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

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 identifying great opportunities.

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. If you have a solid job that allows you to be there for them, take it and be amazing in this potentially incredibly rewarding role.

Then do an awesome startup when your kids are out of the house, you have a solid nest egg, and you can take risks again in your 50s.

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 personal needs than anything else. $100k-$150k salaries are pretty common at seed. That's not Google level, but it's not bad. Here's a thread on that: https://twitter.com/lpolovets/status/1365123608905879555

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 the business without building anything, IE: via spreadsheet or email, or a simple Wordpress site rather than something more elaborate? Partners are complicated - on one hand they lift the burden of doing it all yourself, but now you have a business relationship to manage; there's got to be a lot of trust there.

On the other hand - there's never a good time to do anything. There will always be a reason why now isn't the right time to pursue whatever you are considering. And, your spouse matters a lot. Whether they are supportive of who you are and what you want to pursue in life is one of the key ingredients of potential success. I'm not suggesting you trade one for the other, but you'll need to be very candid with each other about your goals and needs. Don't try to parent and spouse and career at the same time - dedicate time to each and be very clear with each other about which "mode" you are in, IE: spend Saturday completely with the family. Make sure you are supporting your spouse and their career / personal needs, but also set a rule 5-10 M-W-F is your business time (IE: whatever it is that works for your life schedule and needs)

We quit our full-time jobs when 1Password revenues were close to $80,000/year.

1. My wife works in a well paying field (nothing crazy, but comfortable), and we were financially stable enough to be able to live without my salary for a couple years.

2. We were very customer focused from day one, even before we incorporated. We signed up several customers (using LOIs) with just a deck, before we wrote any software.

3. We discovered a very clearly defined problem, a payer and clear willingness to pay.

4. I don't work like I used to. I feel much wiser about how I spend my time rather than brute forcing it with hours. Because of the two kids, I effectively work 9-5, M-F. I don't work weekends. During 9-5 though, I am dialed-in (I don't spend time reading the news or checking instagram). I delegate much more aggressively than I used to. I don't think I'm actually outputting much less than I used to, I'm just more efficient and focus on the more important things.

5. Venture - this is what it's for. There is still a bunch of venture out there for seed/pre-seed. We raised money early on and that allowed us to take small salaries (and hire folks to delegate things to).

100% it's definitely not as easy to start up in this stage of life, but it's also not impossible. Happy to connect with folks who want to connect (commiserate?) about this situation.

I've done exactly what you're trying to do. Let me give you the playbook.

In preparation, I've done years of research in the field I'm working on (APIs, Integrations, developer experience). So you need a clear advantage.

Next, choose a topic that you're thrilled to be working on for many years. Doing this means you have to eat a lot of glass. It's crazy.

Commitment. Be ready to work through weekends and nights. You will feel bad because you won't have time for kids and wife. Your wife must 100% support your endeavour. It will be tough. Don't kill the relationship.

You need co-founders. Don't try this alone, it sucks. Build a small team around you. I found 3 amazing co-founders, a COO, a marketing genius, and a hacker. You can use tools like YC cofounder match. A lot of people will be a bad match. Meet a lot of them and try out things.

Build whatever you can to get one single customer, that's a person who pays you money. For us, this was enterprise support from the first customer at $2k/month. This changed everything.

How do you do this? Fuck everything. Stop building. Talk to potential buyers. Get someone to give you money for what you're doing. No money, no value. Whatever it is, get some MRR.

The last one was my biggest issue. I kept building because I loved building so much. But I was just coding, not creating Business value. If you're able to ship any kind of MVP with your co-founders, you're able to get some MRR, that will give you angels, and finally you can raise a seed.

All of this can be done on the side. Keep your job as long as possible. Get that one customer, get the angels and a SAFE for 6-12 months and then double down on that first customer, improve the tool, get a second customer maybe and raise the SEED.

It's possible. It's going to be tough. But you can do it. If you need my help, I can mentor and give you the right intros. Best of luck.

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?

I also agreed that it would be an ABSOLUTE rule that I could not put any of my own money into the company. This included the $10 for buying the first domain.

I ended up selling 20% of my company to a friend for $5k when it was just weekend hacking with him getting diluted to a $2.5m valuation once I've been full time for 40 months.

[Edit] It massively helps that my wife is a partner at a law firm so we can pay bills etc, without having to have saved the cushion in advance. I also arranged to leave my previous employer with a 6-figure exit payment.

1. A supportive wife 2. A wife that can pay the bills while I take 0 salary to build something.

Without those 2 things I wouldn’t have been able to start.

As I’m sure you realize now that you have a wife and a child your free time is limited and at bad times. So if you want to actually be able to accomplish something you have to pull real time away from something else.

Your choices are 1. Your family 2. Your job.

You could try going part time and asking if your wife is willing to do an outsized portion of the family work but that goes back to (1) being critical. First and foremost you need a wife that will support you.

I know this probably isn’t helpful but it adds a datapoint for you.

My experience:

- It's hard, if your playing a video game it would be in `very hard` mode

- Talk to your wife beforehand, she was okay with the opportunity

- Had a LOT of savings

- Have a co-founder (highly recommend it)

- We've raised preseed money (co-founder handled all of that)

- I hired an ex-coworker that I worked with previously (that's why you raise money)

- I'm remote so I get to spend more time with my baby (if I'm not productive during that day I try to code long nights and usually feed the baby during the night so my wife rests)

Overall it's been super hard but gratifying :)

PS: I also try to exercise for an hour a day to keep me sane

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.

The wrong time to work on a startup is when you just have a vague desire to work on a startup but don't have the passion for solving a specific problem but just feel a vague pull towards startups. In that case, you are much better off joining someone else's startup.

You can make long hours work out with family life and having kids, people do it all the time who are not involved with startups but work multiple jobs, lawyers who work long hours, etc.

Long hours per se is not the issue, spending those hours on the right, productive thing is the issue.

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.

Why do you want to start your own company? Is it because you’re sick of answering to people, or because you believe you have a genuine solution to a genuine need.

Aside from all of these points, the brutal reality of starting businesses is that it can be very risky and capital intensive, if you have doubts, you should consider why.

Over in the UK, many in the startup scene appear to be from upper middle class backgrounds or ex-bankers/finance. These people have security through assets they have inherited or earned.

Aside from that, you can be a contractor and grow your customer base from there, this is likely to be less risky.

https://robwalling.com/2015/03/26/the-stair-step-method-of-b...

He has also talked about it on his "Startups for the Rest of Us" podcast:

https://www.startupsfortherestofus.com/episodes/episode-222-...

Might be worth trying Rob's approach before leaving your job and betting the farm on a startup idea...

First, make sure your partner is onboard and is supportive first. Have the discussion about the sacrifices needed to make it happen (time, money, lifestyle shift, etc.) Something that helped us was to set a goal of what we wanted when things eventually worked out. This kept us sane and helped me continue to be motivated during hard times. We lived in a pretty low cost area (NC) and managed to get our expenses down a lot.

I also made sure to spend my weekends with my family and my wife. I took over a lot of the chores on the weekends. Communication was key for us and when issues came up, I tried to resolve them ASAP.

Start working on your startup between 5 PM to midnight. Bootstrap it as much as you can until you can make ends meet, then quit your full-time job. Apply for YC and others while still growing your business if you think it has the scale. Eventually, it either works out well or poorly.

You should also consider what success looks like for you. Do you want to start a company to gain creative freedom? Do you want a better lifestyle for your family? Are you prepared to spend the next 7 years on this endeavor? How will you balance the high workload (I'm talking non-stop work for a month at a time) with spending quality time with your family?

You should think through all of these questions, then have an honest conversation about it with your wife, and don't sugar-coat it. She might surprise you.

As far as funding goes... You'll want to put away a fund to pay your salary for at least the first 6 months. Your goal in those first 6 months will be to create a believable story you can sell to investors about your vision. If they like it, you'll be able to raise funds to continue working on it and to deliver that vision.

At least, if you assume you could have it all, there's a good chance you'll come short notice n a few categories.

I ask because I know multiple talented people using this as an excuse to not use their abilities as they claim they want to.

My ignorant guess would be people these days think you need to spend a ton of time with your family because other people blame their problems on absent parents? That's why I'm asking to be educated so I can be less ignorant about the burden of parents. Naively, if I had a kid (not that I plan to, don't worry lol) I wouldn't care about spending time, just feed, clean and transport, not that much worse than pets burdenwise. I would expect kids and spouses to understand the nature of the real world (when they grow older for kids).

She accepts the risks and wants to see me try to follow my dreams rather than give up. We've moved back in with my parents to save money and help with childcare.

Once I can secure some investment, it should get easier -- at least financially, if not in terms of work hours. That's also difficult these days but we'll see how it goes.

It was a nightmare. I living hell that eventually broke me and almost ended my marriage.

Don't do it.

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...

A couple of concrete examples of what an asset strategy is:

* An options strategy that helps you yield every so often (example - buying tobacco and alcohol options going into the recession hoping they will yield higher when people tend to drink and smoke more) * A real estate strategy that minimizes money exchanged in-hand (example, looking at housing markets that are starting to become distressed, buying a foreclosed property, and then flipping it to someone else who would buy it for more but doesn't check the foreclosures listings)

^ There are many examples. It won't be quick money, but you need to get to a point where your assets are generating enough money for your marriage to not fall apart in the very likely scenario that you will fail starting your own company multiple times.

I want to say, I have no idea if this is actually the right sequencing of events for you, but it seems to be if quality of living is a top concern (which makes sense). If you want to maintain a standard of living while taking on massive risk, you need to hedge with a diversified asset portfolio that generates income for you outside of your job.

Here's the kicker: My co-founder and I both have kids, family, mortgages. Here's how I did it in the years leading up to and during:

- I saved for years with the idea that I was going to use that money for entrepreneurship

- I was upfront with my spouse and kids about the amount of effort, risk and potential rewards; i could point to a successful dev/PM career as evidence that I could succeed

- Keeping the same standard of living was impossible, we had to budget for a new level of comfort

- We had runway timetable in mind to show some progress

- Our business approach had to be profitable from the start

Your business failure rate doesn't need to be 90% if you're flexible about the problem you're pursuing. We chose an idea that allowed us to bring in at least a little money to lengthen our personal runway. Once we had a sustainable business, it was easier to approach investors and pivot slightly to the market dominating, high risk/high reward version of our idea.

Hope this helps! Happy to chat about this with anyone who's interested in doing the same! f at howdy.com

1. Saved money through normal tech job and paid off obligations where possible, so expenses weren't too high and savings were good. So the risk of trying something on my own was manageable.

2. Left my tech job, but did consulting first for a few years. Easy to go back to a normal job if consulting doesn't work. Used savings to get through the initial period of figuring out how to do consulting. Really nice to have some kind of side income in this period - like teaching online courses or whatever fits into your skillset.

3. Built up money through consulting, but also built up contacts and partners in the target industry.

4. Pivoted from consulting over to the start-up in the same industry when the timing was right. Could have fallen back on consulting if the company failed. The nice part about consulting is you can split your time between paid work and your own work in whatever ratio you want, so you aren't ever jumping off a financial ledge.

It's not like this was some master plan. But it is how it worked out for me and we were thankfully relatively stable at each step.

As far as the company itself, my advice would be (1) Find really good partners you trust that are good at what you aren't good at. Being good at programming is maybe 20% of starting a tech company. (2) Don't up-end your life to start a solo side-hustle SaaS where you are convincing people to pay you $19.00 - find a real industry with real money to spend. Or alternately, keep a side hustle as a side job until it actually gets some traction.

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.

My cofounder previously started and failed at another startup, while taking bare minimum salary. It almost ruined his marriage and was terrible for his mental health. We're also just over a year into this, so we'll see if the higher salaries works out or not.

The answer is simple. You keep building on the side part time until it can become your full time thing. There are plenty of success stories from people in their 30s with families who made the transition (rare, but there's plenty).

The biggest thing for me was mitigating risk. I have a full time job that I'm keeping while doing this, and I've leveraged things like using Wyoming for an LLC to reduce fees and cost of having the business entity, and startup credits on cloud providers to kick off the business at minimal cost. If I fail, I probably won't be out much other than the time I've invested and about $1000. Worth the risk of another income stream, and a better bet than the casino.

Also want to add that my top and first priorities are my children and financial responsibilities. The startup comes second.

The key is that I didn't jump into it full-time right away. I first transitioned from a full-time job to a successful freelancer/consultant where I continued to get paid for writing code, but controlled my time and commitments. At first, I did this full-time and out-earned my previous employment income. As the startup itch grew stronger, I started spending more (unpaid) time on the startup and less on clients. My income dropped significantly (to about 30-40% of peak earning - ouch!) and it was a big sacrifice and gamble. My wife had some part-time income and maternity leave income during these times, but nothing too crazy - I was always the major breadwinner.

My wife and I also were on the same page about living within or below our means. We always earned significantly more than we spent and could tolerate major reductions in earnings and still not dig into savings. That's not to say we earned a lot, but that we were smart & frugal with money and did not have $$$ lifestyle preferences.

Also helpful that I live in a country with universal healthcare. If my family's health insurance was tied to my job, I would never have become an entrepreneur as I am very risk-averse. Keep in mind, all that happened above was a gamble that I took. I got lucky with the outcome (through a combination of skill, luck, and timing). There are many scenarios that could have played out, some that would not lead to success where I would still be bitter to this day about the career and financial sacrifices I made. I took the gamble and won, but it could have easily gone the opposite way. What I do know is that my wife would have supported me in any scenario. How I myself would have handled the mental impacts of "failure", I'm glad that I don't have to find that out...

I’m a night owl so I usually spend time after kids are in bed working on it. A lot of people say they find success waking earlier and getting in a couple hours before their job/family routine takes over. I think the main thing is to make a plan and talk to your spouse and ensure you’re aligned.

We wanted to work on wildlife/animal tracking and identification through technology. It was very hard, the limits are physical and geography and weather hate tech.

You can do projects for other people to fund it. We gave up on the animal tracking idea and pivoted and found a lot of the tech transplanted to other sectors.

You say you want to start your own company but also pursue a start-up. Those are very different models.

Do you want a business that you can work at or are you looking at fast growth and sell-out?

"The majority of businesses, on average, do not start turning a profit until as late as the third year. Some can take up to five"

I think you need to be clear on your goals first and then how to achieve them. Starting a company isn't a goal, it's a by-product.

So the short answer is that you can absolutely do this. It's about how you approach it and ensuring the people close to you are on board for the ride as well.

1. Bootstrap a side hustle

IMO starting a side hustle that becomes profitable enough to quit your day job is the best strategy here.

There are very few SaaS ideas that will produce $B returns in <10 years. They're all highly competitive with well-funded competitors.

However, there are easily thousands of SaaS ideas that will produce $10k/mo (with 90% margins) in the next 1-2 years. Take pretty much any existing SaaS product (eg. Segment, Zapier, Intercom, Jira, etc) and build a simpler version with nicer design for lower pricing, and you can get paying customers.

Once you're making $10k/mo (or even less) and growing you can probably quit your job and then that frees up a ton of time to invest in the existing business or a new business.

2. Buy someone's side hustle

Check our Microacquire. Tons of people are buying and selling SaaS companies on there.

If you have some money saved up, and some risk tolerance, you could consider buying a very small SaaS business (eg. $1k-2k/mo revenue) and growing it from there.

Even if this isn't an option for you, it's probably a good idea to check out Microacquire anyway to get inspiration for ideas for SaaS companies for #1.

3. Raise a pre-seed round

Try to find a VC firm who is willing to give you some money to spend time starting a company. This will be easier if you have a) a good background, b) a good co-founder, c) a good idea/big market and ideally an MVP.

That's kind of what the pre-seed round is all about. It gives VCs exposure to get into your company early at a great price, and it gives you a way to work on your idea while still making a salary.

4. Apply to be an entrepreneur in residence

A lot of VC firms have EIR positions where you basically get paid a salary while you're trying to decide what startup you want to start. The idea is that when you start a company you'll raise your first round from that VC firm.

Instead, figure out what business idea you can accomplish that would have a 10% failure rate -- a 90% chance of success.

While you're doing that, accumulate capital, so that you have at two years of complete living expenses in the bank.

When you have both of those things, you can discuss taking a year to do a startup, with a one year ramp. At the end of the year, you evaluate:

- is this close enough to success that you should definitely continue?

- is this almost ready, and you are no more than 3 months away from a go/no-go?

- is it time to end it, take a couple of months off to be with your family, and then have 10 months to look for a new job?

To become a billionaire? To leave your job that makes you sick? To have a more exciting job?

I am mid-30s 2kids good, not crazy paying job (think 160-200k$ range TCO) and spend time with kids and travel 1-2x amazing trips a year with them. I decided not to give up that precious time and don’t regret it so far. But what I did is change companies until I could find that dynamic startup vibe with a good salary. I would even take the risk to go to a smaller company slightly less money but with shares/options. Up to you, but answer the « why » truly honest is my advice…

Take a look at some ideas that can be done as a solopreneur, parallel entrepreneur, or with a self sustaining small business that doesn't require a ton of capital or reoccurring expenses. Don't overcomplicate things or add a ton of stress to your life and build a product or service that you simply can put out there to see if anyone responds. It's important to note that not all startups have to be technology based or what everyone calls a "startup" here. You can be an urban farmer, or sell simple products that you, yourself have been wanting to find in the market. Talking to your local SBA office doesn't make you less of an entrepreneur than launching on HN either.

If you're unsure if an idea is worth it, put out a landing page to see if anyone cares about the idea or what you already have to offer. Spend a weekend or a few nights here and there and make something you're nearly ashamed of, then go try to sell it. You'll learn along the way what works and what doesn't. You'll also learn who you truly are and what you can do and handle. The only thing you need to know is whether or not people are buying what you're selling, and you can live with what it takes to make that happen.

I'm a huge fan of the advice that is contained in the 37 Signals / Basecamp books, so feel free to check those out to learn more about the themes I've suggested here in a better, more articulated package. There is also a book titled "The Parallel Entrepreneur" by Ryan Buckley that I've found useful too.

Good luck on whatever you find yourself working on!

Leaving work to pursue a startup should only happen when you can prove well enough to VC's you're accreting revenues just barely worth investing in (to very worth investing in). If you're sane, I would wait until you can't move forward without some seed/VC and then look around for it- starting with people you know, and familiarize yourself with how funding/ownership/etc works.

You don't need to go through ycombinator, although its very worthwhile, you can just run a startup on the side or quit your job once its up and running.

If your startup is a unicorn, maybe wait a year before quitting your job, so the job market is ripping again when you fail :)

Before I started my wife and I calculated by how much we can reduce our spending and figured that between her salary and our savings we could go on for about a year while maintaining an acceptable quality of life (for us) and not going into debt. While I was going through this her pay went up significantly (and unexpectedly), which allowed me to extend my personal runway. In the end, after ~four years, we were left with no savings at all and I had to take a job I didn't like because I had to start bringing money in. That was fine - I quit after a short while for a much better job. So the key was planning ahead financially and agreeing in advance on the limits: minimum standard of living we won't go below, and not going into debt. This proved very important in hindsight because it marked when I had to stop trying - I never wanted to give up, but had I continued, I would have jeopardized the most important things in life.

Another point about the marriage: my wife and I are together in this journey called life and support each other's hopes and dreams. I paid most of our bills while she was going through her PhD, then she did (plus we spent our savings) while I was doing the startup. Now I'm doing well, so she took a partial leave while she's pursuing hobbies and trying to figure out the next step in her career.

If it was known how to make money right away, everybody would start a start-up right away. But there are so many brilliant ideas, you just never know if they are going to work. Sure you can try, but the risk is there - as you said yourself.

If I were you, I would sit down with my wife, discuss pros and cons and also make clear why this matters so much to you. Hopefully you'll find a solution together!

First off, young kids (<6) need parenting attention. If you want to go hardcore working side-projects and a fulltime job OR more than fulltime without income then that's going to push a lot of the work to your wife. Even if she's fine with it, usually your kids aren't. After 6 it gets easier.

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.

1. Do it on the side, while working.

2. Save up and then go full time.

3. Borrow money and go full time.

None of them are easy or stress free.

I went for option 2. I worked like crazy and was making roughly my old income after a year or so, so I never burnt too far into my savings. There is a bit about my journey here:

https://successfulsoftware.net/2013/11/06/lifestyle-programm...

1) Salary: you should get some seed funding (500k / 1M), leave your job, and then immediately pay yourself a salary. Your seed investors should know about this.

2) Marriage: economic uncertainty will play a mayor role in this. Make sure you discuss your intentions with your wife before doing anyting. Try to understand what her biggest concern is. Try to address it. (e.g. show her you can easily get another corporate well-paying jobs if this doesn't work out; show her you have savings to not feel too anxious about this).

3) Do you want to start a company, or do you want to solve a problem? Important difference here. Meaning: do you dream of lots of money, glory, keynote at Techcrunch Disrupt, etc, or do you really feel an urgent need to solve a particular problem, and starting a company is simply the easiest way for you to scratch that itch?

4) Being in your 30s is not a negative. In my experience, it's actually a positive (you know more about life, work, tech, etc, and you still have a ton of energy to spend on it).

Edit: I should have added: I started two companies, I (still) have a wife with no kids, I also had a corporate job for a dozen years, I advise and advised many startups in general, and a few times in regards to an issue like this.

As soon as you’ve crossed that line and had said kid, you have just made a conscious choice to significantly reduced your own time, finances; and flexibility available to chase after personal goals.

Before anyone immediately @‘s me; this is not always the case…but usually the people who can do both are 1) the exception to the rule, not the average; and/or 2) were relatively wealthy. maybe you can afford a caretaker for your child.

But that begs the question - so you had said kid, and want to give said kid the best life they can. Cool. We need people.

Probably adopting is the more sensible option; since there are tons of kids in awful, hopeless situations that can use your help, and we also have an overpopulation issue; but honestly, some people just want to have the experience of having kids. Okay, cool.

So…Does starting your own business right now, rather than investing into your kid’s development, really make sense?

By having a kid; did you not agree to set aside a lot of your personal time and finances to them?

Shouldn’t you do this sort of thing before you have a kid or after they move out? What if it takes off and your kid loses a parent being present because the career took over? :/

Asking from the perspective of a 33-year-old woman who sees having kids in your early 30’s; or, God forbid, your 20’s, as suicide of independence.

Not sure how much this applies in 2022, but in 2020 I started a company with a wife and one kid. Since then I've had another kid.

Here's how I did it.

- First, and most importantly, I didn't leave my previous job until I could draw a salary from my new company. This meant waiting until we raised a round of funding.

- Second, to raise a round of funding without a product, you need at least one of the following. 1.) some semblance of traction. For B2B this could be letters of intent from potential customers, a waitlist, etc. Anything showing that people actually want the thing. You would build this while employed elsewhere. 2.) previous success building and selling a startup.

- Third, to justify drawing a salary as a founder, you really need to be doing things that otherwise you'd hire people to do. This means working insane hours (80+ per week). I'm never really not working. Luckily I enjoy my work, and I still find time for my family. It just means I'm working randomly in 2-4 hour chunks pretty much 24 hours per day. If you're not ready to do this, or your family isn't, then don't start a startup.

Every path is different but I think there are a couple of guidelines that I recommend: - Talk with your partner and set expectations from the beginning. Please do not romanticise the journey - it's damn hard and full of sacrifices. Others have suggested a deadline - I also did that but find it a bit unrealistic because you'll have excuses to continue devoting an unhealthy amount of time to your company. Be kind to your partner and acknowledge that they will take more load in family duties and you'll have less time to spend with them.

- Find a co-founder that is complementary to you and that you trust. Being a solo founder in your 30s with a family is super hardcore even if you already have found product market fit.

- Do not invest your own money. Finding an early champion of your project and your founder team that could be an angel investor to kickstart things is a must. The alternative is to do it as a side gig until you can reach some kind of Ramen profitability scenario - I'm not a big fan of this because you'll likely focus on revenue too early on.

Happy to chat about my experience if you think it'll be valuable (just DM)

Pretty much yes. There is nothing wrong with it. Don't leave your job and don't forget your responsibilities. I am too doing this between kids sleeps etc whenever I find half-a-hour free to work on my projects. Yes it's slow and overwhelming but still a progress. I hope as kids grow, there will be more free time available.

Short answer: yes, its possible

1. Find your niche and work 1-2 hours every day to create a strong pitch (a prototype and ideally a few early customers) - consistency is the key - EVERY DAY. Act with urgency here. 2. Raise a pre-seed round - this is when you quit your job. Yes, you are selling equity in your sweat. But there is no free lunch - you want to keep the living standards and also, stop working full-time for someone else - you need cash flow. There is a probability that you identify a really good problem and you grow customer base really quickly - that is very less likely in my opinion.

Once you have some capital, you'll have a larger canvas to paint - it changes the mindset to be faithful to people who trusted you with their money and also, brings in so much of focus.

There is the whole weekend hustler concept - I am not a big fan (I made more progress in 2 months full-time compared to what I could make in 2 years working on weekends)

What's the worst that could happen? Just do it.

Two mantras for you: Focus on intent; Always measure impact

1. Your skills - Why? - How much you need to spend on Human resource? to reach PMF

2. Real dependancy on you of your family - Is your wife working/side passive income etc so you can ditch your job

3. Your Startup/Product Idea & how much time will it take to reach MVP and ramen profitable -

4. Your family's willingness to *sacrifice social pressure*. - Scarifying lifestyle/current standard of living is hard, more harder is to get rid of "What other people/social circle of your family will tell/think" of the new lifestyle,

5. Opportunity cost of doing job (or leaving job).

Most of people have hesitation of leaving job, so exact decision you only need to take (or not take).

Advice - Don't regret on whatever decision you take.

Let's say if you stick to job and same idea/product someone else become big big, No need to regret and vice versa.

Context about me 1. I left Software job after 7Yrs and bootstrapping since 10+ yr. Ups and Downs are part of life. COVID has made life bit worsen (as we are in daily commute!) 2. I am 35+ yo single, My parents don't depends on me, No-Unwanted-expense, from India

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 company.

Even with her support it's been brutally difficult. My entire life runs on hard mode.

I recommend thinking less about maintaining a standard of living and more about acceptable tradeoffs.

A perfectly acceptable tradeoff to most people is to NOT start a company. If closing that door causes you grief, my condolences -- you'll have to do it the hard way too.

And: side hustles are, IMO, procrastination traps. They're a linear attempt to solve an exponential problem. Work will feel like progress but actual traction is hard, family life will always be a pleasant distraction, and investors will rarely take you seriously (it's literally the first question most investors ask newbies).

It's possible. I started a company with my co-founder three years ago. We both were mid-thirties with kids when we started. We've since went through YC, raised a seed-round, and the company has been growing ever since.

What worked for me:

- I saved up money and drew from that while we were getting the company off the ground. My co-founder and I went close to a year without a salary. Having a spouse that works also helps.

- Having a relatively low cost-of-living helped. It never felt like we were reducing our quality of life, although this was in the middle of the pandemic so we weren't able to go on vacations etc even if we wanted to.

Building a company is a lot of work, but that's true regardless if it you're married with children or not. I think parents have the advantage of being forced to be efficient with their time. It did require a lot of work after-hours coding to get things off the ground, but I probably would've been coding on something anyway.

2. Have you done market research? Needed startup capital? Have enough connections that in the case of failure you can just go back to a similar job in the industry?

> Im not sure how to pay my bills while looking for product-market-fit.

Yeah, you're going to want to test this before quitting your job. I think realistically if you can't get at least 2-3 paying customers for your product without quitting your day job, your chances of making it are pretty slim.

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

For someone like you, most likely yes. For someone who's a serial entrepreneur, probably not, because they can rely on their prior businesses to test out new ideas.

Now I am back being a passive, full-time employee that gets to spend some family time and not really getting into side-projects now because I know I can't - I do not have the time now - not with a kid. What I have come to terms with is that I need to arrange some financial safety for my family if I wanted to explore building companies. This is 100% possible. You can explore opportunities or get someone to join you as a co-founder and once you have funding, you can get paid a base salary that you and your family are comfortable with, along with an agreed-upon equity. In SF Bay Area, it's quite common for founder base salaries to be close to $180k or so, so it's more practical than you think.

My advice to you OP is that, if you have a kid, do not consider engaging in side-projects, but rather go all-in and pursue something as a full-time effort. You'll know if things are going north or south within 6 months. If no kids yet, you can make the side-project thing happen, but make sure to have cofounders and split the work. Focus on getting your MVP out the door real fast so you can acquire funding and make your side-project a full-time project. Considering these learnings, I am just holding off for now but I'll make a leap into entrepreneurship again.

- Don't start a company to start a company. You will be miserable. Find a space you like and start to explore it for fun (at first).

- DO NOT quit your day job. Nights and weekends to start. Have your partner pick up more kid/life duty if they is can. Quit when it hurts or when the path of your business lowers the risk sufficiently.

- Focus relentlessly on business model fit and real customer problems. B2B is fertile territory. Niche ignored industries with high painkiller need (vs vitamin) are fertile territory.

- Work with a team. Work with a team with no kids. Probably the most important part. :)

- Treat the work time a normal part of your life (like going camping or exercising)

- Ignore all hustle porn start-up mythology nonsense. Build the business around how you want to work that still achieves your goals.

- Its never easy, but its not impossible.

1. Found a business partner who bought into my vision for the company.

2. We BOTH sold our houses to get equity out for the business and also so we were not stuck with a large mortgage. We then rented less expensive homes.

3. Business partner stayed working at his job and he split his income between our families 50/50. We considered our value equal, so I worked the startup full-time and he worked his job full time. His income was not enough to cover all of our living expenses, but it certainly extended our runway.

4. We met every Saturday for about 4 hours to work together.

5. This lasted for 3 years until we finally make the company profitable.

6. Business partner then left his job and joined company full time.

FWIW, I always tried to start something on the side but never had enough time to fully bring it fruition. When you go "all-in" like we did, you have a lot more pressure to make it work (which is good). Most of my side projects were always kind of "half-alive".

It can be very frustrating/challenging to the part of you that wants to do the startup to do this, of course- that frustration in itself is valuable experience. The reason so many have successful startups in their 40s and 50s is not because they tried and failed at startups in their 30s. They didn't, and instead found ways to improve their impulse regulation, decision making, relationship management- and their financial standing. Speaking very much from personal experience, so much about new ventures becomes easier when equipped with strengths in these areas.

Manage the dopamine. Don't let it manage you.

Best wishes.

The optimistic part is that you could theoretically work up to doing this when your kids are a bit older. Not necessarily full adults, but maybe.

For me personally I'd reduce the choice to "Would I rather have a good relationship with my family and self or sit in front of a computer even more, to possibly compromise everyone's well-being or come out with more money?" and that choice would be obvious.

Check if your government can help you start your own business.

For instance in France, you can sign up for a program called "Aide à la création d'entreprise" [1], which gives you the rights to access like 1 year of your unemployment insurance compensation ("indemnisation d'assurance chômage"). If your income was 2 or 3 times above your spendings, it should be way enough to maintain your standard of living during 1 year, while working full time on your project. Then after this period, if you project didn't succeed, you can move on and look for a job. You basically take 0 risks.

[1] https://entreprendre.service-public.fr/vosdroits/N16153

The first thing you have to do is make sure your finances are stable. That means make and follow a family budget, cut what is unnecessary, bank everything you can, and build 3-6 months of living expenses.

If you aren't willing or able do that as a family, you are not ready to go out on your own.

BUT during that time, you're not sitting still. You should be sketching out ideas, talking to prospective customers, getting feedback, and adjusting as you go. You may even be able to build UIs or potentially an MVP, do it. You're still in a VERY low risk stage.

If you aren't willing or able do that as an entrepreneur, you are not ready to go out on your own.

If you can accomplish BOTH of the above, you should have: a better conceived idea with real feedback, a list of prospective customers, a family on board with what you're doing, and the savings to give it a shot.

THEN you're ready.

If you do one just make sure you’ve got enough financial independence and most importantly an idea that folks think is significant. Are people willing to pay for what you plan to develop? How much time will that take away from family? Can you get funding through an accelerator? What sort of a financial hit are you going to take? Is your family onboard with it?

If your wife has a well paying job and is secure in her work she may be on onboard with limping on a single salary until you hit pmf (or get to a point where you understand there isn’t one).

In the end it’s about financial independence and time your family demands from you.

If you can push to 50-55 hours a week by e.g. working a few evenings a week, you may be able to make it work through a combination of contracting, outsourcing, and grit. (If you do not do a B2C startup. Those are harder!) There's no hard formula, but the basic idea is you can likely earn enough to survive through contracting for ~50% of the hours in a year. Relentlessly triage your MVP and launch quickly to paying customers. Then either reinvest the proceeds into labor in lower-cost countries to iterate on the product, or take a hit to your billable time to do so yourself.

If you get to $X,000 MRR, remember you can likely sell the business for a decent amount of money and start again from a more solid base.

Some entrepreneurs start a side hustle, work on it in their spare time, and if it starts making good enough traction, then pour more into it. Have you considered this path?

Seed funding is still quite active although growth rounds are depressed. Hit up all your contacts, everyone you know, you might be surprised at who knows who. Worst case try crowd funding.

Ranging from humble "providing okay level of life for the family" to ~1B valuation company (it's not 1password mentioned here, but comparably known company in its niche).

2 key insights I've got from those cases:

1) you'd better have a rock solid healthy relationships in your family

2) you have to become a god of time management and work prioritization

Most of them followed "classical" startup path of building a prototype while living on savings -> raising first money to survive death valley -> raising next rounds to scale found market fit.

Though I'm sure there are plenty of "side hustle solopreneurship" examples too.

TL;DR for me — it's doable? Yes. It's easy — hell no!

I think you personally know the lifestyle will dramatically change - even if you take the money / income out of consideration by raising a lot of money from the jump. The time commitment alone will change things!

It’s an incredibly difficult and personal and even somewhat selfish decision that requires you to get the family onboard to somehow support you since it will effect everyone.

This is in fact your first sale task, that you must try and focus on.

—-

Here’s my experience-

About two decade ago I was in your exact position- but luckily for me I had a side project that was showing promise but nonetheless it was a risky and consequential decision to make with a young family.

My wife at the time (hint) didn’t believe in entrepreneurship or startups for that matter. She was raised that a corporate/stable job meant success (which it does in may respects), whereas I was raised a hustler and I knew from age of 9 that I would be an entrepreneur. We couldn’t be more different…

The options were - 1) hold on to a job forever and live a missable / depressed existence (not good for everyone) 2) Somehow convince her and family (yes in-laws included!!) that it was worth the risk or 3) pursue my life’s calling without approval anyhow and risk everything.

Obviously, options #2 is ideal but for me it ended being #3 (after almost 9 years of trying) - which effectively ended our marriage. Regardless of the choice , it would indeed doubly suck if business doesn’t make it - so keep that in mind (failure is not an option mindset)

I’m not saying that’s all the options you should consider… but since you asked for experiences I thought my experience might help put things in perspective for you.

Since we bootstrapped, I basically built the app on the subway ride there and back, and a few late nights. There were very few weekends because I didn't want to miss out on time with my young kids.

I will say though, that the company was basically dead before we were able to pivot our product and use it in pandemic response that provided a lifeline.

All in all, financially, I'm probably now breaking even on what I would've earned just doing hourly consulting for clients the last 5 years, vs starting the company.

But now we have a company with 12 people, a ton of great knowledge, and are on the path of growth. Hopefully this wasn't for naught!

You either have to save up for a year's worth of expenses and also downgrade the lifestyle and make sacrifices or convince a VC and raise a decent seed round but that too will come with conditions and you will probably not be able to pay yourself your market salary.

Entrepreneurship is hard. Very hard. Survivorship bias ensures that we only hear about successful ones where everything worked out. But as you already know, that happens in a tiny number of cases and that too after a lot of hardships.

Starting up something as a side hustle is the only viable option. You will have to put in after work hours and sacrifice some family time to fulfill your dream if you don't want to upset your marriage and lifestyle.

If you have a single income stream with a lot of dependencies, it's extremely risky to even distract yourself with wishful startup ideas. The most useful advice would be to get your life/money/time in order first. The worst thing that could happen to a side project is when wife/kids/bills start complaining nonstop for attention!

Google has a 20% rule which could work for those who have managed to find clean time gaps in weekly schedule to work on side projects. But never commit full-time to an idea or half baked product until it matches most of your previous income with an upside potential that truly requires your dedication. ie. don't quit your job until you can fully pay yourself from the new business!

The longer answer is that maintaining your current standard of living is not something you can do. You would need to make some sacrifices to get off the ground (roughly 18 months), even if you have a windfall of cash to take the time off you'd be sacrificing that windfall.

I have kids/wife/mortgages (plural), have started three companies, and worked in FAANG companies. I've never had a stellar exit but made some sustainable businesses. The cycle is basically feast and famine; 5 years at corporate job building up reserves and getting ideas, then 5 years of cutting back and getting a company off the ground. My wife doesn't really like the lean times, but she knows that is who I am (and dreams of big exits)

Another path is having a unique story that you can raise money on. A significantly sized problem that you are passionate about and have unique domain experience with. You can potentially acquire this unique experience via strategically picking where to work prior to starting the company. Such as taking a smaller salary specifically to get said experience.

The other path is just busting your ass working for someone else for awhile and building your war chest before going out on your own. Save up at least 1 year of living expenses.

For reference, I've done a blend of #1 and #3. Though in hindsight I wish I did more of #2. Having unique domain expertise gives you a competitive edge.

It is easy to start a startup in your 30s. In fact that is the only time you should start one. You finally have some life experiences to build a startup around.

By 30 you should have enough money saved to run for a year or two.

Your startup idea total addressable market should be clear. If it is close to a billion, go VC funded.

If it is in the 10s of millions to a few hundred, bootstrap.

Next, you have kids. You cannot faff around with company name, logo and such nonsense.

You need to focus on getting money in the door. So then where is your first customer? Hopefully with your 30 year of experience you have spotted someone already. Go to them and tell them that whatever they are looking for, your startup provides. Doesn't matter what they ask for, tell them yes it does that, the best in the industry. Take their money to book a spot as you are doing "revolving entries."

Do at least 5 of these. Tell them some nonsense about the price being a lot more but you are charging much less etc for them to be part of the existing cohort. This is important. Nobody wants to enter the train first. They want to be part of a journey where there are existing passengers.

Once you have money in your business account that is when you can start hiring someone to build a really scrappy version of your product. While all of this is happening make sure to always keep on getting new customers and getting money into the account. Business is about getting money into the business account. Never lose sight of that.

Now, you should have a huge dream about what your business can be. The larger the dream the better. If you can promise the moon and the stars and you have a total addressable market of about a $1 billion reach out to VCs, and ask for millions of dollars.

The larger amount you ask the more it'll seem to them that you have some special sauce. Once again make sure that you lie through your teeth because VCs don't understand anything and they're really easy to fool. Talk about changing the world and network meshes and AI and all those things. Get a good pitch deck designer.

Your only loyalty is to your customers and your problems space. Everybody else is a goose that needs to be squeezed. Once you reach your series B and Cs, losing is no longer an option. Make sure you sell secondaries and get at least $5 million in your personal bank account to derisk any future problems. From then on the world is your oyster.

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)

Mostly that is the way BUT not the only way. Have you saved any money to take this risk ? Can you work for say 12-18 months and not worry about paying bills if you quit your high paying job ? If yes, then by all means you should consider it. If you don't have anything saved and you don't live below your means, tough luck. You have to give up somewhere if this is important to you.

Another option is to use your money and buy a small project/business that has some cashflow coming in already. This may not be a hockey stick high growth startup but may be you don't need/want that ?

I imagine it could be done but you'd have to cut down your expenses to a minimum which in my opinion comes with too much of an opportunity cost. By which I mean missing out on experiences and fun things with the children. In 10 years time they'll be busy with friends or video games. At that point I could consider it again.

If I was really determined to make it work I'd aim towards contracting in a field you have experience in. If you have enough success with that you should hopefully be able to pay the bills from that and squeeze in work on your own thing between paid gigs.

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 dollar / year lifestyle business is incredibly simple (not easy, but simple). Starting a fifty billion dollar pharma company is incredible difficult. Anyone saying "well I want to start the latter, not the former!" has never had a 1 million / year lifestyle business.

Saying that I believe there are options:

1. Work out a concrete problem you're passionate about, then try to attract early capital (business angels) that allow you to draw a livable salary. 2. Join an early stage startup. There are still companies who raised seed in need of strong CTOs.The best founding teams are reluctant to give away equity and are happy to pay more instead. 3. Find structures like startup studios. Especially in the US there are a lot of studios that give you a viable idea and/or capital really early.

If you're in Europe feel free to reach out.

Alternatively, find a cushy corporate job with low expectations that is completely outside the domain of the company you want to build. Then, bring your personal laptop to work and work on your side project. Make sure your contract doesn’t give them rights to your outside projects. Make sure you use a separate network (e.g get a 5G hotspot). You might want to fake your commit times so it all looks like it happens during non business hours in case you are sued and audited.

I don't think you have to drink the hustle koolaid to succeed. I think individual output/hr. follows a power law distribution like most everything else. A lot of younger founders work crazy hours to overcome their lack of experience.

What's more important is your fitness to address the particular problem you choose to work on, the folks you team up with to do so, the timing relative to market needs, and the amount of time you can operate with little/no revenue. Having more work hours to dedicate can certainly help, but I've seen both people that overwork and people with ~normal schedules succeed.

If you want to found a money-burning VC-backed play for world domination, that’s probably not something you can do while you raise your kids and pay your mortgage.

However, if you’re interested in starting a business, providing a valuable product or service that people need and will pay for, you can absolutely do that.

The real answer I think you’re looking for is that you need to put a lot of money in savings, starting now, and you need to be aiming for actual paying customers on day one, not on convincing someone to give you a billion dollars to screw around until you find product market fit.

[0] https://www.indiehackers.com/podcasts

This is a conversation you should have with your spouse. Many spouses go back to school or pursue a financially risky entrepreneurial path. The other spouse supports the family. I've also seen this blow up, as the fiancee/spouse that supported the partner gets dumped after shortly after success... If you do this, I strongly encourage you to offer your spouse a generous postnuptial agreement (i.e. more than CA family law defaults to.)

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.

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.

now post-startup, i barely have time to keep things going at the level required to maintain excellence, while not neglecting my young family. lots of push/pull around work, and lots of arguments and frustration with my wife. i honestly couldn't imagine getting a new business off the ground right now, where you have to do everything.

Here are my tips. Do it on the side at first. You know those hours from 5am-7am when no one else is awake, you will be. You know those hours between 10pm and midnight? Same thing. You get a lunch break at work... you are now working on your side gig. You have plenty of time during the day to devote to something else.

Why do you want to do a start-up? To join the cool kids club and be a hu$tle-grind founder?

If you don't have the energy to start it as a side hustle and get the basics down why do you think you will hack it as a full-time founder?

You avoided saying why exactly you want to found a start up. In general you seen ignorant about what it actually takes to do a start up.

You have a family and responsibility. Don't you feel like your first priority should be providing them with security and prosperity?

My advice: get a hobby and don't fuck up your families life because you are bored.

1. Reduce expenses as much as you can.

2. Get your wife a paying job if that is possible.

3. Save enough to be able to live off the next 4 years without earning anything.

4. If 3. is not possible, then start something on the side.

5. If savings plus side income gives you runway for 4 years, then you are good to quit and focus fulltime.

6. Dont use your wife's savings to pay the bills. That is just fall back. If you are using up wife's savings/income, then it is right time to start looking for a job.

7. Consider moving into a more comfortable job, which gives you more free time for side hustle.

1. Set a monthly ad budget for your startup.

2. Run ads for your start up.

3. Change the credit card code so it puts a hold on their credit card and removes it. (You want to make sure your customers can actually afford your product)

4. Once the user signs up direct them to a page saying due to overwhelming demand you can't provide the service yet and let them know that their credit card has not been charged.

5. Once your startup is earning more than its ad budget, hire a developer to make it.

6. If you don't like this part of the business, absolutely do not start a startup.

- Save up for a 3 month runway, for example by freelancing on the side of your day job. - Do the startup on the side. Potentially dialling down you day job effort to 75%.

Most startups will benefit from a pilot/MVP stage, perhaps you can reach that stage working only evenings?

I suppose the real question is if you really need to maintain the same standard of living. If you have a well paid tech job you can probably survive not spending like someone making 250 k, at least for a few months.

I left very good paying job in 2008 ($400-$500k+) right after my first child was born to pursue startup life. To be honest, I had a romanticized notion of startups before going into it. In my defense, I was working at a very successful company that itself had been a runaway hit startup, and it sure looked easy while I was there. I never really thought about how many startups fail, never thought of how quickly you can burn through your savings with no income, and never really thought about the impacts on my family.

15 years later and multiple not-so-successful startups later I'm still grinding it out. Making enough that I can scratch out a living but still making a lot less than if I had stayed employed. Yes, each startup up that I've done has provided me with a lottery ticket with big upside potential, but no home runs yet. I do have a very interesting public profile that people like and respect, so I guess that's a cool kind of non-monetary currency. Current business I'm working now could be decent sized over time as a regular old business, but we shall see.

I will say that every day I'm wracked with guilt regarding whether I made the right decision to pursue the path that I'm on. I wonder whether I've harmed my wife and children and provided them with a less than stable future. I am saddened as a man that I not the provider that I want to be and I feel shame in the sense that I'm not providing as well as others do. I hate worrying about money and I hate thinking about what could have been if I stayed employed. These feelings have complicated my marriage, and while my wife still supports me, I often hear the disappointment in her voice when we talk about our finances.

My recommendation would be to do a start up only if "you can" or "you must". "You can" means that you have a lot of wealth laid up already, or you have a spouse who can carry the income burden alone and doesn't mind doing so. "You must" means you have no other options and you can't find another job or you're simply unemployable for some reason.

A boring, stable life is greatly under-appreciated and I think our society fetishes entrepreneurs to a fault.

If all you have is vague ambition and no openings/unique angles, 90% is too optimistic.

Your mileage may vary.

It's not sustainable indefinitely, and with the current funding environment you may not be able to raise money. Even after raising money the startup life will be all-consuming so spending extended time with wife and children is going to be next to impossible.

I've never seen any research on the topic but I have a strong suspicion that if you looked at the failure rate of startups founded by 20 years old it would be vastly higher than that of startups founded by 40 year olds, as 40 year olds are likely to be able to invest their own funds in the early stages, have industry expertise and contacts, and are more likely to have learned the interpersonal skills to manage relationships with co-founders, customers, funders etc. They also probably know the market that they are going into so have a much smaller space to search for product market fit than a 20 year old with less knowledge. There are exceptions of course.

But the honest reality is that if you don't have a year or two's cushion where you can continue to pay the bills while pursuing your startup you probably shouldn't do it if you have kids and a family, unless your partner is willing and able to pick up the slack financially. That's assuming you go for the classical silicon valley "let's dedicate every waking hour to building our tinder clone for chinchillas that will revolutionise fuzzball breeding" tech-bro method of working on a startup. It might be saner to take a slower approach and bootstrap to begin with while seeing if you can work part time.

[1] https://www.cnbc.com/2021/05/27/super-founders-median-age-of... [2] https://hbr.org/2018/07/research-the-average-age-of-a-succes... [3] https://www.statista.com/statistics/1220545/founder-age-star... [4] https://startups.co.uk/news/average-age-of-startup-founder/

I'd love to know how folks deal with this. We've used various health co-ops. Still not great. I feel like it's one of the biggest factors holding people back from starting a business.

Also partnering with existing projects.

Perhaps there is a start-up in the realm of helping people like yourself do what you want to do.

But you may want to ask yourself why. If it’s just that you are itching to gamble with your families financial future, perhaps back off.

If you feel you have an idea worth pursuing, go for it.

With some luck eventually you work out something at night times if you have the energy.

Skip TV. As soon as the kids are in bed go for it 2-4 hours, then watch a movie with your wife or have sex. Never forget: Happy wife happy life.

You don't. (Unless you have a substantial amount of personal savings to draw down.)

You take a hit in current income to do a startup. No one is going to pay you the same amount to try to find product-market-fit for yourself as someone else who will pay you to exploit already found PMF for them.

Remember: the failures are never spoken off, and successes become stuff of legends. Good luck.

Many factors come into play from your spouse to your cofounders and team. Your personal time management, organization skills, and support groups become even more critical.

There is no simple/single answer to your question, just like how to have a successful marriage or founder relationship, if you commit, you will find a way.

This is how I did it, but it still requires your wife to be on board. Ultimately it’s a lot of stress and if you can build a rewarding career working for successful companies you may just want to double-down on that.

In your 40's+, you're no longer staying up all night (probably), but statistics supposedly say that most successful businesses are started by those in their 40's.

The tradeoff is the absurd amount of equity you concede to the studios - who are in essence taking advantage of your financial situation - which ends up causing many serious issues down the road.

You don't.

Your kids are young for but a blink of an eye. Don't miss out on that.

When they're out of the house, _then_ start.

Disclaimer: I believe I was the only YC founder in my batch (s2010) who was married with kids.

If I had to give postive advice, I'd say negotiate with your family to carve out the time, starting with an entire month away then some kind of segmented regular time you are not disturbed.....

High risk startup with investors pressuring you to go big or go broke is not the only model.

Build a sustainable business, whether you do it full time or you do it on the side.

You don't need to pay yourself to work yet, just find more hours. Wakeup at 5 AM and do it before work.

You'll want her to be on board.

Kids either stay at home under your watch (depending on their age), or have your extended family watch them for a possibly below market compensation?

http://www.paulgraham.com/startupfunding.html

Scroll to the consulting section

Only quit once was making significantly more ($20k/mo) than my other job

Wife, mortgage, and newborn

Are you selling enough of a product/service that requires you to hire someone to work on it full time?

Get to that point before quitting your job.

(After working on a funded startup full-time as a cofounder.)

Coming sooner or later …

First, you need to have your spouse onboard. When I mean onboard, I mean she needs to understand that most of homelife is going to be shifted soley on her. I cannot stress this enough. This means kids birthdays, soccer practice, ..., you know the drill if you're a parent. There is almost a 100% chance you will end up divorced, during the process, or after at somepoint. Doing this is going to change you, and change your spouse. I cannot describe the amount of stress you're about to endure. If you're going home at 5pm, you're doing it wrong.

You need to define goals for your personal life, and for your business. They need to be detailed, and aligned. If you miss a major milestone, things just got that much harder.

Next, you need to have a product (at least a prototype). "looking for product-market-fit" is not how you go into this. You should have identified a problem others are having, and know the solution before you even start.

You need a business plan, it doesn't need to be formal. You need to know your burn rate, and what it will cost to get you to the next steps, which is to find an angel or other investor, or revenue stream that funds you, and then to productization, and whatever your exit strategy is going to be. Remember above goals.

I contracted my engineers out to help fund our main product line, after I had my first contract in place, and then was able to bring on investors. Find people with investments in oil & gas. They have tons of cash, and they don't mind losing it. Having the revenue stream helps potential investors. You learn why.

Depending on your product/service, you're going to need a customer. This is the really hard part. You need to find someone that needs your product, that is willing to go through the trials and tribulations with you.

Hire an attorney, or at least find one that will work with you. If your product interrupts the market in anyway, be prepared for lawsuits. I had two lawsuits that I won both. It cost me a portion of the company. I had no way to pay them.

Do not give equity out. Equity is worthless until it is not. Beware of the wolves, and sharks. Wolves want to be part of your pack, and feed on your winnings from the inside. Sharks are looking for a quick buck. They are easier to spot. Only work with people that can contribute.

The single best advice I received was from the president of Challenger Capital. He told me this, "Go for the throat, because if you don't, they will." That was the only piece of advise he was able to give me, and it turned out to be the best advise I could have received.

Your first startup will be the hardest.

I started my first company with $2400 dollars in my checking account, a pregnant wife, a mortgage, and very little debt. Six months after the aquisition, my wife filed for divorce, and then tried to take it all.

If I am really honest, looking back; I don't know if I would do it again.

* Already be wealthy, or at least well off.

* Be able to live of spouse's income.

* Live off your parents' money.

The whole experience was the hardest thing I've ever done.

It was also one of the most fulfilling professional experiences of my life.

I intentionally stepped off the corporate ladder to pursue this dream. But because of my prior commitments/obligations, I wasn't able to drop everything and go all in. That was a hinderance. It made things harder. It put a strain on my family. But it was doable. And even though we didn't achieve our ultimate goal, these complications were not the reason for failure.

I became an independent consultant that gave me an income with some flexibility to allow me to asynchronously lead our startup. I called the time outside of my consulting work "the nightshift". We raised a seed round that allowed my younger and less encumbered co-founders to work as FTEs. We took in more funds that added another six FTEs and an offshore team. Over the 10 years we existed, I never took a salary. When the chips were down and I needed to be 100% dedicated, I emptied my retirement account.

This arrangement was far from ideal, nor do I fully recommend it, but it gave us a shot. We built, tested, and learned our way to a product that served several million (non-paying) customers. We made plenty of mistakes. But we learned from them. We learned to be so frugal, so resilient. So incredibly nimble and innovative. I yearn for that kind of creative power again. It has prepared me to take on anything in life. I've never been to war or faced death with my comrades on a daily basis, but in business terms, I imagine startup life is as close as you can get. The experience has made me a better husband, father, friend, and colleague.

I've since returned to corporate life (for now). There I am invincible. None of it scares me. Corporate politics, bureaucracy, and general bullshit pale by comparison. My startup experience has become my superpower. Because I know I can help raise our game, knowing how to bring out the best in our people and to keep perspective on what is truly "hard" and how to get things done with less and under far less ideal circumstances.

So I say go for it. But go in with your eyes open. The odds are long no matter what. Might as well take your shot. At the very least you'll learn a lot. And someone with your talent, as long as you continue to hustle, rarely go hungry in this world. And if you succeed, well then, you might get a book deal in the process.

by a motorbike, learn golf, acquire a language, - but don’t bet your family on your personal dreams.

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!!

If you’ve been at the company long enough ask if you can take a 6 month sabbatical, that should give you enough time to test out if the idea is feasible.