What's holding you back from making your first/next real estate investment?

Given there are a lot of experienced investors here, I (and many others) would benefit a lot from learning the full stories of those who have invested in dozens of properties over the course of years/decades. I was thinking an in-depth profile on particular investors about how they got started, how their scaled their investments over time, and how things are going now (best lessons learned) would be good to share.

Would experienced investors be willing to share their stories in great detail? And would newbies/amateurs looking to buy their first property or scale up benefit from reading these profiles?