If you look at the matter from a spherical point of view, you will notice that the concept of entrepreneurship is divided in different stages. And although entrepreneurship, as a whole, might not be easy or possible to teach, some stages might be:

• The Idea Stage. To be an entrepreneur you need an idea to build on. The original idea that will be giving birth to your company. And no one can teach you how to think and innovate. The idea will have to be something that you will come up with on your own.
• Setting up a business plan is the second stage. You need funding and the right business plan will be able to give you that funding. Now this stage can be taught. Business departments in colleges and universities all around the world have classes that focus on teaching future businessmen and businesswomen how to create successful business plans.
• Setting up the company, after you receive the funding is the next stage. This is where things get a little tricky. Although the way you are going to be choosing your employees might follow a certain pattern, you also need, what entrepreneurs call, critical way of thinking. The details will be based on the original idea as well as the future that you visualize, for your business. No one can teach you how to think and judge based on the needs of your company because no one knows them apart from you.
• Last but not least we have the evolution stage. You have created your business plan. You got the funding you needed and you hired your employees. Now is the time for you to put your ideas into practice and start evolving them and here is where creativity comes in. Creativity skills cannot be taught in a classroom. They are acquired through experience and through creative thinking processes. One cannot learn to be innovative and entrepreneurial, while on desk duty.  You need to explore things, use your imagination, question assumptions and connect information in order for you to achieve the best result.
  

Some entrepreneurial skills can be taught and others cannot. “The key factor is motivation.” The teachers need to be motivated in order to teach important parts of entrepreneurship to students and students need to be motivated in order to understand the importance of the entrepreneurship skills and learn them. “Entrepreneurship can, partially, be taught.” But without imagination, innovation and a thirst to meet the unknown people will not be able to become true entrepreneurs.

In some ways it can be easier to start a new business based on the idea of Digital Entrepreneurship - there are no changes required - just set up a new business environment that supports your digital business model. Restarting and implementing the digital tools step by step can be more difficult since you need to take care of the existing business and the customers and other relations you have worked so hard to reach. In that case you need to create a "step-by-step" digitization plan to secure the change. Depending on if you are a solopreneur or have employees you also need to involve your staff or partners in the process. Maybe you need to replace staff/partners to get the required competences into your business - or maybe start a training process in parallel with the change.
Whatever it takes - you need to analyze the situation and start moving in the direction of a digitally supported or digitally based business.

If you are an Entrepreneur with some experience you have probably already faced several of the challenges that Dan Western, founder of the Wealthy Gorilla,  mentions in this article posted by David Seagraves. 
If you are working with entrepreneurs and individuals on their way to become entrepreneurs - these are 8 challenges that you need to prepare them for. To the article...

The Internet of Things might seem like it only benefits large corporations with massive budgets, but the IoT has already started to bear fruit for small businesses, too. In fact, approximately 57% of small business think the IoT will have a significant effect on their bottom line, according to an AVG survey.
BI Intelligence expects that from 2015 to 2020, business investments in the IoT will grow from $215 billion to $832 billion. This is just one slice of the overall pie, as compounded, we project more than $6 trillion will be spent on IoT solutions between 2015 and 2020 among businesses, consumers, and governments.
Read the full article here