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.

Ob Portu Ventures

At Ob Portu Ventures, we are curating exclusive real estate venture capital opportunities for our valued limited partners, while building a mindset-driven community of industry leaders ready to win together! Adjacent to building Ob Portu, Matt provides acquisition, entitlement and development consultation services for homebuilders across SWFL

Managing Partner

Taylor Morrison

Land Acquisition and Entitlements Analyst - Sarasota-Manatee / Treasure Coast

Agrawatt, Inc.

While working full-time in residential development, I collaborated with former colleagues at the Green Energy Development Startup to form AgraWatt, our attempt at digitizing the carbon credit marketplace.

The unique element of the biogas industry is that due to high capital upstart costs, developers rarely profit off of the energy (pipeline grade natural gas or biogas electricity) itself - profits are derived from the municipal credits that the clean energy production generates, which incentivize grid decarbonization and enable project feasibility. The main profit seeking marketplace for carbon credits is California's Low Carbon Fuel Standard (LCFS), a program that penalizes large carbon emitters through forced credit purchases via a cap-and-trade based system. Biogas project operators generate credits when their energy is "offtaken" (via accounting) by a vehicle in an LCFS supported state.

However, the offtake system is archaically controlled by select brokers, who squeeze sizable profits for simply shaking hand. With strong legislative tailwinds opening up new markets, AgraWatt aimed to digitize the offtake marketplace, which would have driven down exchange fees and enabled more  project development. Our greater goal was to digitize the ESG marketplace, effortlessly enabling both voluntary and involuntary carbon credit exchange.

Through daily internal collaboration, market feedback and sales campaigns, we crafted / pivoted through value-add market entrance strategies. With a mix of part and full time co-founders, my main responsibility was to drive high-level growth strategy and explore equity fundraising feasibility.

Ultimately, after a year of intensive pursuit and negative legislative outcomes, including attendance at the nation's largest Biogas end-of-year summit, we determined that the broker's standing in the industry was solidified at that time. Our CEO pivoted to feedstock offtake, founding a company that I currently reside on its Board of Directors.

Co-Founder, Head of Growth

Green Energy Development Startup

Fresh out of fall semester classes during my senior collegiate year, I was presented with the opportunity to join a rapidly growing startup raising capital in a relatively niche industry - renewable energy development. This company had vast aspirations of vertical integration, from biogas project development via untapped feedstock pipelines through functional vehicular offtake stations and commercial grade microgrid energy production. Coming in without a scientific or engineering background, intense research was required to even begin effectively communicating subject matter and upside potential.

Through unprecedented working conditions, I packed my bags and operated out of a hotel room in a foreign city, leading a team of 40+ engineers, biologists and salespeople of similar age, educational prestige and ambition. While establishing internal processes and team coercion, I was responsible for crafting the investment thesis pitch deck and valuation pro forma for equity fundraising review. Facilitating communication between internal teams / Board of Directors and thinking outside of the box was emphasized during an intensive stay in which 80 hour weeks were commonplace.

Ultimately, legal matters derailed the company shortly thereafter - However, lifelong business partnerships were formed, along with a fostered attraction for building from zero to one.

Lead Financial Analyst

SVN | Commercial Advisory Group

Commercial Real Estate Brokerage Intern

Sky King Unlimited Inc

Senior Sales Associate, Management Intern

SIESTA KEY BIKE & KAYAK, LLC

Supported daily operations at a family-owned recreational equipment rental shop, where ownership instilled the importance of the idiom "lifetime customer value". Heavily reliant on annual repeat vacation clientele and "spreading the good word", I was able to witness the results of 30+ years of "doing the little things" - kind gestures, accommodations within reason, and taking care of the customer. This exposure to doing business the right way has left a lasting impression as I build my own ventures from zero to one.

Business Operations Assistant

Russell Business LLC

As an intern with Russell Business, I gained my first exposure to entrepreneurial venture capital. Lead by an experienced multinational financier, I assisted the team with a wide range of projects in the pipeline, from a home service app in early stage development to live-work-play joint ventures. My responsibilities mostly included note taking, financial modeling and coffee runs.

Private Equity Summer Analyst

Today's Approach: Building a Real Estate Company centered around luxury residential development and business adjacent ventures. Upsized yields are waiting to be seized with our curated approach to real world private equity

Investors, fund managers, developers, mentors and other young hustlers - Let's connect !!!                       (bio continued)           

---------------------------------------------- bio-----------------------------------------------------

PASSION – WORK ETHIC – LEADERSHIP

I live by a prevailing philosophy of presenting nothing less than my absolute best, which connects to both my personal and professional goals. 

Professionally, I am focused on learning from and gaining exposure to the wide world of real estate development, immersing myself in an industry that I strive to lead in the near future. I continuously aim to display consummate focus, commitment and work ethic in every setting I face. My experience building startups emphasizes my high value in both dedicated work ethic and doing business the right way. 

Similarly, I apply utmost precision to my healthy living routine. I compete for marginal daily improvement through research and encouragement between my driven friend group, and then translate that same level of focus to my passion for healthy cooking. My principles in discipline, perseverance and integrity were fostered through my background leading youth and high school football teams.

Additionally, I am passionate about creating and maintaining mutually beneficial relationships. Football instilled the importance of bonding with, loving and trusting your teammates regardless of surface level differences. Indoctrinated with the idiom “lifetime customer value” through my experiences working at small businesses, I actively connect my skillset in relationship management with forward thinking entrepreneurial goals centered around how WE can get better together.

I am attracted to analytically-focused, entrepreneurial professionals that value team success, innovation and client satisfaction

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