Everybody in this industry loves to talk about the last mile. It is the one the customer actually sees, the one with the delivery apps and the little truck icon crawling across a map, and the one that gets all kinds of conference panels and attention. The first mile gets almost none of that attention, which is funny to me since it’s where all supply chains start.

The first mile seems to be more difficult to define, depending on who you ask and where they are in the chain. Its truest definition is that it is the very start of everything, raw goods coming out of the source and heading somewhere that turns them into product: produce leaving the field for the packing house, ore coming out of the ground toward the smelter, fish off the boat and into the processing plant, etc.

I've never gotten hair extensions, but I came close once. Mid-twenties, a truly brutal haircut, and the hard-won discovery that the bob is not for me. In the end the price tag talked me out of it and I grew out my mistake the slow way. What I know now is that the price was the least interesting question I could have asked about extensions.

Before I go any further, one thing needs to be said. This post is not about shaming anyone who wears extensions or wigs. Hair is personal, it's cultural, and for a lot of people it's non-negotiable. This is about the supply chain behind the product, because it has a traceability problem that would get any other industry dragged, and somehow it barely gets talked about at all.

Big buyers have a whole playbook for paying their suppliers less than they actually owe. The three most common tactics: invoice short pays (paying slightly less than the invoiced amount, usually by amounts too small to dispute), payment delays (slow-walking remittances past agreed terms), and unilateral deductions (chargebacks and fees the supplier never agreed to). None of it is technically illegal. All of it adds up. Here's how the squeeze works, why it keeps working, and what suppliers can actually do about it.

Picture an invoice for $4,800 and the remittance comes back at $4,799.83. Seventeen cents short. You notice it, sort of, but you'd have to pull the original purchase order, match it against the remittance, draft an email, follow up twice, and maybe escalate it before anyone replies.

Let's talk about return-to-office, because the headlines have been hard to miss and the takes have been…something.

By Q2 2025, JLL reported 54% of Fortune 100 employees were under five-day office mandates, up from 11% the year before. Heading into 2026, Instagram pulled US staff back to the office five days a week, Microsoft tightened to three days, and NBCUniversal moved to four (with a voluntary severance package for anyone who didn't like it). And those are just the names you've heard of. Some of the largest freight brokerages in North America are doing the same thing, quietly or otherwise.

I've run a brokerage remotely since 2016 and I've been a full-time digital nomad since 2022. I've worked from twelve countries in the last few years and the freight has continued to move, the customers have continued to get serviced, and the carriers have continued to get paid. So forgive me if I'm not buying the productivity argument.

Last week, the US Administration extended the Jones Act waiver another 90 days. And it barely seems to have registered. And even in logistics, the industry that should care most, the reaction was kind of just a collective shrug.

Which is strange, because this is one of the messiest, most-nuanced shipping stories of the year, and the reason it's messy has almost nothing to do with the waiver itself. It has to do with about a hundred years of decision-making that got us here.

There's a whole shadow world operating underneath legitimate global shipping, and it's bigger than most people realize.

The dark fleet (also called the shadow fleet) is a loose network of oil tankers that move sanctioned crude around the world, specifically designed to get around Western trade restrictions. It's not a coordinated cartel with a headquarters somewhere. It's more like a swarm, hundreds of vessels operating under a shared logic: move oil that isn't supposed to move, and don't get caught. Or the IMO definition is vessels engaging in illegal operations to circumvent sanctions, evade safety/environmental regulations, or bypass insurance costs, typically using deceptive tactics