How to avoid building a company you'll hate

Hey gang,

My partners and I just finished a year-long exploration to determine the next business we would run. We focused hard on how to avoid building a company that we’d hate running.

I want to share it here because in 8 years of bootstrapping I’ve never seen anyone write about how to figure this out. It’s MASSIVELY important, especially for bootstrappers who are in this to live life on their own terms.

The intro is a good summary:

How do you know if the business you’re running will enable you to live the life you want to live? This was a major question we grappled with during our year-long search for our next business venture, a process we imaginatively termed “Project Next Biz”.

You can read the whole post here:

Would love any feedback or experiences you’ve had doing this.



Interesting article. But I find the ‘click to tweet’ links rather patronising. I know how to tweet and I don’t need to be told what bits to tweet.


Hahah Andy you old codger :wink: No ones got the attention span anymore to actually choose a few hundred characters then copy them into… ohhh look pictures of kittens!


Interesting read. I just quit a startup where I was CTO, and I agree with lots of items in your article.

I took a similar path to decide what to do next, and the product I’m building should project me where I want to be in future.

Thanks @Andy. Been reading Successful Software for a long time, so thrilled you find it interesting.

Re: Click to Tweet - experimenting to see if they’re useful at driving shares and ultimately traffic back to our site or not.

@dominicstpierre thanks! would love to know what you’re building if / when you can share and the process you used to decide to build it.

Sorry for going all grumpy old codger. But things like that seem (to me) to show a certain level of contempt for your audience. And that isn’t something I would ever want to do, regardless of what the metrics say.

Or maybe it is just me that feels like that? In which case you can safely disregard my comment.

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@andy I think we might feel a little differently about those links. I don’t think they show contempt for readers though :slight_smile: But what I think really doesn’t matter much - it’s what readers think that matters. So I’ll pay a little more attention to those b/c of your feedback - thanks!

@kareem I’m building Roadmap, I kind of started from where I wanted to be in 3-4 years, also it’s funny you were mentioning previous app that was crawling for data and that’s kind of always something that needs to changed / fixed etc. I did not wanted to do that.

Also, I was wanting the product to fit with my values.

In short I did not wanted to be where I was being CTO of previous startup. Family always was a priority and I kind of let a startup completely take over, so not only I quit, but it made me build Roadmap, I’m talking about this in this blog post.

The “natural” way would be to write a piece of copy so awesome that a reader couldn’t help but share it. When a sentence has to be highlighted and scripted to draw the reader’s attention to it, may be it is not so good to be shared in the first place?

Now, about your post.

It was moderately interesting. What stops me from being fully excited about it is this: suppose you have taken your business to the $10M you define as a success, and then write this post. The post then would have a lot of value because it shows a results-proven way of thinking. But at this point it is just a … mmm… hypothesis. You have a theory that if you plan everything like that, with criteria like that, you may get to your ideal business. But what if not? What if you somehow end up in the same old 60 hrs/wk mode with investors telling you what to do? Is it a thinking process’ fault (and then the whole post has zero value) or you deviated from your own plan?

In short, you should have written this post after. Way after.

(I mean, if you planned to share the knowledge, and not just get a number of shares.)

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@dominicstpierre Very cool. In my experience building a co will always be a slog but like you once I stop having fun too many days in a row, I reevaluate.

@rfctr thx for the perspectives. i don’t think it’s a waste of time at all to think about your ideal outcome and construct a situation that you think will maximize your chances of achieving it. like i wrote above, i’ve never read about anybody going through this kind of process before, so thought it was worth sharing in case others found it valuable.

writing it after the fact might make it more impactful, but startup stories are full of survivorship bias - how true are they, really? we may fall flat on our faces but if we do it won’t be because we didn’t know what we wanted or what we thought was a good path to achieve it.

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Good read. Thanks for sharing it.

@intelligentcoder Thx!

I’ve been seeing these “click to tweet snippet” things showing up more and more. They just signal to me that the piece was written first and foremost as clickbait, and only secondarily as a vehicle to communicate ideas.


@avdi It’s interesting that the CTT links are such a strong negative signal to you that the content of a 3700 word article appears to be clickbait. Good feedback tho, thx.

Kareem, go make some money!

“Is it going to make me money? If not, don’t do it, ignore it” - Samir

Ignore the comments about click to tweet. Go make some money

@dtrejo haha thanks :slight_smile: I don’t know who Samir is. But definitely gonna experiment - nobody falls asleep at night worrying about me except me (and maybe my mom).

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Haha Samir is a bootstrapping god. He’s so busy making money that he doesn’t comment much online. Speaking of which… back to it :slight_smile:

It would be sad world if we only based our decisions on money.

It’s a nice heuristic to help one focus on providing value to one’s clients.
E.g. I am not an accountant, I should not do my own taxes. Will doing accounting help me make more sales?

Thanks for sharing it, that was a great read!