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  1. #1
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    Should I just grow up?

    *note: I've asked @HAWK ; to close my old account to use this one, so that I can post this anonymously*

    Hi guys,

    I'd love to get some honest advice from you given the weird situation that I'm in.

    I'm an entrepreneur that grew up building websites. Last year, when I was 20, I raised half a million dollars for my startup as the sole founder, and became a self-made millionaire overnight.

    10 months later, today, I'm at a crossroads and have no idea how to live my life. I'm not trying to sell anything or deliver any kind of message - I'm just genuinely lost and need some unfiltered advice.

    I spent my childhood living in the projects and never had any money. Got out, went to highschool, and turned the hobby of building websites into something that financially supported myself. I then started my current company, built it out, dropped out of University, and managed to convince a handful of angel investors to take a bet. The day after the money came into the bank, I went out and bought myself an expensive suit - the good life was about to start. Money seemed to solve everything.

    The first few months after our financing was amazing. I hired some smart people, worked my butt off, and continued living my typical-20-year-old life. I would stay up late, party with friends, hit on girls, smoke weed, and eat out for every meal. At the same time, people twice my age would ask for advice while telling me how smart I am. I would walk into a store and get VIP service because the manager saw my story on the news. Life was a breeze, and I was going to be the next Mark Zuckerberg.

    Well, not exactly.

    My company has not reached the milestones that I had initially promised our investors. We haven't executed well enough. We haven't failed, but we haven't succeeded either. Now we've ran out of money, and need to raise more.


    2 months ago, I hired my Chief Operating Officer. He's a smart guy who's built a company worth 8-figures in the same industry, and has worked at large companies to handle hundreds of millions of dollars in growth. He's the real deal.

    Working with him, I started realizing that what I have been doing in business is almost a joke. It was like I was working on a school project all this time! This is the big leagues, and I'm not ready for this. I'm inexperienced, and I don't work hard enough.

    Yesterday, we spoke with two people who are interested in joining the company - both introduced by my investors. One was the vice president of one of the largest tech companies in the world (their product may be in your pocket right now). The other was the vice president of one of the largest companies in our industry.

    Any one of these 3 people can run my company significantly better than I can. And maybe they should.


    For the past little while, I've successfully gotten rid of my social life. I got off of facebook, stopped going to parties, and didn't reply to texts that weren't business related. I started smoking a lot more cigarettes and was grumpy all the time. Life sucks and I'm just not happy.

    So now I don't know what to do. I like going out with friends, playing video games, watching too many movies, and having careless fun. It's what people my age do.

    On one hand, I feel like I'm missing out on a part of my life that won't be here again, while on the other hand, there's an amazing opportunity to advance my career to where I've always dreamt of.

    Do I grow up and take this opportunity to play in the big leagues, or do I step down to have better people run my company as CEO? What would you do?
    Last edited by Mittineague; Sep 6, 2013 at 17:03.

  2. #2
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    ralph.m's Avatar
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    It sounds like all that money is not really good for you, so I'd be happy to take it for you.

    But seriously ...

    Quote Originally Posted by BrandD View Post
    I like going out with friends, playing video games, watching too many movies, and having careless fun. It's what people my age do.
    Well, if that's all you are going to do with your time, you are better off working hard, IMHO.

    For the past little while, I've successfully gotten rid of my social life. I got off of facebook, stopped going to parties, and didn't reply to texts that weren't business related. I started smoking a lot more cigarettes and was grumpy all the time. Life sucks and I'm just not happy.
    The key to anything is balance. Take a step back and look reasonably at the opportunity before you. Budget a certain amount of time that's reasonable for work each day (9 hours or so) and then down tools, no matter what, and enjoy yourself. The notion that you have to work all hours to be successful is a modern disease.

  3. #3
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    I think you should have a CEO and let your employees and business partners run the business... as you provide direction. so you can be a partial CEO, but looking from the outside, in. I think you need something new and vibrant to work on. you will be taking the opportunity to advance into the big leagues (do not turn this down) just by being more present in your work, whether it's your web development business or other business venture.

    -k =)

  4. #4
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    I applaud your candid confession and admire the humility you demonstrate in asking for help.

    It appears money was/is not the answer (nor is it the key to happiness).

    As a [very] old man* I would advise you to answer this question:
    "What is it you would like to be REMEMBERED for?"
    If you can define that, go and do it; throwing all your passion and energy into it.
    Money, Fame, "Success" (whatever that really is) are irrelevant. The mark you leave and the impact you have on others is ALL that matters.

    Personally, I have God guiding me but regardless of your conviction to His existence the most important aspect of your life is HOW you life it.


    *this means I have a lot of experience but does not necessarily mean I am wise.
    Don't be yourself. Be someone a little nicer. -Mignon McLaughlin, journalist and author (1913-1983)


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  5. #5
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    You should pesisit on what you do

  6. #6
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    HAWK's Avatar
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    Could you step back and hand over the reigns while still being a part of the company and retaining some control? It sounds like it would be a shame to walk away, but life is way too short to do something that is making you miserable.

  7. #7
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    Take a break.. and think what you really want to do..... do u really run your business meaningfully- practically and want to be successful?... Hope- yes, then grow up dude...

  8. #8
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    Quote Originally Posted by ralph.m View Post
    The notion that you have to work all hours to be successful is a modern disease.
    Too true. In fact in my experience working too hard is unproductive! Especially if your job is doing something creative/complex, your brain needs a range of stimulation for effective problem solving. Or that has been my experience anyway.

  9. #9
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    Actually the saying "no one ever died wishing they had spent more time in the office" comes to mind.

  10. #10
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    I think you should take things slowly and decide what to do after a comprehensive self assessment. You'll know what to do. Who will better know what you want than you do?

  11. #11
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    Thanks for all of the advice and viewpoints on my situation - it's honestly really appreciated.

    The past few weeks has been a rollercoaster ride. Having already hit rock bottom, I no longer feel the pressure to work reactively to meet expectations of investors, advisors, and friends. Instead, I've been focused on building a quality business the way I feel is best. I've been as creative as ever. O the wonders of not giving a sh*t :P.

    The amount of progress that we've been making in the past few weeks is amazing. I honestly think we can pull it off, and I now realize why I fell in love with being an entrepreneur in the first place. We're actually starting to create real value instead of vanity metrics that everyone except our customers are impressed with. We're still in a pretty crappy situation, but the steps we need to take are clear and, I think, do-able.

    "What is it you would like to be REMEMBERED for?"
    The stupid thing is that I always knew the answer to that before we raised money. I've forgotten since then, but now it's more clear. I went back to my notes from a few years back where I actually wrote down the answer to that question. My goal in life was to have 1 million people cry when I passed away. I want to create real value and truly impact millions of lives through companies I start as an entrepreneur. Sounds obnoxious but I think that fits well, even now, as a life goal to strive for.

    I've decided to take this opportunity and run my company as CEO to see how far I can take it.

  12. #12
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    Yes man, this is the spirit.
    God bless you.
    Good luck.

  13. #13
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    As a computer programmer, I envy your opportunity. I've never had the guts to go all in on a personal project. As I have a family, it's even harder to get into personal venture. It seems like you're overworked and natural thing to do is hire more people and you'll delegate the work to them. However, since the budget is tight you may have to be one man band for a while. Anyways, this country is all about harder you work, harder you will earn $$$. I meant that in a good way. With that said, I wouldn't lose this opportunity. At least go out with a bang w/ no regrets. There is a motto that I like to standby..though currently it's not true. It's "Have fun while making a lot of money" G'luck!

  14. #14
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    HAWK's Avatar
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    Quote Originally Posted by sg707 View Post
    As a computer programmer, I envy your opportunity. I've never had the guts to go all in on a personal project. As I have a family, it's even harder to get into personal venture.
    I know how you feel. I have a (young) family and I'm pretty risk averse. My partner has just left his job and started out with a personal project (albeit with plenty of support). I'm both excited and nervous.

    I'm glad to hear that you've come to a decision and that things seem to be working out for you @BrandD ; – long may it continue. Keep us posted.


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