I failed. Again (and again). What the heck am I supposed to do now?

Two years ago I left my entry-level Wall Street job and drove cross-country to Silicon Valley to launch a startup. To save money, I lived in my car for nine months while hacking away to get the product built. It didn’t matter, it would be worth it once the company was successful. But the business never got going. So I tried again, this time with a cofounder and a small team. Now that company has failed. Back-to-back kicks to the face. And not the high-profile crash-and-burn kind of failure that hits the front page on hacker news, but the quiet kind. The kind where no one but you even gives a shit.

What the heck am I supposed to do now?

I’m exhausted and broke. I need a job. But am I even deserving of one? I can hack stuff together but am I a good enough developer for a Silicon Valley startup? The second startup did get an interview with a top accelerator but we were ultimately rejected so I have no investor network to fall back on. No air of legitimacy that running a funded would have given me.

I’m angry and confused. I thought I knew what it took to be successful. Then I worked non-stop for two years and every single thing I did was a failure.Turns out I don’t have the first clue.

What the heck am I supposed to do now?


  • Analyze why your companies failed. Did you fail to identify and solve a real and big-enough problem? Come up with a real problem but fail to execute? Fail to gain any test customers? Ask people who tried the product why it went wrong. Then, rebound and make sure you don’t make that mistake next time. 99% of startups fail. If it’s the only thing you want to do, keep trying.

  • Revel in this moment. You will never be at this place and time again. This is the feeling of a long fought defeat. None of shame. So you found two things that don’t work. So? What’s wrong with that. I’m quite certain you’ve learned more than you ever ever imaged had you been working for a company in a cushy office chair. Take some time. Feel the air. Sniff the flowers. Run on the beach. Plant a flower. Recall why it was you even wanted to do something so crazy in the first place.

    As for this feeling of am I good enough. Yes, yes you are. You fucking camped in your damn car for 9 months to hack on a startup. Put that shit on your resume. When the moronic hiring manager asks you about a short coming you reply: “I’m overly dedicated” When they ask why? – you put on your MOTHER FUCKING BRUCE WILLIS FACE, stare into their soul and say “I camped in my car for 9 months to work on a startup” – don’t break eye contact, don’t blink – don’t breath. You will smell their fear.

    I’d trade 10 of my fresh out of college, just want to go home and watch TV and wait for the weekend S.O.B. developers for one of you.

    • Well, I don’t think you want to put a guy like this through 16 hour workdays. After all he’s been through, a nice 9-5 in sales/marketing with a good team is probably the best remedy. Dude needs to start living for more than work.

  • Get a real job – doubters never make it as founders.

    After you have at least a year of living expenses banked, reevaluate and see if you have an idea that might pay off, if you can’t convince yourself it will, you’ll never convince anyone else.

    • “Get a real job – doubters never make it as founders.”

      Horse-shit. I am, and interact with many semi-successful founders (think 200+ FTEs as a good average) and know that PLENTY of us have our own doubts.

      It is the willingness to overcome these doubts that makes you a founder. Having them only means you’re human.

      Additionally, if you never have doubts then you’re likely overly optimistic and naive.

  • You deserve a job more than 90% of those sitting in cubicles. So, don’t doubt yourself on that front.

    At this juncture, your best friend is YOU. Believe in yourself. Back yourself and get a job, as soon as possible. Reach out to your old friends. Do you have a portfolio and a Github profile? If not, build it as soon as possible.

    You need to reduce your risk. Try to do things part-time this time around. Sometimes fast and furious wins. Sometimes slow and steady does. There are no hard and fast rules in this race. Having a flexible mindset is key now, more than anything else.

  • Take a month or two break and get your head straight. No one can tell you how to live your life, that’s something you have to come up with yourself.

    Take two deep breaths and spend two months off. (Off means working somewhere part time if full time doesn’t work out, it means not having to worry about about your next meal.)

  • Hey. What you did was commendable! And at the same time, you weren’t successful, as You have defined it.

    Lets take an analogy.

    Pretend I want to be a professional soccer player. Everyday I spend on fitness, and dribbling the ball. In fact I do it for 80 hours a week, and get pretty good! I go to 8 try outs a year for 2 years, but never get chosen and then I burn out. Sound familiar?

    What’s wrong with this picture?

    Nothing. It just is how things are, it’s called reality, and when it sets in you start to notice things…things like…

    Sleeping in your car only goes so far.
    Working unsustainably only lasts so long.
    “Success” isn’t a goal, it’s a dream.
    Use the analogy to see what other parallels you’ll maybe see.

    The good news is, after all of that working out, you’re healthier than you’ve ever been, and you can rock and intramural soccer you play.

  • If your in the valley you should be hearing about companies that are doing things well and try to get a job with them. It should not be that difficult. The reality is companies love guys like you that will throw everything they have in to it. Find one of those companies, work, watch, save some money, learn and try again later. Also get engaged! Meetups, volunteer, etc. Create a network. Very important.

  • Maybe the best way to navigate to a successful startup is also the best way to find happiness everyday, instead of delaying that for a later reward.

    Delivering something of value is where happiness lies. Try to find a path where you are delivering something of value each week, so that you aren’t potentially loosing your whole investment if you aren’t lucky enough to get the big win you’re looking for.

  • Be careful how you adjust your expectations after failure. There is a difference between changing your time hedging between activities (job vs startup), and changing the type of aim your startup was pursuing.

    Did you originally plan to solve a problem that would increase someone’s personal life, by selling a bold change of behavior? If so, be careful whether you want to move onto a startup that is just focussed on making a small passive income.

  • It is ok to fail but fail quickly, gain feedback quickly and adjust, take a look to lean startup video and book !! hope this helps

  • I disagree with the above comment that success is a dream and not a goal. It’s a goal, I think, but not an easy one.

    Hey, you know what, to me you are successful. To me a persom who has found the strength inside him to abandon everything and sleep in a bloody car for a bloody year is already successful. You wasted what – 2 years? How about those who are in their 40s and they are in middle management achieved nothing?

    But you know what’s the main difference between you and them?

    You have a story to tell to your kids much more exciting than “so I spent 40 years selling pens and pencils..”

    So brace up. Take a month off. Go to your parent’s place (and dont even think of feeling defeated – lost battle doesnt mean lost war) and find ground. Then start again, BECAUSE YOU CAN.

  • Go back to market.
    Go back to the problem you are trying to solve.
    Put yourself in that problem.
    Empathize with the intended user.

    And refine your product, to fit that market.
    Then approach as many incubators, with your figures and numbers, put together a good pitch. Numbers and stats dont lie.
    One of them will dig what you are trying to do, and for the least you’ll get some cash to run you a few months while you figure stuff out.
    All the best ninja/ninjaress.

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