The Elevator: Investing with Your Heart: My Money Mindset, Investing Habits, Mental Models, and a Few Apps
The best investments I’ve made have been the ones I’ve loved.
The Elevator explores products, services, and ideas for Founders & CEOs using their business as a vehicle for personal, professional, and spiritual transformation.
I’m David Sherry, founder of Death to Stock, and partner to 15+ Modern Founders & CEOs with a new vision for how we build companies. X, Instagram, Tiktok, Linkedin.
I’ve had founders and CEOs who have exited or who have made a good chunk of cash ask me about how I invest, so I wanted to share my views below. This is my own view, so don’t take it as investment advice, and there are so many ways to be successful investing, so this is just one way of thinking and viewing investing in your career.
Just want the apps? Skip to the end.
My biggest TLDR: The best investments I’ve made have been the ones I’ve loved. Most mistakes I make are when I follow others without having any of my connections to the company or assets.
My personal investing mental models:
Every investment is a vote for my future self.
First, I think of it as placing money into a vehicle (like a car) that’s driving into the future.
Over time that vehicle either gains value or fades and loses value relative to every other vehicle. When I have cash, I get to vote on what I believe will lead to a better future, financially or for the world.
When the future does arrive, did the vehicle accrue more value such that I would be happy with it?
Creating leverage by giving smart, hard-working people money.
My income can and will grow quickly, however, I like to diversify my work by giving money to other people who can put my capital to use. It’s like having an extremely diversified career.
I think of investing as creating leverage on my own time by giving the money I make to many more people smarter than me… Who do I think would do MORE with $1,000… myself, or 1,000 people who work at say, Tesla? Who is better at making money, myself, or Jeff Bezos?
This is a freeing thought – I don’t have to be great at doing the compounding of the capital, just picking the dozens, hundreds, or thousands of people who are.
When I give money to other people by investing in their company, I’m investing in everyone in that business, everyone who’s showing up to the office Monday morning.
Of course, just because there are smart hard hard-working people doesn’t mean the investment will do well.
Investing in secular trends
One way I see more safety in investing in smart, hard-working people is investing into secular trends – these are network effects of ideas, people or technology that I believe are growing regardless of who is at the helm. Basically, I’m inverting the previous idea, saying
“What would be successful even if the people didn’t do a good job managing my capital through the vehicle of their business?”
This concept is best outlined by what I think is the best meme ever made, the Bell Curve meme. If this is your first time seeing it, the bell curve meme shows that simplicity sits on the other side of complexity. Simplicity exists both in simple thought forms and through mastery.
Buying All-Time Highs
Investing in secular trends means you need to have a long time horizon. It also means you can and will buy all-time highs. One counter-intuitive concept that changed my investing was getting more comfortable buying all-time highs when I believed the trend is still just beginning. This is the opposite of the value investing model by Buffet which is all about a good entry price. For me, I focus more on the trend and less on price, and sometimes use positive price appreciation as a signal that confirms the trend, not noting a top in a trend.
This is a nuanced idea so be careful with it, and I recommend this book by Howard Lindzon on the topic.
Investing in what you love ❤️
Let’s take a left turn and talk about the energy of investing.
The best investments I’ve ever made had an energy to them… I loved them. It sounds strange to say that but it’s true. I had love for what the company or product or idea was doing in the world. I loved the simplicity or elegance or concept. There was a beauty to it.
For example, reading the Bitcoin Whitepaper was an incredible moment of discovery, almost like discovering E=MC2. It was so beautiful, so elegant, so masterful, that it lead me down the rabbit hole to study it and progressively get more comfortable buying and owning it.
Today, I simply LOVE buying Bitcoin. I feel good every time I do it. I get a dopamine hit every time I do it beyond any future gain, I get it right then.
For me, there has been something about investments I’ve loved that, over time, has lead to better results.
It’s almost like I can invest in the asset without needing the return. Sounds crazy, but that alignment feels so good.
Every time I’ve made a mistake in investing, it was chasing an investment I didn’t understand and wasn’t coming from a place of love. It was a desire to follow, chase, grasp, seek. I wanted something with that investment that wasn’t pure.
Buy Investments Like You Buy Coffee
One thing I’m in the habit of is trying to buy assets every single week. It doesn’t matter if it’s $5, $500, $5,000. Every week I’m buying something.
I buy investments like I buy coffee’s.
So many apps make this easy now. Not only do I have automated investments, I also like to personally press the buy button. The key here is to get dopamine hits from buying, not from selling. The dopamine hit (which is actually the drive to do something, not the feeling after you do something) is best paired with adding to your portfolio rather than trading or selling. I would be in bad shape if this habit was trading.
Here’s another great book on that topic:
Some quick-bite reflections
I’m happy I called a good deal of friends who are Angel Investors and was talked out of angel investing. That felt like “the thing to do” and not “the thing I love to do.”
I like to be liquid, this is just a preference. Crypto (to date, might change) has been venture-style investing without the venture-lock-up period. This cuts both ways but I prefer to invest in more liquid vehicles.
Cash from rates at 5% means I’m holding more cash than typical. My plan is basically just ride that as the rates wind down, if they do, and then spread out to risk assets. This is very typical. Money goes where it’s best treated :)
This is somewhat common wisdom, but I like to “bite” at something before I understand it. I commit to an idea or investment in a small way before I’ve done all my research because the capital commitment creates an attachment that makes me want to do more research.
Here are a few of my favorite investing apps:
Acorns: This app lets you turn on “round-ups” which take any transaction you make or purchase and round the transaction up to the nearest dollar. So daily when I buy things I’m getting 16 cents here, 27 cents there all added to an index fund.
M1 Finance: This is where you can build your own portfolio through “Pies.” “Pies” let you design your own basket of products in “slices”. Then, every time you “buy” it will evenly distribute that purchase amount across every “slice” of your pie. Great way to build your own portfolio.
Uniswap: Omg, mindblowing experience. Somewhat technical (although not really). A glimpse of the future.
Rally Rd.: Alternative assets via fractional shares. Playing cards, watches, classic cars.
Investing is so complex, and it’s ever-changing. Like anything, what we believe about investing and finance makes a massive difference in our decisions and outcomes. This post focused more on my mindset because it underlays everything.
If you want to talk more specifics, you know where to find me.
Much LOVE to you all and happy investing!
xx David
love this man