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. 

🔥

The Higher Self Newsletter

Join 20,000+ followers of Higher Self, who are learning to access their Higher Self to drive change in life and at work.

Writer

Zella Life

Extensive research shows that nearly 90% of leadership success is driven by emotional intelligence (EQ) and strong soft skills. At Zella Life, our AI-enhanced coaching harnesses the power of emotional intelligence and cognitive behavioral science to help you and your team excel in every area of life.

For companies, our AI also mines pervasive themes across the board to identify the true wants and needs of your teams. This provides you with unique insights and enables smarter, more informed decision-making. Together, we can create a future where collaboration drives innovation and unites us.

Mucker Capital

Mucker Capital invests in Seed, Series A, and "pre-seed" stage companies building defensible and scalable, Internet software and services businesses outside Silicon Valley.

I support portfolio founders accelerate growth & build scalable products.

Growth Advisor & EIR

Techstars

Techstars is the world's most active pre-seed investor, with a portfolio of 9k+ founders.

I support founders with lead generation, content creation, and product management.

Mentor

The Way Out

The Way Out (TWO) is a fair-chance employment platform helping veterans & justice-involved job seekers re-enter society successfully.

After approaching us with their MVP platform, the Disruptive Labs team and I transformed TWO into a complete portal for JIJS (and veterans too!) to find jobs and receive support services from support-service providers. Through a well-tested, robust architecture, the TWO platform enables employers to post jobs and review applicants; support-service providers to onboard, communicate with, and support their enrollees; and job seekers to craft resumes, find and apply for applicable jobs, and work with support providers that match their needs.

Key technologies: React, Node.js, PostgreSQL, Redis, AWS, Docker, integration testing, E2E testing, CI/CD.

Investor

Nuooly, Inc.

Nuooly is an exclusive community enabling business-focused Independent Professionals (lawyers, accountants, etc.) to thrive and grow by providing new business opportunities, peer collaboration/support, and relevant learning content.

After investing in Nuooly and taking over its tech, we redesigned & rearchitected the platform, taking it from a problematic WordPress site to a fully-featured, secure platform for independent professionals to sign up, craft their profiles, and find and connect with each other.

Key technologies: AWS, TypeScript, Node.js, React, Next.js, Docker.

Disruptive Labs

Disruptive Labs is a Venture Studio focused on building and scaling technology companies.

Too many founders and innovators find their ideas fall apart due to sub-par digital products. So we created a system that offers them world-class design, development and content with no surprises and total flexibility.

Co-Founder & Managing Partner

HeyHome

HeyHome is your one-stop solution for all home-related needs. From ongoing maintenance to one-off improvements, from minor repairs to major renovations, we cover it all. We act as both a service provider and a knowledge resource, making sure you have the support and the information you need to make your home the best it can be.

From zero to MVP, the team and I put together a scalable platform to handle orders for a huge variety of local home services in a matter of weeks.

Key technologies: Stripe, React, Next.js, AWS, Docker, Twilio, Node.js.

Tilly 

Tilly empowers homeowners to unlock the full potential of their outdoor spaces. From quick curb appeal updates to transformative backyard renovations, our team of designers, horticulturalists, product specialists and construction coaches are by your side every step of the way. Think of Tilly as your trusted resource for all things outdoor living.

The Disruptive Labs team and I took Tilly's original MVP to the next level, migrating from WordPress with various fragile external integrations/plugins to a custom web app that handles the entire flow from purchase to a final yard design. Customers and designers can collaborate on each project and stay up to date on progress.

Key technologies: AWS, Docker, Next.js, React, PostgreSQL, Redis, TypeScript, Node.js, integration & end-to-end (E2E) testing.

Me Tyme

Me Tyme offered a behavioral health solution for SMBs providing access to short videos and interactive lessons to stop emotional stressors as they happened in real time.

In my role as Head of Product, I lead redesign efforts and supported our Disruptive Labs engineering team in the rebuild of Me Tyme's frontend platform, replacing an early-stage demo with a fully-fledged dynamic portal customized to each user's preferences.

Key technologies: Next.js, React, AWS.

Helping Leaders Ignite Change Through Inner Growth 🌱

There are truly two ways to live in 2025:

1. Striving endlessly for more. Feeling separate & disconnected.
2. Living fully in the present. Aware of our shared connection.

Most live stuck in the first.

Inevitably leading to stress, burnout, and a sense that something’s missing.

The bigger problem?

This way of living doesn’t just drain your energy, it costs you the deeper joys of life:

- A clear & peaceful mind.
- Meaningful relationships.
- A deep sense of fulfillment.

The truth?

You don’t have to sacrifice well-being for success.

Life doesn’t need to feel like a constant grind.

Your way forward:

Live (and lead) with presence, connection, and intention.

My goal is to help leaders and organizations:

- Embrace the present moment to lead with clarity & connection.
- Build emotional intelligence for stronger relationships.
- Shift focus from individual goals to shared progress.

The future belongs to those who lead with the heart, inspiring collective growth over individual ambition.

--

I am a husband, father and co-creator.

For 15+ years, I have been building tech companies and supporting leaders to:

- Improve lives
- Extend quality time
- Foster positive change

My deepest purpose in life is to touch and improve as many lives as possible.

To achieve this, I share everything I know and continue to learn over time.

It's up to you to decide how to use this knowledge to help others.

If you ever want to work with me, my door is open.

If not, take what you learn and pay it forward. 

We are all in this together!

Marco Franzoni

The real measure of your career isn’t your skill set.

It cuts much deeper 👇🏼

You’ve spent years honing your craft.
You’ve built trust, earned titles, carried weight.

But the thing that truly shapes your path isn’t expertise, it’s character.

7 moments that expose who you really are:

1. How you respond when a junior’s idea outshines yours
↳ “That’s brilliant. Let’s build on your suggestion.”

2. How you act when no one thanks you for extra effort
↳ “I’m glad the work landed well. The team made it happen.”

3. How you treat the intern when your calendar is packed
↳ “I’ve got 5 minutes now — what’s on your mind?”

4. Your tone when a colleague delivers bad news
↳ “Thanks for letting me know early. Let’s problem-solve together.”

5. The words you choose when giving tough feedback
↳ “Here’s what’s strong. Here’s one shift that could elevate it.”

6. Your patience when projects stall and momentum fades
↳ “Let’s revisit the ‘why’ and reset the next step.”

7. How you hold yourself when someone questions your integrity
↳ “I want to clarify, here’s what actually happened and why.”

Character may get you inside the room.
But it’s character that determines if you stay there.

And unlike skill, character is revealed in the smallest moments.

Every day is a chance to choose who you’ll be — what’s your choice today?


♻️ Please repost to remind others: character is the real career currency.
🙂 Follow Marco Franzoni for more.

Mindful Leadership Advocate | Helping leaders live & lead in the moment | Father, Husband, & 7x Founder | Follow for practical advice to thrive in work and life 🌱

Your title doesn’t make you a leader.  

Your consistency does.  

It’s tempting to chase recognition,  
believing visibility equals value.  

But that mindset leads to:  
- Burnout disguised as ambition  
- Teams that mirror your stress  
- Progress without fulfillment  

Real leadership happens in quiet moments.  

Start here👇🏼  

1) Stay human.  
↳ Admit mistakes early.  
↳ Laugh with your team, not at them.  

2) Keep promises small — and keep them.  
↳ Follow through on the simple things.  
↳ Your word builds trust faster than status ever will.  

3) Empower others to shine.  
↳ Share your platform.  
↳ Celebrate contributions in public, coach in private.  

4) Listen before leading.  
↳ Ask one more question than you answer.  
↳ People don’t follow the loudest voice — they follow the one that hears them.  

5) Show grace under pressure.  
↳ Stay grounded when things fall apart.  
↳ Your calm sets the emotional temperature for the room.  

Your position might open doors for a while.  
Your presence keeps them open for good. ✨  

Which one will you practice today?  


♻️ Please repost to promote presence-based leadership.  
🙂 Follow Marco Franzoni for more.

PEOPLE WONT
REMEMBER
YOUR TITLE.
THEY'LL
REMEMBER
HOW YOU MADE
THEM FEEL.

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