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.
Confessions of a 20-Something Startup CTO
51–60 of 96 posts
Re: Confessions of a 20-Something Startup CTO
#52The "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.
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.
Re: Confessions of a 20-Something Startup CTO
#53"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. Regardin…
"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." How do you reconcile this with most startups failing? (Let's assume here that people fail for reasons other than just "didn't work hard enough.")
"How do you reconcile this with most startups failing?"
Very simple. Don't choose the type of startup that has a 3 in 10 chance of succeeding on the off chance that you are the lucky one that hit's the lottery. Stop thinking that if you want to be an entrepreneur the only thing you can do is get into YC, Techstars, 500 Startups or have some idea that a VC will invest in.
The other thing you can do is work as hard as I've indicated but put eggs into other baskets. The first business that I did (which I sold after 9 years and did pretty well with) I had spent time learning UNIX while I was running the business in order to manage the business (quite unusual back then but I found it fun and interesting. So it was my fun but the fun had a purpose). With those skills I was able to do something later that also made money. I worked all the time but I dedicated some of my time also to learning new things that could be "the next thing" or a fall back if the first thing failed (it didn't).
The point is, just like in investing you are supposed to diversify you can do that as well with business. Now I didn't diversify my efforts until maybe year 4 (because I started with nothing and had to make up for not having enough capital to do everything that I needed) but once I got to that point I took some time and money and invested even then in the future.
I started my business with maybe $7000 (in today's dollars) that I earned by doing various things in high school and college by working.
Yes, for me it worked out. But my suggestions are also based on many years of observing what others did that didn't work and how much effort they put in.
Re: Confessions of a 20-Something Startup CTO
#54"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. Regardin…
It is possible to have a social and work life balance. As an entrepreneur it will always weigh towards work but doing 6-7 days (80 hours) a week for years shows either that you enjoy it or there is a problem in product or delegation abilities. I think there is something to be said for taking advantage of your youth and energy for something other than work.
"either that you enjoy it or there is a problem in product or delegation abilities."
I agree that some people have a problem "in product or delegation abilities".
Unfortunately business is about risk and constant change. If you don't have enough squirreled away when the rainy day comes you will be dead in the water. The world is littered with business people who didn't think things in their business would ever change. Maybe you own a restaurant and a competitor opens up down the street? Maybe you work in video post production, with network clients, but then their business drops so your business goes out the window. Are you prepared for that (Andy Grove of course said "only the paranoid survive". And that is true from my many years.)
Related, have you ever heard of someone winning a medal or being atop in sports or entertainment and at least in the early years not working 24x7 to achieve their dream?
"shows either that you enjoy it "
It is well know that in order to succeed at something you have to enjoy it to the point of wanting to do it all the time and being a work workaholic. You will always be able to find cases where there are exceptions of course but point is whether you want to be at the top or merely make sure you aren't one day in a van down by the river you better be working pretty hard.
Re: Confessions of a 20-Something Startup CTO
#55"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. Regardin…
What did those 7 years give you that perhaps a more balanced lifestyle wouldn't have?
The ability to lead a much more relaxed lifestyle that has people saying I look 12 years younger than people my age for one thing. I still work very hard (because I enjoy what I do) but I set my own hours and can basically do whatever I want to do.
By the way I was in a non-tech grind it out type business. I didn't "hit the lottery". I built a traditional business and sold it. It is still operating today and the person who purchased it has operated it for longer than I did.
Re: Confessions of a 20-Something Startup CTO
#56I don't see much traction here: http://siteanalytics.compete.com/attachments.me/ It looks like aqui-hire is the best option for attachments.me
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.
Re: Confessions of a 20-Something Startup CTO
#57Earlier quoted context omitted.
What did those 7 years give you that perhaps a more balanced lifestyle wouldn't have?
The ability to lead a much more relaxed lifestyle that has people saying I look 12 years younger than people my age for one thing. I still work very hard (because I enjoy what I do) but I set my own hours and can basically do whatever I want to do. By the way I was in a non-tech grind it out type business. I didn't "hit the lottery". I built a traditional business and sold it. It is still operating today and the pers…
Interesting. In Japan, all around me are people who try to burn the wick at both ends hoping for a light at the end of the tunnel.. And they most definitely do not resemble the description you just gave of yourself..
Re: Confessions of a 20-Something Startup CTO
#58Earlier quoted context omitted.
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, jus…
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.
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).
Re: Confessions of a 20-Something Startup CTO
#59"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. Regardin…
"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." This is insane. While you need to meet your responsibilities and commitments, once you've done that, live the life you want, and live it right now. That might involve work non-stop and very little else, if that's what you really want - but if y…
"This is insane. While you need to meet your responsibilities and commitments, once you've done that, live the life you want, and live it right now."
If I understand what you are saying you are telling people to simply meet your current living obligations and worry about the future in the future.
Good luck with that.
Take a look around at all the people without a pot to piss in that have no savings or can only survive because they have maybe 6 mos. living expenses stashed away. Fine strategy if everything works out. History has shown though for the majority of people (people in corporate jobs that were well paid that lived "hand to mouth" and are now crying the blues) that followed this strategy have no paddle now.
By the way, and importantly, if you think "what I am doing is hot and I will always be able to find a job" let me point something out. Over time there are always "hot" professions where people think they are invincible. The "hotness" attracts more people to the profession and that of course assumes that the profession or what you are good at is in demand X years down the road.
Think programming skills will always be in demand? Maybe and maybe you will always be cutting edge. But you could also end up being a) an out of work lawyer (that was hot at one point it was unthinkable to go to law school and not do well when I was growing up) or b) ask some old timers who knew cobol how much they were in demand (other than y2k a fluke of course!)
Re: Confessions of a 20-Something Startup CTO
#60Earlier quoted context omitted.
I would think the fact that they are one of hundreds out of billions would inflate rather than deflate the ego.
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.
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.