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This line in the article resonated with me:

> First, it sets the stage for what was to come, and second, while it was unquestionably a success, it was not my success.

I used to think that success was being successful the way I wanted and I was often frustrated because things were working but not because of the way I wanted them to. Turns out, it's doubly difficult to make things not only work but also work the way I want.

I've since tried to be more open-minded and see wins that perhaps I didn't expect or want still as wins and it's made me feel a lot more successful. One might scoff and say I should hold myself to a higher standard, but at the end of the day, success is only an intrinsic feeling anyways. It's not a measurable metric so I might as well feel better about the progress I'm making.

In the context of the article, the author could see these all as failures, but it sounds like some of these were pretty successful. In fact, the author concludes as much, finding happiness in the "failures". It's all an arbitrary label anyways.




Sometimes wins are not necessarily measured with financial success. A company can utterly fail and still represent a win. I had one of those.

I started a self-funded tech company around 1998. This was hard tech, hardware and software. And I was the sole engineer doing all the work. This meant 18 hour days, 7 days per week to get the plane off the runway. Two years later, after booking lots of sales, we finally moved out of the garage and I started to hire people. Yes, I ran this beast entirely on my own for two years. A few years later a large well-known company expressed interest in acquiring the technology. The number being floated was in excess of $30MM.

What happened?

Well, 2008 happened. The economic implosion caused this company to second-guess entry into the market we had pursued --which they intended to do by acquiring us. The deal went from being a couple of meetings away from an acquisition to evaporating in front of my very eyes.

The bad news was that the economic downturn truly hurt us over the next couple of years. I had to shut it down in 2010 and lick my wounds.

This thing went from pouring all of our savings and an incredible amount of very hard work into a crazy idea, executing well enough to get a $30MM+ offer to closing the doors and nearly losing it all in the process.

At the time this felt like an abject failure and a waste of ten years of my life. It took me months to get my head back on straight. Today, looking back, I see it as a success. I took an idea from nothing to close to a massive life-changing exit and did so mostly on my own through hard work, grit and determination. That's a success story nobody can take away from me. I learned a lot along the way and most of those lessons were part of success in future endeavors.

Life can be funny and cruel sometimes. You might think you are going through your darkest hours when, in reality, you are growing a solid backbone that will support the rest of your life.

Entrepreneurship is hard. Very hard.


Honestly, that feels like copium.

It’s like anecdotes you hear from religious people during a disaster. “I lost five of my kids. But I’m so thankful that God looked out for me and saved one”


> It’s like anecdotes you hear from religious people during a disaster. “I lost five of my kids. But I’m so thankful that God looked out for me and saved one”

I am glad you edited your comment slightly because it was worse than what remained (which is still terrible and insensitive).

That said, one of my favorite quotes, by Mark Twain is:

"A man holding a cat by the tail learns something he can learn in no other way".

Which is to say that it is impossible for most to align with the mind of someone who loses a business, or much worse, a child, without having held that cat by the tail. And so, your comment, while misplaced, is understandable because you don't have a good frame of reference.

Additionally, in my particular case, well, the 2008 economic implosion caught most everyone by surprise. It was like a nuclear bomb dropped. Few saw it coming. Millions of businesses went down. Millions of people lost their homes and jobs. And, while I not, by any means, perfect and without mistake in my life, I find it hard to interpret such a catastrophic exogenous factor as a personal failure. Sure, it would have been nice to have had $10MM in the bank to survive it. Most non-VC companies do not have this luxury. We had five million dollar sale contracts evaporate overnight when our customers, in turn, had their banks materially reduce or cancel lines of credit. We had customers send truckloads of our products back to help us because they were filing for bankruptcy and the courts would have grabbed hold of our (unpaid) products and they would have been stuck in the hands of a trustee for months, even more than a year. Etc.

Like I said, sometimes you have to hold the cat by the tail to really understand.


I posted that 19 hours ago. I couldn’t have made any recent edits…

> I find it hard to interpret such a catastrophic exogenous factor as a personal failure

I mentioned in another reply that the 2008 crash hurt me too. It was definitely a personal failure that I had five mortgages where I owed a half million dollars, put 0% down on four of them and only 10% down on the fifth and I was only making $70K from my primary job at the time and didn’t know what the hell I was doing.


> I couldn’t have made any recent edits…

Your original comment, which I saw before the edit, characterized my comment as copium. Someone else responded to that before your edit.

Anyhow, your 2008 failure was, sorry to say, 100% your fault. Perhaps you were younger and inexperienced. We've all made stupid mistakes due to inexperience. Buying five homes with 0% down payment was an extreme gamble. We live and die by the consequences of such actions.

In my case, we were conducting business as usual and then, out of nowhere, the music just stopped...and there were not chairs. Very few people saw that coming. Those who did were focused on the financial world rather than engaged in running a business. This is why so many businesses got caught unprepared for such an event.

I am sorry you lost it all. That's terrible. I lost a home before due to employment difficulties. My mistake in that case --funny enough, young and stupid-- was to buy it with an adjustable rate loan. When interest rates went from roughly 6% to over 12% my world got turned upside-down in a hurry. Like you, I wasn't making enough money at the time to survive that. I lost the house a couple of years later.

Interestingly enough, that's what pushed me towards entrepreneurship. I had to earn more money. The only way at the time was to start an small electronics manufacturing business while keeping my day job.

So, yes, in that case, really fucking dumb decision on my part. Yet, at the end, it launched my entrepreneurial journey, something I am very happy about today.


I didn’t change that.

https://news.ycombinator.com/item?id=42773763

> Honestly, that feels like copium. It’s like anecdotes you hear from religious people during a disaster. “I lost five of my kids. But I’m so thankful that God looked out for me and saved one”

It still says “copium”

> Anyhow, your 2008 failure was, sorry to say, 100% your fault.

Isn’t that what I just said that they were my mistakes?

https://news.ycombinator.com/item?id=42774270

> And not being willing to admit your mistakes and assess your weaknesses means that you continuously make the same mistakes.

And then I went on to admit my mistakes.

In the very comment that you replied to I said It was definitely a personal failure

> Interestingly enough, that's what pushed me towards entrepreneurship. I had to earn more money

And I decided to upskill and I knew when I signed the offer letter at each job, how much I was going to make without any risk.

> Like you, I wasn't making enough money at the time to survive that. I lost the house a couple of years later.

I didn’t say I couldn’t keep my house. I made more than enough to keep my primary home. It was very much a strategic default. I had another house built and got an FHA loan three years to the day after my last foreclosure. Money is never personal to me


Interpreting a difficult event in terms that allow you to move on is not “copium”. we all do it all the time to explain our mistakes and weakness regardless of religion.

I don’t think any of these people are saying “I’m so glad my kids are dead” they are saying they are able to see these unfortunate events in a bigger picture.

What you may be looking for is “sour grapes” - something that was previously desired is now not viewed as highly after failing to obtain it.


And not being willing to admit your mistakes and assess your weaknesses means that you continuously make the same mistakes.

Of course I’m not saying in my original anecdote that people getting killed from a natural disaster was preventable.

In the appropriate threads, I have posted right here what I learned from my many mistakes - marrying the wrong person (since remarried), staying at my second job too long and becoming an “expert beginner” (I’ve done decently for myself since then), failed in real estate around 2008 (since recovered), etc.

You can look at some of my “favorited comments”.

This isn’t bitterness. At 50, I am where I want to be. But if you had asked the 35 year old me - divorced, negative net worth, shitty job with out of date skillset, etc. I wouldn’t have put on a happy face and say I’m not a failure.


>> This isn’t bitterness. At 50, I am where I want to be. But if you had asked the 35 year old me - divorced, negative net worth, shitty job with out of date skillset, etc. I wouldn’t have put on a happy face and say I’m not a failure.

The GP didn't say they thought it was a success at the time; quite the opposite. Aren't you basically saying the same thing, only with a different timeline?


This is how the submitted author ends his post

> I grew a lot. And I think my current happiness stems mainly from the fact that I like the person I've become, someone who can fail again and again and again and again and still find a way, for the most part, to be happy.

He didn’t say that his current happiness and success comes from the lessons he learned. It’s more like the lady who lost five kids and kept her faith because it was that God was good to save one not thinking if that were the case was he good for letting the other five die? (see also the biblical story of Job)

Without going into details (again look at my favorited comments if interested, I’m not trying to hide the details), what I learned from my failures is why I think I’m not a failure now - ie I achieved the goals I wanted to achieve - was a direct result of learning from my previous marriage and divorce, doing what is needed to not be an expert beginner - I got my first only and hopefully last job at BigTech at 46 (no longer there) - and was much smarter about my finances.


Ignoring what might be vapid reddit edge: it doesn't seem like it.

The GP would probably do well to see the endeavor as a success in terms of how they should behave in future. Any necessary adjustment would seem to come from the margins.


But he didn’t end his article with “my next startup after these six failures was a success based on what I learned”


He doesn't need to.

If retrospect exists to inform future decisions: getting to the GP's point in his business is a useful success signal.

Whatever it is that you're tracking seems less useful toward any question that isn't "am I rich from this right now?". The answer to which is "no". As-in "no shit". It's not useful.


In that case, that goes back to my argument that he is a “failure” based on his own metrics of his personal success criteria. He failed at his goal of being a successful startup founder.

How is he not a failure based on his own mission?


sports analogy time! people like sports because sports defines rules, bounds and how to determine a fair outcome with a winner. These are all limitations that are not at all clear in real life. Some people say "money is the measure of success in the games of business" and that supports the scarface point of view. Others point to the "journey" and talk about life occurring at the same time, factoring in family and personal emotions. Both are useful, neither are completely true.


Hmm.. if anybody feels the blunt force of failure it's them. But they feel it was a success so I believe it must have been. Also they don't need to cope now.


It’s a natural human coping mechanism to make sense of things in a way that allows us to continue growing and finding meaning, even in painful circumstances


Or just realize in the case of my anecdote that shit happens. There is no grand plan or puppeteer behind the scenes.

In the case of the original author, it would be be one thing to redefine success based on changing priorities. But not to pat yourself on the back and give yourself a participation trophy.

Yes success can come out of failure. Failure can also just come repeatedly and then you give up and try something else.


But I think there’s value in how we process and interpret those moments. It’s not about denying reality but finding ways to make it meaningful for yourself!


Ugh, I know this feeling too well. I've been pretty successful in life so far by societal standards but have always felt inferior and like I'm failing. Always. I think partly that's responsible for the drive that enabled earlier success, but it gets old. My first defense when those feelings bubble up is to remember we're all playing a game we can't win!


I'm very grateful to have the luxury of not having to play the game (very much). It puts me at odds with the majority of the world. Maybe if I was a success on the scale of our modern day oligarchs my circles would be filled with similar people, but being a salary employee who doesn't work primarily for the pay cheque and could quit for higher morals or values (without risking their family's welfare) is a weird situation. I feel like I'm often on the edge of the bubble and must be missing something.


We're all just animals on this floating rock in space, and meaning is what we ascribe to the series of events that comprise our lives. I personally resonate with the notion of shokunin which essentially is about honing a craft, and ultimately yourself - I definitely find joy and satisfaction in continually learning and improving at whatever I do...

When you combine that with wabi-sabi, and just a general appreciation for the present, I find I am able to cope with whatever life throws at me, no matter how bleak it sometimes gets.


    > I'm very grateful to have the luxury of not having to play the game
I don't get it. Did you inherit a bunch of money, or win the IPO lottery?

Real question: Comparing your social life before and after having money, what changed the most? Or do you hide it, so your friends have no idea?


Not having to play the game isn’t as expensive as you suggest.

Lots of tech employees, if they don’t let lifestyle inflation take over, hit a point where they could retire early but may not want to. At that point t walking away from a job is much easier.


You may be missing the feeling of being a human being with atonomy over the course of your life. Missing in the sence of absence, definately not in a sense of sadness or regret - be happy to not have to worry about the most existential things in life and being dependent on the whims of a boss / company / ecomomy for them. tl;dr I'm happy for you to not be in the rat race, it's completely not glorious (to be in it).


Yeah, the "success definition" trap is real. For me I was having coffee with a former co-worker who was now a VC because they had been at one of the same companies I had been but had joined "pre-IPO" and so probably had a net worth of 20 - 30 million. They asked what I was looking for and I said "To be successful like you!" and they said, quite seriously, they would prefer to be successful like me. And at that point we talked about the parent's point of how do you define success? This person had money but had lost their their spouse to divorce over 'working too hard' and were now alone. Meanwhile my third kid was on the way and I was doing okay but certainly not "FU money" okay. And yet from their perspective, that was more successful than they felt. That really threw me for a loop.


Without bragging, but I have succeeded in two of my startups and I have always been super lazy. Work life was mixed all the time. But never had stress. Always took time for myself. And maybe worked 3 days effectively a week. Remaining time I spend with my kids and hobbies. I dont believe in this rat race 60 hour a week thing.


You are totally bragging, but that's OK. I would hope you recognize the huge amounts of luck and context that go into a success like yours; many people work their asses off and still fail.

>> I dont believe in this rat race 60 hour a week thing.

The question is do you believe you were successful because of, or in spite of this?


Neither.

Success is never determined by hard work. It's always a combination of many other factors and at best hard work may contribute a little. Otherwise the billions of very hard working people struggling to feed their families would be extremely successful.

But that's not a story that you put on a poster, so people prefer to believe the lie that killing themselves chasing "success" is a good thing.


Hard work is preferred by employers over slacking off (for obvious reasons), so that's what gets promoted as the way to success.


I like this view. I’m not especially successful (by any of the measures knocking about) but in the midst of a startup again for the last year. This time I work how I want to work and am actually enjoying myself. The whole 80 hours a week startup thing is padded with a lot of performance art in my experience. I am actively avoiding all that this time around. I find that I solve a lot of things by not doing them or solving them when not actively trying. We’ve made great progress so far.


Totally feel this. I think all people should desire to be wealthy and to keep from being impoverished, but we should not define wealth and poverty simply in terms of our monetary wealth, or lack thereof. People who have the love of family and friends, a clear conscience, health, their physical needs met, and thankful hearts, are far wealthier than a majority of people in this world who have a large number in their bank account.

Yet in our consumer world, people are continually thinking of their worth simply in terms of the money they have or the money they make. I’ve known many married working moms, who decided to leave the workforce and be homemakers, who constantly felt like their worth diminished because of the decrease in their wealth, not recognizing that the bond they had with their children, was growing stronger and greater, and didn’t recognize how incredibly valuable that truly was.

Note: I’m not saying working moms can’t have strong bonds with their children, I’m talking about specific situations where for them it was hindering their relationships, and their relationships improved but was at the cost of less money.


The social pressure to play the game, even when you don't need to, is so strong. It is way easier to be happy when you have money than when you don't, and it may be something close to necessary (I guess there's happy poor people) but not anywhere near sufficient. A lot of smart, driven people seem to lose sight of this.


Yeah there was a song by silverchair(?) saying ~ “money isn’t everything, but I’d like to see you try to live without it”. When money has been tight for us in the past, that itself brings stress. Though knowing we have great community, who we could rely on to not starve, to be clothed, and have a roof over our heads alleviates a lot.

I think a lot of times those who don’t have great community around them, are often the ones who will really chase money over other things, because the impact of not having it is so much higher for them.


> Yeah there was a song by silverchair(?) saying ~ “money isn’t everything, but I’d like to see you try to live without it”.

Tomorrow. What a banger.

Next lines are:

You think you can keep on goin’, livin’ like a king Ooh, babe, but I strongly doubt it


I guess my question is can you even go for, "just your slice"? I don't want or need mega millions. I just want to be well off enough. Maybe that is day job? Preferably, it'd been cool to have some success, mic drop, and live a good life. Tom Anderson from Myspace fame seems to have done well. Successful product and off living his life.


The first "start up" I worked at was Sun Microsystems (I joined the day after they went public :-) so maybe not a startup at that point). But I was (and am) good friends with a number of people who worked there before I did. Pretty consistently a number of people who did well from that got to a point where they had "enough" and didn't need any more so they switched to working on things that spoke to their values rather than places where they could "make a lot of money." I have found that pretty inspiring and a counter balance to what passes for a 'success story' in the press today.


It’s so easy to get caught up in comparing ourselves to others


> and they said, quite seriously, they would prefer to be successful like me.

The different between you two though is that they have millions and can still have your lifestyle within a couple of years.


Except they could not. You can't buy with money the experience of a good life partner, you cannot buy with money the experience of having kids and raising them.

Those are things you buy with your time, your life clock if you will. You have a limited budget of time and you don't get to spend it twice. And when you get to the point where you feel like you've probably spent half or more of it, you might look at what you spent your time acquiring and be disappointed.

Pretty much everyone I've talked to about 'success' uses the definition of 'the sense of pride in what they have achieved in their life so far.'

If the value of what is a 'good' thing to achieve came from inside of you, then in my experience, you'll be happy with what you've achieved. However, if you adopted someone else's definition of what is 'good' to achieve, you may find that having achieved it you don't feel happy. I expect it is different for everyone.

What this conversation did for me was to show me how one thought about 'success' affected the choices of where you spent your time, that they were different for everyone, and that people using someone else's idea of success could be disappointed or unhappy having achieved 'success'. And that realization helped me make decisions about how I spent my time based on what I valued in my life rather than by an arbitrary "score" like a bank balance.


Buuuut they might not be able conceive... Or may regret being older then they wanted to be or any number of other things.

Money isn't everything.

Comparison is the thief of joy.


Also interesting that it seems like his relatively minor 1 year stint at pre-IPO Google was successful enough to pay for many other endeavors.

It's a great example of the power laws in startups: it's much more lucrative to have a minor role in a major success than a major role in anything minor.


I would go even further, it would have been much better statistically to work at any of the BigTech companies even in the past 10 years than take a chance at a startup.

Seeing the outcome of the startups he listed, it would have been much better to work as an enterprise CRUD developer at a bank, insurance company, etc


That really depends upon what you are optimizing. Someone with a PhD who wanted to be a professor, worked in an academic role in a big org, worked at the edge of many technologies; doesn't seem like someone who would be happy at an insurance company.

I will also repeat the obvious (but oft missed) observation: working in a revenue-generating industry, not a cost center. This doesn't need to be a startup, but very few banks or insurance companies generate their massive products within IT.


That’s true. But the author wanted to be a “successful startup founder” and that never happened.

I said in another reply, that I made plenty of mistakes and had plenty of “failures” so I’m not faulting him for that. But where did he say that he learned from his failures and worked on his weaknesses that allowed him to succeed based on his goal of becoming a successful startup founder?


> Seeing tts outcome of the startups he listed, it would have been much better to work as an enterprise CRUD developer at a bank, insurance company, etc

Enterprise CRUD developers don't make that much. I'm confident OP made more over his career than them.


How much do you think he made at his failed startups that didn’t exit and didn’t make enough to draw a significant salary?

The average CRUD developer working in the US in most major cities can make $130K to $165K within 5 years with aggressive job hopping.


OP would have to speak to his experience, but between a Google IPO and the $10M Virgin acquisition I would be surprised if he didn't average >$200k lifetime.

Throughout this thread, it's clear you have an ax to grind. Startups are obviously not for you, but many enjoy them and benefit.


He wasn’t a “founder” at Google. Google IPO’d in 2004. How many of the $n number of startups founded around the time that Google was founded and it IPO’d were successful and how many disappeared into obscurity?

There are so many people especially on HN who succumb to survivorship bias. Most failed startup founders never admit it. The original author is not one of them and he was willing to be open about it - that’s a compliment by the way.

“Many” may benefit from them. But statistically, most don’t


> the $10M Virgin acquisition

I think he wrote that he didn't make anything from that. He held onto the equity because he (unfortunately) thought Virgin would turn it into a success.


I think this is actually not as obvious as it seems as equity is also power-law distributed. An executive founder may have 10-50x the equity of a founding junior employee, who themselves might have 10-20x the equity of a key early employee.

The power laws actually cut both ways. I think the optimal path is not entirely obvious without some particular understanding of whether or not you are a stronger player as a leader or a follower.


It’s liberating when you realize that the "arbitrary label" of success or failure is often just a narrative we construct around events


I remember an old Steve Jobs biography titled “the journey is the reward”.

Overtime, I’ve come to appreciate that statement more and more. I think it is an incredibly profound insight about life.


I’ve had a lot of coffee breaks with highly placed peers who expressed concern because our boss was sure our success came down to one or two attributes and seemed completely blind to all the ways we saved him from himself. If apathy ever took over the team, we would burst into flames because of all of these details.

There’s a great old aphorism that sounds like sarcasm if you don’t understand this: “Take care of the little things and the big things will take care of themselves.” Any halfway sane team is dominated by people who are all too happy to jump on the Big Things. But for want of a nail, the kingdom can be lost. And if you cannot see his importance, and fire the farrier to hire more knights, then everybody loses.


When you see a successful boss, look around for his successful reports. They're always the ones cleaning up the boss' messes. The truth is that we all need to be saved from ourselves at some point (sometimes as education, other times as hard lessons), but tech culture certainly pushes that far with the "gifted visionary" mythos. A gifted visionary's much vaunted "Ideas > Details" only works when the detail people are there to make it work.


>> When you see a successful boss, look around for his successful reports.

With a good boss you don't have to look; they hold these people out and highlight their work, those people recursively do the same thing. In true success there's so much to go around.




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