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:

Premium Luxury Storage | Real Estate Investor & Developer | Pro Skee-Ball Player | LP/GP ➡️ "DATA NOT DRAMA"

“We don’t have time to find and vet high-yield real estate deals.”

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(And no one wants to gamble on risky projects.)

Real estate investing feels hard for 3 main reasons:

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Adam Shapiro

GP Available: ~35% | ~$2.6M Remaining
Areas like this don't come around often. 

If you are in a 1031 exchange, this opportunity was structured with you in mind.

Located 25 minutes from Phoenix Sky Harbor International Airport and adjacent to the new GSQ District, this extended-stay Hilton development sits in one of Arizona’s fastest-growing corridors.

Property Highlights

• 123-room, all-suite format
• Near Goodyear Ballpark (MLB Spring Training)
• Minutes from State Farm Stadium & major West Valley employers
• High-growth suburban Phoenix submarket

Extended-stay hotels historically perform well in markets driven by corporate travel, relocations, healthcare, and infrastructure expansion — all active in the West Valley.

CAPITAL STACK

• Total Project Cost: ~$30.69M
• Total Equity: ~$7.67M
• GP Available: ~35% (~$2.6M remaining)

This is a single-asset LLC structure.
You invest alongside us at the GP level — not into a blind pool or REIT. 
Direct equity ownership in the hotel.

TARGET RETURNS (Based on Underwriting)

• 5-Year Avg Cash-on-Cash: ~33%
• Modeled 5-Year IRR (sale scenario): ~47%

HOW THE PARTNERSHIP WORKS

• GP-level participation alongside sponsor
• Quarterly cash flow distributions once stabilized
• Pro-rata ownership based on equity contribution
• Net cash flow after debt service and operating expenses flows directly to equity partners

BUSINESS PLAN

Develop → Stabilize → Cash Flow → Refinance when appropriate.

Long-term ownership is the base strategy.
Underwriting includes a modeled Year 5 sale scenario.

If you’d like access to the deal room and full underwriting package, message me directly, or email me adam@capstaq.com 

OR book call here https://lnkd.in/eJFZ8dkn

– Adam

Turning income into legacy | Featured across NextaVest, Capstaq, TrustEQP, & Crowdvest (GP,LP,JV)

Since day one, I had a clear vision on LinkedIn.

(3 main things)

→ Share the real journey behind building in commercial real estate.
→ Document the wins, the losses, and the lessons.
→ Inspire others to think bigger about ownership, legacy, and impact.

Not just highlight deals, but explain the discipline behind them.

Over time, this platform has grown.
Nearly 40,000 of you are now here.

That’s incredible.
But the number isn’t the real milestone.

What matters more is what has come with it:

→ Investors reaching out to explore opportunities

→ Sponsors looking to structure smarter capital stacks

→ Meaningful conversations that turned into real partnerships

→ Messages from people who took action because of something I shared

I’ve had people come up to me at conferences to talk about a post. I’ve had operators tell me they adjusted their underwriting after reading something here.

I’ve had investors say, “I’ve been watching for a while and now I’m ready.”

That’s the real win. Because LinkedIn isn’t just a platform.

It’s a bridge. A bridge between ideas and execution.

Between capital and opportunity.
Between ambition and alignment.

Yes, I’m grateful for 40,000 followers.
But my bigger goal?

→ Work with more serious investors
→ Create more aligned partnerships
→ Place more equity into strong commercial real estate
→ Build businesses that outlast market cycles
→ Make measurable impact through disciplined investing

If you’re here just scrolling, you’re missing the point.
This space works when you engage.

When you ask questions.
When you challenge ideas.
When you build relationships intentionally.

I’m here to build real connections with people who are serious about ownership.

Who knows where one conversation might lead?

Bet on yourself.
Stay consistent.
Engage genuinely.

You might be one introduction away from your next big move.

Thank you for being here.

The next chapter is about scale, impact, and execution.

If you’re an investor or operator in commercial real estate - drop me and let’s build something meaningful.

🚀

In 2007, my life changed.

It was my 3rd year in business, and I closed a massive deal on a shopping center in Westchester:

Sale price: $40,700,000
Office cut: $1,250,000
My fee: $625,000

The buyer? Lerner Heidenberg.
And I was just 26 years old.

I called my friend Greg and said, “Let’s buy a car.”
I dropped $250,000 on the one you see in the pic below.

Did I love it? Absolutely. I drove it everywhere.
But was it worth it? That’s for you to decide.

Would you have spent it the same way… Or made a different move?

Share what you think in the comments or just DM me. Curious to exchange a conversation.

From a $100 decision → to $40M transactions

Look, numbers mean nothing.
They’re a great scoreboard.

But real business success is built on people.

That’s exactly how my journey in commercial real estate accelerated → through relationships, not spreadsheets.

Years ago, I wasn’t sitting on institutional capital.
I was sitting with curiosity.

I invested $100 into a book that shifted how I thought about income, leverage, and ownership.

That small move led me into rooms I wasn’t “qualified” to be in yet.
One of those rooms changed everything.
It wasn’t a glamorous boardroom.

It was a conversation. Simple, direct, unplanned.
We started talking about deals.

Then risk.
Then vision.
Then long-term ownership.
The mutual spark was there.

We stayed in touch.
Compared underwriting notes.
Challenged each other’s assumptions.
As the conversations deepened, so did the trust.

And eventually, so did the deals.

One of those early collaborations led to a $40M shopping center transaction, a defining moment in my career.

Over time, those same principles became the foundation for what we do today: connecting serious sponsors with serious investors and structuring equity the right way.

The main lesson?

If you want to build a quick deal, you can do it alone.

If you want to build lasting wealth, build with the right people.

P.S.

Big opportunities rarely announce themselves. Sometimes they start with a small investment in yourself…

Or a simple conversation that most people would overlook. 🚀

How I turned $0 into $700M in assets
 
(And how you could be a part of this too)
 
Mindset: Played the long game

• Never chased quick wins
• Said no to 95% of deals
• Built with focus, not speed
• Didn’t rely on market luck relied on math
 
Strategy: Thought like a bank, not a gambler

↳ Underwrite 2 x to 9 x opportunities
↳ Only buy assets with real income
↳ Target $5M–$250M properties
↳ Go for growth markets before they explode
↳ Always invest alongside my investors (skin in the game)
 
Execution: Relentless, boring, repeatable

- Closed deals in 4 countries
- Raised $195M+ without fancy suits or jargon
- Created cash flow from day one
- Focused on tax strategies that compound
- Build Trust. Then built more.
 
Capstaq today:

• Strategic assets only
• 100% focused on income, not hype
• We help clients build real generational wealth
• Not with hope. With data, structure, and grind 

Want to build your empire without rolling the dice?
 
DM me and let’s talk.

I had 15 posts go viral in these last few months.

But all of them made me realize one thing:
Getting likes & attention doesn’t make you cool.

Sure, it's a great thing.
But there’s a lot more to it.

Using my profile, voice, ideas, experiences…

I’m able to:

→ Share my experience on career growth
→ Raise awareness on important topics
→ Get investors to do business with us
→ Talk about business, real estate 
→ Inspire others to seek better
→ Truly IMPACT other lives

Putting yourself out there opens doors you’ve never thought existed. However, it also requires significant vulnerability.

Overall, it is a gateway to a better world. 
To the creation of a better community.

Remember:

These posts are not just strings of texts
They are a stepping stone to something bigger.

P.S.

What was one good idea you recently read or posted about?

Hi, my name is Adam and I took action before I was ready.

→ I didn’t have institutional backing
→ I didn’t have a perfect roadmap
→ I didn’t have a long track record
→ I didn’t have certainty

But I stopped waiting for the “perfect” moment.
Instead → I started building the future I wanted.

Years ago:

→ Making calls that went nowhere

→ Hearing more “no” than “yes”

→ Studying deals late at night to understand what others already knew

→ Wondering if raising capital and structuring real estate was “too big” for me

→ Feeling the pressure of performance and expectations

And still moving forward.
Me today:

→ Structuring commercial real estate equity
→ Working with serious sponsors and investors
→ Closing transactions that once felt out of reach
→ Building long-term partnerships instead of one-off deals
→ Helping investors move from income to ownership

How did it happen?
I embraced the reps.

The underwriting.
The follow-ups.
The uncomfortable investor conversations.
The deals that fell apart.

And I stayed in the game long enough for momentum to show up.

Today, through Capstaq, we connect accredited investors with institutional-grade commercial real estate opportunities and help sponsors secure aligned GP & LP equity.

And right now, we have an active opportunity open.

(Allocation window closes soon.)

If you’re serious about building ownership in commercial real estate:

→ Send me a DM
→ Or schedule a time through my profile

Let’s see if it’s a fit.

P.S.

I believe everyone deserves access to real ownership, not just headlines about it. That’s my intention behind every investor relationship we build.

P.P.S.

If this resonates, share it with someone who’s still waiting for the “perfect” moment. They might just need the push. 🚀

Most people talk about diversification like it’s a stock portfolio.

But when markets shift, 
The conversation changes.

The investors who last the longest understand something simple:

You’re not just diversifying money. You’re diversifying risk, demand cycles, and economic drivers.

A grocery-anchored center survives because people still need food. A hotel thrives because people still travel. Medical buildings stay full because healthcare never stops.

Different assets.
Different demand.

Same goal: resilience.

In a world that changes faster every year, concentration feels comfortable… until it isn’t.

The strongest portfolios today aren’t built on one bet.

They’re built on balance.

Would you agree on that?

Construction starting at Homewood Suites by Hilton Orlando.

Raise filled in 2 weeks.

In real estate, speed follows conviction.
Capital moves when the deal makes sense.

Orlando isn’t slowing down and neither are we.
Orlando

Dirt moving.
Capital deployed.
Execution underway.

This is what it looks like when underwriting meets demand.

If you’d like access to our deal rooms and full underwriting packages, message me directly, or email me adam@capstaq.com 

OR book call here https://lnkd.in/eJFZ8dkn

You don’t need a whiteboard, a mastermind, or a 5 a.m. routine. 

I’ve met investors who replaced their 6-figure jobs with 4 rental properties.

I’ve spoken with operators who skipped the endless coaching programs and built $1 Billion dollar portfolios by focusing on one thing:

→ Buy boring assets. Keep them full. Don’t overcomplicate it.

You don’t need another productivity hack.
You need leverage.

Real estate gives you:
→ Cash flow while you sleep
→ Appreciation while you play fetch
→ Write-offs while you walk the dog

No burnout. No endless Zoom calls. No nonsense. Just a simple business, a happy life and a tail wagging at the door.

Thoughts?

I don’t post to impress.
I post to create clarity.

So when someone says:

“I trust your thinking. I come back because you explain the why, not just the numbers.”

That tells me something is working.

And clarity builds trust.
That trust builds conversations.
And conversations create opportunities.

And over 20+ years in commercial real estate and investment marketing, I’ve seen that play out again and again. 

And that's how these results were achieved too:

→ $2.7B portfolio, 39 markets, 400+ active investors.

 → Analyzed thousands of hours of market data and underwriting, delivering 300% ROI for clients. (internal figures as part of data-driven strategy).

Those numbers matter, but they’re proof of process, not the point.

My approach has always been:

1 - Look at more deals than most people see in a lifetime.
2 - Analyze them. Question them. Stress-test them.
3 - Only move on the ones that hold up under scrutiny.

If you’re evaluating deals right now, or want to understand where the strongest risk-adjusted opportunities are today:

Send me a message.
I’ll walk you through:

What I’m seeing;
What I’m avoiding;
What kind of deals we're doing ourselves.

And if you’re here to challenge ideas, ask questions, and connect intentionally, thank you.

Let’s keep building intelligently. 🚀

- Adam

We have an opportunity that just became available in Alabama... 

A Holiday Inn Express. 

This is an existing operating hotel, not a ground-up development.

Holiday Inn Express Fairhope, Point Clear by IHG 19751 Greeno Rd, Fairhope, AL 36532

Minimum investment is $500K, with ~8.2% cash-on-cash returns and 18.9 % GP ownership.

If you'd like to get more details, comment "CURIOUS" and I will send you over the information

PS) Or just email me at adam@capstaq.com

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