Most of the T&L market is spot freight though. A carrier with 5 trucks isn't going to win much contracted and so he's essentially running 5 freelancers on day-to-day loads, the only way to keep that profitable is to minimize deadhead miles which you need a TMS for.
I'm not saying he needs to scale to infinity but it sounds like the issue is that he's spending hours or even days of his time to save 100 bucks.