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

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/ [https://www.upwell.com/] Connect with Charley Dehoney: https://www.linkedin.com/in/cdehoney/ [https://www.linkedin.com/in/cdehoney/] SHOW INFORMATION This 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/ [https://www.thissideup.fm/] Produced by: Intermode - https://www.intermode.is/ [https://www.intermode.is/] Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/ [https://www.linkedin.com/in/andrewverboncouer/]

$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 EPISODE * Why "Uber for trucking" failed and what Parade built instead * The economics: $44 per load, 35% of total lifecycle costs * How 20% of carrier calls get dropped before reaching brokers * The carrier conversation funnel: 100 calls to 4 bookings * Co-Driver's AI negotiation: filtering 55% of wasted conversations * The Centaur model: Why AI + human beats both alone ($39 proof) * 7 million automated conversations and counting * AI-to-AI freight negotiations: The weird new reality * 4x productivity gains: From 50 to 200 loads per week per rep * Automating $1B of the $100B annual freight brokerage market * The path from 70% to 100% digital freight coverage * Why data freshness matters more than TMS capabilities * Building carrier relationships from transactional freight * The three pillars driving rapid AI adoption in freight ABOUT ANTHONY SUTARDJA Anthony 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 TIMESTAMPS 00:00 - 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 INFORMATION This 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/ [https://www.thissideup.fm/] Produced by: Intermode - https://www.intermode.is/ [https://www.intermode.is/] Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/ [https://www.linkedin.com/in/andrewverboncouer/]

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 ALLEN Garrett 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/ [https://www.linkedin.com/in/allengc/] SearchCarriers https://searchcarriers.com [https://searchcarriers.com] LoadPartner https://get.loadpartner.io/ [https://get.loadpartner.io/]   SEGMENTS 00:00 - 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 INFORMATION This 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/ [https://www.thissideup.fm/] Produced by: Intermode - https://www.intermode.is/ [https://www.intermode.is/] Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/ [https://www.linkedin.com/in/andrewverboncouer/]

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   SEGMENTS 00:00 - 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 INFORMATION This 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/ [https://www.thissideup.fm/] Produced by: Intermode - https://www.intermode.is/ [https://www.intermode.is/] Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/ [https://www.linkedin.com/in/andrewverboncouer/]

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. SEGMENTS 00:00 - 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 NOTES https://www.thissideup.fm/episode/how-vendorflow-solved-driver-app-adoption [https://www.thissideup.fm/episode/how-vendorflow-solved-driver-app-adoption] CONNECT WITH ERIC LinkedIn: https://www.linkedin.com/in/ericrod/ [https://www.linkedin.com/in/ericrod/] Website: https://www.vendorflow.co [https://www.vendorflow.co] SHOW INFORMATION This 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/ [https://www.thissideup.fm/] Produced by: Intermode - https://www.intermode.is/ [https://www.intermode.is/] Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/ [https://www.linkedin.com/in/andrewverboncouer/]