The Death of the Technical Co-Founder
We Do What Others Won't
Surprise, You're a Startup Again!
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

Why Money Can't Buy Happiness

WS
Wil Schroter
Why Money Can't Buy Happiness

As Founders, so many of us have joined this marathon because we believed there was our own version of "happiness" on the other side of it. The problem for many Founders, once they've "made it" is that they don't realize that money was never going to buy more happiness. In fact, it wasn't the problem they were solving for, to begin with.

Think of it like getting a big, honking bruise. In this case, that bruise is a metaphor for debt. When you have a bruise, you're constantly worried about it — it's super painful. So we think about how great it will be when it goes away. And eventually, it heals (we have some money). But all we did was get rid of the pain, we don't actually become "more healthy" than we were before.

The same goes for debt. When we're upside down on cash, all we can think about is cash. We have so many problems that stem from being broke, that having money seems like it will not only make those problems go away but also create an additional sensation that we assume must be "happiness."

But money doesn't make us happier. It just makes things less painful.

C'mon, Money Can Buy Fun Stuff, Right?

Don't get me wrong — money definitely buys things that can bring us pleasure. But where that argument breaks down substantially is that the longevity of that happiness pales in comparison to the longevity of anxiety, frustration, and sadness.

This is the part that we constantly get wrong. We can't "buy happiness." Money doesn't actually do that. It can buy us some novelty (think about the last awesome thing you bought), but inevitably that novelty fades, and we're more or less right back to where we started. Did you ever eat a delicious ice cream cone and savor it for days? Yeah, me neither.

It actually compounds over time, because each time we level up on some nice stuff to buy, it makes it that much harder to replicate that dopamine boost again. Buying that BMW was awesome, and maybe we upgraded to a Bentley, but at some point, there's sorta nowhere to go, and the relative difference in satisfaction (relative to price) drops dramatically. We actually run out of things that can make us "more happy."

Debt Lasts Forever

Conversely, debt is a bottomless pit of emotion! Debt doesn't have the fleeting dopamine hit that spending money and buying nice stuff does. I can be reminded of debt 24x7, not only in my own caveperson mind but then amplified by all of the other people in my life who are affected by it. It can ruin relationships, create a massive strain on my mental and physical health, and emotionally turn me inside out.

Oh yes, unlike having money, debt is a bruise that not only sticks around, it often gets worse with time. We feel it in every move we make in life, and we're constantly reminded of the pain. That feeling is geometrically worse and painful than having money is positive.

We Want Freedom From Pain

What we're looking for is "freedom from pain." And friends, I sincerely hope that all of you find that place. But let's not confuse "freedom from pain" with "happiness." All of the effort we are about to put in on our startups may indeed provide that freedom and flexibility we're longing for, but that's pretty much where the payoff ends. After that, all of the things we're going to try to do to ensure that "ongoing happiness" is going to fail. If we were miserable people before money, we're just going to be miserable people with money.

Instead, we need to think of this as two separate journeys. One journey is simply a financial one — we are trying to stack enough cash to make painful stuff go away — it's just not a happiness journey. The second journey is the happiness journey, and that's where we begin to confront all of the things that prevented us from being happy that we often camouflaged with the excuse that it was "a money problem."

The good news is we can work on both simultaneously, we just need to separate those goals. In the end, it's the only way to achieve the outcome we're truly looking for.

In Case You Missed It

Fat, Sick, and Nearly Startup (podcast). Join Wil and Ryan as they break down the ways Founders can learn to deal with personal hardships that are often a result of our own Startups — while we're still running them.

Optimizing for Happiness. We do something in our planning at Startups.com that is relatively unheard of in the startup business: we optimize for happiness. Here’s how we do it.

How I Harness My Insane Startup Anxiety. There are two types of Founders: those that admit they are wracked with anxiety, and those that are lying about it. We’re all going to deal with it for the rest of our lives — so why not use it as a superpower, instead of reacting like it’s kryptonite?

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