This restaurant owner came from Japan with his wife when they were in their twenties. They both spoke limited English and settled down in a part of New York that is predominantly Caucasian. For many years, he worked as a dishwasher while saving up diligently.
When he saved up enough money, he entered into a partnership with 2 others to open up a restaurant. One of the partners screwed the other two and he had to declare bankruptcy.
He went back to being a dishwasher, then later a cook, as he saved up money again. Finally, he had a chance to purchase a hole-in-the-wall restaurant that he thought he could improve. Unfortunately, that one also failed. And he declared bankruptcy for a second time.
That still didn't deter him. He worked again, saved up again, and opened up his third restaurant, a sushi restaurant. And for him, the third time was the charm.
This one became a success. It grew to 3 locations total. Every morning, he drove for hours to the fish market at 4am to select the best fish, then transported it to his restaurants in the back of his truck. He still has that truck. We all called it his "fishmobile" because it stunk of fish like you wouldn't believe.
He didn't reach this success until his 50s. Through it all, his wife was amazingly supportive. She worked alongside him in these restaurants too. They are retired now. He shared his story with me when I told him I was starting a business of my own.
I can't imagine having to lose so much, but in his perspective, he started out with nothing, so it wasn't that painful to return to nothing. I'm not saying I would want to do this with my wife and daughter, but hearing his story definitely gave me perspective.
There's a certain "thing" I've found in some people.
This thing is an abiding, unquestioning (or nearly so) drive. They are very matter-of-fact and don't appear to spend a lot of time questioning "why me?" or reaffirming to themselves that life is difficult. They just...do. And they keep on doing. Whatever needs to be done. I'm not saying that it's easy for them. But, they seem to naturally possess a certain focus and efficiency about life and their objectives. In so approaching life, I think they tend to manifest more.
This may run somewhat along cultural lines, but I've seen it in various people, including my own family members in previous generations. They put their noses to the grindstone through very difficult times and never looked up until they achieved their goals. I sincerely do not recall hearing them complain. Ever.
I've often thought that I would do well to be more like them; spending less time in "meta"-mode engaged in a running mental commentary about what I'm doing, and more time just doing.
"One of the partners screwed the other two and he had to declare bankruptcy."
"Unfortunately, that one also failed. And he declared bankruptcy for a second time."
Have you ever held large accounts receivable and had a customer file for bankruptcy? I have.
Not everything is "startup lottery" using investors money to spread around the risk so really nobody gets hurt (in the way I am illustrating I mean).
Edit: The losers in bankruptcy (in addition to the one filing bankruptcy) are the creditors. I'm not talking about Bank of America but the vendors that sell you food or the electrician who did work for you or the guy who sold furniture to you. Not knowing the specifics I don't know exactly who was hurt but there was most certainly someone who extended credit in good faith and lost something that now has to work harder to make up the money that they lost. (IN theory at least.)
"For two days, I tried to find the right time to tell her. I kept finding reasons to wait. Finally, on the third morning, I said “we need to talk”. Apparently, those four words mean something else entirely to women, which kind of worked in my favor. Having said that, it also set the wrong tone for the discussion, so I’d would advise others against that approach."
As a married man, this made me laugh.
My first reaction was "oh god you didn't, son...".
Two genders separated by a common language....
Curious - what does an unsupportive investor look like in these moments? Do they throw a fit? Act passive/aggressively? Badmouth you?
Honestly I'm a bit bummed to read this. I assumed that in these moments investors are almost universally supportive or at least understanding.
Dude. You went all in and are now broke. You were responsible to them.
Don't spend one remaining second of your life feeling bad about that shit.
Why not? The fact that you tried and failed means that you learned something -- which makes you a better founder than someone who has neither tried nor failed. This experience will make you a better founder next time you try.
You just earned an MBA. This MBA, like any MBA from a top university, is expensive. Except yours is much better. It is based on real-world learnings, learnings that you could have never gotten from a classroom. Arguably, a traditional MBA would have never given you the right background for creating a startup too. So your experience is even better.
Very few get to go through an accelerator, and the fact that you went through a well-known one means your education is even more precious. So congrats on a fantastic, though tough, learning experience!
At least for myself, I'm not really celebrating the failure, I'm celebrating the bravery that led to them trying, the strength that it took to persist, and the honesty it took to admit and own the failure.
But failure sucks, so I think it's worth being unsubtle and countering the feeling of failure with something that feels pretty positive.
"It's a dangerous business, Frodo, going out your door. You step onto the road, and if you don't keep your feet, there's no knowing where you might be swept off to."
Sounds like the author hasn't entirely bought into that notion.
Anecdotally, each person I've know who did this - put their dream on hold for their spouse as opposed to fully accepting the idea themselves - ended up extremely bitter about it.
I don't know if you read his previous post, but the guy was in pretty dire straits.
There's a big difference between putting something permanently on hold and never trying versus trying, failing, and then putting them on hold.
I don't think he'll be bitter because he tried this time. Maybe after some time he (and his family) will be ready to try again.
This sentence bothers me. How is it possible to not know if you're personally responsible for debts?
I've taken some (calculated) risks quickly so as to avoid hand-wringing over details. Not so big as understanding if I'm personally liable for something, but I could easily believe people building a fast growing startup would.
On both counts, I would say don't worry about it. There's significant asymmetry in the debt-vs-debtor relationship  and you should feel about as much personal responsibility to them as they have to you -- ie, none. For both equity holders and debt holders, they are compensated for the risk they take. They will prey on your feelings of personal responsibility to try to get you to repay them, but if you've filed for bankruptcy and tied things up neatly (I'm not a lawyer), then you should walk away cleanly.
Note that I'm not saying "screw your equity and debt holders", I'm just saying that once the entity(ies) in which equity and debt was held has folded, you need to walk away.
 Excluding if you signed personally for debts
 See: housing crash
In the long term, I am for fixing such problems if possible, of course. This reminds me of https://news.ycombinator.com/item?id=7186407