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Behind the curve on technology-while some people will think this is an advantage to a buyer to do things more efficiently in reality there is a cost to hardware, software and implementation. Use your experience of your business to get technology up-to-speed, show increased efficiencies (and profits) and sell for a higher price.
Skimming cash-there isn’t a CPA around who will let a buyer be convinced to pay a price based on unreported cash. First, you are cheating the IRS. Second, is it worse that you’re skimming or worse that you say you are but really aren’t?
Too small-a business doing $2,000,000 in sales will not get the same multiple of profits as a similar business doing $20,000,000. There’s just more risk factors the smaller the business is. An issue that is a major disruption to a small firm is a minor hiccup to a larger firm.
You are blending too many personal expenses into the business-yes; there are advantages to paying for things with pre-tax dollars instead of after-tax dollars like employees have to. Carry it too far and it’s almost as bad as skimming. Bottom line, buyers and banks like to see profits. Show a lot of profit, pay some tax and it will come back to you in multiples when you sell (and make it easier to sell and finance the business).
You have to work too hard in the business-buyers look for businesses they can work on not work in. They may not have your passion for your product or service; instead they have business skills to leverage what you’ve done. Get out of the business of doing things an employee could do.

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