Ask HN: What is your technical or business “never again” story?

working with a genius programmer who is arrogant and insulting

I've been burnt recently, the self-hosted proprietary time tracking & invoicing tool I've been using for the last decade has decided they're only supporting their 'cloud' service from January.

Unfortunately, I haven't see any existing OSS options that quite work for me either.

I've dealt with clients that eat up 90 percent of your time while only providing ten percent of the revenue. Never be afraid to fire the client.

I worked with storage arrays at a service firm. The storage arrays backed up to the cloud. They had an onboard proprietary GUI, where if you checked a single box, it would use HTTPS instead of HTTP when transmitting to S3 (no idea why S3 even allows HTTP to start with).

They refused to roll this out (HTTPS) across the 4-5 servers of this brand we managed.

Something just broke in their brain, because I was coming at it from a security angle, they thought “this must be a waste of time / I am a power-hungry sysadmin resistant to change”. I still think about it to this day, and will get anxiety every now and then suggesting a mildly taxing security fix, because if ppl can say no to HTTPS checkboxes will they agree to anything?

I used to sell grey market designer drugs. jumping thru hoops to be able to accept credit cards for such transactions is totally not worth it. I had so many chargebacks that were impossible to fight... some of them were $1000 orders. stick to Bitcoin or litecoin for your shady business ventures.

FB ads when you don't really have enough money for a marketing budget anyways. FB ads is really a money game, the more money you spent, the more likely your ads will get conversion.

Letting a Rude and Insulting client stay on for longer than we should have. Never again our company will deal with a Rude/Insulting client no matter how much they are paying. Rude = Fired. Be nice. And I am not a snowflake. I can deal with tough clients but not rude/insulting/entitled ones.

Joined a company as a very early employee. The company became successful (200+ employees, mid 8 figures revenues), but founders just won't sell it: instead of humbly admitting the luck we had (it's always about luck, I was in the front row seat the whole time so I can definitely and objectively state it) and take risk off the table, they are doubling down trying to make it much bigger (targeting mid 9 figures revenues, and they just took a HUGE investment round with a stellar valuation, which essentially prices us at beyond-perfect execution, so it's significantly risky). In the meantime, I am completely burned out and would just like to put an end to this adventure which lasted 5+ years, but I can't.

I can't leave due to my stock options otherwise expiring (standard 90 days window), and I don't want to put the liquidity necessary to exercise them and leave, too risky due to the appreciation of those shares, nor I want to take out a loan or stuff like esofund which will eat into 50% of my profits, and would still leave me with a taxable event if the company went belly up and the loan was forgiven. So, I'm a typical example of "golden handcuffed".

So, my "never again": never again work for founders who are already rich and are not looking for a reasonably early exit in case of success. My fault for not checking during the interview process, but I was young and naive.

If the founders were not already extremely affluent, I could assure you they would have already sold the company by now (probably at the 2-3 years mark), very likely realizing low 8 figures profits for themselves (and low 7 figures profits for me), whereas they are now shooting for high 8/low 9 figures for themselves, "hurting" me by exposing me to insane time cost opportunity, and also making the whole thing much riskier since as you grow your acquirer pool shrinks dramatically.

Realistically, I end up being a rest and vest employee, meaning I don't do much work these days, and I likely won't get fired since I have so much context, so I spend a lot of my working time avoiding getting burned out and mostly learning about new technologies, but it's still much less than ideal and it's hurting both me and the company.

At the same time, my emotions these days are very weird and nothing I ever thought I would ever experience: I am usually equally happy if the announced quarter results are a big win (meaning my equity valuation is preserved) or a big loss (meaning we are approaching the end of this company so I'll be free without having to voluntarily forfeit a potentially large payout).

If you inherit a large code base that is badly written AND you are planning to stick around in that company. I would strongly suggest to immediately start re-writing that legacy code even if you have to burn extra hours. Otherwise you would be doing nothing but firefighting in that job with limited control over your situation.

1.) accepting angle funds for too much equity (45%) and not "quitting my day job" to focus full time on my venture.

2.) Paying (a lot, $35K) a high end IP law firm to "finish" two patents I'd drafted an file them. I now write and file my own patents for next to nothing; it just takes time.

3.) Letting a law firm convince me to pay even more ($40K) for foreign patents, which are pretty much worthless unless you're an Apple or Samsung.

4.) Not getting an up front firm quote for legal work (said firm tried to collect an additional $90K, which of course we did not pay).

5.) Not watching the company bank account like a hawk to make sure my partners weren't wasting precious raised capital on worthless overhead expenses (e.g. empty offices... and they were).

Oh, the list goes on...

Never will I use, stay on a team that uses, or assist any client which uses zip ties for cable management.

Anyone that says "we will just do this temprarily" will get charged double and need to send that statement in writing with firm start and end dates along with the consequence of not meeting the deadline.

Once your average deal size hits >$250k touch nothing less than $100k if it's a new client, leave it to inside sales.

If someone (or a business) has ever paid you for anything they never get free work. Free product? Maybe, but never free work.

Put it in a contract, regardless if buying or selling, or it doesn't exist. When asked to modify something on the fly from that contract, "we'll let you know" is the only acceptable answer until you review with your team.

"I don't know but will try to find out" is acceptable. "Yes if..." is preferred.

"No." Can help you live longer and healthier.

My "Never again" business/ people lesson is to avoid anyone with toxic nature be a part of a startup team, howsoever genius that person might be. Once bitten, twice shy about this.

For a Startup, destination obviously matters, but making the journey enjoyable should be one of the top priorities.