Top Mistakes and Learnings from My Startup: Postmortem Samsamia

> Startup pressure can bring out the true character of a person

Not necessarily. It can bring out the worse.

Let's say you are stressing a machine beyond its limit. The risks are specified in the manual but you still do it. The resulting mechanical damage can't be blamed on the manufacturer.

My experience is the reverse: I started a company with my 10+ years best friend, and it has been great. We even hauled another friend on board (he bought some shares, but we still have most of them).

Most people I know complain that they don't see enough of their friends due to increasing family commitments, but I'm spending most of my working time in the office having fun with my best friends. It's absolutely great and all the shared experiences also nurture the friendship.

I guess it all boils down to being really really honest about your assessment of each other's character. I couldn't have done it with most of my other friends. We also wrote out rules up front about all kinds of possible issues and determined who would arbitrate, so that we would have clarity before everyone is entrenched in a POV that coincides with their interest.

And our #1 rule is: if anything bothers you, you have to be explicit about it or accept your grievances will be ignored.

I started a company and brought on a best friend about 2.5 years in. It was a terrible and costly mistake. The business continues to thrive, but our growth was considerably stunted for the year he was on board.

I have a few theories for why it didn't work. I think it comes down to an expectation that, as a friend, normal work rules do not apply. This friend thought they could work on whatever was interesting (rather than what their job called for), and could flake or complain as a friend.

Perhaps a more domineering personality than myself could crack-the-whip and force a person into their role, but then what's the point of the person being a friend? And is that a good use of a founder's time and energy? Arguing with and controlling a friend/employee? Nope.

I have had much better luck hiring people I don't know and becoming their friend through work.

"Startup pressure can bring out the true character of a person. The problem though is that you may not know the true character of someone until startup pressure is applied -- even if that someone is your best friend."

This is true enough, but it need not be 'startup pressure' that reveals character. Many life situations can apply the same or greater quantum of pressure. So if you are going to do stressful startups with a friend, see if you have gone through hell before and come out on the other side still friends.

Tangentially life crises are very revealing of who your true friends are. Likewise romantic partners. When you are going through hell, just look around to see who is still there, and who ran for the hills.

I had a similar experience, unfortunately. Call it pressure to establish, call it stress... the friendship was ruined. Thankfully, we did not even start, but we were about to.

I would also argue that starting with a distant family member is also not ideal.

I dunno about true character, maybe levels of maturity. Learning patience and dealing with stress comes with age. Anyone can do it.

Can someone with historical experience starting a company with both a friend and a nonfriend comment about this?

We get a lot of advice (e.g. pg) to start a company with friends, but we also get a lot of comments one way or the other, but without personal experience in both.

Can someone who have been on both sides talk about it? I certainly have not been on both sides.

Sometimes the friendship is worth preserving in favor of going into business with someone else that if you lose, no big deal.

Give him a break, it's obvious that English is not his first language. The article is about mistake and learning about his startup, but you have moved the topic to his style of writing. Seriously, you do realize HN is worldwide right and many of us don't speak English as first languages?

I really appreciate any post-mortem like this, so I don't want to be too critical. But the document itself helps demonstrate one of the reasons for failure: poor user focus.

The faux-academic-paper style looks cool, but is a clearly worse reading experience. It's tolerable on a big screen. But on a small laptop it requires pointlessly scrolling up and down. On mobile, it's much worse.

A lesson declared in the document is "too slow iterating". But I think that's a symptom. I think the real lesson is that instead of building to the founder's vision of what's cool, you have to build for actual people and their actual needs. To do that well, you of course have test your hypotheses, which requires iteration. But the iteration itself is secondary; building the founder's fantasy iteratively can fail just at thoroughly as building it in one long go. Either way, it's self indulgence.

I'd say the blog format has the same build-what-I-think-is-cool flaw. It's more excusable in a personal website, of course. But I hope he learns this lesson before his next startup.

Yip yip. It’s called “top-down” communication and every good newspaper does it exactly like you describe

That is the academic style! The academic style is effective communication, the problem is there's a lot of bad essays.

Maybe it's because I'm reading so many, but it feels like ICO whitepapers have helped revive this style too...

This is so important, it's concerning to think about how many good years of smart people have been wasted. It should be taught in school.

how much did he sell you his shares for, if you don't mind me asking? because it sounded like it's for the first company, not the new one

Or when you run out of cash.

How is that incompatible? If you partner with a crook, can't you take a responsibility for making that mistake (of not seeing the signs) but still call the other person out for being a crook?

Taking responsibility is different from saying other did no wrong.

> everything that follows is how his co-founder screwed him

No. It's the part that takes up the most space, but there are a number of other, perfectly useful conclusions, like "you need a product and customers, not a technology", and "adapting to customer needs brings you succees".

I was going to simply quote:

> I, not my cofounder and ex-best friend Miguel Angel Maldonado, was to blame

and note: “this is not apparently something the author actually believes”!

I put some of that down to him not writing in his native language - perhaps it is more difficult for him to translate feelings or concepts to English.

But I do agree that it would have been better to hear about some of his own failings or bad decisions. Hard to imagine his co-founder would try to eject him from the company without at least some perception of an issue with his character, skills or decisions.

https://github.com/miguelgfierro/sciblog - Looks pretty sweet!

If one is sufficiently skilled, consulting pays much better in the short term and carries almost no risk. Building a product pays negatively (costs money in the form of expenses and investment) in the short term, and is very risky (the product may or may not actually get built, even if it does it may or may not fit the market, even if that happens, it may or may not generate sufficient revenues, and then there’s the risk of the company going out of operations due to internal/external problems). The founder that wrote the article this comment thread is discussing stumbled at the final stage - company went out of ops due to internal problems.

As someone that has done both, you might be right. Consulting is way more profitable, but the thing is that you basically are working for someone else, and you can scale it as far as you can fit it on your calendar or hiring.

But with a product you can sell 1,000% of what you had yesterday, the schedules might be a little tight since B2B expects at least a few sales meetings.

So it has its pros and cons. And from my experience (and other's, both friends and clients who want to create something), it's unlikely to have something sellable in 3 months.

Accenture and PwC et al show there's unicorns in consulting, but not many.

There's also the in-between/both approach - Oracle and Salesforce are both "Here buy our shit!", followed up very quickly with "Here, you need our services department and a support contract to make that shit work".

I guess you should ask yourself is business success worth the risk of your relationship failing?

Jessica Livingston and Paul Graham seem to have done okay with that route.

What, why?