I had the pleasure of sitting down with
, a sharp mind on Substack who covers a broad range of topics, from investing in individual stocks and Bitcoin to philosophy and politics. If you’re not following his work, you should be. In this conversation, we covered a lot of ground, from US geopolitical strategy to stock market opportunities, and the video is attached for those who want to dive in. Below is a recap of our discussion.The Godfather Playbook: Trump, Greenland & U.S. Resources
One of the most interesting comparisons we discussed was how the Corleone family in The Godfather made Moe Greene an offer he couldn’t refuse when getting into the casino business. This ties into Bagholder’s latest post, Connecting the Dots, where he argues that Trump’s interest in buying Greenland is a similar power move—an attempt to secure valuable resources under U.S. control. Post from
is below:
While many dismiss the idea of acquiring Greenland (or even taking back the Panama Canal), the broader point is that the U.S. is aggressively looking for resources to not just hold as reserves, but to monetize into cash flow. The leverage the U.S. has in these situations is often underestimated, and
breaks down why these kinds of moves shouldn’t be mocked outright.Monetizing U.S. Assets: A Sovereign Wealth Fund Approach
One example of monetizing assets could be TikTok, a company that, under the right circumstances, could have its ownership partially shifted to a U.S. sovereign wealth fund.
Beyond tech, there’s also untapped potential in U.S. energy reserves. How much equity would ExxonMobil be willing to give the U.S. government in exchange for drilling rights in untapped areas? According to
, this kind of monetization is inevitable and could be a significant revenue source against the country’s growing deficits.Dutch Bros vs. Starbucks: A Changing of the Guard?
is bullish on Dutch Bros (BROS), even though he doesn’t personally hold a position. He sees it as a growing competitor to Starbucks, with a younger, highly engaged customer base. The stock’s valuation looks reasonable, and we dug into some compelling comparisons between BROS and Starbucks (SBUX).We also explored a parallel between CAVA and Chipotle, where CAVA is learning from Chipotle’s past mistakes and refining its business model to avoid similar pitfalls. Similarly, Dutch Bros (BROS) could be capitalizing on Starbucks’ missteps over the years, positioning itself as the next major player in the coffee space.
For example, both the CEO of BROS and CAVA have the advantage of observing how their predecessors scaled and identifying what worked—and what didn’t. By studying Starbucks and Chipotle, these newer “fast casual” chains can focus on expanding margins, optimizing store efficiency, and streamlining operations in ways their competitors might have struggled with in the past.
For CAVA, this could mean refining its supply chain and operational efficiency to avoid the cost overruns and labor issues that have occasionally hurt Chipotle. CAVA is also leaning into digital ordering and customer experience improvements earlier in its lifecycle than Chipotle did, which could help it scale more efficiently.
For Dutch Bros, the company is taking a more localized and community-driven approach compared to Starbucks, potentially avoiding the pitfalls of rapid global expansion. Dutch Bros may also be better positioned to optimize store layouts and staffing models, learning from how Starbucks has navigated challenges like rising labor costs and operational bottlenecks in drive-thru locations.
Tesla: More Than a Car Company
was bearish on Tesla (TSLA) three years ago but has since flipped bullish. Like many long-term Tesla bulls, he now sees the company as more than just an automaker. One of the most exciting growth areas for Tesla is its energy pack business, which is scaling rapidly and operates with extremely high margins. Tesla dominates this market share with a massive backlog of orders, similar to how AWS quietly built long-term enterprise commitments that transformed it into Amazon’s powerhouse a decade ago.Beyond energy, Tesla’s future growth also hinges on autonomous driving, robotics, and chip production—all of which have the potential to scale massively. If these divisions execute as expected, Tesla’s valuation will have a lot more room to run.
DraftKings: A No-Moat, Overpriced Bet
and I had a friendly debate about DraftKings (DKNG), though it wasn’t much of a debate because I mostly agreed with his take. His concerns:Cutthroat competition in the sports betting space, making it hard for DKNG to establish a durable moat.
Valuation concerns, as the stock trades at 6x sales despite not being profitable.
Stock Chart and Balance Sheet look unhealthy
Simply put, he sees DraftKings as overpriced and lacking long-term defensibility.
I agree with these points, but my concerns focus more on three key areas:
The High Cost of Acquiring New Customers
Each time a new state legalizes online sports betting, DraftKings and its competitors engage in an expensive arms race for customers. These costs—whether through aggressive marketing, sign-up bonuses, or promotions—erode profitability.Regulatory and Taxation Risks
Sports betting is one of the most heavily regulated industries, and every state operates with different rules, tax rates, and licensing requirements. Some states impose extremely high taxes on revenue, making it difficult for operators to turn a profit even when they capture market share. As more states legalize, these tax structures could become an even bigger hurdle for DraftKings.Management’s Stock Sales
DraftKings’ management continues to sell shares at a steady rate. Since the company went public via a SPAC merger, many of these sales are likely tied to structured selling plans that allow insiders to gradually unload shares. Consistent selling by executives—especially if tied to stock-based compensation—may have contributed to a dilution effect over the last few years.
Having an Exit Strategy: When to Cut Losses
While I’m a buy-and-hold investor,
brought up an important point about having an exit strategy when starting a position. He follows a rule of layering in and out of stocks, which is somewhat similar to a stop loss but not quite the same.When he had the opportunity to elaborate on this approach, I found myself somewhat agreeing with his reasoning. While I avoid stop losses, there are moments when holding on to losers isn’t the right move, and his framework for scaling in and out of positions has its merits.
Final Thoughts
This was a great conversation, and I want to thank
for joining me. We covered a broad range of topics, and I’m sure we’ll do it again soon.P.S. To be clear, although it sounds like I’m hating on Draftkings, I am still long as of today. That doesn’t mean I’m not frustrated with the business.
If you enjoyed this discussion, drop a comment and let us know what other subjects you’d like us to cover.
Disclaimer: This blog is for informational purposes only and does not constitute financial advice. All opinions are my own, and I am not a financial advisor. The information provided reflects my personal views and is intended to encourage discussion and thought among readers. Investments involve risk, including the loss of principal, and past performance is not indicative of future results. Always conduct your own research or consult with a qualified professional before making any financial decisions.
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