Published in


THOUGHTS & THEORIES (re: Problems/Pitfalls & Frequent Founder Failure Factors)

From our analysis 500 FAILED FOUNDERS!!

Contact to discuss, debate, whatever… [I have no interest in starting my own podcast, but I’d love to discuss/debate all this (and more!) on YOUR podcast!]


Persistently-Pervasive PROBLEMS & Prominent PITFALLS:

1) Lack of Self-Awareness in Founders…

Most people have a GREAT level of self-awareness when it comes to the ability to play the piano or pilot an airplane; but many people (particularly entrepreneurs) have a terrible level of self-awareness when it comes to evaluating their own ideas, vision, strategy, likelihood of product-market-fit and/or overall probability of startup success… [To Be Continued]

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

[Preview] Startups are HARD. But they are much HARDER with the wrong people working on the wrong things! Why would you think you’ll be the ~1% to succeed if you don’t have GREAT people working on what they’re GREAT at?! [To Be Continued]
P.S. Yes, of course you have to wear a lot of hats at the beginning… and finding GREAT Co-Founders is very difficult — but some of the things we’re “ReThinking” are some creative ways to make that search for GREAT partners a bit easier!

P.S. 2.5?? A combination of #1 & #2 (because it’s difficult to put people — especially ourselves! — in the best position to succeed if a lack of self-awareness has us in denial about how good we are at what), please ask me about some experiments I’ve done while speaking at conferences or running workshops. SPOILER ALERT: In a room of 100 entrepreneurs, when asked (anonymously) to rate themselves (honestly) in comparison to the rest of the room, in defiance of basic math, EVERYONE is “ABOVE AVERAGE” in most categories — and HALF are in the “TOP 10%” (especially in areas like intelligence, creativity, strategic-thinking)

3) Problems Stemming from WORDS & DEFINITIONS:

What is a Startup?? What makes you an Entrepreneur??
[Spoiler Alert: There are very few (if any) blogs, podcasts, advice, or “best-practices” that are intended for BOTH: “Startup A” (a pair of bootstrapping co-founders, working from co-working “hot desks”, on their pre-launch MVP) AND “Startup B” (a 30-employee B2B SaaS company with 7-figure ARR, raising an 8-figure Series B round, at a 9-figure valuation, with aspirations of being a billion-dollar unicorn).
Are they both startups?? Yeah, I guess so — but in the same sense that an ice cube and the Atlantic Ocean are both water? [To Be Continued]


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 be applied to EVERYONE in EVERY SITUATION.

4) “Success” vs. “Failure” & FUQ! (Frequently UN-asked Questions)

Spoiler Alert: It’s NOT as obvious a distinction as you’d think!
P.S. Semi-Related Question:
A) aim for ~$25M, but hit $2.5M?
B) aim for $250K, but hit $2.5M?
Spoiler Alert: A = $2.5M and B = $2.5M but A ≠ B
(wait, what?) — [Full Column Soon]

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

5) “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]

6) Why does every Entrepreneurship class or Startup Weekend or Hackathon orHow To Build A Startup” class always start with: “STEP 1: Everyone come up with an idea.”
[P.S.] I totally understand if it’s just for fun or learning purposes — BUT, if the goal is success, it is teaching a very inefficient/ineffective/sub-optimal methodology… … [To Be Continued]

7) Yes, of course it is “Theoretically Possible” for a successful startup to come from anywhere/anyone… but it is much more “Statistically Probable” when you have GREAT people doing the things they are GREAT at… And, just like coding and graphic design are skills (that some people are significantly better at than others), different types of THINKING are also skills (that some are significantly better at than others!) — creative-thinking, strategic-thinking, critical-thinking… and ideation (idea creation & evaluation!)

8a) Not all “ideas” are equal
8b) Not all ideas are created equal(LY)
*P.S. That “(ly)” is very intentional — as we believe both:
a) “that there is a wide range in the quality of ideas (obviously?)”
but also
b) “that the processes of creating those ideas (and the skill/talent/ability levels of the idea creators)” can often be as different as apples and orangutans!

* Note: Replace “Viral potential” (above) with “Product-Market-Fit” for when virality is not necessarily a goal.

8B) For those that say “Ideas are Shit (& Execution is Everything)”, I would love to have a short conversation with you about this! In lieu of that, I would love for you to consider adjusting it to “MOST Ideas are Shit (& Execution is Extremely Important)”… because, I assure you, MOST of ANYTHING would have a reputation for being shit (coding? design? music?) if EVERYONE was encouraged to continue doing it with no regard for talent or skill… [Please ask me about this if we ever meet — it’s one of my favorite topics to discuss!]

9) “What are you GREAT at?!? Figure it out and DO MORE of THAT!!!”

[Several sports examples/analogies lessons — Coming Soon] TEASERS:
A) Michael Jordan: Basketball career vs. Baseball career…
B) Why it doesn’t matter if Bill Belichick can’t throw or catch — or that Tom Brady is slow and sucks at blocking and tackling… [full column soon]

10) Optimistic vs. Pessimistic? Positive vs. Negative? [WAIT! What about Realistic?! and Objective?!]

… and why those “Never Give Up!” and “Winners Never Quit!” motivators can potentially do more harm than good! [full column soon]
In Sports, “NEVER Give Up” is often MINUTES… In the real world, “NEVER Give Up” is… F***ing FOREVER!?!

10b) “Trust your gut!” Two quick thoughts (full column is elsewhere) — 1) If you make decisions with anything other than your brain, we can’t be friends. Making decisions with your stomach makes as much sense as making decisions with your left elbow or the pinky toe on your right foot. And, please, visualize this:

Based on the normal digestion period, a decision coming from your gut is, quite literally, the same thing as pulling shit out of your ass (just a few hours later based on gut-to-ass travel time via normal digestion).

But, more seriously — trusting your gut, your instincts, or “just a hunch” makes for an amazing story if, If, IF it ends up working out — but (I assure you!) “trusting your gut” has backfired just as often (if not significantly more often)… you just don’t hear stories starting with “I trusted my gut / my instincts / had a hunch…” when things go sideways.

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

Successful entrepreneurs are often characterized as “Risk-Takers” — and we all love those success stories of BIG RISK & BIG REWARD! But…
A) is the Success BECAUSE of the Risk?
what about the 99% of UNsuccessful Entrepreneurs? weren’t they Risk-Takers too??
C) but Forbes doesn’t often cover the ~99% where Big Risk is followed by Big Failure… so the natural tendency for Startups/Entrepreneurs to Succeed Publicly / Fail Privately = Causation/Correlation Confusion!!
[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

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

Try to remember:
For every AWESOME (inspirational!) story of success that you hear, remember there are HUNDREDS (if not thousands?) of AWFUL (depressing!) stories of failure that you’ll never hear…

13) Funding Frustrations?

Spoiler Alert:
MOST investments (in pre-revenue startups) are BAD investments!

14) If ~99% of startups FAIL, yet ~100% of entrepreneurs BELIEVE they’ll be the ~1% to succeed, then YOUR Assumptions, Beliefs, Confidence [#ABC?] — about YOUR Startup — can (unfortunately) NOT be taken as OBJECTIVE or reliable (because EVERY ENTREPRENEUR feels that way about THEIR STARTUP!)

So, the honest/harsh (objective!) reality is that you (and your startup) are NOT A SMART BET (for an investor — or even for yourself to make the All-In / Full-Time leap!) — UNLESS or UNTIL you have some RELIABLE OBJECTIVE INDICATOR(S) of…

Honorable Mentions:
- “Been There / Done That” — Prior Startup SUCCESS (not just experience)
- Joining a TOP Incubator/Accelerator program with a proven track-record of success (i.e. Y-Combinator, TechStars, etc.)
- [NOTE: I’m definitely open to adding more if anyone has additional thoughts! —]
P.S. A lot of the above makes for good discussion/debate for PODCAST content — But, alas, I will likely never get around to starting my own Podcast… Sooo, if you want to invite me on YOUR Podcast to discuss (or debate!) any of our Thoughts/Theories or Ideas for Improvement, please do!
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 common Problems & Pitfalls (and #StatusQuoBias)… Because simply repeating all the same practices and processes of countless failed startups/entrepreneurs before us (and yet somehow hoping for different/better results?) sounds pretty close to Einstein’s(?) definition of INSANITY!
Sorry, just adding another version of this image again so we can set it as the default image to show up in previews



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store