I second the Bench recommendation. I did my own books for 5 years, had a VA use a (homebrew) single-entry system for about 3, and did Bench the last ~2. Bench beats the snot out of the earlier methods.
On the topic of "How conversant do you want to be with bookkeeping as a business operator?": there is zero value in having you, personally, write up that you spent $4.76 on a coffee at Starbucks. That is an actual thing your business requires someone to do; it should not be you.
Should you know what double-entry books are? I think you can safely pass that off as "implementation detail."
Should you know how to read a balance sheet and income statement? Yes. That's a really critical job function. Are some of the individual entries a little opaque if you know nothing about bookkeeping? Possibly. Member Contribution / Member Drawing come to mind.
There are some less-bookkeeping more-accounting topics which I think software entrepreneurs would be well-served by being better at. "Revenue recognition for SaaS businesses" is a decently good example. I see that bite smart people all the time.
Boy howdy, being down voted into oblivion for a pretty un-nuanced comment on my part. Oops.
More nuance:
I have a MBA, which taught me bookkeeping (cash vs. accrual, double-entry, basic financial statements - the CRUD of accounting) and lots of strategic financing.
Have bootstrapped/VC-financed a couple of firms - having an understanding of double-entry bookkeeping, and how to construct financial statements is/was not particularly helpful. None of those businesses went away because I did - or didn't - perform basic bookkeeping, or could/couldn't read a income statement.
At a very small scale (which is what this article is talking about) almost anyone can read a income statement and balance sheet without a strong bookkeeping fundamentals background. Yes, you can't construct said docs, but you really shouldn't anyway (that's what the bookkeepers ought to do).
Strategic finance, however, is much much more valuable, which this series doesn't really get into.
I'd argue that outsourcing basic bookkeeping then hiring a fractional CFO to help you with strategic financing is far better use of your time than spending 5, 10, or 40 hours internalizing that a new vendor invoice in accounts payable is a credit to a liability account.
Can you elaborate about how revenue recognition has bitten smart people? I wasn't familiar with the term until you mentioned it but I think I have a handle on it now.
I'm guessing an example would be counting a prepaid yearly plan signup as the full year's revenue immediately instead of only counting it as revenue a month at a time as the service is delivered.
Your example is a good one. Another example would be if you have 99.99% up-time guarantee, but don't provide it and have to provide refunds or discounts.
Groupon had troubles with revenue recognition. When it sold the coupons, it would count the full coupon as revenue even though 50% belonged to the merchant.
Oil producers have to pipe the oil to a refinery. The oil producer actually sells the barrel of oil to the pipeline and buys it back on the other end. Then the oil producers takes that barrel and sells it to the refiner. The oil producer has sold that 1 barrel twice.
However, as patio11 mentions, this isn't basic bookkeeping.
On the topic of "How conversant do you want to be with bookkeeping as a business operator?": there is zero value in having you, personally, write up that you spent $4.76 on a coffee at Starbucks. That is an actual thing your business requires someone to do; it should not be you.
Should you know what double-entry books are? I think you can safely pass that off as "implementation detail."
Should you know how to read a balance sheet and income statement? Yes. That's a really critical job function. Are some of the individual entries a little opaque if you know nothing about bookkeeping? Possibly. Member Contribution / Member Drawing come to mind.
There are some less-bookkeeping more-accounting topics which I think software entrepreneurs would be well-served by being better at. "Revenue recognition for SaaS businesses" is a decently good example. I see that bite smart people all the time.