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How We Secretly Lose Control of Our Startups
Should Kids Follow in Our Founder Footsteps?
The Evolution of Entry Level Workers
Assume Everyone Will Leave in Year One
Stop Listening to Investors
Was Mortgaging My Life Worth it?
What's My Startup Worth in an Acquisition?
When Our Ambition is Our Enemy
Are Startups in a "Silent Recession"?
The 5 Types of Startup Funding
What Is Startup Funding?
Do Founders Deserve Their Profit?
Michelle Glauser on Diversity and Inclusion
The Utter STUPIDITY of "Risking it All"
Committees Are Where Progress Goes to Die
More Money (Really Means) More Problems
Why Most Founders Don't Get Rich
Investors will be Obsolete
Why is a Founder so Hard to Replace?
We Can't Grow by Saying "No"
Do People Really Want Me to Succeed?
Is the Problem the Player or the Coach?
Will Investors Bail Me Out?
The Value of Actually Getting Paid
Why do Founders Suck at Asking for Help?
Wait a Minute before Giving Away Equity
You Only Think You Work Hard
SMALL is the New Big — Embracing Efficiency in the Age of AI
The 9 Best Growth Agencies for Startups
This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding
Never Share Your Net Worth
A Steady Hand in the Middle of the Storm
Risk it All vs Steady Paycheck
How About a Startup that Just Makes Money?
How to Recruit a Rockstar Advisor
Why Having Zero Experience is a Huge Asset
My Competitor Got Funded — Am I Screwed?
The Hidden Treasure of Failed Startups
If It Makes Money, It Makes Sense
Why do VCs Keep Giving Failed Founders Money?
$10K Per Month isn't Just Revenue — It's Life Support
The Ridiculous Spectrum of Investor Feedback
Startup CEOs Aren't Really CEOs
Series A, B, C, D, and E Funding: How It Works
Best Pitch Decks Ever: The Most Successful Fundraising Pitches You Need to Know
When to Raise Funds
Why Aren't Investors Responding to Me?
Should I Regret Not Raising Capital?
Unemployment Cases — Why I LOOOOOVE To Win Them So Much.
How Much to Pay Yourself
Heat-Seeking Missile: WePay’s Journey to Product-Market Fit — Interview with Rich Aberman, Co-Founder of Wepay
The R&D technique for startups: Rip off & Duplicate
Why Some Startups Win.
Chapter #1: First Steps To Validate Your Business Idea
Product Users, Not Ideas, Will Determine Your Startup’s Fate
Drop Your Free Tier
Your Advisors Are Probably Wrong
Growth Isn't Always Good
How to Shut Down Gracefully
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Can Entrepreneurship Be Taught?
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Staying Small While Going Big
Investors are NOT on Our Side of the Table
Who am I Really Competing Against?
Why Can't Founders Replace Themselves?
Actually, We Have Plenty of Time
Quitting vs Letting Go
How Startups Actually Get Bought
What if I'm Building the Wrong Product?
Are Founders Driven by Fear or Greed?
Why I'm Either Working or Feeling Guilty
Startup Financial Assumptions
Why Every Kid Should be a Startup Founder
We Only Have to be Right Once
If a Startup Sinks, Founders Go Down With it
Founder Success: We Need a Strict Definition of Personal Success
Is Quiet Quitting a Problem at Startup Companies?
Founder Exits are Hard Work and Good Fortune, Not "Good Luck"
Finalizing Startup Projections
All Founders are Beloved In Good Times
Our Startup Culture of Entitlement
The Bullshit Case for Raising Capital
How do We Manage Our Founder Flaws?
What If my plan for retirement is "never retire"?
Startup Failure is just One Chapter in Founder Life
6 Similarities between Startup Founders and Pro Athletes
All Founders Make Bad Decisions — and That's OK
Startup Board Negotiations: How do I tell the board I need a new deal?
Founder Sacrifice — At What Point Have I Gone Too Far?
Youth Entrepreneurship: Can Middle Schoolers be Founders?
Living the Founder Legend Isn't so Fun
Why Do VC Funded Startups Love "Fake Growth?"
How Should I Share My Wealth with Family?
How Many Deaths Can a Startup Survive?
This is Probably Your Last Success
Why Do We Still Have Full-Time Employees?
The Case Against Full Transparency
Should I Feel Guilty for Failing?
Always Take Money off the Table

The 7 Deadly Startup Business Sins

George Kassabgi

The 7 Deadly Startup Business Sins

So much has been written about startups and founders, it’s challenging to sort through it all and make sense of advice that often ‘depends’. Here’s my guide to entrepreneurial sins from 2 decades of entrepreneurship.

Taking an honest look at your startup — never an easy thing to do.

But you must.

Being too Early

A startup needs to be early to market, to disrupt while an early market is not yet conducive to incumbent self-disruption. But being too early is often deadly. No amount of brilliant entrepreneurship will save a venture that is too many years ahead of the convergence of factors necessary for success.

Too early to market

How many years is too many? This depends largely on capital, but a few years of prematurity may suffice.

What makes this business sin particularly deadly is founders can be totally ‘right’ about the innovation but simultaneously totally ‘wrong’ about the timing of market conditions.

Look for clear signs that what you (and your close competitors) have built is ‘way ahead of its time’ in a bad way.

Be honest about it.

‘Dumb Money’ Capital

“Their money is just as green as any other” says the smug founder raising capital, acting dismissively about the process. The inconvenient truth is that investors in your startup need to be value-add business partners.

This is a high bar but going beneath it will create drag for your venture, particularly in the long-term — particularly during tough times!

What most entrepreneurs unhappily discover about this business sin is — you can rid yourself of a bad hire, a bad product release, even a bad co-founder but you cannot fix a bad investor.

Scrutinize potential investors as you would a co-founder and business partner.

Think about that. You cannot fix it.

3–5 year Planning

Nearly everything learned in a typical MBA program is geared towards the management of an established business, where long-range planning is necessary. A startup is never a small version of a mature business.

3-5 Year Planning

The new business is analogous to an infant or toddler: the time horizon for planning is weeks and months, not years.

A business plan may be helpful for the team to check underlying assumptions, but confidence in multi-year plans for a nascent venture is a sign of delusion.

What else is the team delusional about?

Manage your early-stage startup as a parent nurtures their toddler. It’s all about running experiments and iterative learning.

Founder as a Verb

While plenty has been said about the unique importance of startup founders, nothing spells disaster like a founder that is no longer effective but believes the opposite to be true.

This is when founder is a verb rather than a noun and the venture suffers.

What works splendidly in early phases of a business venture may by ineffective later on, and some founders do not evolve accordingly.

At times the shift in skill-set needed is significant.

Surround yourself with high-quality people. When this ‘situational awareness’ is solely on the shoulders of those foundering, this becomes a knotted situation.

Lack of Integrity

No single quality of the immature business venture is more pillar than integrity, yet often this is out of focus.

Lack of integrity takes many forms, some obvious flavors:

  • Employee discrimination (of any kind)
  • Misleading stakeholders (employees, shareholders, partners)
  • Mismanaging or misrepresenting financials (for any reason)

Impeccable integrity in the management team and Board of Directors is the starting point.

Lacking integrity is an attribute that can rarely be ‘put back’ into a person or team. Integrity is binary — it is either there or not. It flows downward into the organization.

“Is this person of utmost integrity?” should be the question to answer of a management candidate or investor.

Not Giving a Shit

It’s common for an entrepreneurial team to be faced with the kind of challenges where one fundamental question emerges: do we care enough to do what’s right? Consistently. Does what we are doing stand scrutiny?

This seems so basic, so simple, but in failed ventures it yields to other things: to convenience, ‘quick fixes’ and to shortsightedness.

We can look back at the way things are handled and ask ourselves: did we give enough of a shit about how this was handled?

Customers, partners and employees will feel when this is not happening. So be sure to give some.

Fatigue

Perhaps the most overlooked startup deadly business sin. Fatigue is the wearing down of passion, energy, patience, where time and the pressures common in startup efforts intersect.

It’s been said that overnight success is “seven years in the making” and seven years in a startup can feel like over a decade.

In the span of a typical career — let’s say 30 years, a 7 year journey is approximately 1/4 of it, so pace yourself!

What happens when you combine one or more deadly business sins with fatigue? Do what you do to decompress, to regain focus and re-energize.

And so there you have the 7 deadly business sins of entrepreneurship:

  1. Prematurity
  2. Dumb Money
  3. Delusional Planning
  4. Foundering
  5. Lacking Integrity
  6. Not Caring
  7. Fatigue

One thing to note: all but the first are entirely under your control.

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