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 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/

Produced by: Intermode - https://www.intermode.is/

Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

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/

Produced by: Intermode - https://www.intermode.is/

Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

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/

SearchCarriers
https://searchcarriers.com

LoadPartner
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/

Produced by: Intermode - https://www.intermode.is/

Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

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/

Produced by: Intermode - https://www.intermode.is/

Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

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

Connect with Eric

LinkedIn:
https://www.linkedin.com/in/ericrod/
Website:
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/

Produced by: Intermode - https://www.intermode.is/

Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

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 Covered

• How to identify and solve real problems (not just build solutions looking for problems)
• The hidden complexities of scaling through 3PLs and supply chain partnerships
• Why traditional ERPs fail operators and what comes next
• AI-powered role-specific interfaces that actually work for different team members
• Strategies for reviving distressed consumer brands
• The art of building sustainable partnerships with 3PLs and suppliers
• Where AI is heading in logistics and supply chain management

About Samantha Rose

Sam 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 Timestamps

00:00 - 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 Rose

LinkedIn: https://www.linkedin.com/in/samanthatrose/

Endless Commerce: https://www.endlesscommerce.com/

Mvnifest: https://mvnifest.com/

Hologram Capital: https://hologramcapital.com/

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/

Produced by: Intermode - https://www.intermode.is/

Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/

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 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/

Produced by: Intermode - https://www.intermode.is/

Host: Andrew Verboncouer - https://www.linkedin.com/in/andrewverboncouer/