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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
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

Will Investors Let Me "Cash Out" on a Future Funding Round?

Wil Schroter

Will Investors Let Me "Cash Out" on a Future Funding Round?

It was recently reported that the co-Founder of WeWork Adam Neumann took over $700 million off the table from investors long before the company had gone public.

How do these Founders go about getting cash out of their startups long before the startups ever cash out themselves?

Why would investors let me take money off the table?

Investors will often dangle the option of providing some Founder liquidity only when the deal they are trying to get into feels incredibly competitive.

This happens only rarely, and only amongst investors who are open to providing some Founder liquidity (some are very against it!).

Generally speaking, it only helps the investor by allowing them to get into the deal but provides very little upside to the company as the capital is being used for the Founders personally, not the company as a whole.

Does everyone get a piece or just the Founders?

Most often, the liquidity is targeted to a few people in the company who are considered key stakeholders, and whose personal gain will often sway which investor they take money from.

The moment that capital has to be distributed to more people, it becomes a slightly different transaction. You'll see some early liquidity go to employees when a company is pre-IPO, but even then the practice is locked down pretty tight.

Does it piss off employees?

Of course it does!

While an argument could be made that the Founder has invested more, and likely over a longer period of time, the fact is we're getting a check and other employees are not.

There's not a lot of ways to sugar coat that.

Can I ask my existing investors for some early liquidity?

Not really.

Once the capital has been invested, it's nearly impossible to change the terms of the deal. Existing investors have very little incentive to invest additional capital into Founder liquidity because they are already in the deal.

The only option for existing investors to ever provide liquidity is if there's a future funding round that's competitive and other investors are providing liquidity.

In Case You Missed It

Should I care About an Exit Plan? We all know that there's a possibility of selling our company, but how much planning can we really do to make that happen?

10 Things You Should Know About Investors. Over the years, we’ve worked with thousands of entrepreneurs looking to raise startup capital. Here’s what we’ve learned about how the most successful entrepreneurs prepare for approaching investors.

Should I Regret Not Raising Capital? (podcast). Have you ever asked yourself, "Do I need to raise capital to be successful?" Wil and Ryan break down why you probably don't need to regret NOT raising capital. At least not yet.

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