Scot Chisholm
@scotchisholm
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CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • deleted Twitter a while back, now coming out of retirement
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Joined April 2024
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I learned 7 critical lessons building a 100+ person B2B sales team…
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This happened to me too once…
How to deal with a manager that's stealing your ideas:
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18 insanely simple habits to become a great leader:
You don't need to be Steve Jobs to be a leader.
But after managing hundreds of people over 20 years...
It's these 18 habits that take you from good to great:
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The
#1
predictor of startup success…
Is not:
⌦ market
⌦ product
⌦ funding
It’s the *resilience* of the founders.
The ability to overcome challenges…
And come out stronger on the other side.
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Most managers have trust issues 👇
🤬 Spoon feed tasks
🤬 Needs constant updates
🤬 Needs to be in every meeting
🤬 Monitors when you come & go
Here’s 6 ways to keep trust high…
And never become that boss:
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68
Stop focusing on culture.
It’s like trying to push a rope.
Focus on these 10 “ingredients” instead:
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If you want to be an elite CEO, read these 7 books (for <$200):
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The
#1
predictor of startup success…
Is not:
⌦ market
⌦ product
⌦ funding
It’s the *resilience* of the founders.
The ability to overcome challenges…
And come out stronger on the other side.
2
11
60
Most leaders make things way too complex.
And complexity kills companies over time.
Instead you should develop a minimalist mindset.
To lead 10x more effectively…
Simplify these 3 areas of your business today:
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60
How to hold yourself accountable…
So others don’t have to:
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9
60
7 farming concepts that changed my perspective on business…
I know, it’s not something you hear every day.
But farming (and talking to farmers) has taught me a ton in 2023.
Ready? Here we go👇
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I've tried hundreds of software tools as a founder... Here are 12 I can't live without.
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Most teams secretly don't trust each other.
Mine didn't either until I started doing this:
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I've been told to give up 100+ times in my life...
Even by friends and family.
As a founder, you'll go through some dark times.
Times that'll make you question whether you're doing the right thing. Whether it's even worth it.
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Competition is for losers.
And 6 contrarian views on business you won’t forget.
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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)...
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The
#1
threat to your company is you.
Yes, you read that correctly.
Spotting and recognizing these blindspots is often the difference between success & failure…
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Most company dashboards are useless.
Add 3 critical metrics and fix yours:
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Imagine hiring a team that:
✓ Shares your values
✓ Doesn't give up easily
✓ Needs little instruction
✓ Never stops learning
✓ Adapts well to change
✓ Lifts everyone around them
This is entirely possible.
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7 most powerful quotes from Yvon Chouinard
(that will change the way you think)
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How to make money while you sleep...
Build a team that kicks ass without you:
👇
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There are 50+ million new startups created every year.
9 out of 10 of them will fail.
Mostly because they don’t know what to focus on at each stage of growth.
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7 truths I wish someone had told me before starting my first company:
🤔
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I've never been more nervous in my life.
Waiting to go up on the TEDx stage and give a talk to over a thousand people.
My nerves must have been obvious...
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Meetings suck.
Here are the only 3 meetings you’ll ever need:
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12 Insanely simple habits to become a high-performing manager:
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Most founders never become true CEOs.
They get stuck in build-mode.
And never transition to scale-mode.
The question on the slide may seem trivial...
But the answer says a lot about how you lead.
So which one are you?
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Airbnb. Google. Skype. Dropbox. Fanduel...
What do they all have in common?
Rejection ❌
They were all rejected by VCs when raising money - multiple times.
Truth is, we've all been rejected at some point.
For me, it was painstaking to raise even $1M from investors...
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These 10 questions will make you think twice.
Used by the best leaders…
To immediately up your game.
Answer honestly!
(before you read the bullets)
Here we go: 👇
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We’re our own worst enemies.
After leading hundreds of people over the last 20 years...
Here's 7 "rules" that hold most leaders back:
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Sorry, but your team is dysfunctional.
Well, at least 90% of you out there.
Do you recognize these 5 symptoms?
If so, here’s 5 ways to fix things:
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How to ask for a raise and finally get one…
(harsh truths from your boss's perspective)
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I'm a terrible manager.
That's what I thought when I first started leading others.
I went from managing 2 people to 100s in the space of a few years.
There was no playbook on how to become a better manager (at least I didn't see one!).
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Copy this if you're a manager.
After 20 years of leading teams...
I noticed the best managers obsessed about 3 things.
And their teams ran laps around the competition:
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A first-time founder reached out for advice…
Feeling lost and stuck…
Here’s what I said:
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I kinda hate social media…
At least that’s how I felt for the last 10 years.
So in March 2023, I was really nervous jumping back in:
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They tell you its product or market that kills startups…
But after investing in 20+ startups and coaching dozens more….
I can tell you its these 7 things that plague the ones that fail.
Here’s 7 non-obvious startup killers: ☠️
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Are mission statements still relevant?
Without a doubt, yes.
Your mission is your reason for existing.
Your purpose.
So, it's essential to get this right.
But most mission statements are a jumbled mess of corporate jargon.
Not inspiring or helpful in any way.
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How to scale the soul of a company:
Question:
Can a business scale while still maintaining the “soul” of the company?
Should you even try to hold on to that “feel” of a small team?
Would love your thoughts 💭
- JT
👇👇👇
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Most workplace conflicts can be prevented.
After leading 300+ people over the last 15 years, I’ve seen lots of conflict - both healthy and unhealthy.
Healthy conflict is highly beneficial.
But the unhealthy stuff can go.
Almost all unhealthy conflict stems from
common causes…
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I lost an A-player once...
And I didn't even see it coming.
Never let that happen to you.
Here are 7 signs your top performer could be on the move:
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You need an Ivy League degree or know people in Silicon Valley to make it as a founder.
That's what I thought when I became CEO of Classy at 24.
Fact is, we started Classy with none of that.
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7 business things you won't give a f*ck about in 5 years...
It's good to care...
Just don't get derailed (like I used to).
These are a natural part of the journey.
Rebound quicker when they inevitably happen...
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In my last 15 years in business, I’ve built teams of 300+.
And studied what the best have in common:
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Everything changed for me when I realized...
This investor advice was bull sh*t:
"Pick a bigger market,
Your TAM is too small."
Even Guy Kawasaki once told me...
Your market isn't "investor-worthy".
But 15 years later, I'm calling his B.S.
Here’s the advice I’d give instead:
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Most investors lie to you.
Cutting through this bull sh*t will save you countless hours & a ton of $$.
And set you up for a successful raise.
Here's 10 common investor lies to look out for 👇
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Disruption doesn't come from:
⌦ big ideas on paper
⌦ a charismatic leader
⌦ a massive funding round
It comes from a process that anyone can do.
I call it the "𝗣𝗹𝘂𝘀 𝗢𝗻𝗲".
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Want to make 7-figures in your first year as a founder? Then don't read this post.
That's not quite how founder compensation works.
But eating ramen noodles as a founder isn't a badge of honor, either.
I sacrificed compensation for too long.
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I stopped performing annual reviews.
99% of the time they don’t increase actual performance.
Give me 2 minutes.
I'll show you what I did instead:
👇
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A 21-year old college grad recently messaged me for career advice.
Here’s the 10 insights I shared 👇
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3 - Face challenges head on
Don’t hide from conflict.
Be quick to flag issues, but most importantly…
Come armed with possible fixes.
It’s not just about dodging disasters…
It’s about staying proactive and becoming reliable to others
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2 - Recognize blindspots
Have the self-awareness to recognize your weak spots…
And the determination to improve.
Seek mentorship and training to grow over time.
Treat feedback like a gift.
Your willingness to learn is the key to your personal growth.
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1 - Take Full Ownership
Don’t just fill your role, own it.
Imagine yourself as the CEO of your own domain…
Push for excellence in every action, task, project you take on.
But also take ownership of every misstep or failure.
You own your domain, in good times & in bad.
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"You ask me about the past, you ask me about the future, the only way to be happy is to be living right now."
We're so fixated on the past or the future. But true peace is found in the here and now.
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"The word 'adventure' has gotten overused. For me, when everything goes wrong - that's when adventure starts."
Most of our learning comes from moments of struggle & adversity.
Thinking of this as an "adventure" is an awesome positive frame.
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3 - The Mirro Technique
When hit with a personal attack, imagine a mirror in front of you.
Reflecting their own insecurities or issues back at them.
You’ll sleep better at night knowing this type of negativity is more about them, than you.
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This creates a healthy layer of detachment…
Allowing you to process feedback without emotional weight.
It’s not personal — it’s part of the play.
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5 - Ask for help
Accountability isn’t about doing everything yourself…
It’s knowing when to ask for help too.
Don’t waste your 1x1 time with your manager (all too common)
Use every moment as an opportunity to ask for feedback or help as needed.
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5 - Don’t copy
Overcome the compulsion to imitate. Instead?
Create something new and unique that is valuable to society.
Be so good that others start to copy you.
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"Fear of the unknown is the greatest fear of all."
The one of the most important to conquer. The unknown holds endless possibilities just waiting to be explored.
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1 - Emotional Alchemy
Embrace the mindset of an ancient alchemist.
Turn negative feedback into constructive insights.
Dig for the positive nugget or lesson for growth.
This turns emotional lead into gold.
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2 - Confident Pose Paradox
Your body language speaks before you do.
- Stay relaxed
- Maintain eye contact
- Stand up straight
- Don’t fidget
Or adopt a power pose, like wonder woman.
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1️⃣ Polyculture Productivity
Create resilience by planting multiple crops.
Lessons?
- Don’t over-rely on just one product or service
- Create revenue streams that protect each other
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1️⃣ Where did you grow up?
Help them expand:
- What was it like?
- Did you move as a kid?
- How long were you there?
Nothing helps you empathize with people more than understanding their upbringing.
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1. Set high standards
• Always believe in better
• Inspire the same in others
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3️⃣ If you fast-forwarded 100 years, would your mission still be relevant?
- Understand ‘why you exist’ at a deep level
- Ensure your mission articulates this
- And is directionally important forever
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4 - Admit mistakes
Mistakes are part of the game.
Be open about them,
Learn from them,
Get stronger because of them.
Owning up to errors displays your integrity and commitment to improvement.
Your honesty opens the door to future growth.
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5️⃣ Succession Planting
Method to extend harvests by staggering crop planting.
Lessons?
- Build up leaders at all levels
- Nurture future leaders for great outcomes
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7. The Silent Film Star Who Beat Bankruptcy
Buster Keaton was a silent film star in the 1920s. But with quick rise of sound films, he became bankrupt.
Yet, he persevered and is now ranked as one of the greatest actor-directors of Hollywood.
A true lesson of adapting to thrive.
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2 - Resource drain
American culture:
- admires competitors
- extols competition
But competition doesn’t serve businesses; instead, it drains their resources.
Stop competing.
Start creating.
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6 - Negative sum-game
Competition is a negative-sum game.
The total value of the market is reduced by the amount of resources that are spent on competing.
It’s a futile race to the bottom.
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4️⃣ Hybrid Vigor
Crossbreeding produces offspring with improved traits.
Lessons?
- Collaborate to breed ideas and solutions
- Engage with diverse perspectives
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1️⃣ If your company was hiring for your role, would they hire you?
- Your role must be earned at every new phase
- Embrace the ethos: ‘Always be learning’
- Push yourself to learn faster than company’s growing
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I'm about to do something I've never done before...
I'm hoping you'll join me!
On June 4th and 5th I'm hosting a COMPLETELY FREE masterclass..
Called "5 Things to Reach $100M in Revenue"
It's designed for startup leaders, but anyone is welcome to join!
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1 - Linguistic Minimalism
Speaking less can say more.
Use ‘verbal white space’:
Strategic pauses in your speech.
This adds weight and authority to your words.
Speak deliberately and pause confidently to get your message across.
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2 - Temporal Distancing
Fast forward ten years from now.
Will you care about negative feedback then?
Of course not!
This perspective minimizes the sting of comments.
Making thtem feel way less significant.
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Leaders are people too.
It’s easy to take things personally.
but the best leaders have mastered the art of objectivity.
They don’t let criticism derail them…
It’s a data point used for growth.
Here’s how to do it:
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Teams have all kinds of trust issues.
- Egos get in the way
- Issues fester under the surface
- Teams become dysfunctional
Mine was the same - until I found this simple trust-building exercise:
(which I've now repeated dozens of times)
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4 - Don’t succumb to groupthink
A psychological attraction leads people to want to engage in competition.
Just because others are doing it, doesn’t mean you should too.
Focus on:
- your business
- think clearly
- and win
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6 - The Game of Probability
When comments sting, stop and think:
Is it really about me? Play the odds here.
We usually have no idea what’s going on in that person’s world.
Chances are, it’s external factors like stress, personal issues, or past experiences.
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6️⃣ 7 Habits of Highly Effective People, by Stephen Covey
Key Lessons:
► Create win-win situations.
► Begin with the end in mind.
► Listen first, then conclude.
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4️⃣ Team Of Doers, Not Leaders
When leaders make all the decisions,
They become a massive bottleneck.
Instead grow leaders by:
• Letting them make decisions
• Setting their own goals
• Bringing forward opportunity
👉 Optimize for individual autonomy
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Train your brain to unwind these "rules".
Take note & catch yourself in the future.
And become the leader I know you can be.
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"The hardest thing in the world is to simplify your life. It's so easy to make it complex."
Simplifying things is actually really hard to do.
True strength lies in conscious subtraction.
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5 - Cognitive Costume Theory
Picture your mind as a stage.
When you face criticism, imagine it’s dialogue for a character, not you.
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2️⃣ Would anyone care if your company went away?
- Solve real pain points (painkiller not vitamin)
- Treat your people really really well
- Support the community where you operate
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3 - Focus on only producing value
Freed from the distortions of competition, focus purely on customer value creation.
Invest in what users prize.
Not what competition requires.
Define the market through your value.
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4. "People are not your most important asset. The right people are.”
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7️⃣ Our competitors have it figured out
Don't copy what your competitors are doing.
They don't have it figured out either.
Stay true to YOUR core.
Focus on your strengths and don't chase shiny objects in an attempt to beat them.
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"The more you know, the less you need."
True knowledge isn't about accumulating things, but about understanding what truly matters.
Let go of what's Unnecessary and make space for freedom.
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6️⃣ Not Living Values
Leaders are the moral compass of a startup.
If they don't walk the walk, the team won’t either.
When leadership acts as hypocrites…
It’s like a cancer that slowly kills the org.
👉 It’s on you, lead by example.
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4 - Personal Anthropology
Next time you’re in a rough interaction…
Switch to ‘human behavior research’ mode.
This strips the personal angle out of the equation…
You’re just a researcher trying to understand objectively.
Listen. Learn. Grow.
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