I am interested in hearing entrepreneurs’ stories about times when they tried to save money and it really cost them. For instance, maybe you tried to do something yourself instead and it really backfired. Or you purposely hired a cheap freelancer and they screwed you over. Anecdotes like this. Share away!
Be Cheap, but not too cheap. If you find a tool that truly makes you more productive, get it, use it. You don't have the expertise to be a lawyer (unless you are one), accounting will consume too much time, and HR is not your core expertise. As Dane said, legal, accounting, HR: get some .
Your job as (what? CEO?, Boss?) is to make sure your workers have the tools and resources to get their job done efficiently. Don't devalue your own time. I've heard entrepreneurs who were proud that they were able to take on so many jobs, like when a toilet overflowed at a company where I worked. I don't clean my office or my rental properties. I don't mow the grass. When I try accounting I get it wrong.
So, be cheap, but not miserly. Choose wisely.
Do not do your own legal. Do not do your own accounting. Get an HR professional fast. The best is to hire, if even part time, a CFO that manages this for you. These three issues will destroy your company if done wrong.
The most expensive mistake I ever made was hiring a cheap engineer.