Path to take after startup failure

I have attempted two different technology startup ideas in the past six years and my cofounder and I finally called it quits earlier this year. It has been a heart-wrenching ride because we poured our heart and soul into them like many others.  Having been mentally exhausted, I decided to take a four month trip to reassess my life as to what I want to do next. It was a much needed rest and I just returned from the trip fully reinvigorated. The problem? I am having a hard time deciding whether to pursue another startup idea or get a job.

Financially, I am not in a super bad place, even though I haven’t earned any income for the past six years. I bootstrapped my own business so my immediate savings is pretty much depleted…not a good thing obviously. However, I can potentially sell my house or take out my retirement savings to keep myself afloat if I have to. The alternative is to get a job. Being a developer, I should be ok in that department. The trouble is, I still haven’t given up my dream of having my own business.

People say you learn the most from your failures and I definitely learn a lot from them. I now know more of what it takes to make my startup a success. I am developing some new ideas but I don’t know whether I should pursue them or not.  The choices are: a) Get a job for the next little while to regain my financial footing or b) Work on my new ideas. My friends and family want me to choose the former because it is the sane and safe approach. I, on the other hand, want to give myself a max of 3 months to figure out whether my new ideas would work or not.

I am 39 yrs old and single. Not young by any means, but I still have my energy. I am worried that if give up now I might not have the courage to try again. The reality is relationship and societal expectations always force one to give up their dreams. Should I get back into the workforce?  Am I crazy to try entrepreneurship again so soon?

  • You are basically 1 year away from being un-employable in terms of your age (if you are employable based on the last 6 yrs is another question — you could be looked at as difficult to manage since you might not take directions).

    Therefore, I urge you to do (a) and once you are on the job for 3 months, you can do (b) in the evenings and weekends.

    I am 46 and missed the boat. Don’t put yourself into the same position!

      • And I’m a 22 year old. What would you say my age is ripe for? I currently have a startup (trying to get more customers) and also start full time job in the coming months.

  • I’ve been where your are. I just got back from a year long sabbatical and returned completely refreshed. I have decided to take the startup approach. The reason being,

    I’ve never felt more rested, excited, full of ideas, and ready to work. Don’t waste that kind of potential sitting behind a desk. When you hit 50 and you’re sitting behind that same desk, asking yourself what could have happened if you had tried one more time…. That “what if” will haunt you forever. This time do it differently though. Analyze everything you did wrong before and try to learn from your mistakes. Take on a co-founder that can help bring you up rather than just follow alongside you…. Hope that helps. – @hookemgriff

    • OP here. Thanks for the encouragement and insight…much appreciated. It is good to hear from people who understands what you are going through. I haven’t decided what to do yet, but I really hope you succeed in your endeavour!

  • Keep going. People often fail a few times before they hit it big. As long as you are learning, are healthy and still have the passion keep going. Otherwise, you will be full of regrets later.

    Some people come close to success but give up just before.

  • You’re very late in your career to not be planning for your future. Sure, do something risky on the side, but get ready now for your age catching up with you.

  • Startup failure is the best failure one could aspire for

    The successful CEO of hopstop, which was ultimately acquired by Apple for a bundle, had failed repeatedly at founding his own company. The hard earned lessons that he learned along the way, and the relationships he built with investors, eventually led him to being courted to take hopstop to glory.

  • I don’t buy into this “your age is catching up with you” bull shit. The average age of a first time entrepreneur is 40, and you’re not a first timer.

    Take a full time job where you can become an asset quickly and be fully productive at 40-50 hours a week. Once you’re there (within a few month of starting usually) start working on your new idea(s) nights and weekends. Use that full time gig to fund your new startup while you’re validating the business.

    You’re in a good spot where if you get to a point where your idea has legs you can start thinking about quitting your job to focus on traction/fundraising/revenue, etc. The key here is using that FT job to fund your idea while you de-risk it to the point where leaving your employer makes logical sense.

  • Reading the amount of emotionally-charged language in OP and comment posts, I’m pretty baffled. I’m in my 30s and have worked the startup beat.

    If you end up on your deathbed wishing you spent more time building your “world-changing” startup, you’ve got a sad view of what constitutes “world-changing”. You might be senile at that point, though, so some delusions would be expected.

    Maybe that’s harsh–but really–all of you all, calm down. You’re not likely to make wise decisions if there’s so much emotional valence to the entire thing.

  • OP here. Thanks to everyone who responded! Really enjoyed all your perspectives regardless whether we agree or not. It is good to finally have a place to discuss our experiences!

  • Im in the same spot. Albeit younger. Been out of the job market since end 2004. Spent 3 yrs studying and the rest dealing with health for a year after which I startedy business. Shit thats 10 yrs

    No wonder im having a hard time finding a job. I have another startup idea. There us def a market. I just need some cash. I plan to work and earn some money or then again reading this..aybe its best to get working on my ideas and do some freelance on the side..thanks for sharing !!

  • I started my own company last year and was super confident about it. Had customers and projects flowing in and gained some popularity in local business community. However, capital ran short, projects started getting stuck. Cash flow is a nightmare. I hate to tell my staff to leave but I dont have money to pay them. Office is also costing too much. I tend to put my business in different mode. Like working from home. My business nature can so done without an office.

    I am thinking to get a job to cover the expenses for myself. Got fews interviews lately. I am pretty confidence about what I have gained from my startup. I dont hide the fact that I am running a company. They seemed a bit hesitant when I told them so. Got a job offer from a 5 star hotel for matketing manager position but they rescinced the job offer after 3 weeks. I dont know why. Maybe they started feeling the fear…haha. I am not much disappointed. Ya know, the good thing about running a business (and fail) makes you be able to cope up with the feeling of being rejected. Compared to the failure of your own business, the failure of getting a job is really small. There are fish out there and those who have experience as entrepreneurs will surely catch many. So I am not worried too much.

    I will get back to the market for job but surely will turn back to business when I am ready again.

  • I am 33 years old and in the same position as the OP. The job hunting process is demoralizing. Even hard skill development positions makes you jump thru junior hoops and then reject you because you are not ‘Test Driven Development’ enough… Pre-seed startup is all about hitting the market ASAP and get market feedback. They qualify you as a dedicated corporate developer instead of someone doing 5 jobs at once and thus you’d be a lot better if you are given the time and stability to focus on just 1 aspect….

    I am wondering what did the OP ended up doing? Keep drawing on retirement funds and keep trying? Or just go back into corporate and be taken as a junior?

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