Smart and Successful People Missed The Internet in The '90's
Executive Summary
A six-minute clip from The Tim Ferriss Show in which investor Kevin Ryan, founder of AlleyCorp and former CEO of DoubleClick, recalls how he spotted the early internet in the mid-1990s. He describes working in finance and at Euro Disney, becoming an executive at United Media, launching the Dilbert website in 1995, pricing the first ad on the spot, and being told by a senior executive to wait for the next internet. He then explains joining DoubleClick early, rising to CEO, deciding fast, and expanding to 20 countries before the first was profitable. Sponsors named in the description: Eight Sleep, Shopify and Momentous (AG1 is also listed). PARTIAL COVERAGE: this is a short clip taken from a longer conversation, and this note covers the whole clip but not the full episode it comes from. Claims are the guest's own account and are not independently checked. Nothing here is financial advice.
Key Takeaways
Early career steps
The guest lists finance, banking and Euro Disney, where he helped launch a resort with about 15,000 hotel rooms, before deciding to leave large companies.
Spotting the internet
He says he read a Business Week article on the internet in the mid-1990s and found it incredibly cool.
The Dilbert website
The guest says he launched the site in 1995 when the company owned the comic, and it got big traffic from tech users.
Pricing the first ad
He says IBM took the first hardcoded ad for two weeks at a price he made up on the spot.
Told to wait
The guest says his boss refused funding and said to wait for the next internet, which convinced him it was time to leave.
Joining DoubleClick
He says he joined as about the 10th or 12th person and rose from CFO to president to CEO.
Decide fast, take risks
The guest says speed in decisions and global expansion, 25 offices in three years, helped them dominate their space.
The Conversation Breakdown
Early career steps
⏱ Untimed topicThe guest lists finance, banking and Euro Disney, where he helped launch a resort with about 15,000 hotel rooms, before deciding to leave large companies.
Spotting the internet
⏱ Untimed topicHe says he read a Business Week article on the internet in the mid-1990s and found it incredibly cool.
The Dilbert website
⏱ Untimed topicThe guest says he launched the site in 1995 when the company owned the comic, and it got big traffic from tech users.
Pricing the first ad
⏱ Untimed topicHe says IBM took the first hardcoded ad for two weeks at a price he made up on the spot.
Told to wait
⏱ Untimed topicThe guest says his boss refused funding and said to wait for the next internet, which convinced him it was time to leave.
Joining DoubleClick
⏱ Untimed topicHe says he joined as about the 10th or 12th person and rose from CFO to president to CEO.
Decide fast, take risks
⏱ Untimed topicThe guest says speed in decisions and global expansion, 25 offices in three years, helped them dominate their space.
Core Frameworks & Ideas
Obvious use cases - the guest's reason for conviction
He looked at what people were already doing online, buying, mapping and sharing, and saw it would grow.
Decide faster than others - the guest's edge
Quick decisions helped win large global clients, which then pulled in smaller ones.
Build the thesis, then act - the guest's path
He believed his thesis enough to leave a stable job to pursue it.
Actionable Next Steps
- ✓Look for a trend where people are already changing behavior and ask what that implies in five years.
- ✓Practice making smaller decisions faster and review how they turn out.
- ✓Check the guest's company and valuation claims as his own account.
- ✓Treat any investing remarks as the guest's views and not as financial advice.
Notable Quotes
“There is no next internet.”
“I felt like a founder.”
“you have to make your decisions faster than other people”
The One Thing to Remember
The guest argues that he spotted the internet's potential early because the use cases were already obvious, and that fast decisions and willingness to take risks let DoubleClick lead its market.