Upwell Insights: Smarter Finance for Logistics

Why Freight Brokerages Lose Margin Building Technology They Could Already Have

Silas Sorilla — Thu, 11 Jun 2026 14:33:28 GMT

It Always Starts The Same Way…

At some point in the growth of almost every freight brokerage, the back office starts to crack. Invoices slow down, disputes pile up, and the manual work that used to be manageable starts costing real money. And almost every time, the same conversation follows.

Is Freight Factoring Costing You More Than It’s Worth? When to Switch

Silas Sorilla — Thu, 30 Apr 2026 17:01:33 GMT

Why Freight Brokers Use Factoring

For most freight brokers, factoring is not a strategic decision. It’s a practical one.

How Freight Brokers Can Stay Profitable during Global Conflicts and Rising Oil Prices (Not Another Cost Cutting Strategy)

Silas Sorilla — Mon, 06 Apr 2026 15:56:52 GMT

Diesel prices are rising again and this time the impact is hitting faster than most freight brokers can adjust. As of January 2026, fuel costs represented 20-40% of total costs for carriers, with the sudden and uncontrollable increases (27% increase on prices since February 28th, 2026) the whole industry is facing even tighter margins.

“I Sold My Car to Make Payroll.” How Upwell’s CEO, Turned a Freight Cash Flow Crisis Into a Company

Silas Sorilla — Mon, 06 Apr 2026 15:56:27 GMT

Most companies are built on a vision. Some are built on a problem. But, the best ones are built on both, and the founder has the scars to prove they understood the difference.

From Freight Chaos to AI Judgement: How Upwell is Reshaping Order-to-Cash

Silas Sorilla — Mon, 06 Apr 2026 15:56:18 GMT

In a recent episode of Between Two Quarters, Charley Dehoney, co-founder and CEO of Upwell, broke down how a decades-long frustration with freight's order-to-cash cycle became the foundation for an AI-native platform.

The Operational Friction Quietly Slowing Freight Broker Payments

Silas Sorilla — Mon, 06 Apr 2026 15:56:04 GMT

In freight, the conversation almost always gravitates toward growth. More shippers, more loads, more volume. But in a recent episode of The Freight Coach, Charley Dehoney, co-founder and CEO of Upwell, made a point that doesn't get nearly enough attention: growth without back-office discipline doesn't build a business. It slowly drains one.