10+ THOUGHTS & THEORIES (Pertaining to Problems & Pitfalls)


Our “INQUISITIVE 5-YEAR-OLD” Methodology
“Why did your startup fail?”
We ran out of money… 
“But, WHY?” 
Well, mostly because we couldn’t convince investors to fund us… 
“But, WHY?”
 Well, probably because we never found Product-Market-Fit… 
“But, WHY?”
Well, I guess some of our core assumptions were wrong…
“But, WHY?”
… Well, maybe we were blinded by our excitement, wishful-thinking, overly-optimistic assumptions, and…

Pervasive PROBLEMS & Prominent PITFALLS…

(In No Particular Order)

1) Mis-Matched Skill-Sets Among Co-Founders…

[full column soon]

2) Lack of Self-Awareness in Founders…

[Preview] Most people have a pretty good level of self-awareness when it comes to their abilities to play the piano or pilot an airplane — or how good they are at golf or ice-skating… But I believe many (most?) entrepreneurs have a terrible level of self-awareness — particularly when it comes to their ideas, vision, strategy… and overall likelihood of their startup’s success! … [To Be Continued]

3) Many Problems Stemming from WORDS & DEFINITIONS:

What is a Startup?? 
What makes you an Entrepreneur?? 
And, “Best Practices” for whom??
Full Column Here)

A caveat to everything I write is that EVERY STARTUP is different, EVERY ENTREPRENEUR is unique, and there is NOTHING (said/written by me — or Tim Ferris or Gary V. or whomever!) that can possibly apply to EVERYONE in EVERY SITUATION!

3B) “Success” vs. “Failure”

[Spoiler Alert: It’s NOT as obvious a distinction as you’d think!]

3C) Would You Rather: A) aim for ~$25M, but hit $2.5M? -or- B) aim for $250K, but hit $2.5M?

Spoiler Alert: A = $2.5M and B = $2.5M but A ≠ B — (wait, what?)

A Plethora of Problems & Pitfalls Pertaining to: “IDEAS!”

4) “There’s no such thing as a bad [xxxx]
Wait… What?? SERIOUSLY?!? If you wouldn’t say that about a “logo”, a “website”, an “app”, a “sales call”, or an “investor pitch”, then WHY do we say it about “IDEAS”?!? [To Be Continued]
5) “Everyone think of an idea…” 
That’s fine in certain situations — particularly for children! Just like every kid takes science classes (even though very few will become scientists) or how every kid is encouraged to play sports (even though a smaller number of kids are good enough to play High School sports, even fewer are great enough to play Collegiate sports, and how many people do you know who are talented enough to be a professional athlete and make it their career?!)… [To Be Continued]
6) Why (the F!) does every Entrepreneurship class or Startup Weekend or Hackathon or “How To Build A Startup” class or blog starts with something like: “STEP 1: Come up with an Idea.” 
[NOTE: If it’s solely for the experience / learning opportunity, then I guess I’m ok with it. But when it’s “FOR REAL”, a startup that you actually want to succeed, that you want others to invest in, that you want to dedicate your own time/money/life to?? Well, the “everybody think of an idea” mindset is, in my opinion, a big part of why ~99% of startups fail!]
7) Not all “ideas” are created equal(ly?)… The difference between a regular “idea” and what ViralWhatever.com has dubbed an “IDEA+++”
* Note: Replace “Viral” (above) with “Product-Market-Fit” for when virality is not a goal (like B2B SaaS)

8) “What are you F***ING GREAT at?!? DO MORE OF THAT!!!”

[Several sports examples/analogies — Coming Soon] TEASERS: 
A) Michael Jordan: Basketball career vs. Baseball career… 
B) It doesn’t matter if Bill Belichick sucks at passing, catching, running, blocking, or tackling… [full column soon]

9) Optimistic vs. Realistic

… and why those “Never Give Up!” and “Winners Never Quit!” motivators can actually do more harm than good! [full column soon]

10) RISK-TAKING: To Celebrate? Or To Mitigate?

[Full Column]

I always see photos of sad people sitting in front of brick walls. I can only conclude that brick walls must make people sad. #CorrelationVsCausation

11) The problems/pitfalls of using OUTLIERS as benchmarks…

A) Remember learning about Correlation vs. Causation? If a successful entrepreneur did [whatever] and had success, be sure to consider whether that was a CAUSE of the success — or if perhaps 99% of entrepreneurs who tried that same thing might fail anyway? (To Be Continued)

B) For every AWESOME inspirational story of success that you hear, remember there are potentially hundreds of HORRIBLE failure stories you’ll never hear… (To Be Continued)

12) Funding Frustrations?

Spoiler Alert 1: MOST investments are BAD investments! 
Spoiler Alert 2: Friends & Family Funding = Founders Frequently Failing
(coming soon)

13a) YOUR confidence, YOUR beliefs, YOUR assumptions — can (unfortunately) NOT be taken as OBJECTIVE (about YOUR startup — because EVERY ENTREPRENEUR feels that strongly about THEIR STARTUP!) so they are simply not objectively relevant if investors (or you, yourself!) are attempting to evaluate your startup’s success odds — OBJECTIVELY! 
(Full Column)


(That a Startup Has Better-Than-Average Chances of Success)

1. Product-Market Fit (proven, not based on your assumptions)
2. Viral Traction / Growth
3. Repeatable Customer-Acquisition Model
4. Profits (or at least steady or growing revenue)
 — 5. Funding. (Only for how it will allow you to grow — 
 — NOT because it’s truly as objectively validating as 1–4)

(Click for More — Full Column)


14) Based on all of the above, we actually advise — admittedly, against common advice from many successful startup veterans — that you probably shouldn’t even quit your job and go All-In / Full-Time, UNLESS/UNTIL you have achieved one of those Five OBJECTIVE INDICATORS. So, we believe the pursuit of those indicators, the testing of your assumptions, hypothesis, your product, getting feedback, etc. should be done in a PART-TIME capacity… (and, yes, we know many startup veterans just rolled their eyes, but please, hear us out!)

Whether your “full-time” job is in Corporate America, already with a startup, or as a full-time student, we’d like to introduce you to the idea of putting “Multiple Eggs in Multiple Baskets” and the many potential benefits of PART-Time “STARTER STARTUPS!”
15) Investors don’t invest in one company; they diversify their portfolio to mitigate risk and increase chances of big wins. We believe that startups / entrepreneurs should consider that too… (MultipleBasketStartups.com)
16) I believe the idea of “you must be all-in / full-time” (on one startup) is not only an over-rated notion, but also somewhat outdated — from a time (just a few years ago!) before the cloud and AWS and WordPress and Shopify and Facebook Ad-Targeting and countless other services making it MUCH easier/faster/cheaper to launch and test MVPs…(www.theSWANstartup.com — Sacrificing Weekends And Nights)

Yes, of course “Startups Are Hard” — but there are things we can do to dramatically increase the current success/fail rates if we start thinking (and re-thinking?) more strategically and identifying / addressing some pervasive problems & prominent pitfalls. Because just blindly repeating all the same practices and processes of countless failed startups/entrepreneurs before you (and yet somehow hoping for different/better results?) is CRAZY!
3 Years of Thinking/Writing/Planning:
IamNOTaCEO.com (Entrepreneurial Epiphanies)
ThoughtsOnStartups.com (Thoughts & Theories)
ReThinkingStartups.com (Improvement Initiatives)
ViralWhatever.com (“We make Sh*t Go Viral” Secret Sauce)
Part-Time “Pursuit of Proof” Premises & Programs:
StarterStartups.com / MultipleBasketStartups.com / theSWANstartup.com
Practicing What We Preach:
18Startups.com / PitchingForPartners.com

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