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

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.”

This is the #1 wealth-building problem for professionals and investors who want to grow passive income without managing properties.

Some investors we’ve partnered with have seen portfolio growth of up to 300% ROI in <36 months -

⭐ Some people who trust our services:

Christopher Martinez (Private Investor)

Sarah Lee (Investor & Business Owner)

Daniel Edwards (Entrepreneur)

…and many others.

Most investors know they should have real estate exposure in their portfolio…

But let’s be real —

Most don’t have the time to research, underwrite, and manage properties.
(And no one wants to gamble on risky projects.)

Real estate investing feels hard for 3 main reasons:

You don’t know how to identify the right deals early.

You’re tired of complex structures and hidden fees.

You’ve got better things to do than manage tenants or maintenance.

We simply do this for you.

🏢 Crowdvest: Unlock Premier Real Estate Opportunities

A data-driven platform that helps qualified investors access exclusive, high-yield commercial real estate deals — with passive income potential built in from day one.

Including:
✅ Access to institutional-grade investment opportunities
✅ Pre-vetted properties with stable tenants and strong cash flow
✅ AI-driven deal sourcing through our SPHERE platform
✅ Transparent reporting and investor communication

🔒 Safe:
All investments are structured for long-term stability with strong tenant performance and margin of safety.

💰 Don’t burn through capital:
Avoid speculative bets — we only buy when value is baked in.

⏱️ Timeline from start to results:
Start generating passive income within weeks of funding your first deal.

📈 Case Studies:

Mystic Woods (Tallahassee, FL – Multifamily): 23% IRR over 3 years

Shoprite Center (Ellenville, NY – NNN): 15% IRR over 3 years

Burnt River Farms (Ontario, OR – NNN): 13.5% IRR over 3 years

Wilmington Realty (Wilmington, NC – Multifamily): 19% IRR over 3 years

✍️ How to start:

Copy and paste the link below to access your personalized portfolio of exclusive real estate opportunities — free for qualified investors:

👉 https://crowdvestllcc.com/?utm_source=LinkedIn

Adam Shapiro

The real reason professionals avoid real estate

It’s not lack of interest.
It’s lack of clarity.

Most professionals already believe real estate belongs in a long-term portfolio. 

What holds them back isn’t returns, but uncertainty around how to evaluate risk, structure, and timing.

PwC’s Emerging Trends in Real Estate highlights that investor hesitation often stems from complex deal structures, opaque underwriting, and difficulty assessing downside risk, especially for those without institutional resources. 

When visibility drops, confidence follows.

Confusion doesn’t create caution.
It creates inaction.

I’ve seen this firsthand. 
When investors are given clear assumptions, simplified reporting, and transparent downside scenarios, decisions happen faster. 

Not because risk disappears, but because it becomes understandable.

Capital moves when clarity replaces complexity.

Clarity is the most underrated asset.

If you want to cut through complexity and evaluate real estate opportunities with confidence, remember this:

the structure matters as much as the deal.

Turning income into legacy | Featured across NextaVest, Capstaq & Crowdvest

The type of real estate deal that will quietly outperform in 2026

It won’t be the loud one.
It won’t trend on social media.
And it won’t rely on optimistic projections.

The deals that outperform in 2026 will share three unglamorous traits.

First: structure over story.
Strong downside protection. Conservative leverage. Simple, transparent economics.
In uncertain cycles, structure does more work than appreciation ever will.

Second: tenant quality over asset class.
Cash flow doesn’t come from buildings. It comes from people and businesses that can reliably pay.
Long-term tenants with durable demand will matter more than the label on the deal.

Third: margin of safety over maximum return.
In the next phase of the market, capital preservation will quietly outperform capital aggression.
The best deals will not chase the highest IRR. They will survive stress without drama.

What we observed across portfolios this year reinforced this shift.
Deals with modest projections but strong fundamentals delivered steadier results than aggressive, headline-driven investments.

That’s not exciting.
But it’s effective.

“The best investments rarely need explaining.”

As 2026 approaches, disciplined investors will stop asking
“How big can this get?”

And start asking
“How protected am I if things go wrong?”

The answer to that question will define who quietly wins next.

If you’re evaluating real estate through that lens, you’re already ahead of the curve.

2025 proved that “busy investors” are actually the smartest ones.

Not because they hustle harder.
But because they don’t confuse activity with progress.

This year made one thing very clear.
The investors who performed best were not the ones glued to spreadsheets, touring properties every weekend, or chasing every “hot” deal.

They were the ones who understood something deeper.

Busyness forces discipline.

When time is limited, decisions become sharper.
Noise gets filtered faster.
And unnecessary risk becomes unacceptable.

Data backs this up.
Across multiple portfolios we reviewed in 2025, investors who focused on fewer, better-structured opportunities consistently outperformed those trying to do everything themselves.

Why?

Because they optimized for systems, not effort.
They delegated research.
They demanded clarity.
And they only committed capital when downside protection was already built in.

In practice, this meant:
• Fewer deals
• Cleaner structures
• Stronger tenants
• Predictable cash flow

Busy professionals didn’t miss opportunities this year.
They missed distractions.

And that turned out to be the advantage.

　 “Time scarcity doesn’t weaken judgment. It sharpens it.”

As we head into 2026, the question isn’t
“How much time can I give to investing?”

It’s
“How well is my time being protected?”

If you’re a professional who wants real estate exposure without turning investing into a second job, this conversation matters.

The smartest investors I know aren’t less busy.
They’re just better supported.

If this perspective resonates, you already know what to do next.

How AI is changing real estate sourcing

AI doesn’t replace judgment.
It improves it.

The real advantage of AI in real estate is not automation. 

It’s speed to insight.

PwC’s Global AI Study shows that AI can dramatically accelerate productivity and decision-making. 

Some analyses suggest efficiency gains of up to 40% when patterns and risks are surfaced earlier than traditional methods. 

In a market where the best opportunities disappear quietly, that speed matters.

Data accelerates discipline.

In practice, I’ve seen how AI-supported sourcing surfaces opportunities before market noise distorts pricing. 

When data handles the first layer of filtering, human judgment becomes sharper. 

Time is spent evaluating quality, not chasing volume.

AI doesn’t tell you what to buy.
It helps you see what others miss.

“Technology sharpens human decisions.”

The question isn’t whether AI will change deal selection.

It’s whether you’ll use it to see what others miss.

How legacy wealth is actually built

Legacy is consistency over time.

Most people associate wealth with timing or a single breakout decision. In reality, lasting wealth is built through repetition, discipline, and durability across cycles.

History consistently shows that long-term ownership of real assets outperforms speculation, not because returns are always higher in any single year, but because downside is managed and compounding is allowed to work uninterrupted.

Wealth is not an event.
It is a system.

I’ve seen this play out with investors who prioritize stability over excitement. By focusing on durable assets, aligned structures, and predictable cash flow, they’ve built portfolios that survived multiple market cycles without constant intervention.

The goal was never to win one deal.
It was to stay invested long enough for time to do the heavy lifting.

“Legacy favors patience.”

If you’re thinking beyond short-term wins and toward something that holds up over decades, remember this:

what you build matters less than how consistently it can endure.

Why transparency builds investor confidence

Trust is built through visibility.

Most investors don’t lose confidence because performance fluctuates. 

They lose confidence when they don’t understand what is happening or why decisions are being made.

Research from firms like Deloitte and PwC consistently shows that transparent reporting and clear communication materially improve investor trust and long-term engagement, especially during periods of uncertainty. 

When information is accessible and understandable, investors are far more likely to stay committed rather than react emotionally.

Investors stay when they understand.

I’ve seen this firsthand. 
When reporting is clear, assumptions are visible, and dashboards show both progress and risk honestly, anxiety drops. 

Questions become more thoughtful. Conversations become more strategic. Confidence replaces guesswork.

Transparency doesn’t eliminate risk.
It eliminates unnecessary doubt.

“Confidence grows where clarity exists.”

In the long run, transparency is not a reporting feature.
It’s a trust strategy.

What most investors misunderstand about fees

Fees matter.
But structure matters more.

Most conversations around fees focus on percentages. What gets missed is alignment.

When incentives are misaligned, trust erodes. Not immediately, but over time. Investors begin to question decisions, priorities, and whether outcomes are being optimized for performance or for payout.

In real-world investing, incentives define behavior.
They shape how risk is taken, how conservatively assets are managed, and how long-term value is protected.

I’ve seen this play out clearly. When fee structures are transparent and aligned with investor outcomes, commitment increases. Investors stay invested longer, ask better questions, and make decisions with more confidence. Not because fees disappear, but because expectations are clear.

Negotiation focuses on price.
Alignment focuses on outcomes.

“Alignment beats negotiation.”

Before committing capital, it’s worth looking beyond what you pay and asking how incentives actually work once the deal is live.

Want clarity before committing?

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Scot Chisholm

Adam Shapiro

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Adam Shapiro

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