In a follow-up to their "biggest losers" episode, hosts Sean O'Malley and Daniel Munker discussed their "biggest winners," reflecting on why these investments succeeded and whether they remain buys today. They also touched upon companies they covered but didn't buy, highlighting lessons learned. The hosts emphasized their "skin in the game" approach, holding significant positions in their personal portfolios for every stock covered.
**Alphabet (Google)**
Google, their largest holding, has seen a nearly 100% gain since their initial purchase. Sean's original pitch valued it around $180-$200 per share, based on a sum-of-the-parts valuation. The narrative around Google shifted dramatically: initially feared to be disrupted by OpenAI and facing DOJ scrutiny, its Gemini LLM later became a leader, and Google integrated AI into search. This demonstrates the market's susceptibility to narratives, causing trillions in value swings. While early concerns focused on B2C LLM monetization (expensive compute), the hosts believe the real money is in B2B AI products, where Alphabet's product suite (Gmail, Google Drive) offers a significant advantage.
Current concerns revolve around massive capital expenditures (CapEx) for AI and data centers, estimated at $200 billion this year, potentially $300 billion next. This spending has made Google's Q2 free cash flow negative for the first time since its IPO, leading to increased debt and potential share issuance instead of buybacks. Google Cloud, however, is growing phenomenally (80%+ YoY), with a massive $0.5 trillion backlog, indicating strong demand. Despite these challenges, the hosts remain confident in Google's long-term intrinsic value compounding, though Daniel noted he wouldn't add to Google at its current "optimistic" valuation (70x free cash flow) but would let his winners run, following the advice that "great businesses surprise you to the upside."
**Amazon**
Amazon, a more recent holding (February, up 35% in 5 months), also faces substantial CapEx ($200 billion+), resulting in negative Q2 free cash flow. However, Amazon has a unique advantage in the AI race: it has built a $20 billion internal chip business and benefits immensely through AWS, internal efficiency, and potential e-commerce tailwinds from AI agents. Unlike Google, Amazon's valuation is seen as more attractive (17-18x operating cash flow adjusted), and Daniel indicated he would deploy new capital into Amazon over Google currently. The company's vertically integrated model and diversified businesses, from cloud to payments and advertising, position it well to thrive regardless of AI's ultimate impact.
**Reddit**
Reddit has been a "rollercoaster" winner, with a 140% realized gain after taking profits and a 60% unrealized gain on subsequent re-buys. The hosts chose to trim this position when valuations became extreme, citing Reddit's lower diversification compared to Alphabet. While Reddit's Q2 revenue grew 60%, logged-in user growth was a modest 7% YoY, a metric management decided to stop reporting—a move that raised concerns about transparency and sustainability.
Historically seen as difficult to monetize, Reddit achieved 30% operating margins much faster than anticipated. However, it faces dependency on Google Search for traffic, and AI overviews are reducing click-through rates to external sites like Reddit. Although Reddit's data is crucial for LLMs (Google pays $60M annually, a figure seen as low), the hosts question the company's long-term user growth strategy given the AI-driven changes in search behavior. Despite these concerns, Daniel remains bullish on Reddit's potential as a platform for human interaction in an AI-dominated world, though less inclined to add aggressively given the volatility and user growth issues.
**Lessons from Companies Covered But Not Bought**
The hosts also discussed several high-performing companies they covered but didn't add to their intrinsic value portfolio, drawing key lessons:
* **Remitly**: A remittance company Daniel bought heavily for his personal portfolio (up 80-90%). Sean's skepticism about payment companies (race to the bottom, crypto disruption) prevented its inclusion in the main portfolio. Remitly demonstrated strong "earnings power," rapidly increasing margins. The lesson here was the intrinsic value portfolio's focus on long-term, moat-driven businesses, making it difficult to include companies requiring more active management or with rapidly changing theses.
* **Crocs**: A fashion retail company that doubled in value after Daniel's coverage, but they sold too early. This highlighted the challenge of tracking smaller, more volatile positions and the potential for wider outcome ranges, leading to missed upside.
* **TSMC (Taiwan Semiconductor Manufacturing Company)**: A company they agreed to buy but "forgot" due to Sean's significant concerns about geopolitical risks (China-Taiwan) and the fast-changing semiconductor industry. TSMC, with its "lollapalooza moat" and critical role in chip manufacturing, doubled in value. The lesson was not to be overly binary on risks; a small, hedged position could have captured significant upside even with valid long-term concerns.
* **Dell**: Benefited from AI infrastructure demand, with its infrastructure business growing 70% YoY. Despite low margins on AI server contracts, the sheer volume drove substantial profit growth, causing its PE multiple to expand dramatically (from 8.5x historical average to 22x today). The hosts believe this multiple is unsustainable as CapEx eventually slows, highlighting the market's "forward-looking" but potentially over-optimistic nature.
* **Comfort Systems**: An HVAC service provider for data centers, which they initially viewed as a "boring" business, saw a 5x increase in value. Its specialization in complex data centers made it an unexpected beneficiary of the AI build-out. The lesson was the powerful, often underestimated, impact of macro tailwinds like AI on even mature, less glamorous businesses, while cautioning that such multiples might contract if the AI spending cycle decelerates.
Concluding with a Peter Lynch quote—"All you need for a lifetime of successful investing is a few big winners and the pluses from those will overwhelm the minuses from the stocks that don't work out"—the hosts emphasized the ongoing learning process and the goal of finding long-term compounders.