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.

Cardinal Oak Investments

Creating opportunities for investors seeking stable, long-term income and wealth building through real estate limited and general partnerships investing in apartments. 

We acquire properties in emerging markets where rental demand is strong, the community is growing, and smart renovations will drive rent growth. 

We modernize stable but outdated apartments and create clean, comfortable and safe residential communities.

Multifamily Real Estate Syndicator

Alaska Airlines

My work at Alaska Airlines started as a consultant on a system being implemented for scheduling crews. Pilots and Flight Attendants are the lifeblood of an airline so getting the right system, made to work smoothly for these users, was one of the highest priorities. 

Make them unhappy and we would break the trust bond.

After a few short months I agreed to come on full time, then transitioned to other implementation projects. 

One key project was replacement of an outdated and dysfunctional accounting system. It was developed in the 80s. Hardly any programmers are around who can maintain this kind of code.

No one likes to think airlines have old software, but they all do. It runs and it's maintained, but these systems severely restrict business growth.

We also implemented a system for validating the integrity of a ticket purchase, identifying and preventing the many ways customers can perpetrate scams.

One of the many interesting roles I was able to fulfill was identifying all the customer facing roles in the company where someone is authorized to give away product for free. Free bags, discount codes, full fare tickets as a remedy for a customer issue. No one knew who had this authority, and much of it was not tracked. 

I talked to a lot of people in a lot of departments. Not sure I got them all but the work product I delivered led to major transformation of several internal systems. Big dollars in savings.

IT Systems Implementor and Product Manager

IT & Business Advisory Consultancies

I joined teams in various consulting roles that transformed organizations, delivered insightful and actionable work outcomes, and raised the collective knowledge and capabilities of nearly everyone we worked with. 

We managed projects, implemented software systems, led organizational changes, analyzed complex data, and created new markets for products. We brought experiences from a wide breadth of responsibilities, a unique capability that very few long time employees could come close to.

Consultants are not long in most roles. I had the good fortune to have served in more than 25 different roles as a consultant, on several occasions brought back repeatedly.

A strong satisfying feeling of making a difference is much more common for good consultants, something I strived for and needed.

Management & IT Consulting

Tideworks Technology

Entrepreneurial roles in engineering provide unmatched training in so many aspects of business, but especially management. I was able to utilize those skills for a company that built software for marine cargo terminal operations, Tideworks Technology.

This is the software that directs and manages the operations of a cargo terminal, the waterfront places in most big cities where cranes load and unload cargo, mainly containers. Nearly every movement around the terminal is planned and directed. The software can't fail, because then operations stop and a ship sits idle. 

I managed the software development teams for several of those products, set up collaboration tools to work with offshore teams, and led development of new products.

I developed an immense respect for engineering managers. The work is extraordinarily complex, expectations are high, and when it all comes together, gratitude naturally goes to the engineers. Good engineering managers embrace that dynamic, though.

Engineering Management

Business Startups

When you're sent packing from a company who no longer wants you, one direction we might turn is toward doing what we do on our own.

I knew the product, the market, the software tools, and a lot of customers who no longer had support because we were all shown the door.

That was my opportunity to create a new software system for this antiquated but modernizing market. This was the start of WinterCress Development.

After a few months heads down I emerged with my beta product and showed it to friends in the industry. 

They gave me good feedback, then became my first customers. 

After a few customers and endless hours in product support, I started hiring. Engineering, sales, and office support.

We grew the business over a 10 year time period and sold it.

But before we sold this company, we started another one. My partner and I had ideas for new businesses and we just went for it. We called it AwesomeCakes.com.

We raised seed funding, got the product developed, and launched the business. It started out great, proved out our model, and we had sales, but not marketing. That was going to be the next funding round but the market bottom fell out in the Dot Com Crash, and we had to close the doors.

All of the experiences we had that were packed into just one short time period keep coming back. Successes and failures. Proof that we grow from our failures.

Founder, CEO

Boeing, Locke Systems Inc

It is a rare opportunity when you can use your education to fill a role in something much bigger than any of us.

I developed software for aerospace projects at Boeing. One of them, the Inertial Upper Stage, launched satellites from the back of the Space Shuttle. 

It is a featured exhibit at the Museum of Flight in Seattle.

I had a small, but interesting, role in a huge project and discovered my passion at the time was for bigger impact.

A very small but feisty company, Locke Systems, beckoned. They had eight people including three developers. I was the fourth. Then one by one in six months each of them quit. I was learning the business and the code.

The business was software for Facilities Maintenance Management and Plant Operations.

New customers were complaining about software not working. I was talking them out of calling their lawyers while getting the software to work. 

Then they became happy customers, we got back on our feet, and I validated why I wanted a bigger role in customer success.

The company was sold to a much bigger company, my role changed, and we started creating new products.

Until they shut us down and let us go. All in one incredible day.

Software Development

Acquiring exceptional wealth-building real estate for my investors Helping them build more fulfilling lives through financial strength

📈I help people reach financial security
🦉I educate and demonstrate - how you benefit from investing in apartments, realistic expectations, how to analyze opportunities
💻I have helped people of all backgrounds but specialize in helping tech professionals who can't see a path to financial freedom
👨‍👩‍👧‍👦I bring investment opportunities to people who need strong returns, income, predictable outcomes, and shelter from taxes and market turbulence. 

I founded Cardinal Oak Investments to create opportunities for stable, long-term investments in the safest and most reliably secure types of real estate, multifamily apartments. Through general partnerships with other experienced managers, we create real estate syndications to invest in apartments in strategic growth markets in the U.S. 

My extensive experiences with software development, management of technology teams, and implementation of large software solutions at Fortune 500 companies were invaluable skills to help my success in real estate. 

Now I create opportunities for investors seeking stable, long-term income and wealth building through real estate, and limited and general partnerships investing in apartments. 

My company acquires properties in emerging markets where rental demand is strong, the community is growing, and smart renovations will drive rent growth. We modernize stable but outdated apartments and create clean, comfortable, and safe residential communities.

Sharing my experiences through speaking engagements, guesting on podcasts, and publishing a newsletter I’m constantly looking for opportunities to help others get to the next level in their real estate investing, wealth planning, and passive income opportunities.

John Todderud

3 Ways to Get Your First Multifamily Deal

(Without Big Money)

Buying your first multifamily property can feel intimidating. But it’s not impossible.

You don’t need millions to start.
You need persistence, time, and strategy.

Here are 3 ways to begin 👇

1️⃣ Partner with experience
2️⃣ Build relationships before you buy
3️⃣ Raise from people who believe in you

Every investor starts somewhere.
And the first deal is where the real learning begins.

What’s holding you back from your first deal?

3 Ways to Get your First Multifamily Deal

When occupancy is low, you have 2 choices.

First, recognize who’s breathing down your neck.

Would it be the lender? They don’t want you to miss your mortgage payment.

How about investors? Are they expecting a distribution?

What if you didn’t have either? 

That’s your first option. Sit and wait. Tough it out. Let your competitors lease up at below market rents.

How many of us can afford to do that? Almost none. 

Your second choice becomes obvious because it’s your only choice.

You can’t raise rents when occupancy is under 90%.

Every owner hits this point eventually.
The smart ones know what to fix first.

When vacancies rise, focus on filling units before pushing rents.

Here’s why it matters:

• Happy tenants renew longer
• Full buildings build steady cash flow
• Strong occupancy attracts better financing

Before talking about rent growth, check these:

• Marketing consistency
• Maintenance and curb appeal
• Speed of response to prospects

Once occupancy stabilizes, rent growth follows.
Get the sequence right, and the numbers will too.

What do you prioritize first?

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