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Ask HN: Do you have any startup related regrets? Epic failures?
44 points by makeramen on Aug 2, 2010 | hide | past | web | favorite | 45 comments
I've heard so many optimistic stories of "failed" startups where the founders continue on to new startups, or end up leading better lives afterwards regardless. But the whole time I'm thinking "there's got to be some downside to all this..."

There just seems to be this great optimism within the startup world that even if your idea or company fails, you're still fine, and I'm curious to if anyone has any stories of that not being the case.

Where are the startup stories of terrible regrets and failures? Is there anyone who's said "I wish I never tried that" or "those years were a waste of my life?" and why?

I've just found the startup industry to be extremely optimistic about things, and with so much attention on all the epic successes, I'm looking for some truly epic failures; mainly to keep my feet on the ground and in touch with reality.




My regrets are mostly rooted in trusting the wrong people (against my gut feeling too!) and not speaking my mind when I should have. I've written about it and I hope that by doing so I can save other people some of the hardship and the frustrations that go with that.

I got out with my hide in tact but it damaged my relationships with a lot of people that I care about beyond recovery and it changed my personality in a measurable way.

The difference between success (selling out to the tune of > $10M) and 'failure' (keeping the company alive for the next decade) was a couple of weeks in timing. Too bad, but it didn't really change my outlook on life, as they say, it's only a done deal when the money is in the bank.

My partners in the business didn't survive that blow, so I ended up going the rest of the distance as the sole shareholder with those employees that stayed on.

If I had to do it all over again I would be much more careful who I'd bring on board and I would keep a much better eye on things. I doubt I have the energy for yet another run though, these days I'm happy enough helping newcomers to gain a foothold and to speak my mind without any regard for the consequences. Life as a starter-upper is like living in a very large fishbowl filled with sharks, and you, the lonely goldfish in the middle. If that's not your view and you're a start-up 'CEO' congratulations, you either have the right people around you or you haven't had any real adversity aimed at you (yet, and hopefully it will stay that way).


Entrepreneurs can see the silver lining in the worst situations. They can fail, but then stand up, brush themselves off, and say "next" without skipping a beat.

That being said, I could say that I wasted money on some bad investments, and I spent months too long on side projects that resulted in nothing....... BUT even the worst decisions I've made HAVE paid off in some way.

I made life-long connections with great business people, I learned about an industry I was unfamiliar with, I learned about the building blocks of business by losing that investment money.

See, it's just impossible. If you are going to be in business, you don't dwell on things, you constantly forge ahead.

All my failures made me smarter, faster, brighter, and a better person.


I ran a startup during the late 90's early 2k. I got a payout at the end but I worked so hard building the business that I burnt myself out. The following years I was brain dead and not productive. I called myself retired in my 20's but in reality I was just tired. If I paced myself for all those years I might have been in a better place afterwards.

Though, to be honest, it's just not in my blood to pace myself. I'm an entrepreneur because I love to go for it. I am all in all the time. It's just my nature.

Today my brain is turned back on and I'm going full steam. Yes, I might burn out again but I wouldn't feel alive if I wasn't all in.


To be clear, I regret pushing so hard that I let myself burn out. Even though I'm working long hours again, I'm being careful not to repeat my burnout.

There are times I don't feel like taking a break but I do anyway. If I've been working on the same thing night and day then I'll stop and work on a fun project that's not related.


Just to clarify, by brain dead do you mean you had lost motivation or weren't mentally able to be productive?


I lost motivation completely. I didn't want to work. I couldn't come up up with any new ideas. I had little interest in anything.

Like a total void.


What boosted you back up? Maybe you just needed a time-out?


Yes. Mostly time to get interested in the industry again and then to get back into the swing of things. The first few projects were rough but each new project was written better and faster.


Startup 1 (HavenCo): I regret not being "incrementalist" enough -- should have had a plan for $200k, $500k, $1m, etc., not a plan for $5-10mm in spend. I'm still not sure if it would have ended up any differently, but it might have been technically more interesting along the way.

Startup 2 (Iraq): I regret not vetting employees, and on relying on dishonest/criminal people. This killed a $50-100mm business.

In both cases I regret not properly separating my personal and business fiances, such that I was broke (or ~$200k in debt) after each. I ended up having to do boring consulting for a couple years to stay above water, after each.

For Startup 3, I've set aside a year of personal money which I won't touch, and am only working with people I trust -- I pretty much picked this of 2-3 other opportunities based on the skills of people I know and trust. I'm going for outside investment, even though it isn't absolutely essential, to enforce greater financial/reporting/fiduciary discipline, and to get really smart people involved -- I don't think advise from someone who won't invest is worth anywhere near as much.


Did you run a startup in Iraq or did it have some special connection to there? What was that like? I often think there are probably huge opportunities in (relative) chaos but it takes a special person to see them (and to be gutsy enough to go after them).


In Iraq.


A classic example: Xanadu - http://www.wired.com/wired/archive/3.06/xanadu.html

It was the most radical computer dream of the hacker era. Ted Nelson's Xanadu project was supposed to be the universal, democratic hypertext library that would help human life evolve into an entirely new form. Instead, it sucked Nelson and his intrepid band of true believers into what became the longest-running vaporware project in the history of computing - a 30-year saga of rabid prototyping and heart-slashing despair. The amazing epic tragedy.


From that short description, the product sounds a bit like Wikipedia :)


What about success regret? I've said before that I shouldn't have sold when I did.


I don't think one should speculate about what the outcome would be if you had done something differently. Instead, it's best to determine what you are going to do next time which is different from the last time.


This is very excellent advice.


What could an investor or board have done to have gotten you to agree with this back then? Offered $5-10mm cash off the table in another round?


No clue. Our potential series B was smaller than that, so it wouldn't have been possible.


Then how does one identify the right time to sell, or rather whether or not to sell?


Can you elaborate?


He sold a vibrant, viable business to...yahoo. Enough said.


Can you elaborate on viable? Is there many bookmark websites that are making the cut nowadays?


Given that it had pretty good traction as a bookmark site (and certainly wasn't the only project joshu had developed...actually several of the others were more interesting), it's very reasonable to believe it would have evolved into something different from what it was when sold. At Yahoo, it stagnated, just like every other acquisition Yahoo has made (Flickr is probably the most similar).


Partner Selection: The person I chose to partner with on my startup is a great human being, but not cut out for being a startup partner. Not everyone is cut out for this and even people like pg have trouble determining who's got the determination and who doesn't. Next time I'll pick somone who is technical (this person wasn't) and determined and who loves this stuff as much as I do.

Industry Selection and (effectively) going it alone: My first startup was something I could code in the evenings myself. The good news is that I actually got a functioning freemium service to work on my own with (too few) real customers. The bad news is that the ease of coding also meant that a lot of people had written similar sites. The barriers to entry were just too low. The good news: Coding the whole service from the CSS to the SQL taught me a lot about coding that years of corporate work never did.


At foo camp I usually run a session called "that sucked" in which people share failure stories and I tally the root causes. Thais year the worst were both "going with your gut" and "not going with your gut"


If you back those out (assuming that they had equal subscription so could be a random variable), what were the next two reasons?


Actually the causes differ every year. Often the main issues are unicode and mysql.


what exactly about unicode and mysql?


They inevitably conspire to fuck you up, somehow.


It's hard to say you have any regrets when you try to see every failure as a learning experience.

Having said that, I have in the past also wondered why we don't focus more on other startup failures as a source of learning.

The first reason I believe is because most of the epic failures you see come down to more or less the same reasons: founder/management troubles and/or no market. If most failures can be boiled down to that, there isn't a lot to learn from each new failure. However, each time there is a success, it is usually for different reasons and there is a lot to learn.

The second reason is why entrepreneurs are usually so forward-focused: you usually do not find a new paths by looking backwards. You learn from your mistakes and you try again. Looking backwards only shows you what others have done, and those are almost always opportunities that have already been realized.

You know you are in a promising place as an entrepreneur when the mistakes you make are because you are trying things nobody has ever tried before, as opposed to making the same mistakes others have already made.


Selection bias is perhaps your problem. The people talking are still trying or succeeded.

That said, if you want a story of failure, I spent a year working on a startup idea, spent a large chunk of my savings and ended up scrapping it, it never got finished or even launched. Much of the reason for spending so much time on that one idea was because I took a Master's degree in Entrepreneurship and it was part of the curriculum to write a business plan and try and start a company.

If I had a second chance, I would have saved 5 figures worth of savings and done it a lot leaner and pivoted to other ideas which had a better chance. However, the way the program was structured, there was a certain lock-in which meant degree or startup in a sense.


I failed Zden.com in 2002 (launched in 2000). Regrets turned into positive(?) lessons (I hope one day I can say that).

* When you are doomed, you are doomed. Better to start over than try to fix.

If there is good chance that the reason why you do not get traction is mono-dimensional (eg. just the UI or (exclusive) just performance...), it seems ok to go on & try to tweak it, but if you it is multidimensional (several reasons) (Technology, management, wrong market assumptions), then pull the plug ASAP. I did not have the guts to cut 3 fingers, so reality took my arm.

* Even if others "co-founders", I was alone (CEO with masteroftheuniverse equity stake), I had just came back from a 99 boiling BayArea startup, there was a wrong "guru" effect: no real co-founder (especially hacker) to tell me "this is wrong, you are kidding yourself". Selfcomplacent, mono thinking: doomed.

* Focus, focus, focus: you have to make hard choices so that you will NOT do X,Y,Z in order to become better at U. Not only experienced it for Zden, but another company I have worked (could have gone further quicker) for they did not have the balls (at least for 9years) to cut off either distractive product/features, or market sectors that are not going anywhere while another is booming etc. "Everything for everybody": doomed

* Do not impose new behaviors on users/prospects (or just a super light one maybe) (worst is several at the same time). Users/prospects do not care about you & your service (by definition). We added complexities on top of another by introducing too many new "innovative" things (we thought) at the same time and users "just had" to do x... (1/ a new micro-currency, Zees instead of using plain dollars, 2/ the fact that people could sell or share their files (ecommerce + heavy bandwidth issues), 3/ that they had to classify their files in categories themselves (taxonomies spamming, low value content). Compounding complexities (for users/prospect or in general): doomed

Learnt that simplicity is very hard, it is an humbling ego bruising discipline.

* Do not accept to meet a VC (or key account etc.) overnight. You need to get prepared. Eg. Almost went the next day after to meet for my 3rd meeting Benchmark capital (after the 2nd they let me so much wait that I accepted meeting right away) and... got burnt. I would have studied John Newton bio (EIR at that time which I was meeting), I'd have discovered that a co he co-founded Documentum, he learnt the hard way about the necessity of a "Crossing the Chasm" (Geoffrey Moore) plan. Even after getting extra 5mn of his attention in the corridor, no Beachhead market focus: toast.

Show you are strong, do not say "yes" right away, successful people have busy agendas, any relevant professional will respect that.

* Finally, do not believe that by "believing in it so hard, (like in "against all odds/we believe/success" movies) in the end you will not fail". You can fail. One could say that as entrepreneurs that is our destiny (http://www.youtube.com/watch?v=45mMioJ5szc). That should always be a possibility in your head. "Will I?" creates better outcomes than "I will" study shows: http://www.psych.illinois.edu/~dalbarra/pubs/Wll%20I%20I%20w...

Outcomes of this not expected failure (before I always thought I had a good angel watching over me): I really thought all my juice was gone forever. But then I accepted, I failed, it was nobody else's fault. I just had to shut up. Restarted from scractch (literally zero, zip, nixs cash, I had invested evthg I had, was too ashamed to ask anybody for help) with 1st new non-CEO job which was... putting advertisements in thousands of mail boxes (for real, I worn shoesoles out!), to find realestate properties to sell, and then made my way up from there, one step at a time w/ the help of luck and others (that I thank).

Bottom line, took me 8 years to earn the right to tell the world this:

In the few coming weeks, we will launch another company. We are 2, I am the hustler, Francis he is the Hacker, and together... we are going to kick ass !! ;)


Thanks for the insights. I can see that you're the hustler busting your balls trying. Get rich or die tryin'! Keep it going, and good luck!


lol, you sound wired! Get some sleep ;)

Best of luck on the new company!


Trying to do way too much (Why did we build blogs/videos/images/forums for a blogging site whose unique feature was game mechanics/points for blogs?) and waiting too long to release (Why did we wait until EVERYTHING was done to release it only to find that people only used 10% of the aforementioned features).

All of my mistakes boil down to one of these two things.


My biggest regret was folding up in 2007, shortly after ec2 came out. I'd be two years ahead if I stuck with it rather than pulling a Ross Perot.

details: http://www.kuro5hin.org/story/2007/12/7/3649/26418

just think how much further along I'd have been if I didn't own goal that one?


Try not to do things outside your expertise or your team's. I've found it more of a disadvantage and playing catch up than the idea of bringing a fresh perspective into the mix. It does depend but you either need to be able to test your ideas quickly or have a lot of time.


my only regret is not having the guts to take the plunge and really dive into an idea and see it through from conception to reality. The internet taunts me everyday with news of successful startups and even ones that failed, I failed to even achieve this.


Entrepreneurs are inherently optimists. They have to be, otherwise they'd give up, get a job, and not bother sharing their stories of failure. That's why what we see is weighted positively.


I'm very well aware of that, but sometimes I feel like I get too optimistic about things and need a reality check. That's basically all I'm asking for here through hearing failure stories.


Not epic but I made the mistake of rebranding and relaunching after getting some seed funding. As a result I'm doing things very differently this second time around.


And your rebranding was a mistake?



My only regrets are the ideas I don't bring to completion, especially if someone else ends up executing on something similar.


Lots of failures, a few epic.

No regrets.




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