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Bootstrapping a side project into a profitable seven-figure business

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Re: Bootstrapping a side project into a profitable seven-figure business

#212
post #128

Earlier quoted context omitted.

Would you have the same strategy if you were to do it again? Do you have LLMs in mind in your SEO strategy (like really long articles bragging about how good your app are in a non human readable way? Would love to have your thoughts on that!

Thanks for the question. As I noted it took 7 years to actually get any substantial Google traffic – if I was to start again I would potentially change some of what I've written to be more effective or focus on different topics earlier. However my approach is always to write what will be useful and interesting for humans, if Google search also finds it relevant then that's a bonus. I never write just for machines...…

Ok thanks!!

Re: Bootstrapping a side project into a profitable seven-figure business

#214

Not really the point of the post, but it was nice to see a pic of Kyle working with his bird on his shoulder instead of a stock photo or some AI slop generated image.

Thanks! He's a fun little copilot when he's not chewing my cables and mousepad.

Re: Bootstrapping a side project into a profitable seven-figure business

#215
Always encouraging to see that ideas can work out. I'm not quite managing the "let's build a team" aspect just yet but otherwise similar journey and outcome over a (slightly) longer period.

I just wanted to not deal with certificates, now I deal with certificates all day every day lol: https://certifytheweb.com

Re: Bootstrapping a side project into a profitable seven-figure business

#216

Always encouraging to see that ideas can work out. I'm not quite managing the "let's build a team" aspect just yet but otherwise similar journey and outcome over a (slightly) longer period. I just wanted to not deal with certificates, now I deal with certificates all day every day lol: https://certifytheweb.com

Congrats on 100k organizations, that's impressive.

How much of a pain point is support? At that scale, is it becoming a burden without more of a team in place?

I'd be curious to hear more about what the ups and downs on your journey have been like.

Re: Bootstrapping a side project into a profitable seven-figure business

#218

Earlier quoted context omitted.

> live securities prices This is probably impossible in 2025. Many stock exchanges now make more money from selling data feeds than trading fees. It is a little bit crazy. The best that you can hope for is a delayed feed, or last closes.

This is incorrect. Almost all brokers nowadays allow for OAuth connections where you can stream any data you'd see in your broker platform to any consuming web application (given the consuming web application does all the paperwork, dev work, and so on)

    > Almost all brokers
That is a mighty broad brush. I can confidently say that this is untrue for many brokers in continental Europe and North Asia. US brokers? If yes, can you provide some examples?

Re: Bootstrapping a side project into a profitable seven-figure business

#219

Earlier quoted context omitted.

> live securities prices This is probably impossible in 2025. Many stock exchanges now make more money from selling data feeds than trading fees. It is a little bit crazy. The best that you can hope for is a delayed feed, or last closes.

That's the best part about VTSAX and chill: you only ever have last closes. Really though this does not need to be real time at all, just recent enough to save me toil

I much prefer VOO: Vanguard S&P 500 ETF. Tight bid ask spread, good size, and crazy low fees that continue to drop.

Re: Bootstrapping a side project into a profitable seven-figure business

#220
This story is similar to the guys at senja.io: tech founder => marketing/growth person joins => business skyrockets to 1M ARR. It looks to me like a combination of having a product with some revenue and havingthe luck of someone like Jon joining.

I'd be more interested on how to find people like Jon tbh.

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