@Joe S. good point and glad you brought it up. You’re correct that there’s a sense of immediacy in making the entire investment in a short period of time. The cash flow from the investment would be intended to replace a W2 income and the funds would come from my retirement account. I’m sure that’s not an uncommon situation. What may be somewhat unique is the retirement account isn’t technically a 401k that I can access whenever I want - it’s private company stock which I can only cash out upon death, termination, or retirement. So in order to access the funds and start investing, I have to leave the job (and the salary). Doesn’t allow for much of a gradual transition.
Technically I could line up a replacement job and let that pay the bills while I invest slowly (and that’s definitely one of my contingency plans) but in some ways that does defeat the purpose, since leaving the corporate world and focusing all of my time on an investment business is probably the biggest appeal for me. My goal is to achieve enough cash flow to replace about 75% of my w2 salary (my wife will keep her job, and benefits).
If this sounds like the world’s dumbest decision to anyone, I’m open to hearing some hard truth from people who have been doing this. But ultimately I’m not opposed to taking a calculated risk as long as I have a complete picture of the situation.
Apologies if this drifted from the topic of the original post but I think Joe’s question drives to the reason that I don’t have an easy way to slowly build up the experience that I asked about initially.
Thanks everyone for your input so far!