Rob's Notes 20: The Biggest Tech Fails (2000-2025)

My social media tech friends have produced a fascinating list

I asked all of you for your suggestion of “the biggest screw up in the last 25 years of tech history (since 2000)” on LinkedIn, Threads and Twitter, and boy did you deliver a great list of responses! The list says a lot about what us tech people ourselves find interesting, and we’ll certainly be adding to this list in the coming months and years.

Cultural and strategic blind spots show up repeatedly for various tech giants across the decades. Many of us who’ve been around so much innovation probably relate to the “great idea/team/momentum, bad execution/follow-through” patterns and call these out, as well as other situations where promising projects people loved lacked needed community or developer support, and flopped as a result.

This list also reminds me of how young (and ethically immature) our tech industry still is… BUT that said, I have always been glad to work in an industry whose participants are still willing to publicly call attention to its gaps and lapses. The biggest fail would be if we stopped doing that, and didn’t seek to learn from our numerous mistakes.

Here’s a summary of what you said on the socials:

Social media:

• Google+ – Poor execution and failure to gain traction in social media

• Facebook’s Cambridge Analytica scandal – Deeply damaging to user trust

• Twitter selling to Elon Musk – Commonly cited as a cultural and strategic disaster

• Twitter deprecating Vine – Allowed TikTok to dominate

• Snap mismanaging growth – when a strong product doesn’t monetize as well

• Yahoo acquiring Tumblr - with little to no follow-through

Phones and platform shifts:

• Meta not launching a phone (Zuck’s abandoned plans) – Missed hardware opportunity

• Amazon Fire Phone – Market flop with little hope from inception

• Microsoft ditching Windows Phone – Repeatedly called a major missed opportunity

• RIM / Blackberry: Clinging to physical keyboards and ignoring touchscreen trends

• Nokia: Refusing to adapt (clinging to Symbian OS), making S60 SDKs developer-unfriendly

• Form factor shifts – Google Glass, HoloLens, Magic Leap: tech ahead of its time or mispackaged

Content:

• Quibi – Massive investment with no product-market fit

• Google killing Google Reader – Alienated loyal users, with some lamenting the shift toward algorithmic feeds

• Microsoft - failing to get a YouTube or Pokémon Go app for Windows

• Comment sections on news websites – Which have encouraged toxic discourse

Bad M&A or No M&A:

• Yahoo not buying Google - and letting its product suite (Flickr, Messenger, etc.) stagnate

• Microsoft buying Skype - then ruining the experience

• Groupon refusing Google's acquisition offer – Lost exit opportunity

• AOL buying Time Warner – Hugely destructive merger

• HP buying Autonomy – One of the worst enterprise deals of all time

• AT&T buying DirecTV / Time Warner Media – Poorly timed and executed

Missed Deals and Missing Products:

• Intel declining Apple’s ARM chip deal - now geopolitically significant, and missing GPU innovation

• Electric Vehicles: GM killing the EV1 and Nissan/Toyota missing early EV market dominance

• Streaming – Blockbuster and Redbox failing to adapt

• WeWork, Webvan, scooter companies – Mismanaged capital-heavy startups

• Netscape + QuarkXPress – Missed partnership opportunities in early web

Policy, Ecosystem, and Industry-Wide Issues:

• Section 230 of the Communications Decency Act – This is always a fun one. Opinions are divided

• Cryptocurrency / NFTs – Massive value loss, scams, and volatility

• Surveillance capitalism – Systemic privacy and trust issues

• PRISM / Patriot Act – Institutional surveillance backlash

• Letting founders become untouchable icons – Reduced accountability

• Tech industry avoiding early regulation – Led to long-term harm

• Defunding arts/humanities in favor of STEM-only focus – Cultural critique

• Lack of digital literacy in schools – People learned to use, not understand, tech

• Failure to include ethical and civic literacy in tech – Contributed to mistrust and exclusion

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I will write more about this topic in general and about some of these failures in particular. I want to hear from people with first-hand experiences they want to / are able to share.

I hope you’ll let me know via email or social media what you think of this list, and what we missed!