All of this is known and commonly discussed in risk-management and HR education. Pretty much every lesson's conclusion: unless the person is mission-critical to revenue generation, there is no way to justify this kind of risk. Terminate the employee before their problem becomes yours. If an investment/debt-reliant startup is ignoring these plain and common due diligence practices, it sends up a lot of red flags. Rising interest rates, public tranny fatigue, and tech-sector contraction is not a conducive environment to carrying someone like this. No investor, lender, or executive likes anyone enough to face an existential risk like this.