Falling Out of Love (w/ My Company)

Written By on February 14th, 2012 | Category: Startup Life | 26 Comments

2/52 - It's Raining Men!

Andrew Draper (@andrewdraper) is a designer and hacker. He’s been an entrepreneur in one way or another for most of his life. He co-founded Manpacks 2 years ago, a service to help guys remember to replace their essentials and give them more time to do the things they’d rather do.

There’s a lot written about having passion and how it’s the key to building something great, but nobody talks about what to do if after you successfully raise a seed round, get thousands of customers and get lots of press/social media attention you find yourself unhappy, unfulfilled or no longer interested in the challenges your startup faces. Here’s how I handled it.

When a spark no longer lights a fire

Ignite the moment...

Years ago I played in a few rock bands, put out a few records and did a small amount of touring—we had a “policy” in each of the bands, something like: “When it stops being fun we’ll stop playing”. I was never the guy who invoked it so I never had to consider what the ramifications of invoking it actually meant—until recently.

I’d had “the thoughts” off/on for a number of months but always attributed them to the normal entrepreneurial roller-coaster of seemingly bi-polar emotions. In early December I flew out to San Francisco for a week and was asked how things were going, with my most recent startup, Manpacks, by a number of people I respect. I came to the realization that I was faking it, and generally being dishonest (especially to myself) every time I answered.

We’d enticed thousands of people to subscribe to Manpacks, received awesome press attention, recently raised a seed round, and hired a developer and a marketer. I was incredibly proud of what we’d achieved (and still am) but at the end of the day I wasn’t fulfilled and felt I could be doing something that interested me more. So, we’d gone to war and in the middle of the battle I was thinking of waving the white flag.

After talking to a few people about how I felt, their answers were all basically the same (paraphrased), “If your passion’s not truly there, life’s too short and you won’t be doing your best work.” I thought to myself, “Wait, they were telling me to abandon ship in the middle of a storm?” That’s the exact opposite of the type of person I see myself as. I had some soul searching to do.

The Breakup—It’s not you, it’s me

I'll Give You All I Can...

That night, I tossed and turned, wondering, how might Ken, my co-founder, react? What would the investors think? I’d helped hire and sell a vision to some great people, what would their reaction be? Was I screwing up everything I’d worked so hard to build over the last 2 years? Did this make me a quitter? Would this make me unable to raise money for my next adventure? I’d had many sleepless nights contemplating. When I awoke the next morning I knew deep down it had to happen, that today was going to be the day.

So, what now?

Practice. Like any good pitch I practiced for an hour or so, running various scenarios to how I thought Ken might react and how to best mitigate the reaction. Fearing he might think I was abandoning him, that I was dumping everything onto him, destroying what we’d built, the list goes on. I feared the worst and practiced every possible way I thought the conversation could go…except one.

After some reflection I made the call…and got voicemail. Ack. A few minutes later my phone rang. Gulp, it was him. I stared at the phone and let it ring probably 3-4 times. I picked it up.

The one scenario I didn’t consider while practicing? Ken totally understanding and taking it all quite well. The truth is, like anything tough or difficult, thinking about it is always worse than the reality of doing it.

I don’t want to put words in Ken’s mouth, but he had realized on his own that my heart was no longer in it. He had sensed I wanted something different and to go on “faking it” would’ve harmed the company more than it would’ve helped it. With that, we put together a plan to make it all work out for the best and allow me to be minimally involved going forward.

Everyone’s happy. Awesome, right? I can work on something I’m truly passionate about and we can all have cookies and milk and go to bed with visions of sugarplums…not quite.

OMG, WTF did I just do?

Olive's First Bath

I still had a few days in California so I worked on some ideas I’d been toying with for awhile, hung out with friends and everything was great. Then I went home, started creating MVP’s, testing ideas and trying to hit on a winning combination for an awesome, fast-growth company. And, my lizard brain took over for a bit. It still does from time to time which means waking up at 3 am, thinking my entire world is collapsing and I’m screwed. It means looking at the bills piling up and wondering WTF I’ve done—you know, the glamorous stuff no one wants to admit is real entrepreneurship.

Me? I love it. Even with the ups/downs. I have no doubt I’ll be able to build another company that’ll leave a dent and I won’t be listenting to my lizard brain, the naysayers or anyone not truly all-in. It might well be a bumpy ride but it’s going to be truly awesome.

It’s been said many times, startups are hard. The only thing that is certain is that there are ups, downs, lefts and rights—and you have to be really good at bobbing and weaving sometimes. BUT, make no mistake they’re even harder when it feels like you’re stuck having to do something you’re really not into anymore. Staying out of loyalty is actually doing more harm than good. I’m not advocating jumping ship as soon as times get tough (which they will), just gut checking to make sure you’re passionate enough to make it through those times. My hope with this post is if you have similar feelings you’ll realize there’s something you can do about it, you just have to be willing to see it through and feel that, no matter what the outcome, you and the company will be better for it (and hopefully learn something in the process).

If you are having similar thoughts, and need someone to bounce what you’re thinking off of, hit me up, I’d be happy to listen and offer any help I can. Otherwise, put your head down and get back to hustling/hacking—there’s gold in them there hills.


  • http://mercurygrove.com Mike Mason

    So what’s next for Andrew Draper? (insert plug here)

    • http://twitter.com/andrewdraper andrew draper

      The truth is there’s not really anything to plug…yet. 

      I’ve been looking at different problems I find interesting and trying out a number of ideas I’ve had but haven’t found one I feel can grow in the manner I’d like—when I do I promise I’ll be the first to yell about it loudly, but for now I’m very much in discovery mode.

  • Anonymous

    I am in the same position as you Andrew. 33, working the corporate world as a software guy for the past 10 years and I am truly bored. I need to change the world in my own small way! If you have any ideas, let me know!

    • Andrew Draper

      I’m older than you :) , there’s still plenty of time and if I could offer any advice, “jump”. If you don’t think you’ve got what it takes to go alone, find local startup events and start socializing, developers are a hot commodity in the startup world, with an open mind, I’m sure you’ll find something awesome quickly.

      I got lucky early on by being laid off and “forced” into working for myself, I also got a mortgage shortly before I knew I was going to be laid off – there’s no better motivation to hustle than having bills to pay!

  • http://twitter.com/kristopherwong Kristopher Wong

    @twitter-15493008:disqus fully understand. I think that life is too short and you need to follow your passions where ever they may take you.  I am also glad you wrote this to encourage other people that don’t have their heart in the game to pull out or cause more damage than good.  I am thankful that our company has people fully commit; however, realize that this day may come.

    Good luck on your future endeavor. Look forward to what you put out next.

    • Andrew Draper

      Thanks Kris, hopefully you won’t have to wait too long for what I do next!

  • Wei Yang

    It really wouldn’t surprise me if a lot of entrepreneurs have this problem. Many of the serial entrepreneurs I know build companies to solve problems that look good on paper – but the problems they tackle aren’t necessarily problems they personally need solving. Most of these startups end up failing because the founders simply don’t understand the whole problem or the chores of running the startup get boring after awhile and it’s not growing as fast as they want it to.

    For your discovery phase, I recommend finding something that irks you personally and see if you can solve your own problem.

    • Andrew Draper

      Thanks Wei, Definitely agree, and is completely inline with other advice I’ve received.

  • http://couchable.co Tyler Herman

    Nice to hear your story and I’m sure if you could do it once, you can do it again. Keep at it.

    • http://twitter.com/andrewdraper andrew draper

      Thanks Tyler, that’s the premise I’m trying to stick to :)

  • http://twitter.com/no_fear_inc Mario Y. Peshev

    I’ve had a similar experience twice last year – had to leave a startup working like 60h/w for more than a year and rejecting a place in a startup at the very beginning when investors were ready and everything was all set. Pretty tough both times, I still keep asking myself “where would I be if I hadn’t done that” but then I know I’ve started on a fabulous project, can sleep more, do more brainstorming and working with people who really understand and can collaborate.

    One of the hardest things I still learn to do is saying “No” to things. Often it’s too late when I manage to say it or I’m already stuck too deep for that.

  • Peter

    Great post. Takes guts! Especially since ManPacks is such a great service. I’m a customer. Thanks for making something worthwhile and I look forward to your next dent to make life easier. -Pete

  • http://twitter.com/Sterner Christian Sterner

    Great post, but only viable if founders have a Ken (ie…the guy that will ensure your worst nightmares don’t come true if you leave). Without those people, there is not such thing as successful companies, unless the company you are leaving is already so much bigger than your contributions that your absence doesn’t matter.

    • http://twitter.com/andrewdraper andrew draper

      I’m not sure I agree, the story may have ended differently but before making that phone call I had to be sure I was ok with whatever outcome came about—even if it meant the worst.

  • http://twitter.com/KatrinaCF KatrinaCF

    Andrew, thanks for the honest post. It’s a great read, and something few founders/entrepreurs speak about. No doubt you’ve got other plans brewing, but meanwhile, this was a breath of fresh air to read.

  • http://quoperative.com Steve Palmer

    Hey Andrew, great post! That’s certainly one side of the entrepreneur game that few folks seem to talk about… thanks for sharing.

  • http://twitter.com/tackaberry brett tackaberry

    Hey Andrew. Thanks for posting. Its not always easy to share. I know what you’re talking about. I recently left 76, a company I co-founded. I stayed for 10 years, and while there is no regret for that time, I am certainly an advocate of making quick decisions. If you know something is not in alignment, fix it or leave it. Anyways, congrats on the successful brand and best of luck in your next endeavours.

    • http://twitter.com/andrewdraper andrew draper

      Thanks Brett! Didn’t realize you’d left 76—best of luck to you too!

  • http://iamanecessaryevil.com/ Aurelien Leftick

    Thanks for not only having the courage of making such a tough decision but also sharing it. 

  • http://iamanecessaryevil.com/ Aurelien Leftick

    Thanks for not only having the courage of making such a tough decision but also sharing it. 

  • http://www.techhustlers.com/ MatchLites

    Freaking awesome post about stuff that I always try and get my interviewees to admit so that others can breath a sigh of relief. I quit my job in education two years ago because I was dying inside of unhappiness. A year later, my first company was acquired and I have never in my life been more happy. I am not banking in money yet, but hell F’ freaking money if you are not even close to being happy! Happiness is where it’s at bruh :) Thanks Andrew for being real and we would love to have you on our show bro to share your life story.

  • http://twitter.com/CJBeaudoin Chris Beaudoin

    Hey Andrew, great post. It’s awesome that you were able to go through that transition the way you did and share your experience with the rest of us. 

    You’ve got balls. :)

  • Alex Commons

    Thanks for sharing your insight into what I’m sure was a very difficult decision. This is something I’m sure every entrepreneur goes through at least once.

  • girishrao35

    Thanks for the story. Takes courage to do it and then share it with the world! How did your investors take the news? Do you feel your relationships with investors (those who invested and those you are acquainted with) has changed at all?

    Will keep an eye out for your next big thing! :)

  • http://www.facebook.com/scott.wadden Scott Wadden

    Testing.. never mind me.

  • http://twitter.com/cornett Larry Cornett

    It takes courage to leave the security of a 9-5 job and start your own company. It takes even more courage (and wisdom) to admit when it is time to move on from your own startup. I think every founder has many moments of doubt. What you have highlighted here is the value in recognizing the difference between the usual doubts (that you must just push through) and knowing when you no longer have the passion to really drive that startup forward. I wish you the best with your next venture!