Sounds like the normal entrepreneurial journey and experience.

I certainly can understand the fear of falling into bankruptcy. We just filed it last year, not because of the business issues - rather nearly a million dollars in medical debt after major hospitalization and surgery for both myself and my baby.

I’ll share my insights from the experience of bankruptcy, being an entrepreneur who also had a failed business, and an experienced bankruptcy and debt management counselor:

Bankruptcy is not absolutely horrible if you have enough money to live comfortably on a cash only budget. It absolutely will suck if you are struggling after you file.

Regardless of the reason- two failed business endeavors, where you likely bootstrapped it, sucks so much out of you financially. Take a moment to address that elephant in the room by taking stock of the total financial loss from beginning to end for all of it.

Be honest about where you both are financially and what you both want to achieve short term. What would it take for another company to be started up? How much do you need to pull from your personal stash to get it up and going and sustain operation until you break even and pay back what you took from the household? How long will it likely take?

There needs to be a rough draft plan- write it down so you both can regularly go over it and see the progress.

The biggest thing I saw as a financial counselor was small business owners not budgeting well, not separating business from personal, keep pulling from personal because it was to accessible rather than seek other ways of drawing income in for just the business, poor cash flow management on the business side.

It may take trusting the numbers on how they play out. If you can show evidence of well thought out specific plan on growing savings, steady draws, and how you’re gonna scale this time before burn out- she may be able to take a deep breath and be reassured.

Also as a wife myself- it’s okay to tell us the Negative Nancy comments makes it hard for you to have the confidence and focus necessary to get this next stab at a business done right. Sometimes we just need you to hug us and hold our hands when you say it.

Is there a history of any of these creative ideas being carried out, where it takes time and money, but end up failing or fizziling out? If so, this may be an issue of mistrust or resentment. Do you need her input or approval or do you want her involved for sake of being close? Identifying the root issue is really important here. What is the fear that is driving the negative outlook on your creative ideas