Silly Money
What’s Inside my Personal Finance “Stack”
Free Tax Workshop on Wednesday
Are you horrified by the amount of taxes you need to pay this year?
I’m hosting a free workshop on Wednesday at 2pm ET called How to Pay Less in Taxes in 2025.
This workshop is for both business owners and W-2 employees and we’ll share 7 different strategies you can employ to reduce your tax bill.
We’ll have a special gift and a live Q&A for everyone who shows up live, and also send a replay to everyone who registers.
This is a juicy post.
Instead of telling y’all what to do, I am sharing exactly what tools and services I personally use to run my entire financial life.
This includes the specific providers I use for:
As an added bonus, I’ve included some of the fun personal finance and travel “hacks” I’ve found over the years.
By reading this, you will understand how I manage my own finances — and if your situation has any similarities with mine, you may find a provider you like.
Full Disclosure: I'm writing this as myself, not as some investment adviser or broker-dealer representative. This is just educational stuff and my personal thoughts - not investment, legal, tax, or professional advice. While my startup Carry owns an investment advisor and broker dealer, this is not meant to be an advertisement and nothing here represents them. Financial decisions involve risk, including losing money. Taxes are complex. Please do your own research or talk to a licensed pro before acting on anything you read here.
Investing
Over the last few years, I’ve tried almost every single investing platform to figure out exactly what works for me.
As context, I highly recommend reading my post How to (Not) Invest Life-Changing Money — I break down how I iterated upon finding my ideal approach to investments.
Right now, here are exactly the platforms I use for investing today:
Direct Indexing
Most of the dollars I invest today go into direct indexing into the stock market.
I do not believe most investors should try and find “alpha” (aka differentiated performance) by making better investments.
Instead, we are better off indexing into the stock market which has historically returned an average of 8% every single year.
However, instead of buying an index fund or Vanguard ETF, I choose a “direct indexing" strategy where I buy every single stock individually.
Why do I do this?
Tax efficiency.
By owning every single stock, I benefit from increased volatility, and can potentially harvest up to 40% of my initial investment as a tax loss. This is very meaningful to me as this loss will offset other gains I may have across my portfolio.
The direct indexing provider I use is Frec.
I love them for a few different reasons:
They only charge me 0.10% for most portfolios, which is comparable to a Vanguard fund.
I created my own portfolio, and I can automate a weekly transfer into this portfolio — so I can truly set it and forget it.
The team is constantly shipping new features, and I’m seeing the experience get better literally every week.
Here is what my portfolio looks like on Frec:

My favorite investing tools are “set it and forget it”
I’ll soon share an even more detailed post breaking down exactly how I use Frec to automate most of my investing.
If you want to try Frec, you can use my referral link and receive a free $250 to invest.
Retirement Accounts
This one is easy.
I use my own startup Carry for every single retirement dollar I have:

Look at that dashboard 😍
I’m biased but this is why using Carry is a no-brainer for me: (you know, aside from the fact that I run the company…)
Solo 401k
The Solo 401k is a game changer for any random self-employment income — I contribute almost all my 1099 earnings to my Carry account.
Backdoor and Mega Backdoor Roth IRA
I do a backdoor Roth IRA every single year — the Solo 401k allows me to empty out my Traditional IRA so I am not subject to the pro rata rule.
Support for Traditional and Alternative Assets
The fact that I can invest my retirement dollars in both traditional assets and alternative assets like startups and crypto is very cool.
My long term goal is to emulate what Peter Thiel was able to accomplish with his $5B Roth IRA.
My strategy is use my Solo 401k to get a lot of dollars into a Roth IRA, and then use the Roth to take the occasional bet on assets with asymmetric upside. No other platform will allow me to do this as elegantly as Carry.
Stocks, Bonds and ETF’s
I need to start simplifying my providers here because I use a little bit of everything right now.
But as of today, here are the brokerages I use:
Goldman Sachs
I’ve written about them extensively in my first article to launch this newsletter. There are lots of benefits to the concierge experience offered, but this is undoubtedly a very expensive choice.
Charles Schwab
Everyone needs one of the “big three” (Schwab, Fidelity and Vanguard) — and relatively speaking, I find the experience on Schwab to be the best. I use my Schwab account for the majority of my self-directed individual stock holdings.
Robinhood
I have mixed feelings about Robinhood — their UX is the best in the game, and they are improving at a much faster rate than anyone else. But, I struggle to use them for more than play money until they start taking tax efficiency seriously. Still my go-to for fun gambles, particularly on mobile.
JP Morgan
I use them as my primary banking partner, and they allow you to borrow against any stocks held in the investment accounts there. This is less relevant today, but I set it up when we were at near zero interest rates.
Startup Investments
One of the most painful parts of my personal finance setup is tracking the 100+ startup and fund positions I currently own.
This has led me to create a new rule for myself in the last few years:
If the investment cannot be made on a vehicle controlled by Angellist, I am simply not going to invest.
This rule is not as limiting as it may appear — I can still make the majority of startup investments via Angellist. These are typically either set up as:
Direct investments into an Angellist “SPV” or “RUV” aka set up by the company
An investment from a venture fund I run via Angellist. Over the years, I’ve set up five separate venture funds on the Angellist platform
The biggest benefit to me of investing via Angellist is a consolidated tax packet at the end of the year. Even though this generates hundreds of K-1’s, it has details on all my startup investments in a single place.
Without this, the madness of chasing every individual provider and investment to keep track of capital gains, losses and distributions is exhausting.
At the risk of sounding like hyperbole, I genuinely do not think any return I may make investing in deals personally or via bespoke fund solutions is worth the amount of time and stress to keep track of it.
Banking
Personal
Despite trying lots of neobanks and fancy new startups, I’ve settled on a very old school choice as my primary banking partner: JP Morgan Chase.
When I first moved to America, Bank of America was the only provider willing to set up a bank account for an international student.
A few years later, I migrated over to Chase which had a substantially better online experience and stuck with them.
After selling my business, I got invited to become a client of the JP Morgan Private Bank, and I’m a fan for several reasons:
White Glove JPM Service
The team at JPM Private Bank has always gone above and beyond when I’ve needed anything. Typically, it’s been at a time of chaos — like the time all my credits card got stolen or the numerous times I’ve been stranded without a card in a random part of the world and needed them to overnight me something. I apologize for being a painful client, but they have been great.
Better technology via Chase
While you get the premium JPM service, they still rely on Chase for the web and mobile interfaces which is the best of any of the old school banks.
Costs nothing
JPM Private Banking makes their money on the investment products they sell. I do not manage my investments through them, so do not end up paying them anything directly. They likely still make a reasonable amount on the cash I hold with them etc. but this does not directly cost me anything.
Heaviest credit card
Mostly kidding, but the JPM Reserve is no joke.
If I know you personally, and you believe you’d be a good JPM Private Bank client, email me and I’ll try and get you a referral.
Business
Mercury wins this and it isn’t particularly close.
I first used them for a consulting LLC I had setup, and when it came time to choose a primary banking provider for Carry, they were the very obvious choice.

One of the biggest software upgrades from my first startup to second company
They have the cleanest interface of any provider, make painful things like wires relatively straightforward and are led by an impressive founder constantly shipping new features.
If you want a free $250 from Mercury, you can use my referral link.
Credit Cards and Travel
If you read my article on 7 Things I Wish I Knew About Money in 20s, you’ll know that I used to be against credit cards and any kind of debt for a very long time.
But, ever since I discovered how powerful credit cards can be to travel in style for (almost) free, I’ve been a huge proponent.

Flying Emirates First Class for free is a radicalizing experience
To me, credit cards and travel are inextricably linked so I’m talking about both of them in the same section.
As with most things personal finance, I’m not a hyper optimizer — I enjoy the Pareto 80% of the results with 20% of the work.
Ironically, I only started getting into optimizing credit cards after making a reasonable amount of money. The more you spend, the more worth it it can be to figure out how to fly first class for free.
Credit Cards
I use only two credit cards — both of which are paid and likely not the best option if you’re trying to keep a low annual burn, but I enjoy them both.
I use the:
American Express Platinum Card
JP Morgan Reserve Card — this is the private banking version of the Chase Reserve Card
For most people, either one of these options is likely good enough — but I personally enjoy having both for different reasons.
This is what I enjoy the American Express Platinum card for:
Buying Flights:
Amex gives you 5x the points for any money you spend on flights. This is in addition to any rewards you receive from the airline for booking.
Hotels:
My favorite places to stay are typically found on the Amex Travel website — and by simply booking a hotel there, you get 5x the points AND $100-$150 credit per stay AND a late checkout and a host of other benefits.
Transfers Out:
You can transfer out your Amex Rewards points to most international travel partners.
And the JP Morgan Reserve Card is good for pretty much everything the Amex doesn’t cover:
Supports Travel Partners Amex Doesn’t:
The few travel partners that Amex does not support — like United Airlines and Hyatt — are supported by JP Morgan. Between the two, I can transfer my points to virtually any partner.
Everything Else:
Outside of travel, you generally get a more generous quantity of points for everyday purchases from JPM.
Having both cards also adds redundancy in case I need a higher credit limit or I lose a card — and gets you access to airlines lounges by both networks.
Ironically, I don’t particularly care for lounges or too many of the fringe benefits.
Airlines
Having grown up in the Middle East, I was surprised by how much most airlines in America suck compared to those in Asia.
However, given my location (NYC), I decided to make Delta my primary US carrier since they have the best premium experience with Delta One.
With that said, when it comes to redeeming free travel, I almost never redeem my points on Delta since they offer you terrible value.
I typically use one of the following carriers for redemption:
Emirates
Eithad Airlines
Qatar Airways
Flying Blue (KLM, Airfrance)
United Airlines
Remember: you can typically get substantially better value for your point by transferring out to a partner vs using the credit card travel portal to book.
Hotels
After recently running the numbers, I was shocked to see I spend 30+ nights in hotels every year (largely traveling with family).
For hotels, I like staying in nice places and typically book most of my hotels via the Amex Travel Portal since:
They have the nicest hotels in any city in their inventory
You get 5x the points for booking those hotels
You can “double dip” by also getting points for the hotel loyalty program in lots of cases (like premium Marriott properties)
A host of fringe benefits like a 4pm checkout, $100 resort credit, complimentary room upgrade and more.
I am a member of both Marriott Bonvoy and the Hyatt Rewards Program, and these can be useful if there is a very specific place I want to stay at.
By my estimates, spending a small amount of time on credit card optimization, I earn about ~6 figures a year in annual, untaxed value.
Taxes
Despite the fact that I run a startup to help people save money on taxes, you may find it reassuring that I dread doing my taxes just as much as you likely do.
Personal
I went from having incredibly straightforward taxes for the majority of my adult life to an immensely complicated situation in only a few years.
For most of my professional life, my approach to taxes went like this:
I would do absolutely nothing until April 14.
I would then panic and log on to Turbotax. I would hurriedly “do my taxes” and optimize for speed versus saving money.
But that was totally fine then as all my income was a single W-2 salary and a few 1099’s from random brokerages.
But, my life changed in 2020 after selling my startup.
I hired a big, flashy tax firm — Andersen Tax — to handle the big tax planning pieces around my sale, and they filed my returns over the next few years.
Eventually, I churned from them for a several different reasons, but the two big ones were:
Very little to zero proactive tax planning
Despite paying premium prices, we did very little work to proactively reduce my tax bill after the sale. We never even did quarterly estimates on time, and as a result, I ended up paying even more in taxes.
I felt like a tiny cog in a giant wheel
This likely came with the territory, but being such a small client at such a large firm resulted in getting treated as an afterthought. My emails were not responded to promptly and when issues would (inevitably) arise it would take a very long time to find a resolution.
So in 2024, I moved over to the custom tax practice we have inside Carry called Carry VIP.
You may think my own company would let me use the service for free, but sadly, I’m getting the full customer experience and paying full price!
My experience as a very biased Carry VIP customer so far has been extremely positive, but we’re still working on being able to ramp up capacity.
A couple of things I have enjoyed as an end customer:
It’s been great to be able to dog-food our own product as a paying customer. I can immediately see the strengths and the areas to be worked on.
Carry VIP is focused on proactive tax optimization — and we have already found a single opportunity that could save me mid 6-figures in taxes that more than offsets the cost.
If you also have a relatively complicated tax situation, and are looking for a program that could save you money on taxes, you can fill out the consult form on the Carry VIP website.
And maybe, if you mention you read the post by the guy who started the company, you could receive a 20% discount on your first year.
Trust and Estate
In addition to filing taxes as an individual, I set up two trusts before selling my company:
A Charitable Remainder Unitrust (CRUT)
A Dynasty Trust
Each trust allowed me to multiply my $10M QSBS limit, while also helping move assets outside my estate.
While these trusts were historically painful to set up and operate, I’ve since started working with the team at Valur who handle the entire implementation and tax reporting for my CRUT.
They will soon be able to also support my Dynasty Trust, and I’ll eventually move that over as well.
If you are considering setting up trusts, you can use this link for a free consultation with Valur.
And, stay tuned soon for my deep dive on trusts and when to consider them a part of your estate planning strategy.
What questions do you have about my personal finance stack? If you leave a comment below, I’ll try my best to respond.
See you next week… I have a special announcement to share then!
Disclosures: This post is for informational and educational purposes only and solely reflects the personal views of the author. It is not investment, legal, tax, or professional advice. Any examples, experiences, or investment returns discussed do not guarantee future results. Laws and regulations discussed are subject to change and may not apply to your individual circumstances. Unless specifically stated, posts do not reflect the views or opinions of The Vibes Company Inc. or its affiliates.


