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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?

#331
> Are all startups at my age generally side hustles that become profitable enough to quit my day job?

Maybe yes. But that's only the first step.

40yo here, married, 3 kids (5yo, 3yo, 1yo), and a mortgage. I am more in the risk-averse side.

I was a CIO ('I' as in 'investment') in a family office. In 2019 I started building a document processing service (eg merge, encrypt PDFs) as a side hustle. It grew slowly and steadly, until, in May 2022 I got enough recurring revenue to ask my employer to reduce my load to half-time, taking a paycheck cut.

In the other half of the day, I am working in a more ambitious idea. I expect that at the time I am ready to launch, the income from my document processing service will be near 100% of my full-time FO paycheck, so I am taking very little financial risk.

Two resources that would have helped me a lot when I was having the same questions as you are:

- Rob Walling's "Stair Step Method" https://robwalling.com/2015/03/26/the-stair-step-method-of-b...

- Dan Hulton's "Evaluating Modest SaaS Business Ideas" https://greaterdanorequalto.com/evaluating-modest-saas-busin...

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

#332
Don't quit your job. Try to take each step at a time, you'll leave the job when you have profit. Meanwhile, you have to work extra hours every day. Your wife won't kill you for leaving your job, but for don't see her enough time.

I'm not kidding, it's tough to keep a job, have a family and start your own business. Be patient, and make your family part of the new adventure (as much as possible). They will understand that the effort and sacrifice are big but the benefits are bigger.

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

#333
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 agree partly. Millionaire bootstrapper here. The part I agree with is to just ask people who have done what you want to do and get an idea of the sacrifice and time commitments involved. The part I DISAGREE with is to wait to do a startup until you’re in your 50’s. This is really horrible advice that can lead to resentment for you and negative outcomes for your family. You CAN start a business and have a family but…

I would throw in one caveat - at least consider delaying launch until your youngest is in kindergarten. You probably won’t be fifty, it’s not that long. Certainly do some legwork ahead of time, but in my experience the earliest years have the least wiggle room. I seriously burned myself out trying like hell to do it all, and in retrospect wish I’d have paused several ambitions for just a few years. In so doing, I’d have been fresh & ready the moment wiggle room returned.

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

#334

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…

I specifically called out "outside business hours"... there should be no overlap. I also don't tend to work on anything near what I work on at my day job. Same for side work to main job.

Again, it depends on the work environment. I haven't had trouble getting permission when I've wanted/needed it. It's generally if your job performance is suffering, or if you are working in an adjacent or competing market.

You've specifically mentioned two things I believe I excluded in my statement.

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

#335
post #190

The typical response (for example, I've seen Patio11 say this) is: don't make your life harder than necessary by including big life changes in your startup journey. Running a company is hard, do it the easy way. That said, I did this with the love and support of my wife -- she wanted (and wants) to help me Live The Dream (tm). We got married, bought property, and had a kid while she worked full time and I started my…

> it's literally the first question most investors ask newbies What's the first question, "is this a side hustle"?

Yes, essentially: "are you full time?"

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

#336
I haven’t read all the comments so apologies if this has already been covered. I started a company 5 years ago, when I was 21. It was gruelling, financially stripping and I had no idea how hard it would actually be. Before I get the comments, no, my daddy didn’t give me money, I didn’t have daddy’s network and we didn’t get a shitload of investment from some well off benefactor. I built it from the ground up, bootstrapping and paying myself sweet fuck all.

But I still did it, and now we’re expanding. There’s obviously a hell of a lot more I need to learn, but I’ve made it further than the vast majority of startups.

The comment I’m about to make has been alluded to, but not asked - which shocks me. There is no one way to do a startup, which to me says while it may be difficult, your objectives are still possible. It’s all about what the variables are.

What is your area of expertise? What is your experience? Who’s in your network? What market are you trying to address? Is there required R&D from the technology side, the logistics side or another side? What skills do you need to acquire to do it? How much capital can you put in? What type of company? B2B? B2B? What is the customer acquisition process? What’s the problem, what’s the solution, how hard is it to implement the solution? What does competition look like (if your answer is “there is none”, there’s a lot you need to learn). What’s your objective here? Sell, manage, franchise etc? What’s your expected exit and timeline? How large are you aiming to get to?

There are a huge amount of questions that are not answered, so any advice you receive will only be general. There is one ‘rule’ though. If it’s your first startup, it will be a lot harder than you think. You’ve got more on the line than I did, I could afford to be wrong. You can’t. Do not be naive, do not be precious, leave ego, arrogance and pre-convictions at the door. Identify your strengths, identify your weaknesses. Build your strategy around what you can do and what you can’t. For what you can’t, go learn, or go find someone who can do it.

If you’ve got a wife and kids, your ambition will have to be curbed to your risk appetite (which seems low for obvious reasons).

Here is my advice, up to you whether you think it’s applicable or not.

People are more important than money. Money won’t give you advice, point out holes, make introductions, guide you. People will. It is essential to understand yourself. The good the bad - it doesn’t matter. Your strategy should fit the tools at your disposal. Whatever you’re wanting to do, find case studies. Companies that are similar (structurally, not necessarily doing the same thing). Look at their pitch decks if you can find them, their business plans, their marketing and what their message is. For the first few months, make this a hobby. If you have an idea, flesh it out on paper. Be o he rove and realistic. The world doesn’t give a shit about what you want, so make sure it’s objectively logical and THINK THROUGH THE CUSTOMER MENTALITY. Learn as much as you can about how to write a business plan. Write one. Read it with the most critical eye you can, be your own devils advocate. Write a new one. Do the same. Repeat. When you’re happy with it, and you actually think it could work, find business mi fed people you respect (professionally or personally) and get them to read it as a devils advocate. Do that for a minimum of 5 people. Collect response, do NOT ignore feedback just because you don’t agree. Find out why they reached that conclusion, you might learn something. Talk to your potential market. Cold call, rock up, fly a blimp - however you do it, talk to your potential customer, ask what problems they have, would it be sold with your product/service, what would they pay. You need feedback from like 100 people on that one. Your ideas, plans and perspectives MUST change according to new information. Always.

If you’ve reached the stage where you e got your feedback for a solution, got a good business plan, it’s time to work out how you’d actually do it. What milestones, what goals, how, why, blah blah blah. Whatever you think something will cost, add 50%. If it’s less than you think, you’ve got money to do more. If it’s more, you’re fucked. Don’t fuck yourself. Be very aware that you can be your own downfall here. I’ve said it before, but I’ll say it again: fuck your pride, fuck your ego, fuck all the things you think you’re the best at - if you can’t do that, don’t start a company. You must CONSTANTLY, objectively and thoroughly asses yourself, your plans, your tools, your backup plans etc. if you do this and quit your job, don’t be a financial dumbass. Have a backup, have a plan. Know how you’ll get income if the startup doesn’t work out.

I disagree with most people on here saying that you can’t do it. Every startup begins with a set of tools, variables, restrictions and risk. There’s a way to do anything, but with what you’ve got on the line you cannot afford to be ignorant, and you cannot afford to have a fail safe.

I don’t know what your motivation is here, but consider alternatives. You want a thing, and the way to get that in your mind is to make a startup. Maybe there are other ways to get the thing that isn’t running a startup. Maybe change careers? Learn something new? Join a startup?

Go to networking events for startups, and talk to everyone.

Above all, LEARN. about yourself, about the market, about others experience, about business - everything.

This is all just my thoughts of course. I’m just me, I don’t know you at all. We’re in different countries an all of that, but this would be my advice.

Good luck!!

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

#338

Earlier quoted context omitted.

Agreed 100%. When people ask me what the best time is to work on a startup, it's always when you have no dependents, living with parents, and perhaps no significant other. It's quite amazing just how much you can skim down your expenses at that point in life. Minimizing expenses, maximizing runway. The rest is luck. Just blind luck.

Alternatively, maybe your dad owns an emerald mine? Always an option!

This isn't true (since 89)

https://www.snopes.com/news/2022/11/17/elon-musk-emerald-min...

Keeps coming up, even though it's a pretty easy google.

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

#339
I have been in your shoes. Here is what I suggest:

Do not start if you don't have 6 months of your cash flow in the bank. Do not start if you have outgoing monthly commitments like home loan, credit card outstanding, bank loans, medical expenses, etc. put together at 50% or more of your monthly earning. Do not start if you don't see regaining your current monthly earning within 6 months.

Trust me this has worked for me and 100s of others whom I have mentored/coached since last 15 years.

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

#340
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.

Great story. Did you have a family with kids at that time as well?

Thank you! Yes, Natalia and I had two little kids and Dave and Sara just had a newborn at the same time
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