Pretty dismal. However I learned some things from the startup that I didn't appreciate at the time. One was grit, another was being able to strategize about a variety of business problems, another was humility, and I also honed my quick learning skills.

These ended up, over a few years, landing me a plum startup job, a FAANG job, and a funded retirement.

The big picture is always out of sight. If you keep learning and stay humble but stubborn (don't give up) it will work out reasonably well. I still think I stayed to long on my startup adventure but I am not stressing about it.

Three years and two failed startups later, I had only $200 left in the bank and decided to throw in the towel.

I started interviewing for jobs but wasn't having much luck. This was a real low point in my life, I had asked my family to live on the poverty line for an extended period of time with the promise of success in the near future. But I had failed. And now I couldn't even get back into the career I had left behind.

I started working on a third idea while looking for a job. But after suffering knock back after knock back from potential employers, things were looking pretty bleak. A family friend wrote out at a check for $4000 to see me through until I got back to work. I accepted the check but it was a humiliating experience to do so.

"The temptation to quit will be greatest just before you are about to succeed."

Then out of no where and completely unexpectedly, my latest idea went stratospheric. It was so unexpected that even now I sometimes pinch myself and wonder how it all happened.

I never did cash the check my friend gave to me and keep it in my desk drawer. From time to time, I take it out and look at it to remind myself how far I've come.

in retrospect it was a pretty brave/risky thing to do, but it didn't feel like it at the time. money came, money went. simple as that.

to a certain extent, i feel the same way now. if everything went to hell tomorrow, i could just get a job and probably earn in the neighborhood of $150k/year on salary.

we, the founders, have 100% ownership of our company, which is profitable and growing at approximately 75-100% a year.

5 years spent in megacorp life versus seeking funding and giving up ownership was well worth it.

That 20k turned into a new job, which I would not have been able to get otherwise, that greatly exceeded the money I spent failing.

Sometimes success is not exactly what you could have imagined.

I was so burned-out from the experience that I had to stop for my own mental health. I got a normal job three years ago.

Since putting the startup on indefinite hold, I've been able to learn new sports, buy a home, and generally enjoy my life without the constant feeling that I had to be working more and spending less. My life got dramatically better.

So while I would have preferred that the startup succeeded, walking away after four years was far better than continuing down that path. And because the technology I had built was really impressive, it only took a couple months for me to get a job paying more than I ever had before.

For me I'm living like a pauper - broke, in debt, family-less (g/f of many years wants stability before we have a kid) and well right now I'm not sure why I chose this path the past 7 years (2 start-ups).

I do have a nifty/interesting resume, a lot of cool stories/experiences of my own that a day job would never provide and an idea of mine has been copied/worked on by dozens including one that now has 1.5 million users/raised $3 million (not me though).

IS it all worth it?

EDIT: I find myself asking this question when the rollercoaster slows down (slow times/nothing exciting happening .. heads down development). Currently, the coaster is going 10MPH, though two/three weeks ago it was going 100MPH.

When I was an intern at Goldman Sachs me and my roommate rented an apartment in the Tenderloin for $600 a month. I slept in the closet. We stayed at the office 24/7 and focused on work. My former roommate is now a GP at a major growth equity fund.

I opted out of finance and instead of getting a banker salary I lived in another closet for a bit and a shed with no shower or bathroom (I had to walk to the main house).

I lived off $700 a month and pieced together a seed round in 2009 and things slowly got better from there.

Now I have a public company and can say I’m one of the few founders to get my investors a unicorn exit.

I know I am the outlier of outliers and had more luck than anything else, but god damn don’t disdain others who are willing to sacrifice to give it a go.

I was working in NYC, and on Wall St (as a programmer). I was 2 years out of college, so 25 or so, and had only minimal savings and some college debt left to pay off.

The "conventional wisdom" in my circle of friends was, "This is a really bad time to quit a stable job and start a small company, because the entire economy might collapse." I had nothing but evidence in front of me: from my office window one day, I could see streams of hundreds of laid off people leaving the Lehman Brothers building, with cardboard boxes of personal office items in their hands. Friends of mine who were smart and hard workers were getting laid off from their NYC jobs left and right.

When I worked up the courage to quit and pursue the startup, and I announced it to my colleagues at work, quite a few of them took me aside and said, "I get that you already made this decision, but I'm really worried about you given what's going on in the economy."

I think pg's essay, as well as the general mindset of YCombinator, helped me and my co-founder have the attitude of, "We'll try this, and it might fail, but if it succeeds, it'll be awesome. And if it fails, despite how bad the economy is, we can still fall back on just working our butts off to find another job."

Anyway, it wasn't easy, for sure. Though we managed to get seed accelerator financing ($20K) from Dreamit Ventures in Philly in Summer 2009, we then bootstrapped for 2 years in the startup wilderness until our seed financing round of $800K in 2011. I don't think most people, young and frugal or not, would last that long on non-employer healthcare or with only consulting/freelance income to pay the bills. I wrote about that financial reality here:

https://amontalenti.com/2011/04/02/not-for-the-faint-of-hear...

Also, zooming forward to 2020, I think the current economy is much more startup friendly than 2008-2009. In the period we started in, seed financing was not very mature -- we were still living in the shadow of the 2000-2001 crash. NYC had a very small tech startup community in 2008-2009. The 2008 crash, being a "financial" crisis, also depressed venture capital investing at the same time. By contrast, this Covid-19 recession has split investors, where retail/consumer stocks are losing money, but tech stocks are growing by leaps and bounds, and many investors are now trained by the success of low valuation seed investments from the 2008-2010 era, which eventually led to IPOs and exits in our recent tech bull market. So, if I weren't still running my company and if I were working for a BigCo like I was in 2008, I would definitely start a company now, because there's really no downside whatsoever. That is, no downside except the opportunity cost of your salaried job. (One other counterintuitive aspect, though, is that, perhaps, starting a startup now is such an obvious decision that you'll be competing with a lot of other seed stage founders, assuming they are as rational as I describe here :-) ...)

Also, about a year ago I provided a little advice for how to bootstrap your company if you do get started and you are not of any means. Hope it helps someone:

https://news.ycombinator.com/item?id=21506297

What I did.

1. As much as I swore never to return to work, I got a contract job (6 months). It stung, I wasn't in a good headspace at that time.

2. Borrowed some money from my family to cover the mortgage.

3. Saved my house from foreclosure by 6 hours using the borrowed money and my salary.

4. Kept the business running in the background and working on it at night.

5. Worked for 12 months, paying back everything, enjoying seeing my family eat good food once again and getting the occasional night out. What a treat to go and see a movie once in a while :) I can tell you going to the bottom gives you an incredible perspective on money and not what you think either.

6. Built up my contacts and pivoted my business. Lots of hard work and 2 years later I have 2 offices and a team of 7 people. (this is obviously a longer story, but for another day)

I recommend you get a job for the short term and get your life back in order. I can tell you that trying to grow a business while you are incredibly stressed about how you are going to eat or keep the lights on will only result in panic decisions and they will be bad.

If you have a passion to change the world, your families life and your own for the better, you will get back to business soon enough. Business owners have a burning passion to succeed at all costs and only consider this a temporary set back.

(Just a side note, some people have a fantasy of working hard (but not really), having lots of fun, getting traction easily, getting investment, get bought for a few billion and live happily ever after. If this is your plan, I would suggest setting up a career path, it will lead to a much happier life than a startup, in which the failure rate is very high and you have to be prepared to fail many times. Not work towards failure, just accept it as part of the journey.)

First I kind of felt sorry for the guy, then I quickly realized there are much worse perdicaments to be in.

I was living in Louisiana as a college dropout who had sold one company and (fairly easily) making about 200k/year between one full time job and some side work.

In Louisiana that is good money, like REALLY good money, I could've easily lived for a very long time and saved a lot on that, my mortgage there is only about 1k month with all the utilities paid too.

But several months ago, I quit my job, stopped consulting and moved across the country to CA to work on my next startup.

after about 5 months I started to get very nervous, my accounts were seemingly dwindling and reveue still seemed a ways off for the startup.

So naturally we started looking for funding only coming to realize noone wants to fund a startup simply because they need the money.

Then I realized something far more important.

I have skills. I consistently made very good money before. I was capable of this again. I put a few feelers out and quickly got to help build out an awesome new product for a really great guy with deep connections.

Fast forward a few months and our little startup now has strong revenues, things are looking up on several fronts and that little consulting gig I took let me earn several thousand dollars, pay off bills and build a great relationship with someone who is sure to be a very successful first time entrepreneur (he's already had a successful career in finance).

All that to say if this guy was making 200k/year before chances are he has a good skill or set of skills and he should be looking to that to dig him out of this hole not to investors for funding for what sounds like a failing endeavor.

Most people aren't as fortunate as I was or as it sounds like this guy is. Many people in a similar situation to mine would not have had the skillset or network to pull of what I was able to and they would have likely had to get a regular job somewhere or move in with friends etc. When you have a skillset that allows you to generate large amounts of income your life just is not that hard.

Sorry for the rant, but someone should tell this guy to get over himself just a bit. Whether he believes it or not, he's a pretty lucky guy

Be flexible. Your determination, focus, and drive allowed you to power through on a project that you are now recognizing in hindsight might not have been the best option. Changing targets isn’t quitting, it’s counter-attacking.

You are only 30. So many opportunities to keep swinging. All it takes is one hit. Be adaptable. Let yourself recharge. Figure out how you can take more swings in shorter periods of time. Figure out how each swing can work together to push you further towards your goal. As much as your work seems a failure now, there is a ton of learning in what you did. It will come with time. An incredibly successful entrepreneur I know said his break through happened on his 12th try. That’s a lot of projects.

Get away from the HN/SV bubble awhile. It’s like Facebook in that you only see the successes. The struggles are mostly manufactured fluff and don’t compare to what you put yourself through for 6 years. Most startups are built by people who took very little actual risk. Taking a year off your career at Google to go to YC isn’t a real risk, that’s like calling HBS a risk.

Don’t let people say “maybe starting a business isn’t your thing.” If a soldier got wounded on the battlefield, would you say “maybe war isn’t your thing” and that we should only celebrate those who didn’t take a hit? Of course not.

You’ve proven that you are an entrepreneur. You have the determination. You need to rest, recharge, and figure out what other skills need work and how you are going to counter attack. Whether it’s starting a business or doing whatever else you want to do in life. Seriously, building shit is hard and clearly you have the aptitude for it. Good luck in your journeys and know that you did something.