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Ask HN: Looking for advice – Failed startup, long term relationship at same time

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Re: Ask HN: Looking for advice – Failed startup, long term relationship at same time

#41
post #39
post #38

I have been there. If you manage to stand back on your feet (and you will) you will be stronger than you ever could imagine. Find your own path and get back in the game. PS: Consider moving to another city.

This! While it sounds weird, moving to another city and getting a fresh start got me out of my dark period (broke up with GF after 7 years, failed startup, completely broke).

Move to Key West.

Re: Ask HN: Looking for advice – Failed startup, long term relationship at same time

#43

Thank you for all of the constructive comments and different perspectives. I saw a few emails in my inbox too. Thank you. As a single founder, it's the constant rejections that have me down. Failure to raise money to prove product market-fit [1]. Failure to come through in the clutch. Failure to convince investors. Failure to get the 'Yes' people to actually give you the cheques they said they would commit. Failure t…

I've been in a place similar to where you're at now. Failed three year long distance relationship, debt, failed business.

I spent the first few months post just rolling around in misery. At some point it became clear I had to make a choice to either get out of it, or just keep being consumed by it. So I did the only thing I know: I went back to building. I built with the goal in mind to see relatively near-term victories, as the prior start-up was a long build and failed with not much to show for it (other than experience). I wanted to start getting back into the winning column in regards to how things were going in my life, even if it was just in little ways, because I knew that would begin to lift my mindset.

When you're ready, you'll probably begin to reboot. That's a process that takes some time, and is obviously different for everyone. Try to find your way through it as quickly as possible, and in as healthy a fashion as you can (find the happy medium). Feel free to be angry, upset, frustrated, depressed, down, the whole cycle of negative emotions, go through it all and flush it all out; don't try to not go through it, you have to go through it.

My suggestion for the next thing you build: have it be something that makes money from early on and requires no outside investors; something that runs on a $40 or $80 linode instance, where you can become cash flow positive with just a customer or a few. Create something where your customers fund you, in other words. No more waiting for investors to say yes. The next time around, when you're ready, you'll say yes to them, if they're lucky.

Re: Ask HN: Looking for advice – Failed startup, long term relationship at same time

#44
post #18

This is a tough one because you mentioned "All of the family and friends money is gone". I wouldn't do a startup with money from people I love or know. It will damage the relationship somewhat permanently. BUT you need to promise them you would pay back. In general: 1. Stick with family 2. Hangout with friends and make more friends 3. Tell yourself: the next woman will make the rest of your life happier than ever 4.…

See narrowrail's comment about equity vs debt. If you take money from family, you should make the risks clear and allow them to decide: equity or debt?

I sympathize with OP's desire to satisfy unsecured debts to the family, but I'm less inclined to cover an equity investment.

Re: Ask HN: Looking for advice – Failed startup, long term relationship at same time

#45
post #17

Hey, drop me a line: balajis at a16z dot com. We try to help entrepreneurs who have an experience like you've had get back on their feet. No promises, but often we can find you a great job at one of our portfolio companies.

Do any VC's provide subsidized (and heavily encouraged) psychologist/therapists to their portfolio companies?

Obviously wouldn't help in this situation, but I've been thinking about this a lot lately. Lots of pressure on founders, and often no one they can really open up and talk to truthfully.

Re: Ask HN: Looking for advice – Failed startup, long term relationship at same time

#46
This happened to me two years ago. We were together for 7 years, and I had just launched my new project and I was getting press for it. This is probably the worst thing that could have happened to it.

It was hard but I kept going and a lot of good things came out of it.

PLEASE PLEASE PLEASE hit me up if you need to talk. dan[at]techendo.com

Re: Ask HN: Looking for advice – Failed startup, long term relationship at same time

#47
post #17

Hey, drop me a line: balajis at a16z dot com. We try to help entrepreneurs who have an experience like you've had get back on their feet. No promises, but often we can find you a great job at one of our portfolio companies.

assuming this applies to developers and doesn't work for marketing/product manager types

I wouldn't assume that, you should reach out to him.

Re: Ask HN: Looking for advice – Failed startup, long term relationship at same time

#48
post #17

Hey, drop me a line: balajis at a16z dot com. We try to help entrepreneurs who have an experience like you've had get back on their feet. No promises, but often we can find you a great job at one of our portfolio companies.

Do any VC's provide subsidized (and heavily encouraged) psychologist/therapists to their portfolio companies? Obviously wouldn't help in this situation, but I've been thinking about this a lot lately. Lots of pressure on founders, and often no one they can really open up and talk to truthfully.

I think it's a great idea and I talked about this a bit here:

https://www.techendo.com/posts/5-things-i-would-do-right-now...

Re: Ask HN: Looking for advice – Failed startup, long term relationship at same time

#49
If you'd not met her 8 years ago, and if you'd not started your startup 2 years ago, you'd be right where you are now but without the sense of loss. You gained something, for a short while, and now you've lost it again.

As for your family and friends, whose money you lost: they can handle it. It's only money. It's to your credit to feel bad, but now you need to work to pay back the money you lost. At least some of it, but hopefully all of it. That would be worth more than any apology or self-abnegating behavior. If you're a software developer and willing to live on raman/at your parents house for a year you will be able to save a huge sum. There is probably no legal obligation to pay it back, but there is a clear ethical and moral obligation - and it will give you a concrete goal to work toward.

Re: Ask HN: Looking for advice – Failed startup, long term relationship at same time

#50
I haven't had a startup fail, but as a freelancer I've had some 'feast' times and some 'famine' times so I relate to feeling haunted by yourself over your decisions.

If you need somebody to talk to, please feel free drop me a line tomhodgins@gmail.com and at the very least I can listen and share in what you're going through.

In the meantime, here's a little perspective trick I learned, there's a phrase in English that we used when something happened that actually works on two layers: "it came to pass".

In 2014 it came to pass that verysadpanda's startup finally breathed it's last. It came to pass that verysadpanda's relationship faltered and came to a close. But it came....TO PASS. It won't always be this way, it's all temporary!

It also came to pass that verysadpanda felt sad, and before long totallyfinepanda came back out again.

Best of luck in the days and weeks ahead, but you're not nearly as alone as you feel :)

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