Scot Chisholm & Co. 

Every week I tackle management, operations & startup topics that are helping 100,000+ people become better leaders.

Scot’s Newsletter

Highland

Highland is a “school” & community for founders. If you're a founder/CEO, we should talk!

Founder & Chief Professor

Tall Timbers Holding Co.

A family office and holding company with wholly owned businesses, private investments, and property holdings.

Managing Director & Founder

GoFundMe

After the merger of Classy and GoFundMe, I’ve taken on a strategic advisory role to the CEO & executive team, mainly focused on longer-range product strategy and M&A

Strategic Advisor, GoFundMe & Classy

Classy

Founder & Strategic Advisor (Acq. by GoFundMe, 2022)

Founder & Chairman

Classy is a SaaS giving platform that powers the fundraising of over 10,000 nonprofit organizations. Classy is a certified B-Corp, has a team of 300+ people and has raised over $5 billion for social good since 2011.

CEO & Founder

In Classy’s earliest days, we hosted large scale fundraising events with the goal of connecting millennials with local nonprofits in the San Diego area.

CEO & Founder (pre tech company)

Haskill Creek

Haskill Creek is a new type of self-care store. Imagine a healthier & more holistic version of a Walgreens or CVS. Family owned business.

Co-Founder

ALBION SC

Albion Soccer Club is one of the top youth soccer franchises in the United States with over 10,000 players and hundreds of teams across the country.

Co-Owner

Save Farmland

Save Farmland is a nonprofit organization with a mission to protect and promote small farms in Flathead Valley, Montana, and beyond.

Abundant Montana

Board Member

AERO Montana

Abundant Montana (a program of Aero), makes it easy for anyone to find and choose local food in Montana.

Advisory Board

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

Multi-time founder but operator at heart. 

Industrial engineer and lean six sigma nerd by training. 

Now I write about management, operations & startup topics that are helping 200,000+ people become better leaders.

scotchisholm.com/newsletter


MY BACKGROUND ————— 

🚀 Founder of Classy, a SaaS platform for 10k+ nonprofits raising billions per year. 

🎗️Acquired by GoFundMe in ‘22 to create the largest giving platform in the world. Together we’ve raised over $30 billion for individual & nonprofit causes. 

🏔️ Founder of Highland, a private community & leadership “school” for high-potential founders. 

🏡 Co-founder of Haskill Creek, a much healthier version of a Walgreens or CVS. 

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

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

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


👇 WAYS TO CONNECT —————

→ Podcast / speaking oppty? email: partner@scotchisholm.com

→ Join my free newsletter: https://scotchisholm.com/newsletter-linkedin-profile

→ Check out my private community for founders: www.joinhighland.com

Scot Chisholm

Sh*tty managers ruin lives. 
Great managers change them. 

I’ve managed hundreds of people over the last 20 years. 

One of my biggest takeaways is the massive difference between an average manager and a truly great one. 

But, here’s the truth:

No one starts out as a great manager (literally no one). 

And, becoming a great manager can be learned by anyone. 

Just focus on these 12 habits:

1/ Provide business context
2/ Set high standards
3/ Take full ownership
4/ Focus (then focus again)
5/ Create operating cohesion 
6/ Lead with data
7/ But be decisive 
8/ Let your team make decisions
9/ Don’t give sh*tty feedback
10/ Take feedback like an adult
11/ Listen more than you talk
12/ Always be learning

The gap in quality managers is large, but the right behaviors are simple. 

Focus on these 12 habits daily and you’ll be ahead of 99%. 

What habits resonated most?
Let me know in the comments 👇

⁂

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

12 insanely simple habits to become a high performing mana

Leadership is misunderstood.

Building Classy taught me that the best leaders aren't necessarily the ones with the biggest titles, or the ones who can charm a room.

Some of the best leaders in our 300+ person company were individual contributors at the very bottom of the org chart. Young managers. First-time team leads.

Over the years I started noticing what made these unlikely leaders so effective. They had traits that, quite honestly, my executives lacked at times. Including me.

Over time I boiled them down to 10 core traits that our best leaders always exhibited. It’s no surprise they rose fast within the company. Many are still there today, 15 years later.  

The very best leaders: 

• Clarify - Never assume everyone understands
• Believe - Push forward when everyone doubts
• Adapt - Evolve rapidly without ego
• Anticipate - Solve problems before they explode
• Persist - Get kicked in the teeth, get up anyway
• Empower - Create leaders, not followers
• Own - Own failures without excuses
• Hold the line - When quality dips and others compromise
• Always Learn - Learn and grow faster than the company
• Lead by Example - Live values when no one's watching

Most leaders start off strong in a few, but not all of these traits. You must intentionally develop them over time. It's a lifelong thing. 

But many executives forget this. Maybe they were great once. But they start slipping. They stop learning. They get cocky. I've seen this too many times. 

I don't care where you’re at in your career. Keep these traits in mind. And never stop developing them. 

⁂

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Top 10 traits of the very best leaders:

Every high performance culture starts with this… 

I recently asked a founder about his culture. And he started talking about free lunches and other perks. 

This is not culture. 

He was a coaching client of mine, so I nicely explained… 

Here's what real culture looks like: 
→ A shared purpose. Everyone understands and resonates with the 'Why'.

→ Excitement about the future. The vision is clear to all and it creates an almost kid-like excitement about the future.

→ Strong empathy and trust. Great orgs know if you neglect empathy, trust evaporates.

→ The correct level of accountability. People know you're building a championship team.

→ Mutual respect and encouragement. High performers have admiration for each other.

→ Hunger to learn and improve. Without being asked. That's the diet of champions.

→ Aligned financial incentives. Compensation that's aligned to the organization's top goals.

→ Career mobility. Lots of opportunity, with clear expectations around advancement.

→ Work-life balance. Clear boundaries that are enforced across the org.

→ Pride in the work. Numbers one through nine create an amazing sense of pride. You'll find yourself bragging about work to complete strangers.


When you get the culture right, people are excited to show up, employees self-manage, and retention is extremely high. 

And great business results naturally follow.

 ⁂

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10 signs of great culture.

Most people waste their leadership meetings. 

Do this instead: 

When I was building Classy I got this meeting wrong for years. We’d talk about everything BUT the important stuff. Too much time wasted on low-level “issues”. Too many tangents and distractions. Everyone left feeling:

• Confused
• Misaligned 
• Unaccountable

I talked to advisors and scoured the internet for help. But it took loads of trial and error to land on a meeting structure that actually worked. We stuck with it for nearly ten years. 

One of the major improvements was focus. Teams spend months setting goals only to let them collect dust. Your leadership meeting should be your #1 checkpoint for progress. 

Once we got “tight at the top” as a leadership team, everything started to change. More results, less talk. It became the tip of the spear of our entire operating rhythm.

To this day, I call it your most important meeting. If I only had one, it’d be the leadership meeting. 

The entire leadership team meeting structure is in the carousel. Copy it for your own company and let me know what you think. 

⁂

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How to nail your  leadership meeting every time:

Most people think goals fail because the team screwed up. 

They’re wrong. 

99% of goals fail because of poor leadership.

It doesn’t matter what framework you use…

→ OKRs
→ Rocks
→ SMART

If you’re sloppy with your approach, the company won’t hit its goals. 

That’s on you. 

I learned this the hard way, running a company with hundreds of people. 

Now I see it working with nearly 100 CEOs across all industries. 

Here are 7 non-negotiable rules that will make your goal-setting 10x better…

(regardless of your framework) 

⁂

Rule 1 –  
Focus (then focus again):

• Maximum three goals, period
• Goals aren't task lists
• Everything priority = nothing priority

Rule 2 – 
Always be measurable: 

• Three metrics maximum per goal
• Measure outcomes, not tasks
• "$1M ARR" beats "update deck"

Rule 3 – 
Challenging but realistic: 

• Impossible goals kill momentum
• Stretch without delusion
• No sandbagging, mutual accountability

Rule 4 – 
Never forget the ‘why’: 

• No context leaves team guessing
• Each goal deserves a 'why'
• 1-3 sentence rationale

Rule 5 – 
Track consistently:

• Break annual into monthly
• Weekly red/yellow/green updates
• Never leave dashboards stale

Rule 6 – 
Create accountability:

• Use leadership meeting
• Address every yellow or red
• 20% status, 80% solving

Rule 7 – 
Align incentives:

• Pay goals to comp
• Ignore the OKR purists
• Bonus plan is perfect for this

Does this resonate? 
What rules would you add?
Let me know in the comments 👇

 ⁂

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How to actually achieve your company goals in 2026

If there's one thing you do on Linkedin today... 

I'd be forever grateful if you'd consider applying, or sharing this role with someone you really respect. 

Christopher Himes & I started dreaming up this company about a year ago.  Now the dream has turned to reality. 

With a fresh round, a tiny team of insane talent, and a massive opportunity in front of us... 

We. are. ready. to. go!

Who wants to join us? 

p.s. We're not listing this company as "stealth" because that's dumb. But you'll learn way more about the market, opportunity and product when you apply. Trust me its badass. 

🔥

Fractional COO Helping Visionary CEOs Build Attractive Companies and Cultures | Integrator for Companies Running on EOS

You’re reading this because…

→ You’re a business owner who’s ready to elevate your ops, revolutionize your workflow, and build a high-trust team. 

→You’re looking for your number 2 to take the business to the next level. 

→ You’re an Integrator who wants to lead with clarity and confidence.

→ You’ve implemented EOS®, but something still isn’t clicking.

Without strong operational systems, businesses stall, leaders burn out, and scaling feels impossible.


That’s where I can help.


Who I Work With:
Visionaries:
 → You want to focus on strategy and innovation, not constant fire-fighting.
 → I step in as your operational right hand to implement systems, hold the team accountable, and drive your vision forward.

Integrators & Ops Leaders:
 → You want to build a scalable, high-impact business that’s rooted in systems, not stress.
 → I’ll teach you how to lead execution, master EOS®, and position yourself as a strategic partner to CEOs.

Implementers:
 → Together, we create clarity + accountability that sticks.
 → You’ll not only learn EOS, you’ll actually live it.

I want to help your business scale.

Client Testimonials:

“Raquel skillfully guided our team in embracing the EOS model, fostering a genuine sense of shared accountability. The change in our internal and cross-departmental communication has been remarkable – truly a night-and-day improvement under her leadership. It's no exaggeration to say that thanks to Raquel's stewardship, the Reliance Property Management Group of today is fundamentally stronger and more cohesive than we were a year ago.”


"Raquel has the ability to understand deep long-term vision and translate that into small incremental steps that have a large impact on an organization. Her wisdom is evident in every decision as she earns loyalty and respect quickly. She has an uncanny skillset to see through the maze of issues, address the specific things that will have the largest impact, and implement a solid plan to execute. With her help, we were able to address major flaws in our business model and develop a new strategy that gives us the potential to 10X the size of the company. Being a visionary leader made it hard on our employees to translate my vision into tangible goals. Raquel was the perfect person to take the vision and give clarity to our team on how to deliver results."

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Scot Chisholm

Raquel Castillo, MBA

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The Battle

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Raquel Castillo, MBA

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Scot Chisholm's LinkedIn Performance

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