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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?

#101

Post by jchonphoenix »

goatherders wrote: post #52

If you want to maintain your current standard of living and start a business you need customers, investors, or savings. If you want to start any business, startup or lawncare and all points in between, you need customers, investors or savings. So start by solving that problem. P.S. the "90% of startups fail" is inaccurate and moronic. It gives no context on the type of business or the outcome. Starting a 1 million do…

Any pointers on how it's simple to start a lifestyle company? I've always been venture backed so breaking into a market for a lifestyle business seems just as hard to me

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

#102

Post by LanceH »

foobarian wrote: post #84
pc86 wrote: post #50

Earlier quoted context omitted.

If you're not a FAANG engineer, and like 95% of people work somewhere that doesn't give you a ton of stock or RSUs, and you don't live in a super expensive metro, $100-150k is basically strong mid/weak senior money. I know plenty of places hiring with no stock, no bonuses, and seniors top out at $160k or so. They hire capable engineers no problem. With that in mind, taking a pay cut into the middle of that range to d…

I think the problem is not the paycut, so much as you suddenly work 80 hour weeks and never see your kids.

> work 80 hour weeks

Hasn't really been my experience. There can be the odd extra evenings or even weekends, but nothing drastic.

The big difference in hours is probably how effective those 40 hours a week need to be compared to a big company.

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

#103

Post by WestCoastJustin »

roustem wrote: 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...

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

#104

Post by cynusx »

You know everything is possible but a situation like this makes it a lot harder.

First off, young kids (Second, founders that have investment do get a salary so it's not impossible. However, the fundraising climate just collapsed and it is harder to fundraise today.

Third, it's not really necessary to build technology to fundraise though.. what's more important is to convince the investor that there is a genuine need for what you are building and that you have a team that can get it in the customers hands.

The best way to do that is with data from potential user interviews backed up by clickable prototypes of the product.

You don't actually have to quit your job to work with designers and conduct user research to figure out what you're thinking of building makes sense and it's trivially cheap to hire user testers online.

Talking to potential users and building out the prototypes is not a fulltime job. From there the insights alone should be enough to convince your wife, angels or accelerators to take a risk on you to build it. VC's will only come when you have graphs going up into the right.

So yes, keep it a side hustle but don't program anything... iterate on prototypes instead.

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

#105

Post by bombcar »

foobarian wrote: post #84
pc86 wrote: post #50

Earlier quoted context omitted.

If you're not a FAANG engineer, and like 95% of people work somewhere that doesn't give you a ton of stock or RSUs, and you don't live in a super expensive metro, $100-150k is basically strong mid/weak senior money. I know plenty of places hiring with no stock, no bonuses, and seniors top out at $160k or so. They hire capable engineers no problem. With that in mind, taking a pay cut into the middle of that range to d…

I think the problem is not the paycut, so much as you suddenly work 80 hour weeks and never see your kids.

If it's your startup, choose a location to work that's close to home, and have the kids come over.

I fondly remember running around the overly large halls of various companies my dad worked for which were startup or startup adjacent.

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

#106

Post by earino »

Xcelerate wrote: post #92
earino wrote: 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…

> You signed up for a bunch of responsibilities. You are always going to be your kids parent. You are only going to have this one opportunity to get this marriage and this family right. I think this is a bit of a depressing take. Even committed parents and spouses take alone time for themselves and have hobbies. Just treat your side project as your hobby and you can still have a healthy family. Also, think about how…

I actually agree with a lot here. If the question had been "how can I have a fulfilling hobby while also working full time", i think I'd agree with a lot of the advice you gave. It's very good advice about time boxing, having realistic goals, and looking for a well rounded life. Having hobbies is something that can be really rewarding, and hobbies can be many kinds of things, from deeply technical to purely relational and social.

However, I will admit my bias here, the OP explicitly talked about "a startup", and I don't believe I know of too many hobbies that allowed someone to replace their income and retain their standard of living. The people I know who have done this have, regularly, done so with significant risk, commitment, and single-mindedness of purpose. I'm sure there are exceptions as those you listed, but I personally haven't experienced them.

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

#107

Post by codazoda »

earino wrote: 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…

I also took this path and have yet to really succeed. I am now 45 and an empty nester. I wrote about some of my failed businesses in this blog post titled, "How to Lose Money with 25-Years of Failed Businesses".

https://joeldare.com/how-to-lose-money-with-25-years-of-fail...

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

#108

Post by auspex »

higeorge13 wrote: post #82
tracker1 wrote: post #72

Earlier quoted context omitted.

Depends on the employer and where you live... you may have to get permission or specific exclusion when you start a job. As long as there isn't overlap with the business in question, I haven't experienced an issue working on the side. Note: working on the side is not drawing multiple FTE salaries... but actual work outside business hours.

I don’t know, the conflict of interest especially in saas is tricky. Let’s assume that I build some niche etl tool, my employer deals with data etl for a certain market, how can i safely determine that my side project doesn’t interfere with their business? Not even lawyers can determine this. And what about the working hours overlap? Who knows except my commits to my repo and myself? I don’t know, side projects seem…

You claim it as IP that is previously developed when you start the new job or you submit it to your current employer and get an IP exclusion.

I’ve done both with no issues.

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

#110

Post by bombcar »

atzero wrote: post #67
poulsbohemian wrote: post #37

As someone who tried and ended up broke and divorced... You have to really know the business you are trying to break into and make your goals really attainable. Think in terms of figuring out how to generate even enough to pay your phone bill each month, then move up to a car payment, then to a mortgage. Build in micro-steps, making sure that you have stability at each level before you move up. Can you do parts of th…

I agree with all of this. Fortunately my spouse is very supportive, she just doesnt want to become destitute, and I cant blame her. Also fortunately, we are both boring homebodys and she wouldnt really have a problem with me working on this every night.

I think that's the key - you do it via bootstrapping, and you DON'T kid yourself that you're building the next Apple Computer in your garage. As long as you keep your goals reasonable, it's hard to tell yourself that stupid sacrifices are worth it. (Most people would spend a year in Antartica with no phone for $AppleFounder, but would likely not do it for $moderate income, for an exaggerated example).

But be constantly aware that your main "customer" in your life is your spouse, and then kids. People put up with a lot without making it clear, often.

Someone as an outside observer who can tell you that you're starting to screw things up and you will listen can be incredibly valuable, both for the startup and for the family.

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