Ask HN: Build my own startup or continue the high paying job?

Second, do you have an actual startup idea to work on right away? Or do you simply want to do anything that comes to mind? In my experience, it’s much easier to get started and follow through when you’re targeting a specific, known goal. I’ve seen people jump into “doing a startup” without an actual goal in mind. They spend a lot of time spinning their wheels and pivoting over and over again. I’d suggest nailing down the business idea before you leap.

Third, consider finding business partners first. Solo entrepreneurship is extremely hard and can be very lonely. It’s much easier to work in pairs or a group of 3 founders.

How bad is it consuming you lately ? Do you think about this every day ? Do you feel like if you don't do something about this, you would be very unhappy say 5 years from now ?

Let me be brutally honest hoping it helps. Most people think about doing this own thing since it is a "nice idea". But the execution part is where a lot of us fail.

So the question is: what are you willing to give up today to start something of your own ? Are you willing to give up the salary cushion you have ? Are you willing to grind day in day out for 5/7/10 years ?

Let's say you do your own thing today and 5 years from now, you decide that it is not for you and you want to go back to a job. Would you regret your decision in hindsight ? Would you hate yourself for losing all that cash you could have made in 5 more years from your current job ?

For me, the answer is No, not at all. I did not fail so you can call it survivorship bias but 7 years ago, I quit my very high paying consulting job to do my own thing. I was able to make it work but even if I had failed, I would have 0 regrets. I cannot die knowing that I never tried my own thing. Can you ?

If you have to ask some strangers on HN what to do with your life, you’re almost guaranteed to not be ready.

You’re going to have basic questions about setting up your business, insurance, contracts, payroll and HR, vendors, before you even get to your business idea.

If you don’t have that all sorted out, you’re not even in the right place yet. You’ve got some homework to do before you even take any sort of dive.

Maybe you’ve started a business before and don’t need to hear this, but from what I can tell, you haven’t and startups are not typical small businesses.

If you don’t know how to run a simple small business before attempting to run a startup, you’re going to have a bad time.

Also, I don’t know who is going to take you seriously in fundraising.

What prevents you from doing this right now? At nights and/or on weekends, building your own thing(s)? IP assignment agreement? Lack of time or energy?

My suggestion would be to start now. Start programming things. Most of the Y-Combinator advice seems to be to let the project dictate making a startup as opposed to starting a startup because you want to start a startup.

Also, keeping in mind your IP assignment agreements at work, go to your accountant and open up an S-corp or LLC. If you are very ambitious and want to get angel funding etc., start a Delaware corporation - there is plenty of advice here how to do so. I myself have an S-corp in my state, because I am not working on anything at the moment that I foresee eventually trying to raise venture capital for.

Again, keeping your IP assignments in mind - why not launch while still working? Work your day job during the day and do the side gig at night.

First of all, how much do you love money and the luxuries it affords? I went from a well paid engineer spending freely on whatever I wanted straight back to living with my parents and eating my mom's cooking. I had savings but did not touch them - they were for emergencies, especially medical ones: I had no insurance. Took me 3 years to go back to making some money, and 5 to be comparable to the original level.

Secondly, how are the people around you? I was lucky to be partially understood and not discouraged by my parents and girlfriend and accepted by my friends. Without that I would’ve quit pretty fast.

Third, do you have an actual idea for a product? You need to be in love with that idea, not with the idea of being an entrepreneur.

Finally, how much do you love sales? You’ll get nowhere without them.

Now, if you answered yes to all above, don’t convince me. Go ahead and convince a cofounder. Work together in your spare time (plus a vacation or sabbatical) a few months and build a proof of concept. Then convince an investor for some seed money for a first hire.

Then and only then you can decide to go ahead and build your own startup…

Remember: you can get anything you want in life. But everything has a price. The trick is to really understand that price. The question is: Are you really ready to pay the price?

It'll be slower, it'll take you nights and weekends, but in my book that beats the desperate hustle for cash you have when you've got 0 revenue.

By building it as a side project you can pull the trigger once you get some traction.

As a tech person, you probably hadn't had much experience with marketing, sales, business development, company paperwork/taxes .. all important stuff that will sink your startup if not done well. If you're doing this on the side, you've more time to learn the chops in those areas.

Grass is always greener on the other side, don't let that blind you to the grind.

I've had a number of connections who have done this and of course there are more famous cases like Basecamp.

There's not as much risk and there's no fear about IP. You also don't need to do all the extracurricular worrying about employer product, org direction and dealing with on call.

The hardest part I anticipate is just getting depressed from not being able to make progress fast enough. That or not having enough human/coworker interaction, which is a big deal for me.

I've been in exactly this place (big salary in big tech, started my own company). I find that these types of decisions are complex, I don't think I could capture everything in a comment, but I''d be happy to throw 30 mins on my calendar for a Zoom (9-5). Shoot me a DM on Twitter (@MattLovesMath) or LinkedIn if you'd like to.

if you have a very high conviction and high savings, the best would be to jump into it. the thing with leaving your job is you can always find another one

I have so many friends that have regretted going into startups because they have missed out on literally millions.

If you don’t have a house right now, do not go into a startup because the ones in big companies will earn more money than you and you will effectively take a break in making money for years.

Of course you might work at the next Uber, but chances are 10 to 1 that you will instead work at the next Juicero. The 5 years you dedicate to that job will see no money but the stock market will rise and you won’t see any of that so your peers will get richer and richer.

So if you have a house and enough money to keep your lifestyle no matter what, then sure. Go for it. If you don’t, then wait until you have enough. Or if you don’t care about money and are okay with things like housing being completely out of reach then that’s okay too.

It sounds like you would be able to find a similar job with similar income if you quit, tried to start your own project, failed, and re-entered the work force.

If you are at a life stage where the opportunity cost of trying to start a company for a year is approximately one year of salary, then I would try it.

Unless you have dependents/need a steady income, then it is probably too risk-averse not to try collecting new experiences.

A strong suggestion: I would find a cofounder or someone else to work with before quitting or trying a startup on your own.

Basically: if you are secure in a high income bracket, you might want to optimize more for exposure to positive, exciting opportunities, rather than play super-conservatively in a way that minimizes variance, may or may not maximize expected value, but certainly eliminates exciting upside.

1. You need to understand why you want to do a startup. "Building something of my own...": why do you want to do that? Why is that important to you?

2. Find a problem (market) you love, not a solution (product). You will be working on that problem for the next 10 years.

3. Talk to startup founders who have failed. There is a lot of celebrated romanticism of successful founders. 90%+ of startups fail though. Those failed folks are pretty smart and capable, but it's an uphill battle. If you've typically succeeded at tasks you set out at, startupland can be a big ego hit.

4. Is there a hybrid approach? One failed startup founder I know decided to work at Amazon after and try to grow a division there. He was successful in that. He took it from <$10MM to >$100MM as a GM. Zero to one is hard.

5. There's a lot of unglamourous stuff. e.g., all things legal and finance. If/when you hire people, you need to also focus on management and growing your folks.

This is gold, Even as someone who is very risk-seeking I'm not sure I would want to give this up, until I was truly ready to break out on my own, fully independent, AND have a war chest to play around with startups. However, you might have a different risk tolerance and appetite as me, or, maybe there's nothing to complain about and that's why it's boring. With that in mind:

> Within 8 years my salary has grown 8x

If you're in tech and have had that trajectory, why not pay someone to work on your startup?

I would assume that if you're that successful that your company would be willing to give you some flexibility as opposed to you just outright leaving, and that you have the financial means to do so. Rather than having this be an all or nothing thing, figure out a way to leverage some flexibility to build while maintaining some connection to your current job/position/company.

This will be much less risky than quitting your high-paying job and going all-in on a startup idea. Many startups fail for a variety of reasons, besides just poor execution.

Whatever you plan to do, make sure you have a backup plan.