@Richard Darnell, great post!! You're asking some important questions, which shows you are seriously trying to find your best path forward! For context, I've been an investor for 16 years, with a $10M + portfolio. I'm also a Psychologist and Certified High Performance Coach and have facilitated masterminds around investing (and other topics). I am IN the field of support because I've experience how much growth comes from intention work on oneself and their goals. I've been the benefit of mentorship & coaching (and I do it every week with others). Here are my thoughts:
1. You can learn a lot from books, and I think reading is a must always. What a mentor can do is help you apply that knowledge in the most practical way. They will see pitfalls and challenges that you can't simply because you are in new territory. I've had investors look at a challenge in my portfolio and give me a solution that left my jaw dropped because I hadn't thought of that or because I never even HEARD of that solution before!
2. Success is about who you know. I've advance my investor life more in the past 3 years, once I made the commitment to start getting to know people who are like me. A few key people have made introductions that have been very fruitful! If the mentor is plugged into some good communities, they will have a good strong reputation that you can build off of. Trust takes time. But being able to piggy back off someone else's trustworthiness is the only "shortcut" I know.
3. This is one of the best aspects of a mentor or coach. In many businesses I've been part of, I get frustrated and discouraged when things don't go they way I expected. Did I mess it up? Are things actually going right and I just need to persevere? Do I change course? These are hard questions to answer solo. So having a knowledgable person to consult, bounce ideas off of, and to help YOU stay accountable to YOU. As a Coach, I don't hold people accountable. I help them be accountable to themselves. When they struggle, we work through the why and the how to honor oneself enough to do the hard things that you are committed to.
4. I was a General Partner on a Syndication last year for a period of time. There was a significant lack of communication and I was feeling less excited about it. After talking to two good friends in the business, I made the hard decision to back out of the GP. Turns out, almost a year later, the main GP is having serious problems with multiple syndications. LPs are losing millions. And I am able to sleep well at night knowing that I was guided by friends and mentors to do the hard thing that my gut was telling me. I dodged a bullet. And I'm not sure I would have done that if I didn't have good counsel.
5. A good mentor or coach will help point you to the right info, share their mind, and most important, help you develop an improved internal system to increase your momentum. For example, the style of coaching I do helps people organize not just their investing but their whole life. It helps bring everything into alignment. What I've seen is that often investors don't stay stuck because of lack of knowledge. But rather because something else in their life is off. Sometimes it's a lack of confidence (and when you're working with someone, you can "borrow" their confidence), and sometimes it's things like not having a spouse fully on board with investing or having a job that is pulling you away. There are great ways to help improve these areas!
Lastly, I'll comment on mentor v coach. Mentor's are people who have "done it". They can shine a light on your path so you have more clarity on your next steps. A Coach is someone who has the capacity to help you think and act more expansively, creatively, and effectively. They help you grow so that you are the person you need to be to have the success that you want to have.
Ideally, you'll find a coach and mentor in the same person.
