How do I get businesses to adopt my web app in a market where the businesses aren't already on the web?

It sounds like your potential customers do not apprehend the value since they don't understand the product/market. I've been there and failed, twice.

Educating customers for a new market idea takes enormous amount of time and money. I woudn't do it unless I absolutely believe in the end result. And unless I have 10x times cash in the bank for projected marketing expenses.

Easier and more cost-effective approach is to piggyback on a big players who are already spending lot of resources educating customers about this new market. E.g. they might be already using Google to search the web and you can explain how your product complements this.

Try to talk with several prospects to understand how to pitch your customers. Then cold call, mail and otherwise reach out. Test your message and refine.

There are many ways you can start building relationships with your potential customers for free. The trick is, you want to build the relationships before you're done building your product, that way you'll already have evangelist and users when you launch.

• Find a forum that your small business user groups participate in (every industry has one) and start answering their questions. Do not hawk your products. You will slowly be accepted as a valuable member of the community and people will start inquiring about what you do.

• Start a blog - Start blogging topics relevant and useful to your potential customers. Give them free knowledge and help them solve problems. Do not pitch your products on your blog

• Use a service like TweetDeck to monitor social networks for words related to your product, and answer peoples questions

Give them free ipads! that usually gets them on the web really fast.

Well this sounds like our experience with newspapers 10 -15 years ago ...

We attended conferences, answered questions etc. It took a critical mass to grow, one after the other ... looking back the first few were worth so much more than the money we got from them ... invest your time, ask for their recommendation ... it is worth far more than the money you are likely to get from them.

More basic strategy:

• Make them feel comfortable
• Invest more in support ... no one does it, every client wants it ... we make our difference based on it and have 80% of the Australian newsprint market and key sites in the US and Canada because of our product AND our support.
• Offer 6 - 12 months "risk free"
• Do your research on a candidate, fill in as much in your system before you meet them, define a questionnaire which allows you to fill in the rest for them.
• you need a critical mass .. it could be 10, 20, 100 or a key player that everyone else looks up to ... if they do it, it must be OK.

Your job is NOT to win over all of them, just enough to convince the others. Each one signed on make the rest easier.