So far this year, I’ve invested $135,000 into 5 different stocks.

My goal is to follow a plan that generates between $100M and $1 billion in my lifetime.

The strategy that I am following was detailed in the first edition of this newsletter. 

If I follow this plan for the rest of my life, then I will achieve at least a $100 million net worth - even if everything else turns to poop.

This allows me to be calm, focused, and aggressive as an entrepreneur, because I have a $100m plan that is independent of my business success.

If I follow the strategy for long enough, then I will be worth over $100 million. Rather than hoping for a big win or a lucky break, I am betting on simple math.

If I do better than average, then it will compound into over a billion dollars, without taking a large financial risk.

That’s the plan.

But… why?

“Ryan, what’s your ‘why’ behind $100 million?”

A friend asked me about “the why” behind this plan.

What is the point of amassing $100 million?
Why try to become a billionaire?
What is your motivation behind it all? 

It’s a good question, because a strong “why” makes a goal worth pursuing. 

But I’ve never had a good answer to this question. 

The search for deep-seeded meaning seems paralyzing to me.

I could spend hours trying to figure out “my why,” but it would just be a justification for doing something that I already want to do.

I could also make up a selfless reason for my goals (“I want to save the whales!”), but that would be a ruse. 

The real “why” behind my investment process is to put my mind at ease. 

My plan allows me to pursue a big goal while reducing my stress. 

I only need to invest $150k per year to satisfy my “base case” projection of $100 million net worth.

If I only hit my minimum required investment, and I only invest into boring index funds, and they only produce at the long-term average, then my wealth compounds into 9-figures within my lifetime. 

Whenever I freak out or feel like I’m falling behind my peers, I remember:

All I need to do is invest $150k a year to create a $100 million net worth. 

I don’t need to “kill it” this year. 
I don’t need to double my income. 
I don’t even need to come up with a new idea. 

All I need to do is follow the plan.

It doesn’t even matter if I get there. It just matters that I follow it.

Now, I can relax into doing good work. I can be present with the work that is in front of me. I can focus on doing work that I find meaningful. 

Following this plan allows me to be present with my work.

Most entrepreneurs think that we need the $100 million before we do what we want.

That makes us feel frenetic and chaotic, constantly searching for the “right plan.” (Or is it just me?)

Now that I have my “$100M Plan,” I can give myself permission to focus on doing good work, which is what I want from having the $100m anyway.

It’s kind of like… I get to have the end result now. 

It gives me a calm mind, and the choice of pursuing the projects that give me the most meaning.

That is my “why.” 

The curious paradox is: when I focus on doing work that I am proud of, I end up making more money, too. 

Why PayPal Is My Highest Conviction Stock, Despite Falling 80%

PayPal stock is the largest investment in my “best case” portfolio, and it is the highest-conviction stock on my watch list (partially because it is also my most researched).

I plan to continue to add to my position as long as the price remains under $90, and I expect PayPal to produce at least a 15% return each year for the next ten years, unless the fundamentals of the business change.

PayPal first caught my attention as a possible investment when it hit a high of $300 in 2021, only to fall 80% by August 2023. 

The stock fell because profits went down for the first time in its history, and many thought it to be a “dying company.”

At that time, the price-to-earnings ratio for PYPL looked very attractive, and they hired Alex Chriss to be the new CEO.

When he revealed a new vision for the company, I perked up. 

Part of the new vision included faster checkouts and increased conversions, something that I know a thing or two about. The new vision also included the PayPal stablecoin, which are extremely profitable businesses. I also liked their vision of a new type of ad platform and their market dominance with Venmo.

The market saw a dying company, but I saw a very profitable company with a renewed vision and a new CEO. The (much lower) price meant that the downside risk was low, and I felt that the potential return was high.

I added it to my watch list, ran the numbers, and started adding to my position.

How I Valued PayPal Before Investing

I keep a running list of companies that intrigue me. Then, I try to get to know more about their executive team, their projects, and their product pipeline.

Once I like a company and understand it enough to invest in it, I wait for it to go on sale.

I am still discovering the best way to value a company, so I have included my current process below.

1. To value PayPal, I multiplied the current earnings per share (approximately $5 per share) by their annualized growth rate of 15%, with a timeline of ten years. This gives me a future EPS of $20 per share.
   
   I also looked up the analysts projections on MarketBeat.com and RuleOneToolbox.com, which both gave me projected 16% growth rates. I went with the lower number.

2. I multiplied this future EPS by a future P/E of 30 (2x the growth rate), giving me a future value of $600. In other words, this projects that the price of PYPL stock will be approximately $600 in the year 2035.
   
   Do I believe that this valuation is reasonable? It looks aggressive, so I give myself a margin of safety in the analysis.

Soooo…. if I assume that PYPL will be worth $600 in ten years, what am I willing to pay for it today? 

Since I want to generate at least a 15% return, then the most I can pay for the stock today is $150 per share.

However, I am an idiot who makes dumb decisions, so I must give myself a margin of safety. For this analysis, I gave myself a 40% margin of safety, which brings my target acquisition price to $90 per share.

That means the most I can pay for PayPal is $90. At that price, I like my upside and am comfortable with the downside.

Therefore, I will buy PayPal stock any time that it is at or below the $90 level. Anything below that is considered undervalued in my book.

Whew. That’s a lot of work to try to beat the market, but I am committed to learning this process and getting better at it over time. 

In February 2025, PayPal fell to $70, which is an irresistible price for me. Although there are other stocks on my watch list (see below), the risk/reward ratio on PYPL at the current price is too good for me to ignore.*

*This is not investment advice. I’m an idiot on the internet who is learning this stuff as he goes. I confess to being a novice at the valuation part of this process, so I welcome any critiques in the comments of this article.

With that, let’s review my actual investments so far in 2025…

• Total Contributions Into “Boring” Index Funds: $75,000

• Total Contributions Into “Best Case” Growth Stocks: $45,000

• Total Contributions Into Speculative Plays: $15,000
  
  Total Contributions Made From January 1st - March 1st: $135,000

  Current Portfolio Size: $1,150,000

  The breakdown is as follows…

Part 1: I Invested $75,000 - 2X My Required Amount - Into Boring Index Funds

Since I am an idiot, I invest in index funds before making any other investments.

To achieve a minimum net worth of at least $100 million over the next 40 years, I must invest approximately $150,000 per year into index funds that produce a 9.7% annual return.

The exact number is $140,000, or monthly contributions of $11,650. This satisfies my “base case” requirements as outlined this article.

I make these contributions first because I have proven myself to be an idiot in the past, so I must have these boundaries in place to save me from myself.

This quarter, I decided to invest more aggressively than required, instead of keeping extra cash in savings accounts.

In Q1 of 2025, I invested 2X my required minimum amount - $25,000 each month for a total invested amount of $75,000.

The contributions were as follows:

• January: $15,000 into VOO (the general S&P 500 index) 

• Additional January Contribution of $10,000 Into VOOG (the S&P Growth Index)
  

• February: $15,000 into QQQ (index for the Nasdaq 100) 

• Additional February Contribution of $10,000 into VOOG (the S&P Growth Index)
  

• March: $15,000 into QQQ (index for the Nasdaq 100) 

• Additional March Contribution of $10,000 into VOO (the general S&P index)

I’ve lost millions of dollars in speculative investments, so I must invest into boring, safe, index funds before picking stocks or making speculative bets. 

Moving forward, I plan to make rotating monthly contributions of $15k into VOO, VOOG, and QQQ, unless or until I discover other funds to include.

Part 2: I’m Buying As Much PayPal Stock As Possible… And I Wish I Could Buy Even More.

Once my base case requirements are satisfied, I allow myself to make contributions into ONE undervalued stock per month.

I keep an ongoing watch list, calculate their estimated value, and invest in the most undervalued companies until it no longer makes sense. This forces me to focus on investing in only the best opportunities in front of me.

This way, I dollar cost average into my highest conviction stocks over time. 

The downside, however, is that I sometimes miss out. For example, I would have loved to deploy into Alibaba this quarter, but it moved up so quickly that I missed the opportunity. 

On the other hand, PayPal has remained below my “buy” price of $90, which has given me an opportunity to build a sizable position.

In Q1 2025, I invested a total of $45,000 into PayPal stock, making it the largest stock in my portfolio.

The breakdown of these placements is below:

• January: Purchased 200 shares of PYPL @ $87.44

• February: Purchased 185 shares of PYPL @ $82.25

• March: Purchased 200 shares of PYPL @ $70.12

(Reading this back, I think: “Why didn’t I just buy an even 200 shares in February?” I have no idea. I’m new at this stuff I guess.)

With PYPL dipping down to the $70 range, the temptation to buy even more is tantalizing. I literally lay in bed thinking about this.

Part 3: Oh, And I Bought The Dip On Bitcoin

I rarely make speculative plays anymore.

Yes, they are fun. Really fun.

Maybe too fun.

They can get me into trouble, so I put guardrails on them.

I try to save speculative bets for the end of the year when I have extra profits. That way, I can make a sizable placement into a real estate project, a private business, or a project that makes me happy.

Last year, I invested $50,000 into a coworking space that I plan to use myself. That makes me happy, and it falls into my “speculative” bucket.

But crypto is just too cheap to ignore right now.

When Bitcoin dipped into the 80k range, I purchased $15,000 worth of it via the BTC ETF.

I mean… how do you not?

Note to self and others: this is why I put guardrails on my investment decisions. Without them, I would be tempted to YOLO into more Bitcoin, Ethereum, or - why not? - Dogecoin. But these assets are impossible to value, and therefore must be done with caution, and only after my foundational strategy is satisfied.

Total Contributions Into Speculative Investments: $15,000 

TL;DR: After investing $135k this quarter, my total portfolio now sits at $1,165,000.

My largest allocations are the following: 

1. PYPL - $130k (down 5%)

2. META - $130k (up 250%)

3. COST - $110k (up 486%)

4. UNM - $100k (up 310%)

5. VOOG - $95k (up 6%)

6. IBM - $75k (up 105%)

Note: this portfolio includes only public equities and does not take into account private investments that may go to zero. See this article for the assumptions between my “base case” and “best case” scenarios.

With that, let’s discuss…

The Next Stocks That I Might Buy…

I keep an ongoing watch list so that I become aware of which stocks are undervalued. Since I only invest in one stock each month, I am forced to invest only in the best opportunities in front of me.

I am also forced to to dollar cost average into my highest conviction stocks over time. The downside, however, is that I sometimes miss out. For example, I would have loved to buy more Alibaba this quarter, but it moved up so quickly that I missed the opportunity. 

Over the long term, I expect that this approach will help me to become disciplined in my valuation process, while making regular contributions only into stocks that I understand and believe in. 

My watch list contains approximately fifteen stocks at any given time, but most of them are nowhere close to being undervalued. Therefore, I have shortened my watch list to only the stocks that look interesting at the moment.

Alibaba (BABA): This is my #1 stock pick for 2025, but it surged too quickly to add to my position. Year-to-date, it is already up 55%, and it has moved too quickly for me to add to my portfolio. If PayPal moves over $90 per share, then I will likely rotate into BABA instead.

Pfizer (PFE): I won’t win any friends by investing in Pfizer, but the story is hard to deny. The stock is down more than 50% from its highs, even though it generates a ton of profit and pays a healthy dividend over 6%. I think the market has PFE undervalued due to concerns about the new administration and RFK Jr.’s involvement, and it looks attractive to me at the current price.

WK Kellogg (KLG): Kellogg’s split into two companies in 2023, and the cereal brand is now operating like a startup. The market cap sits under $2b, despite having brands like Fruit Loops, Frosted Flakes, and Kashi. I think Tony The Tiger alone is worth $1 billion, so I see a lot of intangible value in this company. Recent earnings reports sent the stock near $20 per share, but if it drops back to $15, then I may pounce.

Celsius Holdings (CELH): Despite being one of the fastest growing energy drinks ever, Celsius stock has fallen nearly 80% in the past year. This brings the stock into value territory, but that’s not what has my attention: I had been waiting to see if Celsius would grow via acquisition, and the recent announcement of its purchase of Alani Nu made me sit up and take notice. Now their thesis is clear, and it now makes sense to dive into the numbers to take a closer look.

Target (TGT): Even though my family spends most of our extra time and money at Target, the company was crushed by its most recent earnings report. It now trades at just 13x earnings and pays a healthy dividend (I love dividend paying stocks). It is also one of the few retailers with a loyal following, unique brands, and strong private label brands. The stock is down more than 50% from its all time highs, which presents an opportunity to add to a position in a company that I believe in and enjoy as a customer.

This list does not necessarily mean that I will invest in all (or any) of these stocks this year. Instead, they are simply what has my attention while I dive deeper into the numbers. From here, we continue to invest into index funds and research the companies on our watch list. 

Final Words

It is tempting to get lost in the noise of a potential recession, the next big meme coin, or whatever Trump said this week. 

Even as I write this, Ethereum sits at a price of $2200. It might as well be flashing “Clearance Sale” in my mind.

Everything in me wants to place a large bet on Ethereum, since it looks dramatically undervalued. I am also tempted to make allocations into BTC, Solana, Tiny Co, Rivian, Tesla, and a host of other speculative investments that don’t match my core thesis.

Doing so, however, would be a repeat of mistakes made in the past, when I randomly threw money at investments in hopes of getting a few right. This did anything other than bring me peace of mind.

The Billionaire Next Door plan forces me to develop a disciplined approach that will work over the next several decades.

Even if it falls far short of my targets, the plan itself brings me a sense of financial freedom that I have never experienced. 

Thank you for following the journey as I learn this process and get better at it over time. If you want to follow a little closer, you can join my private investment newsletter through this link.