Scot Chisholm & Co. 

Every week I tackle management, operations & startup topics that are helping 100,000+ people become better leaders.

Scot’s Newsletter

Highland

Highland is a “school” & community for founders. If you're a founder/CEO, we should talk!

Founder & Chief Professor

Tall Timbers Holding Co.

A family office and holding company with wholly owned businesses, private investments, and property holdings.

Managing Director & Founder

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)

Haskill Creek

Haskill Creek is a new type of self-care store. Imagine a healthier & more holistic version of a Walgreens or CVS. Family owned business.

Co-Founder

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.

Co-Owner

Save Farmland

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

Abundant Montana

Board Member

AERO Montana

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

Advisory Board

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

Multi-time founder but operator at heart. 

Industrial engineer and lean six sigma nerd by training. 

Now I write about management, operations & startup topics that are helping 200,000+ people become better leaders.

scotchisholm.com/newsletter


MY BACKGROUND ————— 

🚀 Founder of Classy, a SaaS platform for 10k+ nonprofits raising billions per year. 

🎗️Acquired by GoFundMe in ‘22 to create the largest giving platform in the world. Together we’ve raised over $30 billion for individual & nonprofit causes. 

🏔️ Founder of Highland, a private community & leadership “school” for high-potential founders. 

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

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

⚽️ 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 / speaking oppty? email: partner@scotchisholm.com

→ Join my free newsletter: https://scotchisholm.com/newsletter-linkedin-profile

→ Check out my private community for founders: www.joinhighland.com

Scot Chisholm

Sh*tty managers ruin lives. 
Great managers change them. 

I’ve managed hundreds of people over the last 20 years. 

One of my biggest takeaways is the massive difference between an average manager and a truly great one. 

But, here’s the truth:

No one starts out as a great manager (literally no one). 

And, becoming a great manager can be learned by anyone. 

Just focus on these 12 habits:

1/ Provide business context
2/ Set high standards
3/ Take full ownership
4/ Focus (then focus again)
5/ Create operating cohesion 
6/ Lead with data
7/ But be decisive 
8/ Let your team make decisions
9/ Don’t give sh*tty feedback
10/ Take feedback like an adult
11/ Listen more than you talk
12/ Always be learning

The gap in quality managers is large, but the right behaviors are simple. 

Focus on these 12 habits daily and you’ll be ahead of 99%. 

What habits resonated most?
Let me know in the comments 👇

⁂

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

12 insanely simple habits to become a high performing mana

Leadership is misunderstood.

Building Classy taught me that the best leaders aren't necessarily the ones with the biggest titles, or the ones who can charm a room.

Some of the best leaders in our 300+ person company were individual contributors at the very bottom of the org chart. Young managers. First-time team leads.

Over the years I started noticing what made these unlikely leaders so effective. They had traits that, quite honestly, my executives lacked at times. Including me.

Over time I boiled them down to 10 core traits that our best leaders always exhibited. It’s no surprise they rose fast within the company. Many are still there today, 15 years later.  

The very best leaders: 

• Clarify - Never assume everyone understands
• Believe - Push forward when everyone doubts
• Adapt - Evolve rapidly without ego
• Anticipate - Solve problems before they explode
• Persist - Get kicked in the teeth, get up anyway
• Empower - Create leaders, not followers
• Own - Own failures without excuses
• Hold the line - When quality dips and others compromise
• Always Learn - Learn and grow faster than the company
• Lead by Example - Live values when no one's watching

Most leaders start off strong in a few, but not all of these traits. You must intentionally develop them over time. It's a lifelong thing. 

But many executives forget this. Maybe they were great once. But they start slipping. They stop learning. They get cocky. I've seen this too many times. 

I don't care where you’re at in your career. Keep these traits in mind. And never stop developing them. 

⁂

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Top 10 traits of the very best leaders:

Every high performance culture starts with this… 

I recently asked a founder about his culture. And he started talking about free lunches and other perks. 

This is not culture. 

He was a coaching client of mine, so I nicely explained… 

Here's what real culture looks like: 
→ A shared purpose. Everyone understands and resonates with the 'Why'.

→ Excitement about the future. The vision is clear to all and it creates an almost kid-like excitement about the future.

→ Strong empathy and trust. Great orgs know if you neglect empathy, trust evaporates.

→ The correct level of accountability. People know you're building a championship team.

→ Mutual respect and encouragement. High performers have admiration for each other.

→ Hunger to learn and improve. Without being asked. That's the diet of champions.

→ Aligned financial incentives. Compensation that's aligned to the organization's top goals.

→ Career mobility. Lots of opportunity, with clear expectations around advancement.

→ Work-life balance. Clear boundaries that are enforced across the org.

→ Pride in the work. Numbers one through nine create an amazing sense of pride. You'll find yourself bragging about work to complete strangers.


When you get the culture right, people are excited to show up, employees self-manage, and retention is extremely high. 

And great business results naturally follow.

 ⁂

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10 signs of great culture.

Most people waste their leadership meetings. 

Do this instead: 

When I was building Classy I got this meeting wrong for years. We’d talk about everything BUT the important stuff. Too much time wasted on low-level “issues”. Too many tangents and distractions. Everyone left feeling:

• Confused
• Misaligned 
• Unaccountable

I talked to advisors and scoured the internet for help. But it took loads of trial and error to land on a meeting structure that actually worked. We stuck with it for nearly ten years. 

One of the major improvements was focus. Teams spend months setting goals only to let them collect dust. Your leadership meeting should be your #1 checkpoint for progress. 

Once we got “tight at the top” as a leadership team, everything started to change. More results, less talk. It became the tip of the spear of our entire operating rhythm.

To this day, I call it your most important meeting. If I only had one, it’d be the leadership meeting. 

The entire leadership team meeting structure is in the carousel. Copy it for your own company and let me know what you think. 

⁂

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How to nail your  leadership meeting every time:

Most people think goals fail because the team screwed up. 

They’re wrong. 

99% of goals fail because of poor leadership.

It doesn’t matter what framework you use…

→ OKRs
→ Rocks
→ SMART

If you’re sloppy with your approach, the company won’t hit its goals. 

That’s on you. 

I learned this the hard way, running a company with hundreds of people. 

Now I see it working with nearly 100 CEOs across all industries. 

Here are 7 non-negotiable rules that will make your goal-setting 10x better…

(regardless of your framework) 

⁂

Rule 1 –  
Focus (then focus again):

• Maximum three goals, period
• Goals aren't task lists
• Everything priority = nothing priority

Rule 2 – 
Always be measurable: 

• Three metrics maximum per goal
• Measure outcomes, not tasks
• "$1M ARR" beats "update deck"

Rule 3 – 
Challenging but realistic: 

• Impossible goals kill momentum
• Stretch without delusion
• No sandbagging, mutual accountability

Rule 4 – 
Never forget the ‘why’: 

• No context leaves team guessing
• Each goal deserves a 'why'
• 1-3 sentence rationale

Rule 5 – 
Track consistently:

• Break annual into monthly
• Weekly red/yellow/green updates
• Never leave dashboards stale

Rule 6 – 
Create accountability:

• Use leadership meeting
• Address every yellow or red
• 20% status, 80% solving

Rule 7 – 
Align incentives:

• Pay goals to comp
• Ignore the OKR purists
• Bonus plan is perfect for this

Does this resonate? 
What rules would you add?
Let me know in the comments 👇

 ⁂

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How to actually achieve your company goals in 2026

If there's one thing you do on Linkedin today... 

I'd be forever grateful if you'd consider applying, or sharing this role with someone you really respect. 

Christopher Himes & I started dreaming up this company about a year ago.  Now the dream has turned to reality. 

With a fresh round, a tiny team of insane talent, and a massive opportunity in front of us... 

We. are. ready. to. go!

Who wants to join us? 

p.s. We're not listing this company as "stealth" because that's dumb. But you'll learn way more about the market, opportunity and product when you apply. Trust me its badass. 

🔥

World Class Podcast

Every week, we bring you inspiring stories and actionable advice from world renowned entrepreneurs, investors & thought leaders to help you unlock your greatness.

Guests include:

Jim McKelvey - Co-Founder @ Square
Brad Garlinghouse - CEO @ Ripple
Keith Rabois - GP @ Khosla Ventures & Member of PayPal Mafia
Delian Asparouhov - Co-Founder & Chairman @ Varda 
Jack Abraham - Co-Founder @ Hims & Hers, Founder @ Atomic VC
Emil Michael - Chief Business Officer @ Uber
Howard Lerman - Founder & CEO @ Yext & Roam
Zeb Evans - Founder & CEO @ ClickUp
Matteo Franceschetti - Founder & CEO @ Eight Sleep
Steve Galanis - Founder & CEO @ Cameo
Peter Smith - Founder & CEO @ Blockchain.com
Ed Sim - Founder @ Boldstart
Ben Ling - Founder @ Bling Capital

Host

Quantum

Quantum is a new category of recruiting firm focused on building VC-backed AI, SaaS and Web 3 Startups from Seed through IPO. We don’t just place people, we build entire companies.

We partner intimately with Tier 1 VC's & Founders to assemble world class executive suites and full team build outs across Engineering, Product, Finance & Go-To-Market.

Our team is comprised of highly specialized .01% Recruiters that operate with next level precision, startup speed, and elite standards. Simply put, we're the firm Founders trust to run through walls and generate unparalleled results. 

To date, we've generated 500+ successful placements with hundreds of companies backed by VC's like Sequoia, a16z, Lightspeed, Coatue, Bessemer, Index and Craft Ventures.

Clients include: Character AI, Scale AI, Together AI, Hebbia, ClickUp, Rippling, Hume, Voyage AI, Alchemy, Lightspark, Yuga Labs, DyDx, Magic Eden, Moonpay, Verkada, Robin AI, Aptos, X1, Anomalo, Kandji, Chroma, Orby AI, Wisdom AI, Federato, Dream AI, MaintainX, Tavus, Foundry, ModernFi, vidIQ, Mosaic, NexHealth

Founder & CEO

ThroughYOU

ThroughYOU is a Non-profit on a mission to create equal access to quality education, clean water and medical care around the world. We envision a completely connected world where all human beings are empowered to create a brighter future, free from the constraints of poverty. 

ThroughYOU partners with world-class NGO’s to fundraise and build schools and clean water systems in developing countries. 

Our focus is three-fold:

1) We run campaigns to fully fund every project we take on.
2) We provide immersive experiences, where we build our projects in country side-by-side with the communities we serve.
3) We have a powerful community for on-going support and development to help every individual continuously blossom as leaders.

Our motto is simple: change can only happen ThroughYOU. 

When we unite as a community to take on the difference we seek to make, our impact can move the world.

Co-Founder, CEO

Speakeasy

Investor

Boardy

MadMen AI

ReevoAI

Flex

Hanover

CapStack

Investor & Founder @ Quantum | Building iconic teams for AI, SaaS & Web 3 Startups

"It simply doesn't get any better than Chris and Quantum. The golden standard in talent acquisition - they've been absolutely game changing for ClickUp and we wouldn't have scaled without them."

Zeb Evans, Founder & CEO @ ClickUp 🚀 (60+ placements from pre-funding to $4B)

👉🏽 𝐅𝐮𝐧 𝐅𝐚𝐜𝐭𝐬: Backpacked 30+ countries, broke 30+ bones (much better at recruiting than sports), became a Yoga teacher in India, taught English across Africa & Asia, and rode a motorcycle across Vietnam. Passionate about all things spiritual and personal growth. Obsessed with serving underdog Founders, taking on "impossible" challenges and winning big together. 

▪️ Co-Founder & CEO of 𝐓𝐡𝐫𝐨𝐮𝐠𝐡𝐘𝐎𝐔, 𝐈𝐧𝐜., a nonprofit on a mission to create access to quality education & clean water around the world. We currently build schools & water systems across Africa, Asia & Central America. 

▪️ Founder & CEO of 𝐐𝐮𝐚𝐧𝐭𝐮𝐦, a VC Search firm specializing in building full stack Executive, Engineering & GTM teams for VC-Backed AI, SaaS & Crypto Startups.

𝐕𝐂 𝐏𝐚𝐫𝐭𝐧𝐞𝐫𝐬: a16z, Coatue, Sequoia, Index, Craft, Bessemer, Quiet, Lux Capital, Paradigm, Human Capital, Felicis, Insight, Foundation, Uncork, Pear, Wing

𝐂𝐥𝐢𝐞𝐧𝐭𝐬:

AI: Character AI, Luma AI, Cartesia, Together AI, Scale AI, Orby, Tavus, Hume, Foundry, Hebbia, Chroma, Galileo, Credo, Wisdom, Shelf, Federato, Dream, Eve

SaaS: Rippling, ClickUp, Kandji, Verkada, NexHealth, Modern Health, Harmonic, Metadata, Applied Intuition, Kargo, Illumio, Kodex, Flock Homes, Flock Freight

Web 3: Alchemy, DyDx, Yuga Labs, Lightspark, Magic Eden, Aleo, Aptos, IronFish, Autograph, Moonpay, Gemini, Skolem, Sound xyz, World Coin, Story Protocol, Gensyn, Monad

✉  chris@quantumtalent.io 
💻 www.quantumtalent.io

Chris Vasquez

I'm beyond excited to announce our two newest Partners, Ches Courtney & Chad Rogers!

Ches was initially a good friend & client of Quantum -- one day out of the blue he called me and said "Dude, I want to join you guys." I broke the rules on our interview process and immediately said "F*** yes, let's do it." Absolute no brainer. Ches is the teammate everyone dreams of working with — he's a hardcore builder that drives big results while effortlessly elevating everyone around him. He's one of the most thorough, thoughtful and detail oriented operators I've ever met, on top of being a world class human with unquestionable integrity. He's someone I implicitly trust in every dimension, and would go to war with any day. 

Chad joined Quantum less than a year ago and has been an complete game changer for us. Part of me was surprised he joined, given the other insane offers he had on his plate. So happy he chose us. Chad quickly brought in some marquee clients & flawlessly executed on major projects. He brought new sales and execution strategies to the table we had never considered, that instantly inspired myself and our other partners to level up our games. I continue to be blown away by the reputation and respect he's built in the venture community, and working with him day to day, it's easy to see why.
He's a force of nature & extraordinary team mate we all feel lucky to work with. 

Congrats gentlemen, your success is inspiring and so well deserved!

Investor & Founder @ Quantum | Building world class teams for AI Startups

We're hiring at Quantum!

Offering $10,000 Referral bonuses for any successful intros through the end of this year.

Opportunity to partner with 250+ Tier 1 AI Startups / CEOs, drive massive impact on large team builds, learn from a world class team & build serious wealth. 

1) 2x Director of Recruiting - Engineering / AI (OTE = $500k-1M/yr)
2) 2x Director of Recruiting - Go-to-Market (OTE = $500k - 1M/yr)
3)10x Principal Recruiter - Engineering / AI (OTE = $300-600k)

Backgrounds we hire:
1) Founding Recruiter / Hands on Head of Talent specifically at Tier 1 VC Backed companies with rapid growth
2) $1M+ Agency recruiters from top firms

If you have next level passion for the craft, an undeniable track record & a fire to build... lets chat!

I'm pumped to welcome Alexander Forman  & Lauren Klemp to Quantum as our newest Directors!

Alex is impressive on paper, and even more so off paper if you spend 5 minutes with him.

- Top performer at Google, Mixpanel, & Uber, Head of Talent @ Runway.
- Whip smart, highly personable, full of positive energy
- Immigrant work ethic with an insatiable fire to win

Lauren is also total badass.  

- Entrepreneur who recently sold her startup recruiting company for XX Millions 
- High energy driver that leans into growth over comfort 
- Massive enthusiasm and love for the game of startups — you can't teach this! 

These two are builders in every sense of the word, and truly embody the quantum DNA.

I'm grateful to work with you guys, our future looks much brighter with you on the team.

Who are the BEST Internal Recruiters / Head of Talent / Agency Recruiters that specialize in building Engineering/Product/GTM Teams for VC-Backed Startups?

I'm selectively looking to mentor 2x world class recruiting operators -- will help you achieve your 10 year goals in 2-3 years.

- Earn $1-2M/annually and build a top tier personal brand in venture
- Invest in our clients and build an equity portfolio of Tier 1 AI Startups
- Get "handed" an insane book of business in 6 months that would take 5+ years to build alone 
- Get mentored by myself and our team of  .01% operators in startup/venture recruiting
- Join an electric, high camaraderie culture full of world class humans on a mission to level up together 

If you have an undeniable track record in building talent dense teams for technology startups & have an absolute FIRE to achieve your highest potential, I'd love to meet you.

DMs open (please share statistics/motives - will only respond to those who meet above qualifications).

𝗤𝘂𝗮𝗻𝘁𝘂𝗺 𝗨𝗽𝗱𝗮𝘁𝗲 (𝗡𝗼𝘃𝗲𝗺𝗯𝗲𝗿):

𝗤𝘂𝗶𝗰𝗸 𝗦𝘁𝗮𝘁𝘀:

 • 87 Candidate Offers 
 • 35 Placements
 • 16 New Clients
 • 5 New Team Members

We made successful placements across Eng Executives, AI Research, Applied ML & SW & GTM roles for 𝟮𝟳 𝗦𝘁𝗮𝗿𝘁𝘂𝗽𝘀:

Eve, Replit, Mercor, Reevo AI, AIM, Actively AI, AirOps, Architect, Brale, Capitol AI, Cogent Security, Detail, Elementum AI, Further AI, GigaML, Hanover Park, Latitude, Neuron7.ai, Optura, Orchard Robotics, Percepta, Rillet, Sieve, Traversal, Unify, Valerie Health, Stealth

We’re rapidly growing & hiring for the following roles:

 • 1x Partner (Product & Eng) - Executive Search
 • 5x Director (Product & Eng) - Scale 
 • 2x Director (GTM) - Scale 
 • 15x Principal (Product & Eng) - Scale

We’re exclusively looking for 1) Former 1M+ Billers in agency and/or 2) Founding Recruiters/Head of Talent/Agency Owners specializing in high volume, Tier 1 VC backed startups 

Offering $10k referrals for any successful intros.

Thank you!

Quantum is _the_ startup recruiting agency.  They've built an insane portfolio over the years, getting in early and helping build today's iconic companies (Rippling, Replit, ClickUp, Scale AI, Hebbia, etc, etc).  It tracks that they'd have top tier ops.

Check out the case study to see how Harmonic can be a superpower for recruiting agencies that focus on venture and private markets.

Congrats to Chris Vasquez and the team on what you've built so far.

Quantum 2025 Executive Offsite off to a great start.

Team has never been stronger and more locked in. Big things coming!

Grateful to work with this legendary team. Congratulations on the massive progress David Zhu Cindy Hao Clement Fang !

Today, I’m thrilled to announce Reevo is coming out of stealth with $80 million in funding.

I’m especially grateful to be backed by two of the best: Khosla Ventures and Kleiner Perkins. A heartfelt thank you to Vinod Khosla, Samir Kaul, and Mamoon Hamid for believing in our vision from the very beginning and supporting us in building something truly category-defining.

Reevo was born from our shared frustration with the fragmented, broken GTM tech stack we wrangled with in the past: data silos, lost context, broken insights, and manual upkeep of a house of cards.

As a technologist at heart, I couldn’t shake the feeling that there had to be a better way to run GTM, where the tools worked for the team, instead of the other way around. I have always believed in the power of individuals and building tools to help humans do their best. Growing a company is hard enough - let’s not make it any harder.

Together with my co-founders Cindy Hao, Clement Fang, and Curtis T., and an all-star team - many of whom have worked at multiple companies with me - we set out to build the platform we wished we had:

A single, AI-powered Revenue Operating System that unifies the entire GTM motion, from marketing to sales to customer success.

Thank you to Bloomberg for covering our launch! Read the full story here: https://lnkd.in/dhGx8KZz

#gtm #seriesa #startup #founder #ai #salestech #venturecapital

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