February 10, 2026
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Most founders inherit the CEO title before they understand the role. You need to shift from builder to scaler, or you’ll become the bottleneck.
Highland combines expert CEO coaching, a structured curriculum, a company-wide operating system (Northstar OS), and a community of peers scaling alongside you.
Highland Academy is a self-paced school for any founder or operator who wants to level up. Highland Society is an exclusive community of 150 or fewer CEOs.
I had no idea what the meeting was about, but quickly learned they wanted me out as CEO after nearly ten years running the company. I had missed two quarters in a row and that was apparently enough to lose their confidence in me as the leader.
This set up a nearly 24-month battle to buy them out of the company 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 yet a great CEO. I still acted like an early stage founder. I was more builder than scaler. More bricklayer than architect.
I prided myself on working harder than anyone and brute force did, in fact, get us pretty far (tens of millions far). But something had gone wrong. Horribly wrong. Growth slowed and I had become the limiting factor. The decision had been made. I needed to be removed.
We did eventually find the capital to buy this investor out. We removed the cultural cancer and had a new lease on life. Then we went on a tear. We reaccelerated growth and 5x’d our valuation in less than two years. This led to a series of milestones and eventually a big acquisition by GoFundMe.
But this story isn’t as simple as: remove bad guys, find huge success. The experience exposed my blind spots as a leader in the most embarrassing of ways. But it also accelerated my learning curve unlike anything else could have. It lit a fire under me to understand my true role, the role of CEO, 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 obsessed about finding the answer to a few simple questions that not many people could answer for me:
What should I be doing all day?
What should I actually focus on?
What does a CEO actually do?
Looking back, the problem wasn’t effort. It wasn’t vision. It wasn’t leadership potential. I simply didn’t understand the role of CEO.
This is more common than people think. Most founders inherit the CEO title before they have any idea what it actually requires. You start the company, you get the title. No one sits you down and explains what the job is supposed to look like. Especially at scale.
In the early days, the scrappy founder persona works well. You advance the company with raw horse power. Build product, find target audience, create repeatability. But when you’re ready to scale, you need to ditch much of the founder mentality and fully embrace the role of CEO. They are two different things.
But I didn’t know any of this. I had advisors. I had a Board. But it wasn’t enough. So I made a promise to myself, that if I survived the investor ordeal, I would share everything I’ve learned with others. Help founders cross this second chasm. Highland, in many ways, is the result of this promise.
Join Highland: Every founder & CEO deserves great CEO coaching. This is exactly why I started Highland. Learn about it here and apply here (takes 1 minute).
Most founders initially find Highland when looking for CEO coaching. That makes sense. When you’re feeling the weight of the role, your first instinct is to find someone who’s been there before. And that’s 100% part of what Highland offers.
But the founders who get the most from Highland quickly realize it goes far beyond 1×1 coaching. It’s a complete system: a curriculum built around the seven core responsibilities of the CEO role, a company-wide operating system your leadership team can actually implement, and a community of peers who are navigating the same transition you are. Highland has two parts:
Highland Academy is our self-paced online school for founders, CEOs, and high-level operators. It contains the full curriculum organized into Leadership Kits, each covering a specific aspect in extreme depth. This includes the role of the CEO, but also the Northstar Operating System, and over 30 additional topics from ‘how to manage a leadership team’ to ‘how to sell your company’. Each leadership kit includes a Masterclass video and any applicable guides, templates, and dashboards. We built Academy for companies at any stage that want to learn and implement at their own pace.
Highland Society is everything in Academy plus live CEO coaching and an exclusive CEO community. We are purposefully keeping Society to 150 or fewer members to drive maximum value. We don’t want to be YPO or Hampton. We are about depth, not breadth.
Society members get direct access to me through weekly Chamber sessions (our version of “office hours”), where I provide CEO coaching on whatever topic, challenge, or idea they bring forward. Monthly Firesides bring in expert guests across sales, marketing, product, fundraising, M&A, and more. Member Assemblies are peer-driven discussions where CEOs lead tactical conversations with each other. And our annual Workshop in Whitefish, Montana is purpose-built for you and your leadership team, serving as an offsite to accelerate your annual planning process.
The leadership team piece is critical. Highland isn’t just for the CEO in isolation. Members bring their leadership teams into the curriculum, into Firesides and into Workshops. Why? Because the CEO is only as good as the leaders around them. Staying “tight at the top” is paramount to scaling any company.
Highland Academy is built for any CEO, founder, owner, executive, or senior manager. It’s like an MBA for serious operators. We’ve had thousands of students take our classes, or join Academy so far! Many treat it like self-paced executive coaching. Others come for the frameworks, templates and operating system (Northstar OS). Whatever your reason, Highland Academy is an extremely affordable way to level up your leadership game.
Highland Society is primarily built for scale-up CEOs and their leadership teams. Member companies span single-digit millions in revenue all the way into the tens of millions. But every Highland member has one thing in common: they’re trying to break through the scaling challenges and become a world-class CEO.
⤷ If you’re still in the building phase, or want to try before you apply, Highland Academy is the right path.
⤷ If you’re passionate about improving yourself and your team, and you’re moving from builder to scaler, then Highland Society could be a fit. You can apply here and we’ll explore together (risk free at no cost).
Highland was built to help you at three levels of your organization:
For the CEO: Deeply understand the role of CEO. Massively improve your ability to manage executives. Get the frameworks, templates, and systems to apply immediately. Then surround yourself with a community of peers who carry the same weight and scaling challenges.
For the leadership team: Get aligned through Highland’s operating system and frameworks. Hold each other accountable to results. Stop wasting energy on shifting priorities, unclear decisions, and misalignment. Most leadership teams crave this. They want fewer priority shifts, clearer direction, and less wasted energy.
For the entire company: When the CEO and leadership team operate with clarity, rhythm and standards, the benefits cascade through every level of the organization. Employees have the strategic context to make good decisions. They understand where the company is heading and how their work contributes. Ambiguity disappears and impact becomes measurable. The company shifts from reactive to proactive.
After the near-ouster, I became obsessed with studying the CEO role. Not business strategy. Not fundraising tactics. The role itself. What do the best CEOs in the world actually do? What separates the ones who scale from the ones who stall out?
What I found is that every great CEO masters seven core responsibilities. I now call them Highland’s CEO-7 and they’re core to the program curriculum.
Despite the name, Highland’s CEO-7 is not just for CEOs. These same responsibilities show up in almost every senior leadership role. Many Highlanders study the CEO-7 to better themselves in their current role, and to prepare for starting a company or taking the #1 spot some day.
I wrote a complete breakdown of the CEO-7 here:
⤷ What a CEO Actually Does: 7 Essential Responsibilities
Highland CEO-7 Masterclass: If you want to go deeper, I created a whole Masterclass and instruction guide on the 7 core responsibilities of a CEO. Access it here.
Understanding the CEO role was the diagnostic. But I still needed a system to actually execute on it.
I looked at everything that was out there. EOS. OKRs etc. and I struggled with all of them (especially after $10M in revenue). They either broke down under complexity, created more administrative overhead than alignment, or simply didn’t address the full scope of what a scaling company needs from an operating system.
So, begrudgingly, I built my own and called it the Northstar Operating System (“Northstar OS”)
The Northstar OS provides a solution for the CEO to implement the first three core responsibilities:
This isn’t textbook stuff. I built it under fire, refined it in real time, and watched it transform how our entire organization operated. The Northstar OS is what powered our comeback, helped us 5x our valuation, and ultimately led to the GoFundMe acquisition. And it’s no coincidence that the Northstar OS maps to the first three CEO responsibilities. When clarity, rhythm, and standards are running, the other four become significantly easier to execute.
In a strange way, I’m grateful to those investors for confronting me when I was a struggling CEO. I wouldn’t have had the motivation to study the role the way I did, and document every framework and system that worked.
I believe that great leaders are made, not born. The CEO role can be studied, practiced, and mastered. It shouldn’t be a mystery and it shouldn’t take a near-death experience to figure out.
Highland exists to shorten your learning curve. To help you cross the chasm from builder to scaler without the painful lessons I had to learn the hard way. If you lean into it, it will work. But it does come down to you.
I’m looking forward to supporting your journey.
How is Highland different from 1:1 CEO coaching? Most CEO coaching is a conversation between you and a coach. That’s valuable, but it stops with you. Highland includes direct coaching through weekly Chamber sessions, but it also gives you a structured curriculum (the CEO-7), a company-wide operating system (the Northstar OS) your team can implement, and a community of peers navigating the same challenges. A traditional CEO coach helps you think through problems. Highland helps your entire organization operate at a new level.
What’s the difference between Highland and Hampton? Hampton is a broad network of founders and executives with over 1,000 members. Hampton’s core structure is peer groups, similar to YPO and EO that came before it. Highland is more curriculum focused, and covers a wide array of leadership topics in extreme detail, with frameworks, templates, and dashboards you can implement immediately. In Highland Society, you get direct CEO coaching with Scot and a community of peers for support. It’s limited to 150 members (or fewer) to maximize value.
What’s the difference between Highland and EOS? EOS is a business operating system. Highland is a leadership program, CEO community, and operating system combined. Highland’s Northstar OS was built because EOS (and OKRs) started breaking down at scale, particularly past $10M in revenue. EOS provides a rigid framework that works decently well for smaller companies, but doesn’t adapt as the company enters new phases of growth. The Northstar OS was designed to remove complexity and create alignment as organizations grow toward $100M+.
What is Highland’s CEO coaching like? Highland’s CEO coaching happens primarily through weekly Chamber sessions with Scot (our version of office hours). Members bring whatever is top of mind: a hiring decision, a board conflict, an organizational restructure, annual planning, a personnel issue. Scot provides direct coaching in a small group format. Topics often connect back to Highland’s curriculum, but anything is fair game. Members consistently say that having an objective, experienced operator outside their company to think through problems with is one of the most valuable parts of the program.
How much time does Highland require? Highland Academy is fully self-paced. Go as fast or slow as you want. Highland Society is designed to fit into a busy CEO’s schedule. Chamber sessions run weekly, Firesides are monthly, and Member Assemblies happen on a regular cadence. Most sessions are recorded so you can tune in afterwards. The annual Workshop in Montana is a multi-day event. Most Society members spend a few hours per month actively engaged with the community and curriculum.
Can my leadership team access Highland? Yes, and this is one of the things that sets Highland apart. Highland Society members bring their leadership teams into the curriculum, into monthly Firesides with expert guests and into the annual Workshop in Whitefish. There’s even Leadership Team Assemblies where executives connect with peers across all Highland companies. Highland also provides support for teams implementing the Northstar OS.
How do I join Highland? Highland Academy is open to anyone, but best for founders, CEOs, owners, executives and senior managers. Highland Society requires a short application since membership is capped at 150 CEOs. There’s no cost or commitment to apply. The Highland team will explore whether Society is the right fit based on your company stage and goals. If you want to try before you apply, start with Academy and go from there.
