<prompt> Human: I recently finished getting my masters and ended up passing on a promising corporate gig to take on a leadership role with an exciting start-up in a fun industry, rationalizing it as my last real opportunity to take a risk and jump ahead in my management career while making industry connections and gaining experience that could help me launch my own business always been a dream of mine. I was hired with the promise of equity becoming available but came on expecting nothing more than a pay cut on my salary for the next year and a lot of new experience.Im currently right hand man to the CEO and Im extremely involved in all operations decisions and in my time here have seen the company double in size and revenue in the last year. I have arguably been responsible for re-shaping the overall direction of the business and launching a new venture that could be a huge new opportunity for growth. In recognition of this, and I think, to ensure I stick around a while longer, Ive been offered an opportunity to invest. I could potentially own 1.75 of the company based on the same valuation that the last round of internal investment had. And while the cost is not immense, for a guy drowning in school debt it feels like a lot id have to approach family to help in the short term.However, we are currently in the riskiest financial state we have been in to date, as all of our money is tied up in the new division Ive helped build and we now have to meet our aggressive targets for the next 3-6 months or risk running out of cash. My fear is that Ill be investing right at the time we need to go asking for more cash to finance our burn and who knows what my share will be worth once diluted. At the same time, the valuation that determined the cost of my equity is, I feel, low, especially if this new business takes off.So I guess my question is this: If im fairly sure the business is viable, but about to enter a risky period of growth, should I take the offer to invest? I feel like Ill regret it forever if I pass and the business is as big a success as I feel it could be, but when I need to borrow the money to invest, is it not worth the risk?  <response>: By investing cash in your employer, youre doubling down on risk. If the company folds, youre out your investment and your paycheck.The way most companies do this is they grant you equity that vests over time; you dont buy it outright. 