Shit I Learned Burning through My Family's Life Savings on a Failed Startup

An interesting article, but the title left me with a question that the article completely failed to answer: what about the lesson "don't spend your family's life savings on your startup"?

The author had an invaluable experience, but I think the blog post doesn't do it justice. None of the section headings is actually that surprising; it's unlikely he started a business without being aware of <i>all</i> those lessons in the broad strokes. Be ruthless, yes, but why was he unable to be ruthless even when he knew he should be? "Fail fast"? What did he do that violated that? What was he thinking, failing slowly?<p>I wish he could come up with a way to give us more concrete details that add nuance to the broad lessons. Memories will fade, and if all he's saved of them is this blog post, the lessons will follow the life savings. And <i>that</i> would be tragic.

<p><pre><code> Know when 80% is good enough</code></pre> I consider this an important strategy when executing most tasks. It is an on field guideline in the Marine Corps to aim for a 70% solution to problems in some cases. It is sometimes a better strategy to implement an imperfect plan than to roll out <i>the</i> perfect plan by the time it's too late.

I just read Rework. There is a chapter called "learning from mistakes is overrated." It cites a Harvard business study that showed that startup founders who launched a startup and failed had about the same odds of success in their second startup as someone who was launching their first.<p>While I've learned valuable lessons from my (many) failures it's a nice reminder that there is also a lot to be learned from our successes.

Now I'm curious as to what the startup did.

"The issues that bother you at the beginning will be what kills you later."<p>This section describes a people problem, and I think the headline should be narrowed to that realm. Otherwise, a good, honest list that I believe will ring true to many HN readers.

This is great stuff, kudos to Kevin.<p>The "looks like/is a goose" one reminds me of looking for a "market alternative" (from the book "Crossing the Chasm"). The market alternative is how potential customers <i>presently</i> deal with the problem the new product solves, and it has a name and an existing budget. This helps to communicate what the product is to the customer.<p>If it's hard to find such a market alternative, it's a sign that the product isn't ready to 'cross the chasm' into the mainstream - that is, it won't be attractive to <i>pragmatists</i> (who just want a percentage improvement on existing methods, with minimal change). It's still in the non-mainstream pre-chasm realm populated by <i>techies</i> and <i>visionaries</i> (who think the tech is cool in itself, or who can see a new way to use it to make money, respectively).<p>It might also be that the target market selected isn't suitable, i.e. there might be another application of the technology and for another group of customers, for which there is an existing "market alternative".

So many of these things resonate for me, I'm troubled by a good third of the problems, or the seeds of the problems outlined here. Some sterling advice that I'm going to heed well.<p>I think the nature of the failed startup is irrelevant as much of the advice is raw, yet vague enough to apply to many areas. Almost all startups are based on a good idea, their success or failure rests almost entirely on the back of the choices you make along the way. Thanks for sharing this.

I like the goose metaphor and I see it in education all the time. We constantly tell undergraduates that learning math is not just about crunching numbers but about learning how to abstract and reason more efficiently and yet the tests and homework assignments tell a different story so the undergrads just learn how to crunch numbers.

Never spend more than $1000 in a startup unless you start getting revenues, say $100 or $200 and growing.<p>Then invest proportionally to the revenue.<p>With cheap VPS in the $20 and say $500 in average design, I fail to see how you should over spend in chasing a dream highly probable bound to fail.

"Fail quickly" always annoyed me. The part that annoys me the most is that institutionalized tend to view "I failed to the tune of several million dollars" as validation of somebody's investment worthiness. Sure there are lessons to be learned in failure. More often than not, the lesson seems to be "I learned how to convince VCs to give me money for a bad idea and an incompetent team!"

if it really added 10% to the bottom line, why not take payment on commission?

All I can think when reading this blog post is: Owned.

@Kevin Proud of you dude! Your first time on HN and you made it into the Twitter stream. Glad to have u here in blog land!