[mikepmalai]

Many of the emerging enterprise centric companies you hear about today initially got their start selling to SMBs/sole proprietors. Instead of targeting large enterprises from the get-go, start with small business owners and talk to them about their pain points and the issues facing their business. Odds are you'll identify a problem that you can profitably address quickly (enterprise sales cycle sucks) and sell later on to larger enterprises who have the same problem (if that's the eventual direction you want to take).

For example, maybe after talking to a bunch of pool cleaning companies you realize that there's a dire need for a phone app to track where cleaning crews are and what work they've done. They are more than happy to pay you since the app would save them thousands of dollars per year in various losses. After organically growing this business over time, you realize that other industry verticals with distributed workforces have a similar problem so you begin to expand and target larger businesses...you get the point.