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

There are officially more pickleball players than founders in America.
Not sure if that’s a good or bad stat..

Maybe it says something, people are craving connection just as much as competition.

Founders League has done a great job with this. Every Monday they bring local founders together to connect, compete, and grow.

The shared vulnerability of being an entrepreneur turns into genuine community, and the pickleball just keeps it light and fun.

Bringing people together will solve most of our problems.

As we head deeper into the world of AI, communities like this and genuine meetups become even more valuable.

#FoundersLeague #Community #Founders #Leadership #AI #Pickleball

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

ADR is dead. 
The operators who win from here will master VPG, Value Per Guest 👇

Most hotel owners are playing the wrong game.
They focus on ADR and occupancy. The best operators build value across the entire guest journey.

The top hospitality brands didn’t tweak the model. They rewrote it.

• Soho House sold belonging
• Airbnb sold trust
• 1 Hotels and Amangiri sold a feeling
• Autocamp and Getaway sold disconnection

Here is what the best operators understand.

Traditional metrics stop at what a room earns.
VPG asks a different question:
How much value can you create for each guest before, during, and after the stay?

This starts long before check in.

From the moment a guest sees the brand online, we are already learning what they care about. Wellness content. Group travel. Nature. Pickleball. Yoga. Celebrations. Creativity. Restoration.
Every signal a guest gives us becomes the foundation for a personalized experience.

Once they book, we gather context.
Why are they coming. What they want to do. Who they are coming with. What matters most to them. Activities. Amenities. Goals. Special occasions. Moments they're craving to create.

For full property reservations, the data multiplies. When the bride signs up for lakeside yoga, the entire group sees it. That moment alone triggers FOMO, drives participation, and increases ancillary revenue inside a single stay.

Every touchpoint becomes value.

• Discovery
• Booking
• Pre arrival planning
• On site experiences
• Upsells and add ons
• Content creation
• Group dynamics
• Post stay retargeting
• Personalized re engagement

We collect it.
We curate it.
We turn it into higher revenue, stronger loyalty, more rebookings, and a brand that grows through community, not discounts.

This data directly improves our social strategy, our group sales motion, our pricing power, and our experience design. It helps us attract more of the right guests and book more of the right groups.

Most operators never see any of this because they only look at the room.
When your entire business is built around Average Daily Rate (ADR) and occupancy, you are literally chasing "average" performance.

VPG is the opposite.
VPG is how you create a hospitality business that compounds.
It is how you build brands that outperform spreadsheets.

The ones who master Value Per Guest will own the next decade of hospitality.
Everyone else will keep discounting to survive.

Follow Tim Ensmann to see how we are rewriting the rules of how experiential hospitality brands operate.

Bolt Farm Treehouse bought their land for $237K.
Today it's valued around $32M...
The wildest part 👇 

100% of their bookings come directly through social media.

Imagine walking into a bank with a pro forma showing "treehouses" pushing 90% occupancy, a $750+ ADR, and 100% direct bookings.
You’d get laughed out of the room 😂

But this is exactly why there's such a massive opportunity right now in boutique hospitality.

You have brand-driven, design-led properties with the ability to reach the exact audience they’re built for.
Yet most are still treating them like “traditional hotels” or “average short-term rentals.”

It’s like underwriting a hotel as a multifamily building...
or treating a short term rental like a long-term rental.

Sure, they're all "real estate" and the numbers sit on the same spreadsheet.
But it is not the same business.

Here’s the counterintuitive part:
• We own the real estate.
• We own the strategy.
• Why wouldn’t we also own the channel?

We still underwrite conservatively with the traditional metrics.
But we are playing a different game, the same way Bolt Farm does.

We look for assets in markets with real demand, then lean into our unique advantages, target the right audience, and operate in a niche that sits far outside of “average.”

Follow +Tim Ensmann if you’re interested in how hospitality is changing and learning about opportunities like this one.

Commercial real estate + social media = new rules

We saw a 13X return on total marketing spend from buyouts alone.
This doesn’t even include the 92% direct bookings we hit this quarter.

The new rules are simple.
Treat your property like a brand, not a building, and you get to play a different game.

Attention builds a following.
Story builds trust.
Trust fills the calendar.

This is where hospitality is headed, and what can be possible on commercial real estate.
Operators who master social media will be playing a new game.

Woodward Square Realty

One of the fastest growing Real Estate companies in Michigan! 

Home owners and buyers get experienced, marketing professionals that earn their commission! Woodward Square focuses on a unique approach with each transaction, with the utmost transparency and simplicity, making your experience extremely positive and manageable. Our agents are hand selected individuals that have experience in mortgages, appraisals, inspections, marketing and sales, which gives you a specialized advantage in this saturated market. 

Realtors! We are excited to announce we are expanding our offices and are looking for team players that can benefit from earning more money and leveraging our experience to streamline your transactions. If you're ready to work with a knowledgeable team, that makes your transactions easier to manage AND wants you to keep your hard earned dollars, reach out today!

Real Estate Broker, Owner

Paramount Mortgage Group

President

Rent Roll property management

Airbnb, and long term property management in Metro Detroit.

Co-Founder

M5 Property Holdings

Build rental portfolio, Provide leasing contracts, Execute repairs, Rehab and Rentals, Flips, Sales contracts, Investment analysis, and Property Management.

Owner

Bajoka Property Group

Review financial information to assist buyer and seller in decision making, Review properties for marketability and appraised value, Investment analysis, Write contracts for buying/selling/leasing, Negotiation, Assist with underwriting requests, field pre-closing issues and questions.

Licensed Realtor

London Square Specialty Services

Build out new team for Processing, Increased production and conversion rates from Sales to Funding, Establish a strong and positive work culture, Improved sales and salesmanship,  Coach team on rebuttals and selling challenges, Revamp software to improve functionality.

Processing Sales Manager

United Shore

Underwriter Trainer

Quicken Loans

Coaching, teaching, process development, process improvement, recruiting, training and development of mortgage underwriters. Worked with teams of 11-115. Conducted Divisional meetings for reward ceremonies, business updates and informationals for groups as large as 300.

Team Leader - Underwriting

Matthew McCall-Stillman, known as MyBrokerMatt, is a real estate investor, mentor, and entrepreneur with a $10M+ portfolio that includes short-term rentals, a boutique hotel, and creative investments. Together with his wife, Sam, he runs Host’D, a co-hosting company managing 36+ properties, and Host’D Design, which focuses on creating unique, high-value stays. Matthew also leads STR Legend, a mastermind group teaching investors how to scale short-term rental portfolios through deal structuring, partnerships, and creative financing.

Matthew is also developing an AI-powered tool to evaluate Airbnb and hotel property values in seconds, incorporating real costs, rehab needs, and unique amenities. Through his various ventures, he aims to make real estate investing simpler and more effective, helping others confidently grow their portfolios and succeed in the ever-changing rental market.

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