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:

𝗧𝗿𝗮𝗻𝘀𝗳𝗼𝗿𝗺𝗮𝘁𝗶𝘃𝗲 𝗚𝗿𝗼𝘄𝘁𝗵 𝗖𝗼𝗮𝗰𝗵𝗶𝗻𝗴 𝗳𝗼𝗿 𝗙𝗶𝗿𝘀𝘁-𝗧𝗶𝗺𝗲 𝗙𝗼𝘂𝗻𝗱𝗲𝗿𝘀
It’s not just about scaling your business.
It’s also about scaling you.
From Fortune 500 companies to fast-growing startups, I’ve coached leaders at every stage. Today, my mission is focused: helping first-time founders scale themselves as fast as they scale their companies.
 
𝗠𝘆 𝗙𝗼𝗰𝘂𝘀
Your startup can only grow as fast as you do. As a first-time founder, you’re under pressure from investors, your team, and your family—all while learning on the fly skills that others spend decades mastering. Whether you’re raising capital, hiring your first team, or pushing toward product-market fit, I help you close the gap between where you are and where your company needs you to be.
 
𝗪𝗵𝘆 𝗠𝘆 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵 𝗪𝗼𝗿𝗸𝘀
I bring 20+ years of coaching 10,000+ leaders, founder experience, and cutting-edge insights from neuroscience and behavioral psychology. The result: a proven path to accelerate both personal and company growth. My frameworks help you:
• Transform self-doubt into clarity and influence
• Build and inspire high-performing, durable teams
• Raise capital while staying true to your vision
• Create sustainable success without burnout
• Leverage your existing strengths while closing critical skill gaps
• Grow yourself as fast as your company 
 
𝗪𝗵𝗼 𝗜 𝗦𝗲𝗿𝘃𝗲
My one-on-one clients are founders who:
• Want tailored, responsive coaching that meets them where they are
• Care deeply about building strong teams and cultures
• Aim to create both impact and enterprise value
• Refuse to accept that success means sacrificing their families, health, or lives outside the company
• Are willing to grow personally and professionally to become the leader their company needs 
 
𝗥𝗲𝗮𝗹 𝗜𝗺𝗽𝗮𝗰𝘁
From doubling revenue to unlocking fundraising rounds to transforming team dynamics, my clients consistently achieve breakthrough results—while building lives they actually want to live.
 
𝗪𝗮𝗻𝘁 𝘁𝗼 𝗖𝗼𝗻𝗻𝗲𝗰𝘁?
Visit www.andrewpoles.com/contact or DM me here.

Andrew Poles

We use the word “complete” all the time.
But most people confuse it with “finished.”

They’re not the same.

You can end a relationship and still be carrying it.
You can be in an ongoing partnership and feel fully clear.

Completion is a function of how you relate to reality - not a status update.
In this clip (from my conversation on the Sleep Is A Skill podcast with Mollie), I break down what I mean by being complete - and why it has real implications for how you live, lead, and even sleep.

Coaching first-time founders to grow themselves and their companies | 3x Founder | 22+ years coaching partners like NASA, Dell, Schwab + 10,000 people worldwide

What does insomnia have to do with integrity?
More than most leaders realize.

I once worked with a man who had slept 1–2 hours a night for years. His health was at risk. After doing deep completion work in his relationships and life, he slept 8–10 hours for the first time in decades.

There’s a connection between how complete you are and how well you sleep.
And more than that - your sleep may be a lagging indicator of how powerfully you’re living and leading.

If this resonates, I unpack it further on the Sleep Is A Skill podcast with the amazing Mollie Eastman, episode linked below.  

Sometimes it’s not a sleep issue.
It’s a leadership issue.

#Leadership #ExecutiveCoaching #SleepIsASkill #FounderHealth #Integrity

This is the part of leadership most spreadsheets can’t capture. When behavior stops making sense, there’s almost always unseen pressure in the room.
What stands out here is the refusal to confuse kindness with lowering standards. Real leadership is keeping the bar high AND removing shame from the climb.
Culture isn’t what you say you value - it’s how safe it feels for people to be human while doing hard work.

3 Exits | Founder @ Humble | Strategic Partner @ Loud | Follow for Self Improvement, Growth Strategy & Being A Better Human | Entrepreneurship Coach & Mentor

You have no idea what people are dealing with.
Not even close.
And that’s ok.

Because you just have to be kind.

The person who snapped in your meeting might have a kid who’s struggling.

The one who “doesn’t care anymore” might be keeping a marriage together with duct tape.

The quiet one who missed a deadline might be dealing with a parent who’s fading, fast.

Work makes it easy to pretend everyone is a machine.

Metrics. Output. Deadlines. Slack green dots.

👉 But leadership is what you do when the spreadsheet stops explaining the behaviour.

Bad leaders get this part wrong: 

They think kindness is a personality trait.

It isn’t.
It’s a professional skill. 
And it’s different to being NICE.

Kind isn’t soft.
Kind is controlled.

Nice avoids the hard chat.
Kind has it, without making the person feel small.

Nice lowers standards so nobody feels uncomfortable.
Kind keeps standards high and removes the shame from getting there.

I learned this the hard way building companies from nothing.

⚠️ When you’re under pressure yourself, your instincts get ugly, and you start to:
Push harder. Watch closer. Assume the worst.

It feels “productive”.

It’s usually expensive.

Because people don’t leave jobs first.
They leave the feeling of being misunderstood.

So if you want a practical way to lead like a grown up, try this:

Before you judge the performance, check the pressure they are under.

BUT, a simple “You alright?” is not leadership.
Anyone can say that.

📌This is leadership:

1.	Ask a better question
“What’s taking up headspace right now?”
It gives them a door that isn’t dramatic.

2.	Offer a real option
“Do you want time, help, or privacy?”
Most people just need one of the three.

3.	Separate the person from the work
“You’re not your output. Let’s fix the work.”
That one sentence changes everything.

4.	Adjust the load, not the standards
“What do we de-scope for 7 days?”
Pressure without control creates mistakes.

5.	Protect them in public, coach them in private.
If you correct someone publicly, you teach the whole team to hide.

None of this is “being nice”.

It’s how you keep good people good.

Your culture isn’t your values on a Notion page.
It’s how safe it feels to have a bad week around you.

So yes, you seriously have NO idea what people are dealing with.

Lead like you know that.

-
♻️: Repost to inspire.
➕: Follow Charlie Lass.

Most founders don’t get stuck because things are hard.
They get stuck because of the story they tell themselves about why things shouldn’t be this way.

Loss. Missed signals. Bad hires. Broken trust.
The pain is real — but the suffering is optional.

This week I'm sharing about how leaders unknowingly trap themselves after setbacks, and how dropping one word can unlock clarity, resilience, and forward momentum.

If you’ve been carrying something heavy lately, I hope this offers you some needed clarity.

Sadness: Yes. Suffering: No. Over the last few weeks, several founders I coach have been moving through loss. Not just personal loss — though that’s b

Open article: The “Should” Trap in Leadership by Andrew Poles • 4 min read

When Ken Cox and I were talking recently on the Clicks and Bricks podcast, we kept circling back to something that doesn’t get talked about enough in business:

Your company grows at the speed of your own growth.

Not just revenue.

You can still be making money and feel something in the business has stalled.

Energy drops. Culture gets stale. Decisions feel heavier.

I’ve lived that.

In my first business, I thought learning business meant learning tactics. Strategy. Sales. Operations.

And yes — you do have to learn the “game.”

But what I didn’t understand then was that every ceiling I hit in the business was connected to a ceiling in me.

Fear I hadn’t dealt with.
Conversations I didn’t want to have.
Identity I hadn’t owned yet, or hadn't generated the courage to let go. 

Ken asked me about authenticity and about “next right actions.”

For me, performance really comes down to that:

What is the next right action of integrity here?
Not the most comfortable action.
Not the one that protects your ego.
The one that’s actually right.

That’s where growth happens.
And when that shifts, the business shifts.

If you’re a founder, especially early-stage, I think you’ll appreciate how deep this conversation goes. 

I'll put the link to the full episode in the comments.

Most founder tension isn’t about strategy.

It’s about what no one is saying.

When something is clearly impacting performance–but everyone is pretending it’s not–trust erodes, capacity drops, and the team feels it.

This is about how to name the “boulder in the room” without creating drama, shame, or overcorrection.

If you’ve ever:
-Avoided a hard conversation at the top
-Worried about overstepping vs. under-supporting
-Felt silent tension on your leadership team
-Tried to protect the business without adding pressure

This is for you.

A founder asked me this week how to support a co-founder going through a deeply disruptive personal situation. You know the kind. Sleep off. Nervous s

Open article: The Boulder in the Middle of the Room by Andrew Poles • 5 min read

Your calendar is lying to you.
Not because you’re incapable - but because it’s built on optimism, not reality.
If your day assumes you’ll get everything done, with no interruptions, no fatigue, no tradeoffs… that’s a fantasy, not a system.
You don’t need better memory.
You need a structure that maps real work to real time - and forces honest choices.
High performance starts with a calendar that tells the truth.
Where is yours overpromising right now?

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