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Ask HN: What has been your biggest mistake?
37 points by dhotson on Aug 4, 2008 | hide | past | favorite | 100 comments
I'm keen to learn from failure, and what better way than to learn from the mistakes of others. :)

What are some of the biggest mistakes you've made.. and what have you learnt?

1. Not majoring in computer science the first time I quit my physics major. If you like something, don't stay away from it for silly reasons (like thinking that school will make you un-like it).

2. Not knowing the difference between profitability and traction when I was looking at startups to work for. I spent 2 years at a relatively low-growth startup because I thought that its profits meant it was successful, when I could've learned much more at a higher-growth yet unprofitable startup.

3. Letting ideas sit too long. I had the idea for http://www.whatshallidonow.net/ about a week before I started implementing it, but was busy with job apps. In the meantime, http://nowdothis.com/ launched, and now they have all the momentum.

4. Spending too much time on super-ambitious projects and ignoring the low-hanging fruit.

In the meantime, http://nowdothis.com/ launched, and now they have all the momentum.

Wow, momentum for what? A textbox that echoes. Woot. They've got the echoing textbox racket nailed down.

Shit, I'll just bookmark this comment link and use ynews as a to-do list.


1. Buy gun.

2. Shoot self for not releasing my todo list app soon enough.

You do realise that nowdothis has a better gui than yours, right? Given the two services, I'd pick theirs.

Yeah, those're related problems. Because of the constraints of getting it out fast, NowDoThis ended up simpler, which ends up making it better too.

they've got amazing simplicity, and done client-side so instant response (remembers you with cookies, but seems to be no server storage). But you have to do the tasks in strict order, and you have to finish it before moving on (you can't just "make progress").

whatshallidonow changes the order. it has a "made progress" button. it would be nice if it had a button "skip - I don't want to do this one right now!". (tho you can achieve that effect by reloading, ctrl-r).

finally, the dothisnow guy gave a shoutout to our guy nostrademons here (and also to yetanothersimilarsite) http://nowdothis.tumblr.com/post/44066616/synchronicity

now they have all the momentum.

"Your greatest competitor is non-usage."

That quote is not just encouraging, it's also literally true (unless your market is >50% saturated). Plus, no two products are ever identical (whatshallidonow is a slightly different idea), and no two users are either: some like yours. However, I agree there are benefits to being first, #1, etc (and it's more exciting).

I like the interface of nowdothis.com - I like the idea too, well done!

I'd like to reiterate number 2, it was 4 years for me at a low growth, barely profitable startup.

I applied for a job at Lycos around 1997. I passed the simple phone interviews and they scheduled an in-person interview. My wife did not want to make the move it would take so I cancelled the interview. We still live in San Diego, I feel if I was up in a more exciting environment I could have done better.

I instead joined this one startup of sorts, worked literally 15+ hour days including Saturdays. Unfortunately it hit a rough patch and they could only afford one programmer and I wasn't it. So the other guy now is making around 15k a month now. They hired me back but I make about a 3rd of that. The system generates about 50k a month in free cash flow and I built all of the fundamentals of the system.

.Getting a degree. Honestly, I didn't need it. Contentious subject I know, but from the Hacker perspective, I have always relied on self learning in concentrated bursts to get me through - want a thorough understanding of TCP/IP? Spend 3 weekends going through the documentation and then playing around. Not 6 months in rigidly structured classes with no leeway for progression above and beyond what is in the curriculum. I could have got a job that paid my pocket money, whilst learning more and coming out with less debt. "but would this have paid off?" I hear everyone say. My degree or time in education has absolutely no standing of where I am now, apart from the fact that I feel I could have been here by early twenties instead of mid twenties

I can understand this sentiment, but from my experience a lot of the value from doing a degree isn't from what you learn in class.

For me, the biggest value came from meeting other like minded people and being exposed to brand new concepts.

There's also value in learning how to finish things. I can understand that people drop out (for many reasons) and that's fine, but I think it's important to learn how to finish things off.

Although, knowing when to bail is probably also just as important. :)

I think the mistakes that can be classified as the 'biggest', are typically the ones made in personal relationships. Those are the things that probably cannot be mended/replaced with any other 'equivalents'.

In terms of career/work etc, i really do not think one needs to worry much or brood over past decisions, we all got plenty of time (hopefully) to work everything out as we want it to.

This quote sums up a lot of things nicely:

  The greatest mistake you can make in life is to be continually fearing you will make one. -- Elbert Hubbard

Not sleeping with more women. When I was younger, women were more plentiful (and looking for relationships) but I spent most of my time in front of computers.

Today, computers are more plentiful and most of the nice women I meet are already married or in long term relationships.

I just modded you up, but as I think about it more, I realize that had I been more promiscuous, I may have passed over (or slept with but not stayed with) the girl I am with now in a long-term (long-distance, unfortunately) relationship and I feel that I can spend the rest of my life with her.

I could understand if your regret were not dating, but is your only regret a lack of sex? The "nice women" would be averse to marrying you if your number got too high. From the perspective of a marriage-worthy woman, it's fine to be a virgin till 23-25, and the ideal number for a 30-year-old male is probably 1-6.

How old are you? It seems that the odds get better for a guy until age 35. When you're 20, the age range of women you'll be able to date is very limited: approximately 18-21. When you're 35, it's 23-40. Gender ratios also improve (from a male perspective) dramatically as you age, with noticeable effects in dating. I'm 25 and loving it; I definitely don't miss being an acne-pwned, insecure 19-year-old.

Also, if you're looking for marriage-worthy women, have you considered moving abroad? The only reason I still live in the US is that New York is very, very international. I would not be able to stand it if the only women available for dating were white, suburban Americans.

Wow, what a difference in perspective. I couldn't imagine wanting to marry a woman who even cared about the number of women I've slept with. My wife and I were both very "friendly" before we met each other and neither of us has ever even bothered to ask the other how many people we've slept with. It simply doesn't matter to me.

I wonder what your criteria for "marriage-worthy woman" is.

It's unclear why living abroad would do much to broaden one's dating gene pool. Certainly you can avoid white, suburban Americans in Japan, but good luck meeting someone who isn't Japanese. Outside of the USA and Canada most countries are very monocultural. For example, if you are moving to Sweden for dating purposes you should be sure you are into Swedish people before you go. It is far easier to date outside your race/culture in the USA. I'm white, and haven't dated a white person since I was in high school.

In regards to your ideal number, 6 at age 30 would be a minimum. Lower than that and your potential dates will wonder what's wrong with you.

Being 25-30 I have yet to see this trend :( and don’t see many of the people I know with partners more than ±4yrs their age.

Moving may solve the problems related to geography, but perhaps not those of culture and lifestyle which often form a larger part of the problem people face. As addressed by others, going to another country may not help any more than simply going to a larger more cosmopolitan city. But even in big cities (London, Paris, New York etc.) it is still possible to be single/lonely, as many are. I think only big changes in lifestyle really solve much of the dilemma such people face.

Lastly, as we get older, we all start to look at people more as future partners even from the outset. This becomes harder as, using nature as an example, it is probably fair to say that the most desirable mates are taken early. Hence those that leave things until later e.g. to focus on career etc., often find things harder and (I dare say) have to settle for less or compromise more. This seems especially true for women who feel their biological clock is ticking and develop the nesting instincts. I suspect this is one of the reasons that in a generally declining/competitive online dating market the sites focused towards marriage in the niches e.g. Jewish/Muslim/Christian matrimonial sites, do well compared to the rest.

Anyway, I am building a dating site to address some of the problems I see and welcome comments/suggestions/ideas of others (your experiences, what you see is broken, solutions). You can contact me at babulmiah{.a.t.]yahoo<,d,o,t,)com. Hopefully, I’ll launch an alpha for HN review soon.

Thinking other people are dumb. Even if it were true, it has yet to get me anywhere.

I could not agree more on this point. It seems like this comes up all too often in design discussions, and it is difficult to get around in a productive manner.

I used to have regrets. For much of my early 20s, I thought not having tried to make music professionally was a mistake. Then, later, I worked at Macrovision and saw the music business up-close and was very glad not to be part of it! Similarly, for a couple of years after my PhD I regretted not staying in academia. Working for a startup has completely cured me of that regret.

I guess I've learned that something you believe to be a mistake today can turn out to have been a smart move given a year or two's hindsight.

Not getting it in writing. It doesn't have to be a long drawn out contract, just a short email explaining what the agreement is. Even amongst friends, you will never regret having an email stating your agreement.

Trusting the level of integrity, gratification posed by founders/managers and slogging my ass for their success. Reminds me of Austin Wiltshire's blog on New hire Cannon fodder.

Trusting the wrong people is painful - even when you have it in writing.


1. working as employee #6 at a startup in boston instead of google in 2001.

2. working as employee #6 at a startup in SF instead of youtube in 2005.


This reminds me of Brian Lent. He sort of missed out on both Yahoo and Google. http://blogoscoped.com/archive/2008-01-22-n20.html. Edit: some choice quotes.

"When Filo asked Lent if he would like to join Yahoo! as employee No. 1, in order to keep the founders on their toes with his skepticism, he laughed. 'You couldn’t pay me enough money to work for a company called Yahoo!' he recalls saying at the time."

"In early 1996, Lent explains, “We all said, ’There will never be another Yahoo!’”"

Yeah, I do feel for you. But I wouldn't consider this a mistake. I mean what if the startup you worked had become big. Its easy to say in hindsight. Like they say in stocks - "You are always wise, the next day"

I feel for you, dude...I hope there's no number 3 next time someone asks you this question.

I hope he doesn't decide to go anywhere again as employee #6. I am not normally superstitious, but I would avoid that like the plague going forward.

'Oh you currently have 5 employees? That is too bad...' :)

Totally. It wouldn't be pure superstition either; a 6th employee commands a certain amount of stock, a certain amount of wages, and is hired at a certain stage.

Ouch! However, this counts as a risk with a not-so-fortunate outcome right? For most people, a mistake would be the gap between the risks they took and their innate risk-taking ability. In startupspeak, there's nothing wrong with a steady job if you aren't an adrenalin junkie, and there's nothing wrong with multiple bombed ventures if you are.

Third time lucky?

At least you had the courage to work at various startups, even if they failed, which is more than most.

At that point in time, where the other 2 startup ideas less/more crazy than google/yahoo?

Google was obviously a good company at the time. I just thought being #6 at this other startup would leave me better off financially than being employee 300-something at Google. Not the case.

In regards to YouTube, I was actually doing work for a YouTube competitor at the time. They sold their tech early to another YouTube competitor, but since I was a contract employee, not a founder, I didn't make any money off of the sale.

So how do you evaluate and incorporate that magic factor when making the decision on which startup to join? The regular factors being a combination of market, people, product, personal value and financial?

Not saying "no" enough. Trying to do too much, and doing none of it well.

So work on a small task you can complete rather than trying to tackle a giant problem you'll never finish.

I spent a year after college goofing off, and not in the good way either. When I finally woke up (literally, pretty much) and realized a whole year had passed by I had lost a lot of momentum. Otherwise I would definitely have completed my master's (or at least worked on something useful). I blame social security.

But at least I came through - I had friends that time who are dead now (one overdosed on heroin, one crashed a stolen car while a fugitive from prison).

My PhD. Sure I learnt lots of great stuff and met some great people - but I could've done all that with a master's.

What did you get a PhD in?

Human Computer Interaction. Specifically, I wrote about using participatory and user centred design for implementing ubiquitous computing systems in non-office environments (in order to improve HCI).

Spending the first half of my twenties working my guts out for a big corporation where my efforts went largely unnoticed outside of my immediate sphere. I'm certain that if I put that time into a start-up I would be much better off today -- even if it failed.

I'm kinda curious - is there anyone who doesn't regret their twenties? We've got three posts regretting working for the wrong startup (mine, menloparkbum, and gscott), one working for a big company (yours), one going to grad school (timcederman), one getting a degree (jobeyonekenobi), and one doing nothing (johnyzee). So apparently working for a small company is bad, working for a big company is bad, not working is bad, and getting educated is bad. What should one be doing?

I'm not sure that "What should one be doing?" is the right question. I tend to ask myself that question a lot and I've drawn the conclusion that it's how you do things and what you learn from them that counts.

start a band, buy a bike and travel, get arrested for something stupid, have fun.

I know some folks that did that and regretted it. Well, maybe not the travel part, but I've got various friends that have started bands/gotten arrested/had fun and kinda wish they hadn't.

Graduated with BA in comp.sci at 19 y.o. (not a mistake), then immediately took job doing web support stuff with big (non-tech) company.

In retrospect, I would have loved to look at more options (like starting my own company), but a) I honestly wasn't even aware of the y-combinator sorts of opportunities, b) I was engaged to be married, and felt pressure to be 'stable', and c) didn't think there was anything interesting in my area (and didn't want to leave).

So now (at 22) I'm working on a solo startup solo, in bits and pieces on the side. I just don't want to be like all the 30-year people surrounding me. Or the 10 year people. Or even the cynical, tired person I see myself becoming, all too rapidly ;). Must... not... give... in...

#1 with a bullet: listening to the hype.

I was a National Merit Finalist, honors student, and such. I didn't go out and get scholarships for college. I stayed in-state instead of going out for my own adventure. When I got to college, I didn't know what I was doing with myself and bombed pretty badly. I wasted a lot of time and effort. I didn't drop out to figure things out though. I took out a lot of student loans, and didn't even finish undergrad first time around.

I think a lot of my problem was not biting the bullet and making the hard choices after that first mistake. Instead, I dug myself deeper every time. I'm still paying the loans, but once I figured out what I really wanted, it was not so hard to work to get it.

1) Granting people respect just because they are older than I am.

2) Not moving to San Francisco sooner.

I only respect three things:

* Competence

* Knowledge

* Experience

In that order. In fact, I only really respect the first one, but I've found that the other two can be very strong indicators of the first, and it's generally a bad bet to assume that someone who's clearly more experienced and/or knowledgeable than you on a topic is not also more competent (at least in some way).

I didn't have the guts to ask this one girl out.

I did and she basically spit in my face...

I envy you my friend.

Not listening to my own ideas.

Not playing football in 6th grade. I would have been a completely different person, I believe.

Football meaning soccer or american gridiron? I played the latter and the injuries I took affect me to this day. Back in the day, nobody mentioned the 100% injury rate - i.e. anyone who plays football will eventually get hurt bad enough they can't play. Thus, as I type this from bed, because one of my slipped discs has acted up, I have the opposite opinion - playing football was one of the biggest mistakes I've ever made.

Almost every sport has a 100% injury rate where you eventually get hurt bad enough you can't play anymore. The trick is choosing a sport where the most common injuries prevent you from playing the sport but don't prevent you from walking. A good percentage of swimmers eventually develop shoulder injuries, but (AFAIK) that doesn't prevent you from doing anything except swimming.

maybe the 100% rate is true, but not 100% career-ending injuries.

Most people quit playing a given sport seriously because they have to choose between that and making money.

I swam for 4 years in college and I only know 1 person who had a career ending shoulder injury, and that one because it was misdiagnosed for a year.

OTOH everyone I know who played football at any level has at least a minor nagging injury.

I have played hockey for many years and know quite a few people who have done the same. I can't think of anyone with a long term injury.

I suppose it is reflected in 'old timer beer leagues'. There are a few 50 year old guys on my team right now, and they can play fine they are just slower. Sames holds for baseball.

Even though football isn't that popular here - most of the guys I know that did play with hopes of making it big in the US college system ended up injured.

Yes, football from what I've seen, is far worse than any other common sport. Even rugby is much safer.

That isn't true. It is rare that you would break a leg playing basketball or any bone at all playing baseball. It happens all the time in gridiron football. I wish I could find the chart where I got this information. The strange thing was, if I remember correctly, that the 2nd worst sport was women's soccer, because so many people tore their ACL.

"It is rare that you would break a leg playing basketball or any bone at all playing baseball."

I read somewhere that a lot of baseball players will just call a cab if they have to walk more than a block or two because their ankles are so shot. Not sure if this is true or not though.

That sounds kind of silly. OK, life has a high risk of death, but if sports really are that unhealthy, why pursue them?

Glad to see that even the smart folks at HN are subject to the temptation of mindless diversions.

Focusing on quality rather than volume.

Talking about regrets and mistakes s a funny thing. There is an implied hypothetical there -- like, "If I had made a different choice, I would be a in a better place."

Take, for example, my (admittedly foolish) decision to drop out of the University after a year and go to community college part-time for a year. It should have been a bust, but I ended up meeting my wife (who was working on her generals) there. I met another great friend on my second run at the University. Now my wife and this friend are my co-founders for my startup... both of whom I possibly would've never known if I hadn't gone to the community college.

Now, I'm not saying that there is no such thing as bad choices, or that I have no regrets about things I've done -- I think it's natural for us to regret things that we perceive as mistakes. But I'm pretty happy right now in spite of any problems that I might have, and as far as choices contribute to our happiness, mine have worked out well. It's hard for me to describe choices that have made me happy as "mistakes".

Not launching soon enough and waiting until the product was "perfect".

I think this is in terms of startup mistakes, seeing as how "life mistakes" could start an entirely new forum all together.

Here are my top 3:

1. Wasting money on a legal entity. If you're not making money, you cannot be sued. Wait until you make money or have someone willing to give you money before you waste money on protecting yourself.

2. Bad business partners. Judge your partners not by how much you like them but if they'll complement your skillz, add value to the team, and are dedicated to the project.

3. Not saying no. It's a personal problem, I'm a really nice guy, it's hard for me to say no sometimes, but it's necessary. It's not personal, it's business.

Your #1 item is dangerously wrong. If you're not making money you can still be sued for personal assets (house, car, etc); and if you don't have those, you can be sued for debt.

I'm baffled as to how he could actually believe that. Also, the cost of forming an LLC to insulate yourself against that is trivial.

You cannot get sued for having a site that isnt charging anything because youre not giving any legal consideration. Without legal consideration, there is no contract between you and your user base. Thus, while you technically can still be sued, having that case go anywhere is very unlikely.

Of course if youre doing something legally grey like youtube or file sharing, then perhaps you should incorporate. But without any assets in the company, the corporate liability will most likely be pierced in court.

As for a LLC. Its nice but you should really do a ccorp if youre serious about business, and changing from a LLC to a ccorp is a pain in the butt. Or so I hear.

To go further, I challenge you to show me a single case of a company being sued that wasnt doing something legally grey and not making any money.

Applying your litmus test means that no OSS company has ever been (or will ever be) sued for patent infringement.

It is difficult to have a corporate veil pierced on the basis of assets held alone, and there are specific conditions in place in every state that must be met in order to pierce the corporate veil. Which you've actually argued for yourself in your claim that a C Corp is the entity that you want to use in order to protect yourself from liability, because that is the basis of most of the corporate law in the US.

I just think you're advocating gambling with your personal assets when you could just as easily spend $1000 to $1500 to have a professional set up your corporation and have some level of protection. Additionally, you could throw in a few hundred bucks and insure the new corporation against liabilities. The last time I purchased a policy, it cost me something like $300 a year to carry a $2,000,000 liability policy.

I bet most people starting a startup have spent more than that on the laptop they use.

[Edit: Maybe there is a lawyer who reads YC who can clarify all this stuff for us]

Icey: Do you know ANY open source foundation that has been SUCCESSFULLY sued for damages? Give me ONE example.

At the end of the day. It's financial decision. Think of ALL the startups ever created for the web, the amount of money/time to understand to create the limited liability shelter, and how many of these examples of these shoe-string startups (those without funding or serious traction) actually get successfully sued for damages.

The odds are, very very very very very small. And ok, while my personal advice might not be for everyone. I am currently almost broke, so for me, it makes no difference if they come after my personal assets because I can just file ch. 7, as opposed to the amount of capital and money and upkeep that comes with any form of limited liability.

If you think I'm wrong, digg me down, but note how no one has (1) shown a counter example or (2) has given advice from the standpoint of a seasoned lawyer.

I'm not a historian, nor am I a legal expert, that's far outside my realm of expertise. However, just because I can't personally name an example of that happening doesn't mean that it "cannot" happen.

I was merely pointing out that the advice you were dispensing was risky and negligent. That is still the case; I'm afraid the burden of proof is on you, as you're the one making spurious claims.

"Cannot" is a world of difference from "not likely to".


I totally agree that you should grab some sort of limited liability protection. I am not a lawyer, so most of this stuff is hear-say or just random observations from my, to be honest, limited knowledge of the legal system.

I do know however that setting up a LLC or C-corp WITHOUT any tangible assets, as most string-budget startups are, IS piercable.


That's the specific case that's often cited for precedent in LLC piercing.



If you have any sort of funding, I'd say over $20,000, you should grab some sort of limited liability coverage ONCE you get traction.

But since we're all just guessing about the actual legality of this stuff, why don't we have someone that is an actual lawyer come and put an end to this debate.

You can get sued for many, many things, even if you don't charge users. Copyright infringement comes to mind. YouTube doesn't charge anyone for anything. Any site with user generated content is open to that one.

There are scores of other reasons you might be sued beyond a disgruntled paying customer. To say that you shouldn't spend the couple hundred bucks it takes to set up an LLC is just ignorant.

You've added a sentence to your post regarding requiring an example. What basis would there be for any legal suit if a company wasn't doing anything legally gray? Isn't that the point of a lawsuit?

Negligent tort?

Are you a lawyer?

Is this legal advice?

No. But I have run a c-corporation and I know how hard and unnecessary it is when you don't even have a proper product.

1. too much cocaine. really, it makes you feel like you can conquer anything and anyone, but it is totally not worth it. 2. learning any Windows based programming languages. seriously, what a waste of time.

havent dared to make enough mistakes yet

Be brave! I wanna hear some horror stories! :D

Listening too seriously to others. People like to give "advice" from their perspective and because such advice is through their own lens of reality it might be true for them, but not for you.

Compromising the long-term product vision for short-term gains.

Biggest Regret: Waiting too long.

Examples: I wish I learned to program sooner. I wish I started playing basketball sooner. Etc...

I still find myself doing this, although less now than before.

Quitting work in the physics lab at the University of Florida my freshman year and then switching from a physics and mathematics major to a finance major.

My worst mistakes were in doing what was expected of me, rather than what I wanted to do.

Wow, interesting topic. Some months ago, I started a little (non commercial) website that would do exactly this: ask people what they regret and record it for others.


Not focusing on ideas that interested me, but rather ones that interested others.

try to hold on as much equity as you can

Not having looked for a scholarship to get me to a real university. Now I'm stuck here. I'm in my 4th year (1 more to go), if I transferred I'd be in 2.5 or something.

Not focusing on a single product. We moved into a related sphere because our technology applied, but doing it part-time we ended up shortchanging both.

Given up to early.

Not quitting sooner the startup where I had to learn J2EE.

Majoring in finance.

afraid of making mistakes .

Most of the below!!! (except playing football and doing physics!!)

Sorry to downvote you, but there are no mistakes below your comment. It was a mistake to think HN comments are statically positioned. :)

i still dont understand the how downvoting actually works here... i found i just got downvoted on a different thread for no apparent reason.... what the? oh well such is life :D

I'm good at rolling with the punches, so I haven't yet been smashed by a big mistake, although I've made plenty. I usually recover from those, and come back bigger and badder.

I have, however, lost a lot to the petty time-wasters and energy drains that eventually lead to missing opportunities for growth.

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