Make obvious, make it simple, make it attractive. Yesterday, following my first day with TAC, I had a presentation to make. TAC's approach and specific twist on that approach not only gave me hope that this time will be the right time, it drove the reflection for the presentation. The dabbler conversation was almost as if you see into my life along with all the starts and stops I have made throughout the years.
One suggestion, you might think about a deep link for new users to the play in 30 days or at least present the option based on self assessment. I first tried to keep up with the first video presented, giving up, I went to the daily challenge. The daily challenge started with a 4 fret wide exercise on low E.. I little steep for day 1. What have I gotten myself into? 30 days starts a little too far back but at least gives you the "I've got this" success feeling.