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:

Empowering Entrepreneurs | Build Systems & Grow Consistently | Scale Ventures with Impact · Tech × Infrastructure × Regeneration

👉 https://sara-kukovec.kit.com 

Grow consistently as an entrepreneur:
with systems, technology, and the right people to build remarkable companies. 




Hey, I'm Sara! 👋

I build the infrastructure and systems our future needs.

Growing up in Slovenia's nature taught me balance, resilience, and long-term thinking. Basketball shaped my perspective: teams outperform individuals, discipline beats talent, strategy wins.

As an Industrial Engineer, I managed construction sites, led research projects, and developed large-scale projects. I've built high-performing teams, represented investors, managed assets, developed business models, and run companies.

But after years of building, I recognized something crucial:

💡 Real impact isn't just about WHAT we build — it's about WHO builds it and HOW they make it happen.

My journey evolved from building physical world to building solutions and companies. While shaping startup ecosystems, I shared my expertise and that of other professionals by publishing books, including my series 'Building the Future Today' – sharing knowledge crucial for a better world.

This path led me to found Builders & Creatives (B&C), where I help visionary founders succeed with solutions that truly matter.

Since becoming a founder and learning from the best, I know:
Creating a valuable solution is only the beginning – bringing it to market, making users & people happy, creating fans, respecting our planet, while nurturing a sustainable, joyful founder journey is where the magic happens.

As a value-focused system thinker, I operate at the intersection of four domains: Personal Growth, Business Operations, Infrastructure Knowledge and Tech Capabilities (AI).

How I help founders, investors, and leaders:

🔍 Pattern Recognition – Seeing connections others miss
🎯 Leverage Points –Finding the 10% that delivers 90% of results
🌍 Problem-Solving – Market-fit solutions for real challenges 
🤖 People & Tech Value – Unlocking new value at the intersection

I cut through noise to focus on what drives impact, turning strategies into results and solutions into market success.

I believe the future is built by those who dare to create. Let's make sure you're leading it.

Our future depends on working with nature, not against it – regenerating us & our planet as we build what matters.

I'm a pragmatic visionary and long-term playmaker. 
If this resonates with you, let's connect.

www.sara-kukovec.com

Sara Kukovec 🌍🌱🏗️

Claude is one of the most valuable tools available right now. And it's evolving incredibly fast. If you want to use, build, and design agents with Claude, here's everything you need in one place.

I originally built this for myself.
There are incredible resources out there. The problem is they're everywhere. Anthropic docs here. A YouTube tutorial there. A GitHub repo somewhere. A newsletter you forgot to bookmark. By the time you find what you need, you've forgotten where you saw the other thing.

So instead of writing another LinkedIn post with a dozen links nobody saves, I built a page to learn Claude. 

Free and open for everyone.

→ https://lnkd.in/d28e4rhU



I use Claude daily, for my company, my clients, and with my partners. Writing, research, strategy, content, automation, creating and building.

Here's what's on it: 
140+ curated resources across 3 skill levels and one clear path:

→ Use Claude: Projects, Artifacts, Memory, Web Search, Deep Research. The features most people never fully explore.

→ Build with Claude: The API, Claude Code, Context Engineering. From your first API call to real production workflows.

→ Design Agents: MCP, Skills, the Agent SDK. Where Claude connects to your tools and works autonomously.


Deep dives into:
⤷ Cowork: Multi-step tasks on your desktop. Reports, spreadsheets, presentations, research synthesis. 

⤷ Claude Code: Agentic coding in your terminal, IDE, and browser. 

⤷ Claude Skills: Reusable instruction folders that turn Claude into a specialist. 

⤷ Context Engineering: The discipline that replaced prompt engineering. 

⤷ A 7-step path from "understand how Claude works" to "design agent systems for production." 

⤷ 60+ experts: Anthropic's core team, pioneers, creators, YouTube channels, newsletters, and communities.

Every link goes to the original source. Official courses. Engineering blog posts. API docs. Original infographics. Claude's Constitution. The complete Skills guide. All verified, all current.



I built this with Claude itself, multiple sessions of research, structuring, writing, and link verification. One HTML file on GitHub Pages.

We're in a moment where how we work, build, and create value is changing faster than most of us can keep up with. 

You don't need to be technical. You don't need a background in AI. You just need to start.

The best investment right now is the time you spend learning to work with these tools directly. Not reading about them. Actually using them.

→ https://lnkd.in/d28e4rhU


Sara

Sara Kukovec  🌍🌱🏗️

Last year, Katrin J. Y., CEO of the Swiss Future Institute, traveled to Mainz. I invited her to my home and we spent an evening with co-authors of our book "Innovations, Women Creating the Future". Brought together by Claudia Rankers, who makes encounters like these possible every year.

Katrin and I have a lot in common. But one topic runs through every conversation we have: 
How is AI evolving and how do we ensure this technology is shaped responsibly across business, the economy, and society rather than rolling over us?

She founded the Swiss Future Institute | Masterclass | Membership | Future Symposium | Consulting with a conviction: to foster diversity and connect AI technology with the human factor. Diversity in technology and data quality is the starting point for everything that matters.



This year, I joined the AI Future Council at the Swiss Future Institute. 

Together with:
Isabel Hartung · Stefan Remhof · Patrick Hanhart · Anne CHEVRIER · Daniel Sengstag · Michel Rudin · Dr. Anna Penninger · Tina Ghafurian · Till Trojer · Diana Perez · Felix Beilharz · Jochen Mai · Wolfgang Poly · Bernd Ziethen · Dr. Matthias Kreysel · Martin Jacobs · Wendy S. · York Scheunemann · Prof. Dr. Katrin Winkler · Jutta dos Santos Miquelino · Michael Lanker · Melanie J. Lennert-Anliker · René Gonthier · Cathrin Harrison · Ralf Hörnig · Saqib Majeed Sheikh · Dr. Karen Wendt · Antonios Gkikakis, PhD · Ulrich Irnich · Dr. Dominic Gorecky · Cédric CHEVRIER · Dr. Charles Pierre Salvaudon d’Audiffret 

…and many more. The full list of Council members is in comment below👇



The future of AI technologies will not be decided in labs alone. It will also be decided at tables where the right questions are asked.

If AI & this intersection matters to you, I'd like to invite you to the FUTURE SYMPOSIUM - Bridging AI to Human Impact: 

📌 March 26 - 27, 2026
Switzerland, Zurich
Link to agenda and tickets: https://lnkd.in/dhmgYsmh

I will be there as a speaker, bringing practical experience from recent years, from both a European and a US perspective. Two ecosystems that approach AI very differently. I look forward to meeting many of you there in person. 



More news on technology and AI development in the coming weeks 😊 

Sara

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