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

If you:
- Don’t carry credit card debt
- Have an emergency fund
- Contribute to your 401(k) at least up to the match
- Max your Roth every year
- Consistently have a monthly surplus

You’re already ahead of a huge percentage of people

Even if it doesn’t always feel like it.

This is the foundation most people never fully build

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

Financial planning can be so fun. Right now am working on a plan for a retired client of mine who is worth above $25mil

Talking:
- Roth conversions (paired with a DAF contribution to offset it) 
- Asset location (parking higher growth assets in Roth and fixed income in pre-tax)
- GRATS to get more out to their kids without using any exemption
- QCD's for when they get there 
- Irrevocable trust planning since they are very young and close to the $30mil already 
- private equity investments
- lots of capital gains and income tax planning

The value for these types of clients is unreal 

You should have a great, coordinated team at this net worth level

Once you have a child, your financial life changes immediately

It’s no longer just about you. It’s about protecting someone who depends on you for everything.

Here are four things you need to address right away:

1. Estate planning documents
You need clarity around guardianship, who makes medical decisions, and who handles finances if something happens to you. Without this, the courts decide for you.

2. Life insurance
If your income supports your family, life insurance isn’t optional. It’s how you replace income and protect your child’s lifestyle if you’re not there. And you might want it on your stay at home spouse too. Work coverage is not enough 

3. A larger emergency fund
Kids bring higher expenses and more unknowns. A bigger cash buffer gives you flexibility when life throws surprises at you.

4. Add them to your health insurance plan
Medical costs add up fast. Make sure coverage is in place from day one. You do not want to miss the 31 day window 

Having a child isn’t just a life milestone, it’s a financial planning checkpoint

In most cases, filing jointly for taxes has made sense

But sometimes, separately can be more beneficial:
- under $500k income each and making similar amounts could mean double SALT exemption or more 
- Student loan forgiveness 
- One being able to pick up QBID in their business if separate 
- one is lower income and has a ton of medical expenses that they could deduct 

Any others you guys can think of?

20 tax planning moves W-2 earners can make to lower their tax bills (this year and or in the future)

1) Max out your 401k, 403b, 457, etc
2) Max out your Roth IRA (you have until the tax filing deadline on this one)
3) Max out your HSA
4) Max out your 529 plan to the state tax benefit
5) Use all of your dependent care FSA funds
6) Use FSA funds as most are use it or lose it
7) Do tax loss harvesting on your taxable investment accounts
8) Do some tax gain harvesting within your taxable investment accounts
9) Consider electing into your ESPP for next year
10) Sell ESPP funds that became yours in December (if you want to lock in the discount)
11) Do Roth conversions to maximize lower tax brackets
12) Exercise ISO’s up to the AMT threshold (or maybe even past if it’s part of your plan)
13) Exercise NSO’s if it makes sense
14) Look through your paycheck and make sure you have withheld enough for taxes
15) Do mega-backdoor Roth if your company allows it and you have extra money
16) Donate cash to charity (maybe even consider bunching/donor advised fund to get even more in deductions)
17) Donate highly appreciated securities (before selling to avoid the capital gains tax)
18) Do a cost segregation study on your property and bonus depreciate it while bonus is still at 80%
19) Invest in a qualified opportunity zone if you have a large capital gain to defer
20) Prepay property taxes to hit max deduction

Roth vs. Traditional 401(k)

Which should you use

Like most finance questions...it depends

Here’s a quick breakdown:

Roth 401(k):

No tax deduction now

No required minimum distributions (RMDs)

Withdrawals are tax-free in retirement

Investments grow tax free

Traditional 401(k):

Contributions reduce taxable income now

Subject to RMDs

Withdrawals taxed as ordinary income

Roth makes sense when you think you are in a lower bracket today than the future (Retirement, Roth conversions, etc)

Traditional makes sense when you think you are in a higher bracket today than the future

Both can be and are right at different times in life for high earners

Taxes will be your #1 expense over your lifetime

But as business owners, you have a unique advantage when it comes to taxes

You have the power to strategically lower your tax bill

The difference can be $100,000+ in tax savings

Here are 12 strategies you can take advantage of:

The more you save on tax, the more you can be paid, and the better your business can grow. So what are some of the best tax planning moves to consider

Open article: 12 Tax Planning Moves for Business Owners by Thomas Kopelman • 6 min read

12 Tax Planning Moves for Business Owners

One of the best way to reduce tax for high earners is through real estate:
- ST rentals: hitting material participation tests
- LT rentals: spouse gets REPS status 
- Business owner: owns the real estate they operate in

All can allow you to do cost seg studies, bonus depreciate the property, then use those losses to offset active income

But this is not something you DIY

You need to hit the participation tests and log your hours for the top 2 or the losses are simply passive

And you need to file correctly

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