We're bigger now, but our market has changed dramatically and we'll need to pivot/diversify successfully in order to avoid fading away in 2-3 years. So effecti

We're bigger now, but our market has changed dramatically and we'll need to pivot/diversify successfully in order to avoid fading away in 2-3 years. So effectively you’re asking whether you would invest a big share of your income over the next 8 years to buy more of this company as it is now, with a high risk profile. That’s a tough choice. Any likelihood of raising capital in the near future to fund expansion / pivot? An ideal outcome would probably be to sell them your wife’s shares as part of the deal & buy her out that way. Would be tricky to get everything to line up though. I am exploring transferring 1/2 my shares to her, which is less than ideal for a lot of reasons, but I suspect she and her attorney will fight to reject that (as it doesn't give her any cash). Not sure if it's possible or not. Downside of course is that then I'm in business with my ex-wife. As is my partner. Not ideal. But perhaps better than the alternative of paying her out over 8 years on top of the alimony... You don’t know until you make the offer! Something to watch out for: you’ll be paying off her share of the company out of taxed income. Make sure the numbers work for you: worst case, she earns nothing & that 32% + the fixed payment exceeds your income after tax + necessary expenses. This would be a bad outcome...