- On The Fly
- Posts
- #121 Behind The Grind is LIVE!
#121 Behind The Grind is LIVE!
Plus: Take Advantage of Being Young and Free!

Welcoming you back with our first ever Interview Series...Behind The Grind š¤
This isnāt your typical interview series, though. It wasnāt launched to spotlight people whoāve made millions of dollars or to teach you to go make millions for yourself. Itās not about highlighting exceptional accomplishments and making you feel like sh!t while you wonder, where TF do I even start!?
Itās intended to be authentic AF. Itās intended to interview real people, some of whom I have real relationships with already. Real people sharing whatās worked for them re: branding, being productive, and fattening that wallet.
Instead of cold DMāing the wealthiest people in the world, weāre starting with my network. People that I have built a relationship with. People that Iām certain have actionable value to share. People that care to help people like you.
I hope you enjoy this interview as much as I did!

Behind The Grind: OTFās 1st Ever Interview with a Finance Proš
Making Cents of Opportunities
Food For Thought About Doing Over Thinking

BEHIND THE GRIND šÆ
Finance, Freedom, Family: Tommy McGrath (A Dude in His 40s with 3 Kids)

What are your current hustles? Iām a Portfolio Manager for a large family office focused on trading FX and liquid macro futures. Iāve been trading currencies since 2005, trying to make it cheaper for Americans going abroad! On the side, Iām an active investor in equities, crypto, and private placements, while also dabbling in some sports betting.
Whatās your āWHY" for what you do? Performance-based compensation forces you to outwork your competition to try to find and take advantage of your perceived edge. Trying to find this edge is the motivation. Coming up with a thesis, testing it out, and seeing it work is the goal. It allows you to learn from mistakes. Thereās often an element of game theory involved where you need to calculate risk vs reward. It can be highly stressful, create self-doubt at times, but itās highly satisfying when you get the outcome you hoped for.
But the answer to whatās my WHY is freedom. Being able to maximize my time with my kids and family.
LETāS FATTEN THAT WALLET š°ļø
How do you define a rich life? A rich life is a happy life. At this stage for me, thereās no bigger joy than making my kids happy, but in general a happy life is one that allows you to be the best version of yourself. For me, itās always been being able to maximize time with friends and family. Creating memories through different experiences. Having a job that gives you a sense of fulfillment and purpose. Spending time wherever your happy place is. When you can combine all of those, itās an on-top-of-the-world feeling.
Share one thing about money that would benefit our readers - The power of compounding money. Being able to earn money on your money over time, even with minimal risk. Examples would be index investing, high-yield savings accounts, and interest-bearing bills.
What is one money move you regret? What's the lesson that came with it?
Not buying bitcoin when it first came out because I didnāt take the time to learn about it and initially thought it was a gimmick. The moral of the story is, do your own research and donāt be afraid to go outside the box.
A second regret is not starting to invest earlier. The thought that investing a small amount of money isnāt worth it [is one I regret], but over time it adds up.
What's the best advice you've been given about money, and how do you apply it?
With rent and housing prices at all-time highs, the question of how should I be paying or what can I afford is often a big topic. A general rule of thumb Iāve followed is you should not be paying more than 33% of your after-tax monthly income on your housing in order to allow you to have money left over for savings and general enjoyment.
A couple others:
āTakes money to make moneyā - At some point we have to take some risks with our savings if we want to make more money. A prime example is crypto, which is highly volatile but offers big upside returns.
āDo what you love, and the money will followā - Easier said than done, but creating a business, chasing a passion and being rewarded for it, and generally not being driven by your income will create more happiness.
LETāS ELEVATE THAT BRAND š
What's the best advice you've been given about personal branding, and how have you applied it?
Always be authentic, and kindness and friendliness will always open doors.
What's one tip you love when it comes to negotiation, and how do you apply it?
You have to be willing to give a little in order to get. And if you donāt ask, you donāt get. Understand where your hard line is, and what would make you walk away.
LETāS BOOST THAT PRODUCTIVITYš
How do you stay productive when times get challenging? Whatever challenge you are dealing with, there are thousands of other people dealing with more serious issues. Knowing that can get you to power through. And also, lots of Diet Coke!
What's your take on AI? Love it, hate it or still figuring it out? How do you plan to use it to your advantage in the long term?
Still figuring it out. Itās the future, and I donāt want to get left behind. Iām trying to learn as much as I can.
What is one lifestyle habit that boosts your productivity to get sh!t done?
Sweating. Getting a workout in. Always clears the mind and makes me feel better.
When was the last time you burned out ā and how did you bounce back?
I canāt remember the last time I wasnāt burned out. Itās just powering through. With 3 young kids, a long commute, and long hours at work, thereās little time for myself. Itās important to maximize weekends, squeeze in workouts when I can, spend time with my wife, and take the occasional night to just disconnect.
How important is rest to you? When you're well-rested, what's different about you? Mentally, emotionally, creatively?
Everything you read will tell you the importance of rest and sleep, but unfortunately I donāt get enough of either. Proper rest keeps your emotions in check and allows you to stay rational and balanced. It allows for recovery. When I get proper rest, I am in a much better mood.
RAPID FIRE FUN š„
One thing you used to waste money on that you donāt anymore: Buying bottles in the club! Times have changed.
A splurge youāll never regret: Any travel experience. Always spend money on experiences. A personal one would be my wedding. Itās one Iāll never forget and went exactly how we envisioned it.
Bucket list place to travel: St. Barth. Itās the best.
If you had to completely change careers, what would you choose and why? I would be involved in sports management. Itās a passion of mine.
If you could text your younger self one quick message, what would it say? When in doubt, take the chance.

MAKING CENTS š°ļø
POV - No Kids Vs. Having Kids
When doing this interview, one thing really stood out for me: the money POV of having kids vs not having kids. Tommy didnāt dissect how expensive kids are, but the thought of it made me wonder what the opportunities are without having them (yet) and how important it is to take advantage of that starting yesterday.
My older brother and sister each have 3 kids, and money is always a topic that comes up. I am confident anyone with kids has that in the back of their head morning, noon, and night.
I donāt have kids and that associated stress yet, which means my opportunity to go out and make MONEYYYYY MONEYYYYY MONEYYYYY is now! Iām not saying I wonāt have chances when I do have kids, but a lot of the foundation needs to be laid now.
So with any extra cash I have, Iām focused on investing, though not exactly in the way Tommy talked about above. Sure, some goes to a high-yield savings account; some goes to my wedding fund; and some goes into traditional investments, but for the most part, I want my leftover money - before it becomes diaper money! - to go into investing in ME and my project(s).
Iāve paid for courses on marketing and branding. Iāve paid to talk to a multi-million dollar media entrepreneur. Iāve paid for stuff that will future-proof myself in this digital world we live in. Iāve paid to play. And Iāll continue to do so until baby food and onesies become a prioritized expense.
You too, should pay to playā¦while you can. And when you begin to play and build something for yourself, you need to be relentless. You need to be able to work through the burn out you feel at times. Heck, I burn out multiple times a month while juggling my career, writing & scaling this newsletter and putting out video content. I donāt have kids that tire me out, so this is my chance to really lean in and go after what I want.

And I just love how transparent Tommy was when asked about his burnout. He said: āI canāt remember the last time I wasnāt burned out. Itās just powering through. With 3 young kids, a long commute, and long hours at work there is little time for yourselfā
Think about that for a moment: Thatās real talk. Real advice.
So in your pursuit of going after the life you want and whatever money goal(s) you have, remember the best time to take advantage of that is while youāre kid-less, while you have fewer responsibilities. Fewer responsibilities means more opportunity to buy into yourself and go get what you want for your future family.

Need fresh ideas for social? Download the 2025 Social Playbook for trends, tips, and strategies from marketers around the world.
Get insights from over 1,000 marketers on whatās working across LinkedIn, Instagram, TikTok, and more. The Social Playbook helps you stay ahead.

FOOD FOR THOUGHT š

šÆ
Before You Go
I am genuinely curious how people approach life & money, so being able to interview Tommy was a cool experience. We canāt thank him enough for his participation.
In the meantime, if you have a quick second, please let us hear from you in our exit poll. It always means a lot to us.
Community Poll š
When learning from peers, what lessons are most valuable to you? |
Last Weekās Trivia Results:
What Is Money Made Out Of?
Pressed Bamboo and Silk
A Combination of Cotton and Linen āļø
Paper
Recycled Fibers

As always, see you next Tuesday š¤

Find Dan on LinkedIn
You are now On The Fly & In The Know.