Anthony learned firsthand that brokers don't need replacing—they need better tools. Parade now serves hundreds of brokerages, automating over 7 million conversations and handling $1 billion in fully touchless AI freight annually. Episode Timestamps00:00 - Intro 01:33 - From "Uber for Trucking" to Building Tools 04:34 - The Aha Moment: Brokers Need Better Tools 06:10 - Texting Every Carrier: Early AI Automation 08:42 - What Makes Parade Different 09:35 - The Economics: $44 Per Load 10:28 - The Phone Line Problem 13:34 - 200 Loads Per Week Per Rep 16:45 - How Co-Driver Works 20:28 - The Funnel: 100 Conversations, 4 Bookings 22:49 - Sponsor Break 24:47 - Transactional to Relationship 26:31 - The Centaur Model 27:24 - The $39 Advantage 30:40 - 7 Million Automated Conversations 31:36 - AI to AI: The New Reality 35:48 - 4x Productivity Gains 36:26 - $1 Billion Automated 37:58 - The Road to 100% Digital 41:38 - AI Fleet Case Study 44:41 - Where to Find Parade Show InformationThis Side Up Podcast digs deep into the minds of founders, builders, and operators reshaping the future of commerce and logistics. Subscribe for more conversations with industry leaders who are actually building the future. Podcast Website: https://www.thissideup.fm/ Produced by: Intermode - https://www.intermode.is/ Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

    $1 Billion in Freight: Inside Parade's AI Automation Engine with Anthony Sutardja

  4. 10/30/2025

    Open Source Freight Tech: From TMS to AI Tools with Garrett Allen, Founder of SearchCarriers

    In this episode of This Side Up, Garrett breaks down his unconventional approach to building freight tech: live streaming development, open-sourcing a complete TMS, and creating multiple micro-SaaS tools that solve real problems for brokers and carriers. Whether you're running a brokerage, building logistics software, or curious about the indie hacker approach to B2B SaaS, this conversation is packed with insights you won't find anywhere else. Key Topics Covered→ Building an open-source TMS and why freight needs it → The reality of AI in logistics: what works vs. the hype → Search Carriers: image search, fraud prevention, and the privacy debate → Why full brokerage automation is still a myth → Human-in-the-loop AI: the right way to implement automation → Building in public and live streaming freight tech development → From Lasso (AI track & trace) to Load Partner (TMS) to Search Carriers → The indie hacker approach to freight tech → Fighting freight fraud with better tools and data → Practical advice for brokerages adopting AI   About Garrett AllenGarrett is the founder of Load Partner (open-source TMS) and Search Carriers (carrier research and discovery tool). He spent 8 years at Integrity Express Logistics building the TMS that helped them scale to 500+ employees and $1B in revenue, then worked as a Senior Engineering Manager at Transfix overseeing payments and shipper operations. He's now building multiple freight tech tools as a serial entrepreneur and shares the entire development process publicly through weekly live streams. Connect with Garrett Allen https://www.linkedin.com/in/allengc/ SearchCarriers https://searchcarriers.com LoadPartner https://get.loadpartner.io/   Segments00:00 - Intro 02:27 - Launching Lasso: AI Track and Trace 03:50 - Why They Pivoted to Open Source TMS 04:30 - Building Load Partner in Public 05:22 - Creating SearchCarriers: FMCSA Data Made Easy 06:29 - The Indie Hacker Approach to Freight Tech 08:08 - Open Source TMS Traction and Use Cases 10:08 - Image Search and the Privacy Debate 13:27 - Fighting Fraud in Freight 16:02 - The Micro-SaaS Strategy 18:26 - AI in Freight: Lasso's Journey 20:11 - Why Full Brokerage Automation Won't Happen Yet 22:03 - DAT's Convoy Acquisition: What It Means 24:24 - Advice for Implementing AI in Brokerage Operations 26:05 - Building Trust: Human-in-the-Loop AI 30:20 - No-Code Tools and Empowering Operators 31:56 - What's Next in AI for Freight Show InformationThis Side Up Podcast digs deep into the minds of founders, builders, and operators reshaping the future of commerce and logistics. Subscribe for more conversations with industry leaders who are actually building the future. Podcast Website: https://www.thissideup.fm/ Produced by: Intermode - https://www.intermode.is/ Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

    Open Source Freight Tech: From TMS to AI Tools with Garrett Allen, Founder of SearchCarriers

  5. 10/06/2025

    Building AI That Augments, Not Replaces People in Logistics with Shaman Ahuja, Deputy CEO of Optym

    We explore why multi-objective optimization matters more than finding a single "right" answer, how Optym balances traditional algorithms with modern AI, and why garbage in, garbage out is still the biggest challenge in optimization. Shaman also shares hard-won lessons about organizational design, including why platform teams often fail and how Optym structures product teams around business problems instead. You'll hear about the surprising parallels between airline operations and freight, why planners with 20+ years of experience won't trust black box solutions, and how LLMs can serve as an interface layer without replacing the heavy lifting of discrete optimization models. Key Topics✦ Wall Street to freight tech: career transitions in logistics ✦ Augmentation vs. automation in AI implementation ✦ Multi-objective optimization across airlines, LTL, and truckload ✦ Why business-focused teams beat platform teams ✦ Building enterprise software with a customer-first mindset ✦ The role of LLMs alongside traditional optimization algorithms ✦ Lessons from 25 years of bootstrapped growth   Segments00:00 - Intro 01:06 - What is Optym? Transportation Optimization Explained 03:26 - Shaman's Background 05:51 - Goldman Sachs Experience: Life on Wall Street 07:59 - Business Beyond Money 09:14 - Parallels Between Finance and Logistics Optimization 11:25 - Customer Focus: From Southwest Airlines to LTL 13:33 - Time to Value: Delivering on Promises Consistently 15:28 - Complexity Across Transportation Modes 16:25 - The Faster Horse Problem: Balancing User Feedback with Innovation 18:15 - Multi-Objective Optimization: No Single "Right" Answer 21:12 - Balancing Traditional Algorithms with Modern AI 23:18 - Garbage In, Garbage Out: Data Quality Matters 25:49 - LLMs as Interface Layer, Not Replacement 26:00 - Why Black Box AI Doesn't Work 27:21 - Airline Network Planning: 9 Months Ahead Scheduling 29:05 - Matching Capacity to Demand: Airlines vs Trucks 30:28 - LTL Dock Optimization: Learning from Airlines 34:18 - U-Haul Pod Optimization Case Study 36:17 - Organizational Design: Platform Teams vs Business-Focused Teams 39:10 - The 80/20 Split: Dual Hats in Product Development 40:45 - Building With Care: Why Deep Domain Knowledge Takes Years 44:34 - 25 Years Bootstrapped: Growth Without VC Funding 46:16 - Multi-Objective Thinking: AI as Augmentation, Not Replacement 48:30 - Final Thoughts: Context, Culture, and Getting AI Right   Whether you're building technology for transportation or implementing AI in operations, this conversation offers a refreshing perspective on doing more with less—without losing the human expertise that makes it all work. Show InformationThis Side Up Podcast digs deep into the minds of founders, builders, and operators reshaping the future of commerce and logistics. Subscribe for more conversations with industry leaders who are actually building the future. Podcast Website: https://www.thissideup.fm/ Produced by: Intermode - https://www.intermode.is/ Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

    Building AI That Augments, Not Replaces People in Logistics with Shaman Ahuja, Deputy CEO of Optym

  6. 08/12/2025

    Solving the Fleet Software Adoption Problem with Eric Rodriguez, CEO of Vendorflow

    Join us for a deep dive with Eric Rodriguez, CEO of VendorFlow, who cracked the code on driver communication after watching countless fleet apps fail with 20% adoption rates. Eric shares how his team pivoted from building another driver app to creating a unified communications platform that meets drivers where they already are - SMS. In this episode of This Side Up, Eric breaks down the harsh realities of driver-facing technology, why forcing adoption never works, and how smart integrations with telematics systems like Samsara can dramatically improve safety, compliance, and productivity. If you're building for fleets, struggling with driver adoption, or curious about the future of logistics communication, this conversation is packed with hard-won insights. Key Topics Covered→ Why 80% of drivers reject fleet apps and how to solve it → The SMS-first approach that eliminates training and adoption friction → Smart routing between SMS and in-cab alerts based on driving status → Preventing safety violations through communication rules and AI camera integration → Building successful partnerships with telematics providers like Samsara → The future of RCS (SMS 2.0) in fleet operations → How to focus your target market and avoid the multi-audience trap → Structuring lean teams around direct customer feedback ✦ About Eric Rodriguez ✦Eric is the CEO of VendorFlow, a unified communications platform purpose-built for transportation. With over 12 years in venture-backed tech, Eric and his team (mostly ex-Next Trucking) learned firsthand why driver apps fail and built a solution that actually works. Segments00:00 - Intro 01:09 - From Next Trucking to VendorFlow 01:51 - The 20% Driver App Adoption Problem 03:18 - SMS-First Philosophy and Adoption Strategy 05:28 - Building Strategic Partnerships Through User Feedback 06:59 - Product Development and Customer-Driven Teams 09:44 - Target Market Focus: Fleets vs Brokers 18:26 - Episode Sponsor: Intermode 19:42 - Unified Communications Platform Overview 23:03 - Smart Message Routing and Safety Integration 26:14 - ELD Integration and Productivity Features 31:05 - The Future of RCS and Rich Communication 34:57 - What's Next for VendorFlow Show Noteshttps://www.thissideup.fm/episode/how-vendorflow-solved-driver-app-adoption Connect with EricLinkedIn: https://www.linkedin.com/in/ericrod/ Website: https://www.vendorflow.co Show InformationThis Side Up Podcast digs deep into the minds of founders, builders, and operators reshaping the future of commerce and logistics. Subscribe for more conversations with industry leaders who are actually building the future. Podcast Website: https://www.thissideup.fm/ Produced by: Intermode - https://www.intermode.is/ Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

    Solving the Fleet Software Adoption Problem with Eric Rodriguez, CEO of Vendorflow

  7. 07/08/2025

    Building the Future of Commerce Operations with Samantha Rose, CEO of Endless Commerce

    Join us for an incredible conversation with Samantha Rose, a multi-time founder who's built her career from creating a better spatula to running vertically integrated supply chains and now building cutting-edge ERP systems. Sam shares her unique journey through product design, 3PL operations, and the future of AI-powered business tools. In this episode of This Side Up, Sam breaks down how she scaled from a crowdfunded kitchen gadget to a full operations empire, the real challenges of running service-based businesses, and why she believes the future belongs to operators who actually love operating. Perfect for: Brand founders struggling with supply chain complexity, operations leaders looking to scale, or anyone curious about building in the AI era. Key Topics CoveredHow to identify and solve real problems (not just build solutions looking for problems)The hidden complexities of scaling through 3PLs and supply chain partnershipsWhy traditional ERPs fail operators and what comes nextAI-powered role-specific interfaces that actually work for different team membersStrategies for reviving distressed consumer brandsThe art of building sustainable partnerships with 3PLs and suppliersWhere AI is heading in logistics and supply chain managementAbout Samantha RoseSam is the founder of Endless Commerce (AI-powered ERP), Managing Partner at Hologram Capital (distressed brand revival), and previously founded Gear (kitchen products) and Mvnifest (end-to-end brand operations). She's a hands-on operator who's built businesses from product design through warehousing and everything in between. Episode Timestamps00:00 - Intro 01:24 - From Finance to Spatula Innovation 07:51 - From Product to Business Success 09:46 - Building Through the Supply Chain 13:35 - Focus and Multi-Business Strategy 16:58 - What is Manifest? 20:17 - Service Business Pricing Challenges 25:35 - Intermode - Sponsor Break 27:04 - Building Endless: The ERP Without Accounting 32:45 - AI-Powered Role-Specific Interfaces 35:36 - Hologram Capital: Distressed Brand Revival 42:12 - 3PL Partnership Strategy 46:58 - The Future of AI in Supply Chain 54:10 - Building in Volatile Times Connect with Samantha RoseLinkedIn: https://www.linkedin.com/in/samanthatrose/ Endless Commerce: https://www.endlesscommerce.com/ Mvnifest: https://mvnifest.com/ Hologram Capital: https://hologramcapital.com/ Show InformationThis Side Up Podcast digs deep into the minds of founders, builders, and operators reshaping the future of commerce and logistics. Subscribe for more conversations with industry leaders who are actually building the future. Podcast Website: https://www.thissideup.fm/ Produced by: Intermode - https://www.intermode.is/ Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

    Building the Future of Commerce Operations with Samantha Rose, CEO of Endless Commerce

  8. 03/26/2025

    Welcome to This Side Up

    Welcome to This Side Up—the podcast that flips the lid on logistics and supply chain innovation. I’m your host, Andrew Verboncouer, and I’m taking you behind the curtain of an industry that touches everything. From robots and AI to cutting-edge SaaS and game-changing services, we’ll dive into the big ideas—and the brilliant minds—reshaping how the world moves. We are NOT here to talk about foggy industry trends, we’re here to talk about the nuts and bolts behind the products. Why was THIS the thing that you created, what’s possible now, and how are you structuring your team to innovate when everything is moving. From raw materials, manufacturing, assembly, commerce, fulfillment, delivery—it’s all connected, and it’s all evolving. This Side Up is brought to you by Intermode, where we help you launch, improve, and modernize logistics and supply chain software. This is your backstage pass to the future of logistics—one container, one breakthrough, one story at a time. Let’s make ship happen. Show InformationThis Side Up Podcast digs deep into the minds of founders, builders, and operators reshaping the future of commerce and logistics. Subscribe for more conversations with industry leaders who are actually building the future. Podcast Website: https://www.thissideup.fm/ Produced by: Intermode - https://www.intermode.is/ Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

    Welcome to This Side Up
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    7 Episodes

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Welcome to This Side Up, the podcast about logistics tech and design. From robots and AI to cutting-edge SaaS and game-changing services, we’ll explore the big ideas—and brilliant minds—reshaping how the world moves through supply chain innovation.

Information