5 ms·

Why I'm Not Working on my Startup (yet)

51 points by IsaacSchlueter 18y ago

okeumeni 18y ago
Most assumptions you have can only be verified by you. My advice is: try doing something on the side first, something that people can actually use, share it with friend and see how you feel about feedbacks. I found for myself that the greatest motivator is your will to build something useful; your major test will be how you bounce back from negatives. How many hours you put in, when do you work even whether you should leave your job or not will depend of your level of motivation, it’s hard to build a startup without sacrifices.
- IsaacSchlueter 18y ago
  My advice is: try doing something on the side first, something that people can actually use, share it with friend and see how you feel about feedbacks. Well, what I've found is that most of my side projects don't get very far, because I invariably end up pulling a bunch of long nights at my main paying gig, and that saps the motivation considerably. Also, maybe I need ruder friends, but I've found much better results sharing stuff with strangers. They're more honest. Friends are biased by their desire to make you feel good.
  - bigbang 18y ago
    Post it HN. I dont think HN readers are biased(even if some of them are your friends) :)
    - IsaacSchlueter 18y ago
      I'm not so sure. The posters may not be biased, but that doesn't mean that the comments aren't. I've seen some ideas that were just not all that great get lavished with praise. It's possible that I just missed what was so useful about the site in question... but it's also possible that those who didn't like the site didn't comment. I didn't like the site, or indeed care about it at all, and I'm not the type to want to hurt someone's feelings, so I didn't comment on it. Friends or not, I think the best feedback is likely from users who have the problem you're trying to solve. The best question is probably "why wouldn't you use this thing?"
      - iron_ball 18y ago
        More often, I see feedback (from all sources) focus on implementation, when the real response should be "your basic idea is dumb."
      - terpua 18y ago
        Why not build and solve a problem you have?
        IsaacSchlueter 18y ago
        Actually, I have two side projects that are exactly that. But I keep ignoring them. That's the problem :) My user is getting upset with me, and about to look to my competitors.
        terpua 18y ago
        Perhaps the problem isn't painful enough?
        cypress-hill 18y ago
        Why not build and solve a problem you have? because he's following the herd
        IsaacSchlueter 18y ago
        Hi, troll.
  - swombat 18y ago
    Swap your day around. It sounds crazy, but from the sound of it, you're crazy already, so that shouldn't be a change. What I mean is: * Wake up at 3am * Work until 1 hour before it's time to go to the office * Have a 1-hour nap * Go to work, and work until you can't work anymore * Go home, sleep You'll have no social life for about 6 months, but you'll spend the best hours of each day working on your baby. After 6 months, you'll probably have something worth launching and/or quitting for. This is not for the sane, but it's doable. I did it, and I don't regret it.
  - ajju 18y ago
    You don't need ruder friends, you need a partner or two who are equally enthusiastic, nay who are BANKING on that project succeeding. Hopefully they are banking on it because they are really passionate about the idea and really want to get out of the boring day job. Like you, I spent almost 3 years trying to start one project after another that fizzled out. For some I even had a partner. Unfortunately it was always a "side project" for one or both of us. Till I reached a point of desperation and frustration with not doing my own thing, and till I found partners passionate about the project just because, I found it pretty hard to get up at 5 to code too. Now I know I'll let not just myself but also them down if I show up without getting my stuff done. Seriously, the formula to finally starting a startup is simple a) Get desperate (passionate) b) Find similarly desperate (passionate) folks.
bookhuddle 18y ago
I encourage you to work on one or more of your ideas sooner rather than later, even while working full-time. You seem to be at the stage in your life where you could pursue the YCombinator program (or similar programs). This is one way to fund your ideas without going the self-funded route. You seem to have the skills that you'll always be able to get jobs at Yahoo or elsewhere. You don't really have much to lose.
- IsaacSchlueter 18y ago
  You don't really have much to lose. Thanks. But that non-trivial pile of RSUs is really very non-trivial :)
  - bigbang 18y ago
    Every year you will be getting RSUs or retention bonuses. At some point you should make the call rite. Im in same position as you.
    - IsaacSchlueter 18y ago
      True that. You do have to call it quits at some point. But why not wait until it's enough to actually coast on for a while?
      - cypress-hill 18y ago
        Hi, troll
- ajross 18y ago
  Actually, my reading was he (like me) was well past the stage of life where YC funding would be helpful. Someone correct me if I'm wrong, but a first round YC bet is something like "cost of living for two college students for a summer". To an established professional with a stable job, this is noise: most of us could fund such a company for three months right out of our bank accounts. The benefit to doing the YC thing is the exposure to sources for later funding rounds, and the networking that comes with being part of the community. The money isn't the draw for anyone but a brand new graduate. It's just there to make sure no one starves while working on the project.
rickd 18y ago
This is exactly what I planned when I left school. Cool! My plan was to work for 5 years at a job I at least LIKED- put away enough to live for 1-2 years without doing anything at all- and then work on whatever startup idea I figured would be best at the time. Why did I choose 5 years? Honestly, it was because most companies vest employees in their retirement plan of choice after 5 years. Fast forward to 5 years later (last June 15th) and I'm ready! Money saved, credit card balances at 0, no debt, no obligations! I've even started to work on some of the code for my idea. The only thing I didn't count on was the housing market... so now I just have to hang around my current job until my place sells. anybody want to buy a condo in Chicago? Seriously though- from where I'm sitting, it's a great plan. Give yourself the opportunity and ability to do something amazing, and chances are you will! Not to mention, if you are at least managing your money successfully, and not going in to debt- you're doing vastly better than many Americans already. Good Luck!! :cross posted from comments:
prakash 18y ago
There's more than one way to do it, and this is a more deliberate path. good plan, seriously. I quit my job early this year, have enough savings to last for a while (it's easy when you live like a grad student), and am exploring ideas.
alex_c 18y ago
I feel that I've learned an incredible amount since I left my job and started my start-up - and I think that's largely an indication of how little I actually knew when I jumped in. If I can offer anything for consideration, it's this: When do you want to make your mistakes? Now, or in a few years? While working for a large company, or while living off your savings? While doing stuff "on the side", or while doing it "for real"? I am not advocating one choice over the other, but this might be another useful angle to approach the problem.
- IsaacSchlueter 18y ago
  Thanks, that's actually helpful. Personally, I don't see "living off my savings" as a bad time to make mistakes. Webdevs are usually in short supply, and we're past the first speculative bubble, so "get a job" will likely always be an option. I can "retire" every 5 years :)
  - deleted 18y ago
    [deleted]
- ajju 18y ago
  This is a very good point. Also, the mistakes you make at a big company tend to be very specialized to the product you are working on. When you start up on your own the range of mistakes you can make blows up by an order of magnitude. You start learning a lot, fast, but this also means you have to be able to take failure in your stride. A startup will fish out and highlight every single hole in your knowledge, skills and personality. You better have the optimism, the enthusiasm and the friends (partners) who'll help you deal with that. I think this might be one of the major reasons single person startups often fail.
wheels 18y ago
Having a bit of a runway is good, and real-world job experience can pay dividends. Some suggest that you'd get the same out of a failed startup, but both routes have their advantages. One thing I learned, sadly later than I wish I had -- before starting a startup practice living cheap. Start really considering if you really need that iPhone or that new monitor, buy nothing but generic stuff, have one beer at the bar instead of three, get a house-mate. Cook! As I was building towards going full-time on the startup I managed to get my cost of living down to less than half of what it was, with no major lifestyle changes. That'll give you a nice pad and the skills to stretch it when you do go full-time. You can also spend the time learning; nothing teaches like experience, but you can spend time building up your contacts, researching your field, learning as much as possible about startups, setting up infrastructure, searching out good co-founders -- so that when you're ready to run you can go at it full speed.
- babul 18y ago
  Living cheap also has benefit in that it often forces you to assess what you need and want in life and ultimately what is really important to you. There is a certain pleasure to be had to free oneself of the materialistic lifestyle we are often indoctrinated into following through nurture, especially in many western countries/cultures (e.g. process of society and education often teaches get a job, buy a house, get a car, get better job, bigger house, newer car etc. much of which is not really necessary). When you earn enough not to worry about food and bills, you can really begin to do the things you want and learning to live cheap certainly helps. The freedom is liberating and truly the best things in life are free (or often surprisingly cheap).
IsaacSchlueter 18y ago
I've been absolutely floored by the quality and quantity of comments and advice from all of you, here and on my blog. I've reworked my plans and expectations a tad, and gained a lot more confidence about some parts that I was shaky on. Thanks, HN!
staunch 18y ago
This is the hacker demographic I will be targeting should I become wealthy enough to finance my own YC-inspired investment firm.
blakeweb 18y ago
It's clear from your post and comments that you're a very smart guy. I can tell you think so too, but I'd bet you're even smarter (relatively) than you realize. I agree that if you follow your plan, you're likely to be successful, if you don't give up just a bit too soon and go back to the solid, dependable paychecks. My only two cents concerns your patience. I'll admit, my only experience working for someone else was a year-long internship right after college, but despite it being a sweet gig in a beautiful place, I hated it, and it was all I could do to make it to the end of the year. Since then, it's been only startups for me, and it's so incomparably different and better that I just have to weigh in that your 3 year plan is a little too patient and risk-averse for me. It sounds like you love your job already. That's definitely key. But if you wait another 3 years to go for it, and find out you're fantastic at it and are having the time of your life, won't it seem like you should have given it a go even sooner? For instance, by getting a cofounder willing to pay the company bills for a while as an even trade for your fantastic ideas? Seems worth considering if you'd both rather start sooner than later. Making your own stuff full time is so fun.
cypress-hill 18y ago
so sad. his whole life has boiled down to fetishisizing work how about this for a plan - get married and have kids. you'll have a regular sex partner, and when you are sixty, you won't sit around wondering why you are alone and if you save some money, take a winter off and be a ski bum. one year cruising between whistler, aspen, half the crazy ass monster resorts in the alps...beats the hell out of pissing into the wind in the website game
- IsaacSchlueter 18y ago
  Hi, troll.
  - cypress-hill 18y ago
    keep swinging. sorry not everyone is in the mutual support echo chamber.
ajju 18y ago
Bootstrap your startup to beta while still at Yahoo. Sure you'll have to put up with not working on what you love 100% of the time but it'll be better than 0% and probably close to 100% seeing how you seem to like Yahoo o.k. I am in a situation very similar to yours - good employer, o.k. hours and an overdue startup. I am doing this right now. It's long days and busy weekends and try as I may, a couple of days a week I don't get any sleep. But there is both satisfaction and a reduction in risk in doing this for me. For me, it's not the financial risk that matters as much but I just wasn't sure I would be able to maintain my focus and enthusiasm doing just a startup - amongst other reasons because my cofounders are non-technical. On the other hand the fact that my cofounders have funded the startup, pay me to do this (on top of my salary at bigco) and handle all the boring non-technical tasks while still letting me be an equal part of strategy and fundraising - all these make my situation a bit different from yours.

Most assumptions you have can only be verified by you. My advice is: try doing something on the side first, something that people can actually use, share it with friend and see how you feel about feedbacks. I found for myself that the greatest motivator is your will to build something useful; your major test will be how you bounce back from negatives. How many hours you put in, when do you work even whether you should leave your job or not will depend of your level of motivation, it’s hard to build a startup without sacrifices.

IsaacSchlueter 18y ago
My advice is: try doing something on the side first, something that people can actually use, share it with friend and see how you feel about feedbacks. Well, what I've found is that most of my side projects don't get very far, because I invariably end up pulling a bunch of long nights at my main paying gig, and that saps the motivation considerably. Also, maybe I need ruder friends, but I've found much better results sharing stuff with strangers. They're more honest. Friends are biased by their desire to make you feel good.
- bigbang 18y ago
  Post it HN. I dont think HN readers are biased(even if some of them are your friends) :)
  - IsaacSchlueter 18y ago
    I'm not so sure. The posters may not be biased, but that doesn't mean that the comments aren't. I've seen some ideas that were just not all that great get lavished with praise. It's possible that I just missed what was so useful about the site in question... but it's also possible that those who didn't like the site didn't comment. I didn't like the site, or indeed care about it at all, and I'm not the type to want to hurt someone's feelings, so I didn't comment on it. Friends or not, I think the best feedback is likely from users who have the problem you're trying to solve. The best question is probably "why wouldn't you use this thing?"
    - iron_ball 18y ago
      More often, I see feedback (from all sources) focus on implementation, when the real response should be "your basic idea is dumb."
    - terpua 18y ago
      Why not build and solve a problem you have?
      - IsaacSchlueter 18y ago
        Actually, I have two side projects that are exactly that. But I keep ignoring them. That's the problem :) My user is getting upset with me, and about to look to my competitors.
        terpua 18y ago
        Perhaps the problem isn't painful enough?
      - cypress-hill 18y ago
        Why not build and solve a problem you have? because he's following the herd
        IsaacSchlueter 18y ago
        Hi, troll.
- swombat 18y ago
  Swap your day around. It sounds crazy, but from the sound of it, you're crazy already, so that shouldn't be a change. What I mean is: * Wake up at 3am * Work until 1 hour before it's time to go to the office * Have a 1-hour nap * Go to work, and work until you can't work anymore * Go home, sleep You'll have no social life for about 6 months, but you'll spend the best hours of each day working on your baby. After 6 months, you'll probably have something worth launching and/or quitting for. This is not for the sane, but it's doable. I did it, and I don't regret it.
- ajju 18y ago
  You don't need ruder friends, you need a partner or two who are equally enthusiastic, nay who are BANKING on that project succeeding. Hopefully they are banking on it because they are really passionate about the idea and really want to get out of the boring day job. Like you, I spent almost 3 years trying to start one project after another that fizzled out. For some I even had a partner. Unfortunately it was always a "side project" for one or both of us. Till I reached a point of desperation and frustration with not doing my own thing, and till I found partners passionate about the project just because, I found it pretty hard to get up at 5 to code too. Now I know I'll let not just myself but also them down if I show up without getting my stuff done. Seriously, the formula to finally starting a startup is simple a) Get desperate (passionate) b) Find similarly desperate (passionate) folks.

bookhuddle 18y ago

I encourage you to work on one or more of your ideas sooner rather than later, even while working full-time. You seem to be at the stage in your life where you could pursue the YCombinator program (or similar programs). This is one way to fund your ideas without going the self-funded route. You seem to have the skills that you'll always be able to get jobs at Yahoo or elsewhere. You don't really have much to lose.

IsaacSchlueter 18y ago
You don't really have much to lose. Thanks. But that non-trivial pile of RSUs is really very non-trivial :)
- bigbang 18y ago
  Every year you will be getting RSUs or retention bonuses. At some point you should make the call rite. Im in same position as you.
  - IsaacSchlueter 18y ago
    True that. You do have to call it quits at some point. But why not wait until it's enough to actually coast on for a while?
    - cypress-hill 18y ago
      Hi, troll
ajross 18y ago
Actually, my reading was he (like me) was well past the stage of life where YC funding would be helpful. Someone correct me if I'm wrong, but a first round YC bet is something like "cost of living for two college students for a summer". To an established professional with a stable job, this is noise: most of us could fund such a company for three months right out of our bank accounts. The benefit to doing the YC thing is the exposure to sources for later funding rounds, and the networking that comes with being part of the community. The money isn't the draw for anyone but a brand new graduate. It's just there to make sure no one starves while working on the project.

rickd 18y ago

This is exactly what I planned when I left school. Cool! My plan was to work for 5 years at a job I at least LIKED- put away enough to live for 1-2 years without doing anything at all- and then work on whatever startup idea I figured would be best at the time. Why did I choose 5 years? Honestly, it was because most companies vest employees in their retirement plan of choice after 5 years. Fast forward to 5 years later (last June 15th) and I'm ready! Money saved, credit card balances at 0, no debt, no obligations! I've even started to work on some of the code for my idea. The only thing I didn't count on was the housing market... so now I just have to hang around my current job until my place sells. anybody want to buy a condo in Chicago? Seriously though- from where I'm sitting, it's a great plan. Give yourself the opportunity and ability to do something amazing, and chances are you will! Not to mention, if you are at least managing your money successfully, and not going in to debt- you're doing vastly better than many Americans already. Good Luck!! :cross posted from comments:

prakash 18y ago

There's more than one way to do it, and this is a more deliberate path. good plan, seriously. I quit my job early this year, have enough savings to last for a while (it's easy when you live like a grad student), and am exploring ideas.

alex_c 18y ago

I feel that I've learned an incredible amount since I left my job and started my start-up - and I think that's largely an indication of how little I actually knew when I jumped in. If I can offer anything for consideration, it's this: When do you want to make your mistakes? Now, or in a few years? While working for a large company, or while living off your savings? While doing stuff "on the side", or while doing it "for real"? I am not advocating one choice over the other, but this might be another useful angle to approach the problem.

IsaacSchlueter 18y ago
Thanks, that's actually helpful. Personally, I don't see "living off my savings" as a bad time to make mistakes. Webdevs are usually in short supply, and we're past the first speculative bubble, so "get a job" will likely always be an option. I can "retire" every 5 years :)
- deleted 18y ago
  [deleted]
ajju 18y ago
This is a very good point. Also, the mistakes you make at a big company tend to be very specialized to the product you are working on. When you start up on your own the range of mistakes you can make blows up by an order of magnitude. You start learning a lot, fast, but this also means you have to be able to take failure in your stride. A startup will fish out and highlight every single hole in your knowledge, skills and personality. You better have the optimism, the enthusiasm and the friends (partners) who'll help you deal with that. I think this might be one of the major reasons single person startups often fail.

wheels 18y ago

Having a bit of a runway is good, and real-world job experience can pay dividends. Some suggest that you'd get the same out of a failed startup, but both routes have their advantages. One thing I learned, sadly later than I wish I had -- before starting a startup practice living cheap. Start really considering if you really need that iPhone or that new monitor, buy nothing but generic stuff, have one beer at the bar instead of three, get a house-mate. Cook! As I was building towards going full-time on the startup I managed to get my cost of living down to less than half of what it was, with no major lifestyle changes. That'll give you a nice pad and the skills to stretch it when you do go full-time. You can also spend the time learning; nothing teaches like experience, but you can spend time building up your contacts, researching your field, learning as much as possible about startups, setting up infrastructure, searching out good co-founders -- so that when you're ready to run you can go at it full speed.

babul 18y ago
Living cheap also has benefit in that it often forces you to assess what you need and want in life and ultimately what is really important to you. There is a certain pleasure to be had to free oneself of the materialistic lifestyle we are often indoctrinated into following through nurture, especially in many western countries/cultures (e.g. process of society and education often teaches get a job, buy a house, get a car, get better job, bigger house, newer car etc. much of which is not really necessary). When you earn enough not to worry about food and bills, you can really begin to do the things you want and learning to live cheap certainly helps. The freedom is liberating and truly the best things in life are free (or often surprisingly cheap).

IsaacSchlueter 18y ago

I've been absolutely floored by the quality and quantity of comments and advice from all of you, here and on my blog. I've reworked my plans and expectations a tad, and gained a lot more confidence about some parts that I was shaky on. Thanks, HN!

staunch 18y ago

This is the hacker demographic I will be targeting should I become wealthy enough to finance my own YC-inspired investment firm.

blakeweb 18y ago

It's clear from your post and comments that you're a very smart guy. I can tell you think so too, but I'd bet you're even smarter (relatively) than you realize. I agree that if you follow your plan, you're likely to be successful, if you don't give up just a bit too soon and go back to the solid, dependable paychecks. My only two cents concerns your patience. I'll admit, my only experience working for someone else was a year-long internship right after college, but despite it being a sweet gig in a beautiful place, I hated it, and it was all I could do to make it to the end of the year. Since then, it's been only startups for me, and it's so incomparably different and better that I just have to weigh in that your 3 year plan is a little too patient and risk-averse for me. It sounds like you love your job already. That's definitely key. But if you wait another 3 years to go for it, and find out you're fantastic at it and are having the time of your life, won't it seem like you should have given it a go even sooner? For instance, by getting a cofounder willing to pay the company bills for a while as an even trade for your fantastic ideas? Seems worth considering if you'd both rather start sooner than later. Making your own stuff full time is so fun.

cypress-hill 18y ago

so sad. his whole life has boiled down to fetishisizing work how about this for a plan - get married and have kids. you'll have a regular sex partner, and when you are sixty, you won't sit around wondering why you are alone and if you save some money, take a winter off and be a ski bum. one year cruising between whistler, aspen, half the crazy ass monster resorts in the alps...beats the hell out of pissing into the wind in the website game

IsaacSchlueter 18y ago
Hi, troll.
- cypress-hill 18y ago
  keep swinging. sorry not everyone is in the mutual support echo chamber.

ajju 18y ago

Bootstrap your startup to beta while still at Yahoo. Sure you'll have to put up with not working on what you love 100% of the time but it'll be better than 0% and probably close to 100% seeing how you seem to like Yahoo o.k. I am in a situation very similar to yours - good employer, o.k. hours and an overdue startup. I am doing this right now. It's long days and busy weekends and try as I may, a couple of days a week I don't get any sleep. But there is both satisfaction and a reduction in risk in doing this for me. For me, it's not the financial risk that matters as much but I just wasn't sure I would be able to maintain my focus and enthusiasm doing just a startup - amongst other reasons because my cofounders are non-technical. On the other hand the fact that my cofounders have funded the startup, pay me to do this (on top of my salary at bigco) and handle all the boring non-technical tasks while still letting me be an equal part of strategy and fundraising - all these make my situation a bit different from yours.