Thanks for the question ... 

One way to weigh the tax implications is to consider whether this activity is truly a "business" vs. a "hobby".

The guidance from the IRS in this regarding is as follows:

https://www.irs.gov/newsroom/heres-how-to-tell-the-difference-between-a-hobby-and-a-business-for-tax...

A hobby is any activity that a person pursues because they enjoy it and with no intention of making a profit. People operate a business with the intention of making a profit. Many people engage in hobby activities that turn into a source of income. However, determining if that hobby has grown into a business can be confusing.

To help simplify things, the IRS has established factors taxpayers must consider when determining whether their activity is a business or hobby.

These factors are whether:

• The taxpayer carries out activity in a businesslike manner and maintains complete and accurate books and records.
•  The taxpayer puts time and effort into the activity to show they intend to make it profitable.
• The taxpayer depends on income from the activity for their livelihood.
• The taxpayer has personal motives for carrying out the activity such as general enjoyment or relaxation.
• The taxpayer has enough income from other sources to fund the activity
• Losses are due to circumstances beyond the taxpayer's control or are normal for the startup phase of their type of business.
• There is a change to methods of operation to improve profitability.
• Taxpayer and their advisor have the knowledge needed to carry out the activity as a successful business.
• The taxpayer was successful in making a profit in similar activities in the past.
• Activity makes a profit in some years and how much profit it makes.
• The taxpayer can expect to make a future profit from the appreciation of the assets used in the activity.

All factors, facts, and circumstances with respect to the activity must be considered. No one factor is more important than another.

If there is a genuine sense that this is really taking the shape of a business, I would deduct the cost of the mentorship expense and I also deduct the cost for the renewal of the coaching program.

Others may have a different view, but this how I see this based on what you have described.  It really hinges on intent, purpose and effort in trying to get a new business up and running, and ultimately profitable (and some of this is a judgement call).