Sitemaps
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
How Does My Startup Get Acquired?
Can Entrepreneurship Be Taught?
How to Pick the Wrong Co-Founder
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
Founder Impostor Syndrome Never Goes Away
When is Founder Ego Too Much?
The Invention of the 20-Something-Year-Old Founder

Getting Your Idea Going: When To Jump Ship

Wil Schroter

Getting Your Idea Going:  When To Jump Ship

There you are: Standing at the edge of the metaphorical startup cliff. You want to cannonball into the abyss that is Founder-hood… But, you’re scared as hell that you might be jumping in too soon.

What do you do?

Are you asking yourself the right questions? How do you evaluate whether this very moment is the one to take the plunge? Are you sure?

Every startup Founder goes through this inner battle, yet few know what to look for.

While everyone’s situation is unique in their own way, there are three critical indicators that can help you determine if the timing is right— before making the leap.

Take the leap

Critical Indicator #1: Customers are buying — constantly

The moment you start seeing real revenue from a consistent stream of customers, it’s time to consider a bigger commitment.

The operative parts of that suggestion are:

  • “Real Revenue” — Which suggests it is meaningful enough to pay some real bills.
  • “Consistent Stream” — Which means people are constantly buying.

In the early days, it’s hard to tell the difference between a blip and a trend in your sales numbers. You may have had some good press, or a really fortunate week on sales —but, next month, you might slump hard.

The most prudent move is to try to see if you can replicate at least two months in a row — ideally more.

Forcing yourself to replicate that trend is the very essence of what it will take to keep your startup moving forward—so it’s exactly the right focus.

Critical Indicator #2: You’re losing money by not being committed

At some point, it may become obvious that you’re actually losing money by not being available all the time.

You may have signed customer contracts that you’re required to fulfill, or need to develop a product feature that will increase sales.

The list goes on.

The difference, however, is whether or not you can actually be sure that your lack of commitment leads to a clear lack of income. This gets a bit fuzzy when you start making assumptions like:

“If I worked on this more, it might yield more income.”

That may in fact be true, but it’s not the same as literally leaving money on the table.

If you’re leaving a meaningful amount of money on the table — it’s probably time to jump ship.

Take the leap

Critical Indicator #3: Not because “There’s so much to do”

It’s easy to get lured into going “all in” because there’s just so much to do. If you could only devote more time to working on your social media campaign / writing more code / making more customer calls / etc.

Then — Things would be moving so much faster!

All of that is true (and it will always be true) but, you can’t use that as the single indicator that it’s a good idea to go “all in”.

What you’re reacting to is a constant within startup culture. There will always be a mountain of work in front of you no matter how many resources you add. You’re just reacting to the first of many resource issues.

Yes, you would definitely move the business forward faster if you were more committed. But, before you make that commitment, be sure that the other indicators are clearly blinking “green”. Because this one, frankly, will be forever red.

REVENUE = COMMITMENT

The best possible outcome would be for you to focus on driving real revenue before making a real commitment.

But, sometimes, that’s just not possible.

Millions of Founders before you have made the leap without knowing if there was a paycheck in it. I guarantee none of them were excited about the prospect of not being paid.

The decision is yours, but if you can hold strong and focus on building a real income-producing business before making the leap, then you’ll have one less thing to worry about when you make your transition.


Don’t miss out! Check out the previous editions here:

Getting Your Idea Going: There Is No Perfect Idea
Getting Your Idea Going: Popular Excuses For Not Starting

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