Should I give up trying to be a founder?

"It would be hugely embarrassing to go back to working for any other company. I would have been much better off financially if I had stayed at my high paying dev job."

Well, you can be broke and keep on doing something that clearly isn't working for you...but maintain your pride in doing...something that isn't working and being unsuccessful.

Or you could be "embarrassed" with a high paying dev job. But honestly, that is all in your head. No one really cares that you failed and came back to a high paying job. Nobody is thinking about you that much.

IMO, stop doing things that aren't working, work for someone else for a while, get some money, recover, learn why you are not being successful building your businesses, and maybe try again...?

It sounds you have a lot of experience under your belt.

Is it pride and self doubt your problem?

Do you want to be the CEO of a successful company? What do you consider a successful company?

By SV standards a company with 1-4M in profits is a "lifestyle business". Would you be ok with having this kind of business and maybe selling it for an EBITDA multiplier?

Have you consider buying a small company, optimize it and sell it?

> "It would be hugely embarrassing to go back to working for any other company."

I don't have any advice to give, but to this statement above - it's absolutely not embarrassing at all.

You will bring a tremendous amount of knowledge very few people possess and you should lean into that.

One thing though you will need to make any future employer comfortable with is that you're ok taking direction from someone else ... because a future employer (if you go down that path) might be concerned that due to you being the boss for so long, you won't be able to adapt to now having a boss yourself.

I wish you all the best.

"The stress is enormous." doesn't sound like a life I'd want to choose to live if given the option, especially when you're not receiving enormous rewards in exchange.

A big part of life is constant reinvention of self, and other people's opinions are largely irrelevant.

Even if you turned your current business around and do sell it for a few million, we might be seeing a post titled "Ask HN: I exited. Now what?"

If you want to you could get a normal job or keep it running on the side. Personally, I was prepared to do anything until it worked out as I had no option to get a job.

My history: https://dare.fail/

Get a cosy FT (10hr/week actual work) boring CRUD job at a place like a bank and hustle on the side.

Startups are about enough stress to perform but not so much that you're crumpled. Can't perform when you've got bills mounting and no exit in sight...

Forget about the embarrassment. Irrelevant. Forget about the people you work with. There are great (and awful) people everywhere. But also forget about grit and persistence; that's just more ego talk, completely unrelated to whether your customers will buy from you.

Instead, ask yourself if you even want to be in business anymore. It's ok to pivot if not. You could always work a regular job for a few years, get out of debt, and build up some capital for your next venture.

Before you pivot, though, ask yourself: If this business was even slightly profitable, would I be happy to keep working on it?

If the answer is no, pivot. But if the answer is yes, you need to dig into what's not working.

You mention having $200k in debt. If you didn't have to service that debt, would the company be profitable? If so, there are many potential solutions. You could sell some stock. You could refinance the debt on better terms, telling your lenders it would be better to be able to pay them back in 5 years than to declare bankruptcy and pay them nothing.

How are you customers? Does anyone LOVE you? If not, why not? What would it take for them to love you, and thus attract others to your service? If you have at least a few customers who love you, ask them what they love about you, and considering giving your product/service a greater focus on those aspects where you're knocking it out of the park. Winning over your first 10 diehard customers is infinitely harder than the subsequent 100+ diehards.

If you have a product people love and can be sold profitably, but it simply needs more scale, look to marketing. But beware: Marketing is a results multiplier, not a results creator. You need to have something good to market. Great marketing will help a successful product succeed faster. It will also help a failing product to fail faster.

Finally, you have people on your payroll. Could you conceivably keep running the business without a few of them? Depending on how much you're paying them, that $200k of debt could be handled by simply eliminating some overhead. I know it sounds cold, but they'll be just as unemployed if you have to shutter your business. Better to chop off a limb than let the whole enterprise fail. And as much as you might like your staff, they won't be there for you if/when the business fails. They'll find other jobs and you'll be left holding the bag.

These are just a few ideas. But based on the information provided, I don't think anyone can give you good advice on whether it's time to close up shop and give up on your entrepreneurial dreams.

Bro just make a bunch of SEO based casino/sportsbook affiliate marketing sites or some content farm. In 3 years you will have enough money to do any startup you want.

I am on the first leg of your journey. Quit my extremely high paying FAANG job to co-found a startup as a CTO. We raised a crazy amount of money for seed. I am just so burnt out (and genuinely feel I am not qualified for the job). I want to swallow my pride and call it quit despite the company is doing ok with a lot of cash left in the bank.

But two things keep me going (in an unhealthy way): 1. My ego and embarrassment 2. credibility with the investor network we built up. It's not sustainable for my mental health but I frankly don't know what my next steps are yet.

All I can say is best of luck to you. I would love to hear how you bounce back from the VC-funded burn to bootsrap another one.

It's not embarrassing to go work somewhere else. It's smart. It sounds like you don't have a passion for your current business. Do something else.

I worked at a company where the founder raised X million, blew through his life savings, was forced to take a pay cut, barely making a livable wage. The board then brought in a "professional" CEO, who couldn't raise any money, and left after less than a year. In the process, everyone was laid off (including myself, briefly.) A short time later, the company was acquired for pennies on the dollar. As one of the first few employees, all my equity was worthless. I mean, it should have been, seeing the company barely made enough to pay the AWS bills after 6 years. It was not a good situation, but live and learn. I should've moved on earlier, but since I was one of the first people hired, it was tough for me.

Full disclosure, I've yet to make an exit, but it sounds like you are close to profitable. I would say if you can get to a multi-million dollar exit within a couple years, go for it. If you cannot, unwind and go a lower-stress route. Not every all-star team makes it to the world cup and wins, it's quite alright. Only you know how close or far you might be, realistically, but if you power through and it works you'll feel a lot of satisfaction for having had the sustained enthusiasm and stamina. Either way, you can look back at everything you've learned and experienced and consider it a success, too. When you distill what you learned into material for others to shortcut the process, then you will be a complete success.

Take a look around dude. Interest rates are very high making the funding environment rough and it effects everything. There is far less liquid capital because borrowing is so expensive, it is set by the central banks. When the money is expensive to borrow; it effects absolutely everything including your business.

You are going to be looking at this situation for some time. Only the very top projects or projects in AI are getting funded, a lot of consulting has dried up.

Is anyone getting rich right now? I don’t know.

Take a serious look at the macro economic picture. It’s not great. This is a recession. It could last years.

Or the federal reserve may drop rates but they don’t seem to be close to doing that.

So take the pain you are in now and project it out until next year when the fed is saying they may drop rates.

You may be in pain for a long time.

Is this a level of pain you can tolerate for that time period? Are you in AI where the capital is at least easier to get?

A lot of startups are folding or have folded silently behind the scenes or died at this point.

We are in a bear market.

Understand the context. This is what happens in a bear market. It sucks. No one is getting rich. It’s hard to get money. It’s happening to everyone not just you. Everyone is in pain.

I personally am in pain myself. I got into startups when things were super hot and fun a couple years ago.

I’m not having fun right now.

I’m getting a real job and I don’t want to. I have debt. My quality of life sucks.

It has been going on so long, I mentally threw in the towel and decided to accept that I am going to just fail and then have to restructure my life.

I might have to sell some things I don’t want to sell.

The only silver lining I can find is: I have realized that it’s a combination. Nothing is working, so I can get rid of my whole life and only become happier.

Sell my house, move, find a new market.

It is actually very exciting once you let go of the albatross.

When the piano you are swimming with becomes too heavy, you cut the piano off and try to make it to shore.

Your embarrassment will turn into joy when you reach the beach, poor and wearing only a loin cloth going “oh my god, I am free.”

Cut that shit off if it is killing you.

There is a clock. You can only take the pain for so long.

It sounds like you are only being pulled downwards

Make a list right now:

Good things about this situation

Bad things about this situation

If the list of bad things is 2x longer, end it

Just some food for thought questions. It seems like you're well-placed to thrive if/when an economic recovery occurs, if you can hang on that long, so you should consider doing what you can to increase your runway.

1) Do you have a significant other who is onboard with your plans and who is capable of helping fund your living expenses while you push this over the finish line? A teammate with some income would be a big value here.

2) If you own your home, are you in position to downsize and sacrifice that to ensure that the business succeeds?

3) Do you have the capability to take on a lower-paying and less stressful tech job that requires a smaller time commitment to help fund your dream? If you were a great FAANG developer, you can probably find some lower-paid, but easy tech job for that you can bang out in ~20 hours per week and spend the rest of your time on your own business. How big is your weekly financial deficit? Would a lower paid job fill that gap?

4) Do you have the capacity to shed expenses? If you have employees, that might sadly mean some layoffs.

5) Can you quickly raise some money by throwing some trendy "AI" labels on your website and trying to capitalize on the trends?

6) Have you considered raising prices? If your customers do love your service, there's a chance that they'll accept a price increase rather than seeing you go out of business.

7) Maybe a dumb question, but why are you seemingly focused on a big exit rather than building a sustainable business?

I am in a pretty similar situation to you: founder, but no big FU money exit. Debt + stress slowly killing me. Wondering if I can make it, how embarrassing to go back to getting a job, etc. Know that if i can stick it out, there's a few mill.

Well, I can only share what I did, which is call up a couple of friends of mine who I knew needed my skillset and did a couple consulting contracts for them, which then led to taking a full time position.

Do what you need to do to take care of your mental health and forget the rest.

Taking on side work doesn't necessarily spell the end of your business, but one thing is for sure (and this I also had to follow for myself): no more putting the business finances ahead of your own.

I had to get my business to a place where it wasn't losing money so it could continue without my everyday involvement. If you can't do that - then scrap it, take a job with a steady paycheck for a couple years, pay off your debt and, if it still sounds appealing, you can always start another company.

It's tough. Best of luck to you!

Sorry for not answering your original question, but how could they dilute your ownership in the first company? Did you not have pre-emptive rights to also acquire more shares with the $1 price? Not sure how things work in the US.

You make it sound so ... unaccomplished ... to just reach out and get a high paying "easy" job. Do they exist?

I have yet to find an "easy" high paying job. I've been stuck in the $50K~75K range my entire 17 year career. So maybe realize for a split second that there are many, many people making much less, experiencing much worse.