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Matan’s Blog

I try to go to bed a little bit smarter than when I woke up. Tech, Finance, and other topics.

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Google: LLM Frontier Over AGI Dreams

Losing its top researchers looks like a crisis for Google. But it was probably a necessity, and it's bullish for Gemini.

How To Achieve Failure: A New Mission For This Blog

As I look back at the posts I published around here, a clear theme emerges. One that aligns well with a classic Charlie Munger advice.

What Happened to Stitch Fix? Part 3: Freestyle Freefall

When the Freestyle bet failed, Stitch Fix retreated to the Fix business — only to find it had damaged its core business in its ambitious pursuit.

What Happened to Stitch Fix? Part 2: More Than A Bold Bet

Stitch Fix is getting a new CEO and a grand new ambition. In the process, it is also losing the discipline its founder instilled.

What Happened to Stitch Fix? Part 1: From Profitable Niche to $100B Disruption Dreams

While the rise of Stitch Fix was well documented, its fall was largely ignored. Dismissed as another post-Covid e-commerce flameout. It's a shame, because the story carries useful lessons. Part 1.

How Inflation Saved Wealthfront, And Could The Windfall Turn Into A Durable Business?

While most fintech companies were hit hard by the end of ZIRP, rising interest rates turned out to be a boon for Wealthfront. Could it be built into a sustainable business?

Could Anthropic Commoditize the Cloud?

Many interpreted reports on Microsoft dropping Claude Code as doubts about AI coding. But this is wrong. Agentic coding works too well, to the extent that it might threaten the major clouds.

Could Nadav Zafrir Accelerate Check Point's Growth?

When Check Point chose a startups guy to replace Gil Shwed, investors hoped for him to shake things up at the sleepy company and accelerate growth. This isn't happening so far, and might never will.

“Horrendous Investment By Your Chairman”: Fairfax's Bet On BlackBerry

Prem Watsa is often called "Canada's Warren Buffett." His investment in BlackBerry closely parallels actual-Buffett's mistake of investing in Berkshire Hathaway, and carries the same lesson.

The Turnaround Trap: When the Moat Dries Up

A decades-old lesson from Warren Buffett, that investors seem to keep ignoring.

The Mainframe Paradox

The mainframe survived the web and the smartphone, and even grew because of them. What about AI?

Gemini For Mac Doesn't Seem Like A Big Deal, But It Could Be

Google rarely builds desktop apps, but finally relented and launched one for Gemini. Just a me-too product for now, but it could represent a much bigger opportunity than it looks.

Sold Out: Eventbrite and the Marketplace Trap

Covid didn't kill Eventbrite. But a single strategic misstep unraveled its admirable post-pandemic rebuild.

What If Shopify Isn't An AI Winner?

The internet - including Shopify's success story - shows that new tech paradigms develop in surprising ways. Incumbents might not adapt, and premature predictions about the winners might fail.

Monday's Retreat

Monday.com's recent strategy shift offers a fascinating peek into a disruption story that may be unfolding in real-time.

Excel Obsoletion

Microsoft Excel remained the world's most popular programming language throughout the Cloud and Mobile eras; with AI, however, English may assume that role, rendering spreadsheet software obsolete.

Matan's Blog 2025 Year In Review

Looking back at my first year writing this blog.

Bolting AI vs Reimagining: Is OpenAI Netscape Or Google

Sam Altman on bolting AI onto existing services vs. reimagining them with AI, Google's reimagining and Chrome displacing Internet Explorer, ChatGPT Atlas, Google Disco, and Netscape's cautionary tale

Is Lyft In Denial About Robotaxis?

Lyft doesn't seem paranoid about self-driving robotaxis. Latest CEO comments echo Steve Ballmer's iPhone-era vibes.

Could Wix Successfully Disrupt Itself?

On Vibe Coding, the Base44 acquisition, and how despite ongoing skepticism, Wix is determined not to be killed by AI but rather benefit from it.