Articles
How to be a Terrible Startup Advisor
Which Version of Me for Dinner Tonight?
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

Your Worst User Isn’t Who You Think It Is

JS
Judd Schoenholtz
Your Worst User Isn’t Who You Think It Is

Out of the hundreds of thousands of people using my company Open Listings to shop for and buy homes, I thought I knew who our worst users were — even by name.

There was Sarah* in San Diego who went on 134 home tours before finally buying one. Then, there’s Dan in San Francisco who’s asked our in-house agent team questions about nearly 1,000 properties but hasn’t submitted an offer on a home yet. And, there was Chris, who tried to negotiate our already low fee down to zero by blackmailing us with negative online reviews.

As CEO, I cared deeply about all users and every shred of feedback. I read every review, internalized problems, and prioritized solutions. I felt confident that we were super customer-centric and solving the most important problems.

Then, I had lunch with an investor who told me a story about a friend he had referred to our company a couple months back. This buyer had gone on a tour of a home but disliked the showing agent who toured with him so much, he decided not to use us to buy a home and never returned.

Unhappy customer

At first, I was defensive. He must be mistaken. We follow up with every bad review. Imperfectly rated showing agents are phased out of the platform. We race to fix any issues we hear. Our NPS score was over 80 last month!

The investor shrugged. His friend didn’t bother to rate the showing agent. They went dark, chose another solution, and barely thought about our company again.

That’s When I Realized: That Person is Our Worst User

All of a sudden, the people who I had thought were our worst users turned out to be some of the best. They at least ‘cared’ enough to use the product and be vocal about it.

For an early-stage company, insight is more valuable than incremental revenue. Their early criticism actually helped us in the long-run because we could grow from it.

In contrast, our worst users never returned and gave us nothing.

These detractors who leave silently, giving our team no issues to fix or negative feedback to unpack are the hardest to understand and to segment. And, they make up the majority of the users we don’t retain.

OK, I get that these users are the worst. What do I do about it?

Hunt down silent churners, and get their feedback.

David Cancel, the CEO of Drift says:

“In today’s world, helping is the new selling and customer experience is the new marketing.”

Helping our users becomes easier and customer experiences get better if we strengthen our commitment to both our best and worst customers, and most importantly, take the time to find and listen to them.

Hustle, cold call, survey, install HappyOrNots — do whatever it takes to get to the bottom of a user’s frustrations.

If we spend the time to seek out and truly listen to the customers who didn’t even bother leaving negative feedback, it has the potential to turn all of our “worst customers” into our best.

1. Stop “Drinking the Soylent”

As a startup begins to scale, it’s easy for group-think to take over internally.

Potential problems and negativity can be overlooked, swept under the rug, or flat out ignored as everyone hitches themselves to the rocket ship. But, it’s extremely dangerous to stop asking questions and taking contrarian viewpoints.

At the end of the day, the best startups solve problems. If you dismiss problems, you are really dismissing your opportunity to be great.

Matt Bloze Tweet: Drinking the Soylent

2. Ensure you are focusing on the right user segments

Early adopters are a great audience for early-stage startups because they’re willing to try anything and they tend to be vocal about what they like and don’t like.

But, what if your most vocal detractors aren’t actually your target users?

Instead of just listening to existing feedback or seeking out more of it, it’s crucial that you also understand and segment your users correctly.

Only then can you prioritize the feedback and solutions that are right for your current business.

3. Understand retention = growth

Often, when we think about growth it’s easy to fall into the trap of only considering new users.

However, acquiring a new customer can be 5 to 25 times more expensive compared to retaining an existing customer. Even when a startup is in growth and scaling mode, it’s important to remain focused on retention.

If you’re taking a hard look at product and process improvements that reduce churn, you give displeased users a voice, even if you aren’t able to capture their feedback before they leave.

Turning your worst users into your best

Giving a voice to previously unheard users is the easy part. But, it also means you need to listen intently, design the right solutions, and test-and-learn from the improvements you launch.

Getting to the truth about your product, warts and all, will help your business iterate faster and build the experience users won’t want to ignore.

*Note: Names have been changed to protect the innocent


Also worth a read:

  1. How To Reach Your Target Customer: Getting Up Close and Personal
  2. 5 Tips To Improve Customer Experience
  3. How to Create a Customer Service Culture on People Power

Find this article helpful?

This is just a small sample! Register to unlock our in-depth courses, hundreds of video courses, and a library of playbooks and articles to grow your startup fast. Let us Let us show you!

OR
GoogleLinkedInFacebookX/Twitter

Submission confirms agreement to our Terms of Service and Privacy Policy.