winning the lottery

Holy crap, I won! I never thought in a million years that it was possible! Winning the lottery is now a reality! I’ve always dreamed about this, but I never thought it would happen.

But wait…I need to stay cool. I don’t want to be like all those other lottery winners. I want to be smart. Should I call someone first? Do I need a lawyer? All I know is I want to do good with this newfound wealth. I want to live the life of my dreams and do all the things I could never do before!

OK, honestly, I didn’t win the lottery. But, it sure is fun to think about isn’t it?

We’ve all had our fair share of daydreaming about winning the lottery. While I’m being honest, I don’t even buy lottery tickets. I just use it as an opportunity for me to dream REALLY big.

As I think back, it cracks me up to think about what I would do if I won. I remember specifically thinking that I wanted to buy a little housing village for all of my buddies to live in. We’d each have our own house a court yard to throw parties. It could happen!

We’ve all heard horror stories of how people have blown every penny of their winnings. Many end up much worse than when they were “poor”. You’ve probably heard about winners that have lost their families and their friends. Some have gone into a deep depression and much worse. No matter how much advice is out there, some people just don’t listen.

I’m writing this article for a few reasons. First, I thought it would be fun in light of the recent $1.6 Billion Powerball jackpot. This article will be written as if I actually won!

Second, I’ve worked with a LOT of wealthy individuals throughout my career. I can tell the difference between those that earned their wealth, and those that inherited it. I want to share what goes through their minds when thinking about money.

Last but not least, dreaming big is important. I want to show you some of of the things I think about when I dream about winning the lottery. I have zero expectations of actually winning, but I know that there’s something to this law of attraction stuff.

Plus, did I mention it’s fun?

What I’d Do First After I Win the Lottery

Take my time

I know that being impulsive with my money is always a bad idea. I won’t let myself buy anything until I’ve had the time to think it through. So, you know I won’t be jumping into any quick decisions when it comes to a billion dollars!

In most states, we have up to 3 months to claim our prize. Not that I plan on taking every second of that, but I’m sure not going to jump on Facebook in the first 10 minutes.

I’m going to sleep on it first. I can’t decide if it will be the best night sleep of my life, or if I’ll be up all night giddy as a I was on Christmas Eve.

Stay anonymous

Lottery winners who don’t remain anonymous (because not all states allow it) are immediately circled by the “sharks”. We get enough solicitors at our door as it is.

Unfortunately, for me, that’s not an option. Florida law requires the lottery to provide my name, city and winnings. My phone number and address won’t be revealed, but it’s not hard to find someone’s address if they own their home. Good thing we own our home in a trust! At least that makes it a little harder to find.

So, because I can’t stay completely anonymous, I’m going to take a different route. When I win the lottery, I plan on hiring the best attorney in the area so that I can deposit my winnings into a trust. We’ll get into more details a littler later. The cool part is, I can name the trust whatever I want. It doesn’t have to be, “Brad’s Lottery Winning’s Trust”.

A good example is Louise White of Rhode Island. She named her trust, “The Rainbow Sherbet Trust” because this is what she went to the store to buy the day she bought her ticket.

Now, this doesn’t keep everything a secret. There are many types of trusts that do very different things and I will go over some of those in another post. The point is, I’ll work with my attorney to make sure it’s the RIGHT trust with the right protections in place BEFORE I cash any giant checks.

How I’d Help My Family After I Win the Lottery

I get very nervous about giving anyone a large sum of money. By giving anyone a lump sum of money to “help” them, you can’t be sure they’ll do what you ask them to do. I know a gift should be a gift, but my intentions aren’t so they can buy a great car or blow it on something frivolous. I want to make sure my gift goes to improving their lives.

Say goodbye to mortgages

First, I plan to pay off the mortgages of our closest family members. This money will go directly to the bank. If they pay rent, I’ll pay the year up front and negotiate the amount.

By doing it this way, it’s basically spreading out the gift over many months or years. I would have effectively  given them some breathing room within their budget for additional savings. By doing it this way, I don’t have to worry about being equal or worrying about spoiling anyone.

The amount given to each family member is relative to their existing expenses. If they have additional debt, they still need to pay that down systematically. If anyone chooses to do anything “stupid” with their new monthly surplus, then they’ll have to do so slowly, over time. You can’t blame ME for that!

Now, this would have a potential tax impact down the road. The reason I’m not getting into that just yet, is because I’ve also seen when people operate entirely on preserving or minimizing taxes. I think there is a balance between maximizing your own wealth and truly doing something wonderful that can impact lives. For this specific situation, I choose to help my family. We’ll get into tax efficient gifting strategies later on.

No more medical or education expenses

This is another way I want to help my family. I want to take care of the basics first. We’ve covered shelter, now let’s talk about healthcare.

Much like our social welfare programs, I want to make sure the money goes to the appropriate expenses, not HOPE that they do it themselves. An example of this is food stamps, subsidized healthcare and low-income housing.

There is also a tax play here. This is part of a well thought out gifting strategy.

We can only gift so much to any given person within a given year, before it starts to chip away at our lifetime gift tax exemption. To put it simply, in 2018, a couple can give away a total of about $11.2 Million over their lifetime before they start paying gift tax. This amount changes with the tax laws and goes up each year with inflation.

By giving DIRECTLY to a medical institution or DIRECTLY to a school (for tuition only, not room and board), you are essentially hacking the IRS.  Now, don’t worry, they know all about it.

The IRS tends to show us where they want us to spend or give our money.  In this situation, they aren’t counting these gifts toward your lifetime total. Now, most of us don’t have to worry about gifting over $11.2 Million dollars, but don’t forget, I JUST WON $1 BILLION DOLLARS!

My Cause After I Win the Lottery

It’s a scientific FACT (my favorite kind) that by giving, and doing for others, you become happier! The Mental Health Foundation says that, “When you help others, it promotes positive physiological changes in the brain associated with happiness.”

There are also physical benefits to helping others. Positive emotions reduce stress and boost our immune system, and in turn can protect us against disease.

So, for these reasons, and to keep myself in check, I’ve decided on a couple of causes that are most important to me. My world is turning upside down with my newfound wealth. By helping out in this way, I hope to keep my head out of the clouds and and my feet firmly on the ground.

I will work with my estate planning attorney to form a couple of foundations to help me with this.

Improve the education system

As my two boys approach school age, my wife and I have begun to research and contemplate the kind of education we’d like our children to have. Do we put them in public or private school? How are the school systems in our area…in our country?

I think it’s relatively common knowledge that our education system in this country is falling behind. While we are a great country in so many ways, we are failing when it comes to educating our children.

There are other countries with vastly different education systems.  I want this foundation to focus on bridging the gap between our approaches. There are many direction this could take…creating a new curriculum that encourages a more hands on approach to learning is one example.

In Finland, the students learn in the classroom half the time, then leave the classroom for rich extracurricular activities that keep them learning outside of the classroom. This allows the teachers to spend the rest of their time developing professionally. The list goes on and on…

Singapore is the “smartest country in the world” when ranking high-school students. The country has placed a priority on developing a strong, consistent education system for TOMORROW’S economy. They started thinking for the long game.

I love this quote from an article on, “One thing that’s been clear to them is that the world economy no longer rewards people just for what they know. Google knows everything. The world economy rewards people for what they can do with what they know.”

This is my goal.

Our broken environment

We are becoming more and more developed. We are leveling trees and natural habitats so we can have another Starbucks or Whole Foods. In Florida, we’ve developed issues with our water and marine life partly due to our farming practices.

We are focused on short term economic results while ignoring the long term health of our one and only home. While it’s hard to imagine that a relatively small foundation can make a dent in this problem, we only get one shot at repairing it so every little bit counts.

I won’t pretend to be an expert in solving any of these problems. My foundations will provide funding to those organizations that do know how.

A friend of ours started an organization called One of their goals is to plant 1 million trees in Lee County, Florida…our home. I think this is a good place to start.

Financial Steps After I Win the Lottery

There are some choices that I need to make when I win the lottery. To start, I have a couple of options in how I want to accept my winnings.

Lump sum vs. 30 Years of Payments

There are two “camps” when it comes to this decision. When you win the lottery, you’re presented with the option of taking it all in a lump sum, or spreading it out over 30 years, plus interest.

By choosing to take it in one lump sum I would pay taxes all at once, but be able to invest to my choosing and enjoy future growth and income.

If I chose the 30 year payment plan, it would be to protect myself from ME! I can’t spend it all if I don’t have it all! I would pay taxes each year that the payment comes out, rather than all at once. Taxes go up, taxes go down. You don’t know the tax rates of the future, so that’s a risk.

Personally, I will take it all in lump sum. As you can tell, I have plans. I am comfortable in my ability to manage my finances and would like to be the one to enjoy the fruits of how it’s invested.

Hire a team of professionals

I have absolutely no intention or confidence for that matter in managing this amount of money. The impact of a bad decision is light years more than I’m comfortable with.  I need experts in their own fields to delegate to. I will make it very clear that they each have their role and that I expect them to work TOGETHER. This goes for taxes, investments, legal, etc.

Estate Planning Attorney

As I mentioned before, I will start with an Estate Planning Attorney. I don’t plan on accepting a penny before I have a water tight estate plan finalized.

This will protect me and my family, save us tax dollars and help maintain privacy all at once. I won’t get into the complex estate planning techniques that I’ve come to learn over the years, but believe me, it’s worth the patience and money to get it done before cashing that ginormous check.

Tax Attorney and CPA

While I’ve come to learn a great deal about taxes, I’ll leave this to the experts that think about them day in and day out. I need help to navigate the tax laws with this new complex situation. A CPA will help with filing my taxes every year and a tax attorney will help with any dealings with the IRS…which I’m sure there will be.

When you win the lottery, every penny is considered income. I will be thrust into the highest tax bracket of almost 40%. If I lived somewhere with a state income tax, I’d be paying even more. I will be sending 25% of my winnings to the IRS immediately. When tax time comes next year, the rest will be sent. I don’t plan on doing this with H&R Block.

Investment Management Firm

I have proven to be emotional about my investments…which is perfectly normal. I know that’s not how it should be done, but I’m human.

I don’t want just one person to handle the entire portfolio, not with this level of wealth. I want someone to focus on my investments, a team of professionals all focusing on their own portion of the market.

Maybe, at most, I’ll take a very small sliver of cash and invest it for “fun”. If I lose the whole thing on a small startup that sounds cool, oh well! It’s not nearly enough to hurt me or my plans.

Start spreading the wealth (by being smart)

Do you remember when I mentioned that we all have $11.2 Million dollars to give a way (as a couple) before we start paying gift tax? And do you remember that you could gift directly to a school or medical facility to “work around” that?

Well, you can also give up to $15,000 per year, per person and accomplish the same thing. This is also part of a well thought out gifting strategy.

For example, Ashley and I can write a single check for $60,000 payable to my brother and his wife. I would be giving $15,000 to both Matt and Niesha ($30K total) and Ashley would be doing the same (another $30K) for the grand total of $60,000.

This will be for our closest family…those that we intend to inherit some level of our wealth when we’re both gone. It’s not frivolously giving it away, it’s transferring money (tax free) that we know would end up there eventually.

Plus, we get that “feel good moment” seeing them enjoy their gift.

Be conservative with debt

Debt is toxic. I’ll say that up front. For a lot of people, it’s the problem. But, if used appropriately it can BUILD wealth.

Our country has conditioned us to spend money that we don’t have. Credit card debt is bad. Using leverage to build wealth CAN BE a smart move.

I will never take a loan so that I can “spend”. That would be dumb. I will, however use leverage (taking a loan against an asset, like a home or an investment account) to my advantage.

A good example here is a mortgage. Instead of paying cash, I can get a loan. The bank is using the property as leverage for the loan. The money that I would have otherwise paid for the house, can continue to be invested. The loan will buy the home, that will also likely grow in value. All while paying an interest rate that is lower than the expected growth.

Now, if this EVER gets to a point where the interest rate is HIGHER than the expected growth then I’ll pay it off. I will also never take a loan that would put me in financial strain. It would be better to pay in cash.

Personal Steps After I Win the Lottery

Stay in our home for 1 year

This is something that to me, sounds pretty easy…at least in theory. I’ve already discussed this with Ashley. By making a pact to stay in our home, for the first year, we can settle in to our new wealth the right way.

If we were to upgrade our home and buy 3 vacation homes before we even know how much we owe in taxes, then we’d be off to a bad start.

Keep our day to day cars

The goal here is to make sure that we don’t get caught up in buying “things”. I want us to ease into our wealth, slowly. We both want to not only be rich monetarily speaking, but we want to live a “rich” life.

Travel the US

There is so much of this country that I haven’t seen. While we are still in our current home, I want to see some of the best this country has to offer. I want to jump in an RV (a sweet one!) and just go.

I know this doesn’t require massive wealth to accomplish. As a matter of fact, this is something I want to do regardless. These experiences are what I want to spend our money on first, before we settle in and start upgrading our lifestyle.

Keep the same philosophy about college

I feel pretty strongly about this. I want to help my boys achieve financial success. I want to teach them the value of money. This will be exponentially more difficult to accomplish when I win the lottery.

First of all, if they want to go, that’s up to them. They have an opportunity, wealthy or not, to earn a living doing just about anything they want. Finding something they’re passionate about is more important to me than a degree that may or may not turn into a rewarding career.

But, let’s say they decide to go. They still have to pay for half. I believe there is a direct correlation between paying for your education and how hard you work.

Working hard for a scholarship is earned BEFORE you go to school, so that’s not what I’m talking about. I want them to go to college because it enables them to pursue a career they’re passionate about…and to take it seriously.

I know this might seem contradictory to my cause of improving our education system. Where we have a problem, is in our foundational education (K-12). By the time my boys get to college age, I HOPE they’ve come to decision on what it is they want to do. I HOPE they’ve had the quality education and real world experiences they need to be able to decide on how they want to spend their adult life.

This is about motivating two young men to take their learning seriously.

A dream vacation for Ashley

win the lottery and travel

While there is so much more I would do for her, this is one worth mentioning.

Ashley is passionate about other cultures. She loves to learn and understand how they interact, their religious practices and everything in between. So far this has mostly been through her studies.

I want her to be able to go to these countries and immerse herself in their culture. I want her to actually be there, speak to the people and spend time studying their religions up close and personal.

This is one of the first things I will do for her.

Keep working

I always want to have something to work on. Winning the lottery makes that even more important. I want to look at it as an opportunity to pursue the things that I find most interesting. The financial gain would be irrelevant.

I may go back to school. I most likely would go to a trade school and learn carpentry. I may learn to be a software engineer.

I have every intention of continuing to work with my brother because we really do love what we’ve built together.

The point is not about what I’d be working on, but THAT I’d be working. I never want to become stale and sedentary. Our minds don’t respond well to that.

Explore my own passions more

Over the years, with the focus on school, career, family and everything else, we tend to neglect our own passions. I’ve tended to enjoy the pricier things in my life, like golf, boating and skiing.

When I win the lottery, I’ll be able to travel to the most prestigious and historic golf courses on the globe. I can learn to sail and build with my hands. These are some of the things I can enjoy now that money is no longer in the equation.

I know we all like to think about the things we could do if we win the lottery. Like I said earlier, I do and I don’t even buy lottery tickets!  Daydreaming about what you would do if you win the lottery can teach you some lessons. It can show you if you value material possessions, or experiences. It can show you how much you care about others. It can help you start thinking about wealth, rather than just getting by.

Whether you buy the ticket or not, see what kind of great life you can dream of, then go get it yourself.

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Brad Ruttenberg

Brad Ruttenberg


Sports Fan, Movie Buff, and Anything Outdoors sums it up.  Brad loves spending time with his wife, Ashley, and their two boys.  He helps empower people to take control of their money, bringing them the confidence to build the life of their dreams.

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About Matt & Brad

They are identical twins and money experts.  Matt and Brad Ruttenberg have, combined, over 2 decades of experience as financial planners.  They are known for simplifying money and helping others go from living paycheck to paycheck to thriving financially.


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