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.

Vanta

Solutions Engineer

Siteimprove

Director - Presales & Value Engineering 

Submittable

Manager, Customer Success

Spot

Spot is the virtual hub for your organization– bringing the spirit and utility of being in the same physical office to a digital experience.

- Easily share multiple screens, stickies, images, and documents. It's as easy as dragging and dropping.
- Use an existing template or build from scratch. Everything is completely customizable from the floorplan to the furniture.
- Engineered and optimized specifically for a web experience. Anyone can join instantly with just a web browser.
- Meet in realtime and stay connected afterwards. All the accommodations of team chat and statuses built directly into the workplace.

Head of Customer Success

Outreach

Senior Manager, Solutions Consulting

Manager, Solutions Consulting, EMEA & US 

Lead Solutions Consultant

Outreach is an enterprise communication platform for sales. We make enterprise sales organizations more efficient and effective by optimizing their communication process for sales reps and team managers. We provide a unified communication platform with an intuitive interface that helps sales reps communicate more effectively through any channel, and provide managers with the tools to monitor and improve their team’s performance.

2017: Solutions Consultant Excellence Award
2017: Company Core Value Award: Ownership

Solutions Consultant

ACTIVE Network

Manager - Technical Sales Engineering

Lytx Inc.

At Lytx (formerly DriveCam, Inc.), we harness the power of data to change human behavior and help good companies become even better. Our flagship product, DriveCam powered by Lytx™, sets the standard for driver safety in the industries we serve. We protect drivers from more than 500 commercial and government fleet clients worldwide who drive more than 20 billion miles annually. Our clients realize tremendous ROI by lowering operating and insurance costs, while achieving greater efficiency and compliance. Most of all, we strive to help save lives – on our roads and in our communities, every day. Lytx is privately held and headquartered in San Diego. 

Duties: 
C-Suite Engagement
Pipeline Management
SaaS Product Knowledge 
Coordinate with Sales and Marketing teams to execute successful marketing campaigns
Use online resources to map out organizations and determine potential initial points of contact
Conduct WebEx and Program demonstrations to prospective clients
Attend Conferences and Trade shows upon request
Expand and Maintain current sales libraries and marketing tools

Achievements: 
Q3: 100% of Quota
Q4: 106% of Quota

Client Development Manager

Currently managing the Market Response Representative Team for clients inquiries regarding cloud based tools in the Youth and Education, Faith, and Ski & Attractions. 

Responsible for developing, implementing, and training 8 representatives to qualify all leads and distribute across >50 Account Executives

Market Response Representative - Team Manager

As an Account Manager I spent time consulting with existing clients on best practices regarding their cloud based management tools. In addition to the consistent communication with clients, I was also responsible for finding opportunities for growth and expanded revenue for ACTIVE. 

- 230% of quota Q2 2013
- Q2 Youth and Education MVP (Nominated by Youth and Education Team)
- Software Subject Matter Expert (SME) involved in strategic product demonstrations to over $1M in prospective and existing business.

Account Manager

I work with summer camps and programs throughout the nation, assisting them in setting up online registration software that helps them build their outreach to the local community. 

If you're interested in marketing your camp on ACTIVE.com, keeping in touch with parents throughout the year, or hearing the success stories of camps throughout the nation, get in touch with me today! AJ.Forkner@active.com or 425-415-4443

Account Executive

Chameleon Technologies Inc.

Chameleon Technologies’ is a quality based IT Staffing Firm based in Kirkland, WA. Our mission is to enhance the relationships established with candidates and clients by adhering to the highest standard of customer service and satisfaction. Using a unique methodology for finding professional candidates, Chameleon thoroughly screens each individual with in-person interviews, technical testing and the review of professional references. The company then matches the career goals and skill sets of candidates to the needs of its established clientele, offering market leaders in the technology, financial, government, insurance, healthcare, manufacturing, utility, and retail sectors a simple solution – well suited talent.

Technical Recruiter

WorkSource Snohomish County

Providing employers in the greater Snohomish County area alternative solutions for their hiring needs. I work with the On-the-Job Training and Work Experience programs, offering employers high caliber candidates for their workforce, with the added bonus of training incentives.

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