Ask HN: Why did your startup fail and what did you learn?

Running out of money. We were bootstrapped, and the style of work we were doing had some decent capital costs. We failed for a "bargain" (less than 7K), but we had cut to the bone and deeper while trying that. Side jobs to make rent just increased stress and distracted from the business.

Why did we run out of money?

Focused on engineering instead of sales and marketing. Manually spinning up servers would've been the right thing to do--since we instead were both technical we solved technical problems and kinda missed the people side of things. It was real and hard work, but it was not work that was relevant to making sales.

After we ran out of money, why didn't we keep at it?

Stress blocked further work. Too much stress led to neither founder being able to even think about the company and its business without severe anxiety. Times were dark and bad.

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I learned that you want to prioritize the money funnel over literally every other thing that you as an engineer think matters. Coffee is for closers.

I learned to try out only with other people's money. Don't put your rent and basic living on the line for an idea if you aren't comfortable with what that can entail.

Probably most importantly, I learned that the glorification of the startup lifestyle is a lie perpetuated by people seeking to make money from it at all levels. Nowadays, even the glorification of failure and celebration of mental health seems to be by people looking to advertise their businesses, cure-alls, or just get internet famous.

It's rotten to its bloody core, and unlike finance doesn't even pay well.

We built a software platform that intended to automate the job of market researchers. Those researchers we hoped to replace ended up finding the tool itself useful. Since the platform didn't replace the employees, our pricing model fell short. In the end, we found success by hiring our own market researchers and effectively pivoting into a software-driven consultancy. Profitability came slow and steady.

After months of profitable growth, things changed on a dime. Our lead investor effectively unseated the CEO one day, and made the statement that we were doubling down on the original SaaS vision. Within a month our 100 person company had been reduced to around 60. The now-unneeded consulting staff were recipients of strategic layoffs. Revenue dropped overnight.

The morale of the company also fell off a cliff. The C's lost their ability to cheer up the team and the senior staff saw the holes in the boat and promptly abandoned ship. The company folded about 1.5 years later for a fraction of the initial investment.

My learning in all of this: the tales you hear about the "bad VC"s are occasionally very real. Make sure when bringing on investors that they align philosophically with your founders' vision. Make sure that philosophy is deeper than "we want to make that cash". Great investors i've worked with since can be an immeasurable resource in so many ways. It is absolutely critical that founders be excellent in their courting of valued investors. Similarly, they must be ruthless in their rejection of the bad ones, however sweet the check may appear.

- Their own 'highly matrixed' organizational structure makes it near impossible to find 'the correct person' to talk to about accounting issues, let alone get a straight answer out of them - so chasing these issues down becomes a huge drag on your time and energy and you may very well just give up after a while

- Past-due invoices are typically penalized with tiny interest percentages [in the - They know full well that you, the small company, probably aren't willing to put up the massive time and dollar resources in order to sue them, the big company, for what is to them small potatoes. They have a bench full of experienced attorneys, you might have a single one, and they know exactly how to extend and complicate a legal process such that the litigation itself costs you far more than the outstanding AR.