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If you ever feel alone in this... (bubs.co)
439 points by dariusmonsef on Feb 23, 2013 | hide | past | favorite | 92 comments

In a nutshell, this is why the problem is so hard to fix:

  > When I was raising my first round, it fell apart because 
  > an A-list investor who had given us a verbal commitment 
  > backed out. He did this because he had heard from his 
  > friend, who I had went out for beers with, said that we 
  > were struggling and unsure of what we were doing. I don't 
  > blame the investor for backing out and I don't blame his 
  > friend for relating his honest opinion he took away from 
  > our conversation. But I will tell you that I now never 
  > share my struggles with anybody I think might be even 
  > remotely close to affecting my future opportunities. And 
  > in San Francisco, that pretty much means everybody.
It's not a problem of attitude, or perspective. It's that investors and potential hires and partners really want to make the best choices for themselves, and that means working with companies that are doing great and founders who are driven and aren't going to flame out or give up, which is perfectly understandable.

And so founders who want to have the best chances at "winning" have to create an aura of momentum, of inevitable success, around themselves and their companies. That's perfectly understandable too.

How would you even fix that? How do you even define the problem you're trying to fix?

>How do you even define the problem you're trying to fix?

The name of the problem is "uninformed decisions". Lacking real information about startups, the VCs rely on signals - social signals, their own prejudices, "common sense", that sort of thing. Had they had understanding of the field, or understanding of the emotional rollercoster that is building a new business, there would be much less reading of tea leaves. In fact, a hypothetical competent VC would inquire until he finds the weaknesses both in businesses plan and the team approach and morale, so that he knows what the problems are, rather than run away when he finds some.

To put it shortly, the problem is "dumb money".

The answer to this problem is "smart money". Raise funds from the insiders of the industry you're working in - at least they know half the game. And also from the startup veterans, as they know the other half of the game.

Dumb money has no place in the early stage business funding. The reason why dumb money saturates the startup discussion is the same reason why the interest rates are low - dumb money is at oversupply, so they are trying to get into every credible investment opportunity.

The problem is there is so much 'dumb' money out there 'smart' money is just noise. If you have 50 million to invest then investing 200k in 250 company's at random is a perfectly reasonable choice. And 50 million is a tiny slice of a ridiculously big pie, people spend close to that doing due diligence on really big deals.

Yep, that's why I meant by "oversupply". The dumb money is rather plentiful, and quite desperate for a ROI, so it's thrashing around making lots of noise.

It's also an interesting departure from the 19th century when capital was scarce and labor was plentiful. These days qualified labor, or as we call it now, "talent" is in short supply and capital is plentiful. It's as if the capitalism has ran its course and produced what it could in the end - abundance of capital. Not a bad time to be on the "talent" side of the table.

I want to offer something positive to go with that downer -- you can find people you can come to trust enough to talk to honestly. There are many investors who are great people who, once they've decided to back you, are going to be there for you and understand the roller-coaster ride and won't hold it against you. You can find co-founders who are level-headed and have the right expectations, and don't get freaked out by some straight talk. You can and should talk to family members and significant others. That way, it can be 'us against the world' rather than 'me against the world'.

The hard part is finding those people :)

How do you know when you've found those people? Some people seem completely friendly and level-headed until things go awry.

Even worse (and especially in LA) some people are completely friendly until you're not around.

have met such people indeed..

Key point: Talk straight AFTER you have money in the bank. Not before.

Make it common knowledge that anyone who pretends that they are winning all the time are frauds and hucksters?

Not that this is necessarily a good idea, but in terms of psychology it makes sense to me. Plant a kernel of doubt so that people ask real questions, and if they don't get honest sounding answers hit the door. Gives an incentive for founders to be honest with both themselves and others and less downside to doing so.

I was definitely told by several VC folks and by even the NSF grant office that if they get "overly optimistic" coming in the door, they tend to ignore what they say. Having a realistic appraisal of your problems and advantages is a sure sign of delusion and lack of maturity.

That doesn't help with the very real fact that suicide and depression are heavily stigmatized in our culture.

If you're down, that's fine. Everybody has rough days.

Depression, the kind that leads to suicide, is very different.

I've spent quite a bit of time around depressed and suicidal people: My brother (whose son committed suicide), both of the first two girls I fell in love with, and more than a handful of friends. So while I'm not a psychologist, I can speak from some experience as to what they go through.

A friend of mine once described depression as being this massive black ball that hangs in front of your nose that nobody else can see. It blocks out almost everything else in your vision, but nobody else believes it's there.

When you try to talk to people about it, they treat you like a crazy person, because they can't see this massive thing that is impacting your life.

The people that suffer from this are treated as if they have some type of permanent crippling disability, rather than a treatable medical condition. Oftentimes when they try to get help, they're ostracized by their peers because they're a "crazy person" because they've got a mental illness.

Mental illness. The label obliterates the person underneath.

People that talk about it, that try and get help, find that they've got fewer friends than they used to. That fewer doors open, because nobody wants to hire or invest in a crazy person, and even after that person gets the treatment they need, the stigma remains.

Many startup founders and Silicon Valley hotshots exhibit the signs of severe depression, but it's completely taboo to talk about it. Admitting that you're spending time working with a therapist or taking medication is effectively a career death sentence (unless you're already a success). And so the problem stays buried, and every now and then we hear about another bright mind that just couldn't take it anymore.

More people need to come out with these problems, so that we can talk openly about this as a community, but that process needs to start from the top, from the investors and the big-time successful entrepreneurs.

It would make it less stigmatized to admit that you're depressed and ask for advice about how to manage it if there were not as much downside financially for doing so. And here I am talking about acute, generally temporary depression, not clinical depression.

I'm the first to acknowledge the difference between acute depression and clinical depression. I wouldn't even venture to say that I have experienced depression because I consider self-diagnosis of psychological problems to be incredibly dangerous. Not to mention offensive to my friends who are clinically depressed (and yes, I have had friends and family commit suicide as well).

Me, I have anxiety issues that I have medication for. Sometimes dealing with my startups is overwhelming and I just crash and can't do anything for a week or more. But I am incredibly fortunate that this down state is not my equilibrium and that I have a strong internal correction that lets me realize I have a problem, gets me to actively try to find a problem, and which so far always has eventually gotten me back to a balanced place.

But I do know people who are clinically depressed, and they should frankly not be starting companies. If a friend who was clinically depressed were trying to start a company and came to me saying that their work was making their depression worse, I would do everything in my power to encourage them to seek professional help (which I am not), and to gently encourage them to consider alternative professions. It is not worth your health, mental included.

I would argue that there's a difference between "overly optimistic" and "overly confident."

VCs may find overly optimistic people suspicious, but I think overly confident is met with boundless praise in most spaces.

The first is about the project and the latter is about the person. Someone can say, "Oh you know, we have x, y, and z obstacles, but I know we're going to beat them." That's admitting there's problems. But if they said a word about doubting themselves, well, no one ever applauds that. And the inability to be truly open and vulnerable as a human being seems to be the stuff that leads to desperate loneliness and suicide.


You're right that this filter already exists to a certain extent, particularly among investors.

However, there's an optimal amount of humility and self-doubt that people are looking for. Deviate too far away from it, and people run for the hills. It's just another pattern-matching tool.

> Having a realistic appraisal of your problems and advantages is a sure sign of delusion and lack of maturity.

I think you meant "Having an unrealistic ..."

You are correct. Apologies, too late for me to edit it.

How do you even define the problem you're trying to fix?

The competitive nature of the marketplace has inherent perverse incentives. It doesn't get fixed, people just tend to adjust their world view in one of many potential ways that allow them to stop seeing it as a problem.

Founders can talk to therapists who won't talk to anyone else about their troubles. It's not a perfect solution, but probably better than not talking to anyone.

Not to downplay the value of therapists, but the help that a therapist could provide is different then the help one might find from a peer/colleague in the same industry/situation. the problem is therapists are always available (well, for a price) but a peer that you can trust with the same sense of confidentiality is rare.

Why would you want to hide that from an investor? Why is this guy raising a series A when he's already have these difficulties? Rather than stressing about raising money, he should put thought into what he is doing. Raising a series A when a person says "struggling and unsure of what we were doing" seems like it would only bring them up in greater strength in the future.

>And so founders who want to have the best chances at "winning" have to create an aura of momentum, of inevitable success, around themselves and their companies. That's perfectly understandable too.

Well, we can't all be Bill Fucking Nguyen thank goodness. I suppose it's expecting too much for people who are responsible for investing millions of other people's dollars to realize that sometimes people who appear "driven" and "visionary" are actually "full of shit" and "criminally insane".

I'm constantly amazed at the human mind's inability to measure happiness on an absolute scale, and societies inability to acknowledge that this is normal.

I know that I'm well off. I know I'm incredibly lucky to be working on exactly what I want. I know what I'm working on matters and will have a huge impact on the world eventually. And yet, the uncertainty of success (or at least its timing), and the inexplicable daily feeling of unworthiness/ineptitude combine to put stupid mental roadblocks in my path.

While unsurprising, it saddens me that an investor would pull away from a founder because they found out he was human. Silicon valley's greatest strength is accepting and embracing failure, I hope that strength will begin to extend to embracing the humanity of founders. If you expect founders to be perfect models of confidence, skill, willpower and brilliance, you will be lied to and eventually disappointed. It strikes me as part of our culture's maturation process that we begin breaking down these myths and replacing them with understanding, compassion, and realistic expectations.

I too think quite a bit about our ability to readjust expectations and inability to measure happiness on an absolute scale. I've come to the conclusion that it just might be our greatest strength.

Without it, we'd still be living in huts and hunting prey, because on an absolute basis that is way better than sleeping under a tree in the cold.

It's the thing that lets a child enjoy watching a lion at the zoo, behind glass, angrily advancing and pawing at them.

It's the thing that makes a billionaire keep working hard at the next big thing, despite them having enough money to not care.

Our inability to be perfectly happy and content with our situation, in an oddly confusing way, is what makes us so great, what makes us continue to strive to make things better, and get out of bed every morning to continue advancing humanity.

You're right but it's not as benign as you suggest. Our genes are stupid.

They don't care if you are happy or not, as long as you are potentially reproductively successful. They are so stupid they can't even tell the difference between drug-based euphoria, or other addictions, and genuine success. And our genes don't even care if the entire ecosystem collapses underneath us, because the whole species is acting the same way.

Sometimes this restlessness does "advance humanity", but that's not inherent in what our genes want. It's only because we have carefully set up institutions and practices such that the best way to compete is to serve other people.

But, barring the discovery of some infinite source of non-polluting energy and materials, at some point - either tomorrow or in a thousand years - this restlessness will have to be tamed. In short, there are limits.

And for individuals, those limits are much nearer, and the benefits of controlling your desires are as well.

I'm constantly amazed at the human mind's inability to measure happiness on an absolute scale

Under its other name, the ability to adapt to misfortune, this inability has been a very useful thing for humans to have.

This is such a good statement. Thanks for the contribution.

It’s funny how what you do (engineering in my case) affects the way you think about some things. I started to think of happiness not as a direct function of the different “happiness variables” (like wealth, relationships…) but as the derivative of those variables. For me it makes a lot more sense that how you feel is related to your perceived progress towards or away from happiness rather than your actual status on some arbitrary scale. It explains why rich people can get depressed and why people who have suffered extreme losses can be very happy a while after the loss.

I agree with you about human happiness. I'm well aware that being born in America puts me among the global top 10% by wealth.

If I could play the devil's advocate for this story--we've only seen the founder's side. In this blog post, I see no description of what the pitch to the VC was like. It's possible that these doubts and struggles were not discussed between the founder and investor. If this is the case, the investor has a reasonable stance for re-evaluating the verbal commitment. Why expect full disclosure later when you're not getting it now?

Happiness is not directly related to money, just like how a king of long ago can't be on the other side of the world in a day, money gives you diminishing returns.

Thank you for writing openly about these issues, Bubs. You really hit the nail on the head about not being able to have honest conversations with people, especially in SF. Since I moved here, I have met hundreds of people and interact closely with dozens... but I only count one person as a true friend in whom I can confide my personal struggles. Having to maintain a never-ending facade of success and happiness really is draining. Sometimes I wonder for what gain am I paying this price?

but I only count one person as a true friend in whom I can confide my personal struggles.

For me, I wouldn't even share my struggles with my best friend. It's hard to explain exactly why that is, but I don't think I could do it. Some things it would be easier to tell a random stranger at a bar... maybe because they don't have any expectations of you, and you don't have to worry about a feeling of letting them down, or disappointing them or whatever.

Having to maintain a never-ending facade of success and happiness really is draining.

No doubt.

Psychological breakdown lies down that road. You can only kick the can down the road, but you can't make it go away by ignoring it. Your choices are 1) talk things through with someone now 2) struggle for a while and talk to someone later 3) burn out. The first two choices are the same, except that in one of them you get to struggle before arriving at the same end.

Wholeheartedly agree. Showing weakness to someone who you respect and someone who respects you is incredibly difficult, but incredibly rewarding.

Good point. :-)

Having to maintain a never-ending facade of success and happiness really is draining.

Learning to be able to confidently say "I'm very concerned our company might die if we don't do X by Y because of Z" was one of the hardest and the most rewarding things I learned how to do.

I found that skillfully expressing my real feelings leads to much better results than not expressing them at all. If you pay careful attention to how politicians speak, they often utter phrases like "I'm very concerned about..." It sounds odd at first, almost fake, but when done genuinely it can be a source of great strength. You don't need to fake things in a time of crisis. You can share your darkest fears with people while maintaining a confident demeanor, and it does wonders for how people perceive you.

Of course this is harder to do than to say. I'm still learning, but a while ago I resolved not to hide my feelings from people anymore.

I've had a mentor point out the difference between processing the hard stuff that's going on and sharing it. She was saying that it's important to have peers that you can process things with, and once you start to have it figured out, you'll be able to share it more broadly with people you're leading and so on. You'll still be honest with them, but you're not falling apart or dropping this big thing on them that they can't handle. And I suppose you can process things on your own, but it's much better to have people you can trust to help you with that.

My range of wealth has been somewhere between -30k to 60k in the bank. That might not seem like a big range but I can tell you it is worlds of difference in terms of lifestyle. I once made $30,000 in the stock market, in one hour after the bell rang. Thinking it would keep rising, I went back to bed (rookie mistake!). I woke up to to find my gains negated, and my losses at around $15k. Over the past two years I have battled debt, debt that would have been nonexistent if I had just pressed the sell button.

I am thankful for this, very very thankful. I used to be, for lack of better words, a prick (still am, to a lesser degree!). I would spend money on trivial things. Now I know much better the value of a dollar, and have a least a little bit more perspective on the struggle that many people face ($30k in debt might seem trivial, but I paid as much as others with $200k of student loans due to high interest rates). As of today, I am almost debt free.

Startup culture really saddens me, not because of the chase for wealth - there is nothing bad about that. It saddens me because young people get rich really quickly, many times straight out of college or earlier. They never know what it is like to carry debt. They get rich, and they have no perspective. Elitism is not at all uncommon, subconscious or not, and it has nothing to do with how liberal you are, what charities you donate to, etc. Obviously, I do not look down on these people, I just wish they could experience legitimate hardship for their own benefit.

What a beautiful sentiment. Until I was in my early 30s, I was generally contemptuous of those who were struggling with weight issues, with physical or psychological pain, or with fear of death. I didn't mean to be so arrogant, and was generally not aware that I was at the time. I was not unsympathetic, exactly, I just didn't have enough personal context to grok others' internal state. I was young and healthy and financially comfortable, and with no one else to care for. It would indeed be sad to have continued throughout my life without seeing a bit deeper into the suffering of others. It would be sad to continue from this point without similar opportunities, though I think that once you have taken a first hard look, you can keep looking deeper without having to repeat old mistakes.

When I came to the Valley to raise funds for my first startup I called up Bubs connecting from a TechCrunch article he wrote [1]. Not only did he spend time with me through calls from Hawaii, he introed me to others from YC who went on to have significant impact in influence, connections and capital for my startup.

Bubs taught me an important lesson. A lending hand to a fellow entrepreneur can take you a long way. I am sure all of us entrepreneurs can relate to this article very deeply.

Thank you.


This is not just for startup founders. As an employee of a startup you are going to go through major roller-coasters as well. Having very close friends to talk to, and that understand your problems (they might work on similar spaces as well), is crucial. Your parents, your family might not be much help on these cases, as they wont understand or be able to give you good advice.

I have 3 friends that are very close to me, and they know every detail of my life (and so do I of theirs), good or bad. When I do need advice, or they do, we can rely on each other to get some feedback on any thing. But I trust them and I know they will have my back, and they wont divulge my personal details.

People that don't form these type of friendships are missing out. It makes the roller-coaster so much easier, and especially when going through life changing moments (job changed, marriage, breakups, etc).

I might have to add though that I suspect the startup community is full of people that are partially inside the bi-polar spectrum. Sometimes it takes a bit of a mania to start something new or crazy, but that euphoric high is always followed by a depressing low. Adding the uncertain nature of the startups, the emotional rollacoster becomes even more crazy and magnified.



Addition: The arm-chair psychologist in me says the author might have had BPD symptoms, (borderline) during his childhood:

"I cried in private, hoping that my cries might just be loud enough for somebody to hear. I hit myself, to create physical pain that might distract from the emotional."

> This is not just for startup founders.

The OP resonated quite strongly with me, and I am neither a founder nor (currently) an employee of a startup.

IMO, the struggle that is described here is inherently universal. It's shared by anyone who has to maintain a facade of success while facing intense insecurity (often financial).

Likewise, the emotions described will ring very familiar to anyone who suffers or has suffered with depression - regardless of triggers.

> My personal bank account & business accounts both overdrawn, tens of thousands of dollars in debt to family members and my credit cards maxed out or closed. I've had no cash in my pocket and a dwindling supply of food in the cabinet.

On a smaller monetary scale, that is in fact me at this very moment. Last week I was de-facto homeless (living in a $10/day rental car). I don't want to wax poetic about my mental state at the time, but it bordered on the worst.

I was eventually able to swallow my pride and confided in some close friends and family that I was tapped out financially, physically drained and psychologically in quite a dark place.

Knowing, viscerally, that I have a support network that is in the know about my situation and willing to back me up was very powerful. If / when I move past this particular time in my life, I know that I most likely could not have done it without them.

I think I used to view that as a sign of weakness and dependence. Perhaps it is, but that's not really something that concerns me any more.

Arm-chair patient: Maybe. I've only seen a therapist as a kid, but as far as I know, through the rest of my adult life I haven't had any bipolar tendencies. But honestly I'm not that informed on BPD. So if I am somewhere on that spectrum, I'm not living pretty happily there.

This is the important part to read:

"While I was in Thailand I got a dotted line tattooed across my wrist as a reminder of all those who didn't get another day, who all would I'm sure do anything to have just a little more time. I got the cut here line tattooed on my wrist to remind myself that if I ever don't fully appreciate the opportunity that I have and the life ahead of me, then I don't deserve it and it can easily be taken away. To me it's a very positive reminder, with a dark but real truth behind it."

I find that keeping a journal helps tremendously when I'm feeling low or find myself dwelling on negative thoughts. I believe it's because you can get away with fuzzy thinking when your thoughts are only in your head. Once you put them on paper you're forced to refine them and any distortion or irrationality in them becomes more apparent.

Good read, and useful. Whether you're in silicon valley or not, as any sort of entrepreneur, it's hard to find people you can relate to without any sense of competition. Family/friends can sometimes help, but they can't often relate. When speaking with close family, you may often either scare them or piss them off when talk of money issues way outside their experience level.

A few years ago I ran a phone/email group of some fellow entrepreneurs to help support each other - it ran its course and people moved to various stages of life and business at different rates, but was extremely useful for me to help put perspective on issues I was having in business.

I've also recently found a 'support group' of sorts in a local business group in town. Most of the businesses aren't tech related at all, but the support and being able to just be honest about issues 'in private' is very useful for all of us.

EDIT: If anyone is interested in starting/joining an informal support group, ping me at mgkimsal@gmail.com.

Yeah, I would love to see more of this. I use my close friends a bit as a sounding board for these sorts of things, usually they tell me -- dude, stop working so hard, even if you fail you'll learn stuff that will make you much much more valuable in the future either for your own company or even for someone else's.

I use my close friends a bit as a sounding board for these sorts of things, usually they tell me -- dude, stop working so hard, even if you fail you'll learn stuff that will make you much much more valuable in the future either for your own company or even for someone else's.

One reason, I think, that I don't use my best friends for a sounding board on this, is that they are too likely to be supportive and encouraging like that, and I don't think I want that kind of talk. For one, I'm too old and there isn't enough time left for that kind of thing. If this startup fails, it's pretty much "game over" for me, as I see it. So any talk that isn't "fuck or walk", "do this or hit the bricks pal", "do or die", etc. is counter-productive to me.

Rational? Probably not. But I don't want any fatalistic talk, or overt acknowledgement that failure is even a remotely reasonable option, because it might give me an excuse.

Of course, explaining why I put so much internal pressure on myself is a whole other story. And one that I don't feel like I could ever really tell anybody. It would involve too many uncomfortable truths and too much digging around in my past.

Easier to keep soldiering on, amped up on a steady dose of heavy-metal, adrenaline and caffeine and a mindset that there are two outcomes in front of me:

1. Succeed at this startup, and achieve some things I've been questing after my whole life.

2. Emulate Nick Cage's character in Leaving Las Vegas.

I think that it is unfortunate that you are in this situation. My close friends of all ages are not all necessarily perfectly comfortable talking to me about their deep-seated fears, but certainly some are. And the others have their confidant.

And certainly a fair bit of the feedback I get from my friends is "stop being lazy and work harder".

But I find that if I get too anxious or worked up, my actual quantifiable performance drops dramatically.

If I used your strategy, I would do worse because I'd be spending more time worrying about failure instead of working hard. Similarly, the anxiety of feeling like it's succeed or die would not make me more likely to succeed, it would make my health worse, definitely my mental health worse, and I'd be more likely to fail. It would be like being stressed out and deciding not to exercise anymore. It's only going to make me more stressed out.

Maybe we're just very different people, but I find anxiety crippling and a huge drain on my ability to do creative work in particular.

For me, knowing that even if I fail at starting my company, it will be much easier to get a good job afterwards being able to demonstrate that I've got the drive and interest to help a company's core mission is very, very helpful. This is the best advice I was given by my friends. Yeah, my company might fail, but every other company will be more likely to hire me to a management or other high level role knowing that I tried, even if I failed. They know a lot of it is luck, and that as long as I can demonstrate that I didn't fail due to massive incompetence or laziness (which will not be a reason I fail at it) it makes me a more valuable potential employee.

Maybe we're just very different people, but I find anxiety crippling and a huge drain on my ability to do creative work in particular.

Heh, yeah, it's hard to explain. I certainly have "stuff" that it would be nice to get off my chest, things that I don't want to talk to my best friend about, even things I don't want to talk about with my co-founder. But don't get me wrong... I'm not suffering from crushing, debilitating depression or anxiety here. And the feelings I feel are - to me - largely motivational.

I guess the biggest thing is, I don't know how to tell anybody exactly how scared of failure I am in this context, or how to explain why I am so driven to make this work. And now that I'm getting older and getting more of that "this is my last shot" mentality, the pressure is even stronger.

Anyway, I don't want this to sound too morbid. I'm not in a bathtub full of hot water with a straight razor or anything. Yeah, I sometimes worry that my story ends like Leaving Las Vegas, but that's just a background thread that activates from time to time. Most of the time, I'm just slogging away, working hard and dealing with the day to day stuff that comes along. :-)

For me, knowing that even if I fail at starting my company, it will be much easier to get a good job afterwards being able to demonstrate that I've got the drive and interest to help a company's core mission is very, very helpful. This is the best advice I was given by my friends. Yeah, my company might fail, but every other company will be more likely to hire me to a management or other high level role knowing that I tried, even if I failed.

Yeah, part of my problem is, I feel like I'm too old for that stuff to matter. Plus, the entrepreneurial route is the only way I think I can ever be really happy. It's not about making a lot of money, mind you. It's about the fact that I don't want a "job" in the traditional sense, for any company. As long as I have a "boss", in the sense of one person who can order me around and fire me for non-compliance, I will always chafe at that and be unhappy.

(Yeah, I know that when you run a company you still have a "boss" in a sort of metaphorical sense. That isn't quite the same thing though.)


Also, just to illustrate something... I'm just old enough to have grown up on a steady dose of 80's "feel good" movies. That brand of narrative pervades my thinking... the determined underdog, through hard work, grit and determination battles his way to victory against all odds, etc. I watch Rocky for inspiration once every couple of months or so. So I think that I actually need to be in this "do or die" situation to feel at balance with the world. That's my reality, being the underdog, having the deck stacked against me, and having to test myself to see if I can overcome. Sounds weird, I guess, but it's just something that's become part of my fabric over the years.

I mean, you're probably not that much older than me if you grew up watching 80's movies. I'm not exactly some undergrad considering dropping out to start the next facebook. I've finished graduate school, a postdoc, and am on year two of two startups. Arguably, I grew up more on Star Trek: TNG, but you sound like you can't be more than 10 years older than me.

If it helps inspire you at all, my dad started a non-profit at 30 (when I was 7), another one at 35, switched careers at 40, switched again at 45, and switched again at 50. And has every intention of continuing to switch regularly as soon as his job gets uninteresting. Life doesn't stop at 40 unless you decide to let it.

I do get what you're saying about having a boss. I find it frustrating too. I find my 2-day a week part time job much more stressful than starting two companies most of the time. Not because it's quantitatively more work, but because it's work that's not something I'm doing of my own volition.

That said, the more independent you present yourself in looking for an actual job, I suspect the more independent you'll end up being in a final position. I suspect that if you end up as a director of research and development, or a vice president of systems development, or whatever you will find that in practice you are extremely independent.

Sorry if that de-motivates you ;-) It's just how I would approach the problem you describe. Unless you were watching cartoons in the 60s, you're not too old to keep getting more awesome.

Life doesn't stop at 40 unless you decide to let it.

Yeah, I mean, intellectually I understand that (I'll be 40 this year BTW) and I don't mean to suggest that it literally does. I'm just saying that, at this age, the pressure starts to mount (at least given my particular world-view) for various reasons. Just to elaborate, and without boring all of HN with too much detail about my own personal drama... I was just diagnosed with diabetes late last year. I literally spent a night (3, actually) in the hospital for the first time in my adult life. So now I'm a lot more aware of my age and the inevitability of declining health and vitality due to age. Something like that kinda amplifies that "clock ticking" sound, ya know?

I suspect that if you end up as a director of research and development, or a vice president of systems development, or whatever you will find that in practice you are extremely independent.

True, and I'm not quite convinced that failing at this startup means heading for the Golden Gate bridge (or the liquor store, then Vegas), but there is definitely an under-current of "this has to happen, and happen now, or else" in my mind.

Sorry if that de-motivates you ;-)

Damn you, neltnerb, I was SO close to achieving my dreams, and you came along and destroyed everything!!! Aaargghh!! I will now spend my final years hunting you to the ends of the earth to seek my retribution!

Now that I can relate to. I was recently diagnosed (July) with a degenerative neurological disease, and expect to be unable to walk by 45, and be in pain most of the time.

So from that perspective, yes, definitely, I have been having a hard time figuring out what to do. The whole optimization problem of what to do has changed.

It's always been that my current happiness is a function of my current workload, and that my future happiness is a function of my current work and current happiness and future health, and that my future work is a function of my current happiness and current work, but let's just say... the prefactors for each shift rather dramatically when you can't help but think "if I don't do this now, I will probably never have the chance".

But it's worth considering, at least for me, that my current health will in large part effect my future health. So anxiety in the present will have a concrete quantifiable effect on my future health and therefore my future work.

That problem, I definitely have no answer to. But I do think that you shouldn't overvalue current work relative to current health. Not to trivialize anything (diabetes sucks), but focusing on your health now may well give you a lot more time in which you are able to succeed. The optimization function is not at all clear to me, at least.

For me, stress explicitly will increase the rate at which I lose neurological function. But I doubt it's linear; I mean, much more likely that there is some threshold at which I can operate and not degenerate much faster. So I should be operating at that magic optimization point. But unfortunately, my condition has such large patient-to-patient variability that it's unclear what that optimization point is. Ugh.

So yeah, I can feel the clock ticking too. Heck, I don't even have a decent boyfriend yet. And I want to have kids someday!

I dunno, it's tricky. And I definitely haven't figured it out yet other than to know that I need to make changes to reduce my stress level from that of some undergrad. That's just not healthy. Exercise, sleeping well, maintaining personal relationships, these are not irrelevant in determining your future outlook.

Again, I apologize for probably completely misunderstanding your worries. I'm misunderstanding my own frankly. This is a weird time of my life as well; perhaps we can just be confused together.

Hey, a ketogenic/low-carb diet has been shown to reverse obesity caused type-2 diabetes:


Juice fasts have been also shown to help too, see the documentary 'Fat, sick and nearly dead' for a couple of examples.

Life doesn't have to end at 40 because of your health. Also check out bulletproofexec.com

Yeah, I'm doing the low-carb diet thing, and my diabetes is fairly well controlled at the moment. I'm not in eminent danger of collapsing and dying as far as I know, but it's just that going through the experience I did (I developed something called DKA or "Diabetic Ketoacidosis" which is a life threatening condition, hence the hospital stay) has made me much more aware of the inevitable decline in health and fitness as I age. Yes, I know that proper exercise and diet and what-not can slow the process down, but I can no longer pretend that it isn't going to happen to some degree. Having that shoved in my face very unceremoniously has given me a new perspective on certain things. :-)

Once you create a narrative, it becomes harder to relate to a world that exists outside that narrative.

Most of the things which, in retrospect, give me a sense of having lived a fulfilling life, have rarely originated from the narratives I created for myself about who I am or what I should accomplish. I try not to paint myself into movie characters or personality caricatures anymore, as much as possible. Doing that gets me to the "acceptance" phase of emotional events a lot sooner.

Hey mgkimsal, I remember when you were doing something like that before. I would probably actually want to get involved in such a group. I'm about to head off to Chicago for 3 months for a consulting gig, but when I'm back in town, I'll get in touch.

please do - are you back in town at all during those 3 months? would love to catch-up f2f at some point in march if you're at all around!

I'll be home most weekends, if not all. I usually fly in Friday night on a late flight, then fly back out Sunday afternoon. I'll shoot you an email or give you a call, and we'll set something up. It has been a long time!

I'm not sure if @Bubs will ever read this, but I found this was a deeply interesting article, that hits close to home. If you are reading this - thank you.

There is so much to say on this subject, from various perspectives. Me, I'm stuck in Europe (offers-a-plenty, no chance for a visa). I am a founder of a start-up here, and I cannot complain about how it currently runs - but the things I've been through to get here ...

A lot about the start-up culture is simply different here in Europe - so maybe I am a little out of place among you. But what I believe is largely the same is the pressure, the stress, and the pretending. There are but few people who really understand what you are going through. "Why don't you just quit and get a (real) job ?" - if I had to raise a finger for how often I've gotten this response in dark times, I would be several hands short.

I believe there may be a need for some sort of chatter group for this. Maybe a tad unconventional, perhaps with a respected gate-keeper (like @Bubs) to check on people before they are let in (prevent moles), but once inside, everybody is anonymous to everybody else, and all conversation is group-private. You could be Mr Brown, I could be Mr Black - as long as I'm not Mr Pink. Perhaps it could have prevented what happened to those two founders mentioned in the article. I would be interested to join it, both for giving as well as receiving support. The good just writing something that the people who read it would actually understand could do.

Take this post for example - http://pastebin.com/BgxFCTEC . I wonder if whomever wrote it read this response: http://swombat.com/2013/2/21/truth-failing-startup and maybe felt better or even changed his view, or never saw any of the response and is sitting at his desk staring at the wall, wondering why (or if) he's still here.

I started my company in 2003 with one partner thanks to Visa and AMEX.

In 2006 we got bigger and reached to about 40 people working in 4 different countries. The financial crisis of 2008 brought us down (by accelerating the damages of our mistakes) and by December we went down to just 10. It was the most depressing Summer and Winter I've had.

In 2009 I worked for bouts of 50 - 60 straight days trying clear up the unfinished commitments we had with our clients and almost burned me up in the process but we got through.

Things went upward trajectory until early 2011 where the country I am located went through a revolution. Our local customers suddenly couldn't pay on time and we have had majority of our pending new contracts cancelled. My girlfriend of 5 years broke up around the same time and suddenly I stared back at the abyss that I thought I have left behind 2008.

It's been two years since that time and things have gone incrementally worse. It's a drip by drip bloodletting.

These cycles of advances and failures are exhausting. I was supposed to get better at this "be responsible of other people's payroll and livelihood" thing after ten years but I am not.

I still try though - every single day - inch by single fucking inch. I don't know whether this is grit or just denials. It's a close call.

Yup. I read it. Thanks for sharing. I'm not sure how well a big group would work. If its bit an intimate close group of people, it wouldn't be easy to open up and share. This is why I think it's important to have a small group of founder friends to confide in.

The only thing I find disheartening here is his discussion of how he lost funding because he told his friend they were struggling and had no idea what they were doing. This implies to me that they were not being transparent with the investor, and in essence were on the verge of "stealing" the investor's money because of it, because his aim was essentially to sell the investor on a thriving business that was in fact not there.

An investor should get a real and full analysis of the business, with accurate numbers, so it should not have come as a surprise or a fallout if someone said they "were struggling", because simply, their numbers and growth should have shown otherwise if they were actually worthy of investment, and no conversation should have been able to sway that.

You should never fear a transparent conversation with others getting back to important parties as long as you really have nothing to hide.

Still building the same company, so we weren't conning any investors. And we weren't doing poorly back then... Just going through some challenges. Site load bringing down servers, hiring, etc. rarely can an investor take the time to really know every possible deal and founder in the seed stage. They're looking at a volume of deals and need to be able to take thin slices of founders to make decisions.

And again, the point of my post is to say... Yes, we're not fully transparent with people because everybody else isn't. We're to blame first for the lack of transparency. I'm making an effort to change this.

I thought some aspects of this were interesting, but the emphasis on money felt tacky. Money is a motivator, but it is not an end to itself. The author appears to support this notion, but sets an arbitrarily high net worth of 5*10^6 and talks about how miserable it was to be "successful." I don't know. To me, all this money is a big problem in the valley. On the one hand, it's great, because there is a lot of extra money around for cool things to get done. On the other hand, there are people that are just around for the money and it feels tasteless and I have personally found it very unpleasant to work with people who hav ambition for money and the prestige. And there are a lot of people like that right now. Maybe I have been blessed to have grown up around some exceptionally succesful, but humble people. Just my 2 cents, though.

Sorry for the confusion. I wasn't trying to say "successful" was miserable, but that often people who are successful are so focused on the next level of success that they don't enjoy the one their at. And I agree with your point, money isn't everything. I guess I didn't phrase it well enough, but I grew up around wealth and that has provided me the perspective to know that it isn't everything. But money is powerful, and I hope lots of people who want to make the world better acquire that power.

I understand. You were open and your other blog posts see to show a true interest in technology. Thank you for your reply. I did not know you were active here. Hope you had a great weekend :-).

Thanks, Bubs. I felt better reading your post already. You are one of the founders I admire, especially on how you are able to balance between startups and family.

Thanks Thomas. I appreciate it.

Thanks for sharing this.

I can't help but see parallels here to Hollywood and the struggling actor. "Things are great! I've been in a few indies you probably haven't seen..."

I hope in time, with more stories like this, the mainstream will better understand the more human side of an overly romanticized place.

Thank you Bubs. The work your doing is so important and needed by our community. I've just finished Seth Godin's 'The Icarus Deception' and your post truly resembles art.

Great post Bubs. It's really unfortunate that the world responds better to "we are killing it", than to the truth. Thank you for being around to chat. You rock!

What the world wants is never what it needs. It needs authentic people who are vulnerable and willing to speak to the full emotional spectrum that most of humanity goes through. It needs a sense of community, and an ability to listen as much as it talks. These are things worth working on.

Fame is not real. It is little more than a flash in the pan of mainstream consciousness. As soon as they've discovered you they're looking to move on.

Just know that "we are killing it" doesn't mean anything. Like how do you do, it is just an empty phrase.

If things are really going well for people they will say things like we doubled our user numbers, became profitable, received an investment, got aquired, had an IPO.

"Killing it" is just a vague thing people say when they have no actual success but won't admit it.

I saw his talk, and honestly Bubs, you were inspirational. Keep up the awesome work

Interesting perspective and an engaging read. Thanks for sharing. Spotted some typos you may want to fix though:

> chartered plains vs first class

> there “limited success."

One more typo:

> either are or we're very depressed

fixed. thanks.

Good stuff. It hits a little close to home, but one thing stands out: the bit about how you fear showing any weakness or self-doubt, because of the impact it might have on others.

I would be very reluctant to share some of my own internal fears and self-doubt with anybody. Some of it is pragmatic (what if that person relays it to an investor), some of it is ego, some of it is, well, who knows?

Doubt is an odd duck because it can become genuinely self-justifying. I know of few other mental qualities that can claim that. If you doubt yourself, then, at the very least, you have the problem of doubting yourself, which is an actual, legitimate problem! Boom: you've just created a real problem out of thin air!

In truth, there is no place for self-doubt. It shows a lack of trust in your past-self and the decisions he made. You made the best decision that you could. (There is an exception, of course. If you made a decision when under the sway of some passing, mental evil: arrogance, greed, malice, hatred, then you might want to revisit the decision.)

The vast majority of mistakes do not come from some personal lack. They come from bad luck. Which is why individuals, as much as investors, need to diversify. Create more than one path to success.

(This is such good advice, maybe one day I'll take it! :)

I would add that a big cultural difference in US from, say, Ukraine is that people avoid talking about money as a plaque. As if it is a bad shameful subject. I do not know where it comes from - pride, competitiveness, avoiding jealousy, lack of confidence or extrapolating work policies into personal life.

I think people lose a lot because of this. First, they do not let share their struggles with each other. Where I came from people used to complain and exaggerate about their money problems, but nevertheless they share. Without sharing, there is less emotional and practical support from friends and family.

Secondly, without talking about money there is less chance to learn and cooperate for successes. If my friend wants to do X and never mentions to me that, I have no chance of telling him what I know about it from my experience or from my other friends experience.

Excellent post! The one thing I have to wonder is if there are those out there who can really separate themselves from their company's business.

I like to think of James Altucher's advice that you will be most happy when there are the fewest amount of people in your life who have the ability to create negative influences. In this case, having that investor mean so much to you that it has a severely negative outcome on your emotional well being is not worth it. I've come to realize that less stress is definitely worth more than extra income, in the long run.

It's a bit silly, but when I feel depressed or down, this is always good for perking me up:


It is a very inspiring story! I think everyone can relate to it to some extent because everyone has down times. It saddens me very much that we live in such a society that stigmatizes depression and suicide this much. I have only realized how bad the stigmatization is until recently due to things that happened in my personal life. This article also made me want to write out my own story and share it online. Maybe one day I will do that.

Very powerful post. I thought I was going down in flames recently but only realized that it could be so much worse and that it does get better with time. Thanks bub

Excessive risk (loss) aversion saps some of the enjoyment of having probably (but not certainly) sufficient wealth. 1% problems, I guess.

There are some people who can't learn from the rattlesnake biting the other person first.

This article is not for them.

Beautiful post. TY for the candor and truth.

Great Read, Thank you.

So, so so damn good.

> The truth is EVERYBODY is struggling.

Bullshit. I probably won't be able to pay rent unless my client pays my invoice next week. And that isn't very unusual.

I'm not about to kill myself, because I am used to the constant stress and poor health and barely getting by, but the point is, a lot of that post was just bragging, and financial security DOES matter.

I honestly don't feel sorry for rich people who want to kill themselves.

Totally agree! I get angry when people who have an iphone, a macbook and an it job are worried about their startup company and talk about being broke or suicide. Guys, you have never seen real life! I'm living in one of the richest countries in the world, but i know poverty, hunger, being homeless, without parents, without a bank card and without health insurance and without any perspective, any jobs or even university degree. Did I mention i was very good at school, but never finished because of having to work for food ? Business Gentlemen, you should not judge life by money! I think the general aim in life is to have food, health, a home, friends, sex, doing something useful and having a future. People in rich countries usually have all these things without even doing anything for it, so they cry about bad loans, bad jobs and bad internet connection. Guys, every day 150.000 people are dying on the planet, most of them due to hunger. So open your head and realize how good your life is.

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