CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Every week I tackle management, operations & startup topics that are helping 250,000+ people. Sign up free: www.scotchisholm.com

I also run a leadership accelerator that helps founders develop into top CEOs. Apply here: https://joinhighland.com/apply/

My backstory: 

🚀 Founder of Classy, SaaS for nonprofits raising billions per year

🎗️ Acquired by GoFundMe in ‘22 to create largest giving platform in the world

🌲 Investor in dozens of startups out of family fund, Tall Timbers Holding Co, (Ripple, FanDuel, Hubble, Casetext, etc.)

🏔️ Founder of Highland, leadership accelerator & community for founders

🏡 Co-founder of Haskill Creek, modernized & healthier version of a Walgreens or CVS 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland & food 

⚙️ Industrial engineer & lean six sigma nerd, UMass Amherst grad 

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation

It's been a wild ride. If you're interested in any of the above, please visit my website and reach out to me there. 

www.scotchisholm.com

Scot Chisholm

Getting pushed out of my own company taught me what a CEO actually does...

In 2017, I got called to my lead investor's office in La Jolla.

I waited 30 minutes in the conference room. Then the head of the firm walked in.

"The partners aren't happy with Classy's performance. We think it's time for some change." Two missed quarters. That's all it took.

I had built the company to tens of millions through brute force. But something had gone wrong. Growth slowed. I had become the limiting factor.

I hated them for it. But they weren't wrong.

I was more builder than scaler. More brick layer than architect. It took 24 months to buy them out and get us back on track. Some of the darkest times of my life, but also the deepest reflections.

That experience lit a fire under me to understand the CEO role better than anyone they could bring in to replace me. Not to become the next Jobs or Bezos. But to answer basic questions no one could give me:

What should I be doing all day? What should I focus on? What does a CEO actually do? So I obsessed over studying the best CEOs in the world. What separates the ones who scale from the ones who plateau?

I found that every great CEO masters 7 core responsibilities. I now call them the CEO-7.

I wrote a complete breakdown in yesterday's newsletter. 

If you wanna check it out, I'll drop it in the comments.

Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland, Just, Haskill Creek

How defining “great” changed our culture (and decision-making):

A new hire asked me a simple question after onboarding:

“What does great look like here?”

I didn’t have a clean answer.

Not because we lacked ambition, but because we’d never clearly defined it.

Mission, vision, and values weren’t enough.

What we were missing was our perspective on excellence.

That gap pushed us to document our company standards. The non-negotiables that guide decisions when things get messy, fast, or ambiguous. Inspired by how Patagonia articulated its philosophies, we created standards that outlived leadership changes and scaled with the company. 

Here's how I defined them 👇 

***
ps. If you want to read my in-depth article I wrote on this exact topic, I'll drop the link in the comments.

How to define what great looks like:

Here's how to create an unstoppable strategy in 3 simple steps:

First, what is a strategy? Most leaders get this wrong. Strategy is not vision. Strategy is not goals. It's the bridge between the two. Strategy is your unique approach to achieve vision. It shapes your annual goals and daily execution. Vision leads to strategy, which leads to goals.

To create an unstoppable strategy, you need three things:

- Unique approach
- Measurable impact
- Target market

I call this "strategic AIM." A stupidly simple, crystal clear description of strategy that anyone can understand.

1. Approach
What's our unique approach to accomplishing the company's 3 to 5 year vision? Why will people choose us? How are we 10x better than the competition? What are 3 to 5 core bets, multi year initiatives, that we will pursue? Your unique approach creates differentiation at all levels.

2. Impact
What does success look like when we achieve our 3 to 5 year vision? How do we measure it and track along the way? Customer impact, financial impact, shareholder impact. Get crystal clear on what success looks like from day 1.

3. Market
Most leaders target anyone that will buy from them. This is the wrong approach. Instead define exactly who your target market is. Think of it like an archery target. Primary is the inner ring, secondary is the 2nd ring, tertiary is the 3rd ring. Dominate the first before prioritizing the second.

Your strategic AIM informs how you set pricing, packaging, and messaging. It also makes annual goal setting a lot easier. What are the company's top three annual priorities that advance our strategic AIM? Pay special attention to your multi year core bets. These help shape annual goals.

Revisit your strategic AIM at least annually. As your vision evolves, your strategic AIM should evolve. They're joined at the hip. You should always have a company wide strategic AIM, but you could also have one for different products or markets as you get bigger.

If you're a founder or operator and you enjoy my content, you should check out Highland Academy: https://lnkd.in/eAVA5ekz

How to create an unstoppable strategy in 3 simple steps:

In 2017 I was called to my lead investor’s office in La Jolla. 

I had no idea what the meeting was about. 

They wanted me out as CEO after nearly ten years running the company. 

I had missed two quarters and lost their confidence. 

That was enough. 

But they weren’t wrong, I wasn’t yet a great CEO. 

While they tried to push me out, I studied the role like a maniac. 

Determined to be better than anyone that could replace me. 

Ultimately, it worked and the company 5x’d in valuation. 

Now I teach everything I learned through Highland Academy. 

If you’re a founder working to become a great CEO, this is for you.

I'll drop a link in the comments if you want to apply.

Or shoot me a dm.

Don't screw up your annual company kick-off!

Most CEOs don't realize how high-stakes their company kick-off really is. They waste the moment. Why? 

Because they don’t realize how high-stakes it is. They think B- work is ok. Check the box. Get back to the “real work”. I mean, you do have lots of shit going on. Carving out a half-day for a company kick off can feel like a waste of time.

I've been on both sides of this. As a founder, I learned the hard way that the leaders who put their heads down and "get back to work" in January are making one of the costliest mistakes of the year. The annual kick-off isn't a distraction from the real work. It IS the real work.

Andy Grove called this "managerial leverage" in High Output Management. The idea is simple: what you put in is nothing compared to what you get out. A few hours of intentional effort in January can shape the behavior of your entire company for months, if not years. Skip it and you put your team at an information disadvantage you'll be fighting all year long.

The truth is, your kick-off is the highest-leverage meeting of the entire year.
Get it right and your team has the clarity to do their best work all year long. Get it wrong, and you're playing catch-up on culture and alignment for months.

I've worked with hundreds of CEOs on this. The ones who treat their kick-off like the Super Bowl moment it is? They never say die. They show up prepared, energetic, and locked in, and their teams follow suit. The ones who phone it in? They spend the rest of the year wondering why nothing is sticking.

I wrote a guide to follow in a recent newsletter. It includes the one thing your team needs from their leader going into the new year: Purpose, Direction & Progress.

link in the comments to go in depth on this topic 👍

This is where companies quietly fall apart:

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. 

You have to be intentional about learning the role. 

It’s not the same as being a founder. 

Two very different things.

***
Learn what the role of a CEO actually looks like in my recent article (link in comments)

How to speak like the top CEOs on the planet:

Most people communicate: 
- nervousness
- indecision
- selfishness

When they should be conveying: 
- conviction
- thoughtfulness
- partnership

Not all CEOs get it either, but the best certainly do. 

Here’s how 👇 

1/ Keep it clear & simple: Avoid jargon. Use plain English. Be yourself. Don’t over-share or talk in circles. Focus on nailing one main point but never exceed three. Don’t assume understanding. Ask the person if they get it.

2/ Speak with energy: Show enthusiasm & belief in what you say. Avoid fidgeting or whispering. Makes you look nervous. Stay solution-oriented. Don’t be a negative Nancy. You’ll demotivate everyone. Use storytelling to inspire & provide tangible examples.

3/ Talk like a partner: Say “we,” not “I”. Stay relatable to every level of the organization. Create a sense of shared ownership. Ask people: “What do you think?” Take people’s feedback seriously. Even if you make the final call.

4/ Communicate the ‘why’: Tie things back to mission & vision. Always explain reasoning behind major decisions. Help people understand company's progress. Create a sense of urgency when you fall behind. Say “because” more to force yourself to provide context to the team.

5/ Control your emotions: Never let feelings override the message. Stay composed under pressure. Don’t over-share and freak everyone out. But don’t sugarcoat things either. Be realistic & communicate a plan.

6/ Ask the right questions: Don’t pretend to have every answer. Find solutions through thoughtful questions. The best CEOs see themselves as detectives. Practice ‘5 whys’ asking why five times to find root causes.

7/ Guide, don’t dictate: Be a facilitator, not a dictator. Orchestrate debate & discussion. Pre-plan exercises that get people collaborating. Keep the room on track and constructive. Shape the discussion, don’t dominate it.


📌 ps if you want me to teach you how to do this at your company, check out Highland Academy: https://lnkd.in/eAVA5ekz

📌 📌 pps. if you enjoy my content, you'll love my free newsletter. Subscribe here: https://lnkd.in/e6ak5dbP

EOS and OKRs broke at scale. 

Here’s what replaced them.

I spent over a decade building Classy from a scrappy idea into a $100M+ company that processed billions in donations before we sold to GoFundMe.

As we scaled, one problem kept surfacing:
No operating system held up past ~$5M in revenue.

We tried OKRs. The product team loved them. But across the company they became too complex. Too many objectives, too many key results, quarterly resets, confusing grading. The system meant to create focus became a recurring distraction.

We looked at EOS. It was cleaner, but too prescriptive. And I didn’t agree with the idea that the founder should hand off operations to a “professional operator.” 

My belief is simple: The CEO must own the operating system.

There was also a deeper issue.

Classy was an impact company. Our mission wasn’t a slogan on a wall. It was the reason people showed up. We needed an operating system that connected purpose all the way down to daily execution, and not just tactical documentation.

So I built one.

It’s called the Northstar OS.

📌ps. If you want to dive into the Northstar OS framework, check out this article I wrote that breaks it down: https://lnkd.in/eDeRw6D2

pps. Sign up for my free newsletter here: https://lnkd.in/gXCsenmP

"Don't worry, you're gonna do great."

I was frozen in the green room at TEDx San Diego. My body felt like 1,000 pounds. I've only been a founder for a couple of years. Why am I giving a TED talk? People are going to laugh me out of this theatre.

An old man in the corner spoke up. That nudge got my legs working again.

I gave my talk. Came back dripping sweat.

"See, I told you you'd do great. You should be proud."

Then he walked on stage to give his own talk.

⁂

Years later, an advisor sent me a book that changed everything about how I manage people.

The One Minute Manager.

I googled the author. Ken Blanchard.

His face stared back at me.

The old man from my TED talk.

Here was one of the most successful business writers of all time, about to give one of his best talks ever, and he was focused on me.

That night I wrote Ken a thank you. He responded with equal grace.

⁂

The book became required reading for every manager at my company. Here are the 3 lessons that changed how I manage people forever:

1/ Great leadership is a side-by-side relationship. Not top-down. It's a partnership. When the organization wins, the people should win. Get this right and your people start managing themselves.

2/ Catch people doing something right. Positive recognition isn't soft, it's smart. People repeat what's recognized.

3/ Correct the behavior, not the person. Address mistakes quickly and specifically. End with reaffirmation. Every 1×1 becomes an opportunity to help people stay on track.

That night, Ken was demonstrating everything he'd later teach me through his book.

True leadership is the smallest acts of support, delivered at the right moment.

Full story + breakdown here:

Open article: 3 simple rules that changed how I manage people forever: by scotchisholm.com

3 simple rules that changed how I manage people forever:

Dave Kline

Become the Leader You’d Follow | Founder @ MGMT | Coach | Advisor | Speaker | Trusted by 250K+ leaders.

Hey, I’m Dave Kline.

I teach leaders how to build All-Star teams and level up their careers.

After decades of leading in pretty intense environments, from Bridgewater Associates to Moody’s Analytics, I know what it takes to be the manager your team remembers (for the right reasons).

Why I can help you is simple:

I’ve been through it.

And to prove it, here’s my background (by the numbers) ⤵️

2: Decades leading high-impact teams in asset management (Bridgewater), consulting (PwC), & financial services (Moody’s Analytics).

4: Years as an entrepreneur. My portfolio includes Skillscouter (an online course & career site), and MGMT Accelerator (a cohort-based management training course).

14: Cohorts of early-career leaders that I’ve taught at multiple companies.

100: Managers I recruited, onboarded & mentored at Bridgewater Associates.

1,000: Performance evaluations with grace and respect for stars and terminations alike.

205,000+: My community across LinkedIn & Twitter interested in management tactics & leadership lessons

385,000,000: My team’s top revenue year at Moody’s.

Now that we’ve covered the why, here’s the how:

- The MGMT Accelerator – an intensive management training course for both new and senior leaders
- MGMT Fundamentals – a course that covers all the need-to-know management basics for rookie leaders
- The MGMT Playbook – a weekly newsletter that gives practical management insights

Through our MGMT courses, my wife Marsden and I have played the assist with over 1,100 leaders so far, who’ve now learned how to:

- Practically tackle the most common leadership challenges
- Build their Management OS’s CODE (Coach, Operate, Delegate, Engage)
- Refine their individual leadership Decision-Making System

With our 30+ years of combined experience, you won’t just get our knowledge.

You’ll get to ask us questions directly and get access to coaching that’s more tailored to your own experience.

We always say – if we could do it like a dinner party, we would.

If you’re interested in leadership advice (that doesn’t just sound nice but actually works), drop me a follow – I post daily.

And if you like what you see, our MGMT courses could be just what you need to level up.

DM me if you’re interested.

Co-Founder

We created the MGMT Accelerator to help managers rapidly develop into trusted leaders by combining the art & science of management. 

This 4-week program consistents of eight 90-minute modules where I share the tactics I learned leading high-performing teams for 25 years. During each session, we tailor those insights together to build your personalized management system together. 

You'll learn alongside ~50 peers and become part of an expert community of more than 300 alums.

11 visuals that will transform your life
(simple changes you can start today)

These high-signal graphics were created by Ash Lamb.
Give him a follow!

1. Everything Is Built Brick-by-Brick
• The best time to start was 20 years ago
• The second best time is today

2. Don’t React, Respond
• You can’t control what happens
• You can always control your response

3. A Purpose Outlasts A Paycheck
• Teams need to know how to win
• The “why” keeps them playing

4. Focus On What You Can Control
• You are your best investment
• Put your energy into getting better

5. Saying “No” Is Your Superpower
• If everything’s a priority, nothing is
• “No” takes courage and creativity

6. Progress Over Perfection
• Waiting for perfect means waiting forever
• Act, learn, adjust, repeat

7. Conviction Beats Adversity
• Internal drive outlasts outside motivation
• No one’s watching as closely as you think

8. Imposter Syndrome Is A Growth Signal
• Growth happens at the edge of comfort
• The more time you spend there, the faster you grow

9. Closed Mouths Don’t Get Fed
• Not asking and “no” get you the same thing: nothing
• Asking gives you a shot at “yes”

10. Mistakes Are Not Failure
• The worst failure is never starting
• The second worst is quitting too soon

11. 80% Of Success Is Selection
• Effort matters, but it’s not enough
• Pick games you’re built to win

These 11 lessons are proof:
Small, relentless changes add up fast.

Which one hit home for you?
Drop your favorite in the comments ⬇️

♻️ Repost to help your network
🔔 Follow Dave Kline for more high-signal insights

 11 Ideas That Will Change Your Life

Most of what you do as a manager doesn’t matter.

These 5 levers will make or break you.

After 25 years of working with teams, 
The same pattern repeats:

Average managers try to do everything.
The great ones focus on what really matters.

These are the 5 factors every high-performing team gets right:

1. Clear Goal | Singular Focus
• If everything’s a priority, nothing is
• One mission everyone can recite from memory
• Make progress visible—post your key metrics publicly

2. Best People | Talent Density
• Filling seats with whoever’s available kills momentum
• Recruit constantly, raise the bar relentlessly
• Tap your top performers’ networks

3. Right Tools | Force Multipliers
• “We can’t afford good software” is an excuse
• Invest in systems that amplify talent
• Pre-approve any tool under $500/year

4. Least Friction | Ruthless Simplification
• “That’s how we’ve always done it” is a red flag
• Eliminate every unnecessary step and meeting
• Ask weekly: “What got in our way?”

5. Shortest Time | Speed as Strategy
• Waiting for perfect conditions means you’ll never act
• Run rapid experiments, learn fast
• Cut every cycle time in half—then do it again

The brutal truth:
Most teams have 3 out of 5 levers working.
Elite teams obsess over all 5, all the time.

One broken pillar pulls everyone down.

The diagnostic question:
Which lever is your bottleneck right now?

Fix that one first.
Everything else multiplies from there.

Want more practical frameworks like this?

Subscribe to the MGMT Playbook. 
My free weekly newsletter for leaders who want to level up.

https://mgmt.beehiiv.com

♻️ Share to help leaders focus on what matters
🔔 Follow Dave Kline for more practical leadership insights

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