I'm rooting for these guys - it looks like their COO has been in waste management since 1999 (and, from the article, his family's been in it for decades). As a casual observer of "non-sexy" startups, I've noticed that these kinds of founding teams do well.
Returnbase (reverse logistics), CropMetrics (agtech), Weather Analytics (ag. insurance), and Loop Support (customer support, shameless plug) come to mind.
It's tough to "casually observe" startups because you can't flip through their 10-Ks, but you can think of individual startups metonymously - learn more about their industries, and then try to figure out why these startups are trying to use technology to make better products.
They will most certainly do well! They're essentially a Broker++ since they are treating the haulers as their customer too (or at least saying that). Brokerages have traditionally treated the haulers poorly so if they can get the relationship with the hauler right things should work out really well for them.
Either way I predict success. Down the line they'll be acquired by Waste Management, Republic, or Waste Connections to become another Oak Leaf.
