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Ask HN: How do you start a startup in your 30s when you have wife/kids/mortgage?

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Re: Ask HN: How do you start a startup in your 30s when you have wife/kids/mortgage?

#341
post #5

My friend and I started it as a side job, working nights and weekends. We also downsized and cut all our expenses to about $1,000/month (mortgages were smaller back in 2005). We quit our full-time jobs when 1Password revenues were close to $80,000/year.

You mean 1password.com?! That's amazing great work. Huge Canadian success story [1]. You're definitely underselling the achievement here but guess it's funny to look back and were probably super excited about that first 80k. I imagine there is probably a books worth of war stories about this. [1] https://financialpost.com/fp-finance/toronto-based-1password...

Thank you so much! It was certainly a new chapter for us, working directly for our customers and being able to live on the product we made.

Re: Ask HN: How do you start a startup in your 30s when you have wife/kids/mortgage?

#342
post #5

My friend and I started it as a side job, working nights and weekends. We also downsized and cut all our expenses to about $1,000/month (mortgages were smaller back in 2005). We quit our full-time jobs when 1Password revenues were close to $80,000/year.

This is inspiring and what I'd like to do, too. I'm working on downsizing and reducing expenses. I'll have repaid a credit fully next year, that allows me to increase savings etc. Slowly those things come together. Also trying to create small side hustles, bootstrap them, hope that something sticks and try to scale that up till I can quit the corporate job and focus on things I'd love to do. It's probably a longer jo…

This is awesome, great to hear! You are absolutely right at trying different things. Best of luck!

Re: Ask HN: How do you start a startup in your 30s when you have wife/kids/mortgage?

#343
post #5

My friend and I started it as a side job, working nights and weekends. We also downsized and cut all our expenses to about $1,000/month (mortgages were smaller back in 2005). We quit our full-time jobs when 1Password revenues were close to $80,000/year.

Kudos! Long time user here! Love 1password.

Thank you <3

Re: Ask HN: How do you start a startup in your 30s when you have wife/kids/mortgage?

#344
post #6

My very concrete feelings on this is that you probably don't. Asking folks how to do this is a bit like asking billionaires how to get rich. It's a fun story but it's overfitting. The individual narrative that made a billionaire is unlikely to be available for you. If you ask some millionaires they may be more likely to give you some useful advice around sound investment strategies, living within your means, and iden…

If only anyone knew what that one awesome startup was.

Its the market that drives businesses. If I wait too long to even start trying, chances are slim that I ever will try, markets change you know

On the other hand, if I wait, building a business off the network and skills and reputation and market knowledge I've built, has a higher chance of survival.

My philosophy is to be non-dogmatic but probabilistic and opportunistic. If you see an opportunity, try it out, take a loss maybe, and learn and try again.

Like a good gamble, you need to spend most of the time at the table, in the game before betting big, not working in the shop next door waiting to get in.

Re: Ask HN: How do you start a startup in your 30s when you have wife/kids/mortgage?

#345
> Are all startups at my age generally side hustles that become profitable enough to quit my day job?

They’re either side hustles that succeed enough to go full time, or they’re fully VC-funded so that you don’t have worry about paying the bills while you build it (VCs are explicit about that, they want their founders to pay themselves well enough to focus 110% on the startup and not on niggling distractions like bills and chores and whatnot).

There was a data point floating around a while back showing that most successful startups are actually done by people 40+ yrs old. They have connections in their industry and beyond, and deep domain expertise and knowledge of the problem they’re trying to solve, which gives them an edge. They’re just not in the news as much. Don’t recall where I saw it though, maybe here, maybe google.

You could start networking on Angel List (https://www.angellist.com/) and see what feedback you get on your idea. If you can build a very basic prototype that would help too.

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