Ask HN: Practical finance/risk books for small businesses

i ran a successful small business for 12 years. in my opinion, you must learn by doing. it's scary but you have to do it. the problem is every business is a unique snowflake and you're not going to find much general advice other than "buy insurance" or "outsource your payroll and HR."

one strategy i used was to sit down and think of all the things that could possibly go wrong with your business or a specific project, and google for solutions that can help you with that. work backwards from the problem. it's like designing a resilient software or systems architecture.

you're going to read a LOT of federal and local laws, accounting rules, insurance regulations, speak to a bunch of different solutions vendors, and wade through a bunch of bullshit before you find the one nugget of information you need.

you also need to be generally savvy about how to deal with money and people. naive people don't make it very far.

“Risk management” involves nuanced trade-offs that are often specific to the business/owner/clients triad. Rarely there is a clear option that is strictly better, otherwise there wouldn’t exist options, and to know the subtleties of each requires expertise that you will not obtain given the complexities of law/finance/tax/compliance. The internet is not a good source of information because this is not a general interest topic and the wisdom of the crowds rarely applies.

For most effective outcomes, your best strategy is to spend the same time on generating/increasing revenue, and using a portion of the surplus to hire experts to protect you. Doing risk management ahead or instead of value creation misses the point of business.

I recommend the book Business Planning: Closely Held Enterprises by Dwight Drake though it is not targeting finance and risk management directly, more of the legal framework around business planning, succession, business protection estate planning etc. it was a required MBA reading more than 10 years ago.

https://www.amazon.com/Business-Planning-Enterprises-America...

The best risk management for a small business is a legal structure that makes it easy to avoid holding more than $250k in the business. Because lawsuits. Talk to your lawyer. Though of course a business can still be small and unable to avoid this.

The second best strategy is to disperse accounts. Talk to your accountant.

And talk to your banker.

Rolling your own solution based on internet advice probably isn't the worst approach, but it could be in the running.

Good luck.

Doubt if any risk management book would cover bank failure for small businesses.