In this episode of Driving Forward, I sit down with my friend Charley Dehoney to talk about what it really looks like to build in this industry when the stakes are personal. We get into buying and scaling a legacy brokerage, feeling the pressure of payroll, and carrying the weight of knowing other people’s families are tied to your decisions. We talk about growing up in logistics, trying to be a present husband and dad while still chasing big outcomes, and what it costs mentally and emotionally to keep pushing when the easy choice would be to tap out.We also dig into the side of freight most people do not want to talk about in public. The broken billing. The AR black hole. The quiet back office killers who keep companies alive while chaos swirls around them. Charley shares why he built Upwell, how he thinks about cash flow as a growth engine instead of a headache, and where AI and automation actually fit in for real operators. If you live in this space and you have ever asked yourself whether all of this is worth it, this conversation is going to hit very close to home.
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