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:

This is the part of leadership no one prepares you for…

Going from IC to manager is hard.

But becoming a manager of managers is brutal. 

You’re no longer managing the work… you’re managing the people who manage the work.

Vanilla management advice no longer works. Instead, focus on these 7 things:

→ Provide clarity and context. If they don’t have context, they can’t give context. And their teams will be flying blind. Make sure your managers always know: Why are we here? Where are we going? How are we doing? Your job is to arm them with the information they need to lead.

→ Work through, not around. When someone skips your manager and comes to you with a problem, resist the urge to solve it on the spot. This robs your manager of the chance to learn and improve themselves. Listen. Ask questions. Then loop your manager in to address it. Build leverage through them, not around them.

→ Set a team rhythm. Establish a recurring cadence with your managers. Weekly or bi-weekly team meetings work best. Create a high-performance environment that focuses on progress against goals. But feels safe for the managers to help each other, unblock projects and always stay aligned.

→ Create additional checkpoints. Checkpoints ensure your managers stay on top of things. Your early warning system. 1x1s for coaching and calibration. Quarterly reviews for deep dives. Occasional skip-levels to stay connected. But don’t overdo your 1 on 1s. Great managers shouldn’t need tons of special attention.

→ Don’t do their job for them. When your manager is struggling, it’s tempting to pick up their slack. Don’t. They need to own the outcome fully. You can coach them, help connect the dots, resource things. But don’t do the work for them. They’ll never develop into a strong manager this way.

→ Create P2P accountability. Peer-to-peer accountability is stronger than top-down. Great managers don’t want to let their peers down. Review each other’s goals. Share progress openly. Set standards together. Your team helps you keep the bar up for everyone.

→ Avoid over trusting. It’s tempting to say: “They’re experienced, they’ll figure it out.” This is blind faith. When a manager is sending off smoke signals through any of the prior steps. Missing goal after goal. Showing up weak at checkpoints. With no correction on the horizon. It’s time to take action. Don’t trust forever. The buck still stops with you.

⁂ 

Putting it all together... 

How to manage managers: 

• Provide context
• Work through manager
• Set team rhythm
• Create checkpoints 
• Don't' do their job
• Create p2p accountability 
• Avoid over-trusting

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How to manage managers (even as a newbie)

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. 

🔥

Cannabiz Credit Association

Let’s elevate the cannabis industry toward better business. 

The Cannabiz Credit Association is the primary, member-based organization that advocates for better business practices and credit standards for cannabis creditors nationwide. The CCA believes that through the sharing of data, we can empower cannabis businesses to make better business decisions and raise the bar for extending trade credit. 

Trust. Transparency. Transformation.

www.cannabizcredit.com

Founder

CannaBIZ Collects

As Founder and Managing Partner at CannaBIZ Collects, Brett Gelfand operates the nation’s first and leading cannabis-focused collection agency. He is passionate about advancing the industry forward to protect good actors from the bad in the cannabis industry. 

While helping clients recoup their outstanding accounts receivables is his core mission, Gelfand takes great pride in his leadership role towards improving credit and collection practices in the cannabis industry.

CannaBIZ Collects has worked with over 1,000 companies and processed over $100M debt to date. 

CannaBIZ Collects is a no collect, no fee agency. 

"Grow Your Green. We'll Collect It."

www.cannabizcollects.com

Managing Partner

PAQCASE

As Co-Founder and CEO of PAQcase, Brett Gelfand is responsible for articulating and steering the vision of the company that created the world’s first gasket-sealed, child-resistant case for rolled smoking material. 

His responsibilities at PAQcase including high-level stewardship for partnerships with industry leading brands including Canopy Growth, ZigZag, Alien Labs, Justin Bieber’s Peaches, Seth Rogan’s House Plant, and Snoop Dogg’s LBS.

Brett sold his equity in PAQcase in April of 2022 to focus on other ventures. 

Premium. Preroll. Packaging. 

www.paqcase.com

CEO, Co-Founder

Colorado Product Services

Oversight of 60+ employees and 5 brands, including Jimi Hendrix edibles, Mountain Flower and Double Black Extracts. Maintained investor relations, built sales team, managed payroll/expenses, established financial budget/projections, led overall strategy, and helped grow the business from $0 to $500,000 in sales in less than 1 year.

Chief Executive Officer

Executive Vice President

Assistant to the CEO of a start-up cannabis wholesale company in the Western Slope of Colorado. Colorado Product Services owns a newly built 43,000 sq ft high-tech indoor grow warehouse, a 7,000 sq ft marijuana infused product facility, as well as a retail dispensary located in Carbondale, CO. Direct involvement includes: new product development, financial forecasting, budgeting, accounting,  social media marketing, web design, marketing campaigns, branding, equipment/packaging decisions, HR/ recruitment, management and oversight, investor relations, and sales strategies.

Executive Assistant

Protiviti

•Created risk analysis survey to identify key risk areas impacting client

•Automized team’s project log dashboard 

•Drafted planning and scoping memos for multiple audits

•Reviewed and tested over 12 controls for interim SOX testing

Strategy Consultant

Caterpillar Financial

•Initiated and designed the first market intelligence report for Cat Power group

•Organized and segmented industry research 

•Actively participated in various client and deal facilitation meetings

•Presented market intelligence report to Cat Financial executives and employees

Business Development

Student Managed Investment Fund

•One of twenty students selected in the 2014 graduating class to manage the $200K portfolio for the University of Georgia Foundation

•Prepared and presented buy/sell recommendations through fundamental analysis of equities 

•Actively watched and managed six securities in the technology sector

Technology Sector Associate

Leech Gary Asset Management

•Assisted in allocation and management of portfolios ranging from $500K to $50 million 

•Analyzed client portfolios, researched stocks, and pitched potential buy and sell opportunities

•Participated in weekly meetings to understand short and long-term strategy goals 

•Compiled reports comparing performance of ETFs and REITs

•Promoted new business by cold call sales

Intern

Campus Protein

•Expanded Campus Protein to the University of Georgia campus

•Supervised the distribution, inventory, and sales of workout supplements

•Managed three college representatives to sell and distribute products

UGA Division Manager

Craze Entertainment

•Entertained small to large social events including mitzvahs, concerts, fraternity and corporate parties

•Avg event cost ranged from $1,000 - $5,000 

•Responsible for the marketing, production, and management of the company

Owner

Managing Partner @ CannaBIZ Collects & CCA | 🌎 Travel | Innovative Disrupter | Helping companies collect their 💰

I’m driven by the challenge to build great businesses with great people to solve real problems. 

My career began in 2015 after being promoted to CEO of a vertically integrated cannabis company in Colorado, where I gained hands-on experience and deep insights into the industry.

Later, I co-founded a specialty child-resistant cannabis packaging business, where I served as CEO. In 2022, I sold my shares in the company, achieving a personal exit while the business continued operating independently.

Currently I’m the Founder & Managing Partner of CannaBIZ Collects, the nation’s first and leading cannabis-focused collection agency started in 2017. In this role, I work to support cannabis businesses in navigating the unique legal and financial challenges related to A/R and collections.

I’m also the founder of the Cannabiz Credit Association, the first trade credit group in the cannabis industry, where we provide tools for risk monitoring and credit assessments to help businesses make better financial decisions and manage risk effectively.

I earned a BBA in Finance from The University of Georgia, and today, I’m based in St. Petersburg, FL. I’m committed to exploring new opportunities, improving business practices in the industry, and mentoring aspiring entrepreneurs who are looking to make an impact.

Brett Gelfand

I'm excited to be moderating an important panel at #MJBizCon 2025. Let's catch up in Las Vegas this December 2 -5. See you at MJBizCon and use my 15% off discount code to attend: SPR25. 

Link to Registration: https://lnkd.in/dEU86_Qv

Recovering unpaid 💰 and reducing credit risk for cannabis companies | Founder @ CannaBIZ Collects & Cannabiz Credit Association (CCA)

The NJ market is starting to feel the same collection pressures that operators in CA, MI, CO, MA, etc have been battling for years.

Glad to see leading brands in the state working with us to get ahead of the problem, and not wait for it to blow up. 

A proactive credit and collections strategy beats the reactive scramble that has become far too common in cannabis today.

View company: Cannabiz Credit Association

We’re excited to announce that Jersey Smooth has officially joined the Cannabiz Credit Association community!

Jersey Smooth is a science-driven, research-focused cannabis brand rooted in New Jersey, committed to producing premium, flavorful extracts and vape products with precision and care. Their “gold in = gold out” philosophy ensures they source top-tier flower and extracts, delivering outstanding quality in every product. 

Their portfolio includes disposable vapes, cartridges, and pre-rolls, all crafted for a smooth, richly flavored experience — whether you're chasing potency, purity, or terpene complexity. 

As a family-owned business deeply rooted in its local community, Jersey Smooth brings not just innovation but also warmth, dedication, and a commitment to wellness.

We’re proud to welcome their leadership, craftsmanship, and passion for elevating the cannabis experience.

#WelcomeJerseySmooth #CannabisExtracts #VapeInnovation #CannabisCommunity #CannabisQuality #CannabisIndustry #CCAMembers

Collections has always had a bad reputation.

But when we get feedback like this from our clients, it reminds us why we do what we do.

At CannaBIZ Collects, we take on the messy side of the industry: the unpaid balances, the tough conversations, the stress most operators don’t want to deal with. 

So our clients can focus on growth.

We appreciate the trust so many brands have placed in us, and we’ll keep pushing to raise the bar and move this industry forward.

It's been harder than ever not to lean on AI for writing content or emails.. 

It's almost like needing your big bro/sis to proofread everything you write, before you ship it. 

I kinda hate it...

But at the same time, I know the power of AI "polishing" up us humans. Esp in business. 

Making our ideas more clear. More concise. And potentially more impactful.

So if technology starts doing all the heavy lifting for us

Where not only do we not need to check our own grammar, we technically don't even need to write without a few bullets of an idea. 

It's evident our brains are starting to atrophy. 

For me, I notice my previous confidence of writing a badass email or proposal has dwindled. 

One of my strongest attributes to close a deal or mediate a situation in business.

And now, its like ehhh this could probably be written better. Or I don't feel like putting in the energy to look for a word or phrase. 

I'm already seeing more and more AI created profile pics on LinkedIn. 

And can guess that 90%+ of posts are AI generated or at least re-worked.

So not only are the faces "nonhuman" now the content is too. 

As exciting as the AI technology is.... 

I am least trying to write on my own. Once in a while..

Who else is trying to resist the new ultra comfort of AI dependency at work or in their writing?

Or are most just leaning in... and accepting their brains are being replaced by tech.  Cause I go back and forth on this one.

Insider tip... If you're trying to reach the MJBizCon audience this year, give this a look. Show directory that goes to every attendee with maps, booth listings, and notes pages. 

Contact sales@cannapages.com or 719-205-4127 for more info (you can get a 20% CCA discount if you mention us). Last call for ad placements is Thursday 11/13

Flipbook demo: https://lnkd.in/dEYKX9f8

CannaBIZ Collects and Cannabiz Credit Association will be in there... you should too. 

Always great working with Nathan Johnson.

Getting stronger every day to help push our industry forward. 

CCA provides the first and only way to check real-time credit scores and risk in the cannabis industry.

We’re excited to announce that Order.co has officially joined the Cannabiz Credit Association community!

Order.co is a modern, AI-powered procurement and finance automation platform that helps cannabis businesses streamline their purchasing lifecycle — from requisition to payment — with full visibility, compliance, and control. 

With Order.co, operators can:
- Eliminate manual ordering and invoice tasks with automated procurement and AP workflows 
- Gain real-time spend insights and enforce approval workflows to prevent out-of-policy purchases 
- Unlock flexible net-terms (30/45/60 days) for all purchases, improving working capital and cash flow 

Leverage AI sourcing to optimize supplier selection. The platform’s AI recommends cost-effective suppliers based on price, availability, and vendor reliability.

We’re proud to welcome Order.co’s innovation and strategic sourcing leadership to our association. They’re empowering cannabis businesses to scale smarter, save more, and operate with greater financial clarity.

#WelcomeOrderCo #CannabisProcurement #FinTech #CannabisFinance #CannabisOperations #SpendManagement #CannabisIndustry

Pumped to be holding a panel with this amazing group of industry leaders on Thursday at 10:50am at #MJBizCon 2025. Let's catch up in Las Vegas this December 2 -5. Will be posted up at CannaBIZ Collects booth #7112.

See you at MJBizCon and use my 15% off discount code to attend: SPR25 Link to Registration: https://lnkd.in/djfR2YdB

Proud of the work our team is doing to uncover the gaps that rescheduling won’t fix. Tax relief is great, but without true credit visibility, cannabis operators are still playing with one hand tied behind their back.

Schedule III may remove 280E, but it won’t fix one of the cannabis industry’s biggest financial barriers — credit invisibility.

Even with potentially massive tax relief, most cannabis operators will still struggle to be seen by the traditional credit system. The major credit bureaus remain cautious about onboarding cannabis-related data as long as federal law hasn’t resolved the gap between state-legal markets and federal compliance frameworks.

And without credit reporting, improved cash flow doesn’t translate into better lending terms, lower interest rates, or stronger credit profiles.

In short:
 ✅ Better financials
 ❌ Still invisible to the U.S. credit system
Until federal banking reform addresses this gap, rescheduling alone won’t unlock true financial access for the industry.

📘 Read the complete analysis here - https://lnkd.in/gDH5pm2m

#CannabisIndustry #CannabisBanking #CreditReporting #ScheduleIII #CannabisFinance #CannabisBusiness #BankingReform

This poll may sound silly… but you’d be surprised by what we see everyday. Since these credit insights are now available for cannabis sellers.

Curious to hear from you, and any specific feedback on this via comments.

If you knew in advance that a buyer rarely pays their bills on time… would you still extend them terms? 

taplio

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The Battle

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