CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Every week I tackle management, operations & startup topics that are helping 250,000+ people. Sign up free: www.scotchisholm.com

I also run a leadership accelerator that helps founders develop into top CEOs. Apply here: https://joinhighland.com/apply/

My backstory: 

🚀 Founder of Classy, SaaS for nonprofits raising billions per year

🎗️ Acquired by GoFundMe in ‘22 to create largest giving platform in the world

🌲 Investor in dozens of startups out of family fund, Tall Timbers Holding Co, (Ripple, FanDuel, Hubble, Casetext, etc.)

🏔️ Founder of Highland, leadership accelerator & community for founders

🏡 Co-founder of Haskill Creek, modernized & healthier version of a Walgreens or CVS 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland & food 

⚙️ Industrial engineer & lean six sigma nerd, UMass Amherst grad 

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation

It's been a wild ride. If you're interested in any of the above, please visit my website and reach out to me there. 

www.scotchisholm.com

Scot Chisholm

Getting pushed out of my own company taught me what a CEO actually does...

In 2017, I got called to my lead investor's office in La Jolla.

I waited 30 minutes in the conference room. Then the head of the firm walked in.

"The partners aren't happy with Classy's performance. We think it's time for some change." Two missed quarters. That's all it took.

I had built the company to tens of millions through brute force. But something had gone wrong. Growth slowed. I had become the limiting factor.

I hated them for it. But they weren't wrong.

I was more builder than scaler. More brick layer than architect. It took 24 months to buy them out and get us back on track. Some of the darkest times of my life, but also the deepest reflections.

That experience lit a fire under me to understand the CEO role better than anyone they could bring in to replace me. Not to become the next Jobs or Bezos. But to answer basic questions no one could give me:

What should I be doing all day? What should I focus on? What does a CEO actually do? So I obsessed over studying the best CEOs in the world. What separates the ones who scale from the ones who plateau?

I found that every great CEO masters 7 core responsibilities. I now call them the CEO-7.

I wrote a complete breakdown in yesterday's newsletter. 

If you wanna check it out, I'll drop it in the comments.

Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland, Just, Haskill Creek

How defining “great” changed our culture (and decision-making):

A new hire asked me a simple question after onboarding:

“What does great look like here?”

I didn’t have a clean answer.

Not because we lacked ambition, but because we’d never clearly defined it.

Mission, vision, and values weren’t enough.

What we were missing was our perspective on excellence.

That gap pushed us to document our company standards. The non-negotiables that guide decisions when things get messy, fast, or ambiguous. Inspired by how Patagonia articulated its philosophies, we created standards that outlived leadership changes and scaled with the company. 

Here's how I defined them 👇 

***
ps. If you want to read my in-depth article I wrote on this exact topic, I'll drop the link in the comments.

How to define what great looks like:

Here's how to create an unstoppable strategy in 3 simple steps:

First, what is a strategy? Most leaders get this wrong. Strategy is not vision. Strategy is not goals. It's the bridge between the two. Strategy is your unique approach to achieve vision. It shapes your annual goals and daily execution. Vision leads to strategy, which leads to goals.

To create an unstoppable strategy, you need three things:

- Unique approach
- Measurable impact
- Target market

I call this "strategic AIM." A stupidly simple, crystal clear description of strategy that anyone can understand.

1. Approach
What's our unique approach to accomplishing the company's 3 to 5 year vision? Why will people choose us? How are we 10x better than the competition? What are 3 to 5 core bets, multi year initiatives, that we will pursue? Your unique approach creates differentiation at all levels.

2. Impact
What does success look like when we achieve our 3 to 5 year vision? How do we measure it and track along the way? Customer impact, financial impact, shareholder impact. Get crystal clear on what success looks like from day 1.

3. Market
Most leaders target anyone that will buy from them. This is the wrong approach. Instead define exactly who your target market is. Think of it like an archery target. Primary is the inner ring, secondary is the 2nd ring, tertiary is the 3rd ring. Dominate the first before prioritizing the second.

Your strategic AIM informs how you set pricing, packaging, and messaging. It also makes annual goal setting a lot easier. What are the company's top three annual priorities that advance our strategic AIM? Pay special attention to your multi year core bets. These help shape annual goals.

Revisit your strategic AIM at least annually. As your vision evolves, your strategic AIM should evolve. They're joined at the hip. You should always have a company wide strategic AIM, but you could also have one for different products or markets as you get bigger.

If you're a founder or operator and you enjoy my content, you should check out Highland Academy: https://lnkd.in/eAVA5ekz

How to create an unstoppable strategy in 3 simple steps:

In 2017 I was called to my lead investor’s office in La Jolla. 

I had no idea what the meeting was about. 

They wanted me out as CEO after nearly ten years running the company. 

I had missed two quarters and lost their confidence. 

That was enough. 

But they weren’t wrong, I wasn’t yet a great CEO. 

While they tried to push me out, I studied the role like a maniac. 

Determined to be better than anyone that could replace me. 

Ultimately, it worked and the company 5x’d in valuation. 

Now I teach everything I learned through Highland Academy. 

If you’re a founder working to become a great CEO, this is for you.

I'll drop a link in the comments if you want to apply.

Or shoot me a dm.

Don't screw up your annual company kick-off!

Most CEOs don't realize how high-stakes their company kick-off really is. They waste the moment. Why? 

Because they don’t realize how high-stakes it is. They think B- work is ok. Check the box. Get back to the “real work”. I mean, you do have lots of shit going on. Carving out a half-day for a company kick off can feel like a waste of time.

I've been on both sides of this. As a founder, I learned the hard way that the leaders who put their heads down and "get back to work" in January are making one of the costliest mistakes of the year. The annual kick-off isn't a distraction from the real work. It IS the real work.

Andy Grove called this "managerial leverage" in High Output Management. The idea is simple: what you put in is nothing compared to what you get out. A few hours of intentional effort in January can shape the behavior of your entire company for months, if not years. Skip it and you put your team at an information disadvantage you'll be fighting all year long.

The truth is, your kick-off is the highest-leverage meeting of the entire year.
Get it right and your team has the clarity to do their best work all year long. Get it wrong, and you're playing catch-up on culture and alignment for months.

I've worked with hundreds of CEOs on this. The ones who treat their kick-off like the Super Bowl moment it is? They never say die. They show up prepared, energetic, and locked in, and their teams follow suit. The ones who phone it in? They spend the rest of the year wondering why nothing is sticking.

I wrote a guide to follow in a recent newsletter. It includes the one thing your team needs from their leader going into the new year: Purpose, Direction & Progress.

link in the comments to go in depth on this topic 👍

This is where companies quietly fall apart:

Most founders inherit the CEO title before they have any idea what it actually requires. 

You start the company, you get the title. 

No one sits you down and explains what the job is supposed to look like. 

You have to be intentional about learning the role. 

It’s not the same as being a founder. 

Two very different things.

***
Learn what the role of a CEO actually looks like in my recent article (link in comments)

How to speak like the top CEOs on the planet:

Most people communicate: 
- nervousness
- indecision
- selfishness

When they should be conveying: 
- conviction
- thoughtfulness
- partnership

Not all CEOs get it either, but the best certainly do. 

Here’s how 👇 

1/ Keep it clear & simple: Avoid jargon. Use plain English. Be yourself. Don’t over-share or talk in circles. Focus on nailing one main point but never exceed three. Don’t assume understanding. Ask the person if they get it.

2/ Speak with energy: Show enthusiasm & belief in what you say. Avoid fidgeting or whispering. Makes you look nervous. Stay solution-oriented. Don’t be a negative Nancy. You’ll demotivate everyone. Use storytelling to inspire & provide tangible examples.

3/ Talk like a partner: Say “we,” not “I”. Stay relatable to every level of the organization. Create a sense of shared ownership. Ask people: “What do you think?” Take people’s feedback seriously. Even if you make the final call.

4/ Communicate the ‘why’: Tie things back to mission & vision. Always explain reasoning behind major decisions. Help people understand company's progress. Create a sense of urgency when you fall behind. Say “because” more to force yourself to provide context to the team.

5/ Control your emotions: Never let feelings override the message. Stay composed under pressure. Don’t over-share and freak everyone out. But don’t sugarcoat things either. Be realistic & communicate a plan.

6/ Ask the right questions: Don’t pretend to have every answer. Find solutions through thoughtful questions. The best CEOs see themselves as detectives. Practice ‘5 whys’ asking why five times to find root causes.

7/ Guide, don’t dictate: Be a facilitator, not a dictator. Orchestrate debate & discussion. Pre-plan exercises that get people collaborating. Keep the room on track and constructive. Shape the discussion, don’t dominate it.


📌 ps if you want me to teach you how to do this at your company, check out Highland Academy: https://lnkd.in/eAVA5ekz

📌 📌 pps. if you enjoy my content, you'll love my free newsletter. Subscribe here: https://lnkd.in/e6ak5dbP

EOS and OKRs broke at scale. 

Here’s what replaced them.

I spent over a decade building Classy from a scrappy idea into a $100M+ company that processed billions in donations before we sold to GoFundMe.

As we scaled, one problem kept surfacing:
No operating system held up past ~$5M in revenue.

We tried OKRs. The product team loved them. But across the company they became too complex. Too many objectives, too many key results, quarterly resets, confusing grading. The system meant to create focus became a recurring distraction.

We looked at EOS. It was cleaner, but too prescriptive. And I didn’t agree with the idea that the founder should hand off operations to a “professional operator.” 

My belief is simple: The CEO must own the operating system.

There was also a deeper issue.

Classy was an impact company. Our mission wasn’t a slogan on a wall. It was the reason people showed up. We needed an operating system that connected purpose all the way down to daily execution, and not just tactical documentation.

So I built one.

It’s called the Northstar OS.

📌ps. If you want to dive into the Northstar OS framework, check out this article I wrote that breaks it down: https://lnkd.in/eDeRw6D2

pps. Sign up for my free newsletter here: https://lnkd.in/gXCsenmP

"Don't worry, you're gonna do great."

I was frozen in the green room at TEDx San Diego. My body felt like 1,000 pounds. I've only been a founder for a couple of years. Why am I giving a TED talk? People are going to laugh me out of this theatre.

An old man in the corner spoke up. That nudge got my legs working again.

I gave my talk. Came back dripping sweat.

"See, I told you you'd do great. You should be proud."

Then he walked on stage to give his own talk.

⁂

Years later, an advisor sent me a book that changed everything about how I manage people.

The One Minute Manager.

I googled the author. Ken Blanchard.

His face stared back at me.

The old man from my TED talk.

Here was one of the most successful business writers of all time, about to give one of his best talks ever, and he was focused on me.

That night I wrote Ken a thank you. He responded with equal grace.

⁂

The book became required reading for every manager at my company. Here are the 3 lessons that changed how I manage people forever:

1/ Great leadership is a side-by-side relationship. Not top-down. It's a partnership. When the organization wins, the people should win. Get this right and your people start managing themselves.

2/ Catch people doing something right. Positive recognition isn't soft, it's smart. People repeat what's recognized.

3/ Correct the behavior, not the person. Address mistakes quickly and specifically. End with reaffirmation. Every 1×1 becomes an opportunity to help people stay on track.

That night, Ken was demonstrating everything he'd later teach me through his book.

True leadership is the smallest acts of support, delivered at the right moment.

Full story + breakdown here:

Open article: 3 simple rules that changed how I manage people forever: by scotchisholm.com

3 simple rules that changed how I manage people forever:

Launch your own recruiting business & get new clients without quitting your 9-5 (see my 50+ LinkedIn recommendations below)

Are you an agency recruiter, corporate recruiter, or industry expert who wants to build your own recruiting business, but don’t know where to start or how to get new clients?

Maybe you’re:

- Unsure which niche to focus on
- Struggling to find clients 
- Trying to avoid conflicts with your current 9 to 5
- Worried about job security and looking to create an extra income stream

I get it, the idea of going out on your own can feel overwhelming and even experienced recruiters often struggle with business development

I’ll work with you to:
✅ Refine your niche, launch your recruiting business, and run it in “incognito mode” if you have a day job
✅ Land your new clients using our proven automated client acquisition systems
✅ Make your first $20,000+ placement (often in under 90 days)
✅ Follow the same system that’s helped 300+ people launch and grow profitable agencies

If you’re ready to take control of your income, flexibility, and future:

Click on the link below to watch my training video:

www.recruitinglaunch.com

𝐒𝐭𝐚𝐭𝐬 (𝐈𝐟 𝐲𝐨𝐮 𝐰𝐚𝐧𝐭 𝐭𝐡𝐞𝐦)
- 15+ years of experience in recruiting — built and sold my own recruiting agency
- Launched profitable recruiting business for clients across various industries, including tech, sales, healthcare, legal, finance, engineering, marketing, construction, and more
- 50+ client testimonials (check out my LinkedIn  recommendations at the bottom of my profile)

Jon Chintanaroad

Right before we decided to have a baby, Caitlin and I took this trip to Greece.

We hired a local guide to take us through Athens and then out to the Oracle of Delphi.

People used to go there for clarity before big life decisions.

Looking back, that felt fitting.

We were about to enter a whole new chapter.

That trip was one of the last quiet moments before everything changed.

I’m glad we had it.

And even more grateful we had already built something of our own.

A recruiting business gave us that freedom.

Not overnight. Not without effort. But in a way that’s real and sustainable.

The model is simple.

You help companies find great talent.
You get paid well for every successful placement.
And you can do it all remotely, on your own terms.

You don’t need a fancy resume.
You don’t need to quit your job on day one.
You just need a system, a willingness to learn, and a little consistency.

If that sounds like the kind of path you're looking for, start here: https://lnkd.in/eGTerf2N

It changed everything for us. It might do the same for you.

LinkedIn automation works.

But it's only half the picture.

Can I be straight with you?

Every hiring manager you're targeting gets 20+ LinkedIn messages a week from recruiters.

Your message is buried before they even see it.

But their email inbox?

That's where real work happens.


Here's what changed everything for one of our clients:

Running LinkedIn only.

Getting maybe 2-3 conversations per week.

Decent, but not enough to build a real business.

We added email to the mix.

Same targeting, same message, different channel.

Conversations jumped to 15-20 per week.

Why?

We stopped relying on one platform to do all the heavy lifting.

• LinkedIn = high intent, low volume
• Email = lower intent, high volume

When you run both together, you're not choosing between the two.

You're covering the entire market.

You show up where hiring managers actually work.

And you're not betting your entire pipeline on one platform.

That's the difference between scrambling when things go quiet

and having a steady flow of new conversations every week.

Are you running email alongside your LinkedIn automation?

CEOs delete 99% of recruiter messages.

Unless you do this instead.

Most outreach fails because it’s generic.
 No context. No signal. No reason to reply.

Here’s a better approach.

Step 1: Look at their hiring pattern.
 Find roles they’ve reposted multiple times. That’s where the real pain is.

Step 2: Start the conversation like this:

“Hey [First Name], I noticed you’ve been hiring for [role] since [month].
 I’ve helped a few [industry] teams unblock searches like this.
 Quick question, is the slowdown more of a skills gap or a process issue?”

That’s it.

No pitch.
 No credentials dump.
 No pressure.

Why this works:

It shows you’ve actually looked at their situation

It positions you as someone who understands hiring problems

It invites a real conversation instead of forcing a sale

It’s easy to respond to, most will say “both”

If you want to build relationships with decision-makers instead of getting ignored, this is where to start.

You can DM me if you want to see what’s been working lately.

What’s the most common mistake recruiters make?

Recruiting isn’t complicated.
But it’s easy to get wrong.

Most mistakes aren’t dramatic.
They’re small, repeatable, and costly over time.

From what I see, they usually fall into a few buckets:

Generic outreach that gets ignored.
Sending candidates who technically fit, but aren’t the right match.
Slow follow-up that loses momentum.


The recruiters who consistently perform well tend to get a few fundamentals right:

They’re intentional with outreach.
They understand both the client and the candidate.
They move quickly when timing matters.

Curious what you see most often.
What’s the mistake that shows up again and again?

My client Jeff made $50k in recruiting fees in 90 days.

And he replaced his engineering salary in 3 months.

His background:
 • Software engineer
 • Zero recruiting experience
 • Started while keeping his day job

Here are 5 simple rules that worked for him:

→ Only work critical hires
 Let other recruiters fight over every job posting. Focus on roles companies desperately need to fill.


→ Use hyper-personalized messages
 Mass spam = mass delete. Show hiring managers you understand their world.
 (Jeff’s first client reached out within 3 hours)

→ Let automation do the heavy lifting
 Don’t spend hours on manual outreach. Let systems work while you sleep. Respond only to warm leads.

→ Lead with candidates, not credentials
 Hiring managers don’t care about your years of experience or your company name. They care if you can solve their problem.

→ Only take roles you understand
 Jeff stuck to engineering roles he knew well. This led to better candidates and faster placements.

You can do this without quitting your job.

Start small.
Test the waters.
Scale when ready.

That’s how Jeff replaced his engineering salary in 3 months.

If you want more details on how this works, you’ll find them in my profile.

Years as a corporate recruiter.

Filled hundreds of roles.

Built relationships.

Knew the work.

But Emily had no idea how to get her own clients.

She could recruit.

She just couldn't sell.

That's the gap nobody talks about.

Corporate recruiters are great at filling roles.

But they've never been taught business development.

They've never had to close a client.

They've never run the sales side.

Because someone else always did it for them.

Emily joined Recruiting Launch in March 2025.

Here's what we built together:

• Niche locked: tech and insurance recruiting 

• Positioning dialed in: strategic talent partner 

• Systems running: client acquisition, outreach, sales process

Within months, she landed her first clients.

Started making placements.

Not for someone else.

For herself.

Same recruiting skills she always had.

Different business model.

That's the shift.

Going from filling someone else's pipeline to building your own.

Going from salary to owning the fee.

Going from corporate recruiter to business owner.

The recruiting part?

You already know that.

The business side?

That's what you learn.

What's holding you back from starting your own recruiting business?

Got laid off from Google.

Best thing that ever happened to me.

Didn't see it that way at first.

When the recruiter called, I thought I'd made it.

The campus. The perks. The badge that made every candidate pick up the phone.

Looked like the dream.

Until I saw what it actually was:

15-minute lunch breaks
Hourly contractors living in fear
First cut when budgets tighten

Recruiting on easy mode.

But building nothing that belonged to me.

Then the layoff came.

Sitting there with no job and no plan, had to ask one question:

What would I regret not doing?

The answer hit hard.

Not trying to build my own business.

So I gave myself 90 days.

Just to see.

That decision changed everything.

Because here's what became clear:

Job security is a myth.

Companies don't love you back.

Your role could disappear tomorrow.

The only real protection? The ability to generate your own income.

That separates people who survive layoffs from people who thrive after them.

Sitting in a corporate role wondering if there's more?

This one's for you.

Full story in the video. Link in comments.

The recruiters who fail aren't the ones without experience.

After working with 400+ people who've started their own recruiting businesses, the pattern is clear.

The ones who struggle make these seven mistakes:

1. Waiting for the "perfect time"
Start while keeping your 9-5.
You don't need to quit to build.

2. Undercharging because you're new
Standard recruiting fee is 20% of first-year salary.
A $100K placement = $20K fee.
Charge what the work is worth.

3. Trying to be everything to everyone
Pick one industry. One role type.
Specialists charge more and close faster.

4. Spending hours on manual outreach
Automation lets you reach 500 hiring managers while you're at your day job.
Check your inbox. Reply to interest. Book calls.

5. Leading with "I'm a recruiter"
Hiring managers hear that 20 times a week.
Lead with "I have a candidate who matches your role."

6. Taking every client who says yes
Bad clients drain time and kill confidence.
Choose quality over quantity.

7. Overcomplicating the pitch
Clients want one thing: the right candidate.
Keep it simple.

Which mistake are you making right now?

Dear recruiters, it’s not just about going independent.

You’re far more likely to succeed when the right systems are in place.

Here are six things successful independent recruiters do differently:

• Focus on one hyper-specialized niche
 (Phil made $50k+ just placing physicians)

• Use candidate-first outreach
 (Not “just checking if you’re open to opportunities”)

• Build direct relationships with hiring managers
 (Skip HR gatekeepers)

• Run lean operations
 (Madison bills $150k a year in about 10 hours a week)

• Prioritize quality over volume
 (Ginny landed a major client with just two or three strong candidates)

• Leverage automation and systems
 (Stop manually searching job boards all day)

The best recruiters can bill from anywhere.

Great independent recruiters build:
 Their own brand.
 Their own processes.
 Their own future.

February is when hiring activity starts to pick back up.
 This is the window to start building.

If you want to learn how this works, DM me.

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