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Management, Ops / November 15, 2025

7 Essential Rules For Setting Business Goals

Crush Your 1 on 1 Meeting_ A Guide for Both Manager & Individual

Leadership, Management, Ops / February 13, 2025

How to Crush Your 1-on-1 Meetings

5 Rules to Master Delegation

Founders, Leadership, Management / November 8, 2024

5 Rules to Master Delegation

5 Essential Rules of Giving Feedback (The Right Way)

Management, Culture / August 30, 2024

5 Rules of Giving Feedback

How to Run the Perfect Leadership Meeting

Leadership, Management / August 16, 2024

How to Run the Perfect Leadership Meeting

The Annual Performance Review Is Dead – Do This Instead

Leadership, Management / June 28, 2024

The Annual Performance Review Is Dead

7 Reasons You’re

Leadership, Management / May 10, 2024

7 Reasons You’re Losing Your Top Performers

How to Resolve Conflict as a Manager

Leadership, Management / May 3, 2024

How to Resolve Conflict as a Manager

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Welcome, friend!

I’m Scot, multi-time founder, investor and industrial engineer by trade. I started a company called Classy, a SaaS platform used by over 10,000 nonprofits to raise money and manage their fundraising. In 2022 we were acquired by GoFundMe and together the companies have raised over $40 billion for individual and nonprofit causes. More recently I founded Highland Academy, a leadership program and community for founders transitioning into world-class CEOs.

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Who is Scot Chisholm?

Hey, thanks for asking. First, I’m a human, just like you (hopefully). Second, I’m a proud dad and husband. Third, I’m a multi-time founder, investor and (originally trained as) an industrial and mechanical engineer. I started a company called Classy at 25, with my friends and roommates in San Diego, CA. We grew it pretty big over the next 10+ years, and sold it to GoFundMe in 2022. Now I write a lot, teach founders in Highland, and help manage several businesses across our family’s portfolio. I recommend signing up for my free newsletter and if you want to work with me directly, check out Highland Academy. 

What companies has Scot Chisholm founded?

Classy is the company I’m best known for (at least in nonprofit and tech circles). Classy was acquired by GoFundMe in 2022, and they rebranded the company to GoFundMe Pro. I founded Highland in 2024, a leadership program and community for founders transitioning into world-class CEOs. I also co-founded Just Holdings (first brand launched is JustClaims) with Chris Himes in 2025, an AI-powered platform that helps property owners navigate insurance claims. Lastly I co-founded a few local businesses in Whitefish, Montana, including Haskill Creek — a reinvention of the traditional drug store — with my wife Carrie, high school friend Craig McViney and early employee Colette Stroia. 

What is Highland by Scot Chisholm? 

Highland is a leadership program and community for founders, CEOs and high-level operators that I founded in 2024. It has two parts:

  1. Highland Academy is a self-paced online “school” for founders, CEOs, and high-level executives scaling businesses from $1 to $100M+.
  2. Highland Society is an exclusive community of 150 or fewer founders & CEOs (and their leadership teams) that includes live training, events, and peer support. Society members span the US and beyond.

Why did Scot Chisholm start Highland? 

Back in 2017, I lived the nightmare most founders fear most: being pushed out of my own company by my lead investor. I got us far on brute force, but I wasn’t yet a great CEO. I was more builder than scaler. More brick layer than architect. The experience was painful, but it lit a fire under me to understand the role of CEO better than anyone they could possibly bring in to replace me. I studied the best, took what worked, threw out what didn’t. And I made a promise to myself that if we were lucky enough to survive the ordeal (we did!) and have a great exit (we did!), I would share everything I learned with others going through the same scaling challenges. 

What is the Northstar Operating System (NOS) by Scot Chisholm?

The Northstar Operating System (NOS) is a business operating system I developed while scaling Classy, and now teach to thousands of founders, CEOs and operators through Highland. I was frustrated by existing systems (EOS, OKRs, etc.) that were breaking down on our way to $100M+. I purposefully designed it to remove organizational complexity and create extreme alignment across my team. It’s built on three core pillars: Operating Clarity, Operating Rhythm and Operating Standards. You can learn more about it on my blog and at Highland Academy. 

What companies has Scot Chisholm invested in? 

I invest across software, AI and sports through our family fund, Tall Timbers Holding Co. Some of our investments include CaseText (acquired for $650M), Ripple, FanDuel (acquired for $11.2 billion), Hubble and Albion Soccer Club. 

What is Scot Chisholm’s affiliation with Albion Soccer Club? 

Albion Soccer Club holds a special place in my heart. My son first started playing for the club at 4 or 5 years old in San Diego. I became friends, and then business partners with long-time CEO Noah Gins. Our investment (through our family fund, Tall Timbers Holding Co.) helped kick start Albion’s national expansion around 2016. I continue to serve on the Board of Directors today and play an active role as a board member and close adviser.

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