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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?

#61

VC here. If you're building a bootstrapped business, then starting as a side project and building up revenue until you can go full time is probably the way to go. If you're going the venture-backed route, I think there's a misconception that there's no salary or minimal salary at early stages when you're funded, but this is not true. Most founders take a reasonable salary, where reasonably is defined more by your per…

I think I understand what you mean. Bootstrap = use your current salary. VC = use startup funds to pay yourself but it gets touchy real quick.

I currently make 140k in MCOL, so to hear that taking a 140k salary isnt out of the question, eventually, is reassuring.

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

#62
> Are all startups at my age generally side hustles that become profitable enough to quit my day job?

Kinda, successes will generally be:

1) Ascended side-hustle (soooooo much luck involved on this one),

2) You basically already have minimal FIRE money or better (for whatever reason—saved well while earning high, family is rich, whatever) and can afford to take a couple years without an employer with negligible risk to your financial stability, or

3) You have a high-earning spouse to cover the bills while you give your dream a try

1 is easily the hardest and least-likely to succeed—so much less time to put into it, and you're having to steal free and family time to do it rather than working during... work hours.

(see also: getting started with a career in the arts, especially 2 and 3)

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

#63
Hi there! I'm someone currently doing this. I'm CTO at a small startup in Oakland, am married, have a 4-month-old, have a mortgage. CEO just turned 40, also has a mortgage, is married, and has two kids.

Like everything, there's tradeoffs in time and money. Will you move faster if you're spending all of your time hustling on the startup? Maybe! Not every business and not every startup requires 24/7 hustle. Does this force ruthless prioritization? Yes. That's a good thing!

It also means my cofounder and I are very cautious in hiring, using offshore contractors anywhere we can, because we know that the pool we're dipping into is legitimately our own salaries. This is also a good thing! Paying yourself enough to live on without stress and keeping all other expenses low and tight is still "running lean" in my book.

Ok, so how: We got lucky of course, but some of that luck can be replicated. My CEO already knew some VCs from previous networking; those VCs gave us some pre-seed working capital, which allowed us to build enough to get more VCs on board, which gave us a year+ of runway to keep building. We did a _lot_ of pre-vetting with our target market before building, and the nice thing about pre-vetting is you can do it while you still have a job working for someone else.

The thing to remember as a founder is that part of why tech companies provide great salaries and so many perks is so their employees can be at work and fully focus on the work. You should treat yourself like a valued employee as a founder, and create the conditions for you to do your best work, which probably means not stressing about paying the mortgage.

The hustle and drive should come from your passion for the business and the approaching zero cash day, not forcing your family to live on ramen.

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

#64
Way back in the year 2000, when you and I were kids, Joel Spolsky had just finished managing the addition of VBA into Excel 5.0 and was quitting Microsoft to start his own companies like StackOverflow, FogBugz, and Trello, and wrote this illuminating blog post:

https://www.joelonsoftware.com/2000/05/12/strategy-letter-i-...

> Building a company? You’ve got one very important decision to make, because it affects everything else you do ... Whether to grow slowly, organically, and profitably, or whether to have a big bang with very fast growth and lots of capital.

Unless you have a trust fund to fall back on - and it sounds like you don't, with the mortgage and job and all - you can't gamble with your responsibility to your family. Your answer to the question above must be "slow, organic, and profitable," you have to abandon the dream of becoming a gazillionaire with the next big risky "Tinder but for carpooling" idea. Even if you think you have a 10% chance of becoming a billionaire and a 90% chance of losing your house and destroying your family in the next 10 years, versus a 100% chance of holding a boring $100k/year job, the former is not 1000x better than the latter even though the estimated iterated return is $100M/year.

You should either learn to be content at your ordinary job, or you should slowly build yourself enough of an emergency fund/runway to be unprofitable for 6 months to a year, and give a safe, organic, slow-growth business a try. You can call it a "startup" if you want, but you can't burn VC money like it's going out of style. I have no idea what you do, but perhaps building a network of contacts during your current employment, and starting an independent consulting business could work?

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

#65
> if I told my wife I was leaving my job to pursue a start up

Maybe I'm reading too much into this, but is the plan to make a decision and then telling your wife your about it? If no, then you can skip the next part.

If you answered yes, then I have one suggestion for you: ask your wife how she would feel about you perusing a startup. If a startup means dealing with financial risk, more work, less free time, have an idea about how you would handle that. Many founders' startups are built on the sacrifice of their partners' labor, time, and careers. This often goes unacknowledged.

Think about how you would feel if she decided to found a business and told you that you would have to start making sacrifices? If you are thinking, "That is something I would like to have input on," do right by her by asking her before making a decision. You signed up to have a partnership, right? That means meeting her as an equal in the decision making process. This isn't an opportunity to convince her either, it's an opportunity to explore the second and third order effects together and decide together if this is the right move or not.

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

#66

VC here. If you're building a bootstrapped business, then starting as a side project and building up revenue until you can go full time is probably the way to go. If you're going the venture-backed route, I think there's a misconception that there's no salary or minimal salary at early stages when you're funded, but this is not true. Most founders take a reasonable salary, where reasonably is defined more by your per…

Are we even allowed to do side projects? What if our employer claims ownership or even conflicts of interest with what we are building? How will i even present it into hn or producthunt with my name and all my credentials while i am still working somewhere else? Any employer would fire us on the spot if they found out, wouldn’t they?

The answer is, it depends. Different states have different laws etc...

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

#67

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.

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

#69
post #61

VC here. If you're building a bootstrapped business, then starting as a side project and building up revenue until you can go full time is probably the way to go. If you're going the venture-backed route, I think there's a misconception that there's no salary or minimal salary at early stages when you're funded, but this is not true. Most founders take a reasonable salary, where reasonably is defined more by your per…

I think I understand what you mean. Bootstrap = use your current salary. VC = use startup funds to pay yourself but it gets touchy real quick. I currently make 140k in MCOL, so to hear that taking a 140k salary isnt out of the question, eventually, is reassuring.

I think the toughest part ends up being the time between when you leave your job and when you raise your first funding round. That could be a 1-2 month gap, or it could be a year. Best advice there is that you can probably do some of the initial startup work while working somewhere (e.g. customer interviews, spec'ing out a product, recruiting a cofounder, maybe even launching something), so that when you leave your job you can do a fundraise soon and have decent confidence in the company you want to build.

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

#70

I made the mistake of opening a startup with two small kids, another on the way, and a hefty mortgage. I left my well paying job to do so. It was a nightmare. I living hell that eventually broke me and almost ended my marriage. Don't do it.

I hope things are better for you now. It is tough.
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