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. 

🔥

Justin Mecham

Founder & CEO (company was acquired)

Founder creatyl: The Only Platform Creators Need to Make Money | Join My Newsletter & VIP creatyl Community | Follow For Daily Lessons On Leadership, Productivity, Entrepreneurship, AI

👉 Join My Full Potential Zone Newsletter & VIP creatyl Community 👈

I just wanted to make money online and build my personal brand—share what I know, offer coaching, sell digital products, offer courses, run a community.

But within weeks, I had 8 tools and was spending almost $1,000/month.

One for courses. One for emails. One for booking. One for a community. Another for payments.

I needed one clean, simple platform, built by someone who actually gets it. 

But I couldn’t find it…soooo, I built it.

Meet creatyl—built by a creator, for creators, coaches, consultants, and anyone looking to make money online.

🎯 Sell digital products, coaching sessions, or courses
💬 Run a paid community or membership
📬 Launch your newsletter and automate your emails
💡 Tap “Create with AI” to create & launch any of these in minutes
💰 Get paid & track every sale
🧩 And manage it all in one place

It’s not just amazing software.

Inside there is creatyl University, where you get hundreds of step-by-step training guides/videos, smart templates, and expert prompts to help you build faster and better.

Plus you will join the VIP creatyl Community.

Most creator/personal brand/business growth communities cost $800 to $3,000/month.

creatyl’s VIP Community is INCLUDED in your creatyl subscription! 

You will have weekly live calls with me and other top creators.

Plus daily/weekly expert tips and secrets, real-time feedback, and personal strategies to make sure you always know what to do to be successful, and SO much more.

Whether you’re a creator, coach, consultant, wanting to start a business, or looking for the perfect side‑hustle… 

Whether you’re just starting, scaling, or ready to leave your 9‑5… 

Whether you have a million followers or just a few...

If you’ve ever said: 
“There’s got to be a better way to do this.”

You were right.

creatyl is the better way.

→ Try it free at creatyl.com (see link in my featured section)

→ And join my free newsletter where I give weekly tips and growth tools on all of this plus entrepreneurship (see link in my featured section).

Vice President of Operations

•	Oversee Operations, Strategy, Customer Experience, Contact Centers, Sales, Fulfillment, and Service Centers (Domestic & International; B2C & B2B).
•	Manage budget, prepare financials, reporting, analysis, and recommendations.
•	Collaborate with the executive team in setting and driving the organizational vision, operational strategy, and hiring needs.
•	Translate the strategy into actionable goals for performance and growth, helping to implement organization-wide goal setting, performance management, and annual operating planning.
o	Introduced 5 new sales channels.
o	Started in-house Service Centers and launched new warehouse.
•	In charge of Customer Experience: Introduced Net Promoter Score (NPS) and closed-loop process - now ranked higher than brands like Apple and Amazon.
•	Manage culture and employee experience, building a highly inclusive culture that ensures team members thrive and organizational outcomes are met.
•	Identify areas of process enhancement, implementing automation tools and best practices to increase efficiency and quality.
o	Introduced “Personal Shopping” experiences that customers can have with our associates.
•	Maintain and build trusted relationships with key customers, clients, partners, and stakeholders, ensuring high customer satisfaction and retention rates.
•	Revised Customer Service to be WOW! Center where associates are given the training, processes, and empowerment to do what is best for the customer the first time.
•	Negotiate contracts with vendors, suppliers, and service providers to secure optimal terms and conditions.

The danger isn’t what happened—

It’s what we assumed about it:

Here’s how the ladder 
of inference traps us:

1️⃣ Fact → Someone misses a meeting.
2️⃣ Detail → They didn’t answer my email.
3️⃣ Meaning → They must not care.
4️⃣ Assumption → They ignored me on purpose.
5️⃣ Conclusion → They’re unreliable.
6️⃣ Belief → They’re not committed.
7️⃣ Action → I exclude them from future work.

The problem? 

At every step, the truth
drifts further from reality.

Fix it:
• Stick to facts, not opinions.
• Pause before assuming intent.
• Stay open to new information.
• Check beliefs before acting.

Use my sheet to see how to catch 
yourself before assumptions cost trust.

Check the facts before you move.

🧲 I’m teaching a free live workshop to
build a lead magnet WITH you live on the call.
➡️ Save your seat: https://lnkd.in/gpD5ywmG

______________________

👇 Want PDFs of my top infographics + growth tools?
👉 Go Here: https://lnkd.in/g2xbnwhp 

Please repost to help others out there! ♻️

The Digital Products Guy | I help creators, coaches, & consultants build digital product empires | Founder creatyl.com | Learn all my secrets in my newsletter below 👇

You don’t lack time—

You're wasting it on the wrong things:

And that’s not your fault.

Most people were never taught how to
manage time—only how
to react to it.

But time isn’t something to manage.

It’s something to protect.

Here are 11 simple systems that protect
your hours and take back your day:

☑️Pomodoro → 
• 25 minutes on, 5 minutes off.
• Do 4 rounds, then take a longer break.

✅3-3-3 Rule → 
• 3 hrs deep work.
• 3 quick tasks.
• 3 maintenance tasks.

☑️Eisenhower Matrix → 
• Do, decide, delegate, delete.
• Sort by urgent vs. important.

✅2-Minute Rule → 
• If it takes less than 2 minutes, do it now.

☑️ABCDE Method → 
• Rank tasks.
• A = must, E = eliminate.

✅Eat the Frog → 
• Tackle your hardest thing first.

☑️Time Blocking → 
• Assign hours for each task.

✅Kanban Board → 
• Visualize tasks.
• To do → Doing → Done.

☑️80/20 Method → 
• Focus on the 20% that 
creates 80% of the results.

✅Getting Things Done → 
• Capture tasks and organize.
• Then, reflect and repeat.

☑️MSCW Method → 
• Must, Should, Could, Won’t. 
• Prioritize fast.

The hours are already there. 

The system you choose decides whether 
they move you forward or keep you stuck.

📌 Want PDFs of my infographics + growth tools?
⏩ Go Here: https://lnkd.in/g2xbnwhp

_____________________

🛠️ Build your digital product with me live - 
👉 Learn more here: https://lnkd.in/gqe24hWi 

Please repost to help others out there! ♻️

You’re not “too emotional”—

You’re carrying two realities at once:

Most people try to control what they feel.

But emotions were never meant to be caged.

They’re not flaws to fix—

They’re data.

They’re how your body and brain
speak truth before words do.

Look closer and you’ll find your most
powerful traits aren’t pure—
they’re layered.

For example:

🟠 Joy + Sadness = Bittersweet
🟡 Anger + Compassion = Assertiveness
🟡 Hope + Doubt = Determination
🟠 Confidence + Vulnerability = Courage
🟡 Peace + Uncertainty = Resilience

This mix? That’s not a malfunction.

That’s your wisdom forming in real time.

It’s how you learn what matters—
what hurts, what heals, what’s next.

And once you can name it,
you can work with it.

Self-awareness starts where judgment ends.

Feel first. Then listen.

That’s how emotion turns into wisdom.

📚 I'm hosting a free online workshop to
build a digital product WITH you live.
➡️ Save your seat: https://lnkd.in/g3tvdU8B

______________________

📂 Get my full library of free tools — guides, templates, PDFs, and videos:
👉 Go Here: https://lnkd.in/g2xbnwhp

Please repost to help others out there! ♻️

Random chats aren’t leadership—

This is what real 1:1s look like:

1-on-1s shouldn’t be random check-ins—

They should be a system that
builds clarity, trust, and growth.

Here’s how to make them work:

Daily
🟡 Write your top 3 tasks for tomorrow
🟡 Note 1 blocker or question you have
🟡 Track your energy level and one win

Weekly
🟠 Start with last week’s wins + 3 new goals
🟠 Ask: “What’s in your way this week?”
🟠 Each trade one piece of feedback

Monthly
🔴 Talk about clarity, growth, and energy
🔴 Set a small goal with a clear next step
🔴 Review what’s working and what’s not

Try this 3-part 1:1 rhythm:
1️⃣ Daily: Quick notes on wins, blocks, and focus
2️⃣ Weekly: Feedback and fast problem-solving
3️⃣ Monthly: Big-picture clarity and growth

Great 1:1s don’t need more time —
They need a better reason to meet.

Clarity builds momentum.

Trust builds performance.

Great 1:1s build both.

🧲 I’m teaching a free live workshop to
build a lead magnet WITH you live on the call.
➡️ Save your seat: https://lnkd.in/gpD5ywmG

______________________

👇 Want a PDF of my top infographics? 👇
Go Here: https://lnkd.in/g2xbnwhp 

Please repost to help others out there! ♻️

The Digital Products Guy | I help creators, coaches, experts create & sell digital products, courses, & memberships | Founder creatyl.com | 4 exits | Join creatyl + newsletter below 👇

Self-belief isn’t something you feel—

It’s something you build:

And most people build it backwards.

They wait until they “feel ready.”

They chase confidence like it’s a finish line.

But belief doesn’t show up first.

Proof does.

Here’s what the path really looks like:

🔴 Doubt Zone
• Feels safe, but keeps you stuck
• You overthink, compare, and feel foolish
  
🟠 Resistance Zone
• Critics get loud
• You celebrate effort, but progress feels slow

🟡 Skill-Stacking Zone
• Small wins stack
• You learn one thing at a time
• Support makes belief grow

🟢 Belief Zone
• You take bold action
• Trust yourself
• Help others believe too

🔁 The Loop That Builds Belief
• Notice doubt — don’t follow it
• Act before you feel ready
• Repeat. Belief grows with proof

Every action is proof.

And proof builds belief.

You don’t need to wait to believe.

You need to move.

📚 I'm hosting a free online workshop to
build a digital product WITH you live.
➡️ Save your seat: https://lnkd.in/g3tvdU8B

______________________

🧰 Want my entire toolbox for free — checklists, templates, PDFs, and trainings?
👉 Go Here: https://lnkd.in/g2xbnwhp 

Please repost to help others out there! ♻️

Metrics don’t replace leadership—

They reveal it:

Great leaders don’t guess,
they measure what matters.

Because what you track 
shows what you value—

And what you value 
shapes your results.

Here are a few simple ways 
to track better leadership:

🟥Strategy
• Measure if projects actually make an impact.
• Watch your market position and key changes.

🟨Engagement
• See how connected your team feels.
• Track why people stay or leave.

🟦Efficiency
• Find slow systems and fix them.
• Cut waste and track savings.

🟩Finance
• Track growth each month.
• Know your profit, not just revenue.

🟪Innovation
• Track new ideas and results.
• Spot untapped markets.

Should you track all of these?

No - choose what best fits your needs.

Clarity turns effort into progress.

Measure what matters, 
not what’s easy.

Because what you track 
becomes what you achieve.

📎 I built a free library for you — PDFs, frameworks, and short trainings:
➡️ Go Here: https://lnkd.in/g2xbnwhp

_____________________

🛠️ Build your digital product with me live - 
👉 Learn more here: https://lnkd.in/gqe24hWi 

Please repost to help others out there! ♻️

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The Battle

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