Hi Serial,

It sounds like you're setting yourself up for a crash. The kinds of long term obligations you are describing are perfect examples of the factors that lead to the 'Ponzi' models; robbing peter to pay paul.

Eventually, everything comes to a screeching halt.

It's far better, and healthier, to work trades or set pay-offs than to obligate yourself to some 'down the road' cash out. Interest on loans at a startup phase will kill your cash flow. Equity for work performed, especially if the value of the company's business increases beyond projections will lead to hard feelings and that 'could kick myself' feeling.

So, to answer the concerns in your question, don't do it! Find another way to 'keep the slate clean'. You'll be far happier in the end.

Good Luck!

From My own experience My company (startupshoppe.com) works solely with start-ups and we have a model that takes equity AS PART of payment (usually half stock half cash) and that seems to have worked quite well over the years. I've been at this for 9 years now.