The Founders Lounge

In this episode of the podcast, we sit down with Adam Robinson, a master of niche B2B marketing who has dedicated the last 14 years to decoding how to market to shippers, global manufacturers, and logistics providers. We trace Adam’s timeline from his early days hosting live web television and running high-velocity digital sales teams, through his years architecting the marketing engines behind companies like Cerasis, Turvo, and FreightWaves, to building his own powerhouse specialized agency. Adam breaks down why "safe doesn't scale" in the logistics sector, shares his framework for hyper-lean operations, and explains how to build an "edutainment" funnel in a traditionally rigid supply chain landscape.

In this episode of The Founders Lounge, we sit down with Jim Heide, Co-Founder and COO of Loadsure, whose 25-year journey traces nearly every major evolution in logistics. A U.S. Marine who landed in the industry almost by accident, meeting the right person in a Denver bar, Jim came up from the warehouse floor at Perry Transfer, warehousing everything from toilet paper to Ferraris (and raw metal for the U.S. Mint), before riding the wave of consolidation that turned a local drayage outfit into part of the $6.7B Exel/DHL Supply Chain machine. He made the leap into FreightTech at 10-4 Systems, where his operational grit helped make the company exit-ready for its acquisition by Trimble. Then he took his biggest risk yet: becoming employee #1 at Loadsure, teaming with 20-year Lloyd's broker Johnny McCord to build the industry's first digital MGA — using AI to disrupt a centuries-old cargo insurance market and close the freight "underinsurance gap." This is a story about operational resilience, betting on yourself, and building a 40+ team, Lloyd's-backed insurtech from a two-person idea.

In this episode of the podcast, we sit down with Charley Dehoney where we trace his 22-year journey from the early days of door-to-door shipping sales to his current mission at Upwell to automate accounts receivable for the logistics industry. Charley shares the "grit-filled" reality of modernizing a 50-year-old brokerage and explains why he believes AI-driven invoicing is the key to surviving the next iteration of freight brokerages.

In this episode of The Founders Lounge, we sit down with Travis Rhyan, a seasoned entrepreneur and tech leader who has spent over two decades architecting the digital infrastructure of the freight industry. From building proprietary TMS solutions at GlobalTranz to leading 10-4 Systems through its acquisition by Trimble, Travis has been at the forefront of the "FreightTech" revolution.We explore his journey from founding and selling a truckload brokerage in the early 2000s to his roles as Chief Product Officer at FreightWaves and MyCarrier. Now, with his latest venture Carrier1, Travis is tackling the sustainability and longevity of asset-based carriers through leading-edge connectivity. We also dive into his unique lifestyle, balancing the high-speed world of logistics tech with his off-the-grid organic farm in Maui.

In this episode, hosts Coleman and KJ sit down with Robert Nathan, a serial entrepreneur, investor, and visionary leader who has spent decades shaping the logistics, freight tech, and AI landscape.

From starting on the loading docks at 14 years old to building, scaling, and successfully exiting multi-million dollar enterprises, Robert shares the raw, unfiltered realities of the founder's journey. He dives deep into the ultimate highs like landing on the Inc. 500 list and the brutal lows of having to downsize a company to survive an economic crash.

Whether you are an aspiring founder, a logistics professional, or curious about how artificial intelligence is rewriting the rules of global supply chains, this masterclass in resilience and innovation is a must-watch.

📌 Key Takeaways From This Episode:

The "Axe" vs. The "Hatchet": Crucial leadership advice on making swift, decisive corporate changes when the market turns against you.

Building a Sellable Business: Why the best companies don't actually get sold, they get bought.

The Rise of "LaaS": Robert introduces his thesis on the future of Logistics as a Service and why AI innovation must come from inside the industry.

The Future of Freight Brokerage: Will brokers exist in 10 to 15 years? Robert breaks down the striking parallels to Wall Street and Robinhood.

⏱️ Timestamps:

00:00 – Welcome to The Founders Lounge

00:43 – Starting on the loading docks at 14 and building a problem-solving mindset

05:35 – Why a strict "no nepotism" rule was the greatest gift from Robert’s father

06:07 – From studying philosophy at CU Boulder to navigating business systems

08:45 – Entering the legendary Chicago freight brokerage ecosystem

10:55 – Answering phones & starting from the absolute bottom at AFN

14:20 – Becoming an "intrapreneur" & creating new multi-million dollar business units

16:10 – The danger of shifting commission structures & launching Load Delivered Logistics in 2008

18:50 – The modern brokerage model: Why cradle-to-grave is winning today

22:00 – The loneliness of a startup's first day

25:30 – Surviving the brink of failure: Right-sizing headcount from 184 to 77

27:50 – The Axe vs. The Hatchet: Brutally honest leadership advice

29:40 – Founding Logistical Labs: Solving the big data and pricing algorithm puzzle

33:20 – Exiting to HIG Capital & learning to be an executive at a billion-dollar company

37:30 – Moving to Venture Capital: The difference between emotional operators and logical investors

39:50 – The Go Romeo camper van journey & pivoting to industrial real estate during COVID

43:00 – Evaluation Strategy: Is it the jockey, the horse, or the tailwind?

44:45 – Launching Envoy: Orchestrating the next wave of AI in logistics

50:30 – Super Intelligence and what the job market looks like in 15 years

54:00 – Will freight brokers survive the AI revolution? (The Robinhood analogy)

55:20 – Open Mic: Robert's secret high school reality TV past!