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. 

🔥

Greg Moran

Evergreen Mountain Equity Partners

Evergreen Mountain Equity Partners is an early stage (seed and series A) venture firm focused exclusively on future of work and HR related technologies. Our mission is to be an active partner to great founders trying to find a way to achieve their vision.

Serve as board member or board observer to Truvelop, Ceipal, Conquer, Chatterworks, Hitch and Spacebands.

Managing Partner & Founder Coach

Conquer

At Conquer we are making selling smarter through our enterprise sales enablement platform. Our comprehensive solution combines automation, advanced analytics and AI-driven insights to empower sales teams and drive revenue growth. 

By leveraging our platform, sales professionals can optimize their strategies, enhance customer engagement, and close deals more efficiently.

Chief Executive Officer (Interim)

Conquer provides sales enablement software to large sales teams.

Interim Chief Revenue Officer

Outsorcy

Outsorcy connects businesses with top-tier global talent to drive efficiency and growth. Specializing in outsourcing solutions, we help companies build dedicated teams, find world-class professionals, and streamline operations across marketing, technology, and business support. With a focus on flexibility, cost-effectiveness, and quality, Outsorcy empowers organizations to access diverse, skilled professionals worldwide, enabling them to scale efficiently and achieve their goals.

Camden Partners

Serve as an Operating Partner to Camden Partners. Since our founding in 1995, Camden Partners has focused on investing growth equity in lower middle market companies. We actively partner with strong management teams leveraging our domain expertise, operating experience and extended network of resources to help growth companies reach their full potential.

Operating Partner

Outmatch (now Harver)

Harver (formerly OutMatch) is a leading HR technology company that is transforming the way organizations hire and assess talent. 

Our innovative platform combines advanced data science, AI-powered assessments, and interactive pre-employment tools to help companies make smarter, data-driven hiring decisions. 

With Harver, companies can streamline their recruitment process, identify top candidates efficiently, and reduce bias in the hiring process. Our mission is to revolutionize talent acquisition by providing organizations with the tools they need to build high-performing teams and drive business success.

OutMatch makes people decisions more scalable, predictable, and personal with an end-to-end talent decision platform. The world’s most recognized brands rely on OutMatch to scale recruitment, understand their talent, and personalize candidate and employee experiences. Over 1,000 global companies trust OutMatch technology to process millions of candidates annually, and to achieve 25X return on investment through better people outcomes.

OutMatch is a portfolio company of Rubicon Technology Partners (headquartered in Boulder, Colorado) and Camden Partners (headquartered in Baltimore, Maryland).

President and CEO

Chequed.com

Oversight of all aspects of this emerging growth technology company. Provided vision and direction to the initial and ongoing product development. Raised outside equity based capital. Negotiated strategic partnership with major academic institution for R&amp;D. Initiated, negotiated and completed the acquisition of leading industry player to incorporate into Chequed. Ongoing responsibility for capital raising, recruitment of management and board level hires, acquisition integration as well as general management responsibilities.

Founder / President & CEO

Talent Management Group / W Business Books

Author of two books on recruitment strategy for the field hiring manager:

1.) Hire, Fire & The Walking Dead, W Business Books, May 2006 (http://www.amazon.com/Hire-Fire-Walking-Dead-Recruiting/dp/0832950017/ref=sr_1_1/105-7883773-0736465?ie=UTF8&s=books&qid=1181612256&sr=8-1)

2.) Building the TalentEdge: A Manager's Guide to Recruiting the Best, AuthorHouse, October 2005

Consultant, Author and Speaker

Talent Technology Corporation

Created a channel sales/partnership program and oversaw the initial phases of execution for this provider of human resource component technology. Responsibilities included partner identification, outreach, screening, contract negotiation and initial marketing of new partner relationships. Served as front line for acquisition identification culminating in successful completion of PeopleFilter Technologies in April 2008. In addition, oversaw the Industry Sales group focused on sales of the Resume Mirror product line to the top 500 staffing firms worldwide.

Director, Industry Sales and Partnerships

Better People, LLC

Better People provides technology-driven recruitment process outsourcing to emerging growth and established companies throughout North America.

Chairman

PeopleAnswers America, LLC

Acquired the rights to build the sales distribution channel for this web based behavioral assessment one-demand software company. Created and executed upon direct, partner and dealership strategy throughout North America resulting in multi-million dollar sales growth within 3 year period.  Provided direct enterprise sales (quota carrying) as well as sales executive support. Utilized full-time dealership and direct strategies as well as a traditional reseller relationship as primary methods of growth. Responsible for the creation of all channel start-up and ongoing training and development programs as well as internal communication and marketing initiatives. Created recruitment, evaluation and performance appraisal process used for management and development. Successfully sold distribution channel back to PeopleAnswers, Inc. of Dallas, Texas.

Vice President of Sales/Founder

Multi-Exit Founder & CEO, Advisor, Investor, Board Member | Posting daily insights to help you scale to $100m+. Host - The Founder’s Journey Podcast

Founders often face isolation, burnout, and the “now what?” stage after their first taste of success. I’ve been there—and I’m here to help you scale smarter and faster.

Over the past 20+ years, I’ve launched and exited multiple companies with valuations exceeding $100M, completed a dozen global acquisitions, raised nearly $500M in capital, and advised dozens of high-growth founders to do the same.

Now, I’m focused on “Scaling Together” through The Founder’s Collective—a curated membership community for ambitious entrepreneurs seeking strategic coaching, actionable resources, and meaningful peer connections. Through monthly coaching sessions, playbooks, live Q&As, and in-person events, members gain a powerful ecosystem to overcome isolation, lead effectively, and accelerate growth. If this resonates, apply today:
https://www.thefounderscollective.com/apply-to-join

I also take on a limited number of personalized coaching clients who want to supercharge their trajectory. If that’s you, DM me.

Beyond business, investing, and coaching, I’m a dedicated traveler, an avid home cook (inspired by Julia Child!), and a lover of the outdoors—especially fly fishing, hiking, and skiing in Colorado and Montana. Most importantly, I’m a proud husband and father of two amazing kids, each on their own unique journey.

At Conquer we are making selling smarter through our enterprise sales enablement platform. Our comprehensive solution combines automation, advanced analytics and AI-driven insights to empower sales teams and drive revenue growth. 

By leveraging our platform, sales professionals can optimize their strategies, enhance customer engagement, and close deals more efficiently. 

Today’s the day. And it all starts here.
Launch day for Scaling Across Borders: Season 1 – Kosovo.

This has been one of the most meaningful projects of my life.

When we started, I had no idea what to expect. I just hoped we could tell a different story about Kosovo… that it’s not a war-torn country, but a young, energetic nation full of talent, ambition, and grit.

It did more than that.
It touched a nerve. It showed a side of this place that the world rarely sees. The response here has been overwhelming.

Kosovo is an underdog story, and it’s been the honor of a lifetime to help tell it.
This country deserves to be seen, taken seriously, and invested in.

Somewhere along the way, I realized Scaling Across Borders wasn’t just a storytelling experiment for me or Outsorcy. It became a mission.
Because Kosovo isn’t the only misunderstood place.

There are founders everywhere, building world-class companies in overlooked corners of the world, whose stories never get told. They’re not chasing hype or creating videos to announce their latest raise. They’re building the future of their nations.

That mission continues beyond Kosovo.
It’s about authentic stories of grit and resilience, where travel meets entrepreneurship.

But it all starts here, tonight, in Pristina.

To the incredible team at Outsorcy  and my partners (Jim Trimarco Demian Costa Blendrit Elezaj Rilind Elezaj Ira Grossman  Siddharth Sehgal ), to Wanto Studios, my family (Allison, Olivia and Jackson) . and, of course, to the great people of Kosovo who trusted me to tell a small part of your big story ... thank you.

This experience changed me.
And it’s only the beginning.

🎥 Join us live from Pristina tonight at 6 PM CET / Noon EST / 9 AM PST on YouTube for the global premiere.

👉 Subscribe today to follow the journey. Link in comments.

Kosovo! Let’s go!!!!!

No alternative text description for this image

Scaling Across Borders - Kosovo episode now live! Link in comments.

This chapter is all about the people who left Kosovo, built their careers around the world… and chose to come back.

And the ones who arrived by accident ... and stayed on purpose.
Founders. Educators. Builders.

A generation turning Kosovo into a global hub for talent, tech, and opportunity. 🇽🇰

Featuring:
• Blendrit Elezaj — connecting Kosovo’s talent to the world
• Gent Dedushi — from Google + NYC to building at home
• Albina Balidemaj, PhD — shaping future leaders at RIT Kosovo
• Alejtin Berisha — bringing world-class education systems to Kosovo
• Zach Dowd, Ethan Allan & Dion Berisha — building Techatlon inside ICK

🎬 Episode 2: The Ones Who Came Home

📍 Now streaming! Link in comments.

Watch the full episode, drop a comment, and tell us what part of their story hit you the hardest.

New episodes every week. Don’t forget to subscribe.

Scaling  Across Border Episode 3 is Live! 

This one is about the people building Kosovo’s new economy from the ground up… not with factories or resources, but with pure intent and zero permission-seeking.

You’ll meet:

Gentrit Gojani and the KODE Labs 
Mergim Cahani 
Dorina Grezda and Shpend Lila at Innovation Centre Kosovo (ICK) 

Watch Scaling Across Borders — Episode 3!
Link in comments.

We're live in Kosovo! Join our livestream for the Scaling Across Borders premiere! 🇽🇰 

https://lnkd.in/enyiKVHf

Open video: Scaling Across Borders Premiere! on youtube.com

I’ve had days where it felt like nothing was moving.
No big wins. 
No breakthroughs.

But here’s the truth founders hate admitting:
The days that look quiet are often the ones that compound the most.

What kept me moving wasn’t some dramatic reinvention.
It was the small, almost boring actions done consistently.

So today, don’t go hunting for the perfect plan.
Pick one small move and execute it.

Momentum isn’t magic, but it’s built.

Subscribe to my newsletter for weekly insights: https://lnkd.in/e8wJrt5A

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