Where Were You When I Was Broke?
What if I'm the Best (but don't know it)?
The Right Time to Start is "Right Now"
Creating A Go To Market Strategy
A Simple Trick for Less Awkward, More Effective One-on-One Meetings
Types of Crowdfunding: Donation, Rewards, and Equity-Based
How To Create A Business Model Canvas
How Startup Funding Stages Work
Everything You Need to Know About Product-Market Fit
Sole Proprietorships: What You Need to Know
Revenue Model
Private Investors for Startups: Everything You Need to Know
Why Founders Can't Retire
The Most Expensive Equity Doesn't go to Investors
How to be Great at Worrying
Top 10 SaaS PPC Agencies (2026)
Equity Is the Most Expensive Currency Your Startup Has. Stop Treating It Like Bar Peanuts.
Can Startups Be a Team of One?
Why are We Really Building a Startup?
We Rarely "Control" Our Startups
The Problem With Never Being Done
What Should My Expectations Be?
What Actually Happens if I Run Out of Gas?
The Value of Side Quests
The Key to Success Is Mastering Failure
We Can't Predict the Future Anymore
We Wanted Efficiency. We Got Isolation.
Startups are the Future of Employment
The Founder "Hard Reset"
Where Does Our Optimism Come From?
When Popularity Destroys Productivity
Will Getting Bigger Make Us Better?
"Just Be Yourself" is Terrible Startup Advice
Embrace How Messed Up You Are
The Great Remote Workplace Reset
Can I Hire Someone to Run My Startup for Me?
How Founders Get "Fired by Promotion"
Burnout is a Treatable Injury
Stop Pretending You Don't Have Enough Time
Are We Aligned with Everyone Around Us?
Will the Payout be Worth the Sacrifice?
How Founders Blow Their Fortunes
When Should We STOP Asking for "More"?
Can Entrepreneurship Help Alleviate Poverty?
Should Employees Really be Our Friends?
Can Founders be Replaced by AI?
The Best Startup Fractional CMOs and Growth Leaders
The Best Growth Marketing Agencies: How to Choose Them and Who They Are
What if We Run Out of Goals?
Reinvention is Our Only Constant
We're So Connected — And Totally Lonely
The 10 Best Growth Agencies for Startups
My Roadmap to Becoming a Confident Leader
Is College a Waste of Time for Founders?
Are We Preventing Our Startup From Evolving?
Building a Startup That Loves You Back
When Our Friends Resent Our Success
When Our Startup Outgrows Us
When Being in the 1% Feels like Failure
We Need Outside Interests that Consume Us
If You're Not Terrified, You're Doing it Wrong
Why do Founders Suck at Asking for Help?
The Ideal Client Profile Is Your Startup’s North Star (Stop Ignoring It)
Are We Growing or Just Getting Fat?
Let's Get Back to Our Why
Does Startup Success Validate Us Personally?
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
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
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

When Should My Side Hustle be Full Time?

WS
Wil Schroter
When Should My Side Hustle be Full Time?

We've been working around the clock on our side hustle with the dream that one day it'll be our full-time gig.

But now that we're getting some traction, the real question is, when do we go all in?

The best Investor — our current paycheck

There will never be a more equitable investor than our current paycheck.

Full funding, no pitch process, and market compensation from Day One.

Compare that to when we try to actually raise money in a grueling pitch process, spend months with no income, and have to work for half of what we made last year.

While our current investor (our paycheck) has a lot of hours and distractions, it has some really important benefits: it's predictable, it's consistent, and if shit hits the fan, we just focus on that.

So we want to hold onto that sweet, sweet investor for as long as we can.

But we need more time for our side hustle!

Yep, we do.

But it's a trade-off — do we want to worry about time or money? Time can be stretched out. Money really can't.

Also, having money consistently coming in (our paycheck) actually gives us more time to work on our Side Hustle without having to worry about running out of money.

Sadly, it's one of those things we don't appreciate until after we quit and realize that having more time was much easier to manage than being broke.

What if we're getting a lot of demand? Is that time?

We want to look for a consistent demand curve over a long period of time — say 6 months or longer.

The problem is when we see our first big month we often can't tell if that's the beginning of a deluge of activity or just a single big month. We're looking for consistency over a long enough period of time so that it's a trend, not a blip.

All too many Founders have jumped ship after a single surge only to realize later it was the wrong indicator. Whether it's extending the runway for the consistent paycheck or holding out longer to make sure the activity is a true trend, the time to jump ship is always 3 months from now.

So wait as long as possible, huh?

Yes. While the excitement of a new Side Hustle is amazing, what we need to focus on is ensuring its longevity by ensuring our own longevity.

The moment we jump ship, we need to be damn sure there's a lifeboat.

In Case You Missed It

The Secret to Growing Your Side Hustle. So you want to get your side hustle on? Here's what you need to know about surviving the journey and growing your hustle into a full-time business.

3 Ways to Support Employee Side Hustles. Leaders who encourage employees to pursue their side hustles can be rewarded for that investment of trust. People gain skills and master new technologies through side hustles, which can end up benefiting you, their primary employer.

Getting Your Idea Going: Don’t Quit Your Day Job. Instead of thinking of how quickly you can quit your job, think about how long you can keep your job and push your startup forward.

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