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👉 CrowdStrike's $1B Share Repurchase Program

Rubrik, Tesla, Ollie's

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👉 Week in Review — Too Long; Didn’t Read:

Key Earnings Announcements:

  • CrowdStrike announced a $1B share repurchase program.

  • Rubrik delivered positive operating cash flow for the first time ($40M).

  • Ollie’s opened 25 new stores during the quarter (old Big Lots locations).

Investor Events & Global Affairs:

  • President Trump and Elon Musk blew up the internet this week.

  • Treasury Secretary Scott Bessent will meet with China in London on Monday.

  • Mark Zuckerberg plans to have Meta fully automate ad creation.

  • Circle’s IPO was a massive success — with prices sitting +264% higher than its original IPO price.

Major Economic Events:

  • The Atlanta Fed’s Q2 GDP projection rose from 3.8% to 4.6%.

  • The US added +139,000 nonfarm payroll jobs & unemployment stayed at 4.2%.

  • The ADP Employment Report revealed the weakest private sector monthly job gain in over two years.

Happy Sunday.

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👉 Portfolio Updates (YTD Performance):

The only change I’ve made to the portfolio is beefing up the allocation to the “Long Risky” subsection — which is already up +22.3% YTD (far outpacing the S&P 500’s +2.4% and the Nasdaq-100’s +3.8% YTD returns). If the Republicans are going to pass the “Big Beautiful Bill” and turbocharge all of this government spending, then high-risk growth names should continue to rise in value.

I’ll be investing ~$8,000 this month, all of which will go to the Long Risky subsection of my portfolio. I plan to publish a subscriber-exclusive update later this week on changes I’ll be making to this subsection of the portfolio soon — so stay tuned for that!

My NEOS funds are inching closer to $100K in value, which will result in well over $1,000 per month in passive income! Excited for that one.

My Bitcoin position remains the same, hovering around 1.5 BTC. No changes there.

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👉 Key Earnings Announcements:

CrowdStrike announced a $1B share repurchase program, Rubrik delivered $40M in operating cash flow, and Ollie’s opened 25 new stores.

  • CrowdStrike (CRWD)

Key Metrics

Revenue: $$1.1 billion, an increase of +20% YoY

Operating Loss: -$124.6 million, compared to $6.9 million last year

Net Loss: -$110.9 million, compared to $46.3 million last year

Earnings Release Callout

“We started the fiscal year with record Q1 large deal and MSSP momentum alongside sustained 97% gross retention and consistently strong net retention as the market consolidates on Falcon as its cybersecurity platform of choice for the agentic AI era.

The scale of Falcon Flex demand and the pace of innovation across AI, next-gen SIEM, cloud, identity, and exposure management advances us towards $10 billion in ending ARR. Today’s announced share repurchase reflects our confidence in CrowdStrike’s future and unwavering mission of stopping breaches.”

My Takeaway

Just to bring you all up to speed on one of the biggest winners in my portfolio — CrowdStrike has officially grown their annual recurring revenue to $4.5B on 77% gross profit margins. They generated $1.1B in revenue during the quarter, with $279.4 million of that categorized as free cash flow.

The company both reaffirmed their 2025 top line revenue guidance and raised their bottom line profit guidance as they expect continued momentum throughout the coming year. Operating income for the calendar year is expected to be around $975M, as management looks to balance aggressive investments into the existing platform while leveraging AI to accelerate their execution, efficiency, and go-to-market strategies to scale further toward that $10B ARR goal of theirs.

Their free cash margin of 25% this quarter, compared to 23% last year’s quarter, reflects their ability to scale efficiently. Their remaining performance obligations (future revenue) grew +45% to $6.8B due to accelerated deal momentum for Falcon Flex. Finally, the company announced a $1B share repurchase program — further solidifying their long-term commitment to providing shareholder value.

In my opinion, CrowdStrike remains the gold standard for cybersecurity. The company remains in the early innings of its multi-year growth story as the company continues to take strategic steps to integrate AI across their portfolio.

Long CRWD!

  • Rubrik (RBRK)

Key Metrics

Revenue: $265.6 million, an increase of +54% YoY

Operating Loss: -$93.1 million, compared to -$724.8 million last year

Net Loss: -$102.1 million, compared to -$732.1 million last year

Earnings Release Callout

“Our outstanding first-quarter results not only surpassed all guided metrics but also underscore the power of our focused innovation and execution. We are winning the cyber resilience market, and I believe that our opportunity is bigger than ever. Q1 was a strong start to our second fiscal year as a public company, with another quarter of solid top-line growth at scale and continued improvement towards profitability.”

My Takeaway

That last sentence in their earnings release is the key — read it again: “continued improvement toward profitability.”

My absolute favorite trade is owning a stock 12-18 months before they become profitable. Buying a stock when they’re still burning cash, holding it for a year or two until they’re profitable, then watching their stock price 2-5X in value over the coming years because of it is an incredible strategy. Monday, CrowdStrike, Hims & Hers Health, and countless other names in my portfolio have been this exact strategy.

It’s one of the easiest investment of all time, in my humble opinion. And Rubrik is shaping up to be exactly that!

The company delivered another strong quarter, with Subscription annual recurring revenue growing +38% to $1.2B at a 78% gross profit margin. Their Subscription contribution margin also increased +18.6% to positive 8.0% (up from -10.6% last year’s quarter). The company’s cash flow from operations also came in positive during the quarter, $39.7M compared to last year’s quarter of -$37.1M.

The company provided guidance for 2025 and it didn’t disappoint! Subscription ARR around $1.4B, a 6.0% contribution margin, and free cash flow of $70M. The exciting part is to reflect upon Wall Street’s expectations for 2026 — free cash flow growth of +110% to $150M, and breakeven adj. EBITDA. This company is half a decade away from $500-750M in annual free cash flow.

At $100 / share, this company is exciting to me. This reflects an $18B market cap, or about 12X forward revenue. Eager to add this one to my “Long Risky” subsection of the portfolio to complement my CrowdStrike position.

  • Ollie’s Bargain Hunt Outlet (OLLI)

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