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The Power of Positioning: What I’m Buying This Month

(October 2025)

Every month, I take some time to slow down, reflect, and make sure I’m putting my money where my conviction is. The market has had a strong year so far, but not every stock is participating equally. Underneath the surface, there’s still real opportunity — especially for investors who can look past headlines and think long term.

This month, my focus is simple: accumulate quality, stay patient, and build around companies that I believe will compound over the next decade.

Let’s dive in.

1. $SOFI — Building the Modern Financial Ecosystem

$SOFI remains my highest conviction holding for a reason. It’s not just a bank. It’s an entire financial platform designed to capture customers early and keep them for life.

Every product SoFi launches feeds another part of its ecosystem — lending drives deposits, deposits drive cross-selling, and cross-selling drives profitability. The company is executing on its vision of becoming a one-stop shop for all financial needs.

The most exciting part? Profitability is already here, and efficiency ratios are improving quarter after quarter. In my eyes, SoFi is still in the early innings of something much bigger.

2. $AMZN — The Quiet Margin Machine

$AMZN continues to prove why it’s one of the best businesses in the world. AWS, advertising, and logistics are driving higher margins and stronger cash flow than ever before.

What I like most about Amazon right now is how focused management has become on profitability. The company has shifted from “growth at all costs” to operational excellence — and that transition is showing up in the numbers.

Amazon isn’t done evolving. Its advertising business is scaling quickly, and AWS is positioned to benefit massively from the AI wave. I see Amazon as one of the best long-term risk/reward setups in the market.

3. $PYPL — A Turnaround Story Hiding in Plain Sight

PayPal is one of the most misunderstood names in fintech. Investors gave up on it too soon, but the fundamentals tell a different story.

PayPal is throwing off billions in free cash flow and using it to aggressively buy back shares. That buyback yield alone creates silent compounding that few are paying attention to. The core business remains incredibly profitable, and leadership is finally simplifying operations to focus on what matters: execution.

This stock doesn’t need double-digit revenue growth to outperform. With a forward P/E that’s still discounted and steady share repurchases, I think $PYPL could surprise a lot of people over the next few years.

4. $FUBO — The Speculative Sleeper

This one is higher risk, but I like asymmetric bets when the setup makes sense. $FUBO has struggled over the past few years, but the company is finding its footing.

Sports streaming is one of the hardest verticals to compete in, but Fubo has carved out a niche with loyal users and strong engagement. If advertising improves and partnerships keep expanding, the upside could be huge.

It’s not a stock I’d build my portfolio around, but for a small speculative position, I see potential for outsized returns.

5. $CAKE — Boring, Profitable, and Undervalued

The Cheesecake Factory isn’t going to double overnight — and that’s exactly why I like it.

In a market obsessed with AI and growth narratives, I want exposure to businesses that just keep performing. CAKE has consistent revenue, a strong dividend, and an undervalued balance sheet. It’s a simple business with a loyal customer base and a management team that understands how to operate through cycles.

Boring companies make great compounders when bought at the right price.

6. $LMND — The Long Game in Tech-Driven Insurance

Insurance is one of the hardest industries to disrupt, but $LMND is proving that technology can change even the most traditional spaces.

The company’s revenue growth continues to climb, losses are shrinking, and efficiency is improving quarter after quarter. Lemonade’s AI-driven underwriting model is what gives it a real edge. It’s early, but the potential is massive.

If execution continues, this could be one of those stocks investors look back on in five years and realize how early they were.

7. What I’m Watching Next

Beyond my core positions, I’m keeping a close eye on a few stocks that could make their way into my portfolio soon:
$ADBE, $CRM, $NVO, $HNST, $ZETA, and $DLO.

Each has something unique — strong business models, pricing power, or long-term growth optionality. I’m waiting for the right valuations to step in.

8. The Bigger Picture

The longer I invest, the more I realize patience is the real superpower. The market constantly tempts us to react — but long-term wealth is built through staying steady.

I don’t care about timing the next correction or chasing every rally. My focus is building positions in companies I understand, trust, and believe will be worth significantly more in three to five years.

Compounding doesn’t happen overnight. It happens quietly, when you’re not watching.

Final Thoughts

October isn’t about chasing trends for me — it’s about doubling down on conviction.

I’d rather keep building exposure to quality businesses with real cash flow, strong leadership, and long-term growth ahead than try to guess the next short-term winner.

That’s what this month is about: staying consistent, patient, and focused on execution.

If you like analyzing setups like these, check out Surmount.
It’s where I dive into strategies, stocks, and charts — all in one place.
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https://surmount.ai/strategies?utm_source=newsletter&utm_medium=promo&utm_campaign=ashton

Disclosure:
This newsletter is for informational and educational purposes only. Nothing here should be taken as financial advice or a recommendation to buy or sell any security. Always do your own research and consider your individual risk tolerance before making investment decisions. I may hold positions in the stocks mentioned.

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