Success isn’t just about accumulating wealth. It’s about building a life with flexibility, purpose, and optionality.

I’m Dr. Dylan Reach, founder of Expedition Equity, a private investment firm focused on helping professionals build long-term wealth through private markets.

My background as an optometrist and business owner shaped how I think about investing. In medicine and business alike, discipline matters, incentives matter, and long-term thinking consistently outperforms short-term speculation.

After acquiring and scaling multiple businesses, I began allocating capital into private real estate and alternative investments. What started with a single property evolved into a diversified portfolio spanning real estate, private equity, and income-producing assets across multiple strategies.

At Expedition Equity, we focus on:

Capital preservation first

Cash flow where appropriate

Thoughtful growth over full market cycles

Most of the people I work with are busy professionals — physicians, business owners, and executives — who want their capital working efficiently without making investing a second job.

I use this platform to share perspectives on private markets, capital allocation, and building wealth in a way that supports an intentional life — not one that consumes it.

I live in Woodstock, Georgia with my wife and four children. Family, health, and giving back are central to how I define success, both personally and professionally.

https://www.ExpeditionEquity.com

Dylan Reach

Marinas are one of the most overlooked real asset classes.

Waterfront land is finite.
Permitting is restrictive.
Demand is growing.

And revenue is diversified:
		🚤 Slips
		🚤 Fuel
		🚤 Storage
		🚤 Maintenance

Scarcity plus recurring income is a powerful combination.

Private Market Investor | Long-Term Capital Allocation | Founder, Expedition Equity | Optometrist

No alternative text description for this image

I have a strong view on affordable housing investing:
If the strategy relies on forcing people out, it is not impact. It is extraction.

The most sustainable returns come from:
	• Operational improvements
	• Better management
	• Lower expenses through efficiency
	• Reduced vacancy through resident retention
	• Long term financing and thoughtful upgrades

Stability for residents often creates stability for investors.

That is what alignment looks like.

Some people do not think about self storage as an investment.
Until they notice how often they use it.

-- Moving between homes.
-- Downsizing.
-- Starting a business.
-- College students between semesters.
-- Contractors storing equipment.

Life creates storage demand.

That is what makes self storage such an interesting asset class.

It quietly sits at the intersection of several major trends:
	Population mobility
	Smaller living spaces
	Growth in small businesses
	E-commerce inventory needs

Unlike many real estate sectors, self storage typically has:
Short term leases
Flexible pricing
Low operational complexity

Operators can adjust rents quickly as demand changes, which provides resilience across different economic environments.

The result is an asset class built around everyday behavior.

People accumulate things.

Businesses accumulate equipment and inventory.

Life changes create temporary storage needs.

And when demand is constant, well located facilities tend to perform consistently.

Sometimes the best investments are not the ones making headlines.
They are the ones quietly solving everyday problems.

Think of liquidity like packing for a trip.

The things you will need during the flight go in your carry on.
Easy access. No hassle.

The things you will not need until you arrive can go in the checked bag.
Investing works the same way.

Some capital should stay liquid and accessible. That is your carry on.

Other capital can be allocated to opportunities that take longer to access.
Private investments are often the “checked bag” money.

They are not meant for immediate access, but in exchange investors may gain access to better pricing, stronger terms, and opportunities that do not show up in public markets.

The mistake is not investing in illiquid assets.

The mistake is putting money you might need soon into investments designed for the long term.

Cash value life insurance works best when paired with growth-oriented assets.

While private real estate, business ownership, or private credit focus on returns, cash value provides liquidity, stability, and tax efficiency.

Together, they reduce pressure and improve flexibility.

If you are curious how this pairing works in practice, I am happy to explain.

If you are investing for growth but not thinking about tax mitigation, you may be leaving a lot on the table.

One strategy many investors overlook is properly structured cash value life insurance.

For the right person, it can provide:
	• Tax deferred growth
	• Tax advantaged access to liquidity
	• Portfolio flexibility outside of market volatility
	• Estate and asset protection benefits

This is not about replacing traditional investments. It is about adding another tool for long term wealth planning.

The key is structure:
overfunded, designed for cash accumulation,
and coordinated with your broader tax strategy.

Have you explored where cash value life insurance fits into your capital stack?

A 1031 exchange does not have to mean buying another property and becoming a landlord again.

Many investors are using exchanges to move from active to passive.

➡️ Same tax deferral.
➡️ Less management.
➡️ More focus on portfolio design.

Sometimes the best upgrade is getting your time back.

Are you ready to switch from active management to passive investing? Let's discuss the options before you exchange another property for more of your time.

Most investors have a stock portfolio.

Very few have a private portfolio.

A private portfolio is built differently:
     • Income first
     • Real assets for durability
     • Growth through business ownership
     • Tax efficiency through structure

Public markets are liquid. Private markets are intentional.

The goal is not complexity.
It is control.

If you want to explore private markets and diversifying your portfolio, reach out to schedule a call.

Some of the most compelling investment opportunities are not startups.
They are businesses that already work.

Profitable companies with loyal customers.

Owners who built something meaningful over decades.

Strong local reputations and steady cash flow.

The challenge is that many of these owners are reaching retirement, and the next chapter for their business is not always clear.

That is where investment capital can play a powerful role.

By acquiring strong businesses and pairing them with experienced operators, investors can focus on improving systems, expanding operations, and unlocking growth that the original owner may not have had the time or resources to pursue.

The goal is not to reinvent the business.

It is to take something good and make it even better.

Sometimes the best investments are not about discovering something new.

They are about recognizing value that is already there.

When investors say they want “cash flow,” what they usually mean is predictable, repeatable distributions.

Our Income Fund is built around short-duration small business financing.

Capital is typically deployed for 6 to 12 months.

Businesses repay daily or weekly via automatic debit.

Target payback multiples range from 1.2x to 1.4x.

This structure creates something many portfolios lack: speed.

Approximately 14 to 15 percent of deployed capital returns monthly. That means the portfolio can be repositioned within 6 to 7 months if needed.

No leverage.
No capital calls.
No single asset concentration.

Short duration plus diversification is a powerful combination in uncertain markets.

If you want consistent income, look past the headline return and ask:
	What keeps the checks coming when life gets messy?

I look for:
	- Multiple layers of demand, not one customer type
	- Professional operations, not hero management
	- Reserves for surprises, not optimism
	- Financing that can survive higher rates
	- A plan for vacancies, maintenance, and downturns

Cash flow is a strategy.

But risk management is the product.

For years, investors chased growth.

Now many are rediscovering income.

Private credit offers:
𝗖𝗼𝗻𝘁𝗿𝗮𝗰𝘁𝘂𝗮𝗹 𝗰𝗮𝘀𝗵 𝗳𝗹𝗼𝘄
S𝗵𝗼𝗿𝘁𝗲𝗿 𝗱𝘂𝗿𝗮𝘁𝗶𝗼𝗻
L𝗲𝘀𝘀 𝗰𝗼𝗿𝗿𝗲𝗹𝗮𝘁𝗶𝗼𝗻 𝘁𝗼 𝗽𝘂𝗯𝗹𝗶𝗰 𝗺𝗮𝗿𝗸𝗲𝘁𝘀

In uncertain environments, income becomes the anchor.

A strategy we think about often:

	One side: stable income and downside protection.
	The other: long term growth and asymmetric upside.

Not everything should be aggressive.

Not everything should be conservative.

Balance is the edge.

When I first started thinking seriously about investing, it was not about charts, returns, or financial strategies.

It was about time.

I remember realizing that most of us are taught to trade our time for money.

Work the hours. Earn the paycheck. Repeat next week. Repeat next year.

There is nothing wrong with hard work. In fact, it is where most wealth journeys begin.

But at some point a question shows up:

What happens when you want your time back?

That is where investing changes the conversation.

Every dollar invested is a small worker you hire.

One that can go out and produce income without needing your hours attached to it.

At first the impact feels small.

A little income here. A small distribution there.

But over time something powerful starts to happen.

Those investments begin funding things your job used to fund.
Family trips.
Flexibility in your schedule.
Opportunities you would have once had to say no to.

Eventually the goal shifts again.

It is no longer just about buying back your own time.

It becomes about creating a foundation your family can build on.
Investing becomes legacy.
Assets that produce income.
Businesses that continue operating.
Real estate that increases in value.

You start thinking not just about the next year, but the next generation.

Wealth is not built overnight. It is built decision by decision, investment by investment.

But the most meaningful part is not the numbers.
It is the freedom those numbers create for the people you care about most.

That is when investing stops being about money.

And starts being about life.

Some of the strongest returns in private markets come from backing operators, not tickers.

Entrepreneur funds focus on acquiring and scaling real businesses, often in essential industries.

These are companies with customers, cash flow, and leadership teams already in place.

What makes them compelling is not speculation. It is execution.

Entrepreneur funds can provide:
	&gt; Cash flow as businesses mature
	&gt; Equity growth through operational improvement
	&gt; Asymmetric upside through consolidation and scale

In a balanced portfolio, these funds often sit in the growth and upside bucket.

They complement income-producing assets and add exposure to value creation that public markets cannot replicate.

You are not betting on headlines.
You are partnering with people building real businesses.

Tax mitigation is not just for the ultra wealthy.

It is for anyone serious about compounding.

Real estate depreciation.
Oil and gas deductions.
Business ownership credits.

These are incentives built into the system.

Less tax drag means more capital staying invested.

That is how wealth compounds faster.

A few years ago I drove through the middle of the country and stopped in a town most people would never notice from the highway.

It looked quiet at first. A few warehouses, rail lines running along the edge of town, trucks moving in and out of loading bays. Nothing flashy.

But when you start paying attention, you realize places like this are the backbone of the economy.

Inside those buildings were distributors moving parts to manufacturers. Food suppliers shipping to grocery chains. Equipment suppliers sending materials to construction crews hundreds of miles away.

That one industrial corridor quietly connected farmers, factories, retailers, and consumers across multiple states.

This is why centrally located industrial development can be such a powerful investment.

When a warehouse sits in the middle of a major transportation network, it becomes more than just a building. It becomes infrastructure.

Products move faster. Shipping costs drop. Supply chains become more reliable. Local jobs are created. Small businesses gain access to national markets.

And because the demand for logistics space continues to grow while supply in key corridors remains limited, these assets tend to benefit from durable long term fundamentals.

Industrial development is not always exciting to look at.

But it plays a critical role in keeping the American economy moving.

Sometimes the best investments are not the ones everyone is talking about.

They are the ones quietly serving the country every single day.

When people hear “growth investing,” they often think about startups and new technology.

But one of the most durable growth strategies looks very different.

Buying profitable small businesses.

Across the country there are thousands of companies with real revenue, real customers, and proven business models.

With the right capital and leadership, these businesses can grow significantly through:
• Operational improvements
• Better systems and management
• Strategic acquisitions
• Expanded markets or services

Investors are not betting on an idea.

They are investing in businesses that already generate cash flow and then helping them scale.

In many ways, it is one of the most straightforward paths to value creation in private markets.

✔️ Find a great business.
✔️ Add the right operators.
✔️ Make it better.

Liquidity is one of the most misunderstood concepts in investing.

Many investors focus on how quickly they can sell an asset rather than how their portfolio generates cash flow.

Income funds like Kudo are designed to provide ongoing monthly distributions, while land funds prioritize long-term appreciation with minimal operational complexity.

Each serves a different purpose, and both can coexist in a well-designed portfolio.

If you want help thinking through liquidity beyond “buy and sell,” I am happy to review it with you.

Appreciation is great.

Cash flow is freedom.

Income producing investments create optionality:
	• Reinvest
	• Diversify
	• Reduce reliance on a paycheck
	• Stay patient through volatility

That is why we focus so heavily on private credit and real assets.

Compounding works best when cash flow fuels it.

The Health Advocate: Health Insurance Consulting Services

I specialize in helping high-income self-employed individuals and small businesses reduce health insurance costs without sacrificing coverage quality.

✅ Private plans (not income-based)
✅ 20–30% lower premiums
✅ Nationwide PPO networks
✅ Ideal for healthy individuals/families

If you're self-employed and overpaying — I’ll help you fix that. Fast.

➤ DM me or visit https://calendly.com/thehealthadvocate

Health Insurance Consultant

Owner

1st Gen Entrepreneurs

Member

Helping Entrepreneurs Uncover Their Health Insurance Options and Find Coverage They Need Right Now | Long Term Problem Solver | Decipherer of Boring Insurance jargon

If you’re self-employed, healthy, and earning a high income — your health insurance is probably costing you too much.

Most of my clients come to me paying inflated ACA/Marketplace premiums because their income disqualifies them from subsidies. Sound familiar?

I help entrepreneurs, freelancers, and small business owners switch to private network plans that:

Aren’t based on your income

Travel nationwide

Often save you 20–30% monthly in premiums

And give you the PPO network coverage everyone always wants

I do all the research, simplify the jargon, and guide you to a smarter, more sustainable solution — without sacrificing quality of care.

Check out my website to see if we're a good fit -> https://thehealthadvocate.co/

💬 Or just DM me “Insurance” and I’ll send the details.

Mitchell Underwood

Now this is really something 

Two different connection requests
6 hours apart

Exactly the same message 🤦‍♂️

Also, anyone else ever been told they have warrior blood by a complete stranger before?

I’m not a LinkedIn guru or anything but I feel like thats a bit much 

Filing this under “What in the automated hell” category

Anyone else seen this before?

Helping High-Income Self-Employed Save 20–40% on Health Insurance | Private Plans | No Income-Based Pricing | Nationwide Coverage

75 hard enthusiasts, sober living folks, etc I respect the hell out of yall, but you can skip this post 


Anyone else thinking they might crack a beer tomorrow morning for this one? 😂👀

USA vs Canada for the Gold Medal in Hockey

7 am cst. Unreal start time for such a huge game but they are playing in Milan, so 🤷🏻‍♂️

Canada boasts probably the two best players in the world in Connor McDavid and Nathan Mackinnon + maybe the most talented team overall we’ve ever seen

Yet, they’ve struggled their last two games and have come pretty close to losing

Which gives me hope the USA can pull this thing off 

If you saw their match up last year at the Four Nations, you know this game will be incredibly intense. Pic below for reference.

That said, beer or no beer, who ya got!?

I got the US winning 4-3, game winning goal scored by Brock Nelson of the one and only Colorado Avalanche

Last week, a prospect I’d spent weeks helping texted me out of nowhere.

“No thanks. Going another direction.”
 
Wouldn’t take my call.  
Wouldn’t share why.  
After nothing but good conversations and zero objections.
 
Totally blindsided me, as there was zero hint of any concerns, dissatisfaction, or uncertainty

And to be honest, this one hurt for some reason. I've developed a thick skin over the years but this one actually struck a nerve. 
 
→ Fast forward to this week.
 
A small business owner who was about to get crushed by a brutal group renewal expressed how incredibly grateful he was for my help, saying that with my help, they had dodged a bullet after I was able to restructure their benefits package and save them over 3k a month in premiums

Same job.  Same effort.  Very different outcomes.
 
That’s the self-employed world.
 
One day you’re feeling frustrated and defeated, questioning what you did wrong

The next you’re reminded of exactly why you do what you do.
 
IYKYK

Friendly reminder: you can make an impact here by simply “liking” someone’s post

Sometimes a connection of yours sees that in their feed

And it leads them to someone whose help they’ve actually been looking for 

I know because it happened to me this week

All because one of you “liked” a post of mine 

So, even if you don’t have time to comment

If you see a post that resonates, someone whose work you support - drop a like or react

Not to be nice or to give them an ego boost 

But because it just might actually get them a client

2 ways self-employed people get blindsided by rising health insurance costs and how to avoid it
 
If you’re self-employed, your income isn’t static.
 
And that’s exactly where problems start.
 
 
1️⃣  Success can make your premiums explode
 
Year 1 in business?  Maybe you qualified for a large ACA tax credit.
 
Your family’s premium might have been:  
→ $0  
→ $100/month  
→ Very affordable
 
But Year 2?
 
Revenue grows.  
You update your projected income.  
The subsidy shrinks.... or disappears entirely.
 
And suddenly…
 
That $100/month plan becomes $1,300/month.
 
I’ve seen it happen.
 
Because ACA subsidies are income-based, the more you make, the less help you get. If you cross certain thresholds, you’re paying full price and that price isn’t small.
 
𝗛𝗼𝘄 𝘁𝗼 𝗮𝘃𝗼𝗶𝗱 𝗴𝗲𝘁𝘁𝗶𝗻𝗴 𝗰𝗿𝘂𝘀𝗵𝗲𝗱 𝗯𝘆 𝘁𝗵𝗲 𝗶𝗻𝗰𝗿𝗲𝗮𝘀𝗲:
 
If you don’t qualify for subsidies (or won’t next year), it may be time to evaluate private PPO options outside the Marketplace.
 
For healthy families without pre-existing conditions, private coverage can often run 20–30% less than an unsubsidized ACA plan - sometimes with better networks and lower deductibles.
 
The key is being proactive before your renewal hits.
 
 
2️⃣ Auto-renew can create a tax bomb
 
This one is sneaky.
 
If your Marketplace plan auto-renews and you don’t update your income, the system may use last year’s income projection.
 
If you made significantly more this year but kept receiving advance premium tax credits…
 
You could owe that money back.
 
All of it.
 
I’ve seen five-figure repayment bills.
 
Imagine thinking your coverage was “cheap” all year…  Only to get hit with a $15,000–$20,000 tax bill because you unknowingly took subsidies you didn’t qualify for.
 
𝗛𝗼𝘄 𝘁𝗼 𝗮𝘃𝗼𝗶𝗱 𝘁𝗵𝗶𝘀:
 
→ Always update your income projection with the Marketplace  
→ Don’t assume auto-renew means “everything is handled”  
→ Recalculate what your real premium should be  
→ If the updated premium is no longer affordable, explore alternatives
 
 
The bottom line:
 
When you’re self-employed, your health insurance costs are directly tied to your income decisions.
 
And your success could come with a lot of unforeseen costs if you aren't prepared or know how to navigate the health insurance landscape

If your income is growing or you feel you're definitely underpaying based on what you're bringing in each month, it’s worth reviewing your situation before tax season does it for you.
 
Because the worst surprises in this industry don’t happen during enrollment.
 
They happen when you file your taxes.

Texting a prospect and my phone just auto corrected “take you through the application” to “take you through the apocalypse” 

Which is kind of fitting for our healthcare system, to be fair 😂😂😂

So yeah, dont go through it alone, work with a pro - Ive seen it all 

That’s all I got today, stay safe out there yall ✌️

“I figured it would be like $500-$600 a month. $1300? WTF”

Sadly, many who leave their employer under estimate the cost of health insurance and end up feeling like this 

Stunned. Shocked. 
Highly annoyed - to put it lightly

They didn’t realize just how much their employer was subsidizing the cost of their plan

Until they saw their COBRA rate or shopped their Marketplace options 

And got gut punched by reality

Which is exactly why I recommend speaking to someone about your situation BEFORE you put in your two weeks and decide to make that leap


—> Yet, it always depends. This isn’t always the case

Because for every person that’s been hit with sticker shock

There are just as many I’ve encountered that are pleasantly surprised 

Who thought their family plan could be 2k/month and are perfectly ok with $900-$1200

Or even better - a family planning for a low income first year in business finding out they qualify for a tax credit to bring down the cost of their premium dramatically…from a few hundred a month to even $0/month

—> How to know where you’ll land? Or what the best fit is?

You could google it for a while and get some idea, poke around in the dirt, maybe make some mistakes

Or you can get straight to the point and send me a DM. 

There are many different variables to consider(Health, income, age, timing, qualifying events, etc) and I can help you make sense of all of it, quick

And get straight to the point 

During 1 short conversation 

“Based on what you’ve told me, this is what you can expect. These are what types of options you can explore. This is around what they will cost” 

Vs trying to figure it out on your own. 

Or worse, pulling the trigger without knowing and getting gut punched with surprises. 

If you have any questions, send me a DM.

You woke up without a job... not because you lost it, but because you bet on yourself.
 
You open your eyes.
 
6:00 AM.
 
For a split second, your body expects the old routine. The alarm. The rush. The commute. The meetings.
 
But then you remember…
 
You don’t have to be anywhere.
 
No boss.  No clock-in time.  No one watching.
 
You lie there for a minute longer than usual.  Freedom feels good.
 
And then it hits you.
 
Your paycheck isn’t guaranteed anymore either. 
 
No direct deposit every two weeks.  No HR department.  No employer-sponsored health plan quietly covering you in the background.
 
That coverage? It ends at the end of the month.
 
And now it’s on you.
 
This is the part no one talks about when you go self-employed.
 
You prepare for revenue swings.  You prepare to sell.  You prepare to market yourself.
 
But most people don’t prepare for navigating health insurance alone.
 
You quickly realize:
 
→ The plan you had through work was heavily subsidized  
→ The marketplace premiums are higher than you expected  
→ The networks look… different  
→ And suddenly you’re responsible for protecting your income, your health, and your family
 
This is where excitement can quietly turn into stress. 

And many people come to me this way, worried and unsure of what's next when it comes to health coverage, almost second guessing if they put the cart before the horse. 

HMO? PPO? EPO?
Premium Tax Credits?
Projected household income? Based on what? 

So many of these questions and more flood your brain the moment you actually start to look and to be frank, it is absolutely overwhelming. 

But I don't believe that being self employed should mean settling for confusing, overpriced coverage or crossing your fingers and hoping nothing happens.
 
It just means the strategy changes.
 
And that’s where I come in.
 
You bet on yourself.
 
Now let’s make sure you’re protected like someone who did. 

Send a DM if you're tired of dealing with this monkey business alone and just want good, affordable coverage that you can actually understand for once.

taplio

The Battle

Dylan Reach

Mitchell Underwood

Followers

Posts

Engagements

Likes

Performance ScoreDylan Reach's LinkedIn Performance

Performance ScoreMitchell Underwood's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Dylan Reach

Mitchell Underwood

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Dylan Reach's LinkedIn Performance

Performance ScoreMitchell Underwood's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreDylan Reach's LinkedIn Performance