The best investment a business owner can make is to invest in themselves. Purchase books, go to seminars, get a mentor, these things will help you run a good company. Check out SCORE.org to get free business advice from local professionals.
There is nothing worse to a lender or investor than to see a mismanaged company. It’s usually simple decisions that were made early on which over time compounded and complicated matters to the point where a lender can only shrug and say “sorry but we can’t help you.”
As a factoring company we see many examples of this for instance; having an Uncle be an early investor who has to sign off on every decision but he lives in Miami and the company is located in Chicago, or operating agreements that have a partner involved who has long since left but is technically still an owner of the company.
Definitely just as bad would be a business model that is a hybrid of normal sales procedures like; pre-billing, consignments, customer credits, selling to your own subsidiary or insufficient due diligence on vendors and customers.
One of the most prevalent problems would be, not getting an old lender to release their financing statement on the company collateral. In these days when banks are gobbling each other up, if you have a loan you paid off 15 years ago to bank that no longer exists, there is a fair amount of leg work to get an old UCC-1 terminated. As soon as you pay off a bank loan, ask the lender for a UCC-3 right away.
All this is to say, when it comes to borrowing working capital to improve your business, try to have a clean slate without complex stories and confusing documentation. Your lender will thank you for it.