4 Important Lessons I Learned From Jumping into Entrepreneurship Head-On

A lot of people start feeling super-awkward about themselves when they contemplate starting their own business…y’know, a tingley-feeling of “should I really be doing this?”  ”Will I uber-fail and people will think I’m an idiot?”

I worried about all of those things…but decided “to hell with it, YOLO!”, and gave up the idea of pursuing a “normal” career; opting to jump head-first into entrepreneurship after I graduated from college.

(I promise I don’t say YOLO in real life).

And I sit here 10 months later…reflecting back to all of the things I’ve done…

…some of them have been ingenious…

…most of them have been downright stupid, and can only be chalked up to a “learning experience”

So I decided to take my experiences…the good, the bad, and the shitty…and distill them into this super-long, heart-spilling missive.

TLDR??..if you’re serious about starting on your own, and don’t want to spend months making mistakes, take this opportunity to learn from my mistakes, and do better yourself:

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How 1 Poisonous Mistake Almost Destroyed Everything I’d Worked For (and how fixing it put my startups back on track)

Have you ever had the feeling that there was something horribly wrong, but you couldn’t really put your finger on what it was?  That’s how I felt about my startups not too long ago.

Have you had a feeling like that that grew day after day…becoming more and more painful…until one day, you were so upset that you wanted to quit it all…all without really knowing what the problem was in the first place?

At one point, that was me and how I felt about my chosen career path in entrepreneurship.

Things were a complete mess.  None of my startup ventures were going the way I wanted them to.  I sort of dabbled in a couple different ventures, only to have those go nowhere too.  In the back of my mind, a worry started to grow:

R.C., what the hell is your problem?  Why are you so bad at entrepreneurship?  You’ve wanted to do this your whole life, yet you seem to be failing completely.  No sales.  No traction…at least not as much as there should be.  Maybe you should just quit.

Frustration was my closest friend.

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How I failed 54 times and wasted 400 hours before learning 1 simple game-changing startup lesson

How would you feel if you spent 400 hours trying to do something 54 times…only to completely fail and find yourself back at square 1?

Welcome to my world, circa January – May 2012.

I promise you I’m not here to complain…actually, I’m incredibly grateful for the experience.

It taught me something that will remain with me for the rest of my life…and something that helps me start awesome companies, and write awesome stuff here for you to learn from.

I want you to learn this lesson now, before you waste time and get frustrated.

I failed 54 times–and wasted 400 hours–because I failed to grasp the most fundamental element of business.

But when I learned my lesson and saw how one simple tweak could completely change my chances for success, I knew I’d found a winner…

And I want to share it with you.

So gather ’round the campfire, and settle in to hear a story that completely changed my outlook on life: [click to continue…]

The Failures of an Entrepreneur

Today, we celebrate the launch of Decoding Startups, a blog designed to take you from excuses to launch…

…to not only convince you that the excuses you’ve made that hold you back from embracing entrepreneurship are silly, counterprouctive and wrong…

…but more importantly, to teach you systems and skillsets that make you a master entrepreneur.

Systems and skillsets that take away a significant amount of the risk associated with starting a venture; that drastically increase the likelihood of your success.

We celebrate today’s launch…by talking about my failures.

Why talk about my failures?

Failure taught me everything that I teach you today.

Do you ever notice how most bloggers who write about entrepreneurship, personal finance and careers try so hard to come across “perfect”?  Like they’re so smart and wonderful that they had all of this stuff figured out when they started, and their life has been nothing but an impossible-sounding stream of success?

The reason I hate blogs like that is it makes success seem unattainable…as if only the most intelligent, most herculean of us all could accomplish wonderful things in our lives.  Because these authors don’t talk about their own shortcomings and the failure-laden path that led to their ultimate success, they miss a huge opportunity to teach others; and more importantly, they miss the chance to teach others that success is attainable.

All of the entrepreneurship progress I’ve made today came from months of screwing up, and years of being too afraid to even try.

Don’t think I’m anything wonderful, because I’m not; the only difference between me and most people is that I’ve actually taken the time to try, and to learn.

That’s the only difference.  I’m not smarter than you.  I definitely haven’t come up with better business ideas than you.  And I’m sure as hell not richer than you are.

None of those things matter.  What did matter was the one thing I did differently:

There’s no substitute to learning through trying and failing…

Even if you read every article on my blog, you’d be nowhere near closer to success in entrepreneurship if you don’t actually try to do it.

Why do you think I’m so adamant about crushing the excuses that hold us back?  Because the best way to learn about starting a business…is to try and start a business.

This doesn’t come through luck.

 How I failed before, what I learned, and what you can learn too:

This week, I’ll release 2 articles talking about ambitious undertakings that I blew (or seriously slowed down), and the lessons I learned. I hope that talking intimately about my shortcomings will prove to you–once and for all–that success comes from persistence…not luck, not having lots of money, and certainly not from having an Ivy League diploma hanging on the wall:

  • How I failed 54 times before learning this one simple lesson
  • How disorganization cost me months of time despite having a good idea and great progress

Have you tried–and failed–at entrepreneurship?  In the comments below, let us know what happened, and what you learned.

(Photo credit By Damian Morys from New York City, United States ([1]  Uploaded by MB-one) [CC-BY-2.0 (], via Wikimedia Commons)