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Confessions of a 20-Something Startup CTO

100 points by BenjaminCoe 14y ago

makmanalp 14y ago
>I’ve always struggled with confidence issues. As a way of compensating for this, I leaned on my programming licks; here was at least one thing that I was awesome at. >When I got into the startup world, something shocking happened. I started to meet people who were my equals, or even worse, better than me! This caused an existential crisis. Spot on. It's not just you, buddy. Edit: Contrary to popular naysaying, there are some of us who do like reading about others' trials and errors. I also loved the article on rock climbing. Keep it up!
chayesfss 14y ago
Ahh, I remember when I was 20 & how nice to think what you have to say is important. I've personally found that people want to read about functionality. They might want to read about your personal stress after you've become successful but chances they're more interested in reading about a new integration or how to look at something different.
heretohelp 14y ago
I'm a 20-something startup CTO, why do I want to read the thoughts of people my own age instead of people who are more experienced?
- BenjaminCoe 14y ago
  I was just trying to write an honest reflection on what my experiences have been like, diving head first into the startup world. I'm not trying to position myself as an expert :)
  - heretohelp 14y ago
    I guess the problem is that we have tons of wantrepreneurs and first-time startup kids posting about their feelings here. It's a multiple-times-daily thing. Seriously. What we don't seem to get very much of is more experienced (serial entrepreneurs, experienced programmers, etc.) individuals posting anything with with the same depth in terms of substance or how personal it is. The degree to which Hacker News has become homogenous in terms of contributed content is disturbing. Edit: Let me be more specific. You want to know what content is? patio11. That's value right there. His stuff is gold and could legitimately help you get your product off the ground. Another example would be Rands in Repose (Lopp). His twitter feed is the most self-indulgent bullshit I've ever seen, but his blog posts can be instructive for how to lead a technical team and work with other people in general. To put content out into the ether for your own edification is all well and good, but the moment you promote it on a public community like Hacker News, you are making a particular declaration about what sort of value you're purporting to provide. Value, not personality. Save the personality stuff for people not trying to build stuff. Also, your tumblr is broken if you google yourself. Might want to fix that.
    - justsee 14y ago
      You seem to have a very strong opinion of what HN should be about, and yet this bubbling animosity for the OP and his content seems very out of place here. The post's title was completely accurate, to the extent that you've admitted it's not something you want to read. Don't read it then. The fact it's bubbling up the top posts means others found some merit in it. You want to lecture people against upvoting this content based on your personal reaction and needs, and feel compelled to fling about terms like 'wantrepreneurs', 'kids', 'self-indulgent bullshit'. I'd prefer not to have to wade through comments full of seething resentment and antagonism, but I'm not going to lecture about it, because most HNers would find it very boring. I'm a decade ahead and found the post a nice little read - seeing someone realise the importance of striving to find a balance. I like hearing notes from the ground from people at all stages of entrepreneurial activity. Hacker News is not Hacker News From More Advanced, Insightful, Intelligent People Than Yourself At This Current State. That's a good thing.
      - heretohelp 14y ago
        Although I disagree with PG on nearly everything salient to this conversation, he himself has noted the decline of the community here. I'll take his word for it over yours.
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        heretohelp 14y ago
        Wow, I'd never seen that comic before. http://i.imgur.com/AfLMo.jpg http://i.imgur.com/AfLMo.jpg Edit: Original context: BenjaminCoe decided to reply to me with the xkcd comic referencing the, "Someone is wrong on the internet" thing. He has since deleted his comment without explanation.
        14y ago
- untog 14y ago
  Why do you think the article was written for you personally?
  - heretohelp 14y ago
    The point is that even people in the same cohort aren't seeing the value, how is it going to help everybody else?
    - deleted 14y ago
      [deleted]
    - dannyr 14y ago
      Maybe no value to you but it is for me. Probably for other people too. Please do not draw generalizations just based only on your own experience.
      - yay_cloud 14y ago
        I think there's also value here watching heretohelp flail about unprofessionally. He may have valid points or not, but the truth is, it doesn't matter, because he's going about his crusade in a way that will turn most people off. His conduct doesn't cast nutrivise in a great light.
- WadeF 14y ago
  A lot of times people more experienced are so far detached from what you might be going through. I've found people who have just gone through what I've gone through can help a ton. Joel Gascoigne sums this up better than I. http://joel.is/post/28198804700/why-im-helping-startup-founders http://joel.is/post/28198804700/why-im-helping-startup-found...
  - larrys 14y ago
    "A lot of times people more experienced are so far detached from what you might be going through." Some of those people may have gone through the same and can offer their opinions of how it worked out for them. Have you ever had a medical problem and asked an older person about it? They might tell you "don't worry I had that same pain and it went away, no biggie". Don't assume someone older has no experience or empathy to what someone younger is saying.
    - WadeF 14y ago
      I wasn't. Just simply trying to provide a perspective on why someone younger might also have valid advice. Life doesn't have to be one or the other. :)
  - heretohelp 14y ago
    Potentially interesting but irrelevant point. The post is thin whether you think old people can't relate to the special-snowflake problems of the modern startup kid or not.
- mbesto 14y ago
  I'm not sure I quite follow your logic. I can't figure out if you're asking a rhetorical question (and thus trying to make a point) or you generally are questioning your own self? If it's the former, I'd suggest you a be slightly more direct about what point you are trying to make. Alternatively simply just upvote or ignore the story all together.
  - heretohelp 14y ago
    I'd rather make a point about the content here and hopefully inspire somebody to contribute something founded on somewhat more experience. Contrast: the foursquare founder interview, while not great, was more useful.
- dinkumthinkum 14y ago
  Maybe pay special attention to the part about humility. :)
  - heretohelp 14y ago
    Maybe seek to understand the original comment and ask the questions necessary to eliminate the disparity of your perception and the meaning intended to prevent yourself from making a totally pointless comment. Your response is pointless. Just downvote me next time instead of polluting the thread. Or be productive and ask me why I said what I said like the others have.
    - puppymaster 14y ago
      Why should it be the responsibility of the majority to ask for clarification when you come off as an arrogant poster in the first place? If you don't want to be misunderstood, rephrase your wordings. Now you find yourself having to explain your position instead of getting an intelligent discourse out of the corresponding thread.
    - dinkumthinkum 14y ago
      :) You're projecting.
- larrys 14y ago
  Well for one thing because people more experienced read posts like this and give their thoughts and opinions.
  - heretohelp 14y ago
    That doesn't seem to happen much in practice and when they do post, wantrepreneurs bicker with them and scare them off. Instead it's mostly cultural jingoism and blind cheering.
- pbiggar 14y ago
  I hope you don't take this the wrong way, but that's a real dickish thing to say. Imagine saying that to a colleague or someone at a party! "I'm sorry but you are too young to have valuable opinions". TL;DR: don't be a dick
  - heretohelp 14y ago
    It has nothing to do with age, you've totally misunderstood my point. My point is that if the post seems pretty thin to somebody from the same cohort, how could it help anybody else? I'd rather see either 1. More substantive content, less "here are my feelings about being a startup kid" 2. Something from people who've spent more time at this and developed deeper people skills. Could even be somebody the same age, just more experienced. tl;dr don't call somebody a dick unless you actually understand the point of their comment.
    - pbiggar 14y ago
      If I misunderstood your point, it is because you did not make it well. From your comment, all I see is a dismissal of the post because it has nothing to offer you. Your last comment is much more substantive - perhaps you should have said that the first time.
      - heretohelp 14y ago
        I definitely didn't communicate it well. The deeper issue is that I wish I could borrow 20% of HN users for some other environment or somehow combine curation with timely conversation (hard to do).
awm 14y ago
Could you elaborate on what you mention is the MIT syndrome? I saw one definition (based on over explaining) but it seems like this is something else
- GuiA 14y ago
  Students entering MIT are the ones acing every class, being constantly praised by teachers/parents and feeling better than everyone else in high school. Then they enter MIT, where they find themselves with hundreds of fellow students just like them. For a lot of personalities, this leads to depression and even in some instances suicide.
  - Xcelerate 14y ago
    I would think the fact that they are one of hundreds out of billions would inflate rather than deflate the ego.
    - mquander 14y ago
      That doesn't make sense. People emotionally calibrate themselves against the visible skills of the people in their peer group, not a global distribution of IQ.
      - Xcelerate 14y ago
        Yeah, I know they do that, but it doesn't make sense to me why they do that. If everyone expects to be #1 in the world, everyone but one person is going to be disappointed.
        GuiA 14y ago
        Go tell that to 18 year olds :)
        ajdecon 14y ago
        It's not a rational thing, but more instinctive. Your immediate surroundings influence you in all sorts of unconscious ways, but all the people in that global distribution are pretty abstract. You can quote statistics all you like, it's difficult for them to change how you "feel" about yourself. Also http://en.wikipedia.org/wiki/Dunbars_number http://en.wikipedia.org/wiki/Dunbars_number
electronous 14y ago
This article might have a good point, but it's hard to find it amongst all the "my friends and I are really cool and awesome people" speak. Does this article, coupled with the fact that the author submitted it himself, strike anyone else as terribly vain?
- GuiA 14y ago
  Welcome to HN, where everyone is a rockstar entrepreneur!
- prezjordan 14y ago
  "His interests include climbing, coding, and being awesome." :( Maybe it's tongue-in-cheek, but still.
tkiley 14y ago
The "MIT syndrome" thing is crucial. I think the most important trait in a startup leader is humility. To build a kick-ass sustainable company, you absolutely, positively must be comfortable working with people who are (in some or most respects) smarter than you. Also, I find it very interesting that the "high" of this roller coaster is the funding.
- dkrich 14y ago
  I never understand why funding seems to be the end goal either. To me, apart perhaps from some vindication of your idea, the happiness people experience when funded almost shows a lack of vision.
  - BenjaminCoe 14y ago
    For people with financial burdens, venture capital can be the difference between being able to pursue your startup dreams, or letting them die on the vine. There are definite downsides to raising money, and I totally understand the stigma the HN community tends to attach to it. Having said that, a 500k seed investment let Jesse and I put down everything, and put 100% of our efforts towards Attachments.me. I have no regrets about this.
    - dkrich 14y ago
      I'm not debating the merits of raising cash. Most companies and businesses have to do it when starting out. The part that I (and I'm assuming the OP) find puzzling is the part about "climbing to the top of the hill overlooking the city and realizing all our childhood dreams had come true" after having raised a round of investment. This seems to me to be saying "we got a million+ investment and we won!" I think for most that's not really the point of starting a business.
- mkramlich 14y ago
  I'm trying very hard to avoid the "success if getting investment" path because I think it's an anti-pattern, which in turn leads to other anti-patterns. It's much much better to get funded initially out of your own pocket, and then next out of customer's pockets. The earlier you get a real customer who pays you for what you give them, the earlier you validate your business/product, and you indeed have a real business, with effectively an infinite runway.
hkon 14y ago
I think IT is more like confessions on anyone starting out at anything. Tanks for verifying what carnegie said.. 100 years ago ;-)
k33n 14y ago
Thanks for writing this. As a 20-something startup CEO, I frequently want to write about something mundane (or not) but often choose not to for reasons of confidentiality or that I worry some things will cause problems for me later. I don't think I'm a startup god, or an expert at all. Sometimes it would just help to vent or have a discussion about something with strangers who are in similar positions as me. Unlike some of the other commenters here, your post didn't strike me as self-important. Just looked like you felt like sharing and wanted to have a dialog.
larrys 14y ago
"I began getting depressed about the lack of a life I had outside of work. I’d bring this bad mood to work with me, in turn making it a worse place to be. I’ve since made an asserted effort to dedicate time to my social life: going on trips with friends; going on dates; and, most importantly, getting work completely off my mind occasionally." Serious question (and my thoughts) here I'm not trying to be cute. Regarding your "social life". Do you think you will grow out of this? Because what do you think is going to happen if/when you are married and have children and aren't living in SF or some exciting place and have much on your plate? The best way to insure that you can live the life you want and have some fun is to put all the effort in that you can now and try to put off having fun until a bit later on. Now is when you have energy and should be able to work non-stop with very little else. (I didn't surface for air for 7 years working 6 to 7 days a week ..) I point this out also because the world is littered with people who didn't get into a good school because they spent a bit to much time worrying about missing something or having fun and are paying for that later. I'm sure you've met people like this in your high school. It's a little unclear how long you worked before you realized what you wrote. It was certainly less than two years since you wrote this: "I’ve grown a lot as a person in the past two years." That's not a long time to be denied the pleasures of other people and fun (look at people on tours of duty in the war or speaking of my own experience). The fact that you never had a problem until later means you really haven't dealt with the situation you are in now in the past which I think is what you are saying. Things were easy for you until you got around a group of people who were also good. I know first hand about the MIT syndrome since I saw others that suffered from it at the school that I went to which was quite good. I didn't suffer from that for one simple reason. Things were never easy for me it always took hard work and it also took plenty of effort for me to get into the school I went to. So when I got there I didn't fall apart if I got a "B+". I just kept chugging away while the ones who were "so much smarter" who got in with their top grades and SAT's wilted under the pressure of having to do so much work. This was a long time ago compared to when you are in school. So to answer your question, no, things haven't changed that much. You've got plenty of time to have fun. Now is the time to work as hard as you possibly can with minimal breaks in order to achieve your goals. You might not surface for air for a few years but it will probably be well worth it. One last thing. There will be times in life when you might have some crisis either in personal life or business that will require you to work all the time. I had a case where several of my top people left, I was in the middle of a legal case, and a breakup, and I still had to show up to work doing the job of three people and deal with personal issues and family fights. Having to go through that and knowing I could (similar I'm sure to having climbed a certain mountain like you are doing) was a great experience that made me realize that I didn't have to be scared of the unknown and that I could handle it.
wensing 14y ago
When you say that "Bootstrapping a startup is stressful", are you only referring to the time before you raised the $2.5 million? How long was that? EDIT: According to CrunchBase you raised $500K two months after your company was founded, and another $2 million 13 months later. I'm sure you just used the word without thinking much about it, but technically you bootstrapped for all of 8 weeks. :)
- ojbyrne 14y ago
  Sometimes people work on things before they found a company around it.
- mirsadm 14y ago
  I hope there is more to this.8 weeks is like an extended holiday. I've been bootstraping for a year now and yes it is difficult but not that difficult.
- modarts 14y ago
  Why is there this overwhelmingly anti-bootstrapping sentiment present in the startup community? What's so wrong with taking outside funding?
  - j_col 14y ago
    If you take outside funding, you're not bootstrapping. According to Wikipedia: "Bootstrapping in business means starting a business without external help or capital." Source: http://en.wikipedia.org/wiki/Bootstrapping#Business http://en.wikipedia.org/wiki/Bootstrapping#Business There is nothing wrong with taking outside funding, but then you don't get to call it bootstrapping any more (as per the widely-accepted definition above of what the term means). This is mixing up terms.
    - modarts 14y ago
      I should have clarified that I was trying to ask a more general question as to why bootstrapping is seen as a superior way of starting a company as opposed to taking on funding.
dennisgorelik 14y ago
I don't see much traction here: http://siteanalytics.compete.com/attachments.me/ http://siteanalytics.compete.com/attachments.me/ It looks like aqui-hire is the best option for attachments.me
- jskopek 14y ago
  That's a little harsh of you, and totally unwarranted. The site's user-base has absolutely nothing to do with the article or current conversation.
  - dennisgorelik 14y ago
    Are you saying that credentials of the author have nothing to do with the article he wrote? I think it brings important context. Besides, the harsh part is lack of traction, not me pointing to it. Don't kill the messenger.
- BenjaminCoe 14y ago
  Our main products are a Chrome Extension, and an iPhone application. The website itself gets a, granted small, but growing amount of traffic -- but it's mainly just there to direct people towards the clients. I don't think that Alexa or Compete do a perfect job of reflecting our usage numbers, since the website itself is not the main way people interact with us.
  - dennisgorelik 14y ago
    1) Compete shows downtrend for attachments.me I understand it could be a mistake due to low numbers, but still does not look promising. 2) What are attachments.me actual usage numbers today and 1 year ago?
    - BenjaminCoe 14y ago
      I won't give you all of our numbers, but If you look at our Chrome Extension page, you can see that we have 35,000 active installations. Much of this growth has happened over the past six months. These numbers simply aren't well reflected in the Compete score. My coworkers and I work hard, and believe in what we're doing. Rome wasn't built in a day, let's hold of on the talent acquisition talk ;)
fellowshipofone 14y ago
Thanks for the post; running a company is not only about making the right decisions, it is also about living with the bad ones. I think this blog post is a good testimony that helps with that.

100 points by BenjaminCoe 14y ago

>I’ve always struggled with confidence issues. As a way of compensating for this, I leaned on my programming licks; here was at least one thing that I was awesome at. >When I got into the startup world, something shocking happened. I started to meet people who were my equals, or even worse, better than me! This caused an existential crisis. Spot on. It's not just you, buddy. Edit: Contrary to popular naysaying, there are some of us who do like reading about others' trials and errors. I also loved the article on rock climbing. Keep it up!

chayesfss 14y ago

Ahh, I remember when I was 20 & how nice to think what you have to say is important. I've personally found that people want to read about functionality. They might want to read about your personal stress after you've become successful but chances they're more interested in reading about a new integration or how to look at something different.

heretohelp 14y ago

I'm a 20-something startup CTO, why do I want to read the thoughts of people my own age instead of people who are more experienced?

BenjaminCoe 14y ago
I was just trying to write an honest reflection on what my experiences have been like, diving head first into the startup world. I'm not trying to position myself as an expert :)
- heretohelp 14y ago
  I guess the problem is that we have tons of wantrepreneurs and first-time startup kids posting about their feelings here. It's a multiple-times-daily thing. Seriously. What we don't seem to get very much of is more experienced (serial entrepreneurs, experienced programmers, etc.) individuals posting anything with with the same depth in terms of substance or how personal it is. The degree to which Hacker News has become homogenous in terms of contributed content is disturbing. Edit: Let me be more specific. You want to know what content is? patio11. That's value right there. His stuff is gold and could legitimately help you get your product off the ground. Another example would be Rands in Repose (Lopp). His twitter feed is the most self-indulgent bullshit I've ever seen, but his blog posts can be instructive for how to lead a technical team and work with other people in general. To put content out into the ether for your own edification is all well and good, but the moment you promote it on a public community like Hacker News, you are making a particular declaration about what sort of value you're purporting to provide. Value, not personality. Save the personality stuff for people not trying to build stuff. Also, your tumblr is broken if you google yourself. Might want to fix that.
  - justsee 14y ago
    You seem to have a very strong opinion of what HN should be about, and yet this bubbling animosity for the OP and his content seems very out of place here. The post's title was completely accurate, to the extent that you've admitted it's not something you want to read. Don't read it then. The fact it's bubbling up the top posts means others found some merit in it. You want to lecture people against upvoting this content based on your personal reaction and needs, and feel compelled to fling about terms like 'wantrepreneurs', 'kids', 'self-indulgent bullshit'. I'd prefer not to have to wade through comments full of seething resentment and antagonism, but I'm not going to lecture about it, because most HNers would find it very boring. I'm a decade ahead and found the post a nice little read - seeing someone realise the importance of striving to find a balance. I like hearing notes from the ground from people at all stages of entrepreneurial activity. Hacker News is not Hacker News From More Advanced, Insightful, Intelligent People Than Yourself At This Current State. That's a good thing.
    - heretohelp 14y ago
      Although I disagree with PG on nearly everything salient to this conversation, he himself has noted the decline of the community here. I'll take his word for it over yours.
      - deleted 14y ago
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      - deleted 14y ago
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        heretohelp 14y ago
        Wow, I'd never seen that comic before. http://i.imgur.com/AfLMo.jpg http://i.imgur.com/AfLMo.jpg Edit: Original context: BenjaminCoe decided to reply to me with the xkcd comic referencing the, "Someone is wrong on the internet" thing. He has since deleted his comment without explanation.
      - 14y ago
untog 14y ago
Why do you think the article was written for you personally?
- heretohelp 14y ago
  The point is that even people in the same cohort aren't seeing the value, how is it going to help everybody else?
  - deleted 14y ago
    [deleted]
  - dannyr 14y ago
    Maybe no value to you but it is for me. Probably for other people too. Please do not draw generalizations just based only on your own experience.
    - yay_cloud 14y ago
      I think there's also value here watching heretohelp flail about unprofessionally. He may have valid points or not, but the truth is, it doesn't matter, because he's going about his crusade in a way that will turn most people off. His conduct doesn't cast nutrivise in a great light.
WadeF 14y ago
A lot of times people more experienced are so far detached from what you might be going through. I've found people who have just gone through what I've gone through can help a ton. Joel Gascoigne sums this up better than I. http://joel.is/post/28198804700/why-im-helping-startup-founders http://joel.is/post/28198804700/why-im-helping-startup-found...
- larrys 14y ago
  "A lot of times people more experienced are so far detached from what you might be going through." Some of those people may have gone through the same and can offer their opinions of how it worked out for them. Have you ever had a medical problem and asked an older person about it? They might tell you "don't worry I had that same pain and it went away, no biggie". Don't assume someone older has no experience or empathy to what someone younger is saying.
  - WadeF 14y ago
    I wasn't. Just simply trying to provide a perspective on why someone younger might also have valid advice. Life doesn't have to be one or the other. :)
- heretohelp 14y ago
  Potentially interesting but irrelevant point. The post is thin whether you think old people can't relate to the special-snowflake problems of the modern startup kid or not.
mbesto 14y ago
I'm not sure I quite follow your logic. I can't figure out if you're asking a rhetorical question (and thus trying to make a point) or you generally are questioning your own self? If it's the former, I'd suggest you a be slightly more direct about what point you are trying to make. Alternatively simply just upvote or ignore the story all together.
- heretohelp 14y ago
  I'd rather make a point about the content here and hopefully inspire somebody to contribute something founded on somewhat more experience. Contrast: the foursquare founder interview, while not great, was more useful.
dinkumthinkum 14y ago
Maybe pay special attention to the part about humility. :)
- heretohelp 14y ago
  Maybe seek to understand the original comment and ask the questions necessary to eliminate the disparity of your perception and the meaning intended to prevent yourself from making a totally pointless comment. Your response is pointless. Just downvote me next time instead of polluting the thread. Or be productive and ask me why I said what I said like the others have.
  - puppymaster 14y ago
    Why should it be the responsibility of the majority to ask for clarification when you come off as an arrogant poster in the first place? If you don't want to be misunderstood, rephrase your wordings. Now you find yourself having to explain your position instead of getting an intelligent discourse out of the corresponding thread.
  - dinkumthinkum 14y ago
    :) You're projecting.
larrys 14y ago
Well for one thing because people more experienced read posts like this and give their thoughts and opinions.
- heretohelp 14y ago
  That doesn't seem to happen much in practice and when they do post, wantrepreneurs bicker with them and scare them off. Instead it's mostly cultural jingoism and blind cheering.
pbiggar 14y ago
I hope you don't take this the wrong way, but that's a real dickish thing to say. Imagine saying that to a colleague or someone at a party! "I'm sorry but you are too young to have valuable opinions". TL;DR: don't be a dick
- heretohelp 14y ago
  It has nothing to do with age, you've totally misunderstood my point. My point is that if the post seems pretty thin to somebody from the same cohort, how could it help anybody else? I'd rather see either 1. More substantive content, less "here are my feelings about being a startup kid" 2. Something from people who've spent more time at this and developed deeper people skills. Could even be somebody the same age, just more experienced. tl;dr don't call somebody a dick unless you actually understand the point of their comment.
  - pbiggar 14y ago
    If I misunderstood your point, it is because you did not make it well. From your comment, all I see is a dismissal of the post because it has nothing to offer you. Your last comment is much more substantive - perhaps you should have said that the first time.
    - heretohelp 14y ago
      I definitely didn't communicate it well. The deeper issue is that I wish I could borrow 20% of HN users for some other environment or somehow combine curation with timely conversation (hard to do).

awm 14y ago

Could you elaborate on what you mention is the MIT syndrome? I saw one definition (based on over explaining) but it seems like this is something else

GuiA 14y ago
Students entering MIT are the ones acing every class, being constantly praised by teachers/parents and feeling better than everyone else in high school. Then they enter MIT, where they find themselves with hundreds of fellow students just like them. For a lot of personalities, this leads to depression and even in some instances suicide.
- Xcelerate 14y ago
  I would think the fact that they are one of hundreds out of billions would inflate rather than deflate the ego.
  - mquander 14y ago
    That doesn't make sense. People emotionally calibrate themselves against the visible skills of the people in their peer group, not a global distribution of IQ.
    - Xcelerate 14y ago
      Yeah, I know they do that, but it doesn't make sense to me why they do that. If everyone expects to be #1 in the world, everyone but one person is going to be disappointed.
      - GuiA 14y ago
        Go tell that to 18 year olds :)
      - ajdecon 14y ago
        It's not a rational thing, but more instinctive. Your immediate surroundings influence you in all sorts of unconscious ways, but all the people in that global distribution are pretty abstract. You can quote statistics all you like, it's difficult for them to change how you "feel" about yourself. Also http://en.wikipedia.org/wiki/Dunbars_number http://en.wikipedia.org/wiki/Dunbars_number

electronous 14y ago

This article might have a good point, but it's hard to find it amongst all the "my friends and I are really cool and awesome people" speak. Does this article, coupled with the fact that the author submitted it himself, strike anyone else as terribly vain?

GuiA 14y ago
Welcome to HN, where everyone is a rockstar entrepreneur!
prezjordan 14y ago
"His interests include climbing, coding, and being awesome." :( Maybe it's tongue-in-cheek, but still.

tkiley 14y ago

The "MIT syndrome" thing is crucial. I think the most important trait in a startup leader is humility. To build a kick-ass sustainable company, you absolutely, positively must be comfortable working with people who are (in some or most respects) smarter than you. Also, I find it very interesting that the "high" of this roller coaster is the funding.

dkrich 14y ago
I never understand why funding seems to be the end goal either. To me, apart perhaps from some vindication of your idea, the happiness people experience when funded almost shows a lack of vision.
- BenjaminCoe 14y ago
  For people with financial burdens, venture capital can be the difference between being able to pursue your startup dreams, or letting them die on the vine. There are definite downsides to raising money, and I totally understand the stigma the HN community tends to attach to it. Having said that, a 500k seed investment let Jesse and I put down everything, and put 100% of our efforts towards Attachments.me. I have no regrets about this.
  - dkrich 14y ago
    I'm not debating the merits of raising cash. Most companies and businesses have to do it when starting out. The part that I (and I'm assuming the OP) find puzzling is the part about "climbing to the top of the hill overlooking the city and realizing all our childhood dreams had come true" after having raised a round of investment. This seems to me to be saying "we got a million+ investment and we won!" I think for most that's not really the point of starting a business.
mkramlich 14y ago
I'm trying very hard to avoid the "success if getting investment" path because I think it's an anti-pattern, which in turn leads to other anti-patterns. It's much much better to get funded initially out of your own pocket, and then next out of customer's pockets. The earlier you get a real customer who pays you for what you give them, the earlier you validate your business/product, and you indeed have a real business, with effectively an infinite runway.

hkon 14y ago

I think IT is more like confessions on anyone starting out at anything. Tanks for verifying what carnegie said.. 100 years ago ;-)

k33n 14y ago

Thanks for writing this. As a 20-something startup CEO, I frequently want to write about something mundane (or not) but often choose not to for reasons of confidentiality or that I worry some things will cause problems for me later. I don't think I'm a startup god, or an expert at all. Sometimes it would just help to vent or have a discussion about something with strangers who are in similar positions as me. Unlike some of the other commenters here, your post didn't strike me as self-important. Just looked like you felt like sharing and wanted to have a dialog.

larrys 14y ago

"I began getting depressed about the lack of a life I had outside of work. I’d bring this bad mood to work with me, in turn making it a worse place to be. I’ve since made an asserted effort to dedicate time to my social life: going on trips with friends; going on dates; and, most importantly, getting work completely off my mind occasionally." Serious question (and my thoughts) here I'm not trying to be cute. Regarding your "social life". Do you think you will grow out of this? Because what do you think is going to happen if/when you are married and have children and aren't living in SF or some exciting place and have much on your plate? The best way to insure that you can live the life you want and have some fun is to put all the effort in that you can now and try to put off having fun until a bit later on. Now is when you have energy and should be able to work non-stop with very little else. (I didn't surface for air for 7 years working 6 to 7 days a week ..) I point this out also because the world is littered with people who didn't get into a good school because they spent a bit to much time worrying about missing something or having fun and are paying for that later. I'm sure you've met people like this in your high school. It's a little unclear how long you worked before you realized what you wrote. It was certainly less than two years since you wrote this: "I’ve grown a lot as a person in the past two years." That's not a long time to be denied the pleasures of other people and fun (look at people on tours of duty in the war or speaking of my own experience). The fact that you never had a problem until later means you really haven't dealt with the situation you are in now in the past which I think is what you are saying. Things were easy for you until you got around a group of people who were also good. I know first hand about the MIT syndrome since I saw others that suffered from it at the school that I went to which was quite good. I didn't suffer from that for one simple reason. Things were never easy for me it always took hard work and it also took plenty of effort for me to get into the school I went to. So when I got there I didn't fall apart if I got a "B+". I just kept chugging away while the ones who were "so much smarter" who got in with their top grades and SAT's wilted under the pressure of having to do so much work. This was a long time ago compared to when you are in school. So to answer your question, no, things haven't changed that much. You've got plenty of time to have fun. Now is the time to work as hard as you possibly can with minimal breaks in order to achieve your goals. You might not surface for air for a few years but it will probably be well worth it. One last thing. There will be times in life when you might have some crisis either in personal life or business that will require you to work all the time. I had a case where several of my top people left, I was in the middle of a legal case, and a breakup, and I still had to show up to work doing the job of three people and deal with personal issues and family fights. Having to go through that and knowing I could (similar I'm sure to having climbed a certain mountain like you are doing) was a great experience that made me realize that I didn't have to be scared of the unknown and that I could handle it.

wensing 14y ago

When you say that "Bootstrapping a startup is stressful", are you only referring to the time before you raised the $2.5 million? How long was that? EDIT: According to CrunchBase you raised $500K two months after your company was founded, and another $2 million 13 months later. I'm sure you just used the word without thinking much about it, but technically you bootstrapped for all of 8 weeks. :)

ojbyrne 14y ago
Sometimes people work on things before they found a company around it.
mirsadm 14y ago
I hope there is more to this.8 weeks is like an extended holiday. I've been bootstraping for a year now and yes it is difficult but not that difficult.
modarts 14y ago
Why is there this overwhelmingly anti-bootstrapping sentiment present in the startup community? What's so wrong with taking outside funding?
- j_col 14y ago
  If you take outside funding, you're not bootstrapping. According to Wikipedia: "Bootstrapping in business means starting a business without external help or capital." Source: http://en.wikipedia.org/wiki/Bootstrapping#Business http://en.wikipedia.org/wiki/Bootstrapping#Business There is nothing wrong with taking outside funding, but then you don't get to call it bootstrapping any more (as per the widely-accepted definition above of what the term means). This is mixing up terms.
  - modarts 14y ago
    I should have clarified that I was trying to ask a more general question as to why bootstrapping is seen as a superior way of starting a company as opposed to taking on funding.

dennisgorelik 14y ago

I don't see much traction here: http://siteanalytics.compete.com/attachments.me/ http://siteanalytics.compete.com/attachments.me/ It looks like aqui-hire is the best option for attachments.me

jskopek 14y ago
That's a little harsh of you, and totally unwarranted. The site's user-base has absolutely nothing to do with the article or current conversation.
- dennisgorelik 14y ago
  Are you saying that credentials of the author have nothing to do with the article he wrote? I think it brings important context. Besides, the harsh part is lack of traction, not me pointing to it. Don't kill the messenger.
BenjaminCoe 14y ago
Our main products are a Chrome Extension, and an iPhone application. The website itself gets a, granted small, but growing amount of traffic -- but it's mainly just there to direct people towards the clients. I don't think that Alexa or Compete do a perfect job of reflecting our usage numbers, since the website itself is not the main way people interact with us.
- dennisgorelik 14y ago
  1) Compete shows downtrend for attachments.me I understand it could be a mistake due to low numbers, but still does not look promising. 2) What are attachments.me actual usage numbers today and 1 year ago?
  - BenjaminCoe 14y ago
    I won't give you all of our numbers, but If you look at our Chrome Extension page, you can see that we have 35,000 active installations. Much of this growth has happened over the past six months. These numbers simply aren't well reflected in the Compete score. My coworkers and I work hard, and believe in what we're doing. Rome wasn't built in a day, let's hold of on the talent acquisition talk ;)

fellowshipofone 14y ago

Thanks for the post; running a company is not only about making the right decisions, it is also about living with the bad ones. I think this blog post is a good testimony that helps with that.