25% of a craft brewery? Whats the anticipated ROI? How quickly can you get your money back out? Personally I don't agree with borrowing money for investing purposes. Its speculating, not investing IMO.
That's a fair point; definitely speculative - all investments are (at varying levels of risk). That money would have been safer in the retirement accounts without a doubt. This wasn't a move to try and beat returns there or even get a ROI at this point. I've been home brewing for a few years now, and it's something I enjoy doing. In that regard, I'll have an active role in the company, and am not just focused on how quickly I can get my money back out of it.
Sigh. OK. A few thoughts.
1. After four pages, my impression is that you tend to approach finances emotionally -- you have all of these great ideas that you want to do and things that you want to buy, and they all seem legitimate ideas/wants/needs because reasons, so you chase them all, and you end up with this giant pile of various assets and debts and accounts and businesses.
If your financial plan is to make money through businesses (rental properties, brewery, etc.), you need to put the emotion aside and run them like businesses. Look at the capital required, look at the likely ongoing expenses, figure out your ROI, identify your exit plan, and all of that. You have just started to do that with the rentals (FWIW, after the SFH sells, the duplex needs to go next -- there is no way you are actually making money on that given the very small delta between the rent and the mortgage). Now you need to do that same analysis with the brewery.
2. You need to recognize this aspect of your personality and
protect your family from its downside risks. Everything that Goldielocks said applies 100% here. Your finances are so smooshed together that you cannot possibly know whether your family is safe if the brewery fails and the rentals go vacant or need a new roof. You need a "safe" pot of money that ensures your family is protected if everything hits the shitter. Normally, that would be your retirement funds, but you have already raided them for the brewery. Your first order of business once the SFH sells is to pay off the CCs and then replenish that specific 'stache that is designated for your family and untouchable by you.
3. You need to slow down and stop going 1000 different ways at once so you can improve your planning skills. You jumped in and sold the car and paid down debt, all of which is good! But you left yourself completely cash poor, even though you
knew you had significant car repairs in your immediate future -- or you would have known had you been paying attention, because tires and brakes are not the kind of things that usually come as a complete surprise. And I guarantee you that this month is going to be challenging, too, because you'll suddenly realize that here are all of these Christmas expense that you haven't planned for. Follow Meesh's advice: sit down and project out
all of the infrequent/unusual expenses you have coming up over the next 6 months. Make sure you are setting enough aside in your budget to cover those expenses now. Throwing a lot of money at your CC debt, only to put more costs on the CC, is called "robbing Peter to pay Paul," and is
exactly why most people struggle to get out of debt. You just need to stop buying shit you can't pay cash for, period. Really, period. If the car needs brakes and isn't safe to drive and you don't have cash to pay for the brakes, well, you can find the money somewhere, or you can figure out how to get by without the car for a few weeks or a month until you have the cash again.
This is psychological training more than financial training: you will never break yourself of the habit of buying whatever you feel like, and you will never learn to live within your very ample means, unless and until you really, deep-down learn that CCs are not an option to rescue you from the inevitable or tide you over "just until the next paycheck." The road to hell and all that. So if you have to learn the hard way by doing without because you didn't plan appropriately, oh well.
4. Everything you have said about the brewery says that it is a hobby, not a business. Businesses are all about cashflow and ROI; if this were a business, you'd be valuing the return on your money -- or the potential use of those profits to otherwise improve the business -- much more highly than your personal enjoyment tinkering with beer and participating in the process. Either treat it fully like a business, or recharacterize it in your own head as a hobby, and then figure out if you can really afford a $50K hobby right now. Hint: you can't. Of course, I also don't think you can get out of it at this point, so now you need to do everything you can* to make it profitable. But use this as a lesson to restrain your impulsivity in the future:
no hobby businesses until your debt is paid off and your family is protected. Needs before wants and all that.
5. Finally, there is a huge, huge difference between "speculation" and "investment," and you are intentionally conflating the two in order to justify your strong preference for the excitement of the former. Stop doing that. If I buy stock in a company that has hard assets that are themselves worth more than the value of the stock, that's not "speculation" in the slightest, because if everything hits the shitter, the assets are sold and I get my money back. If I buy stock in a company that has a strong financial situation, tons of free cash to throw into new products or acquisitions, solid management, and a reasonable price in light of all of the above, that is not "speculation." There is risk, of course; life is risk. But it is a risk that any risk-benefit calculation says will pay off more often than not. OTOH, buying real estate without even looking at the return on your investment (because prices never drop and you'll make it back in the end, c.2006?), or deciding to open a hobby business with your buddies because you just love-love-love the product and so everyone else will too --
that is speculation.
IOW, there is always risk. But investors evaluate and manage those risks and pursue only those opportunities where the likely benefits outweigh the likely downside costs -- and they never invest more than they can afford to lose. Speculators chase cool ideas because they sound good, without doing any thorough analysis of the likelihood or magnitude of the risks (much less ensuring that those risks are proportionate to the likely benefits and won't bankrupt them). If you want to get the kinds of long-term returns you will need to support your family (which is exactly what gives you the financial freedom to engage in those expensive hobbies), you need to start behaving more like an investor and doing the hard work to really dig into those exciting opportunities before jumping after them.
*Other than throw more money into it. Not another penny.