I Accidentally Built a Business That Proved Everyone Wrong About Scaling (And Then Shut It Down)

Or: How Amy Giddon's 50K-User App Taught Me More About Client Retention Than Any Growth Hack Ever Will

Pull up a chair: Your customer retention strategy is probably trash.

Not because you're bad at what you do. But because you're trying to scale a business while treating humans like SQL queries.

I sat down with Amy Giddon this week—founder of Daily Haloha, an app that got 50,000 people to actually give a shaet about connecting with strangers—and she absolutely wrecked my worldview about what makes customers stick around.

The Part Where She Hid Behind a Curtain (And Immediately Regretted It)

Here's the thing that made me actually pause my note-taking and just... listen.

Amy built this beautiful anti-social-media app. Anonymous. Values-driven. The whole nine yards. She deliberately stayed behind the brand, thinking the product would speak for itself.

Classic founder move, right? Let the tech do the talking.

Then she had to shut it down.

And when she stepped out from behind the curtain to tell her users why, she got flooded with emails. Not angry ones. Grateful ones.

People thanked her. They asked for recommendations. They wanted to know her—the human behind the thing they'd been using for years.

She told me: "I didn't think I would hear from anyone. I thought they would just go on to the next shiny object."

Narrator voice: They did not go on to the next shiny object.

Why Your "Frictionless" Customer Experience Is Killing Your Business

Here's where Amy absolutely cooked me (and probably your entire CX strategy):

We've spent the last five years—accelerated by COVID—removing every ounce of humanity from our business interactions. Contactless delivery. Self-checkout. Chatbots that can't even pretend to understand context.

We called it "frictionless." We called it "efficient."

Amy calls it what it is: disconnection at scale.

And now? Your customers are drowning in a sea of AI-generated content, distrusting everything they see online, and desperately craving something real.

The companies that figure out how to add strategic friction—the human kind—back into their customer relationships? Those are the ones that are going to absolutely dominate the next decade.

Because here's the uncomfortable truth: In a world where AI can replicate your product, your pitch, and your positioning in 3.5 seconds... the only thing left to compete on is how you make people feel.

The Loyalty Tax (And Why You Should Be Paying It)

Amy dropped this gem on me: "Connections engender loyalty. And loyalty does a lot—it lets people vote with their dollars rather than get distracted by shiny objects. It also helps companies recover from missteps."

Translation: When your customers actually feel connected to you—like, human-to-human connected—they forgive you when you screw up. They don't immediately churn when a competitor offers a 20% discount. They become advocates instead of transactions.

But here's the thing literally nobody talks about: Building that kind of loyalty requires vulnerability.

It requires stepping out from behind your brand positioning and showing people who you actually are. It requires reciprocity—not just taking from your customers but giving them opportunities to contribute, to matter, to belong.

Most B2B companies are out here acting like their customers are line items in a spreadsheet. Meanwhile, your competitors who figure out human-to-human relationships? They're building moats you can't cross with a bigger ad budget.

The Belonging Formula (That Actually Works)

Amy laid out what fostering real belonging looks like:

1. Reciprocity: Show yourself, don't just ask others to show up

2. Contribution: Give people ways to matter, not just consume

3. Recognition: See people for who they are, not what they buy

4. Humility: Be vulnerable enough to be forgiven

And here's the kicker—this works for employees and customers. Because the way you treat your team is exactly how they'll treat your customers.

If you're transactional with your people, they'll be transactional with your clients. If you're human with your team, they'll bring that humanity to every customer interaction.

Your employee experience IS your customer experience. Full stop.

The Part Where I Tell You This Actually Matters For Your Bottom Line

I know what you're thinking: "This is all very heartwarming, Karl, but I have a board meeting next quarter and they want to see revenue growth, not feelings."

Fair.

But here's the thing: Research shows that increasing customer retention by just 5% can boost profits by 25-95%. And in today's market—where trust in institutions is tanking, AI is making everything feel fake, and your customers are exhausted from being marketed at 24/7—authentic human connection is the only sustainable competitive advantage left.

The health tech and medtech companies that get this? The ones building stakeholder engagement strategies that actually prioritize relationships over transactions? They're not just surviving disruption—they're thriving through it.

Because when the market gets weird (and oh buddy, it's getting weird), people don't stick with the cheapest option or the flashiest features. They stick with the companies that made them feel something real.

Watch This Episode (Seriously)

Amy's insights on building unshakeable business relationships in the age of disconnection are exactly what every scaling startup executive needs to hear right now.

We talked about the crisis of disconnection, why AI is actually making human relationships more valuable (not less), and how to transform your company culture through authentic connection.

If you're trying to reduce client churn, improve customer satisfaction, or build a business that can weather whatever chaos 2025 throws at us—this episode is for you.

Because at the end of the day, your business isn't B2B or B2C. It's H2H—human to human.

And the sooner you remember that, the sooner you'll stop watching your customers leave for the next shiny object.

P.S. Amy's sabbatical after running Daily Haloha for five years? That's what good leadership looks like. She's out there consolidating everything she learned about loneliness, connection, and belonging while the rest of us are grinding ourselves into dust wondering why our retention metrics suck. Maybe the problem isn't your customer success playbook. Maybe it's that you've forgotten how to be a whole human being who relates to other whole human beings. Just a thought. 🤷

Karl Pontau hosts The Human Connection Podcast, where we talk about the stuff that actually matters in business: the humans running it. Because whether you're B2B or B2C, it's really H2H—human to human. Subscribe so you don't miss the next episode where we probably say something that'll make your HR department uncomfortable.