Working Alongside of Your Bootstrap

Discussions
#21

I support myself and family via consulting while I build my SaaS “on the side” but during work hours. My wife and kids expect me to be available outside of work time, so I cram almost everything into the regular 8-5 hours. I also spend a little time working on the SaaS in the late evening, but I find that this time for me tends to be pretty unfocused.

I’m not earning nearly as much as I was when I had a regular job, and I know I could go back out and get another “good” job like all the ones I had before, but I just hate jobs so much that I refuse to ever get another one.

If anyone is considering going freelance as an alternative to working for the man, I would highly recommend it. I have the flexibility to do sales and customer support as much as I decide I want to. The days fly by and I no longer have that anxious, cooped-up feeling I did at my jobs. It’s definitely a little harder than having a job but it’s also way better.

#22

I envy people like @patio11 or Peldi from Balsamiq who have been able to start a bootstrapped company while working at a day job. I think I just don’t have the needed discipline.

@fredguth This kind of reminds me of times when I’m hungry but I’m too lazy to make anything to eat. Eventually I get hungry enough that it overpowers my laziness. Likewise, there was a time in my life when I didn’t like having a job but the fun of evenings and weekends were enough to keep my motivation for starting a business below serious levels. It was only after many years of drudgery that I got fed up enough to actually start taking some serious action. The time-squeeze of adding a wife and kids to my life also helped crank up my motivation to escape employment.

So I’m not trying to call you lazy, I’m just saying you might not have the forces in your life yet that motivate you to devote time to bootstrapping a business. I suspect that as time goes on you’ll get “hungrier” and eventually want to “cook” something, just as the course ran for me. I just wish I would have started cooking something before I got as hungry as I am now.

Also, beware of self-fulfilling prophesies like “I don’t think I have the needed discipline.” If that’s what you believe, that’s probably what will be your reality.

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#23

I [quote=“jasonswett, post:22, topic:146”]
So I’m not trying to call you lazy, I’m just saying you might not have the forces in your life yet that motivate you to devote time to bootstrapping a business.
[/quote]

Maybe I didn’t made myself clear. I did bootstrap, more than once, online and offline businesses. So, I really don’t care if you think I am lazy or don’t have the forces as you say. I know I am not and I have.

I was just trying to say that this is a personal matter, there is no right way of doing. You have to know yourself. I know myself enough to know that I couldn’t put my heart in my work if I were doing 2 things at the same time. I would certainly neglect my day job, because I don’t have the discipline they have.

I always choose the fire the boats approach because I am ok with this kind of risk.

#24

I went part time at my old job for a while. Then I quit and lived off savings until I started to get some sales. It helped that:

  • I had enough savings to last at least a year.
  • My partner was supportive.
  • I had no children at the time.

My latest product ( http://www.keywordfunnel.com ) has effectively been developed part time over 6 months, as it takes a fair amount of time to keep my other product (PerfectTablePlan) ticking along.

#25

Very true.

Nothing like working your ass of, and then being humiliated because you didn’t play the political game and hence didn’t get any credit.

That’s when you start to feel that maybe working in your personal time, at 11 in the night sucks, but it sucks less than having to hit your head against the corporate wall every day.

I’ve heard of other people who were in this situation, and the thinking is always the same. “Why did I waste X years playing games/watching stupid TV, when I could have been building my startup?” But the good thing is, any time is as good as any other to start, and once you get into the habit, it gets easy.

I actually prefer it this way. It’s building discipline and focus. Since I only have at most 2-3 hours each night, I have to learn to make the most of them.

#26

I think it was at MicroConf, but I asked Rob Walling about his transition, and he said he didn’t jump until he had solid money coming in from his own businesses.

This seems like a sensible, albeit difficult approach when you have kids. To me that’s perhaps the biggest dividing line - having people depending on you really changes things. One of my regrets is having not really found my way into the idea of doing my own small product earlier in life. On the other hand, it’s something I’m proud of because it’s really required getting outside of my “comfort zone” as a programmer.

#27

@fredguth I totally misread you there, sorry.

Unrelated to that: another thought I want to add is that it’s easy to underestimate how long it will take you to get to ramen profitable. I thought it would take me a few months, but I’m still working on getting there after 3 years of work, albeit very part-time work.

#28

I’m a developer in a market with major demand for my skills on the cusp of my life having much more financial demands due to house/kids/other dependents. The window for me to take risks and play games is closing fast so I’m trying to get as close to the edge as possible. I’m also getting older and hustling just isn’t as easy as it used to be :wink:

I save money at a regular 9-5, quit and work on my idea for as long as I can float with a little freelancing here and there. When I run out of money I find a job or a short contract position, save some more, and quit again.

Right now I’m in the 2nd year so I’ve saved, quit, bootstrapped, got a job, quit, bootstrapped and now I’m with a 9-5 job again.

The 1st and 2nd time I’ve worked full time on my startup I made major mistakes that set me back but now I have some momentum and success building up. The snowball is rolling and I like the current progress of things.

My only concern is I’m slowly destroying my ability to find a job by quitting so often and making the google results for my name all about my startup. My big word of caution is you need to be in a really strong developer market to make this work. I’m almost at the point where I am undesirable as a full time employee so we’ll see if I can push past that.

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#29

For years, my lifestyle was as follows:

I worked as a consultant for 8 months each year, and travelled for 4 months. As I was used to making a shorter working year fund me for the entire year, it was quite easy to transition from that to part-time consulting/part-time bootstrapping until the money was good, then full-time bootstrapping.

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