Most research studies going over startup failures, including my favorite CB Insights research report, cover a number of reasons related to product-market fit. I’ll use theirs as an example.
Going top-to-bottom, we see the following:
- Running out of cash/no funding validation
- Lack of market need
- Flawed business model
- Product mistimed
- Poor product
Of course, there are other reasons related to management, team structure, hiring, building sprints, working with stakeholders, sales, VC management. I don’t discard the myriad of reasons here.
But ultimately – it’s about product-market fit (or its lack of whatsoever).
Founders and product managers often resort to crowdsourced knowledge through established business leaders, their bios, and resources they’ve authored around that topic. This is only natural – studying success stories and replicating what they’ve done or how they preach founding startups.
I myself am guilty of developing the Product MVP guide years ago here as one such resource, based on my learnings as a founder (my own products/businesses) and hundreds of agency/consulting clients.
But some of the leading sources we’ve all drawn inspiration from are “The Lean Startup” by Eric Ries, “Zero to One” by Peer Thiel (ex-PayPal), “The Lean Product Playbook” by Dan Olsen, “Start. Scale. Exit. Repeat” by Colin Campbell, “The Product Book” by Product School.
And various biographies or interpretations of how different leaders such as Elon Musk, Jeff Bezos, and Bill Gates work – along with numerous essays, interviews, and recorded keynote talks by thousands of successful founders.
But the problem with entrepreneurs going through this list is simple. Entrepreneurs aim to solve PROBLEMS, and how they interpret a book is often around strategies, techniques, frameworks, blueprints, worksheets, and lesser about the bigger picture.
Studying long, deep, and hard is what we do either in the earlier college years (with no premise of paying the bills or launching a science career ASAP), near retirement, or in a blissful moment of having your life together, kids old enough, business running on autopilot – very few being in that particular spot. Everyone else is mostly looking for the key to unlocking that big Pandora’s box of launching startups the right way, hiring the right people, building the right product fast and cheap (yet of quality).
If you go over a hundred bios with the intention of capturing patterns and best practices, you may achieve partial success in that initiative. I admire newsletter authors doing bios or book summaries for a living – even as they don’t necessarily apply all that knowledge themselves, they’re in the process from a research standpoint, staying open-minded to different levers they can use.
But a key flaw in interpreting and seeking strategies in 2025 from the old books is how the market has shifted since 2023.
If you go through the “growth levers” of Hotmail, their footer link under each email has been a key hack. It may look obsolete, but others have tried that successfully since, especially for freebie products with copyrights and watermarks.
Or Airbnb scraping listings and running their own marketplace off of other items (that’s happening quite a lot, not to mention programmatic SEO knock-offs today).
Or Dropbox with referral links sharing 2 GBs and getting 2 GBs free.
All of these paradigms were designed to operate in a space that:
- Isn’t vastly crowded
- Is hard to get into (long time to develop a product/context)
- Inefficient marketing channels (easy to hack existing ones)
- A growing tech ecosystem (appetite for testing new solutions)
- A large enough pool of opportunities (a good number of real products uncovered)
Taking a look from a different perspective:
- Consumers were more inclined to test new products given the right medium of contact
- Marketing was easier (noise factor was way lower)
- Trust in communication channels was higher
- Cost of developing a knock-off was significantly higher
- Technology had a MOAT in terms of the total sum of costs (including hosting costs or data retention or others)
In 2025, we operate under a different reality.
The golden era of technology as we know it is in decline. I’m confident we’ll get a new set of “technology” glasses within building neural networks, an entire ecosystem of extensions and connectors for LLMs, robotics (a truly growing vertical), and some other flavor of voice assistants or IoTs alongside (maybe programming software for cars while we’re at it).
But web and digital is being challenged.
Desktop use outside of the workspace is in decline (and most offices put some restrictions within firewalls, if not nulling the appetite due to monitoring employee behavior).
Gen Alpha don’t pay attention to sites anymore. They look into TikTok or watch YouTube shorts or voice text their fellows. Browsing Google or scrolling through sites is an afterthought. When once we’d look for actor bios in IMDB or look up Google or Wikipedia, they check Instagram and TikTok profiles first. When we would search for restaurants or hotels on Expedia, TripAdvisor, Yelp, or Booking, they would use another superapp (a social media network often) to find recommended hotels by influencers or just what they discover in the Explore feed.
And Instagram or TikTok extensions are not equivalent to building web sites, portals, networks, marketplaces, affiliate websites. A tiny number of superapps worth tens of billions of dollars generally control the narrative, and often operated from within mobile devices on the go.
Now, that may be a “doom and gloom” prediction, and I’ve learned over time that balance is hidden between being “oblivious” to the external environment and all the conspiracy theorists. Ultimately, we’ll end up somewhere in-between.
But living in the era of AI, with teenagers operating differently with the web, with trust crowdsourced into few powers, with hundreds of products launched daily on sites like Product Hunt, crowded and oversaturated marketing space (automated robotized social bots, programmatic SEO, cold email campaigns at mass), the digital space is cluttered, trust in the web is at its lowest, and the cost to building a product is negligible.
Relying on the old playbooks that operated under a different context – with different MOATs (time to build, ease of market, appetite of the digital consumer) is a false premise if you count on strategies, not philosophies or the history of the web.
We’re not in a second dot Com boom. Treat it as one.
I’ll provide my own take on how WordPress supports that narrative of conveying trust in the web in my next post. It’s a case study of what the public sees and what data seemingly displays, but not necessarily how the ecosystem moves in practice, how decisions are made in board rooms, and what investments are being allocated there.
