First, many SMB owners are highly technophobic. No matter how good your product is, if they straight out fear technology, you aren't going to get anywhere with them.
SMBs, by definition, are small, and many run on credit card debt during the slow months. They don't have the luxury of finding investments like a tech company. Since most of them are bootstrapped, it is hard to ask for $5k / month from SMBs. If they can hire on 3 people for the same price, where do you think they are going to spend that money?
Unfortunately, many SMBs are stuck in a hard place with tech. The tech they can afford is pure trash, a total displeasure to use, crashes on a weekly basis, and so obviously bad that no one needs a math degree to understand that this product is a money pit, and likely ends up costing more to use than it would if everyone was doing things by hand.
On the opposite end, the products that are worthwhile to use are a) too expensive and b) the technology companies don't want to play small ball, so the SMBs they talk to tend to walk away feeling disrespected.
When you have a technophobic, cautious SMB owner as a customer, playing a game of "push and see it break" isn't going to work. These products end up stalling out the entire business for a morning, and the costs of paying for employees not working, then tacking on overtime, reflects poorly on these products.
I totally believe that the SMB space is ripe for massive disruption. The current tech offerings are old, buggy, slower than molasses in winter, and doesn't work as promised. The problem is, who can get to the gate first with a product that is cheap, productive, and obviously not the product of people with no domain knowledge.