February 15, 2026
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Getting pushed out of my own company.
I got called to my lead investor’s office in La Jolla, California. I had no idea what the meeting was about.
I sat in the conference room for 10, then 20, then 30 minutes, waiting. Then my lead investor and his boss walked in… the head of the firm. Ut oh.
“Thanks for coming, Scot. We’ll get right to it. The partners aren’t happy with Classy’s performance. We think it’s time for some change.”
I had missed two quarters in a row and that was enough to lose their confidence in me.
The decision was made. I needed to be removed.
This set up a 24-month battle to buy them out and get us back on track. These were some dark times, but also some of the deepest reflections of my life.
I had gotten the company this far, but I wasn’t a great CEO. I still acted like an early stage founder. I was more builder than scaler. More brick layer than architect.
Doing a webinar from a hotel room – early days of Classy.
I prided myself on working harder than anyone and brute force got us pretty far (tens of millions far). But something had gone wrong. Growth slowed and I had become the limiting factor.
I hated them for it. But they weren’t wrong.
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We eventually found the capital to buy this investor out. Removed the cultural cancer and the company had a new lease on life. We reaccelerated growth and 5x’d our valuation in a couple years. This led to a series of milestones and eventually a big acquisition by GoFundMe.
Classy & GoFundMe post-acquisition kickoff event.
But this story isn’t as simple as: remove bad guys, find huge success.
The experience exposed my blind spots in the most embarrassing ways. But it also accelerated my learning curve unlike anything else could have. It lit a fire under me to understand the CEO role better than anyone they could possibly bring in to replace me.
Not because I fantasized about becoming the next Steve Jobs or Jeff Bezos. I didn’t. But I wanted answers to basic questions, that for some reason, no one could give me.
What should I be doing all day?
What should I focus on?
What does a CEO actually do?
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7 Core Responsibilities of a CEO
After the near-ouster, I obsessed over studying the CEO role. What do the best CEOs in the world actually do? What separates the ones who scale from the ones who plateau?
What I found is that every great CEO masters seven core responsibilities. I now call them the CEO-7 and they’re core to Highland’s curriculum.
Provide Absolute Clarity — Answer three fundamental questions for your team: Why are we here? Where are we going? How are we doing?
Create a Reliable Operating Rhythm — Build predictable planning and execution cycles that keep leaders aligned and accountable.
Set Cultural Standards — Define what “great” looks like across Brand, Product, Performance, and Leadership. Hold the line as you grow.
Build an Elite Team — Assemble the right people and develop leaders at every level.
Find and Optimize Cash — Never run out of money. Manage the financial plan and find cash-generating levers in your business model.
Manage Key Relationships — Build and maintain relationships with customers, partners, your board, and investors.
Manage Yourself as the Leader — Your personal performance impacts everything. Take care of your physical and mental health like a professional athlete.
Despite the name, the CEO-7 is not just for CEOs. These same responsibilities show up in every senior leadership role. Whether you’re a first-time manager, or a seasoned executive, this framework will sharpen how you lead.
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The first step to becoming a great leader is knowing the role.
I wrote a complete breakdown of the CEO-7 here:
⤷ What a CEO Actually Does: 7 Essential Responsibilities
Till next time,
Never say die 🏴☠️
~~~
P.S. I launched a new version of my personal website!
It’s meant to look and feel like a publication for operators, not a sales pitch for myself. All of my content now lives there:
Big props to my team on the launch (nearly six months in the making)!
Especially Jael – my head of content and partnerships, and Gregory – our very talented web designer and developer.
Give it browse and let me know what you think!
🐐🏔️
