Highland

Highland is a private CEO coaching program & community for high potential startup founders. 

If you're a founder looking to build a thriving, valuable company, we should talk! Click the link below.

Founder • CEO Coach

Scot Chisholm & Co. 

Join 100,000+ people receiving actionable advice on leadership, startups and scaling companies.

Founder • Writer • Investor

Haskill Creek

Haskill Creek is a new type of self-care store. Imagine a healthier & more holistic version of a Walgreens or CVS - with our first two stores in and around Whitefish, Montana.

Founder & CEO

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)

Tall Timbers Holding Co.

Family-run investment fund with 20+ investments in startups and 7 exits.

Founder, Managing Partner

Save Farmland

Save Farmland is a nonprofit organization with a mission to protect and promote small farms in Flathead Valley, Montana, and beyond.

AERO Montana

Board Member

Abundant Montana (a program of Aero), makes it easy for anyone to find and choose local food in Montana.

Advisory Board

Cannabis Counter

Cannabis Counter is a line of ultra premium and organic cannabis products - namely award winning gummies.

Cofounder & Owner

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.

Board Director & Co-owner

CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • How to lead teams & build companies

👉 I help people lead teams & build companies. No fluff, no B.S. Just actual learnings from 20 years of founding companies myself. 

Much more 👇

Hey I’m Scot - CEO, founder, investor, writer. 

But an operator at heart. 

I love leading teams and building companies.

So after growing a personal portfolio worth $1B+ in value…

I’m now teaching others how to do the same thing. 

Follow me for daily tips on leadership, startups and operations. 

And be sure to check out my newsletter, where I go even deeper on each topic! 

scotchisholm.com

MY BACKGROUND ————— 

🎗 Founder of Classy, a SaaS platform for 10k+ nonprofit orgs raising billions per year. 

🚀 CEO for 10+ years. Grew company from $0 to $1B+ valuation; 300 person team; raised over $200M from investors.

🤝 Acquired by GoFundMe in 2022 to create the largest giving platform in the world. 

🏔️ Recently founded Highland, an accelerator for high-potential founders. 

🏡 Haskill Creek, a much healthier version of a Walgreens or CVS. 

🌿 Cannabis Counter, a female-forward premium cannabis brand. 

🧑🏼‍🌾 And Save Farmland, a nonprofit protecting local farmland. 

🌲 Angel invest out of a family fund called Tall Timbers w 20+ investments 

⚽️ 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 / press oppty? DM me here, or email me@scotchisholm.com

→ Leader / manager? Join my newsletter: scotchisholm.com

→ Founder? Check out my accelerator + community: joinhighland.com



20 brutally honest truths every leader needs to hear: 

👇

It’s been nearly 20 years since I started my first company 🤯

So I put together these leadership truths I've learned along the way. 

Let me know your favorite!

Here we go... 

👇

1. You gotta own your shit. You started it, you own it - for better or worse. It’s that simple. 

2. Busy isn't a badge of honor. Take control of your calendar. Go for effective, not full. 

3. Shut up and listen. Leadership isn't how good you look. Listen and learn. Use it to make better decisions.

4. A “visionary” isn’t a real role. You must put ideas into action. Don’t become the “idea guy”. 

5. Your communication likely sucks. You overestimate clarity. And underestimate frequency. 

6. Don’t be a hypocrite. You must lead by example. Live your values every day, or no one else will. 

7. Stop avoiding the hard talks. Man up - it’s the only way to grow. 99% of the time everyone feels better afterwards. 

8. Managing with too much control will backfire. No one wants to work for a dictator. 

9. Managing with too little control will also backfire. You need strong systems to keep alignment. 

10. Success starts at setback. Every challenge is a hidden growth opportunity. 

11. Popularity isn’t your goal, results are. Your job is to make the tough calls when others won’t.

12. You live in a bubble as the leader. Surround yourself with people who are willing to pop it.  

13. Your main job: learn faster than any one else. Integrate learnings even faster. 

14. The answer is usually in the mirror. Stop looking externally, focus internally instead. 

15. Sit still and you’re dead. Have a bias towards action. Any decision is better than no decision. 

16. Everyone will doubt you (including yourself). But the best still show up every day and prove them wrong. 

17. Scale comes from leverage. Leverage comes from high output vs input. Focus on high leverage things.

18. Profit is not inspiring, creating meaningful value is. Always lead with value. 

19. Most things will go wrong and you should expect this. Build an 'adapt  and overcome' culture. 

20. Find something to stand for. Agreeing with everything is boring. Show the world what you care about!

__

👍 If you agree
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Scot Chisholm

How can I build an 'adapt and overcome' culture in my organization?

What are some key strategies for effective leadership?

99% of leaders miss this point: 

If you don't provide your team with context...

They are essentially operating in the dark. 

Your job as the leader? 

Turn the light on for them.

Let them do their job at full strength. 

Your team will thank you!

__

👍 If you agree
♻️ Repost to your network
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What are some examples of providing context to a team?

How can a leader help their team work at full strength?

No one knows if your idea is great: 

- Not your parents
- Not your friends 
- Not your advisors 

If we had listened to the advice early on,
We never would have started Classy. 

Instead of asking for general advice, try this: 

• talk to potential customers
• and ignore everyone else
• focus on pain points
• refine your idea 
• launch ASAP

Also remember:
Your initial idea is rarely the idea that hits.

It's an iteration of the initial idea.

Get something out there. 
Get tons of feedback. 
Adjust accordingly. 

__

Enjoy this?

♻️ Repost to your network and follow Scot for more.

Want to level-up your leadership?

📌 Join our free newsletter & community of 100,000+
https://lnkd.in/gpy2Z2jR

📌 If you're a founder, you gotta check this out: 
https://joinhighland.com/

Culture is an output, not an input. 

Focus on these 10 "ingredients" and great culture will follow: 

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📌 You’ll love my free newsletter for CEOs and leaders:
https://lnkd.in/gpy2Z2jR

📌📌 Or my accelerator for founders looking to 10x their company:
https://lnkd.in/gsZxfBJS

10 Ingredients of a High-Performance Culture:

Don't overcomplicate motivation. 

The core things people need: 

- to find purpose in their work
- to make progress in their lives
- to get paid well 

When someone checks out, 
One of these is off for too long. 

The leaders's job is to ensure that never happens. 

Otherwise, it's just a matter of time. 

__

Enjoy this?

♻️ Repost to your network and follow Scot for more.

Want to level-up your leadership?

📌 Join our free newsletter & community of 100,000+
https://lnkd.in/gpUx72SR

📌 If you're a founder, you gotta check this out: 
https://joinhighland.com/

This is a crazy stat: 

75% of Americans say their boss is the most stressful part of their workday.

Not surprising though. 

When I first started managing people... 

I had no idea what I was doing. 

Poor communication. 
Too many "priorities". 
Lack of feedback
Etc. 

And bad habits spread fast! 

But growing my startup from 0 to 300+ people meant I had to figure it out - and fast. 

I'd later go on to manage hundreds of managers over the years... 

And noticed the best ones all did similar things. 

Here are 12 simple habits that I wish I knew when I first started managing people: 

_____

📌 You’ll love my free newsletter for CEOs and leaders:
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📌📌 Or my accelerator for founders looking to 10x their company: https://lnkd.in/gsZxfBJS

*stat from: American Psychological Association

If you can't sell, you won't be successful. 

Go from zero to hero in 10 steps...

_________

Want to level-up your leadership?

📌 Join our free newsletter & community of 100,000+ today: 
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Every leader needs to learn sales

Create a mission that doesn't suck:


Find this valuable? 

Repost to share with others ♻️.

And follow Scot for more like this.

📌 You’ll love my free newsletter for CEOs and leaders:
https://lnkd.in/gpy2Z2jR

📌📌 Or my accelerator for founders looking to 10x their company:
https://joinhighland.com/

How to write a great mission statement: 

I've hired dozens of executives... 

From places like Okta, Atlassian, Redfin, VRBO, just to name a few.  

But as a first-time founder & CEO... 

I had no idea what I was doing.

So I put together my top 7 mistakes hiring & managing executives. 

Hopefully it helps you first-timers out there!

📌 PS. Like this post? 

Try the only leadership newsletter you'll ever need: https://lnkd.in/gpy2Z2jR


What are some common mistakes when hiring executives?

How can first-time founders avoid common hiring mistakes?

Top 7 mistakes hiring dozens of execs

This is what a great leadership team looks like: 

Broken out by each phase of growth from $0 to $100M.

The inspo came from a Highland member who asked for me advice on his leadership team.

Below was part of my response. 

Startup leaders - how does this stack up with your own experience? 

What'd I miss? 


__

Want to level-up your leadership?

📌 Join our free newsletter & community of 100,000+
https://lnkd.in/gpUx72SR

📌 If you're a founder, you gotta check this out:
https://joinhighland.com/

How to reinvent your leadership team From $0 to $100M

When something's not working...

Instead of pointing fingers... 

Look in the mirror first. 

The good news?

You can learn to be a better leader. 

Focus on two things: 

1) Clarity

Provide clarity with these 3 questions:
 
• why are we here?
• where are we going?
• how are we doing? 

You should be able to answer them, 
and so should your team. 


2) Consistency 

Provide consistency by:

• creating a reliable routine
• not chasing shiny objects 
• keeping your team informed of progress

Nail these two things and you'll be well on your way! 💪🏼


______
PS. You’ll love my free newsletter for CEOs and leaders:
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Or my accelerator for founders looking to 10x their company:
https://joinhighland.com/

Stop saying:  "I need them to take more ownership"

If you're not willing to give them actual ownership opportunities. 

No one can take ownership if all you do is bark orders. 

👍 If you agree
♻️ Repost to your network
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What are some examples of ownership opportunities for employees?

How can managers encourage employees to take ownership?

What's cooler than a $1 billion dollar valuation? 

A company that lasts 100+ years.

Here's how to build one: 


__

📌 Quite possibly the best leadership newsletter out there: 
https://lnkd.in/gpy2Z2jR

What are the key strategies to building a long-lasting company?

How can the best leadership newsletter help me?

Unicorns were never real. Aim for this instead

How to call your shot and actually hit it:

Goal setting is boring... 

Until you realize it makes or breaks your company. 

Follow these 7 rules & you'll be golden: 

___

📌 PS. Like this post? 

Here's the only leadership newsletter you'll ever need: https://lnkd.in/gpy2Z2jR

How important is goal setting for a company's success?

What are some best practices for goal setting?

7 Essential Rules of Business Goal Setting (1)

Leadership is not charisma:

It's not about extroverted personalities and lofty titles. 

After leading 300+ and studying hundreds of managers... 

The best displayed a combination of these 5 traits: 

__

Enjoy this?

♻️ Repost to your network and follow Scot for more.

Want to level-up your leadership?

📌 Join our free community of 100,000+ https://lnkd.in/gpy2Z2jR

📌 And if you're a founder, you gotta check this out: https://joinhighland.com/


Is hustle bad? 

Would love to hear your thoughts 👇

_____

📌 PS. You’ll love my free newsletter for CEOs and leaders:
https://lnkd.in/gpy2Z2jR

📌📌 Or my accelerator for founders looking to 10x their company:
https://lnkd.in/gsZxfBJS

Are you a strong leader?

Are you working for a strong leader? 

Find out in 2 minutes or less: 

________
📌 PS: You’ll love my free newsletter for CEOs and leaders:
https://lnkd.in/gpy2Z2jR

📌📌 Or my accelerator for founders looking to 10x their company:
https://joinhighland.com/

Test Your Leadership With 3 Simple Questions (1)

It took me 5 years to realize this:

Growth slows with no structure. 

Growth slows with fixed structure. 

Growth accelerates with adaptable structure. 

__

📌 PS. Tired of useless newsletters? 
Here's one you'll actually read: https://lnkd.in/gpy2Z2jR

What are some examples of adaptable structure for growth?

How can the promoted newsletter benefit me?

Don't become the bottleneck in your own business. 

I see so many founders reach product-market-fit... 

And then hit a ceiling. 

They're not able to scale themselves as a leader. 

And go from founder to proper CEO. 

We're now teaching dozens of founders exactly that in Highland...

The accelerator + community I launched in January. 

If you're interested in learning more, hit us up at the link below! 

We'd love to meet you: 

📌 https://lnkd.in/gsZxfBJS

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