I am (not) a failure: Lessons learned from six failed startup attempts
322 comments
·January 20, 2025kevmo314
robomartin
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.
scarface_74
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”
robomartin
> 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.
liontwist
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.
niam
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.
boodleboodle
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.
ErigmolCt
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
jebarker
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!
dowager_dan99
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.
djtango
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.
throwaway2037
> I'm very grateful to have the luxury of not having to play the game
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?
mylastattempt
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).
Deutschland314
[dead]
ChuckMcM
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.
holoduke
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.
dowager_dan99
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?
avastmick
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.
mostertoaster
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.
dowager_dan99
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.
memhole
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.
ChuckMcM
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.
ErigmolCt
It’s so easy to get caught up in comparing ourselves to others
Suppafly
> 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.
ChuckMcM
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.
arbitrary_name
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.
morgante
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.
scarface_74
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
dowager_dan99
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.
morgante
> 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.
AbrahamParangi
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.
ErigmolCt
It’s liberating when you realize that the "arbitrary label" of success or failure is often just a narrative we construct around events
slashdev
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.
hinkley
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.
numpy-thagoras
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.
dowager_dan99
>> 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.
null
jackcosgrove
There is currently a risk asymmetry in startup world that drives away people who could do good work.
Investors know the long odds of success, so they invest in twenty to thirty companies and wait for one to get big.
Founders and employees can't diversify like that, because you only have so many working years. To mitigate this we have decided to award successful founders with huge paydays as a lure to others to throw their hats in the ring. This has some malign effects, namely unsuccessful founders and employees get bupkis. It also attracts the wrong sort of personality to be a founder, selecting for too much risk appetite. (At least what I consider the wrong sort for building a sustainably profitable business.)
I have an idea for how to solve this and I wonder if it's already been tried or if there are holes in it. The idea is to spread the risk of starting a company across something like an accelerator class. If one company in that class gets big, it would be contractually obligated to hire and grant shares from some pool to other members of that class. This would be at the cost of the winning founders' stakes.
The upside for winners would be much lower, but the downside would be lower too. This would attract a different sort of person to this accelerator, and be a differentiator for selecting talent.
tptacek
This idea comes up here every once in awhile (often in the form of "a batch of startups where some % of the stock is shared across the batch).
I'm not saying it can't work, what do I know, but a challenge you'll have to address here is:
* By the time you're at the first big-money investment, the priced A round, you're dealing with investors who make just a couple investments a year.
* Despite that, the most promising startups are chased by VCs, not the other way around.
* If you're one of those promising startups, what would motivate you to take money from the investor structured the way you propose?
Most returns in startup investment come from a small fraction of breakout successes. Even if you got, like, 25% of startups to join this kind of funding compact --- which would be a huge, a momentous achievement on the same scale as the creation of YC --- the math here might not work out to where the shared-fate component of the deal was meaningful for any of the failed startups.
FreakLegion
It has indeed been done: https://founderpool.co/faq
Discussed at the time: https://news.ycombinator.com/item?id=23907342
jackcosgrove
This looks like it's a bit more flexible than my accelerator idea, while in the spirit of it. Thanks!
andix
There's your startup idea: communist ycombinator. ;)
yobbo
What if startup founders and employees are paid in shares of the investment fund?
joe_lin
Well, having been in an accelerator there were folks (startups) in my class who shouldn't have been there. i.e. their startups failed but it was blatantly clear why -- mainly immaturity and not listening to advice.
I think your idea would only work if there were rigorous selection process, but also some mechanism to "fire" founders who aren't contributing or insist to make terrible decisions.
hiAndrewQuinn
I'm not really sure I would feel comfortable investing in an accelerator class concept like this. Seems like it would suffer heavily from adverse selection.
Maybe if the terms were really good, like 20% of the company for $10,000 or something.
WalterSear
Not having to remunerate failed founders and starting employees for their effort is a cornerstone of the VC business model.
tptacek
They're investors. Why would they pay you for failing to generate a return?
jackcosgrove
"Failing for generating a return" makes it sound like a skill issue, when it was probably mostly bad luck with the business model you tried out. Negative results can be as valuable as positive results in science, why not in business?
Greedy optimization can also get you stuck in local minima. Why does any investor participate in VC? As an asset class it underperforms. There's something more that motivates people than return. Cool factor, bragging rights, and also I think a concern for growth and the macro outlook.
In my model the reserved pool of shares for failed founders would come out of the winning founders' pool. It's spreading risk across founders, not diminishing the stake of investors.
jfengel
My main lesson from running a startup: don't. And if you do, quit when the going gets tough. Perseverance does not pay off.
Obviously it doesn't always end badly. But we get a massively skewed view from survivor bias.
My life turned out pretty damn well once I got a plain ordinary job working for someone else. But I don't kid myself: when it comes to starting a startup, I did fail. The main lesson I learned was that I was always going to.
seany62
> My main lesson from running a startup: don't.
I hear this a lot and I think it is good advice because the only person who should actually start a startup is the one who sees this but still does it.
xeromal
Yup, it takes people who think they can't fail to be truly successful. Very similar to an athlete's mindset. You have to have the skill and innate talent but you also have to believe your shit doesn't stink
financltravsty
Always baffled me how little commercial sense HNers had when I was growing up and reading this forum.
It's as if no one taught them -- or they just don't have the sense for it? -- that a startup is just a vehicle to make money. There's nothing special about it. You can make lots of money without a "startup." You can make lots of money doing many different things even without a business entity. It's just an abstraction for linguistic convenience.
My biggest wakeup was finding people much less educated and much less intellectually gifted and much less socioeconmically privileged making a lot more money than what could be considered their betters in more prestigious and, on the surface, well remunerated professions.
If you don't want to make money, don't go into business. Stay at your job and grind a career out. If you have the desire to make money, your senses will naturally sharpen as you use them more to achieve that end. Otherwise, if you go and "build a startup" for any other reason than making money you will fail barring extraneous circumstances.
Baffling that this isn't common sense, really. But my fault. I keep forgetting a professional forum is just a proverbial water cooler, where you get to see a wide mix of people in your profession -- and all the different backgrounds, values, ideas, and ways of seeing the world -- most of which are continuous works in progress that culminate only at death.
mandmandam
> a startup is just a vehicle to make money
That is what's taught in many start up schools, for good reason. A startup can't ignore money without great luck.
However, it's not actually true. Lots of people start companies to make things better in some way, rather than to make bank. Some of them make bank regardless. Many businesses just tick along, but don't care about 'success' as determined by yacht size/botox per square inch/'status'.
> if you go and "build a startup" for any other reason than making money you will fail barring extraneous circumstances.
The idea that motivating people by money is the only or even best option is a major propaganda point in the class war (and quite silly if you think about it).
jeffreyq
Very :+1:
> Always baffled me how little commercial sense HNers had when I was growing up and reading this forum.
How long have you been reading HN? How have you felt the "HNers" w.r.t. nose-for-commerciality (and along whatever other dimension you think is relevant) change over time?
edelwiess
I dont understand why starting an enterprise has become such a scary thing in the tech world. So many people start businesses, so many mom and pop shops etc. IMHO startups have become scary to start because we jump too quickly into starting them or have too grand expectations from outset.
chefandy
The way friends approached startups in the .com era seemed to be more like “hey, [friend]… we know how to write code, and we think we can address [thing] in [some market] better than [incumbent], so let’s spend nights and weekends hacking together a working proof of concept.
It might not be representative, but the people I’ve known that wanted to start tech businesses in the past 15/20 years approached it the way people start restaurants. You can’t slowly ramp up most restaurant concepts with a DIY budget— you need to invest a lot upfront, and you need a lot of existing expertise for even pretty trivial concepts. (And before people say food trucks and catering and private chef and the like— catering and private cheffing are totally different businesses with very different processes and institutional knowledge, and in most places, food trucks aren’t dramatically cheaper than opening a small restaurant.) Folks seem eager to start acting like a CEO and delegating things to people paid with investor money rather than making something themselves and getting it off the ground. Maybe that’s what the business requires? Maybe in software markets, customers aren’t interested in scrappy small players anymore, perhaps worried about lack of support, shitty UX, them going out of business or whatever.
Just speculation. Not even going to pretend I’ve got broad non-anecdotal knowledge on this.
Earw0rm
I think the problem with that approach, in today's market, comes when you try to hire.
Junior engineers didn't cost more than any other recent graduate, and as you could get away with a few rough edges in production for quite a while, you could put together an adequately balanced team for not much money.
The tooling was much worse, but the compliance burden was much less.
Did your friends in the .com era talk about "doing a startup" or "starting a business"? I feel like that's changed a bit, people are more calculated and cynical about how the game is to be played with respect to rounds, exit strategies and so on. The "startup" model specifically means something a bit different to "starting a business", around ambition, scale, investment model etc. All businesses need to be started, but not all businesses are startups.
satvikpendem
The pendulum is swinging back it seems. More and more people that I know are now interested in starting bootstrapped businesses, growing them to $10k MRR or more then continuing them along or selling. Sites like Indie Hackers have popularized this model this decade than the 2010s which seemed laden with venture capital, most likely because it was the age of ZIRP.
Suppafly
>Folks seem eager to start acting like a CEO and delegating things to people paid with investor money rather than making something themselves and getting it off the ground.
This, but also it's a bit like gambling, this is the high risk / high reward way to do startups. The slower way is more stable, but you don't get to have fun with other people's money while you're building the business.
andrewf
I think compared to 15 years ago there's (1) more capital (2) more founders [enabled by better tooling and well-known implementation patterns] (3) less low hanging fruit on the product side. Any given opportunity is more likely to have other, well-resourced, folks chasing it hard.
muzani
A mom and pop restaurant can compete with Burger King and Starbucks. It's not quite the same with tech, as they can pay the $300k salaries for people to do the same thing you do, and they can buy out your market. Basically everything that can be done with money is stacked against you, and all you have as a startup is more grit than all these straight A students who graduated from ivy leagues.
malthaus
because tech people don't want to start a lifestyle or low-growth business. they are reading about giga rounds, unicorns and hockey-sticks as well as the VC/PG propaganda on hackernews etc all day and think that this is the only way to do it.
they eat ramen for 10 years, often even believing in someone else's dream without substantional equity to match the risk/reward profile. meanwhile, the plumber next door who started his own plumbing business is driving a ferrari on weekends.
mettamage
Do you have a good resource for starting lifestyle businesses?
satvikpendem
Funny how things change over time on Hacker News, an ostensibly startup forum that now more and more seems to be just another tech forum, and any relationship to YC and startups is now merely incidental, it seems.
cheinic63892
> My main lesson from running a startup: don't.
Worse than failing is not trying.
You will live your life always wondering “what if”.
When you fail, you will have an answer to the above question and can live in peace.
z33k
Worse than not trying is trying and experiencing burnout and/or destitution.
When you fail, it can be due to many things. Not everything in the world is controllable. This is one of the reasons why expecting zero ”What ifs” at the end of your post-mortem is unreasonable.
agumonkey
I don't think there's any absolute rule here. I'm pretty convinced that a startup would be healthier for me rather than my safe day job. The amount of churn and nascent burn out due to chasing tech debt and tickets surrounded by demotivated people is really bad.
I guess being aware of what you need and can afford is key.
null
orochimaaru
It depends. Why do you want to start something? Do you really believe in it? I mean there's got to be a certain set of "hell yes" questions that need to be answered in the affirmative.
Otherwise you're not missing much. Work for something that pays well, solve interesting problems, spend time at home with your family and friends. The problem is when you're wanting to start something because someone else did it and don't have the implementation or execution perseverance (or just don't believe in it strongly).
teaearlgraycold
Most people don’t want to start a business. They might fantasize but it’s not something they would enjoy doing. It’s fine to realize you have other goals and to work on them instead.
liquidpele
Yea, wondering “what if” is totally worse than being dead in a gutter.
makerdiety
This (very popular) sentiment you have can basically be abstracted into the “fear of missing out” meme. It's an unnecessary predicate, it's founded on presupposition and bias, and it's really detrimental to all serious long term analyses.
There's no proof that this personal feeling should be listened to or given behavioral authority, especially when it suspiciously conforms to the aesthetic that is widely shared by many who end up having only achieved a mundane life, despite “noble” projects launched because of arrogant egos. This social phenomenon which sponsors the freedom and agency of people fit only to be busy drones is wasting global resources on bourgeois affairs. Elon Musk and his eventual epic failure at super-industrialism is a great example of this harmful sinful pride.
The “what if” has only served to help overvalue ordinary potential, when that capability should have been limited to simple tasks, industries, and affairs. It's a mind virus riding on the waves of language and the beastly body of rationality, a false reality having been successfully disguised as a legitimate object to perceive within the cognitive sphere of humanity. It is deviation that surely has contributed to the collapse of the great liberal humanism project, the real goal of democracy and its encompassing civilization having been the quiet and stable enslavement of a massive surplus of dull brains and basic bodies. A mass of uninteresting genetic carriers who would do well to never worry about what is outside the scope of their common destinies.
The dialectic that there can be morbid peace if you would just test out the hypothesis that you can become a great man is an incomprehensibly devised thinking trap that can filter out men who don't know what the fuck is going on in the grand universe.
But God (or simply nature) works in mysterious ways and I'm glad that hubris was created to serve as an instrument for learning what not to ever do. And to materially benefit from, salvaging from the failures of future past technologies being a huge possibility to leverage. Your supposed tragedy is my informed opportunity, to paraphrase Jeff Bezos.
EDIT: If you ever invent warp drive or faster than light travel or functional nuclear fusion, I'll be looking forward to the blueprints of such treasures and strategic advantages ;)
solumos
Assuming that the process of failing doesn’t cost you your peace — which is certainly a risk.
null
scarface_74
Nope. I never lived one minute wanting to either start a business or be an early employee at one - I’m 50.
999900000999
I'm starting to think you really need to be well connected or at least come from an upper class background to win here.
Steve Jobs is sort of an exception here, not only was he adopted , but he was adopted by a very middle-class family .
I find myself really good at developing small apps, but very bad when it comes to the business side. I would love to find someone to work with who's good with business. But so far I've just been time scammed a few times by morons who come up with insanely impractical ideas .
And they never want to let you in for a full cut, they want to give you like 1% of the company in the event that you're able to build the entire thing out from scratch. If you discuss modest technical limitations they'll berate you for corrupting their vision.
Aurornis
> I'm starting to think you really need to be well connected or at least come from an upper class background to win here.
In my local startup community there are a lot of entrepreneurs and small startups founded by MBA students and recent college grads who clearly come from wealthy backgrounds. Nearly all of them either fail quickly or continue for years without getting any traction beyond their parents’ connections’ businesses.
The other side of being wealthy and well connected is that it’s really tempting to fall back on a job with your family connections or to play startup for a few years while burning through “seed” money from the family without the real pressure of needing your startup to succeed.
> And they never want to let you in for a full cut, they want to give you like 1% of the company in the event that you're able to build the entire thing out from scratch.
There are a lot of wannabe entrepreneurs who need a cofounder but don’t want to give cofounder equity.
The majority of successful founders and founding engineers I know had past working experience together. There are exceptions, but most of the time when someone goes searching for a cofounder or founding engineers because they don’t have anyone in their network, it doesn’t work out. It can work and does sometimes, but it’s so rare that I’m very surprised to hear success stories.
There are just too many people in the startup community looking to “hustle” their way into an MVP without giving anything up in the process. Also a lot of people who want to be “cofounders” and get 50% of your company in exchange for doing as little work as they can.
I was in a startup Slack for a while. Every other week someone would come in asking for advice about how to evict a deadbeat “cofounder” from their company who had secured 1/2 or 1/3 of the equity but wasn’t contributing anywhere near the other cofounders.
octopoc
I wonder if there’s a market for “work swapping” where founders of two separate companies will trade work without trading equity.
jongjong
Yes, the social aspect is significant. It's not so much about innovating and strategizing as much as it is about playing politics with rich people and hope that they let you build a successful product. Let's face it, rich people make all the decisions. If you're not rich, it's all about socializing and luck for you. It's hard to find a rich person who will let you implement your vision and actually control your destiny. It's demoralizing TBH.
wat10000
Jobs got his start in a tiny industry (tech was decently big already, but PCs were not) poised on the edge of massive growth as technology got to the point where you could build machines people would actually buy. And there was a huge moat, as the necessary talent was rare. And even within that rare talent, Jobs had the unique advantage of being able to partner with Woz.
Nothing you can do today with a typical HN skill set will come even close to that. There are thousands (at least) of people with those skills. They can build it too, whatever it is. You’re not Woz and you don’t know a Woz. Likely there is no Woz today; everything computing is so much more specialized and complicated and layered and just plain big. You may be able to find success in this world, but it won’t be replicating the Jobs story.
hylaride
Steve Jobs was connected: By being raised in Silicon Valley at just the right time. He even had a story (who knows how true it is) of him as a kid looking up Bill Hewlett in the phone book and asking about electronics parts (a frequency counter IIRC) and Bill not only got him the part, but gave him a summer job.
As for business, many successful tech entrepreneurs “learn” it either as they go or by bringing on business experts, but not giving them full control. For larger examples of the latter, see Eric Schmidt as the “adult in the room” for Google, Sheryl Sandberg for Facebook.
999900000999
If you had to look up someone in the phone book you by definition aren't connected.
Connected is when your Mom knows the chairman of IBM. Like with Gates.
liontwist
You have the agency to try to contact powerful people too, but you don’t.
gosub100
Even he failed twice before he made it big.
duxup
I'm on the ordinary working job track. I like it.
But if you're young, got the time ... I think it's worth a shot, or two, or more.
jrockway
I think there are upsides and downsides to starting young. On the one hand, you don't have much to lose, so failure is softer. On the other hand, you're missing some experience that would be useful.
I worked for a startup whose founder was a super young guy who had never had a job before being CEO. He was missing experiences like "what do I hate when my boss does" and so needed to repeat all the same mistakes. This resulted in things like... postmortem reviews with action items like "we should dock people's pay if installs are done incorrectly" instead of "we should ensure that the install crews have the tools they need to do the install correctly". (That action item was one of the few battles there that I won. We gave every installer a toolbox containing the tools to do the job. This improved the success of installs greatly. But who needs a meeting to come up with an "idea" like this?)
duxup
At least if young you got the energy, time, usually fewer family obligations, maybe even naive enough to do something others won't (as a good thing) and ... you know if that's the lifestyle you want.
But I hear you starting at zero life experience, that is bad. I would find it pretty painful to work at a start up and have to talk to the founder "bro let's talk about the basics of picking your battles" and do it ... well.
DonnyV
I think having an entrepreneur's mindset and starting young can work. But you will end up like every billionaire we know. Elon, Bill Gates, Zuckerberg, etc. They all started young as CEOs and didn't think twice about stepping on everyone and anyone around them to get the top. Now after years of this you have people that are very powerful and have no idea how the common person lives or how it feels like to work for someone.
scarface_74
It’s still not worth it. If you can get into a well paying BigTech company, save aggressively and let the time value of money be your friend, it statistically will make much more sense to do that.
duxup
If that’s what you’re looking for, you weren’t looking to run a start up anyway…
You’re talking about prioritizing a different lifestyle.
liontwist
Minor irritation: That’s not what time value of money means.
ErigmolCt
The narrative around startups is so often shaped by the success stories that get the most attention, but those stories are the exception
latchkey
> But we couldn't figure out a way to procure drivers.
I briefly worked for Grab the company, which was another SE Asia "Uber". Among other things, at one point they procured drivers in Saigon by giving the wives/families free chicken meat. This way, they could prepare the drivers meals to take while they were out on the road all day long.
Kind of a local spin on tech workers free meals.
NickC25
Of course you're not a failure. You still put food on the table, provide for your loved ones, and have a roof over your head.
You've got battle scars, and stories that are worth their weight in gold. Your experience is probably extremely useful for the right startup.
random3
When going through crazy stuff as a founder, I always thing "this is going to make for a very intersting story some day". Looking back I doubt I'll remember them all and, while keeping things in full throttle, I wonder if I'll ever get to write about anything...
My conclusion is that most interesting stories remain burried and we're lucky to see anythign real (as in true stories) surfacing, because people that are crazy enough to enjoy these pains, hardly have any time to write about them.
Meanwhile we're presented with a somewhat skewed reality that's both less interesting, less real and overly biased towards glamor. The title of a somewhat :) unrelated book keeps popping in my head "Reality is not what it seems".
hinkley
I wonder if someone like YC or a16z could manage to hire a journalist or anthropologist to make an honest chronicle of what happens at startups and not turn it into a propaganda piece.
Having to explain yourself helps clarify what you’re doing. The time “lost” keeping said person updated might even pay for itself.
random3
+1 on the Gimlet media.
Also reading Scott Belsky's "The messy middle" let me match a lot of my experience.
I tried to read "Eating Glass: The Inner Journey Through Failure and Renewal" but didn't have the energy/stomach.
Re a16z - "The hard thing about hard things" is not bad either.
However I think a frequent series short stories over a large period of time, would make for much better content.
scarface_74
I found the “Startup” podcast to be interesting when they documented real time the founding of Gimlet media, pivoted to other companies and then went back to document their acquisition by Spotify
Traubenfuchs
The right moment to start writing down things you have regretted not to having written down in the past is now.
random3
the thing with startups as founder / founding teams is that most days are actually good stories - so yes, the best way is to write as you go.
the thing is perhaps this is in fact the best way to motivate (or demotivate) the startup craft - you end up learning by drinking from the firehose daily. I believe there are few other types of activities that have such a forcing factor to learn and most are generally some sort of crisis (war, etc.) and so entrepreneurship is likely the least damaging one (at least for everyone else than the team haha)
neilv
Related to many interesting/crazy things being lost to history because the observer/actor is too busy to record them, and the things that do get reported consequently not representing reality... (And maybe a little relevant to the somber news events on this Monday.)
Many major religions prohibit making a show of good deeds. You're supposed to do it secretly, so that your intentions are pure.
But other people only see when a good deed is reported, so we're getting a distorted version of reality.
Some of these are reported for good reasons. But the worst form would be what social media kids are bombarded with: things like the clinically oblivious "influencers" who make videos of themselves exploiting a homeless person with a "charity" stunt.
One way to do good, while also letting people be inspired, is to do it anonymously. For example, the donation in a large crowd of them, or the anonymous rich-person's donation to a good cause (not a vanity university department named after yourself!), or any of the countless ways that one person quietly helps someone else.
You'll never know most of the times someone else helped you out, and most of the times you helped out someone else will also never be known. That's OK.
If you ever have the occasion to jump into an icy lake, to save a busload of photogenic schoolchildren and puppies, then you must try to get out of there right after, before anyone's phone dries out. Then the story will be about people simply doing the right thing, even an amazing thing, and fading back into the crowd. It'll be one of the best stories ever.
hinkley
There’s an old xkcd joke about how some grand problem in information theory has probably been solved on some mundane business task without the author even knowing what they’ve done.
random3
lol - thaught about this so many times in the past two years as I read thousands of papers and realizing that a poor engineer may have to deal with 2-3 discoveries a day without having the time (nor the math background) to deal with their deeper meaning and every time they see the "grand picture" it gets burried in the backlog maybe even stoned as NIH syndrome..
I always find it funny when some FP programmer ridicules others for not understanding monads, when in fact, those riduculed may have more extensive experience using them without knowing they are called monads.
After spending a little more time on both history and philosophy of science, I realized this is generally the rule rather than the exception, across all fields and functions
daveguy
This one:
(Title text is about some engineer solving P=NP locked up in an eggbeater calibration routine)
chasd00
Heh “it could be the purpose of your life is to serve as a warning to others” - despair.com
p3rls
I was thinking just today that Squarespace should contact me and I'll do a commercial for them based on my experiences of creating a webapp and turning it into a business because I was too picky to use a prebuilt CMS etc. I have eight years of nonstop pain and stories to tell.
Retric
You’ll recall a surprising number of details if you start trying to write even an outline of stuff down.
Many may not have actually happened, but it’s still worth considering even decades later.
gond
>Failure #5: “One by one, every bank that had initially responded positively changed their minds. Worse, not a single one of them would tell me why.[…] I never got a straight answer from any of the banks about why they changed their minds.”
Is anybody around with enough insight in that business to make an educated guess as to what happened?
hathawsh
Since around the start of the Internet, there has been a steady decline in the number of banks and credit unions in the US. [1] They have mostly consolidated with other financial institutions. The shrinkage seems attributable to customers moving their banking online and no longer depending on tellers, buildings, or geographical location in general.
Most banks are seeing this happening and acting as conservatively as they can. They are avoiding change because they don't want to be the next victim of the financial industry crisis. It's not a shadowy cabal; it's really just the fear of going out of business.
A few key banks, OTOH, are embracing change and innovating. Having strong relationships with them is key to making progress. It takes a very long time; 6 years sounds too short. I'm not sure the startup timeline could ever stomach the length of time it takes to build those relationships.
So my guess is that the author didn't have as strong a relationship as what he actually needed. My company has also worked with enthusiastic executives who turned out not to have as much weight in the company decisions as they hoped.
[1] https://usafacts.org/articles/whats-behind-the-decline-in-us...
sails
> It's not a shadowy cabal; it's really just the fear of going out of business.
Thanks for the insight, I was wondering about this point.
I generally tend to try and attribute what _feels_ like coordinated cabal behaviour to general incompetence or lack of control. This feels like one of those situations.
I've worked around banks and this erratic behaviour is pretty common, and mostly due to short term personal motivations, and lack of coordination rather than an excess of coordination (i.e. collusion - which is not to say that banks aren't guilty on this point, but I think mostly not the case)
antihipocrat
Some possibilities
- Bank operators responding to queries have no idea why a decision was made
- Banks rely on algorithms to determine credit worthiness, these are run centrally so a bank manager at a branch may say positive things but the system generates a report independently.
- The algorithms also can raise flags for other risks, such as anti money laundering. The bank will not disclose anything if a flag has been raised as a regulatory requirement.
Alex_Bond
My bet will be on core banking software provider issues. I think they did try to talk to theirs and got a response like, "We can do it in 5 years, and you will have to pay XXX million to us to do it".
There was a large-ish scandal in the late 2010s when some core banking providers were delaying Zelle integrations for smaller FIs, and they started complaining as customers were demanding it and leaving the larger competitors with it.
Another option can be as simple as this - they fear tech as most don't understand it. When I was working on a corporate charge card startup, my co-founder and I faced this issue many times. The craziest experience was when the bank was ok to be issuing bank for us but requested our clients to go to their branches to sign paperwork (the bank literally has maybe 5 branches in the whole USA).
Joel_Mckay
There are many reasons to do a startup, but people should only call it a business when the goal is either a tax deduction mitigation and or rapid entry into profit traction.
1. Don't use some clever or hard to remember name with a weird spelling. While easier to Trademark, the users and customers won't differentiate your site from the sea of attention grabbing garbage.
2. If people have zero paying customers, and zero revenue... than the hard fact is they were never in business, and should have founded a nonprofit instead (common for opensource support service entities.)
3. Often copyright and patents are infeasible for small business, and people simply can't build or defend things like a large firm. Thus, initially design products/services to last maybe a year or simply be disposable... When 270 desperate cloners show up to dilute the market sector... people quickly understand why they can't rely on Android, Steam, or Apple ecosystems to protect their bottom line.
4. There is zero loyalty without treasure. The only people that care if your firm goes into the red is you, and maybe the small-time shareholders. Most people can't take the constant adversarial posture with problematic staff, opinionated shareholders, and high-demand customers. Everyone thinks a CEO is lame till you become a CEO for a year or two... Every conversation from that point on is about money or marketing, and most people keen on building things tend to burn out of the role eventually due to social isolation.
5. No company lasts forever, if the operation is a projected liability it is your job to respond accordingly. Even if that means executing an exit strategy, and firing the entire problematic division.
6. Ask business people about their memorable experiences, and not about their money source. The superficial apparent function of a business is usually very different from the actual revenue model.
Best of luck, =3
kjellsbells
Very entertaining!
I'm always struck by the sheer serendipity of these stories. It appears that everything after Google was possible because of the safety net created by Google's IPO, and the author's time at Google itself ultimately came about because he and Urs hit it off over Lisp and Smalltalk. What would hace happened if the author had been allergic to dogs and had ended up at JPL because of their Fortran skills?
gruntledfangler
> Why don't the banks care? Because they treat the cost of fraud as just another cost of doing business, and they pass it along to you, the consumer. And they do it in a diabolical, stealthy way that you don't notice. But that's another story.
Desire to know more intensifies
lisper
See https://blog.rongarret.info/2013/02/a-simple-solution-to-cre...
That's actually the start of a multi-part series:
https://blog.rongarret.info/2013/02/a-simple-solution-to-cre...
https://blog.rongarret.info/2013/02/a-simple-solution-to-cre...
https://blog.rongarret.info/2013/02/a-simple-solution-to-cre...
https://blog.rongarret.info/2013/03/cutting-to-chase-repeal-...
https://blog.rongarret.info/2013/03/a-simple-solution-to-cre...
Keep in mind all that was written twelve years ago and the world has changed a lot since then.
mritchie712
> So why hasn't it been done?
The answer is simpler: it's not that big of a problem to the people that would need to solve it (visa, banks)
Yes, it' billions of dollars per year, but that's on a denominator of trillions.
> In 2022, global payment card transaction volume surpassed $40 trillion, with the U.S. accounting for over $9.5 trillion 1 . If we consider the $5 billion in unauthorized purchases reported by Security.org 2 , the percentage of fraudulent transactions in the U.S. would be approximately 0.05%.
1 - https://docs.google.com/document/d/1tudQcmL8lNH49iZZ8wRB88KW...
lisper
> it's not that big of a problem to the people that would need to solve it
That's not wrong, but it misses the point. It's not worth the bank's time to solve it, but for me it would produce a pretty damn good ROI. All I needed was one entry point into the system, but I couldn't find it.
mritchie712
why is this surprising? If they didn't pass the cost of fraud along, they'd all go out of business.
The interchange rate on credit cards is high, but "diabolical" is a stretch.
Also, fraud is a very small line item in a credit card P&L. Generally 25bps to 50bps vs credit charge offs which are closer to 3% to 6%.
Source: Ran risk for Bank of America and a credit card fintech.
jackthetab
In the past, my knee-jerk reaction would have been "Yes, exactly!" Then I heard patio11's podcast on debanking[1]. It gave me some interesting views into fraud and compliance and $STUFF. Highly recommended.
[1] https://www.complexsystemspodcast.com/episodes/debanking-pat...
jocaal
It's been a while since I read this article, but I remembered the title and it seems to imply that it is relevant
https://www.bitsaboutmoney.com/archive/optimal-amount-of-fra...
morgante
It's interesting how at least several of the failures were good ideas with bad timing/execution that others have replicated successfully.
iCab: Uber obviously was very successful with this ~same premise
Smart Charter: I assume you can easily book a private jet online now?
Founder's Forge: linking record-keeping and payment is what makes Ramp great; 10 years of fintech innovations made executing this much easier
Spark Innovations: this is basically the premise of Airtable
rsanek
As they say: ideas are easy, execution is everything.
naijaboiler
ideas are cheap. everyone has them. building a succesful business out of ideas is hard. really hard.
s__s
It’s honestly both. A good idea that’s actually feasible and has some kind of moat is extremely hard to come by.
antidamage
Most things that are new but not working can be solved by "I should try this again later" after the landscape has changed a little, whether that's supporting technologies, how receptive your market is, if your market even exists yet.
babyent
That was a good read. What impressive perseverance, and also a positive outlook. But, reading it made my FOMO worse. I guess one has to experience it fully to apply it. Or maybe not.
I quit my job a year ago to pursue my own ideas. Like the author, I had made some money from a IPO. The post-IPO environment with heavy bureaucracy killed the vibe and I quit. Note that it wasn’t a Google tier company, but I made enough money that I could take a risk for some years without income.
For me it has only been a year. But I feel like a huge loser at times. In no scenario will I give up until I’m utterly defeated or captured the castle - I’m not a quitter. But this feeling gnaws at my soul.
I have failed to find a co-founder. Most of my friends are not interested in startups. So, I have had to look elsewhere. Between people who screwed me over equity, people who didn’t want to do the work, and my own imposter syndrome (I’m from a low ranked state college, and people I meet in SF are elites), I feel horrible and alone. I tried and even successfully built some projects over the past year, but ultimately nothing worked out.
Now, I’ve decided screw it. All the advice about sell first and get a co-founder - sounds great on paper. And I have some doubts around that whole belief but that’s not important.
I know actual pain points I’ve faced in my decade long career. I’ve done both highly technical and highly functional work. I’ve talked to enough people and validated my idea. I wish this thing existed and that I’d worked on it sooner instead of trying something different with randoms.
So, I’m just going to go and build it. I like building things, and I’ve gotten enough recommendations and performance reviews that point out that I’m good at delivering value for the customer and making sure my team succeeds.
So I’m building a product. I am able to dogfood my own product as I build it which is great. It’s a somewhat complex, b2b AI enterprise product, and having built multi-billion dollar enterprise software and delivered multiple multi-million dollar implementation projects, I feel that there is really no rush. Most enterprise software and organization processes are awful and not well engineered nor well thought out.
If this fails, whatever. I tried. If it works, amazing. I like building good things and have a track record of doing so, albeit for others.
But I fear I will keep feeling like a failure until it is successful. On the other hand, it would be very cool to build a solo founded enterprise product and deliver actual success.
Anyway, thought I’d share my thoughts it feels good to type it out. Thanks to the author of the article for sharing.
bjelkeman-again
The one thing I have learned on my journey through 6-7 startups is never start something without a sales person onboard. When we do we end up building something interesting with no customers. I am sure you can be your own sales person, but I don’t have it in me to do both.
babyent
Agree on the sales! Definitely need to do it.
I did hundreds of cold calls for someone else. Honestly the most intimidating thing I've done but ended up learning to enjoy it.
I also enjoyed meeting our customers at our conference at previous job and it was a fun experience talking to people and showing off what we'd been working on or understanding what we could improve.
I am not an extroverted person, so it definitely does not come naturally to me - I'm suppressing butterflies if I'm being completely honest.
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.