Matt Matros

Founder

Founder with 3 exits in B2C now playing two hands in B2B (insurance and commercial janitorial). | I post daily lessons & learnings that are your shortcuts.

Founder with two 8-figure exits plus an ‘acqui-hire’. My lessons & learnings are your shortcut.

Currently acquiring small businesses across America, across industries.

My inspirations are Scott Galloway and Fareed Zakaria and The Economist. 

I aspire to be the “Rick Rubin for entrepreneurs.”

These opinions are purely my own and not of any of the companies I am affiliated with.

Founder and General Partner

NCC is micro private equity providing capital and support to owner/operators in the commercial cleaning & janitorial industry.

Top 100 Advisor By Investopedia. Helping 30-50 year old Business Owners and Those With Equity Comp Build Wealth 💰. Co-Founder & Financial Planner at AllStreet Wealth. Head of Community at Wealth.com

Hey there!

My name is Thomas Kopelman. I am the Co-Founder of AllStreet Wealth, a financial planning firm for very high income 30-50 year old entrepreneurs and those with equity comp. I am also a:

- Blogger (thomaskopelman.com)
- Content Creator (podcast: The Long Game Podcast)
- Entrepreneur (Own AllStreet Academy and AllStreet Wealth)
- Top 100 Advisor By Investopedia in 2022 and 2023
- 2023 Young Advisor To Watch
- Top 23 Millennial Financial Advisor by Business Insider

For way too long, this age demographic has been neglected by the financial services industry. There are a large number of high income earners in my generation that are craving good, quality financial planning. That is what we are here for.

Let’s face it, life in your 20’s, 30’s, and 40’s can be hard. You have Multiple jobs, student loans, marriage, kids, a new 🏡 , starting a business, paying for education for your kids, etc. Juggling all of that is enough let alone figuring out how to accomplish it financially. You don’t have the time nor do you want to have to learn about taxes, investing, equity compensation, estate planning, the best accounts to use, etc. Your time is best spent doing what you love!

That is why I am here, to help you figure out how to use your resources to live the life you want. Isn't that the goal? To live the life you have dreamed of?

At AllStreet Wealth, we help our clients move beyond the surface level goals they think they want and determine the lives they truly want to live. Our goal is to help our clients live fulfilled lives by identifying what is enough, building a plan that takes them in this direction, and keeping them on track when things change.

We meet our clients where they are in life and show them the intersection between 'personal' and 'finance' so they can ultimately live the life they want.

If you want to learn more:

https://www.allstreetwealth.com/thomas

Thomas Kopelman

The second people try to negotiate my fees or say it should be cheaper for them cause “they’ll require less work”

We pass on working with them 

They’re never less work

They always end up being the most work

And end up being the hardest to work with 

My goal is to max out at 125-150 clients that love working with us and value us

We are about 80% of the way there right now

Financial Planner Helping 30-50 year old Business Owners and Those With Equity Comp Build Wealth 💰. Co-Founder at AllStreet Wealth. Head of Community at Wealth.com

8 years ago, I had a business planning workshop with my first company

My goal I wrote down…by 30 to have 100 clients and to be making $100k a year

I thought this would be really hard to hit

Fast forward to today…. We are at $150k a month of revenue and a run rate of $1.8mil with a little over 100 high income/high net worth households 

And We get to work with some of most amazing, hard working, and successful people out there

What a wild ride it’s been and it’s only year 4! 

Building AllStreet Wealth has been one of the most fun and rewarding things I’ve done

Most people know about asset allocation…
 
But very few understand asset location 

This is where tax savings get real

Getting asset location right can save 6–7 figures over a lifetime for high-income investors

What it looks like in practice
- Roth accounts: highest-growth assets go here. No bonds. No low-growth holdings that could be taxed elsewhere

- Pre-tax accounts: assets with higher tax drag. Taxable bonds, REITs, high-dividend investments. Anything that would be inefficient in a taxable account.

- Taxable accounts: most tax-efficient assets. ETFs, low-dividend stocks, municipal bonds. Investments designed to minimize taxes each year.

Why it matters
- Many investors focus on picking funds, but where you hold them often matters more than what you pick.
- A smart asset location strategy can compound tax savings exponentially over decades

A lot of financial advisors believe personal finance is black and white

I don’t at all

I have some non traditional views that a lot wouldn’t agree 

Here’s some examples:
- I believe in bitcoin and allocate a good percentage of my income there. Many of my clients do as well. But also don’t push it. It’s a personal choice. Most either hate it or they think you should allocate everything to it. I think both are wrong. 
- I believe you can have 10-20% of your portfolio outside of ETFs and index funds invested in things you enjoy and find interesting 
- cars are great. You can spend a lot of money on a car and take on a car loan if it fits your budget 
- the goal isn’t to spend as little as possible. It’s to spend as much as you can on things you love while still investing enough for the future 
- I think concentration is fine. Most say you shouldn’t have more than 10% in any Single thing. Many of my clients have 10-50% in their company stock, their business, a few investments, etc but they do all the right things to allow that to work 
- credit cards a great tool and should be used 
- budgeting isn’t needed for high income folks. They just need to understand average surplus and if that’s enough for their goals

I will say, a lot of this is due to working with a specific group that has more income

It creates more room for nuance

Running a business can be one of the most powerful wealth building and tax planning tools available

But only if you do it right 

I see the same early mistakes over and over, even from very successful business owners

If you want to set yourself up correctly from Day 1 (or fix it before it gets expensive), here’s what matters most 👇

1. Get your entity election right

This is foundational.

The right structure can dramatically reduce taxes and expand planning opportunities

The wrong one can mean:
- Unnecessary self-employment taxes
- No access to PTET
- Reduced or eliminated QBID
- Limited retirement contribution options
- No QSBS
- Less tax efficient for reinvesting and growing the business 

This decision should be proactive and can change as your business evolves

2. Keep business and personal finances completely separate

Commingling accounts is one of the most common  and costly mistakes

It can:
- Create audit risk
- Destroy LLC liability protection
- Turn tax prep into a nightmare
- Cost you far more in professional fees and your time 

Clean separation from Day 1 saves money, time, and stress.

3. Track all your expenses 

Most business owners leave money on the table simply because they don’t track well

Good tracking:
- Maximizes legitimate deductions
- Makes tax planning actually work
- Gives you clarity on real cash flow

The easiest time to do this is before the business gets “busy.” 

4. Save for taxes monthly

This is non-negotiable

I see too many high-income business owners fall behind, then have to scramble to make things work 

Treat taxes like a fixed expense, not a surprise

This is a huge reason we give clients new tax updates at every call 

5. Understand safe harbor taxes and pay your estimates

Underpayment penalties are completely avoidable.

You need to Know:
- Your safe harbor number
- Your quarterly payment schedule
- What you will get in from withholding
- How income volatility affects estimates

If you don’t know these numbers, you’re guessing

And guessing is expensive

6. Do real tax planning 2–3x per year (not just in April)

One of the biggest advantages of business ownership is tax flexibility

But it only works if you plan:
- Mid-year
- Again in Q3
- Then finalize in December

Tax planning is proactive. Tax prep is reactive

7. Setup the right retirement accounts

Set up the right retirement accounts

Not all retirement plans are created equal.

In most cases:
- Solo 401(k) > SEP IRA
- 401(k) > SEP IRA and Simple's 

The wrong setup can cost you tens of thousands per year in missed contributions 

And limit Roth strategies

Owning a business gives you incredible leverage... if it’s structured correctly

But I see so many overpaying in taxes because they do not invest in tax planning

Buying a house today that stretches your budget, hoping to refinance in a few years… is a risky bet

Sure, it might work out.

But what if it doesn’t?

Interest rates could stay high for years.

Unexpected expenses, market changes, or life events could make that “stretch” unbearable.

The smarter approach
- Buy what’s affordable today
- Leave room in your budget for emergencies, lifestyle, and wealth-building
- Avoid relying on “hope” as part of your plan

I’ve worked with many clients who bought more house than they could comfortably afford.

All it led to was stress and regret

I can tell you one thing, those with a financial plan are way less worried during market down turns now than those without

When you align your investments, with your goals and time frame

And you stress test your plan, it’s easier to get through it

Not easy… but easier

When does an S Corp actually make sense?

Despite what social media says, an S Corp is not a default move for every business owner

Here’s how I generally frame it for clients 👇

➡️ Under ~$100k of profit

An S Corp rarely makes sense. The added:
- Payroll costs
- Compliance
- Accounting fees
- Administrative burden
- Reasonable comp requirement 
- Reduced QBID

Often outweigh any potential tax savings from SE taxes

➡️ $100k–$200k of profit

Now it becomes a real consideration

At this level, the math can start to work

But only if:
- A reasonable salary is properly established
- Retirement contributions are modeled correctly
- QBID is factored in
- State taxes (and PTET eligibility) are included

This is where typical “rules of thumb” break down and real analysis matters

➡️ $200k+ of profit

The benefits often become meaningful

Now you might see:
- Material savings on self-employment taxes
- Better retirement plan optimization
- More flexibility in overall tax strategy

But only if the structure is done correctly

➡️ $500k+ of profit

For non-SSTB businesses, an S Corp can be critical to:
- Preserve or maximize QBID
- Control taxable income more intentionally
- Layer in advanced state and retirement strategies

At this level, not structuring correctly can be very expensive

We see a lot of folks come into working with us above the $500k level that are getting $0 in QBID because they are not an S Corp

One of the biggest allocation mistakes I see:

People early on rushing to invest in private investments

Private investments absolutely have a place.

But for most people, that place comes much later than they think.

Before private investments, you want to:
- Fully use tax-advantaged accounts (401(k), Roth, HSA, Mega Backdoor Roth 401(k), etc.)
- Build meaningful liquidity in a taxable account

Establish flexibility for:
- Opportunities
- Emergencies
- Life changes

Liquidity gives you options

Illiquidity takes them away.

Private investments are often:
- Illiquid for years
- Hard to value
- Difficult to exit
- Riskier than advertised

This is totally fine when the rest of your financial foundation solid

It’s dangerous when it’s not

And For business owners specifically, your business already is a private investment

Early on, most of your Net worth, Cash flow and risk is tied to a single, illiquid asset

Layering on more illiquidity too early only increases risk

You want to be smart here

AllStreet is currently at ~90% capacity

Each January, we’re intentional about onboarding a limited number of clients we plan to work with in the first half of the year

The first year working together is the most intensive

We typically meet 6-8 times to fully understand your financial life, goals, business or equity compensation, tax situation, and risks

From there, we build a comprehensive plan and help implement everything

After that, we become your long-term financial partner

Our goal is simple…

✅ Be proactive every year & be available exactly when you need us

Here's a quick breakdown of what it looks like to work with us in 2026:

Happy 2026 everyone, I hope you had a wonderful holiday season and were able to spend meaningful time with family. I was fortunate to spend most of th

Open article: A Look Inside AllStreet Wealth by Thomas Kopelman • 3 min read

The best tax strategies don't just reduce taxes this year

Sometimes, it is best to INCREASE taxes this year

I know, it sounds wrong, but it’s usually a sign you’re thinking long-term

Examples I see all the time 👇
- Choosing Roth contributions when it makes sense
- Executing Roth conversions intentionally
- Locking in capital gains at favorable rates
- Structuring as a C Corp to qualify for QSBS

Paying tax today to create flexibility later can be a great move

Good tax planning isn’t about minimizing this year’s return

It’s about:
- Reducing lifetime tax exposure
- Creating future flexibility
- Avoiding forced distributions at high rates
- Controlling when and how you pay taxes

The most successful people I know have no problem spending money to make sure things are done well

They understand something many don’t:

Time is the most valuable asset they have.

Instead of trying to do everything themselves, they:
-Hire top-tier professionals
-Delegate aggressively
-Remove friction from their lives
- Focus their time on the work only they can do

This isn’t about being careless with money

It’s about being intentional with it.

They know that:
- A great advisor prevents costly mistakes
- A strong team creates leverage
- Buying back time often has the highest ROI

The goal isn’t to spend less

It’s to spend better, in ways that compound

That mindset is a major reason they continue to win

Diving into social media 7 years ago was one of the best decisions I’ve made for my business.

It helped me grow AllStreet Wealth  from $0 to $1.5M in revenue in about 4 years (2025 numbers).

Now, I have ~30 advisors every week asking to meet, pick my brain, and learn how to use social media to grow their firms.

Because of that, Rachael Camp, CFP®, Treyton DeVore , and I built a social media course specifically for financial advisors — showing you exactly how to get started and build a sustainable content system.

✔️ 3+ hours of practical, step-by-step training
✔️ Built for real advisors with real practices
✔️ Already used by 100+ advisors in the last year
We’re offering 33% off to kick off the year.
Use code NEWYEAR before it expires

The link to buy is in the tweet below

No alternative text description for this image

I'm a financial planner that works with the wealthiest 1% of people in their 30s and 40s

I've learned that personal finance, investing, taxes, etc. is made out to be way more complicated than it should be

My role is to simplify it and help people accomplish their goals

So this week, I want to share 10 critical lessons I wish everyone understood about money:

1) Your income is your most important resource People spend so much time talking about budgeting and lowering your expenses. And I get it, this can be

Open article: 10 Critical Money Lessons Everyone Should Know by Thomas Kopelman • 6 min read

10 Critical Money Lessons Everyone Should Know

Equity compensation can be an incredible wealth builder…
 
Or a tax disaster if you don’t understand how to manage them

Here’s a high-level breakdown of the most common forms I see with executives and high earners 👇

1. RSUs (Restricted Stock Units)

They are taxed as ordinary income on the vest date

Most companies withhold a flat amount (often 22% or 37%), which can be very wrong

You need to understand that taxes are due immediately, whether you sell or not

Key question to ask on buying vs selling decision:

If someone handed you that amount of cash today, would you buy this stock?

If the answer is no, holding the RSUs probably isn’t the right move.

And remember, your future RSUs have the price changes built into them

2. ISOs (Incentive Stock Options)

No regular income tax on exercise, but you have to worry about AMT

AMT can be triggered, creating a surprise tax bill for many

This is why early exercising before the stock has grown much can be powerful 
but only with proper AMT modeling

The risk:
- You can pay tax on paper gains for stock that Never becomes liquid
- It Declines in value
- Or never has a successful exit

This requires real planning, not guesswork

3. NSOs (Non-Qualified Stock Options)

Taxed as ordinary income at exercise on the spread

Early exercising can reduce income taxes

But it also means paying tax before certainty exists

The risk... Paying income tax on something that ultimately becomes worthless.

Equity compensation is not “free money.”

It’s a series of:
- Tax decisions
- Cash flow decisions
- Concentration risk decisions

What works for one person can be completely wrong for another

“We’re moving. Should we turn our primary home into a rental or sell it?”

This is one of the most common (and most misunderstood) questions I get

And the real answer is: it depends..

But not in a vague way where we're trying to avoid answering the question

It depends in a numbers & strategy way

Here are the key variables that actually matter 👇

1. Your broader real estate plan

- Do you already own rentals?
- Do you plan to build a portfolio, or is this a one-off decision?

Accidental landlords often underestimate the complexity and capital required

2. Rental economics

You need to look at:
- Realistic market rent
- Ongoing maintenance
- Property management (even if you self-manage, your time has a cost)
- Vacancy risk

If the numbers don’t work cleanly, emotion shouldn’t override math

3. Equity and the capital gains exclusion

Up to $500k (married) of capital gains may be excluded if you qualify

Turning it into a rental can reduce or eliminate this benefit later

Once that window closes, the tax cost can be very real and it is hard to recapture anytime soon 

4. Your capital gains tax bracket

- Federal
- State
- Net investment income tax

This materially impacts the true cost of selling versus holding

5. Funding your next home

- Do you need this equity for the next down payment?
- Would selling reduce leverage and stress in the next purchase?

Liquidity matters more than most people realize

6. Future real estate plans

If you plan to buy more rentals:
- Selling may provide cleaner capital
- It may allow better asset selection
- It can improve diversification

Keeping a property simply because you already own it isn’t a strategy..

This decision isn’t about: “Is real estate the right move?”

It’s about: “Is this specific property the right use of capital given your goals, taxes, and risk tolerance?”

Doing the Backdoor Roth IRA every year for you and your spouse can be a small step with a huge long-term impact

$7,500 per person per year may sound small, but it can grow to millions of tax-free dollars when you have a long time horizon of 20–50 years

The issue with backdoor Roths is that many people make mistakes when executing it 

Here are a few common mistakes to avoid:
- Having other pre-tax IRA funds: triggers the pro-rata rule and could create unexpected taxes
- Not converting after contributing: growth is taxed if left in the IRA
- Failing to invest after converting: account type ≠ investment
- Not filing Form 8606: you must track basis to avoid double taxation
- Reporting conversions incorrectly: can result in paying more taxes than necessary

Short term planning is where I see people make some of their biggest mistakes

In today's new episode, Benjamin Lake, CFA, CFP® and I break down:

• Why investing short term money can backfire
• Where cash actually belongs when you need it in the next 1-3 years
• Pros & cons of high yield savings, money markets, munis, and treasuries

Listen on Apple or Spotify

Tax loss harvesting can be a massive value add for high-income investors

If you’re like most of my clients, your capital gains are being taxed at 23.8%- 37% depending on the state you are in:
- 20% long-term capital gains rate
- 3.8% net investment income tax
- 4–13.3% state taxes, depending on where you live

That means every $100,000 of gains you offset with harvested losses can save $23,800–$37,000 in taxes

This is huge

Tax loss harvesting is particularly impactful for those who:
- Have a liquidity event coming from a business sale like many of my clients 
- Need to diversify from concentrated equity compensation
- Hold older investments with very low cost basis

You can do this with stocks and ETFs

But there are also some tools that make this easier:
- Direct indexing
- Long/short direct indexing
- Boxx spread loans (comes through as capital losses)

These allow for more precise harvesting, more losses, and keeping your portfolio aligned while capturing tax benefits along the way

If you welcomed a child in 2025 (like me), then you need to know about the new Trump Accounts

They’re government-created, tax-advantaged investment accounts opened in a child’s name

You can put funds in after-tax that grow tax-deferred

Then you pay income tax when you take them out in the future

And... for kids born between January 1, 2025, and December 31, 2028, you get an initial $1,000 from the federal government (if you claim it)

Here’s what you need to know about claiming & taking advantage of these new accounts:

To get started, you currently have two options: Option 1 (likely the easiest): Visit trumpaccounts.gov and enter your email. You’ll receive instructio

Open article: New “Trump Accounts” Explained (& How to Claim $1,000) by Thomas Kopelman • 2 min read

New “Trump Accounts” Explained (& How to Claim $1,000)

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The Battle

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