12 Entrepreneurial Epiphanies & Lessons Learned


#1) My (First) Entrepreneurial Epiphany  #IamNOTaCEO 

Most entrepreneurs / startup founders will put “CEO” on their first business card when starting a company. And I was no different back when I started my first company. But I quickly (eventually) realized some things that would have a dramatic impact on my entrepreneurial career — past, present and future!
~ I REALIZED... that being a CEO (or at least a successful one) requires a very unique set of skills — which I believe the majority of entrepreneurs / startup founders do NOT actually (inherently) possess.
~ I REALIZED... that the following are actually three VERY DIFFERENT things:

   A. Starting a business
   B. Growing that business into a company
   C. Successfully running that company

   (...and that A. B. and C. can often require three very different mindsets, skill sets, personality types, etc., particularly for the CEO - or at least a successful one.)

   A. what my strengths are (the FEW things I'm GREAT at) and what my weaknesses are (the MANY things I SUCK at!),
   B. how my brain works and how some of my personality traits impact me as an entrepreneur,
   C. and for which part(s) of the startup process I’m best-suited (and at which parts I’m most likely to struggle!)

NOTE: The fact that many (most?) startup founders never realize/accept some/all of the above -- due to ego? lack of self-awareness? or just never really stopping to think about it (until now?)? -- is one of several reasons why I think there is an unnecessarily high failure rate for startups (~99% Will Fail!). But I’ll get into that and more thoughts/theories in future columns...

#2) I'M FIRED?!?  #BestDecisionEVER

Back in 2007, I had a “company” (a term I use loosely, hence the quotes) which was a collection of viral “Humor Hotlines” (the first/biggest of which was “The Rejection Hotline®”) which were collectively reaching / entertaining / engaging MILLIONS of people and receiving huge amounts of media coverage; yet I had (half-jokingly) dubbed myself “America’s Worst Entrepreneur” because, despite the success/growth on the consumer-facing/product side, we were still losing money on the business side...
CNN-Live-RejectionHotline-2002[Even CNN thought we were making lots of money! But despite receiving MILLIONS of phone calls and tons of media coverage, we weren’t profitable until I realized: “I am NOT a CEO” (and subsequently fired myself as CEO of my own company)]

So, after much soul-searching and internal debate, I decided to “fire myself” as CEO of my own company. I brought in a business partner to be the new CEO, to run/grow the company, to handle the parts of the business that I wasn’t particularly good at (or excited about), allowing me to focus on the parts of the business that I was best at (the content, the creative, the ideas, the vision, the strategy, etc.).

IamNOTaCEO.comThat realization that “I am NOT a CEO” was absolutely the catalyst for the success of our startup! Within 6 months of replacing myself as CEO, we had raised a million dollars in funding. Within 6 months of the funding, we were a profitable 7-figure company — after YEARS without any significant revenue! 

In conclusion (as I am optimistically hoping that someone is still reading at this point), my “I am NOT a CEO” lesson is one that I hope to encourage other entrepreneurs to seriously consider for themselves; and it is the backbone for how I plan to write the next chapter in my startup career by embracing both my strengths (as an idea guy, a vision guy, a startup-STARTER) and my weaknesses (execution, operations, sales, getting distracted in the middle of a

#3) Strengths & Weaknesses  #SelfAwareness 

With 15 years experience in startups (including: VC-funded, angel-funded, bootstrapped... acquisitions, asset-sales, dissolutions... successes, failures...), I've seen/learned A LOT - not only about the startup world in general, but about myself as an entrepreneur. I have become keenly aware of my (few) entrepreneurial strengths... as well as my (many) entrepreneurial weaknesses! 

WARNING to Future Employees & Partners!

  • I SUCK at organization.
  • I SUCK at execution.
  • I SUCK at operations.
  • I SUCK at follow-up.
  • I SUCK at follow-through.
  • I SUCK at presenting / pitching / selling.
  • I SUCK at networking / schmoozing.
  • I SUCK at employee-management.
  • I SUCK at money-management.
  • I SUCK at project-management.
  • I SUCK at time-management.
  • I SUCK at stress-management.

In response to the list above, many will say "Well, then clearly this guy doesn't have what it takes to be a successful entrepreneur - because he literally just named ALMOST EVERY IMPORTANT CRITERIA for being a successful entrepreneur!" 

I get it. And I completely respect that opinion. Heck, it's exactly what I would say if the person we were talking about was almost anybody/everybody else!

But I would argue that I actually just listed criteria more applicable to being a successful CEO or COO... and that it is possible (albeit more challenging) to be be a successful FOUNDER and/or a successful ENTREPRENEUR even if you are NOT the CEO/COO type... particularly if you are self-aware enough to truly understand your strengths/weaknesses and create the projects and programs necessary to attract execution partners with complementary skill-sets!

Soooo, I listed above some of the MANY things I SUCK at... There are, however, a FEW things that I'm pretty f*ckin' great at...

  • I'm an innovative thinker, an imaginative re-thinker, an inventive problem-solver, and a great strategy/vision/intuition guy. My (relatively unique) experience/expertise is creating, recognizing, and/or evaluating concepts and content with the viral potential to resonate with large/diverse audiences, intuitively recognizing many factors (the art, science, psychology, math, etc.) impacting virality and differentiating an “idea” from what I call an "IDEA+++"
ViralWhatever.com IDEA+++
  • I was at my creative best (numerous viral ventures, engaging millions of people, huge amounts of viral buzz and national media coverage) back when I was embracing my “Entrepreneurial A.D.D.”, working on many ideas/projects simultaneously. I intend to get back to that in 2017 and beyond - IF I can successfully attract the right execution partners and assemble teams of entrepreneurs with complementary skills sets...

  • Will ALL my ideas/ventures be successful or go viral? Of course not. But I’ve achieved viral traction with ~12.5% of all creative concepts/content I’ve launched over the years; so, with the quantity / quality of ideas, products, content, startups I plan to launch (and StartupWhatever.com strategies of shared resources, economies of scale, and the cross-promotional “Network Effect” of it all!) - and *IF* I’m able to find some great execution partners - I'm extremely excited and optimistic about our plan for 2017 AND BEYOND!

[COMING SOON]  #4)  From a SMALL JOKE to a MILLION-DOLLAR STARTUP (The Rejection Hotline, Humor Hotlines, and RH Brands... #MyStartupStory)

(column coming soon)

[COMING SOON]  #5)  The Stomach-Punch Feeling of Losing 4 Million Dollars...  (full column soon)

(column coming soon)

[COMING SOON]  #6)  My Battle With Burnout...  (full column soon)

(column coming soon)

[COMING SOON]  #7)  My ENTP / INTP Epiphanies...   (full column soon)

(column coming soon)

[COMING SOON]  #8)  My ADD Epiphany - PART 1 - It's a CURSE!  (full column soon)  

I had "known" for many years that I had ADD (Attention Deficit Disorder)... but I didn't start to truly understand it - and how it affects my brain (and my life!) - until very recently.  I had always assumed - as I think most people do - that ADD was just difficulty paying attention, getting distracted easily, and being a little scatter-brained, absent-minded, and/or constantly bouncing from one thought/idea to the next... I didn't start to truly understand my ADD until I read these blog posts by an entrepreneur/VC named Mark Suster:




(full column coming soon)

[COMING SOON]  #9)  My ADD Epiphany - PART 2 - Curse or Gift?  (full column soon)  

(column coming soon)

[COMING SOON]  #10)  Starter? YES! Finisher? NO!  ...  80% Done --> 80% D --> 80 D --> 80D --> I am 80D --> Iam80D.com = IamADD.com (coming soon)

Starter? YES! Finisher? NO! ... 80% Done - then I lose interest and my brain gets hyper-focused on a new challenge... 80% Done? --> 80% D --> 80 D --> I am 80 D --> Iam80D.com / IamADD.com 

(full column coming soon)

[COMING SOON]  #11)  An Open (Thank You) Letter to Mark Suster - which (ironically? coincidentally? embarrassingly?) has sat on my laptop, 80% DONE, for a year... (coming soon)

(column coming soon)

#12)  Speaking of my Entrepreneurial ADD... WTF have I been doing for the last 3 YEARS?!?