This story is real, but it isn’t interesting.

No one actually cares. It’s not a good story. It doesn’t tell you what we were all about, or what our company stood for. It doesn’t make you feel anything.

But what if I told you the day this story ran in the San Diego Tribune I was puking in the office bathroom after an anxiety attack. That only 24 hours earlier my lead investor told me they wanted me out as CEO. That they would block all new financing. That we had six months left of cash before we lost control of the company.

Then, what if I told you I resigned as CEO to four of the five board members. But before I could call my lead investor and seal the deal, my co-founder Pat took me out for a beer and convinced me to stay and fight.

He reminded me that, at Classy, we don’t give up. We adapt and overcome. We prove people wrong, like we always had.

That’s a lot more interesting.

* * *

Never say die.

When I was a kid, I loved the movie The Goonies (like so many kids in the ‘80s and ‘90s). “Goonies never say die” became a catchphrase for a whole generation of kids.

But why?

Because there are always people in life trying to push you down. Take advantage. Tell you you’re not good enough. And in this case, it was the kids, not the adults, who refused to give up. They were the ones who saved their homes from being torn down by developers.

This made millions of kids think they could do the same. They could be the hero of the story. What an incredible feeling.

The next time something hit me this hard I was around ten. My parents put on the double CD of Les Misérables, and that was it, I was obsessed.

I knew every word. I could sing every song. But my favorite was this:

Do you hear the people sing?
Singing the song of angry men?
It is the music of the people
Who will not be slaves again!
When the beating of your heart
Echoes the beating of the drums
There is a life about to start
When tomorrow comes!

It’s a similar feeling. Being pushed down. Tossed aside. Told your place in the world.

But rising up anyway. Believing in a better tomorrow.

I didn’t understand French politics when I was ten (still don’t if I’m being honest). And I didn’t understand what these people were even revolting against.

But I did know exactly how these lyrics made me feel.

And just like the Goonies, it unlocked something in me. It became part of me. Part of my identity. I loved it.

* * *

Feeling something.

30+ years later I still think about this.

Why do I love the things I love?

Of course a movie, an album, or a book is different from a company. One you expect to entertain you. The other you expect to solve a problem for you.

Right?

I’m not so sure anymore. Especially not in 2026.

I don’t really love things that make me slightly more productive. Or efficient.

I love things that make me feel something. Especially when that feeling taps into a personal value I already hold, but maybe haven’t been able to fully articulate before. That feeling is magic.

So, I’ve been wrestling with this question…

How does a product or service become something people truly love? How do you build that kind of emotional connection with customers?

I don’t think you get there by asking customers what they want. Although that’s still necessary.

I don’t think you get there by proving your product is better than someone else’s. Although that’s usually necessary too.

I think you get there by first figuring out how the company makes you feel. Not how you want other people to feel. How it makes you feel.

Why do you care? What do you believe? What do you think is wrong that needs fixing?

Only after you figure this out for yourself can you get anyone else to feel it too.

* * *

Standing for the underdog.

Classy was a software company for nonprofits. But really, to us, it was a company that helped nonprofit leaders doing some of the hardest work, with some of the highest stakes imaginable, get the technology they deserved.

We stood for the underdog.

Nonprofits are perennially underfunded and underappreciated. A lot of the value they create doesn’t show up neatly in numbers. That’s difficult for people to accept. And it’s hard on the people that work there.

Oh, you work for a nonprofit? That’s cute.

Once we got into the space, we learned very quickly that people don’t value nonprofit leaders the same way they do for-profit leaders.

We thought that was wrong.

Nonprofit leaders were just as smart, capable and innovative as any of the for-profit leaders we knew. They deserved equal respect. And somebody needed to tell their real story.

So we created the Classy Awards. The “Oscars of Philanthropy” that highlighted the amazing work that nonprofits were doing around the country and world. You didn’t need to be a Classy customer to be nominated or win an award. And we put real money and awareness on the line.

2,000 people would show up in a theatre in San Diego to see who won and hear their stories. There wasn’t a dry eye in the place.

Still, most investors didn’t get it. Why would you put on an elaborate award show as a software company? That’s an expense you don’t need.

Then, in 2012 we finally had a signed term sheet for our first $5M round. Midway through due diligence, we caught the investor shopping the Classy Awards around, trying to find anyone who could take it over because he thought it was a distraction.

We ripped up the term sheet and walked away.

We had to protect the feeling. Protect our brand’s purpose.

* * *

Losing that loving feeling.

When Pat convinced me to stay and fight, it kicked off a two-year battle that took almost all of our energy and focus. Eventually we bought the investor out of the company and regained control. It was one of the proudest days of our lives.

But the fight was painful and costly. Not just to us, to the nonprofit leaders we supposedly stood for. Some of the original magic had disappeared. That beautiful feeling that attracted so many people to Classy was harder and harder to find.

I’m sure you’ve experienced the same thing with brands you love. One day it just feels different. You can’t quite place it. But it just isn’t like it used to be.

Our customers felt it. Our team felt it. We felt it.

So we launched an internal campaign called “Back to why”. The goal was to tap back into that energy, those beliefs, that feeling from the early days. Not to go backward…

But to remind ourselves why we cared in the first place, and amplify that feeling going forward.

(yes, we even dressed up like Anchorman characters at the company kick off that year)

It worked.

The company went on a tear for the next several years, all the way to GoFundMe acquiring us in 2022. But something else changed during those years too.

I did.

I eventually realized those investors weren’t entirely wrong about me. I needed to grow up. Learn how to become a better CEO, not just a founder dressed up like one.

It wasn’t just about getting the feeling back. It was about making sure the feeling could live on without us.

* * *

How to scale feeling.

Feeling isn’t automatic. Even when you’re small, just you and your co-founders, it’s not a given. Most founders skip right over this stuff. It feels too introspective. Not enough about “customer problems” or “rapid iteration”. We’re all in a race now after all, aren’t we?

Here’s what I learned as CEO in the post-war era at Classy. Whatever you call it. Feeling. Purpose. Mission. Values. You need to be intentional about it. That’s what the Classy Awards were. That’s what “Back to Why” was.

Every company has a rational side and an irrational side. Numbers explain the first. Only feeling explains the second. And the two are always fighting.

People will try to talk you down from the irrational. It doesn’t make sense. It’s too risky. The numbers don’t pencil.

But that’s because they can’t feel what you can… at least, yet.

I realized I wasn’t just scaling the business, I was scaling a particular feeling with it.

The feeling of being judged, but overcoming anyway.
The feeling of being overlooked, but eventually finding your people.
The feeling of dedicating your life to something bigger than yourself.

This was the nonprofit leader. But it was also us.

We were underdogs too.

⁂

If you’ve been following this newsletter, you know I’ve been going through a similar process with Highland lately.

Why do I care? What do I believe about the space we’re in? What about the company gives me that feeling? Lights me up. Motivates me to keep going.

So last week, after Highland Workshops, I brought up Spotify, went to the search bar, and typed in Les Misérables. Then for the first time in decades I listened to the entire musical front to back.

When I got to disc 2, the song Drink With Me, I stopped. There was a line I never noticed before.

At the shrine of friendship, never say die.

It immediately brought me back to that bar in San Diego with Pat, the night I tried to resign as CEO.

And then it hit me. That is exactly what I want Highland to feel like to our members. The guy at the bar who helps you keep going. Who reminds you that you’ve had it in you all along.

Who never lets you say die.

CEO coaching is the business.
But never say die is the feeling. 🏴‍☠️

Till next time,

Scot

→ scotchisholm.com
→ highlandacademy.com

~~~

P.S. Thank you to everyone who gave feedback on the new Highland website wire frames! We had dozens of emails back, mostly positive, but with fantastic ideas for refinement. If you missed it, you can see the wireframes here. I’ll share full designs in the coming weeks.

Onward!

🐐🏔️