It can be a tricky situation when there is not a distinction between investors (those writing the checks) and the operating team (those spending the money). Th

It can be a tricky situation when there is not a distinction between investors (those writing the checks) and the operating team (those spending the money). There are different incentives and motivations for the two sides and it has a tendency to create power dynamics that are not always best for the business. The fact that you worked together previously and presumably had a positive experience, is a good sign. Based on your description, I would make the observation that titles are not the biggest potential issue here, but who is making the decisions that drive the business forward. If the investor/cofounder is trustworthy and has the success of the business as the key motivator, then you could be ok. The other issue is that investors and operators get two different classes of stock: investors get preferred shares and employees/team get common stock. This is another potential issue. I would suggest talking to him and getting clear on what is best for the business and what he wants out of this: an investment or a job.