Sold my startup just before it succeeded – Now almost broke and back to square one

How do you recover from a success (first success after a multitude of failures) that you let slip through your fingers – by selling just before it took off?

It is eating me alive. I’m almost back to square one (broke, no ideas) and can hardly hold myself together. I try to pump myself up to try something new but the thought that had I held on just a little longer I wouldn’t even be in this position zaps my productivity.

Faced with the prospect of having to reenter the job market (after having actually built something that works) is a nightmare that I never thought would be realized. But here I am.

Every day – completely paralysed by the outcome of my decision.

Really would appreciate anyone’s advice here. Thank you.


  • The only advice that you need is to get the fuck up, get yourself together and get it done. Shoulda, woulda, coulda. You need to move forward and stop looking back.

    Also there is still leverage in the fact that you started a company that has succeeded. You should own that.

    Go help another startup out with your expertise and get your mojo back.

  • The fact that you managed to create something that went on to be a success should be a motivating factor not a demotivating one. Very few people actually succeed in business – yours did, although the rewards slipped past you.

    Also perhaps you can give us more background on why/how that happened so we all can learn from it?

    • +1

      Now listen here you….We are all killing ourselves here to raise money, get paying customers, demonstrate traction. So before I get angry… you should feel damn proud. You’ve DONE IT. So think yourself lucky. If you have any logic left in you:

      1) Realize that you will have A MUCH MORE EASIER TIME RAISING MONEY THIS TIME

      2) Benefit from your lessons learned. DONT do what didn’t work last time and DO do what did work last time

      Hope there are others here to knock even more sense into you.

  • I spent about a year building up the high quality traffic to the site, mainly through white hat SEO (read: good but very difficult), while my competitors used every black hat tactic in the book. For a long time I felt that I was playing catch up. Eventually I decided it time to move on, so I sold. 2 months later google seemed to have finally recognised what id been doing and gave the site a much much higher ranking. Demoting almost all of my competitors. This quadroupled revenue almost overnight and it has continued to grow.

  • Remember how hard it was to raise money with ZERO track record. Now you’re the founder of a successful business that you sold, you’re a sure bet for future money!

    Take the small win, take the experience, and win big next time round!

  • You did it. Whether you made money off it is secondary. You created something from nothing. You made a positive difference to this world. You effin did it.

    You did it.

    You’ll do it again.

  • You should be happy. You can actually make something greater out of that experience. You said it is a success now, you can use that success to your advantage. You are still the founder of that startup and you can use that credential to attract talents and investors in your new startup. Go look for someone who have a good idea, collaborate, and use your previous success to your advantage.

  • Can you still work with the company you created? even as just an adviser or creative idea person. Getting to spend time with your baby again may bring some satisfaction back to you. Money alone is not the key to happiness. If the company is running itself right now without your involvement, maybe you could help in some other way – i.e. do things to help that you would have liked to done originally but weren’t top priority or feasible with you having to manage so many other issues. Now that company is sustaining itself without you, maybe you can come in and do some special projects that may prove to be very valuable to the company and bring more rewards your direction. Also working there some may help bring closure. You will get to spend time in your creation but it may also help inspire you to create something new yet again.

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