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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 b

by earino 4y ago

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 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.

generalizations 4y ago
> 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. Then figure you have 10-20 active years left, and do you really want to spend 5-10 of them on a startup?
- n4r9 4y ago
  A lot of people do! The average age of a successful startup founder in 2020 was 45: https://economica.org.uk/research-the-average-age-of-a-successful-startup-founder-is-45/ https://economica.org.uk/research-the-average-age-of-a-succe...
  - lazide 4y ago
    Successful != typical, or even average in this context when referring to folks that start. If you’re looking at starting, it’s helpful, but it’s important to not delude ourselves either. Having more life experience helps, but when the funnel has a > 90% overall attrition rate, it’s still far from a sure bet. Part of the reason why the older folks tend to do better IMO, is it’s more likely at that age that they know their own capabilities better and are less likely to launch down a path they’ll definitely not succeed on, and the numbers reflect that more. It doesn’t mean automatically everyone once they hit that age will have those odds. There is a lot of self-selection bias going on.
    - n4r9 4y ago
      Possibly some but not that much. The linked research states that the age is still up at 42 when you remove "successful", and still 40 if you then add "software".
      - lazide 4y ago
        Interesting, thanks for the correction. Apologies for not RTFM’ng first.
- earino 4y ago
  I'm not sure I understand. But I think my answer is, "yes, I would!" By that point, hopefully I have enough self knowledge to understand what motivates me and what my true competitive advantages are. I also hopefully have a strong network I can leverage to help me with any blind spots I may still carry. And to spend 5-10 years working on something that I truly am passionate about, which I've worked hard to have the resources to do without encumbering others, sounds rather nice!
- aynyc 4y ago
  For some people, spending 5-10 years on their dreams in their 50s is totally worth it.
- __derek__ 4y ago
  This underestimates longevity a bit: a 55-year-old in the US has a life expectancy of ~26-29 years (male and female, respectively).[1] Granted, this may hinge on what you mean by "active" years. [1]: https://www.ssa.gov/oact/STATS/table4c6.html https://www.ssa.gov/oact/STATS/table4c6.html
- treespace8 4y ago
  As someone close to 50 in this boat it a great question. The fact is I wanted to build a startup to get rich. That's it really. Now that I am much more finically secure (but not rich by a long shot) I'm not sure I will want to roll the dice or just keep my job as an IC.
gofreddygo 4y ago
If only anyone knew what that one awesome startup was. Its the market that drives businesses. If I wait too long to even start trying, chances are slim that I ever will try, markets change you know On the other hand, if I wait, building a business off the network and skills and reputation and market knowledge I've built, has a higher chance of survival. My philosophy is to be non-dogmatic but probabilistic and opportunistic. If you see an opportunity, try it out, take a loss maybe, and learn and try again. Like a good gamble, you need to spend most of the time at the table, in the game before betting big, not working in the shop next door waiting to get in.
Ancalagon 4y ago
I agree with the premise of this, but want to point out a normal job doesn’t necessarily lead to fulfilling those responsibilities adequately even though maybe they should. People still get stressed, overwork, have ambition, dislike home life, etc. I think OP should talk with his wife and make a decision based on milestones
- earino 4y ago
  I agree with you on both points: 1. If it's a bad job that pays well but makes you miserable, that's a different situation. I assumed that was not the case but I may have been hasty. 2. No matter what, discussing with your partner is absolutely the right thing. But really discussing and coming together to try to come to a shared understanding. You never know, their tolerance for risk may be even higher than yours!
julianlam 4y ago
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.
- j45 4y ago
  Lots of indie hackers defeat blind luck and exit as much as the small percentage founders receive in a funded startup. Lots of good reading out there
  - paulryanrogers 4y ago
    Right it's a lottery, with very expensive tickets. You may have to pay with years of your life for each one, possibly significant others.
    - j45 4y ago
      Not if you consult and find the business needs and only build wher people want and are willing to pay for. Hitting the startup funding lottery to go on an expedition to find and build something people want is a different matter and maybe what you’re referring to, and if so, I totally agree with.
      - paulryanrogers 4y ago
        > Not if you consult and find the business needs and only build wher people want and are willing to pay for. That's only one part of the challenge. Market research is vital, yet alone is a not guaranteed success. Even if a valuable untapped market is discovered, there's more to success than just building a solution. Sales and marketing have to execute well too. A competitor from an adjacent industry could swoop in. Etc.
- cjohnson318 4y ago
  Alternatively, maybe your dad owns an emerald mine? Always an option!
dangus 4y ago
I disagree with your advice, because it amounts to "sit around and do nothing, give up on your goals." I know someone who has a family who stated a side business in their spare time in their 30's. It started extremely modestly using just some spare time, and I think a lot of people have at least some spare time. The average person spends, what, 4 hours a day watching TV? If OP has an hour a day they can make at least some progress. This person also uses freelancers to help achieve chunks of work where they aren't experts. A modest amount of savings can pay for some of these deliverables. I know someone else who sells baked goods at farmers markets. They put some time into baking and posting to social media but it's a side gig. Another person I know got together with a group to help share the effort and they're working on a hummus business (again, selling at farmers markets). These are all people with families and day jobs. Instead of that fatalist do-nothing advice of "wait until you're an empty nester," I'd say "start small." Don't expect to be a massively scaling SaaS thing. Don't expect to replace your income, certainly not within ~5 years. Don't try to build some wildly complicated product. Budget your time, don't neglect your personal life. Focus on solving a simple pain point for a specific type of customer. The other thing I'd warn OP about: don't start a business for the wrong reason. The wrong reason is dreaming of a lottery ticket out of wage slavery. The right reason is that you've identified an area that you think has potential to help someone else achieve a positive outcome, especially an area where you have some kind of expertise.
- earino 4y ago
  I agree with a lot of the sentiment of your comment, particularly about introspecting and understanding what your reason for doing a startup is. I think that's very good advice. However I don't feel that "being a solid professional making a solid wage, and be a good parent and partner" amounts to "sit around and do nothing, give up on your goals." I feel like the advice I gave is "wait until the time is right", which is different from fatalist nothing-doing!
  - dangus 4y ago
    I still think your original comment was way closer to "don't bother trying " than that.
Xcelerate 4y ago
> You signed up for a bunch of responsibilities. You are always going to be your kids parent. You are only going to have this one opportunity to get this marriage and this family right. I think this is a bit of a depressing take. Even committed parents and spouses take alone time for themselves and have hobbies. Just treat your side project as your hobby and you can still have a healthy family. Also, think about how much time the average person wastes day-to-day. Total up all the time watching television, reading articles, browsing online. Outsource your chores and improve the efficiency of your day job (e.g., work remotely to eliminate a commute) and you'll have plenty of time left over for a side project. You might say — how can a side project be successful on 5 hours a day in the early morning? — but consider that someone pursuing a startup for 10 hours a day isn't going to have a significantly higher probability of success relative to other factors that make a larger difference (ability to interact well with other people, product-market fit, etc.) Sure, you might reduce your probability of success a bit, but you are essentially buying a lottery ticket anyway when you decide to start your own company, so would it really bother you much if your already small odds of success are 60% of what they would have been if you committed to the startup full-time?
- earino 4y ago
  I actually agree with a lot here. If the question had been "how can I have a fulfilling hobby while also working full time", i think I'd agree with a lot of the advice you gave. It's very good advice about time boxing, having realistic goals, and looking for a well rounded life. Having hobbies is something that can be really rewarding, and hobbies can be many kinds of things, from deeply technical to purely relational and social. However, I will admit my bias here, the OP explicitly talked about "a startup", and I don't believe I know of too many hobbies that allowed someone to replace their income and retain their standard of living. The people I know who have done this have, regularly, done so with significant risk, commitment, and single-mindedness of purpose. I'm sure there are exceptions as those you listed, but I personally haven't experienced them.
- saulpw 4y ago
  > Even committed parents and spouses take alone time for themselves and have hobbies. The parents I know with kids younger than 7 have no time for themselves or their hobbies. They're lucky if they can scrape together a few hours a week for basic self-care. In the mornings the kids demand full attention and after the kids go to bed there's maybe time for a single TV show which one person falls asleep during. > how can a side project be successful on 5 hours a day in the early morning? So from 4am-9am a person is grinding away on their side project or startup while their spouse takes care of getting their kids ready. And then at 9am they just slide right into work for a cool 8 hours, eating lunch at their desk and then checking out at 5pm for a nice family dinner. This sounds like a robot's advice to a human to how to organize their life. Completely not feasibly and devoid of lived experience.
codazoda 4y ago
I also took this path and have yet to really succeed. I am now 45 and an empty nester. I wrote about some of my failed businesses in this blog post titled, "How to Lose Money with 25-Years of Failed Businesses". https://joeldare.com/how-to-lose-money-with-25-years-of-failed-businesses https://joeldare.com/how-to-lose-money-with-25-years-of-fail...
QuarterReptile 4y ago
My situation isn't quite the same, but it is leaving a well paid job when I have two kids and a mortgage in order to work in some to-be-determined field where I have no experience, with no opportunity (after a short window) to return to my former field if I change my mind. First, have some savings and a plan to minimize burn rate if things get tough. More importantly, there needs to be a compelling answer to what you're accomplishing for your family, or what you as a family are accomplishing, by making the change away from your present comfortable arrangement.
synergy20 4y ago
totally agree, you just DONT I sold mine and waited 10+ years until kids are in the last two years of high schools, I also saved a bit during these years so I have some cushion to restart my startup dream. Maybe it's why there are a group of entrepreneurs in their late 40s and early 50s just like what I had?
passwordoops 4y ago
The upside to waiting is also gaining experience. There's something to be said to learning in environments that work before taking a stab yourself. I'm sure many founders over 40 avoid many mistakes this way
onlyrealcuzzo 4y ago
> My very concrete feelings on this is that you probably don't. The ones that do - and usually the few in this age group that succeed - are already independently wealthy from a combination of having a highly successful career and making good investments. People that have $1M+ to fall back on - and can easily land another job making $400k+ - if things don't work out. You don't see too many 35 year-olds with 3 kids and no savings starting Ubers. Every once in a while you find an Elon Musk who already had plenty of money, and decided to start another business. People with insignificant amounts of savings starting successful companies are almost exclusively in their teens or 20s.
- lazide 4y ago
  Well, you definitely don’t see any smart ones doing that, and for good reasons. Is it impossible with a stressful job, a bunch of kids, etc. and not being independently wealthy to do it? Not necessarily, I guess? It is definitely not a good idea, however, and it’s highly likely to implode one of those other areas of their life. And frankly, it isn’t a good idea for the vast majority of independently wealthy folks either. The types of pressure and lack of structure in the environment can and does mess with peoples minds, and can encourage them to end up a lot less wealthy at the end. If they’re particularly unlucky or mess up, even with expensive legal issues following them around.
la64710 4y ago
Only problem is when you are 50s you are likely to have the time and money but not the energy. Surely it is not the case with everyone but enough to have this cliche pass around for quite some time.
- lazide 4y ago
  And that is why it is rare that it happens. Which is fine, it’s not a ride many people would even want once they have the rest of their life stabilized.
- mistrial9 4y ago
  > you are 50s you are likely to have the time and money but not the energy who do you think initiated these "startup" patterns post-2000 ? It was boomer+ investors using vast investment pool money, in the last 20 years.. now they are dying off and it is on auto-play via "don't get creative" money builders.
j45 4y ago
I’m curious, do you have kids? My perspective changed when I had kids. And I had kids close together, Matter than friends to boot. Mostly I realized how’s much time I was wasting to that point in life and I stopped. It’s perfectly possible to do a startup at any age. Know many people who do and have. Kids were a perfect prioritization and decision aid in my case. It makes you perfectly serious about doing what needs to be done. Innovation can happen just fine with constraints. Leading up to it if you don’t have good adult habits and skills you probably some be a lasting successful entrepreneur anyways. Doing a startup is a lot like being responsible for a baby. Some things need to be done whether you like them or not. Status aren’t just about working on the fun parts. Getting it right also means making sure you are the kind of example you want to be for them to take their own shots. Sacrificing parents can better a sense of sacrifice in kids and it might be a cycle someone is looking to break. Would there be more time before kids? Sure. But hard to find people in their 20s a made the most of their time beyond chasing every shiny thing. Generally our standards for how we spend our time are lost in our 20s and improves as we become more well rounded. You only start getting good and dangerous in your 30s and 40s. It’s why so many vcs are older, they buy the years of young people and are ok if it goes no where. If you don’t want to be a statistic, you can look at bootstrapping smaller and then growing. There are funds like tinyseed and others that specialize in it. In your CV 30s you probably have insight in an industry need that you could bang out and have making money per easily to transfer to the next thing. HN might not be the place for this kind of thought especially if it’s orthogonal to the vc echo chamber that attracts a following and needs a decade to see in balance with other options. If success is freedom of time, attention and resources where you want to put them, the path of startups as you are implying (likely funded) might not be compatible with you. Todays the youngest you’ll ever be. If not now, then when?
- earino 4y ago
  I do, thanks for asking! I am the proud dad of a 22 year old son :-) I definitely agree that having a child can be a spectacular forcing function for focus for some. I unfortunately also know folks for whom having a child was the proverbial straw, and whose life fell apart afterwards. I was running my own company (RFID and industrial automation startup) before him. When I became a dad I found a corporate job. The worry around healthcare costs for a family as an independent were simply too much for me, even back then. All in all, I feel very fortunate in how it all worked out for my family.
newone2three 4y ago
Disagree. Not every startup has to be a massive success, not every founder needs to be a billionaire, and not everyone has to work like Elon Musk - you’re probably not sending rockets to Mars. OP might be very happy with a company with no employees that makes 200k a year. To the OP: save up for 6 months of working on your own thing, OR, launch loads of little experiment MVPs that don’t need lots of work to get _something_ out quickly.
golemiprague 4y ago
toomuchtodo 4y ago
Thanks for writing this comment. It is actionable, excellent advice.
jollofricepeas 4y ago
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 you’ll need to be STRATEGIC. A couple of personal tips for bootstrapping… 1. Communicate and commit to joint goal setting with your family. What are you all working towards together and why? None of us build companies alone. 2. Make your day job your first customer and biggest supporter. If you can’t then join an organization that is not threatened by entrepreneurship. 3. Identify a family friendly business model that you can test with minimal effort. I’ve always started my own businesses with my own money (Seed ~100k USD). My largest business does high seven figures and I started it with ~25k USD. This means getting in bed with a customer(s) early and charging upfront. Again see (2). 4. Set reasonable timelines for yourself. While your LinkedIn feed has friends pumping out VC propaganda remind yourself that you’re focused on actually building a sustainable business so take your time where you can. This might mean working with your wife to create a schedule for yourself where you work on the business TOGETHER a couple of hours every evening and weekends. When you bootstrap, you decide your own timeline. 5. Pivot and budget. Sometimes it’s not going to work so be prepared to put your business on autopilot (if stable), rework it or just kill it early. Cattle not pets. Businesses are tools; nothing more. 6. You will have to sacrifice something so work with your family to know what those things will be… less going out with friends, less TV/gaming/music festivals, less vacations, less spending, etc (See #1) Best of luck
- ip26 4y ago
  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.

by earino 4y ago

generalizations 4y ago

> 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. Then figure you have 10-20 active years left, and do you really want to spend 5-10 of them on a startup?

n4r9 4y ago
A lot of people do! The average age of a successful startup founder in 2020 was 45: https://economica.org.uk/research-the-average-age-of-a-successful-startup-founder-is-45/ https://economica.org.uk/research-the-average-age-of-a-succe...
- lazide 4y ago
  Successful != typical, or even average in this context when referring to folks that start. If you’re looking at starting, it’s helpful, but it’s important to not delude ourselves either. Having more life experience helps, but when the funnel has a > 90% overall attrition rate, it’s still far from a sure bet. Part of the reason why the older folks tend to do better IMO, is it’s more likely at that age that they know their own capabilities better and are less likely to launch down a path they’ll definitely not succeed on, and the numbers reflect that more. It doesn’t mean automatically everyone once they hit that age will have those odds. There is a lot of self-selection bias going on.
  - n4r9 4y ago
    Possibly some but not that much. The linked research states that the age is still up at 42 when you remove "successful", and still 40 if you then add "software".
    - lazide 4y ago
      Interesting, thanks for the correction. Apologies for not RTFM’ng first.
earino 4y ago
I'm not sure I understand. But I think my answer is, "yes, I would!" By that point, hopefully I have enough self knowledge to understand what motivates me and what my true competitive advantages are. I also hopefully have a strong network I can leverage to help me with any blind spots I may still carry. And to spend 5-10 years working on something that I truly am passionate about, which I've worked hard to have the resources to do without encumbering others, sounds rather nice!
aynyc 4y ago
For some people, spending 5-10 years on their dreams in their 50s is totally worth it.
__derek__ 4y ago
This underestimates longevity a bit: a 55-year-old in the US has a life expectancy of ~26-29 years (male and female, respectively).[1] Granted, this may hinge on what you mean by "active" years. [1]: https://www.ssa.gov/oact/STATS/table4c6.html https://www.ssa.gov/oact/STATS/table4c6.html
treespace8 4y ago
As someone close to 50 in this boat it a great question. The fact is I wanted to build a startup to get rich. That's it really. Now that I am much more finically secure (but not rich by a long shot) I'm not sure I will want to roll the dice or just keep my job as an IC.

gofreddygo 4y ago

If only anyone knew what that one awesome startup was. Its the market that drives businesses. If I wait too long to even start trying, chances are slim that I ever will try, markets change you know On the other hand, if I wait, building a business off the network and skills and reputation and market knowledge I've built, has a higher chance of survival. My philosophy is to be non-dogmatic but probabilistic and opportunistic. If you see an opportunity, try it out, take a loss maybe, and learn and try again. Like a good gamble, you need to spend most of the time at the table, in the game before betting big, not working in the shop next door waiting to get in.

Ancalagon 4y ago

I agree with the premise of this, but want to point out a normal job doesn’t necessarily lead to fulfilling those responsibilities adequately even though maybe they should. People still get stressed, overwork, have ambition, dislike home life, etc. I think OP should talk with his wife and make a decision based on milestones

earino 4y ago
I agree with you on both points: 1. If it's a bad job that pays well but makes you miserable, that's a different situation. I assumed that was not the case but I may have been hasty. 2. No matter what, discussing with your partner is absolutely the right thing. But really discussing and coming together to try to come to a shared understanding. You never know, their tolerance for risk may be even higher than yours!

julianlam 4y ago

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.

j45 4y ago
Lots of indie hackers defeat blind luck and exit as much as the small percentage founders receive in a funded startup. Lots of good reading out there
- paulryanrogers 4y ago
  Right it's a lottery, with very expensive tickets. You may have to pay with years of your life for each one, possibly significant others.
  - j45 4y ago
    Not if you consult and find the business needs and only build wher people want and are willing to pay for. Hitting the startup funding lottery to go on an expedition to find and build something people want is a different matter and maybe what you’re referring to, and if so, I totally agree with.
    - paulryanrogers 4y ago
      > Not if you consult and find the business needs and only build wher people want and are willing to pay for. That's only one part of the challenge. Market research is vital, yet alone is a not guaranteed success. Even if a valuable untapped market is discovered, there's more to success than just building a solution. Sales and marketing have to execute well too. A competitor from an adjacent industry could swoop in. Etc.
cjohnson318 4y ago
Alternatively, maybe your dad owns an emerald mine? Always an option!

dangus 4y ago

I disagree with your advice, because it amounts to "sit around and do nothing, give up on your goals." I know someone who has a family who stated a side business in their spare time in their 30's. It started extremely modestly using just some spare time, and I think a lot of people have at least some spare time. The average person spends, what, 4 hours a day watching TV? If OP has an hour a day they can make at least some progress. This person also uses freelancers to help achieve chunks of work where they aren't experts. A modest amount of savings can pay for some of these deliverables. I know someone else who sells baked goods at farmers markets. They put some time into baking and posting to social media but it's a side gig. Another person I know got together with a group to help share the effort and they're working on a hummus business (again, selling at farmers markets). These are all people with families and day jobs. Instead of that fatalist do-nothing advice of "wait until you're an empty nester," I'd say "start small." Don't expect to be a massively scaling SaaS thing. Don't expect to replace your income, certainly not within ~5 years. Don't try to build some wildly complicated product. Budget your time, don't neglect your personal life. Focus on solving a simple pain point for a specific type of customer. The other thing I'd warn OP about: don't start a business for the wrong reason. The wrong reason is dreaming of a lottery ticket out of wage slavery. The right reason is that you've identified an area that you think has potential to help someone else achieve a positive outcome, especially an area where you have some kind of expertise.

earino 4y ago
I agree with a lot of the sentiment of your comment, particularly about introspecting and understanding what your reason for doing a startup is. I think that's very good advice. However I don't feel that "being a solid professional making a solid wage, and be a good parent and partner" amounts to "sit around and do nothing, give up on your goals." I feel like the advice I gave is "wait until the time is right", which is different from fatalist nothing-doing!
- dangus 4y ago
  I still think your original comment was way closer to "don't bother trying " than that.

Xcelerate 4y ago

> You signed up for a bunch of responsibilities. You are always going to be your kids parent. You are only going to have this one opportunity to get this marriage and this family right. I think this is a bit of a depressing take. Even committed parents and spouses take alone time for themselves and have hobbies. Just treat your side project as your hobby and you can still have a healthy family. Also, think about how much time the average person wastes day-to-day. Total up all the time watching television, reading articles, browsing online. Outsource your chores and improve the efficiency of your day job (e.g., work remotely to eliminate a commute) and you'll have plenty of time left over for a side project. You might say — how can a side project be successful on 5 hours a day in the early morning? — but consider that someone pursuing a startup for 10 hours a day isn't going to have a significantly higher probability of success relative to other factors that make a larger difference (ability to interact well with other people, product-market fit, etc.) Sure, you might reduce your probability of success a bit, but you are essentially buying a lottery ticket anyway when you decide to start your own company, so would it really bother you much if your already small odds of success are 60% of what they would have been if you committed to the startup full-time?

earino 4y ago
I actually agree with a lot here. If the question had been "how can I have a fulfilling hobby while also working full time", i think I'd agree with a lot of the advice you gave. It's very good advice about time boxing, having realistic goals, and looking for a well rounded life. Having hobbies is something that can be really rewarding, and hobbies can be many kinds of things, from deeply technical to purely relational and social. However, I will admit my bias here, the OP explicitly talked about "a startup", and I don't believe I know of too many hobbies that allowed someone to replace their income and retain their standard of living. The people I know who have done this have, regularly, done so with significant risk, commitment, and single-mindedness of purpose. I'm sure there are exceptions as those you listed, but I personally haven't experienced them.
saulpw 4y ago
> Even committed parents and spouses take alone time for themselves and have hobbies. The parents I know with kids younger than 7 have no time for themselves or their hobbies. They're lucky if they can scrape together a few hours a week for basic self-care. In the mornings the kids demand full attention and after the kids go to bed there's maybe time for a single TV show which one person falls asleep during. > how can a side project be successful on 5 hours a day in the early morning? So from 4am-9am a person is grinding away on their side project or startup while their spouse takes care of getting their kids ready. And then at 9am they just slide right into work for a cool 8 hours, eating lunch at their desk and then checking out at 5pm for a nice family dinner. This sounds like a robot's advice to a human to how to organize their life. Completely not feasibly and devoid of lived experience.

codazoda 4y ago

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

QuarterReptile 4y ago

My situation isn't quite the same, but it is leaving a well paid job when I have two kids and a mortgage in order to work in some to-be-determined field where I have no experience, with no opportunity (after a short window) to return to my former field if I change my mind. First, have some savings and a plan to minimize burn rate if things get tough. More importantly, there needs to be a compelling answer to what you're accomplishing for your family, or what you as a family are accomplishing, by making the change away from your present comfortable arrangement.

synergy20 4y ago

totally agree, you just DONT I sold mine and waited 10+ years until kids are in the last two years of high schools, I also saved a bit during these years so I have some cushion to restart my startup dream. Maybe it's why there are a group of entrepreneurs in their late 40s and early 50s just like what I had?

passwordoops 4y ago

The upside to waiting is also gaining experience. There's something to be said to learning in environments that work before taking a stab yourself. I'm sure many founders over 40 avoid many mistakes this way

onlyrealcuzzo 4y ago

> My very concrete feelings on this is that you probably don't. The ones that do - and usually the few in this age group that succeed - are already independently wealthy from a combination of having a highly successful career and making good investments. People that have $1M+ to fall back on - and can easily land another job making $400k+ - if things don't work out. You don't see too many 35 year-olds with 3 kids and no savings starting Ubers. Every once in a while you find an Elon Musk who already had plenty of money, and decided to start another business. People with insignificant amounts of savings starting successful companies are almost exclusively in their teens or 20s.

lazide 4y ago
Well, you definitely don’t see any smart ones doing that, and for good reasons. Is it impossible with a stressful job, a bunch of kids, etc. and not being independently wealthy to do it? Not necessarily, I guess? It is definitely not a good idea, however, and it’s highly likely to implode one of those other areas of their life. And frankly, it isn’t a good idea for the vast majority of independently wealthy folks either. The types of pressure and lack of structure in the environment can and does mess with peoples minds, and can encourage them to end up a lot less wealthy at the end. If they’re particularly unlucky or mess up, even with expensive legal issues following them around.

la64710 4y ago

Only problem is when you are 50s you are likely to have the time and money but not the energy. Surely it is not the case with everyone but enough to have this cliche pass around for quite some time.

lazide 4y ago
And that is why it is rare that it happens. Which is fine, it’s not a ride many people would even want once they have the rest of their life stabilized.
mistrial9 4y ago
> you are 50s you are likely to have the time and money but not the energy who do you think initiated these "startup" patterns post-2000 ? It was boomer+ investors using vast investment pool money, in the last 20 years.. now they are dying off and it is on auto-play via "don't get creative" money builders.

j45 4y ago

I’m curious, do you have kids? My perspective changed when I had kids. And I had kids close together, Matter than friends to boot. Mostly I realized how’s much time I was wasting to that point in life and I stopped. It’s perfectly possible to do a startup at any age. Know many people who do and have. Kids were a perfect prioritization and decision aid in my case. It makes you perfectly serious about doing what needs to be done. Innovation can happen just fine with constraints. Leading up to it if you don’t have good adult habits and skills you probably some be a lasting successful entrepreneur anyways. Doing a startup is a lot like being responsible for a baby. Some things need to be done whether you like them or not. Status aren’t just about working on the fun parts. Getting it right also means making sure you are the kind of example you want to be for them to take their own shots. Sacrificing parents can better a sense of sacrifice in kids and it might be a cycle someone is looking to break. Would there be more time before kids? Sure. But hard to find people in their 20s a made the most of their time beyond chasing every shiny thing. Generally our standards for how we spend our time are lost in our 20s and improves as we become more well rounded. You only start getting good and dangerous in your 30s and 40s. It’s why so many vcs are older, they buy the years of young people and are ok if it goes no where. If you don’t want to be a statistic, you can look at bootstrapping smaller and then growing. There are funds like tinyseed and others that specialize in it. In your CV 30s you probably have insight in an industry need that you could bang out and have making money per easily to transfer to the next thing. HN might not be the place for this kind of thought especially if it’s orthogonal to the vc echo chamber that attracts a following and needs a decade to see in balance with other options. If success is freedom of time, attention and resources where you want to put them, the path of startups as you are implying (likely funded) might not be compatible with you. Todays the youngest you’ll ever be. If not now, then when?

earino 4y ago
I do, thanks for asking! I am the proud dad of a 22 year old son :-) I definitely agree that having a child can be a spectacular forcing function for focus for some. I unfortunately also know folks for whom having a child was the proverbial straw, and whose life fell apart afterwards. I was running my own company (RFID and industrial automation startup) before him. When I became a dad I found a corporate job. The worry around healthcare costs for a family as an independent were simply too much for me, even back then. All in all, I feel very fortunate in how it all worked out for my family.

newone2three 4y ago

Disagree. Not every startup has to be a massive success, not every founder needs to be a billionaire, and not everyone has to work like Elon Musk - you’re probably not sending rockets to Mars. OP might be very happy with a company with no employees that makes 200k a year. To the OP: save up for 6 months of working on your own thing, OR, launch loads of little experiment MVPs that don’t need lots of work to get _something_ out quickly.

golemiprague 4y ago

toomuchtodo 4y ago

Thanks for writing this comment. It is actionable, excellent advice.

jollofricepeas 4y ago

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 you’ll need to be STRATEGIC. A couple of personal tips for bootstrapping… 1. Communicate and commit to joint goal setting with your family. What are you all working towards together and why? None of us build companies alone. 2. Make your day job your first customer and biggest supporter. If you can’t then join an organization that is not threatened by entrepreneurship. 3. Identify a family friendly business model that you can test with minimal effort. I’ve always started my own businesses with my own money (Seed ~100k USD). My largest business does high seven figures and I started it with ~25k USD. This means getting in bed with a customer(s) early and charging upfront. Again see (2). 4. Set reasonable timelines for yourself. While your LinkedIn feed has friends pumping out VC propaganda remind yourself that you’re focused on actually building a sustainable business so take your time where you can. This might mean working with your wife to create a schedule for yourself where you work on the business TOGETHER a couple of hours every evening and weekends. When you bootstrap, you decide your own timeline. 5. Pivot and budget. Sometimes it’s not going to work so be prepared to put your business on autopilot (if stable), rework it or just kill it early. Cattle not pets. Businesses are tools; nothing more. 6. You will have to sacrifice something so work with your family to know what those things will be… less going out with friends, less TV/gaming/music festivals, less vacations, less spending, etc (See #1) Best of luck

ip26 4y ago
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.