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. 

🔥

The Founder Accelerator: Coach, Advisor & Mentor

Helping high-performing founders scale faster with absolute clarity

Founder

Treevotion

Sold in 60 countries during the first year of execution and planted +50K trees.

Planting 1 BILLION trees around the World in the most needed areas, building global awareness and consciousness on deforestation, driving people to help and share what they do in order to inspire to help everyday.

Every bracelet sold will fund the planting and follow up of 2 trees :)

Entrepreneurs'​ Organization

Co-Founded the non-profit EO (Entrepreneurs Organization) in Argentina. 

We grew the chapter to 120 members (all selling +1mm usd a year).

clickOn Argentina

co-CEO at Grupo clickOn managing 4 companies and +125 employees and USD 10MM in annual revenues :

1) clickOn (clickon.com.ar): #3 largest daily-deals site in Argentina, with +1.5MM users & +1MM transactions.

2) Agrupate (agrupate.com.ar): #2 competitor in Argentina, acquired in October 2015, with +2MM users and +1,5MM tickets sold.

3) Cupónica: (cuponica.com.ar): #4 competitor in Argentina, acquired in April 2015. +1MM users and 1MM coupons sold.

4) Silenzzo Mattresses (silenzzo.com): Vertical integration for the purpose of creating a mattress and sommier brand with nationwide reach.

Co-Founder & CEO

Founded and launched from scratch the startup clickOn.com.ar in Argentina.

Nowadays it’s present in 10 cities, has 2,500,000 users, 14k merchants, +90 employees and more than 2,000,000 coupons sold.

Company #2 in Argentina’s daily-deals ranking, that was acquired by Grupo Globo, the largest media company in Brazil.

clickOn Group has 3 companies under it’s portfolio: Coupons (clickon.com.ar); Travel Agency (clickon.com.ar/viajes); clickOn Discount Card (tarjetaclickon.com.ar).

Co-Founder & Sales Director

Anheuser-Busch InBev

Design and implementation of Sales structure hybrid models & Go-To-Market models nationwide.

Strategic Planning Coordinator

In charge of the largest Pepsi and Quilmes beer Distributor in GBA Norte (Buenos Aires), with 6000 PoS in charge, 1250 freezers, 19 million anual litres of beer and 11 of soft drinks. I coordinated the sales structure (45 salespeople, 6 supervisors y 1 sales manager).

Sales Manager Sr

For 7 months I was Senior Sales Supervisor for the Trade sales channel, in charge of 900 Convenience Stores and Groceries, and 6 moths for Self-Service stores the largest sales channel for AB-Inbev, with a team of 13 salesmen and repo and 250 PoS's.

Senior Sales Supervisor

"Jóvenes Profesionales" Program (Trainee / "Young Professionals") -  being one of the 25 selected out of 9500 applicants; we rotated between all marketing and sales areas in the company for 15 months. 
I spent 4 months knowing the 3 sales channels, 4 months as Marketing Assistant in Brahma beer and 6 months in Gatorade leading the "Propel by Gatorade" market launch.

Trainee - Joven Profesional

3x Founder | Founder Acceleration Coach | Helping high-performing founders scale faster with absolute clarity | Sold $65mm online

As a founder of 3 companies and 1 non-profit, with 2 successful exits, I’ve seen firsthand what it takes to grow a business.

I’ve also experienced the toll of stress, insomnia, and health challenges. I know how overwhelming it can be when scaling your business feels like an uphill battle.

In my 11 years with EO Argentina, I listened to the struggles of +100 successful founders (doing at least USD 1M a year in sales). I realized that beneath the surface, it’s often chaos: isolation, financial pressure, and fear of burnout. 

While most accelerators focus on startups, the truth is that, for businesses under $10MM in revenue, the biggest bottleneck to growth is you: the founder.

That's why I created Founder Accelerator: to empower the founders of renowned companies like Swag, Trading Company, Sancho Motors, Jams, Crawford Partners LLC, Lemon Basil, We Are Doers, and Mad Hatter LLC. 

My mission is to help them scale themselves first enhancing their clarity, focus, and efficiency, so they can grow their businesses with unparalleled speed and confidence.

Through personalized coaching, a 5-pillar playbook, and access to top professionals, we don’t just build businesses — we optimize the founder. 

If you're ready to scale your business while maintaining a healthy, balanced life, send me a DM and I’ll show you how Founder Accelerator can help you achieve both.

Ignacio Carcavallo

How to create a 3-year vision for your company:

Your team can only execute to the extent of the blueprint you give them.

The Vivid Vision exercise forces you to write it all down. 3-4 hours. 8 specific questions. No distractions. Then you share it with your team so they finally know what you're actually building.
That's how you stop micromanaging and start leading.

Want more founder systems to plan a strategic 2026? Join the Founder Accelerator Execution Group. Link is in my bio.

3x Founder | Founder Accelerator | Helping high-performing founders scale faster with absolute clarity | Sold $65mm online

How to extract your company vision from your head

Admitting you're drowning is f*cking hard. It's hard to say out loud:

"I want to stop sleeping 4 hours a night."

"I don't want to spend my life doing work I hate."

"I want to stop being stressed every single day."

"I need help. This is too much."

I’m grateful for the founders who are brave enough to admit that burnout and grinding isn't the life they want to build. Grateful for their trust. Grateful to watch them get their lives back.

You didn't start this business to be miserable. You started it for freedom. For control. For stability.

So don't let the journey drive you away from that.

🔥 For the next 5 days, I'm offering a 40% discount on 1:1 coaching sessions.

We'll identify your biggest blockers and map out exactly how to scale yourself so you can scale your business. 

Limited slots. 

Link in bio. Let's make a better 2026.

Discount

If you need someone to hold you accountable while you work on your visionary time and helps you execute your vision, the Founder Accelerator Execution Group is exactly what you need in 2026. 

You can check all frameworks and systems with the link in my bio. 

It’s the difference between grinding another year and actually scaling yourself and your company.

Here's a bucket of iced water before 2026 starts

How to build work-life balance as a founder (without sacrificing growth)

Most founders plan the business first, then try to squeeze their life into whatever time is left. There's never time left.

This isn't privilege. It's intentional planning. Your 2026 plan needs to start with how you want to live, not just how much you want to earn. 

Want help building a company that serves your life instead of consuming it? Comment “Coach”.

Work-life balance

How to create a 3-year vision so your team stops asking you about every decision

Your 3-year picture is the bridge between today and your 10-year target. It shows what needs to be true in three years to stay on track. And when you combine it with your core values, those two things become the filter for EVERY decision.

Now your team can make calls without you. You stop being the bottleneck.

This is Day 4 of the Vision to Traction Organizer. Follow for the full series on building a 2026 plan with real structure.

How to delegate before vacation (without your business falling apart)

If you can't take time off without checking your phone every hour, you don't have a delegation problem. You have a system problem.

This carousel shares the fix so you can actually disconnect.

Want the complete delegation framework? Link in bio for the Hiring & Recruiting Course.

Vacation - delegation

How to test skills in job interviews (instead of just asking about past experience)

You wouldn't hire a goalkeeper by asking "Tell me about your best save." You'd kick balls at them and watch them perform.

But most founders hire salespeople after hearing great stories about their past wins. No live demo. No skills test. Just confident answers and a polished resume.

Want the full framework for testing skills and values in interviews? Comment "Course" below.

No one would hire a goalkeeper based on...

Delegation is the hardest shift founders face when scaling.

Here’s what these 3 books will actually teach you:

1️⃣ Traction (Gino Wickman)

This is the operating manual for getting out of the weeds. 

- How to design an Accountability Chart so every role has one clear owner.
- How to use Scorecards to track weekly performance without micromanaging.
- How to run Level 10 Meetings so problems get solved in the room, not pushed back to you.

Instead of every problem coming to you, you’ll have structure so everyone knows their role and what they’re responsible for.

2️⃣ Topgrading (Bradford Smart)

Delegation fails if you hire the wrong people. Topgrading shows you how to identify, hire, and keep A-players so you can actually let go with confidence. 

- How to build Job Scorecards that define outcomes, not just responsibilities.
- The Topgrading Interview method to spot A-players vs. smooth talkers.
- How to make hiring a repeatable system so you trust who you delegate to.

3️⃣ 10x Is Easier Than 2x (Dan Sullivan)

This book flips the founder mindset: you don’t grow by doing more, you grow by doing less. It teaches you to focus only on your unique ability and delegate the rest. 

- How to identify your Unique Ability — the work only you should be doing.
- How to run a “Stop-Doing List” to decide what gets delegated or cut.
- How to shift from adding effort to multiplying results through leverage.

 If you’re stuck doing too much yourself, these 3 books are the fastest way to start building the muscle of delegation.

Which one are you starting with?

How to set business goals for 2026 (that your team can actually execute on)

The reason your 2025 goals failed isn't lack of effort. It's lack of clarity. Vague goals create hidden expectations. 

The fix: Write goals like a third party will audit them. No room for interpretation. No "what I really meant was..."

This is Day 5 of the Vision to Traction Organizer. We're building a 2026 plan that doesn't fall apart by February.

Follow for the rest.

New Client Testimonial: ⭐️⭐️⭐️⭐️⭐️

Feedback from Gustavo Scheveloff, Co-Founder & CEO of HiperPBX

—-

Thank you for your trust in Founder Accelerator.

Let’s keep pushing together 🚀

I talk to founders every week who are beating themselves up for not being further along.

Then I ask: "Where were you 3 years ago?"

The shift in their face is immediate. 

They forgot. They've been so focused on the gap between where they are and where they want to be, they stopped seeing how far they've actually traveled.

If that's you today - pause. Look back for a second. You've built something most people only talk about.

Happy Thanksgiving.

5 TED Talks that will build the successful founder mindset

Save this for when you need a reset.

1. Tom Röthlisberger → How to become a great founder
2. John Mullins → 6 tips on being a successful entrepreneur
3. Bill Gross → The single biggest reason why start-ups succeed
4. Roselinde Torres → What it takes to be a great leader
5. Kiki Ayers → How to know if you are meant to be an entrepreneur

These helped me dismantle the mental blocks that kept me stuck between $1-3M.

If you want to know which blocker is holding your business back today, check the link in my bio and take the quiz.

Most founders hire on gut feel. 

They like someone's energy. 

Their resume looks good. 

They have the right experience. 

Then 6 months later, they realize: This person is talented. But they're toxic. Or they don't make decisions the way we do. Or they're not aligned with how we actually work.

Skills got them in the door. But values are what make them stay or what destroy your culture. The big question us: HOW DO YOU TEST THEM? 

If you want the full system, check the course in my bio.

How to set core values for your company (that your team actually uses)

Stop inventing generic values like "transparency, execution, honesty." 

Here's what actually works: Extract values from your best players. 
The ones crushing it right now. Look at how they work, how they behave, what makes them different.

This is Day 1 of the Vision to Traction Organizer - the 2-page framework that replaces those generic planning templates you make every January and abandon by March.

Follow for the rest of the series. We're fixing your 2026 plan with real exercises, not theory.

How to differentiate your business from competitors (and stop competing on price)

If you're dropping prices to close deals, you don't have a positioning problem. You have a clarity problem.

Your 3 Uniques are the specific reasons clients choose YOU over everyone else. Not vague benefits. Concrete differentiators your team can sell and your clients can articulate.

This is Day 3 of the Vision to Traction Organizer. Follow for the full series on building a 2026 plan that actually works.

How to set a 10-year business goal (even when you can't predict next month)

Most founders avoid long-term planning because scaling feels unstable. But here's the truth: you DO have a vision. You just haven't written it down.

Your 10-year target doesn't need to be a fantasy. It needs to be bold, ambitious, but realistic. Something that makes it clear WHY you're putting in effort today.

This is Day 2 of the Vision to Traction Organizer. Follow for the full series. We're building your 2026 plan with real frameworks, not generic templates.

How to assign accountability for business goals

When you put two people on one goal, both assume the other is handling it. Then nothing gets done. Or it gets done halfway. And when you ask "who's responsible?" you get finger-pointing instead of answers.

One owner doesn't mean they do everything themselves. It means they're the single point of contact. The person whose name is on it. 

This is Day 6 of the Vision to Traction Organizer. Follow for the complete 2026 planning framework.

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