I should have qualified my statement about failures better.

Current one: Financially successful for me.

Another one: Financially successful but got screwed over.

Another one: Was very successful with adoption, but timing got wrong and didn't become financially successful.

2 others: Moderate success but financially not successful.

It was really tough, but I enjoyed the process. I love building products. I have a few really good ideas, but don't have bandwidth for them right now. I would keep building products for my love of it.

My long term goal is to leave the world a better place. It took 10+ years to get to the point that I can work on anything I want to without worrying about bills.

I regret delaying having kids. I regret not spending enough time with family and friends. I wish I had taken better care of my health. But right now I get to spend more time with my kids than any of my friends.

Every individual is different with their situation and motivations. What worked for me might not work for others. The thing which helped me the most was my innate desire to build better products and making sure I keep learning more and more.

My life's driving principle is: If I can't look back at my self 2 years back and I don't think I was so stupid back then I am not learning fast enough.

Even though I have regrets, I would say it was worth it. Of course if I could I wish few things would have gone differently about my life - but who doesn't.

Also if you are looking to expand into new ideas and want eng folks with more time on their hands I have a group that would be interested. Currently we are evaluating ideas to go off and build after coming to terms with the big tech corporate grind.

I'm too early to yet have regrets about pursuing this path, but I feel like it will inevitably get to me too and I try to think of ways I could have the cake and eat it too ( to some minimal extent). I don't yet think about family, it's not on my priority list at the moment (I'm thinking about starting it in my 40s and I accept the drawbacks), but there are some things I would like to get out of my personal life - preferably while still in my 20s, rather than 30s that I care about.

I'm sorry because this is going to be a long post. Please feel free to ignore it. I hope it contributes something to the discussion in general.

I'm thinking about 3 scenarios I could play out:

A) Pursue a niche desktop app idea that is a spin-off from an earlier failed product. It's the scratch your own itch thing, I have a new vision for the product. It would take 1 year to ship and 2 years from now in total to evaluate. Potential 100k - 1M / year revenue after years in business. This could be the type of business I could work hard at now, and spend a healthy 50h/week later to be still able to enjoy my life and enjoy playing the game. It's also realistic given my current resources. If it fails, I "lose" 2 years.

B) Pursue another spin-off idea, but this one is not niche, it's big and I know I may come off as naive - but I'm certain this is something that people will want. The challenge here is more in execution and competition (there's no other product like this on the market, and the demand is there). I'm a little guy now, so I could get squashed by more experienced players however, I may still pocket a million before going out of business. To get started with it, I would have to get a full time job asap (I have a dead end freelancing gig now), work 1 year and then live off savings. So it wouldn't see the light of day until at least 2024. This plan would also require 5+ years working at intense startup, sacrificing a lot - all these personal goals I care so much about.

c) Focus on the big idea, but delay it by 2 years to get some things off my personal bucket list. So I get full-time job by the end of 2021, 2022 - 2024 I focus mostly on personal life, while working and making savings (I may have 10h/week to spend on building the prototype / v1 - which is very very little, but over 3 years is always better than nothing). Then 2025, quit job, work 70h/week full-time on preparing the business, launch it in 2026 or 2027. If it fails, I still should have enough savings to pursue another idea. Or if someone beats me to market and there's no point, I can pursue another idea straight away. Yes, it's 5 years, so there are big chances someone gets there first, but even if they get there first, they wouldn't get like a mainstream market adoption in 5 years, so there would still be place for competition and different variants of the idea. The real danger here is that these 3 years of focus on personal life may throw me off the path, I may not be able to come back once I lose momentum, but I like to think I would have the discipline to do come back.

Currently I'm most inclined towards option C - it has some certainity about it. The business may fail, but there's a lot of certainity I will have logistics to pursue another idea. I can also get personal goals to some extent (unless the pandemic restrictions last too long). So it's potentially big reward, less sacrifice and risk.

I put some work into option A however, so it's hard to not think about it. Maybe it could be really good opportunity at having a lightweight business, that's also achievable given my current resources and experience. But it can still fail - and it's a subset of the bigger idea (as I mentioned earlier, both projects are spin off ideas from my first failed product).And if it fails, I can't work on the next business right away.

I guess I self-answered myself here. I'm only torn because if I want to go for option C, I had this plan to release A as open source and use it for my resume, I think it would help the job hunt a lot and allow me to negotiate a better salary, as well as flex product-building muscles. The logic for this, is I want a remote job, and while there are full time remote jobs offerrings within the niche I'm freelancing in - I think it may take me some 6 months to get a job like this - so I think, I could take this time to release the app as open source to 10x my resume and not leaving the job thing to luck.

So because I work on product A day to day, it's challenging to not view it as a business. It will be even more challenging when I complete it and willingly not give it a try to sell it (though I know selling it is like 5x more effort than building it, but still).

It would be helpful to get an outside view on these plans. Maybe each plan is dumb either way. The plan I had 3 years ago didn't pass reality test. I suppose it could be similar this time. What would you do? Try to have a shot at the simpler product and accepting a 2 year delay if it doesn't work out, or follow the long term plan and have a go at a much more ambitious product with a backup savings plan?

Go through Naval's podcast "How to get rich". Listen it once a month for 4 months. Make notes and see how his suggestions apply to you. Focus on the things that you disagree with and understand why do you disagree with them.

Now on to my feedback:

You are worrying too much about big competitors getting you out of business or idea already launched. Unless your product has a very small market, there is always opportunities for new players. Looks at the instant messaging space over the time we have had IRC, MSN, Yahoo Messenger, Google Chat, Skype, WhatsApp, Telegram, Signal, Slack and there will be a lot more.

If an idea doesn't work out, you don't lose 2 years. You would have learnt a lot through this time. You are investing in your learning and capabilities.

Think of startup as a series of sprints. You sprint, strategize, sprint, strategize.

So my high level suggestion would be:

Start building what you want to build right now. Don't wait.

Don't think about doing startup in binary terms. Figure out which product you want to build next and try to find whatever time to make progress on it. During this phase if you have to sort out personal things do that. If you need to take a job to support finances do it. These are things that you have to take care of along the way. There will always be news stuff when you have taken care of the personal and finance part. Don't lose focus on your startup and keep chugging along.

If you get a job, make sure you don't use company hardware to build it. Make sure that there are no clauses which make products developed on your personal time as company property.

Yes pretty much I'm all over the place. It would be simpler if I had a single goal and be able to sacrifice everything else, but I can't. These personal goals are very important and spending even just 2 years on that would be one of the best investments I could make for myself, so I have been bending over backwards trying to figure out how I can carve out that time, while still being on the path towards having a product business.

> You are worrying too much about big competitors getting you out of business or idea already launched. Unless your product has a very small market, there is always opportunities for new players. Looks at the instant messaging space over the time we have had IRC, MSN, Yahoo Messenger, Google Chat, Skype, WhatsApp, Telegram, Signal, Slack and there will be a lot more.

You are right. Even more so I shouldn't worry since I'm small and my criteria for success are relatively low and unlike a startup with vc funding I don't have to take over the world to be successful. So even if a large competitor would pop up, there may still be a place for a few million per year niche variant of the idea.

> Start building what you want to build right now. Don't wait. > Don't think about doing startup in binary terms. Figure out which product you want to build next and try to find whatever time to make progress on it. During this phase if you have to sort out personal things do that. If you need to take a job to support finances do it.

The product I really want to build (the bigger product), I could ship this in 3 years if I completely sacrificed the personal goals, or I could ship it in 5-6 years if I didn't sacrifice. The latter would allow me to also have more runway savings in case things go wrong. I think there are great benefits to the latter path. I would like you said, spend whatever free time left I had on the idea - even if it's only 10h/week - it would keep me invested in the path, so when the time is due to quit the job, I 'm excited to quit the job and work on the business (instead of keeping the job and staying comfortable). (I know these are long timelines, but the product is very complex to build, I have to work a full-time job for some of that time and I'm still a newbie so I'm moving slow)

> If you get a job, make sure you don't use company hardware to build it. Make sure that there are no clauses which make products developed on your personal time as company property.

For these reasons I'm specifically looking for a job at a small company (not a startup though) - up to 20 people, targeted around one product (which there are plenty of in my niche), this is why I assume it will take me a while to get a job - because they are usually looking for one person at a time. This is also why I had this idea to spend next 6 months building an open source product related to my niche, to have a near certainity I can get hired by one of these companies. I could have instead get the job in a large corp and I think there are high chances I would get it soon, because they hire a lot of people - but I consider it dangerous, because this is the kind of company that is all over the place, any digital product would be considered a competition with them and they would have the resources to bring me down if they wanted to - and from what I have heard, they do have a requirement to sign these kind of ugly IP clauses. While a small company, they don't have either money or inclination to chasing ex-employee over IP completely unrelated to their business he built in his spare time, and are small enough that probably even if they did require clauses, I could negotiate with them to not sign it.

I think my biggest weakpoint may be is I don't know any potential business partners. I have dropped out of university very soon and then I have been freelancing, so I never acquired any contacts I have been working together with. But what could I do? Looking for a partner could take a long time and there are big chances the partnership could go wrong obviously. I'm comfortable working solo and I think I can handle the psychology of it - but I have only one mind and one pair of hands. What would you say about having a co-founder vs. going solo in bootstrapped businesses?

Thanks again for your time.