Brian McCullough, who runs Internet History Podcast, also wrote a book named How The Internet Happened: From Netscape to the iPhone which did a fantastic job of capturing the ethos of the early web and telling the backstory of so many people & projects behind it's evolution.

I think the quote which best the magic of the early web is

Jim Clark came from the world of machines and hardware, where development schedules were measured in years—even decades—and where “doing a startup” meant factories, manufacturing, inventory, shipping schedules and the like. But the Mosaic team had stumbled upon something simpler. They had discovered that you could dream up a product, code it, release it to the ether and change the world overnight. Thanks to the Internet, users could download your product, give you feedback on it, and you could release an update, all in the same day. In the web world, development schedules could be measured in weeks.

The part I bolded in the above quote from the book really captures the magic of the Internet & what pulled so many people toward the early web.

The current web - dominated by never-ending feeds & a variety of closed silos - is a big shift from the early days of web comics & other underground cool stuff people created & shared because they thought it was neat.

Many established players missed the actual direction of the web by trying to create something more akin to the web of today before the infrastructure could support it. Many of the "big things" driving web adoption relied heavily on chance luck - combined with a lot of hard work & a willingness to be responsive to feedback & data.

• Even when Marc Andreessen moved to the valley he thought he was late and he had "missed the whole thing," but he saw the relentless growth of the web & decided making another web browser was the play that made sense at the time.
• Tim Berners-Lee was dismayed when Andreessen's web browser enabled embedded image support in web documents.
• Early Amazon review features were originally for editorial content from Amazon itself. Bezos originally wanted to launch a broad-based Amazon like it is today, but realized it would be too capital intensive & focused on books off the start so he could sell a known commodity with a long tail. Amazon was initially built off leveraging 2 book distributors ( Ingram and Baker & Taylor) & R. R. Bowker's Books In Print catalog. They also did clever hacks to meet minimum order requirements like ordering out of stock books as part of their order, so they could only order what customers had purchased.
  

  Amazon employees:
  
  2018 647,500
  2017 566,000
  2016 341,400
  2015 230,800
  2014 154,100
  2013 117,300
  2012 88,400
  2011 56,200
  2010 33,700
  2009 24,300
  2008 20,700
  2007 17,000
  2006 13,900
  2005 12,000
  2004 9000
  2003 7800
  2002 7500
  2001 7800
  2000 9000
  1999 7600
  1998 2100
  1997 614
  1996 158— Jon Erlichman (@JonErlichman) April 8, 2019

• eBay began as an /aw/ subfolder on the eBay domain name which was hosted on a residential internet connection. Pierre Omidyar coded the auction service over labor day weekend in 1995. The domain had other sections focused on topics like ebola. It was switched from AuctionWeb to a stand alone site only after the ISP started charging for a business line. It had no formal Paypal integration or anything like that, rather when listings started to charge a commission, merchants would mail physical checks in to pay for the platform share of their sales. Beanie Babies also helped skyrocket platform usage.
• The reason AOL carpet bombed the United States with CDs - at their peak half of all CDs produced were AOL CDs - was their initial response rate was around 10%, a crazy number for untargeted direct mail.
• Priceline was lucky to have survived the bubble as their idea was to spread broadly across other categories beyond travel & they were losing about $30 per airline ticket sold.
• The broader web bubble left behind valuable infrastructure like unused fiber to fuel continued growth long after the bubble popped. The dot com bubble was possible in part because there was a secular bull market in bonds stemming back to the early 1980s & falling debt service payments increased financial leverage and company valuations.
• TED members hissed at Bill Gross when he unveiled GoTo.com, which ranked "search" results based on advertiser bids.
• Excite turned down offering the Google founders $1.6 million for the PageRank technology in part because Larry Page insisted to Excite CEO George Bell ‘If we come to work for Excite, you need to rip out all the Excite technology and replace it with [our] search.’ And, ultimately, that’s—in my recollection—where the deal fell apart.”
• Steve Jobs initially disliked the multi-touch technology that mobile would rely on, one of the early iPhone prototypes had the iPod clickwheel, and Apple was against offering an app store in any form. Steve Jobs so loathed his interactions with the record labels that he did not want to build a phone & first licensed iTunes to Motorola, where they made the horrible ROKR phone. He only ended up building a phone after Cingular / AT&T begged him to.
• Wikipedia was originally launched as a back up feeder site that was to feed into Nupedia.
• Even after Facebook had strong traction, Marc Zuckerberg kept working on other projects like a file sharing service. Facebook's news feed was publicly hated based on the complaints, but it almost instantly led to a doubling of usage of the site so they never dumped it. After spreading from college to college Facebook struggled to expand ad other businesses & opening registration up to all was a hail mary move to see if it would rekindle growth instead of selling to Yahoo! for a billion dollars.

The book offers a lot of color to many important web related companies.

And many companies which were only briefly mentioned also ran into the same sort of lucky breaks the above companies did. Paypal was heavily reliant on eBay for initial distribution, but even that was something they initially tried to block until it became so obvious they stopped fighting it:

“At some point I sort of quit trying to stop the EBay users and mostly focused on figuring out how to not lose money,” Levchin recalls. ... In the late 2000s, almost a decade after it first went public, PayPal was drifting toward obsolescence and consistently alienating the small businesses that paid it to handle their online checkout. Much of the company’s code was being written offshore to cut costs, and the best programmers and designers had fled the company. ... PayPal’s conversion rate is lights-out: Eighty-nine percent of the time a customer gets to its checkout page, he makes the purchase. For other online credit and debit card transactions, that number sits at about 50 percent.

Here is a podcast interview of Brian McCullough by Chris Dixon.

How The Internet Happened: From Netscape to the iPhone is a great book well worth a read for anyone interested in the web.