I am (not) a failure: Lessons learned from six failed startup attempts
73 comments
·January 20, 2025kevmo314
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.
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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.
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.
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.
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.
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).
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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.
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".
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.
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.
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.
chasd00
Heh “it could be the purpose of your life is to serve as a warning to others” - despair.com
Traubenfuchs
The right moment to start writing down things you have regretted not to having written down in the past is now.
Ecoste
Thanks for the interesting read! How did you support yourself through all of the failed startups?
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
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.
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...
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...
sinoue
What a fun read. I hope you'll try again!
“If at first you don't succeed, try, try again. Then quit. No use being a damn fool about it.” ― W.C. Fields
lisper
> What a fun read.
Thanks!
> I hope you'll try again!
Thanks for the encouragement, but I just turned 60. Running a company is too demanding for me to try it again. My ambition now is to be a writer and find an audience that wants learn the easy way things that I had to learn the hard way.
hinkley
Despair.com poster:
Quitters never win. Winners never quit. People who never win and never quit are stupid.
r_thambapillai
I thought this was a very powerful meta learning, something that abstracts across all the experiences.
> 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.
Curious if you have any other learnings that are less specific to a particular endeavour but hold tru/derive from your experiences across all of them
not2b
Multiple "diabolical" (his word, not mine) plans to fool people about what the business really is (an attempt to get in the door with one pitch, then pivot to the real plan and steal their lunch) did not work out. Sorry about that, but putting out this post won't help this guy execute on similar plans in the future.
redcobra762
I'm genuinely curious as to what gave you the impression that he intends to try again. I read this as a brief little memoir of a man who has since moved on to bigger and better things.
flyinglizard
That's just business. I can't think of any business that's not set out to displace some other business, whether by competition or simply elimination.
not2b
Competition is fine. Deception, though, is more problematic, and if multiple pitches depend on it (like market a service to brokers to get their info but don't tell them the plan is to eliminate their jobs), people will be on to you if you aren't a very good sociopath. Perhaps look for more win/win opportunities.
zabzonk
> Growing up, I had two major life ambitions: to become a tenured university professor, and to found a successful startup company.
why the hell those two?
I eventually - into my thirties- worked out that i wanted to be a good computer programmer, and a good photographer. managed the first, but not the tatter - two bored.
What I mean, is why did you have those ambitions growing up. I don't think most normal young people really can't think what they want to do until later in their lives.
MattPalmer1086
> why the hell those two?
I would guess to be free to pursue interesting ideas, and then make money off them.
zabzonk
why tenured? (I can't be sacked?). why startup? (well, why at all, but also cannot easily be sacked, should the startup actually work).
just my opinion, and not to badmouth, but this sounds like a somewhat insecure person.
dasil003
That's a weird take, he's talking about youthful ambitions. Tenured professor is a pretty standard bar for academic success, and startup us shorthand for building a scalable tech company from scratch. These seem like perfectly cromulent ambitions to me, not sure how insecurity enters into it or why I would care if it did.
lisper
> why the hell those two?
Good question. I could probably write an entire essay about that but the TL;DR is that I thought that tenure and financial independence were the roads to freedom, which is what I really wanted. I also really liked (and still do) the college vibe, being surrounded by interesting people thinking and talking about interesting and weird stuff.
ktallett
Those with no failures never tried. Now I'm the complete opposite of someone who would usually say that but I believe it to be true. Failure at things is ok, it's just part of doing stuff. Just like death is an outcome of life. Anyone who tells you they have never failed either hasn't ever tried anything or is a liar and protecting their ego. It's ok to admit you made mistakes or failed or that you don't know something.
pockmarked19
It’s important to think not in terms of success or failure, but in terms of philosophy and mistakes. If you’re focused on the outcome there isn’t much you can improve on, the reasons for failure are many. Mistakes on the other hand stem from flaws in your philosophy, which you can readily revise. In a lot of the cases presented here, the mistake that stands out is working with the wrong people.
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.