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Ask HN: Looking for advice – Failed startup, long term relationship at same time
82 points by verysadpanda on June 28, 2014 | hide | past | web | favorite | 54 comments
Spent the last 12 months on a startup that's basically failed and over the last 2 months fallen into a dark and lonely place. I'm typically an upbeat and positive person, but this failure has taken a bit of a toll. All of the family and friends money is gone. I feel guilty. I'm in tons of debt and have constant waves of disbelief at how I actually got into this spot. Especially as it's all self-inflicted.

Adding another layer, my long term relationship with my gf just ended. We were together for 8 years.

Looking for advice from other founders that have gone through some dark days. Preferably over email or IM

I was there a couple of years ago borrowed a bunch of money(some from my younger brother) and started a company. failed at that and a relationship of 10 years ended. It's time for you to do some serious soul searching. I have a job now. Of course their laying off a bunch of people including me. I'm about to get married to someone else. I have a 9 mo. old son. Still haven't figured what to do about the whole debt thing. But, you're kind of lucky in a way. Your going to survive. pick your self back up. and when you do you'll realize most of the bullshit is just bullshit. Credit's just a number. people come and go in your life appreciate the time you had with them. I remember something Donald Trump said when his company blew up. He saw a homeless guy on the street and looked at him and thought "I'm 900 million dollars poorer than that guy." Also, got a fortune cookie the other day that said "Failure is not defect until you stop trying". I kept it and put it in my wallet.

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 feel like one of the most important things I do as an angel investor is founder therapy to the point that I have thought about taking a class.

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


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.

Founder -> Product Manager is probably the only way I've seen which produces good PMs for startups. Startup PM is totally different from PM in a big organization with great process and resources.

The company I now work for (CloudFlare) seems to have 100% of the PMs come from startups (including me), either from acquisitions or direct hire. It works really well.

We're also looking for a head of marketing. Email me (rdl@cloudflare.com) if you're interested, although I'd also strongly recommend balajis.

Hey - this happened to me. Startup (www.buildinghero.com) and long-term relationship (5 years) both ended in fall 2013. Feel free to email me at thomas.vladeck@gmail.com. Definitely the hardest couple of months scrambling to get over both. I was homeless, heartbroken, broke, and unemployed all at the same time. But I did get over it and so can you! Would love to talk.

Remember that deep down, you are not your past failures, you are not your net worth, and you are not your past relationships. They influence you, sure. But they're not you. The only thing that matters is what you do tomorrow, and then what you do the tomorrows after that.

Best of luck. We're all pulling for you to kick some ass in your next venture.

I'm not sure if this will help or not, but this is my story of failure: http://christopherbull.name/2014/06/19/three-years/

Feel free to email me, can be found through my blog. It sucks and is crushing, there's no way around that. Things get better though, often this can be like being set free - it certainly was for me.

My advice - though my situation wasn't anywhere near as complex so I'm not going to pretend to fully understand what you're going through - is to reach out to your friends and move forward somehow, whether that's into exercise, a new job, or something similar. Find something to keep yourself busy and people who will do the same.

Also, remember one important thing, even if you don't quite believe it right now: You're going to be OK.

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 to "find a way". Failure at home. Failure at simple tasks like cooking an egg omelette for breakfast. Failure everywhere.

It feels like everything is compounding. I can't close anything to save my life. Literally. Confidence lost, swagger extinct. I try to shake off the negative thoughts and 'push through' as every successful person claims.. but somehow, someone pulls another rug out from under me. When it rains, it fucking pours. It could be worse, but it feels like i'm standing in a nimbus cloud that wont let up.

[1] - Don't need to raise to prove product market fit. But haven't pulled a salary in 8 months. Needed to keep the lights on at home. Avoided taking on contract work as that would take away from the startup, so kept pushing thru. "I'll just raise, I'll find a way.." said every startup founder.

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.

The best thing I can tell you now is get yourself a job. Things will pick back up, from there. You need something to pick up your self-esteem, re-build confidence. In my mind a job is the best way to do that.

Slowly pay back your friends and family with the money you earn from your job. you'll feel better about yourself.

Email me if you want to talk. zack at codemy dot net

This is at least the 2nd mention of "paying back friends and family." Typically, F&F capital is for equity, not a debt, so paying back doesn't make much sense. I'd focus on real debts first. F&F investors would not be asking for just their orginal investment back if the company had been successful, so sharing the loss makes sense.

Get some professional help!

Seriously. This reads like full halt in your life and different kinds of debt, which means "brakes" on your future life for a while. With hard consequences for your psyche.

It's not a shame to get someone, who basically tries to get you back on track. You can get someone like this via your insurance, which is seriously interested in you not "producing costs", because of your pretty sick self, in future. I recommend people with psychology background also offering some kind of Coaching or Supervision.

After you are standing straight again, pin that somewhere:

  Ever tried.
  Ever failed.
  No matter.
  Try again.
  Fail again.
  Fail better.
(S. Beckett)

verysadpanda: You may be feeling low right now, but believe it, the low feeling will go away and things will get better. If you are at the bottom of the barrel, the only way you can go is up.

Most founders of companies that are successful -- not the five star Googles and Facebooks and Microsofts, but the dark matter companies that you never hear of, but are very prosperous and do cool things -- tried several times before they succeeded at one of their ideas. Being successful is not just doing work. There is quite a bit of luck (non-determinism) involved. Many good engineers are not successful at everything. You had the confidence to try it.

Look back at your life, at something difficult that happened some years ago. You may have regretted it at that time, but you may not regret it now because it led you in another way to something better. These are stepping stones. Life will not be satisfying if there is nothing bitter in it. The more bitter, the better I say! Everybody has ups and downs. It's how we deal with them that sets one apart from the other.

When you're older and you look back at life, you will think about all of these. It won't be about how much money you made or lost, but about all the people you met, all the interesting things you did, all the fun you had.

I had a very rough patch maybe about 11 years ago for 3 or 4 months. I don't want to go into detail, but one bad thing after another happened in rapid succession. I lost my business of nearly 5 years at the end of it. Like verysadpanda said....I couldn't believe it. Everyone told me... "hey cheer up, things will get better". All except one friend who was a bit of a dark cynic. I think about his comment from time to time.. one of those that really sticks with you.... "It can pretty always get worse" he said with a completely non-sympathetic smirk. And I'll be darned if he wasn't right. It did get worse. I got really sick.

Strangely, this comment stuck with me and seems to help when I am going through rough patches. "Cheer up and look on the bright side... things will get better!" doesn't help one bit, I don't feel it, and at the moment it is scarcely believable. It just makes me feel worse and is in my opinion, useless lip flapping designed to make the person saying it feel better. Meanwhile thinking about what hasn't gone wrong yet but could really does seem to bring a bit of perspective. And motivation.

For whatever it's worth.

Been here. It's the pits.

The more I see these kinds of posts (and I'm seeing them a lot lately), the more I think we need a community specifically for this stuff. Where we talk about the difficulties of entrepreneurship, and how terrible it gets. Where you must be this damaged to enter.

Because frankly, I don't think HN itself is the right place to talk about how many times I've tied a noose.

If I had more time I would start something like this.

Exactly this. It's terribly demoralizing to go through the bs associated with a job search after a failed startup. I would be happy to start something up with one or more cofounders.

What we need is a job placement service for (temporarily) failed entrepreneurs, a support network, and possible more.

Entrepreneurship is like parenthood. It takes doing it to know what it's like, and it's very harsh when there's little to no support.

People who have the guts to start something and have something (scars included) to show have initiative, drive, ambition. They should have no problem finding jobs, support and whatever resource they need.

As with all personal advice, all I can offer is my perspective, so take from it what you can and ignore the rest.

In life, we move through multiple contexts that support us: Friends, family, relationships, careers, intellectual movements, social clubs, et cetera. Typically, when we fail in one of these contexts, we can rely on our success in the other areas to sort of "justify" or "rationalize" our experience. We say -- my family life has suffered, but it was necessary to achieve the career success I have purposefully sought. Or, we say -- my career is taking off, so I need to abandon old friends and move on to a higher caliber of social groups. Thus, we can say our psychological stability relies on the breadth of our "support network" -- any one node can fail, but if we've led a balanced life, we can rely on the others to see us through.

What you're going through is the worst sort of crisis; when multiple nodes fail at once. Specifically, in regards to women, I have seen this pattern over and over again -- a relationship built on a particular arrangement of perceived success, ultimately, boils down to building your foundation on a house of cards.

There's good news out of all of this. You have two useful interpretations of what happened here: Find a woman who will stick by you through good times and bad; or let go of the notion that a single woman can be a support network at all. I am currently struggling with this dilemma in my personal life, but I have seen examples of success with both.

Regardless of the shape of your own support network, there is one particular node I've found that remains stronger and constant than all of the others: My personal relationship with God. YMMV.

Edit: If you're in the bay area, I'm here for another week or so. Feel free to reach out. Email's in profile.

Yeah, unfortunately i've neglected most of my friendships b/c of the startup.

GF breakup isn't a result of startup failure, but more around our long term goals - children.

Appreciate your perspective, thanks

I suspect it was more correlated than you think, but you know her better.

I feel ya. I lost my job, got cheated on in both my long term relationship in which we had moved in together for, and so I also lost my place and my furniture and had to move back in with my dad... twice now... starting every thing over from scratch sucks dude. You feel super shitty and bad about yourself and then you end up taking shitty stressful jobs out of depression. I turned 27 this year and I was sleeping in my old bunk bed for months and months. I'm just thankful I have my dad and I actually asked him for help. I have a few workplace friends at my new job, none close or anything, its just nice to talk to them about things unrelated to how depressing life is. That and not moving in together with an SO when you're in your 20s is the only life advice I got. People always give me the global perspective bs: "At least you weren't born in Syria right now..." or what have you... but that doesn't help much, eh?

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 :)

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.

That's not how capitalism works. You share the upside, you share the downside too.

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” - Teddy Roosevelt

...now pick yourself up and try again.

This might help:


Also, you'll need to put a contact email address in the 'about' section of your profile so people can contact you.

thanks for that link

Use your experience to do another startup, but avoid doing things which led to startup failure. The worst thing you could do is give up. Also try to find investors first instead of spending family money on first business.

Are you sure that's the best advice? I can't be certain, but I would advise some stability (get a good job for a while) and then another startup only if that's what the OP wants.

"Never give up" makes a great saying, but it's terrible advice because the scope is completely undefined. Never give up on what? A particular startup idea, the idea of having a successful startup, or perhaps just working in the tech industry? Some things are really good to give up on and move on from.

I meant not to fall into alcoholism/other addiction and depression.

Rock bottom always enables you to re-invent yourself. Take it as an opportunity to figure out more about family and other non-startup things about life. Work out what were your weaknesses, it will take time and be okay with that.

For me the first time fuck up (which was epic level, startup that I was working in crashed the middle of the recession) taught me that I had to make this holistic and a part of my lifestyle (building things, companies). Have a 7mo baby and a startup together now, can't think of doing anything else (and yes, shit does happen on and off).

Feel free to email d@klipper.io

Whenever I get depressed there are some coping mechanisms I use.

* Play games (e.g. OpenArena and FreeCiv), cheating liberally and/or playing on easy settings. (Yeah, take that bot...)

* Go for long bike rides. Take water, some food, and a good book. Go somewhere new each time.

*Read a good book. I read SF&F, but whatever tickles your fancy.

Oh look, all escapist mechanisms. That's OK. I can't offer any suggestion as to debt relief, as that's something else. But...

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. The world will come to an end BUT not today

5. Go run, exercise, play sport

6. Get a job, join a club, volunteer...

Good luck

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.

Failure is usually an iteration. My most recent project failed too.

Good thing is cheer up, at least now you know what doesnt work, focus on what works or what you think may work. I got myself a day job while working on another project on the side.

Girlfriend wise, well it happens. Love your family more.

"Pick yourself up, dust yourself off and start all over again!"

Keep a dialogue with everybody, don't shut yourself off from friends and family - no matter how uncomfortable it is.

Stay active physically and socially, get involved with your community and work wise, seek new employment and "keep moving".

No matter how bad it feels, just remember that this time in your life will pass - you will get past it.

The fact is you have tried your best and everyone knows startup is not easy. Your friends and family will get that.

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

For the debt side of things you might want to check out Dave Ramsey. His podcast is one hour of hard luck and inspirational stories on getting out of debt. Don't get hung up on his politics when they come up. The no nonsense advice is great.

Know that your friends and family still care about you deeply.

bad things tend to come up at the same. its the nature of things but you should do your best to distinguish between the two.

I guess you are not seeking advice here on HN on how to cope with your gf relationship - this issue (painful as it is) has nothing to do with your startup failure. So, one issue shouldnt cloud the other.

I guess that your startup failure still has value. A lot of other entrepreneurs are always keen to learn of other people's experience, so worst case your experience can turn into a blog that can lead to new followers, ideas etc..

In any case, things tend to work out in the end :) dont forget that 90% of startups fail and everyone knows that its not like you experienced something that should make you lose belief in yourself!

Im sorry about your startup, and even more so about your relationship...

I may not be able to give you relationship advice,

but would you consider sharing your startup?

The great people here might be able to give you enough guidance to turn it around. I'll certainly try and help as best I can.

All the best.

You would probably get a lift / good advice from listening to this:


If you're going trough hell, just keep going - someone smart said.

Just try to believe that everything will be OK in the end, and that all this what happened, happened for a good reason - which you will probably understand sooner or later.

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.

Do things because you enjoy doing them. Then you'll be less disappointed when your startup fails. You don't need money to be happy.

Sorry about your gf though.

You'll get through it. Make peace with yourself and you will find that your experience has value to others.

I went through something similar. And the business stuff is easy compared to the relationship issues.

Yikes. Somehow, an emoticon like ":(" doesn't capture the pain I feel for you.

I've been through a similar break-up at a low point as well, so I understand the pain.

Someone in this thread suggested going physically far away. There's a great aphorism in Latin America which, translated into English, roughly means, "no one's a prophet in his hometown." Going far away gives you a bizarre super-confidence and super-powers, since what was simple and obvious in your own world that you're comfortable in, suddenly becomes insightful and smart. So I second the suggestion someone in this thread made, of going far away! (Hello from South America;).

More abstractly (the following point isn't about you anymore; this just got me thinking), questions like this make me think: I sometimes feel that people don't talk enough about the risks of the startup world. They all sound so theoretical: oh, you could potentially lose money or friends... but no, that won't happen to me! The reality is... it's a "superstar economy," no different than being a soccer player or a rock star. Mark Zuckerberg as John Lennon (maybe Dustin Moskovitz as Paul McCartney? Ha! Maybe Eduardo Saverin as the famous "fifth Beatle" who left before they took of hahahaha!!!!!). We all instinctively understand that, okay, if my friends and I start a band in our garage, there's a 0.000000001% chance we'll end up successful - okay, so eventually you grow up and get a real job, and stop the band once we go to college. But yet, it's so curious to me that, when we want to start our own company in that very same garage, for some reason we think that we are much more likely to be the next Mark Zuckerberg, that the chance is more like 1% than 0.000000001%. We think we're not like the annoying cool kids in high school, but actually, within our own circles, we see the same patterns emerging: everyone, it seems, wants to be a superstar. Oh human nature!!!

My unsolicited -- and probably wrong so ignore away, I don't know the actual stats etc! -- instinct is the following, and I apply this to myself (and this works only for myself so it might not work for you, everyone's different): when I'm evaluating whether to jump into a project, when I'm evaluating whether to completely run with it and see if I can be the next John Lennon or Mark Zuckberg then, I would treat it no different than buying a lottery ticket or casino game that would be partially a game of skill but mostly a game of chance. If I feel like I'm in a position where I think I can afford to lose a lot of time, friends, and money (since I'll likely lose all three!) -- then I would go for it. But if I'm not in a position where I think I can afford to lose a lot of time, money, and friends, then I just wouldn't go for it. Or I do it as a background project on nights and weekends and see what happens :) So it's about your own evaluation of your own situation more than anything else.

Again, just because this sort of analysis works for me, doesn't mean it would work for you: everyone of us has different levels of risk tolerance, financial situations, family situations, etc. Even issues as basic as age: it's easier to be 21 and lose everything than to be 51 and lose everything, etc. They used to say Rome of antiquity, naturam expellas furca tamen usque recurret -- you can push nature away with a pitchfork, but it'll always come back!

Okay now time to listen to Janis Joplin's Me & Bobby McGee. Freedom's just another word, for, 'nothing left to lose'...


What was the startup's name?

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