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) • Founder of nonprofit, Save Farmland

I'm a multi-time founder & CEO, but an operator at heart. 

My background is industrial engineering, ops research and six sigma - which had a huge influence on the way I built my companies. 

Now 20 years later, with a company portfolio worth $1B+ in value, I've started teaching other founders, managers and leaders how to become world-class operators.

Ring the bell on the top of my profile for more. I post on leadership, operations & startups. I don't care about going viral. I care about delivering value. 

If you want to go deeper, check out: 

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, a coaching program 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 coaching program: joinhighland.com

If your team doesn’t see the big picture, you’re failing as a leader.

And that’s putting it lightly.

Too many leaders underestimate the power of getting their team to buy into their vision.

A team that’s not sold on your agenda will:
-Half a$$ their work every day
-Quit at the first sign of trouble

But once they buy in?
👉They’ll walk through fire for you
👉They become an absolute force of nature
👉That’s why it’s important to communicate.

However, even yelling at the top of your voice doesn’t guarantee your message will be received.

There’s a better way to see if you and your team are on the same page.

And it starts by asking these 3 questions 👇

Then check out this article I wrote all about it: https://lnkd.in/gkFKs6-7

Let me know what you think!

Scot Chisholm

"HR handles culture"

A founder once told me this when I was evaluating an investment. 

It was a major red flag. 

And I didn't invest because of it. 

Why? 

Because culture is not any one function's responsibility. 

It's the responsibility of the leader. 

Don't pass "culture" off. 

Study the ingredients of great cultures. 

Then add them to your team...

With your own unique flavor. 

Become the 'culture chef'.

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

Black background with white text from Scot Chisholm. Culture is not an "HR thing". culture is a direct result of how you lead your team. It's the health of your people. It's only an HR thing if  they're forced to clean up your mess.

The #1 reason why you can’t retain your top performers:

No, it’s not the paycheck…

It’s the endless daily check-ins.

It’s wanting to be cc’ed on every email.

It’s insisting every decision be run past you first.

In short… it’s you.

Micromanaging seems like a great idea in theory.

But in reality, it only makes your team believe you don’t have faith in them.

And nobody likes to stick around in a place where there’s zero confidence in their abilities.

Don’t be the leader who hovers over shoulders.

Nobody wants a second shadow.

__________________

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

7 tricks to win any negotiation:

You don't get what you deserve.

You get what you negotiate.

Learn these 7 techniques I learned from FBI agent Joe Navarro.

What did I miss?

What did you learn?

__________

📌 PS. Like this post? 

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

7 tricks from an FBI hostage chief:

Your degree may be working against you: 

I've seen it first hand... 

The more degrees you get, the larger your blind spots. 

When I hire an MBA, I usually start off by saying:

"Congrats on your degree from [stanford, hardvard, etc.].
Now it's time to unlearn everything they taught you." 

It's a light-hearted way of saying... 

You need to fix your blind spots. 

And if you do, you'll be a homerun success here. 

So, here are the top 8 academic blindspots I've seen over 20 years... 

And how to fix each one: 

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

8 reasons why highly-educated people fail in business 

Stop agreeing with everything:

It’s safe but dull.

Instead:
• Speak your truth
• Show what matters to you
• Stand up for it
  
Sure, you might face pushback or criticism.

But it's better to be misunderstood than to only reflect others' opinions.

When you stand for something, you make an impact.

You encourage others to think, question, and act.

The world needs more people who care, not more who agree. 

______________
📌 PS. Like this post? 

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

Work-life balance is not the company's responsibility,  it's your responsibility...  

Says the CEO of Chase Bank in this video I came across. 

He says they do everything they can to help employees, like: 

• medical 
• shrinks
• pilates
• massages

But ultimately the person has to take responsibility for the balance in their life. 

It's their issue, not the company's. 

Genuinely curious what you all think here. 

Agree or disagree? 

I'll add my thoughts in the comments...

Most meetings are a total waste of time.

Follow these 8 rules to change this:

_________
📌 PS. Like this post? 

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8 simple rules to follow for every meeting:

What most leaders think:

- culture isn't a serious thing
- culture can't be measured
- culture isn't worth reporting on

What's actually true:

Culture is a reflection of the health of your team.

Culture can be measured through eNPS or surveying. 

The health of your culture should be reported back to leadership & your Board of Directors. 

It doesn't need to be this fuzzy thing...
 
If you pull your head out of the sand. 

Measure to improve. 

📌 PS. Wanna learn about the 10 ingredients of High-Performance Culture? I write all about it here: https://lnkd.in/gHAdTH4b

No one likes performance reviews.

So I do this instead: 

Here's a link to the full article (for free):
https://lnkd.in/gHY8mbTh

You can also sign up to get future articles delivered straight to your inbox! 

I go deep on leadership, management & operations every other week.

I almost quit my own company.

Many times.

Given the enormous pressure, most days it made sense to just call it.

But my co-founders would talk me off the ledge.

Until I grew thick enough skin to do it myself.

But here's the reality,

Most founders do actually quit.

The difference between the ones who do, and the ones who don't is razor-thin.

It comes down to resilience.

And you can learn to grow it over time, as I did.

Here are 7 ways to become more resilient for startup founders (or anyone in challenging roles):

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

7 ways to master resilience:

Stop overcomplicating leadership:

Great leaders don’t care about their "style." 

They don’t wake up and think, "What style should I use today?"

This is for books and schools, not real life.

Do not spend ANY time categorizing yourself. 

Just be you.

1. Show up every day and do what you think is right.
2. Be self-aware enough to correct things as you go.

That's it.

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

The #1 soft skill any leader can have:

How to know which metrics to track.

Most founders copy their competition and track everything.

Which is a great way to burn out.

But metrics aren’t a one-size-fits-all solution.

What’s relevant to another company won’t be relevant to you.

That’s why it’s important to know how to pick your battles.

Here are 5 things you need to know before deciding if a metric is worth your time:

_________
📌 PS. Like this post? 

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The one thing 99% of people get wrong about metris

A bitter lesson I learned after my third funding round went to sh*t:

Investors will say whatever they need to get a piece of the action.

Over the last 20 years, I’ve raised $200M+.

And in that time, I’ve heard every possible lie from potential investors.

Here are 16 of the very worst:

16 lies investors tell you:

Most leaders don't realize this:

As a founder in the trenches for 20+ years, I’ve seen my fair share of A-players come and go.

Most assume star employees leave because of compensation. 

Sometimes yes.

But for the majority, no. 

Here are the real (and hidden) reasons why top performers quit: 

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

Leaders are made not born:

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

The best displayed a combination of these 5 traits...
(All of which can be learned!)

And by focusing on these areas, you can elevate your leadership skills to the top 1%:

__________
📌 PS. Like this post? 

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5 essential traits of a world-class leader

The ultimate team dynamic:

Not just management. Not just leadership.

Both.

Most focus on productivity.
They're stuck in the output game.
Chasing short-term results.

There's a better way.

Build a team that:

-Increases productivity
-Inspires with a compelling vision
-Balances efficiency and future goals
-It's not just about getting more done.
-It's about creating a vision worth fighting for.

The real measure of success?
A team that's efficient today and motivated for tomorrow.

And never forget this:

The best leaders do both.
Maximize output. Inspire vision.

Your goal is not just a productive team.

It's a team that believes in the future.

Learn how to give feedback like the top 1% of CEOs:

Leaders, you've gotta stop giving sh*tty feedback. 

It pisses people off and doesn't help them improve. 

But it doesn't have to be this way. 

Feedback helps us crush goals in life and work 
(even if it can sometimes be hard to hear)..

Give me 2 minutes and I'll teach you:

This is the type of feedback people actually want...

1️⃣ It must lead to positive action

This is the golden rule. 

Provide clear, actionable steps that they can work towards.

Your delivery matters. Leaders seek to build people up, not tear them down.

If your feedback can't be flipped into a win, everyone loses. 

2️⃣ It's a two-way communication

Constructive, critical feedback is a dialogue, not a monologue. 

And if you're doing all the talking, you're doing it wrong. 

In-person is best, video calls are solid, and phone calls are so-so.

Some methods you should avoid at all costs:
• Emails are bad
• Slack is worse 
• Texts are horrible (and cowardly)

3️⃣ Don't sit on it

The old-school annual review is outdated and dying.

Feedback gets stale. Or frustrations bottle up and then explode. 

Give feedback ASAP.

A regularly scheduled 1x1 feedback meeting is great, 
but you don't always need to wait for them.

4️⃣ Be clear and specific

Focus on actual examples:

1) "When [XYZ] happened..."
2) Explain the effects on the team
3) Pause to let them take it in

Don't say it 3 different ways and labor the point. 

If they need more details, they'll ask.

5️⃣ End on a positive note

Transition with, "Here's what I'd love to see..."

Then ask if they think the feedback is fair.

Invite feedback on yourself. 
"Is there something I could have done better as your manager here?"

It's a two-way street. Hold each other accountable constructively. 

Focus on growth and solutions and don't bottle it up until you boil over. 

Give people the time and resources to improve, and be receptive to receiving feedback. 

Don't hold others to a standard you're not personally willing to live by.

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

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