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:

This is the part of leadership no one prepares you for…

Going from IC to manager is hard.

But becoming a manager of managers is brutal. 

You’re no longer managing the work… you’re managing the people who manage the work.

Vanilla management advice no longer works. Instead, focus on these 7 things:

→ Provide clarity and context. If they don’t have context, they can’t give context. And their teams will be flying blind. Make sure your managers always know: Why are we here? Where are we going? How are we doing? Your job is to arm them with the information they need to lead.

→ Work through, not around. When someone skips your manager and comes to you with a problem, resist the urge to solve it on the spot. This robs your manager of the chance to learn and improve themselves. Listen. Ask questions. Then loop your manager in to address it. Build leverage through them, not around them.

→ Set a team rhythm. Establish a recurring cadence with your managers. Weekly or bi-weekly team meetings work best. Create a high-performance environment that focuses on progress against goals. But feels safe for the managers to help each other, unblock projects and always stay aligned.

→ Create additional checkpoints. Checkpoints ensure your managers stay on top of things. Your early warning system. 1x1s for coaching and calibration. Quarterly reviews for deep dives. Occasional skip-levels to stay connected. But don’t overdo your 1 on 1s. Great managers shouldn’t need tons of special attention.

→ Don’t do their job for them. When your manager is struggling, it’s tempting to pick up their slack. Don’t. They need to own the outcome fully. You can coach them, help connect the dots, resource things. But don’t do the work for them. They’ll never develop into a strong manager this way.

→ Create P2P accountability. Peer-to-peer accountability is stronger than top-down. Great managers don’t want to let their peers down. Review each other’s goals. Share progress openly. Set standards together. Your team helps you keep the bar up for everyone.

→ Avoid over trusting. It’s tempting to say: “They’re experienced, they’ll figure it out.” This is blind faith. When a manager is sending off smoke signals through any of the prior steps. Missing goal after goal. Showing up weak at checkpoints. With no correction on the horizon. It’s time to take action. Don’t trust forever. The buck still stops with you.

⁂ 

Putting it all together... 

How to manage managers: 

• Provide context
• Work through manager
• Set team rhythm
• Create checkpoints 
• Don't' do their job
• Create p2p accountability 
• Avoid over-trusting

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How to manage managers (even as a newbie)

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. 

🔥

Ranked #1 German LinkedIn Creator | "Ultraproductive" Coach & Author at Portfolio Penguin | Follow for posts about habits, productivity & personal development

Follow for posts about habits, productivity & personal development.⚡️ 

I'm a scientist-turned-writer and coach who sets up executives, entrepreneurs and leaders in high-stress environments for long-term success. 

I was ranked #1 German LinkedIn Creator in Productivity & Personal Growth by Favikon. My forthcoming book Ultraproductive — co-authored with Eric Partaker — will be published in 2026 by Portfolio Penguin. 

Here are 3 ways I can help you:

1) BEYOND PRODUCTIVITY [NEWSLETTER] 📩 

Most people don't know how to build habits for sustainable peak performance. That’s why I write a monthly newsletter that teaches these habits. With 2 minutes of reading time, you’ll get one simple tip to go "Beyond Productivity" — and learn both why it works and how to implement it.
 → Try it for free: www.ultraproductive.com/newsletter

2) ULTRAPRODUCTIVE [BOOK] 📖 

In our forthcoming book, Eric and I provide a roadmap for achieving sustainable peak performance by strategically optimizing focus, sleep, and stress management — 90 minutes at a time.
 → Sign up for potential early-bird discounts: www.ultraproductive.com/book

3) BECOMING ULTRAPRODUCTIVE [COACHING] ♟️ 

We also created a 1:1 coaching program to help executives, entrepreneurs and leaders become Ultraproductive. In the program, I provide the support, systems and accountability to double your productivity and master stress in 3 months.
 → Learn more and book a free call here: www.ultraproductive.com/coaching

✍️ PS: Get in touch about sponsorships (for my newsletter and LinkedIn posts):
https://www.passionfroot.me/dr.-christian-poensgen

Dr. Christian Poensgen

I used to think productivity meant doing more.

Then I realized: it's about doing less, but better.

That's when the 80/20 rule changed everything for me.

Here are 10 ways to apply it:

1) Tasks ✅
↳ Pick the one task that will make your day a success.
↳ Do it first before anything else (including email).

2) Strengths 💪
↳ Use the skills that give you the biggest return.
↳ Delegate or outsource what drains you.

3) Activities ⏳
↳ Cut the 20% that waste most of your time.
↳ Do more of what brings real progress.

4) Decisions 🎯
↳ Make the choices that shape your long term path.
↳ Simplify or skip decisions with little impact.

5) Learning 📚
↳ Study the ideas that matter most to your goals.
↳ Review often so the lessons stick.

6) Habits 🔄
↳ Build routines that boost energy and clarity.
↳ Drop habits that limit your potential.

7) Relationships 🤝
↳ Spend time with people who lift you higher.
↳ Reduce time with those who drain you.

8) Wardrobe 👕
↳ Choose clothes you love and wear often.
↳ Remove pieces you never reach for.

9) Health 🧘
↳ Prioritize sleep, good food, and movement.
↳ These create most of your daily energy.

10) Possessions 📦
↳ Keep items you use often and value.
↳ Clear the rest to free space and mind.

- - - -

Want to see real progress in your life?

Shift from "do more" to "do less, better".

What's one 80/20 tweak you'd add to this list?

- - - -

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I've coached hundreds of high performers.

7 patterns that separate the good from the great:

1) Disciplined
↳ Hard choices, easy life. Easy choices, hard life.
↳ Follow the plan even when it stretches you.

2) Growth minded
↳ Treat feedback as fuel rather than a final judgment.
↳ Action creates clarity far more than overthinking.

3) Opportunity seekers
↳ Stress is practice for the next level, not a punishment.
↳ Ask yourself: What lesson is this challenge giving me?

4) Laser-focused
↳ Carve out one deep work block of 60-90 mins a day.
↳ Protect your attention (your most valuable resource).

5) Emotionally intelligent
↳ Label emotions to reduce their power over you.
↳ Slow down, breathe, and choose your response.

6) Self-confident
↳ Speak to yourself the way a good friend would.
↳ Use journaling to reinforce progress and identity.

7) Eternal learners
↳ Each misstep holds a lesson that can level you up.
↳ Replace “I can’t” with “I am not there yet.”

- - - -

The people who rise to the top share three traits:

→ Clarity about what they want
→ Calm in the face of chaos
→ Habits that compound

Success does not appear out of nowhere.

It is built,
one day at a time,
one choice at a time.

What would you add to the list?

- - - -

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In leadership, the words you choose are everything.

8 phrases that distinguish leaders from bosses:

1/ “I trust your judgment” 🤝
↳ Builds confidence and ownership.
↳ A boss says: “Do it my way.”

2/ “Let’s learn from this” 📘
↳ Turns mistakes into momentum.
↳ A boss says: “Don’t mess up again.”

3/ “How can I support you?” 🛠️
↳ Shows commitment to your team’s success.
↳ A boss says: “You’re on your own.”

4/ “Thank you for your efforts” 👏
↳ Makes people feel seen and valued.
↳ A boss says: “That’s what you’re paid for.”

5/ “I believe in you” 🔥
↳ Sparks confidence and motivation.
↳ A boss says: “You need to prove yourself.”

6/ “Let’s solve this together” 🤝
↳ Fosters teamwork and shared accountability.
↳ A boss says: “Figure it out yourself.”

7/ “What are your thoughts?” 💡
↳ Invites input and genuine collaboration.
↳ A boss says: “This is how we’ll do it.”

8/ “Great job on that” 🎉
↳ Boosts morale and reinforces progress.
↳ A boss says: “We need to do more.”

- - - -

What separates leaders from bosses?

Bosses push people down.
Leaders lift them up. 

Agree? Disagree?

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I used to fall for all of these every single day.

6 habits quietly holding you back:

(and how to break them):

1) 24/7 availability 📱
↳ Always being available guarantees burnout.
↳ End your day with Cal Newport’s shutdown ritual.

2) Hustle culture 🏃‍♂️
↳ Busyness does not equal results.
↳ Protect your sleep and take real breaks to recharge.

3) Multitasking 🚫
↳ Task switching cuts efficiency in half.
↳ Timebox everything, including focus and breaks.

4) Perfectionism 🎯
↳ Done is ten times better than perfect.
↳ Set three major goals each week and pursue them with focus.

5) Constant distractions 🔔
↳ Social media and notifications destroy deep work.
↳ Use our 30-3-11 rule to work with your natural rhythm.

6) Overcommitting 📊
↳ Saying yes to everything destroys your impact.
↳ Follow Derek Sivers’ "Hell Yeah or No" rule.

- - - -

Productivity is not about doing everything.

It's doing the right things and dropping the rest.

Which of the six do you need to break most?

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Sometimes you don't need more advice.

You need a better lens.

7 visuals that will shift your perspective:

1) Self-care isn't selfish
↳ You can't pour from an empty cup.
↳ Protecting your energy isn't optional. It's essential.

2) Silence the inner critic
↳ Fear weighs more than failure ever will.
↳ Courage builds with practice, not permission.

3) Progress isn't linear
↳ Nobody operates at peak capacity every day.
↳ Consistency is about returning, not perfection.

4) Integrity outlasts charm
↳ A smile may open a door, but character keeps it open.
↳ Reputation is slow to build and quick to lose.

5) Clarity comes from action
↳ The path reveals itself only when you start walking.
↳ Start messy. Refine as you go.

6) Authenticity beats performance
↳ The world doesn't need another mask.
↳ People remember real voices, not polished ones.

7) Resentment is a chain you forge yourself
↳ Blame ties you to yesterday.
↳ Forgive, learn, and walk forward lighter.

- - - -

That first one is my favorite.

Which one resonates most with you?

Visuals by visual_minimalist (give him a follow on IG).

♻️ Repost this to help your network, too.
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