Jamie Thurlow

Member

Enterprise Business Development Leader @ PGM 🏡 | Strategic Prospecting Coach | 2023 PGM Rookie of the Year 🏆 | Mindfulness Advocate 🧘‍♀️

Hey, I'm Jamie! 👋🏼

I'm passionate about creative + strategic, research-driven outbound.

Resonating with prospects is hard - but not if you're consultative + authentic.

If this is your jam too, we should connect 🤝🏼!

A few of my recent milestones 🏆:

⭐ 2023 Porch Group Media Rookie of the Year
⭐ Top Sales Prospecting Voice
⭐ Featured presenter @ 2024 Sales Summit: Building your Brand for Sales Enablement on LinkedIn
↳ Workshop generated several qualified sales opportunities | $20k+ in pipeline revenue

🌟 BDR ➝ BDR Team Lead ➝ BDR Manager within 1 year
↳ Team generated ~$2.5MM+ in NB pipeline revenue: Year 1 @ PGM 🚀
🌟 Built BDR program from scratch, developing the process from interest ➝ discovery ➝ opportunity
🌟 Prospecting tech stack champion - vetted, implemented & trained team on PGM's new tools + platforms

Skill set:

✨ Team leader: Always UTD on BDR trends, strategizes with SLT weekly on new business initiatives
✨ ICP outreach approach: Quality > Quantity | Omnichannel
✨ ABM prospecting framework: Research-driven + trigger-led + value-prop by use case
✨ Skilled copy + ghost writer: Creates relevant messaging for BDR + sales teams to stand out in prospect inboxes/DMs
✨ LinkedIn advocate: Promotes + coaches team on personal branding, social selling, DM + voice note strategy
✨ Results-focused: Develops, drives and achieves individual and team-based goals | Corporate KPIs + OKRs
✨ Autonomous by nature: Independent self-starter
↳ Remote since 2020

Quote: "I love when prospects reply to my personalized & relevant emails with 'unsubscribe'" - said no one ever

Chief Floral Officer 🌸 | Mindfulness advocate 🧘🏼‍♀️ | Pet parent 🐾

Business Development Team Lead

In November 2023, I burned the boats.

I quit my job, sold my house, and drove 3,000 miles across the country to Idyllwild, California.

No job. Rising interest rates. STR competition heating up. Market skepticism everywhere.
But we saw an opportunity to build something people crave most today: connection, wellbeing, and extraordinary experiences.

After buying, renovating, operating, and selling 20+ vacation rentals, my partner Isaac J. Silverman and I saw some clear truths:

People love to travel in groups but hate sharing bathrooms.

People want experiences over things.

People want to leave a vacation recharged, not drained.

And yes, design matters.

So we doubled down.

We bought The Fern Valley Inn for $1.5M from an older couple who had been running it as a retirement hobby. With the support of 13 trusted friends and family investors, we reimagined it as The PineTree Hotel.

Here’s what happened in our first year:
• 3X property value: $1.5M → $4.5M+ in under two years
• $666K+ revenue (up from $108K in 2022)
• $257K in weddings, retreats, and full buyouts
• 25K social followers + 4.3K guest emails
• 1,406 reservations | 4.9⭐ on Google
• 21%+ cash-on-cash returns | Over 2X investor equity

Sometimes opportunity doesn’t show up in a spreadsheet. Sometimes it takes vision, belief, and relentless execution to see what others miss.

For a while, I thought I needed to “own more hotels” before sharing my story. But the truth is: The PineTree Hotel is proof of concept. People are hungry for experiences that recharge them, not just places to sleep.

And we’re just getting started.

We are already under contract on three more boutique hotels set to close in the next 90 days.

We’ve done it. We’re doing it. And now, we’re scaling it.

Ways we can work together:

👉 Invest in boutique hotels that you’d want to stay in
👉 Partner with us to acquire and grow properties
👉 Sell us a property with untapped potential

Drop me a follow or let’s connect, because what we’re building is only getting more fun.

Tim Ensmann

My first $100k+ commission check was a wake up call…
from Uncle Sam.

I remember the feeling like I finally “made it.”

Then I looked at what actually hit my bank account.

That was the moment it clicked.

Learning how to earn money is important.
Learning how to keep it is just as important once you know how to earn.

I didn’t need to be a CPA to do the numbers.
Back of the napkin math was enough.

At $200k
• California: ~$115k–$120k take-home
• Florida: ~$135k–$140k take-home

At $500k
• California: ~$260k–$280k take-home
• Florida: ~$325k–$350k take-home

At $1M
• California: ~$520k–$560k take-home
• Florida: ~$650k–$700k take-home

So you’re telling me if I make $1M, it might only feel like a little over half?

Why would I work twice as hard just to hand the rest away?
That would be my biggest expense… and then some.

That question changed how I thought about money forever.

I realized most people focus on income.
The wealthy focus on structure.

Most people pay taxes by default.
The wealthy pay by design.

Employees get taxed first, then decide what’s left.
Owners decide first, then get taxed.

That’s when I stopped obsessing over “more commission” and started asking better questions:

• How do I turn income into assets?
• How do I reinvest instead of extract?
• How do I use the tax code as a tool, not a punishment?

For me, turning income into assets meant this:

Instead of spending or stockpiling every commission check, I started redirecting it into things that could pay me back.

• Assets that produce income
• Assets that grow without my time attached
• Assets that the tax code actually rewards

Businesses.
Real estate.
Equity stakes that create cash flow, appreciation, or both.

Depreciation. Leverage. Cash flow.
All legal. All intentional.

Same income.
Treated completely differently.

The biggest mistake high earners make isn’t not earning enough.
It’s earning more without changing how they play the game.

If you’re good at sales, you already have the hardest skill.
Now the real unlock is learning how money actually moves, grows, and gets taxed.

I wish I learned that earlier.

I put together a free mini course on this exact topic, real estate, taxes, and structure, that I wish I had well before I started earning real commissions.

Feel free to check it out in the comments.

When was your first “wait… I owe how much?” moment?

Sales Guy → Boutique Hotel Guy | Helping you build an intentional life through boutique hotel investing

SDR → Multi-Hotel Owner
What I learned along the way

In 2016, I got my first sales job as an SDR at a small tech company in Tampa.

Zero business background.
Zero sales experience.
Coming straight from pre-med prereqs and soccer.

Owning three hotels less than ten years later definitely wasn’t on my bingo card. But looking back, a lot of what sales taught me shows up every single day as a hotel operator.

1️⃣ Lesson 1: Failure is feedback

Sales teaches you this fast. Rejection isn’t personal.
Someone hanging up on you doesn’t mean they hate you.
They don’t know you.
They don’t have time.
They’ve got their own stuff going on.

Your job is to stop taking it personally and figure out what actually happened.
That mindset translates directly into ownership.

I’ve lost a lot of time, money, and effort on deals, diligence costs, and bad hires. But I’ve made 10x that by staying in the game. If you can’t handle some losses, you’ll never get the wins.

The only things you truly control are mindset and effort.

2️⃣ Lesson 2: Time is money

Your top 20% of customers, accounts, and investors will drive 80% of your success.

Sales teaches you not to waste time on things that won’t pan out and to double down on the highest upside activities.

Not every lead is worth chasing.
Not every deal deserves your energy.

As an operator, where you spend your time, attention, and focus sets the ceiling of the business.

3️⃣ Lesson 3: Relationships compound

The real edge isn’t the transaction. It’s the relationship behind it.

Champions, customers, colleagues, bosses, investors, and partners compound when you invest in them the right way.

You become the average of the people you surround yourself with. They shape how you think, what you normalize, and what you believe is possible.

Sales taught me to play long-term games with long-term people. That mindset carries directly into ownership.

4️⃣ Lesson 4: Leadership scales everything

Eventually, you have to outgrow being an individual contributor if you want to build something big.

It stops being about what you can do.

Your people matter more than your individual performance. If a team is full of C players with a couple A players holding it together, that’s not bad luck. That’s a leadership failure.

As an operator, recruiting, upskilling, and building systems becomes the real work. You have to hire people who are better than you or who will be soon.

Sales didn’t just teach me how to sell.

It taught me how to think, how to lead, and how to build something that lasts.

Curious what lessons have carried over for you as your career has evolved?

#sales #Leadership #CareerGrowth #RealEstateInvesting #Hospitality #BusinessOwnership

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The IRS gives real estate investors a legal cheat code.
Most people never use it.

100% Bonus Depreciation is back.
And with cost segregation, you can turn your investment into some serious tax savings.

Here's how it works:

Normally, you depreciate property slowly.
27.5 years for residential. 39 years for commercial.

But cost segregation breaks the building into pieces that write off much faster:

▪️ Personal property → appliances, flooring, cabinetry, lighting, furniture (5–7 years)
▪️ Land improvements → parking lots, sidewalks, fences, landscaping, pools, patios (15 years)
▪️ Building systems → HVAC, plumbing, electrical, security, fire protection (shorter timelines)

With bonus depreciation, all those write-offs hit Year 1. Not decade 3.

Cost segregation lets you use 100% bonus depreciation to get massive tax savings up front.

Real example:

One of our investors put in $100K.
Got $125K in paper losses in Year 1.

What that meant:
✓ Still collected nearly 40% in real cash distributions 
✓ Still keep equity growth through appreciation 
✓ Use the $125K loss to offset some W-2 income (with their STRs), 1099, business income, passive income 
✓ Carry it forward if not fully used 
✓ Saved tens of thousands on taxes while still building wealth

This is why real estate is so powerful.

It's not just about the money you make.

It's about the money you keep.

#BonusDepreciation #CostSegregation #BoutiqueHotels #Airbnb #Investing #TaxStrategy

Hot take:
Mandatory sports or service would solve a lot of problems in the U.S.

Watching the Super Bowl yesterday
& seeing Sam Darnold and Kenneth Walker lift the Vince Lombardi Trophy after years of setbacks, trades, injuries, and criticism reinforced this belief even more.

This isn’t about politics.
It’s about human development.

Here’s why I believe this.

People who grow up playing sports or serving are statistically more likely to:
• earn more over their lifetime
• hold leadership roles
• stay healthier longer
• report higher life satisfaction

That’s not ideology.
That’s data.

Former high school athletes earn 5–10% higher wages on average.
Student-athletes graduate at higher rates than non-athletes.
Veterans and national service participants show higher workforce attachment and leadership representation.

And the traits behind those outcomes matter more than credentials.

1. You learn to think bigger than yourself
When the outcome is shared, ego disappears.
Communication sharpens.
Alignment matters.
If the team loses, everyone loses.

2. You learn how to fail and recover
Everyone loses eventually.
What matters is how you respond.
Resilience is built, not lectured.

3. You learn real teamwork
You cannot win alone.
You depend on others.
You’re held accountable.
You have to communicate and execute together.
That’s the foundation of any functioning society.

4. You learn discipline
No one likes 6am workouts.
No one likes giving up weekends or holidays.
But doing hard things when you don’t feel like it becomes normal
and compounds for life.

5. You experience real inclusion
Sports and service bring people together across income, race, politics, and background.
Same rules.
Same objective.
Respect earned through shared effort.

6. You build health early and keep it
The U.S. spends $100B+ per year on costs tied to physical inactivity alone.
Early movement habits are one of the strongest predictors of lifelong health, lower healthcare costs, and longer productive lives.

And yes, leadership reflects this.

A disproportionate number of Fortune 500 CEOs played competitive sports.
Not because sports make you rich
but because they train reliability, pressure management, and team execution
the exact traits leadership demands.

These aren’t cultural talking points.
They’re the inputs behind:
• GDP growth
• quality of life
• lower healthcare spend
• and social stability

Not everyone needs to be an athlete or a soldier.

But everyone needs stakes, structure, and something bigger than themselves
before adulthood.

Most of what we argue about today
doesn’t survive a real team or real service.

If sports and service build what society needs, why are they optional until adulthood?

Should I be an ACTIVE or PASSIVE investor?

Passive investing gets pitched as the finish line.
In reality, it’s just one form of leverage.

I spoke yesterday with an investor who just had his first daughter. He’s rethinking where to put his time, energy, and capital.

This is how I think about the decision.

Before buying a business or real estate, zoom out and ask:
• How much time will this actually take?
• How much capital am I committing?
• What’s the realistic return range?
• How long before this gives me more freedom, not less?
• Is this something I want to do long term?

That’s the tradeoff most people never price in.
Betting on yourself can be the right move.

But only if you’re fully committed to the time and effort required.
If you’re not, it usually isn’t.

A real-world example
(Same capital. 5-year hold.)

Option 1: Active Short-Term Rental Owner

Time Commitment
Market research, underwriting, negotiations, loans, inspections, renovations, website and socials, OTA listings, revenue management, PMS systems, hiring cleaners and maintenance, tax reporting, STR compliance, guest experience and reviews

Estimated Time (5 years)
Hundreds to thousands of hours

Capital Stack
Purchase price: $500,000
Down payment: $100,000
Improvements: $50,000
Total invested: $150,000

Returns (modeled)
Cash flow: ~20% annually ≈ $30,000/year
5-year cash flow: ~$150,000
Appreciation: ~3% annually
Value after 5 years: ~$580,000
Equity gain: ~$80,000

5-Year Outcome
Total profit: ~$230,000
Total returned: ~$380,000
Equity multiple: ~2.5x
IRR: ~20%
Significant tax benefits possible if materially active

Great return.
But it’s a job before it’s an investment.

Option 2: Passive Boutique Hotel Investment

Time Commitment
Sponsor diligence, market review, K-1 to CPA once per year

Estimated Time (5 years)
~20 hours

Capital Invested
$150,000

Returns
Cash flow: ~10% annually ≈ $15,000/year
5-year cash flow: ~$75,000
Target IRR: ~18%
Total returned: ~$343,000
Total gain: ~$193,000
Equity multiple: ~2.3x

This doesn’t teach you how to operate.
It teaches you how to allocate.

The passive route often has a slightly lower return profile.

But are hundreds to thousands of hours worth the incremental upside?

If even a fraction of that time were reinvested into your career or core business, could it outperform the spread?

Here’s the punchline:

On paper, these outcomes are remarkably similar.
The difference isn’t returns.
It’s who’s doing the work.

Active investing buys you control and skill.
Passive investing buys you leverage and time.

The real question isn’t what returns you can earn.
It’s what you want your life to look like while you earn them.

I’ve invested in multiple passive syndications and went active years ago to build the skills and track record to do this full time.

If you’re not eager to become a full-time property manager, passive participation is worth exploring.

I put together a free mini-course for this reason. Link in the comments 👇

In 2008, Elon Musk was weeks from bankruptcy.
Today, he’s nearly a trillionaire.

...worth more than the GDP of Switzerland.

18 years ago, he was sleeping on factory floors.
Teams were breaking.
Investors were gone.

There was no Plan B.
At one point, Musk said he had to choose which company would live and which would die.

That’s not strategy.
That’s survival.

Fast forward to today.
He runs companies across EVs, space, AI, satellites, robotics, infrastructure, and energy.

Combined value pushing close to a trillion dollars.

Same person.
Same intensity.
Same willingness to look unreasonable.

What changed wasn’t talent.
It wasn’t luck.
It was time and endurance.

Looking back, every major bet sounded insane:
• Electric cars wouldn’t scale
• Reusable rockets were a joke
• Buying Twitter was reckless
• Brain chips were science fiction
• Building an AI company was “too late”

Most people stop at ridicule.
He kept going through failure.

Not because he was certain.
Because quitting wasn’t an option.

There are very few people you can even compare this to. And I’m definitely not saying to go try and build a company like Elon Musk.

But watching even the richest person on the planet come within inches of being wiped out, repeatedly, is a useful reminder.

The early stage of anything meaningful looks messy.
It looks uncomfortable.
It looks wrong from the outside.

And most people choose comfort over cringe.

The difference between ideas that die and ideas that compound isn’t brilliance.

It’s who stays in the room when belief gets quiet.

Who's a founder or company that looked like a bad bet 10 years ago, but now seems obvious in hindsight?

Super Bowl ads cost $8M for 30 seconds.
Here’s why that’s a bargain 👇

Most people hear that and think it sounds insane.
Smart operators know it’s one of the best deals in business.

Here’s why.

The headline cost gets attention.
The real value comes later.

You are not buying conversions.
You are buying attention.

Attention creates memory.
Memory creates preference.
Preference creates pricing power.

When brands spend $16M to $23M all in on a Super Bowl campaign, they are not expecting immediate sales.
They are buying leverage.

Strong brands do not compete on price.
Strong brands create demand before the buying moment even happens.

This year, prediction markets let people trade on which brands would appear in the Super Bowl.

Think about that.
Brands became so culturally relevant that people bet real money on their presence.

That is not advertising.
That is cultural leverage.

And this is the part most businesses miss.

Brand is not a marketing expense.
Brand is a force multiplier.

It lowers acquisition costs.
It increases pricing tolerance.
It makes future sales easier.
It creates resilience when markets shift.

This logic does not stop with consumer brands.
It applies to real estate too.

Most hospitality assets are treated like commodities.

Location.
Occupancy.
Cap rate.

All important.
But none of it creates pricing power by itself.

Experiential hospitality works differently.
It is branded real estate.

The property becomes the product people want before they even check dates.

A strong hospitality brand does the same thing a Super Bowl ad does.

It creates memory and association.
It turns a stay into an event.
It makes guests choose you at a premium instead of shopping on price.

Here is what that looks like in practice.

Higher average daily rates.
More direct bookings.
Fewer OTA fees.
More group buyouts and retreats booked months in advance.
Less volatility when the market shifts.

Commodity hotels compete on Expedia.
Branded, experience driven assets compete on preference.

Brand is not decoration.
Brand is operational leverage.

When you build brand into hospitality real estate, you are not just buying property.

You are buying attention, memory, and preference.

That is what turns real estate into a compounding machine.

The Four Seasons increased website traffic 425%
without running a single ad.

No discount.
No promo code.
No influencer push.

Just one decision:
Be the setting for The White Lotus.

Here’s what that show actually delivered.

Season 1: Maui
• +425% website visits
• +386% availability checks
• Immediate surge in direct bookings

Season 2: Sicily
• +193% increase in website traffic
• Months of forward bookings
• Premium suite demand spiked

Season 3: Thailand
• National tourism authorities projected a material lift in luxury travel demand
• Booking inquiries accelerated even before full release

And the property-level numbers were only part of it.

The brand-level impact was massive:

• 11B+ global media impressions
• 500+ top-tier press stories
• 57% of guests now Millennials + Gen Z
• 88% positive viewer sentiment
• A $188K private jet itinerary tied to filming locations

This wasn’t a campaign.
It was demand creation.

Traffic surged.
Direct bookings climbed.
Demographics shifted younger.
Press exposure compounded globally.

When demand is created at the brand level:

Pricing power increases.
Volatility decreases.
Cash flow stabilizes.
Asset value compounds.

Most operators try to optimize conversion.

The bigger unlock is manufacturing intent before someone ever searches availability.

Brand is not decoration.

Brand is revenue strategy.

Supply is constrained.
Demand has shifted.
Pricing power in live experiences is real.

The 2026 Experiential Hospitality Report breaks down the data and unit economics behind it.

If you’re looking at how to balance AI with real assets, this is worth a read.

(Report in comments)

Why Experiential Hospitality Is Quietly Outperforming The opportunity isn’t complicated. It’s supply and demand. When you zoom out and look at hospita

Open article: Supply < Demand by Tim Ensmann • 3 min read

Only 21% of millionaires received ANY inheritance.
Just 3% received an inheritance of $1 million or more.

Yet 74% of Millennials believe most wealth comes from inheritance 
(And ~60% of my LinkedIn votes below)

That disconnect didn’t happen by accident.

Social media is powerful.
It’s a huge advantage when used well.

But when it becomes your primary source of economic education,
you start learning from viral takes instead of how things actually work.

And you begin absorbing ideas that sound good, but are simply untrue.

Like:

“Billionaires shouldn’t exist.”
Often said on a device built by a trillion-dollar company…

“Tax the rich more.”
The top 1% already pays roughly 40–45% of all federal income taxes.
Meanwhile, government spending runs into the trillions every year.

“Rent should be capped.”
Ask any group of serious economists and you’ll hear the same conclusion:
rent control lowers housing quality, reduces supply, and pushes prices higher elsewhere.
(One Harvard economist famously called it the quickest way to wreck a city without explosives.)

“The system is rigged.”
In reality, most American millionaires are first-generation wealth builders.
They didn’t start rich.

To be clear:
the economy isn’t perfect.

Inflation is painful.
Healthcare is a $h!t show.
Wages could absolutely be higher.

But real problems don’t get solved with made-up economics.

The idea that wealth is mostly inherited is simply wrong.
And it’s a convenient belief.

Because if the game is unfair,
you’re not responsible for the outcome.

While some people argue online, others focus on fundamentals:
discipline,
saving,
investing,
and long-term thinking.

The system has flaws.

But it’s far less broken than those who’ve never taken the time to understand it want you to believe.

What percentage of millionaires received an inheritance?

(Will share stat next week)

What percentage of millionaires in the US received an inheritance? 

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