Asking for an extension on a venture debt line is a pretty common request from startups. They do this because they want to be able to preserve the ability to draw the loan, but don’t need it quite yet. So they’re going to ask the lender to extend that drawdown period.If it’s a short drawdown, the lenders are usually pretty happy to comply. After all, they want you to draw the money down. That’s how they make money on interest.However, it’s going to be a lot easier if it’s a short term extension, like one or two months, because anything longer than that, they’re starting to extend the risk.Tips for maximizing the chances of getting an extension:Have this conversation at least two months before the extension, before the original line runs out. Don’t do it last minute, in the last couple of weeks before your drawdown period ends. Provide an update on the company how business is going, your cash balance, cash burn. Send all your financials. Refresh and share the cap table. Have a really proactive conversation with a lender.The lender is going to have to take it to their credit committee and get it approved. But usually a one or two-month thing, they’ll oblige. Now, if you’re looking for something like three to six months, or three to nine months, that’s a whole different ball game. That’s basically treating this deal as a new deal. And oftentimes the lenders will still want to comply because they still want your business, but they’re going to underwrite it in the same way they underwrote your first deal. So they’re going to do some real in-depth due diligence. They’re really going to do a big presentation, their credit committee, and they’re going to probably ask for some compensation in the form of maybe a loan extension fee or some more worth in the company. After all, they’re taking more risk, thus more risk than they originally thought they’re going to take and it’s going to be super important that your company is still executing.Typically, when the company asks for an extension, it means actually the company is doing well because they don’t really need the money. So that makes the lender want to participate. But if your company is struggling, and you’re asking for two to six months, be prepared for the lender to say no.If the lender says no on a larger extension, then you can go get another deal put in place or go to your investors and ask for more money.