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

Why Do I Feel So Alone?

WS
Wil Schroter
Why Do I Feel So Alone?

Why are Founders often so lonely? It's a combination of things.

First, unlike most other jobs, Founders often don't have a lot of relatable peers in their close-knit group. Most people can sit at lunch and complain about their jobs and get a bunch of nods.

Us Founders often explain what we're going through and get the "thousand-yard stare" from someone wondering how to get out of the conversation.

What do Founders do in this case?

The first thing they do is to find other Founders to meet up with.

The one amazing thing about Founders, by the way, is that they immediately tend to connect with and appreciate other Founders.

It's amazing.

Every Founder understands what it means to be staring into the abyss daily, and how those feelings are so hard to wrestle with. Just sitting across from a single Founder over dinner and laying everything out on the table can be incredibly satisfying.

Will I be less lonely at some other point?

Have you ever heard the phrase "it's lonely at the top"?

The basis for that is that as you and your position progress, you actually wind up with fewer and fewer direct peers, which creates this feeling of loneliness or in some ways, just disconnection from folks who aren't naturally doing what you're doing.

The best way to work against this is to develop relationships — particularly within your company — that have nothing to do with work. It's a bit challenging because at the end of the day you're still writing people's paychecks.

But in order to have a peer relationship, you have to be a peer at something that's not work.

In Case You Missed It

Why Am I So Lonely? (podcast). You got the TL;DR, now check out our podcastified take on the topic of Founder loneliness and join Wil and Ryan as they discuss what we can do to minimize the negative impacts it has on our lives, families, and startups.

How I Harness My Insane Startup Anxiety. A startup is a torrent of anxiety. We’re likely doing things we’ve never done before with products that have never existed before. So let’s just start off by admitting we’re all freaked out and we all need to figure this shit out.

I’m Burnt Out. What Do I Do? When we hit a point of burnout and ignore it, the problem only gets much worse. So let's take a look at what Founders do to deal with burnout head on.

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