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

82 points by verysadpanda ↗ HN
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

60 comments

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The fact is you have tried your best and everyone knows startup is not easy. Your friends and family will get that.
I went through something similar. And the business stuff is easy compared to the relationship issues.
“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.

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.

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.
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.

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

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.

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!"

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.
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.

What was the startup's name?
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.
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.

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.
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.

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?
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)
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.
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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.
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...

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.