I’m a broke startup impostor

Sorry to hear that buddy. I'm probably one of those who's reading your blog wishing I could learn something to get to my first success.

Just curious, you mentioned past startup success. Was it not enough to retire on or did you plough everything into this venture? How long have you been working on this venture and in your opinion was it just being too optimistic, or did circumstances just came by that made it difficult for your current venture?

:(

That sucks, but I think realty might force you to take a "normal" job? At least part time?

Seems like you do something right (if people ask you for your advice), so why don't you do consulting? Rates are usually good for consulting.

There are other options as well: Work in the night as taxi driver, rent a room of your house..

Get some contract work or do consulting. Steve Jobs did it. Even Bill Gates did it.

Nothing worth doing is ever easy. You have a great wife that has supported your ambitions and loves you. She has stuck by you even through these tough times. You have your children which i am sure bring you great pleasure. YOU ARE RICH. Money is essential in life but is meaningless without a loving family and friends.

I want to say thank you.

I am not in exactly the same shoes, but not far off either. You took the words right from my mind.

Thank you for writing, thank you for sharing.

First off I also want to thank you for sharing. I feel like I'll be facing this in the next couple of weeks, too.

I just found a neat article online. Maybe you wrote this. If not it might help you: http://www.inc.com/dana-severson/are-you-a-broke-entrepreneur-like-me-here-are-5-options-to-consider.html

Broke is the best thing to experience in so many ways. . . I have a successful company- bootstrapped it to a few $M in revenue this year and still dump every penny back into the business. I'm still broke. But I'm ok with it. In the process of building this thing, my wife and I have been broke, we've been homeless, we've stared down cancer, we've faced bankruptcy, etc. Shit, I funded my initial inventory by saving on the food budget and dumpster diving our food. This is not to engage in some boostrappy bullshit humble bragging, the point of this is that the fact that we've stared into the abyss and seen the bottom a few times means that unless we have to deal with cancer again, while we're homeless and living in our car eating dumpster food, everything else is relatively cool. Actually, we really enjoyed living in our car- some days it would really be a relief to lose it all. It makes you realize that money is the most worthless thing in the world to some extent- money is completely replaceable. My wife is not. I guess I'd encourage you to seek the comfort of context. If you are going to be an entrepreneur your entire family has to be cool with the prospect of losing everything at any time. Once you come to emotional terms with that, the rest is a cakewalk.

I am the OP... not really, but those are my words.

My wife's emails sting deep, and she is right. I have spent a >100K seed round, tried to grow to quick, believed too much, and have been broke (no savings, no investments, no cash, no credit) for nearly 14 months.

I have had massive deals in advanced talks (several $500MM deals with decision makers) to succumb to poor hires and plain industry-luck.

I've found it ridiculously effective to share with my wife (the one that hates risk and failed-words) and to tell her that I'm not in love with the process, and what I've learned and have grown from. She always seems to read from me the sincerity and how grounded I am in my journey for "our family".

I have already come from nothing (very poor child of an immigrant that is still stuck in the drowning of a divorce 30 years later) but that I've had to learn that my level of optimism could do with a little toning down to account for the rest of my commitments in life.

We are entrepreneurs.... we use risk as fuel... we need to focus on the alternative fuel source.

Why can't these girls just chill out? They need to take a mindfulness class

"It was email I had received the day before from the organizer of an event I recently spoke at deciding they weren’t going to pay me." - This really stood out to me and no one else mentioned it in all the comments above.

What the hell happened here? It sounds like you performed a service for them by speaking at their event and now they just decide they are not going to pay you? What kind of bullshit is that, what did you do about it, did you have an agreement or invoice them for the service, and what leverage do you hold to get your money?

If someone hired me to do something, and it was done correctly and well, they cant just not pay..especially if you and your wife depend on the income. I'd sit my ass in their office until they gave me a check to walk out with. Sure they may never do business with you again, but that's OK, you don't want to keep clients like this. Don't let people and clients walk over you, I learned this early on the hard way as I used to want to be nice to everyone and make sure everyone was happy.