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    Entries in doubt (2)


    Unsatisfied ≠ Ungrateful

    (Originally published Jan. 2014 over on Medium)

    Bidding adieu to another holiday season, I was struck recently by a series of conversations I had with friends and family, both young and old. They all centered on the usual exchanges of how everyone was doing and what their plans for the future might be. When it came my turn to sound off on my current status and hopes and dreams for the future, the upshot was remarkably the same — “You should be more grateful for what you have.”

    Now aside from the fact that every single discussion centered on the general well-being of my family (wife and two kids), and I prefaced each answer with my thankfulness for their health and happiness, I answered as honestly as possible with regard to the hoping/dreaming bit.

    “…at least you don’t have to deal with traffic.”

    While I expected this candor to be met with the usual well-wishing and encouragement, the most common refrains went something like, “…at least you don’t have to deal with traffic,” or “…at least you’ve got a good marriage”, or “…at least you have a job.” At this point, I’d like to pause and advocate 100% for daily meditation on those people and circumstances you’re thankful for. In my case, I do this as part of my morning routine and can say confidently that it is a major reason for my success in the areas of life continually referenced by those close friends and relations above. With that said, I’m still left wondering why some of the greatest people I know seemed so put off when I told them that I was unsatisfied with my current station. Don’t we all continually strive to achieve our goals? Isn’t that what so many dogmatic inspirational posters plastered across the waiting rooms and classrooms of our youth told us to do? It’s the journey, not the destination, right?

    All jokes and memes notwithstanding, I think the answer is wholeheartedly yes. Never be satisfied so much to the point that treading water seems like a nice place to end up. I’m all for continual reflection on the gifts our lives provide, but not at the expense of ambition and aspirations. Remaining curious and open to all avenues should be celebrated. “What if?” is a powerful motivator.

    Curiosity may have killed the cat, but it also crowns the kings.


    You're Doing It Wrong - Of Those Damned Long Entrepreneurial Odds


    If you read my stuff regularly (aka as often as I post) and/or follow my other social feeds, you might get the impression I'm all "rah-rah," all the time. I'm not going to lie, that's calculated. Not so much that I feel positive messages are always the best way forward, but more so because that's the mindset I strive for. Anyone can sell sunshine, but if you believe it, you might as well write it that way. So there you go.

     Anyone can sell sunshine, but if you believe it, you might as well write it that way.

    To the contrary, this post is why my team and I shouldn't win, why we won't become something, why we dream only pipery, why everyone loves to hate...and why they feel righteous in doing so. I'm doing it wrong. This is as much a pep talk to any audience as is it to myself, while indulging the critics, so bear with me.

    Here's a list of reasons why we won't succeed: 

  • Non-technical?   Check.
  • Loads of School Debt?  Check.
  • Mortgage?   Check.
  • Kids?   Check.
  • Rural?   Check.
  • Noob Entrepreneur?  Check.
  • I tumble these bullets in various permutations around in my head constantly. None of the combinations amount to any more than your likely reaction to the above - "Totally screwed, bro," followed closely by, "...but good for you for trying."

    The fun part about any of this analysis is the challenge of converting each one of those liabilities to assets. Let's examine.

    I'll be the first to admit that being a "non-technical" founder is a will my other two non-technicals. Shakespeare put our situation aptly when he said:

    How shall your houseless heads and unfed sides,
    Your looped and windowed raggedness, defend you
    From seasons such as these?

    In this case, the "seasons" as I see them, are our rapidly approaching future scenarios without a relevant tech "house" to speak of. The non-technical bit is an easy fix...if you have the right mix. While my partners and I may not have the programming chops to pass 21st century muster just yet, believe me, that day is coming. I've told others that time is my only currency anymore. This has never been truer for me or my co-founders. Do I really think that all the founders will gain some significant proficiency in hard coding? No. Do I think we should all strive for that? Yes - if only to facilitate better design conversations and make better hires down the road. If this ignorance is in any way an asset at this point, then I would tell you that the beauty is in not knowing what isn't possible. (But that still feels like a cop out. Learn to code).

    Would I recommend that any ambitious soul seek to make his or her dent in the universe before they accrue mounds of relatively useless school debt and a mortgage? Of course.

    As far as the debt situation goes, I can't really creatively deal with the intractable nature of it at this point. This is, and always will be a severe liablilty to any would-be entrepreneur. Would I recommend that any ambitious soul seek to make his or her dent in the universe before they accrue mounds of relatively useless school debt and a mortgage? Of course. Anyone who says otherwise is an idiot. But, I would heartily encourage any in my situation to still consider the entrepreneurial path - it is the only way forward. And to those without the hinderance of any money owed, consider how profoundly any and all extra responsibilities will factor into your life before you embark, to give yourself the best shot at success before jumping in.

    Kids are awesome. At the risk of sounding cliche, my life took a dramatic turn for the best with the birth of our first child. I know myself and my goals infinitely better now, than I ever would have without my children. Not to say they are a necessity, but do not doubt they are generally transformative.

    Rural America is becoming less so. I don't mean that people are flocking to settle in smaller communities like mine (though I think that's coming), but I do mean that geography has never mattered less to the world of business...and the "hicks" are catching on. Having your cake and eating it too no longer seems like such an outsized request. Certainly there are more restraints on capital investment and talent for startups in a place like Montana, but that is only a temporary situation if our various economic development groups can help it. A number of successful natives (adopted and othewise) from other areas of the country have a vested interest in seeing Montana succeed in the new business sandbox of the 21st century. Quality of life begets quality of talent.

     You will and should live or die by the fires of your market.

    And so we come to the green beginner piece of this critique. Everyone has to start somewhere, right? A thousand more placations where that came from still manage to engender exactly 0% goodwill in the business market. And why should they? You will and should live or die by the fires of your market. You and your team will be salted just the same as any who have tread this path before you, and you will learn from it. And you will benefit from it. And this is pretty much the only way to truly experience the world in my opinion. Sure, nothing beats experience, but I think this goes beyond that. I think that nothing beats the soulful passionate chase through a no-holds-barred gauntlet of real world pwnage that rightfully awaits those who undertake it. It's sort of like those old commercials for the Marines (no offense intended in the analogy, just illustrating a point). If you think you've got what it takes, then go for it. Why the hell would you let anyone pretend that inexperience is a valid excuse for not trying? 

    Any good entrepreneur knows when to cut the bullshit. Consider this missive one of those moments, and consider this moment one of my sign offs.

    Good luck out there.