Ask HN: WWYD? Built a company valued at $1B and may walk away with nothing
I'm looking for some "What Would You Do?" advice from the founder and investor community. Generally looking for guidance on what I should be negotiating for and what type of downside protection is fair, in any?

Financial Overview

- At our peak (Series C) we were valued at $1B post money - $187M raised by the company
- $250M preference stack (liquidation prefs + debt)
- I own ~27% of the business, and so does my co-founder. My co-founder is no longer part of the business day-to-day, he's on the board
- We will end the year at $130M in annual revenues and burning ~$925K/month, we are a low gross profit margin business ~15-20%

Personal Overview
- I live in New York City, it's been ~ 10 years that I have been on this journey, bootstrapped with no salary for about 2.5 years and pretty modest salary for most of the years, up until a couple years ago when I started getting "market rate"
- I have not taken any chips off the table via any secondary sale up to this point, never really got the chance
- Today, my base salary is $175K, no bonus, no stock refresh since the founder grant, fully vested stock, no severance, no indemnification. (Mainly because I just haven't asked for new comp b.c company is in a difficult spot)
- In comparison, I hired a critical new C-Suite exec (COO) and gave her $285K/year, 75-150% annual target bonus, $150K sign on bonus, $200K funding closed bonus, 1-year severance, and a 4% equity stake in the business
- I am starting to see some worrying signs of real burnout now (for myself)

State of the Union
- We have < 6 months of runway based on our current burn, but majority of the money left is debt now
- I am about to close on $30M of additional financing this month but the terms will decimate common stock holders (my 27% stake is likely going to go down to < 10%)
- Still negotiating, but will likely have to give up board control so I could get fired immediately after financing is closed
- We are in parallel exploring strategic M&A alternatives this year, but in the current market condition our business is likely worth less than the preference stack, in which case common stock is wiped out anyways and I get nothing.
- Lastly, I'm not confident on the current strategy to grow out of the current problem over the next couple years, so there's a lot of risk in our growth for 2024 and beyond. The strategy I would want to run as CEO is likely not something my COO or board will want to get behind and frankly I don't know if I have the energy to do it myself. It would require 24-36 months to transition the business to the new world while watching old revenue decline and waiting for new higher margin revenue build up in parallel to offset the declining revenues in the core business.

My #1 priority is to get the financing closed for the business. But from there, I'm really confused and don't know what to do next. Doesn't seem to make sense for me to work my ass off just to return money to investors and have nothing for myself. But I do understand that it is my fiduciary obligation as the Founder/CEO, but maybe for the first time in 10 years I'm asking the question "What's in it for me?"

WWYD?