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.

Ingenovis Health

Senior Contract Paralegal Specialist

Fastaff Travel Nursing

Senior Contract Specialist

Cordant Health Solutions

	Contract Coordination: Maintain the contract management database, Contract Logix, and review tool solutions to track renewal dates and alerts required for effective team controls.
	Paralegal duties: Assemble and maintain Corporate Books for various entities and acquisition documents. Coordinate IRS entity filings, LLC formation coordination, business licensing, and review SEC filings of acquired corporations. Various other paralegal duties including review and coordinate HR garnishments, employee termination documentation.

Paralegal

AxisPoint Health, Formerly a McKesson Company

	Process Improvement: Establish a process/folders to maintain vendor contracts.
	Controls: Create a log to track renewal dates and alerts required to exit contracts. Review OIG
 vendor exclusion list (monthly) and establish a process for control.
	Contract Coordination: Read contracts and reconcile which vendors perform services for any of our client contracts. Ensure vendors accountable to terms of client contracts where appropriate.

Vendor Project Contractor

Health Language, A Wolters Kluwer Company

Draft and review healthcare proprietary software contracts, analyze existing agreements and maintain contract database. Control contracts  (PSA, MSA, NDA, SOW and BAAs) from inception through approvals process and completion. Administered differing processes within dual divisions under one parent while developing internal processes for growth and union of the divisions. Manage Salesforce.com contract queues to track contracts through company internal processes and meet service level monthly and quarterly demands and deadlines.  Work with Contracts Director to review and implement updates to process roadmaps, project deliverables and time management.  Developed and update system tools for transparency and leveraging tools to minimize inundating follow up requests. Work with Executive Management Team and Sales Team to prioritize competing agreements. Assist in developing processes and procedures to memorialize a shared directory.

Contract Manager/Analyst

TriZetto, A Cognizant Company

Contract Position- Coordinate the work and inputs provided by multiple teams contributing content of the contract. Maintain ownership of the contract documents throughout the sales cycle, ensuring clearly articulated solutions that represent the content provided by subject matter experts that will deliver those solutions. Single point of contact and accountability for delivering a reviewed and approved contract document to the sales opportunity owner for presentation to and negotiation with the customer.

Contract Manager

OppenheimerFunds

Provide daily support to business units regarding specific RFPs, contracts/agreements for products and services related to general goods and services, (all NDA, PSA, MSA, SOWs) and software and network solutions. Contracts lead with strong emphasis on software licensing and infrastructure upgrades. Directly engage with Vendors, Business Units and the legal team to ensure risk free language and terms. Maintain competitive market data on relevant industries, and recommend new/different solutions or suppliers to enhance current services or items, or to secure optimum pricing and negotiate with suppliers for best price, service and quality. Weekly meetings to discuss and validate technical and business requirements with IT Infrastructure, Cyber Security and various Business Units to assist with the execution and implementation of Network Services  and leverage IT roadmaps with existing vendors. Cross-functional Software shared among multiple Business Units was our goal. Complete sourcing review along with Cyber Security and Compliance teams for risk analysis. Engage with vendor for complete risk review and SOC 2 information when necessary. Interface with the Legal Department for administration and facilitation of contracts/agreements and assist customers in development of business requirements / SLAs for contracts/agreements. Maintain accurate, current and auditable files and records. Work closely with Asset Management for deployment and renewal compliance and upgrades. Engage with team for innovative ideas and solutions throughout the procurement process. Evaluate and analyze pricing and terms. Monitor compliance with departmental and corporate guidelines/procedures and perform proper due diligence on vendors, such as financial stability. Engage in and guide Contract Approval and Policy Requirements and process enhancement needs. Draft the process manuals for The Contract Procurement Department

Contract Specialist-Purchasing -(IT)

Catholic Health Initiatives

Contract Administrator, ITS Business Operations Vendor Management (8/1//2012-12/28/2012) Contract Position 
Interact with Contract Analysts and ITS Vendor team to review and analyze contracts for facilitation of new contract database tool, Lawson. Assist in team process improvement for data input and design. Analyze existing contracts for accuracy, terms, dates, compliance and standardization. Liaison with accounting, legal, and procurement departments to ensure precision of contract data.  My role consists of a variety of functions including a hands-on approach to QA processes, test strategies and plans; establish and review of test methods; perform and participate in all aspects of verification; train other team members on process updates and write process manuals. My ability to anticipate and solve problems coinciding with my role in analysis of the functionality allows more accurate contract tracking from inception and governs department spending for accountability to projects.

Contract Administrator, ITS Business Operations Vendor Management

Allonhill

Compliance Paralegal (2/2012-6/2012) Downsized due to Federal Contract canceled
Assist General Counsel and the company with adherence to internal policies and procedures. Oversee internal polices and systems administration to ensure employees are compliant with all applicable audit proof practices concerning confidential information related to Federal Treasury dictates and contractual agreements with our clients. Governed onboarding and compliance processes for specific system access. Review, process and govern high profile litigation information related to the Federal Treasure Board’s Consent Order. Contract review and execution. Point person for communication with outside counsel. Worked with senior project management and Allonhill’s General Counsel to develop compliance protocols, monitor compliance with policies and procedures, track and manage communication with outside counsel, and produce thorough documentation to share with executive team. Developed appropriate controls to monitor and comply with existing policies and procedures. Liaison contact with IT for process implementation, improvement, and trouble solutions. Liaison for Client Services to assist with new deals and implementation of client access to our in-house systems. Controlled JIRA and Data Portal systems and updates.

Compliance Paralegal

Analytical review and evaluation of foreclosure materials to ensure compliance with relevant state and federal laws. Responsible for verifying and evaluating loan information using proprietary software. Detailed review for issues surrounding default servicing, foreclosure and loss mitigation dealing with residential mortgage loan processing, underwriting, and multi-state foreclosure.

Due Dilligence Analyst

StarTek

Executive Administrative Assistant to the Senior VP of Sales and Paralegal for in-house Counsel.A global business process outsourcing corporation: customer management solutions that provide front- to back-office capabilities utilizing the StarTek Choice delivery platform. StarTek Choice includes onshore, near shore, offshore, and StarTek@Home outsourcing alternatives.
Support point person for Senior Vice President of Sales and Marketing and paralegal for in-house SVP General Cou Managed calendars, set up meetings, conference calls and travel dates. Coordinated travel arrangements for domestic & international trips, including commercial air, hotel, transportation for” C” level executives. Set and created agendas for interviewees and new hires for onboarding process.  Coordinate arrangements for special events and team training sessions. Liaised with the various levels of global management on facilitation of meetings, virtual access for clients and staff. Prepared documentation/PowerPoint slides & facilitated weekly staff meetings in house and virtually. Compiled/distribution of notes for team collaboration and task oriented activities. Directed sales team to meet deliverables. Interfaced with team and management for review of Non-Disclosures, Statement of Works and multiple phases of contract facilitation. Managed global payment arrangements and documented process and facilitation of international notary requirements.  Worked with Adobe Connect-Pro and international video conferencing along with interfacing of intranet tools available to international staff.

Executive Administrative Assistant and Paralegal

SUMMARY: EXPERIENCE
Contract Administration: analyze, review, amend, draft and execute contracts.
Point person for Compliance protocols for employees, customers & interfacing for our clients.  IT Co liaison for onboarding/deboarding access and internal & external for initial, and trouble ticket, database access. •Heavy client/customer contact, interviews, opposing counsel; CT contact, multilevel corporate interfacing: stateside & overseas. Design onboarding process & new hire corporate introductions.•Assist C-level executives & managed calendars, travel, mtgs & agendas. Coord. seminars, team mtgs, weekly updates, visiting clientele. Facilitate calendaring for direct reports and case sch.: clients/courts/execs. •Assist trouble solutions, case dev., case facilitation & case management, e-filing state, federal and appellate Ct. Federal level Consent Order review & dissemination of confidential info.
•Litigation Manager: trial prep, meeting prep, affidavits, ex.& witness docs, subpoenas, service, depositions, compose motions, orders, and doc control. Assist Atty in ct-room proceedings.
•MAC PAC, IDocs, Adobe 9 (modifiable), Brief-Lynx (a hyperlink software), and Relativity experience
•Time slips; brief client, Prolaw; various time software
•Coordinate software access for peers; controlled administrative duties to facilitate office structure. Trained paralegals, guided interns. Maintained & facilitated equip. contracts, and software tools to upgrade office procedures•Docketing and document control on PC Law software..•Worked w/ Cloud Technology for hyperlinking -add case law to appellate documentation: Domestic to Class Action involvement. •Adobe Connect Pro; international video conferencing. Outlook, Microsoft Office, PowerPoint, Salesforce.com, JIRA administrator, Data Portal sys, Lawson, CMGT, Meditract

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