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Kevin Rose29 August 2021

Kevin Rose from Web 2.0 to Web3

3Frameworks
13Insights

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Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 2

Myth Buster

Correcting Digg's Real Founding Story

Kevin corrects widely-repeated Digg lore: it wasn't lunch with Woz, and Jay Adelson and Ron weren't co-founders — the real spark was Slashdot's Commander Taco rejecting his idea.

  • Wikipedia and press accounts of Digg's founding are inaccurate per Kevin
  • Commander Taco declined to let users see all Slashdot submissions, prompting Kevin to build Digg himself
  • Jay Adelson was hired as CEO months later, not a co-founder from day one

“There is so many different lore stories, or there was even Wikipedia is completely wrong.”

Kevin Rose

“why don't you make it so we can see all the submissions and then we can like vote up the best ones?”

Kevin Rose
#Digg#founding story#Slashdot#Jay Adelson
Myth Buster

The Canvas Painting Backlash as an NFT Parallel

Kevin recounts how the invention of portable canvas paintings once faced skepticism versus permanent frescoes — a historical parallel to today's NFT doubters.

  • Early canvas art was distrusted for being portable rather than permanent
  • Canvas pieces were initially valued less than wall/wood-based art
  • Kevin sees the same adoption curve playing out with NFTs today

“many people thought during that time it's portable. Why wouldn't you want something permanent?”

Kevin Rose

“a lot of Canvas art was actually worth less than things that were actually in a more permanent, you know, on the wood or on…”

Kevin Rose
#NFT skepticism#art history#canvas#adoption curve

Hot Take· 1

Hot Take

Digital Natives Value Their Online Identity More Than Real Life

Kevin cites a survey showing a majority of gamers rank their online identity above their offline identity, explaining generational readiness for NFT ownership.

  • A cited survey found over 50% of gamers value online identity more than offline identity
  • Younger generations are used to owning and purchasing virtual goods (skins, items)
  • This generational shift underpins mainstream NFT adoption potential

“there is a very large subset of gamers that consider it was like more than 50%.”

Kevin Rose

“They consider their online identity in their games to be more important than their offline, like in person identity.”

Kevin Rose
#gaming#digital identity#NFT adoption#generational shift

Explainer· 2

Explainer

How the Term 'Web 2.0' Got Applied to Digg

Kevin didn't know he was running a 'Web 2.0' company until Jason Calacanis told him during a lunch meeting, illustrating how insiders rarely name their own movements.

  • Kevin had never heard the term 'Web 2.0' before Calacanis used it
  • He jokingly wondered if it required a server software upgrade
  • The pattern repeats across tech history — insiders build the thing before it gets named

“he was like, You're like one of the biggest web 2.0 companies. And like literally, I thought, is there a software I need to upgrade…”

Kevin Rose
#Web 2.0#naming#Jason Calacanis
Explainer

Why Dogecoin Started With a Real Purpose

Kevin explains Dogecoin's original design as a Reddit tipping currency with a deliberately huge supply to discourage hoarding, contrasting it with later copycat meme coins.

  • Dogecoin was designed for tipping/rewarding good deeds on Reddit
  • Its large supply was intentional, to prevent hoarding and encourage circulation
  • Kevin distinguishes genuine community projects from price-driven clones

“It was meant to be a cryptocurrency that could be used as a way to more or less give away for good deeds.”

Kevin Rose
#Dogecoin#meme coins#crypto history

Story· 6

Story

Sneaking Into Comdex as a Teenage Super-Fan

Kevin describes faking a business name to get into Comdex badges as a teen in Vegas, which is how he first realized Silicon Valley existed as a tech hub.

  • Kevin grew up in Las Vegas and got into computers via BBSes and magazines
  • He invented a fake company ('Foliage Software') to get a free Comdex badge as a minor
  • Walking the Comdex floor showed him that nearly all the exhibiting tech companies were based in Silicon Valley

“So I just made up a fake business name. I called it Foliage Software.”

Kevin Rose

“that's how I realized that all these companies were not based here. They were based, you know, most of them were kind of California Silicon…”

Kevin Rose
#origin story#Silicon Valley#Comdex#Las Vegas
Story

From Behind-the-Scenes Geek to TechTV's 'Dark Tipper'

Kevin explains how discovering a Windows messaging vulnerability got him pulled on-camera at TechTV, eventually earning him the 'Dark Tipper' nickname.

  • Kevin originally wanted to work behind the scenes, not on camera
  • A Windows spam vulnerability he found became his on-air debut topic
  • The producer asked him to keep finding obscure tools/hacks, leading to the recurring 'dark tips' segment

“I had discovered a vulnerability in Windows that was a way to spam people using this kind of uh internal messaging tool.”

Kevin Rose

“they call me the dark tipper as a joke, and then it just kind of like was a funny little thing on the on the…”

Kevin Rose
#TechTV#Screensavers#career origin#biography
Story

Mark Zuckerberg's Visit Before the Facebook Like Button

Kevin recounts Mark Zuckerberg visiting Digg's San Francisco office pre-News Feed to discuss voting mechanics, before Facebook had built the Like button.

  • A Greylock board connection introduced Kevin and Zuckerberg
  • Zuckerberg was interested in how Digg's voting fed its recommendation algorithm
  • Facebook later invited Digg into its early developer platform

“he's like, hey, let's, you know, I'll come to the city because he was down in Palo Alto, and he's like, I'll come to SF…”

Kevin Rose

“he was very curious, and yeah, it was nice. It was like Mark was a nice guy.”

Kevin Rose
#Facebook#Mark Zuckerberg#Digg button#Like button history
Story

Dignation at SXSW and Bringing His Dad

A live Dignation taping at SXSW drew thousands of fans, and Kevin flew his father out for the show shortly before his father's passing.

  • Kevin and Alex were shocked by the size of the crowd at the live show
  • Fans followed Kevin for autographs afterward, surprising his father
  • His dad passed away two years later, making the memory especially meaningful

“We had no idea that that many people would show up.”

Kevin Rose

“it was a special moment for me because we didn't have a whole lot growing up, and my dad was really proud.”

Kevin Rose
#SXSW#Dignation#personal story#family
Story

How Kevin Missed Investing in Coinbase Through Corporate VC

Kevin tried to get Google Ventures to back Coinbase early after meeting Brian Armstrong, but a partner's 'tulips' skepticism blocked the corporate deal — so he invested personally instead.

  • Kevin discovered Bitcoin/Coinbase around 2011-2012, verified via old emails
  • A Google Ventures partner compared Bitcoin to tulip mania, wary of reputational risk to Google
  • Kevin later invested in Coinbase personally rather than through the fund

“Called it tulips and basically said that you know, we can't the the fear, and and this is a valid fear back then.”

Kevin Rose

“I ended up investing in in Coinbase a little bit later personally.”

Kevin Rose
#Coinbase#Google Ventures#corporate venture#Bitcoin history
Story

How a Twitter Suggested-Users Hack Led Kevin to His Wife

Chris Sacca asked Evan Williams to manually add Kevin to Twitter's early suggested-users list at a bar, which indirectly led to Kevin meeting his future wife via a retweet.

  • Ev Williams manually added Kevin to Twitter's hard-coded suggested user list at a bar
  • The addition caused an instant flood of new followers
  • A retweet from a follower later became a connection with Kevin's now-wife, Daria

“he pulls out his phone and he literally does it right there on his phone. And he's like, Okay, done.”

Kevin Rose

“it was all because Ev added me to the suggested user list.”

Kevin Rose
#Twitter history#Evan Williams#personal story#suggested user list

Q&A· 1

Q&A

Launching Proof: A Dedicated NFT-Only Podcast

Kevin announces splitting his NFT-focused content into a new podcast, Proof, while keeping Modern Finance focused on DeFi and broader crypto topics.

  • Modern Finance listeners were split between wanting more NFT content and more DeFi/crypto content
  • Proof (proof.xyz) will go deep on NFT art, generative art, DAOs, and gaming assets
  • Big-name NFT interviews will still cross-post to the main Modern Finance feed

“I'm actually going to be launching a new podcast, if I don't already have enough podcasts, that is dedicated to all things NFTs.”

Kevin Rose

“I can't please everybody, so I got I gotta break it.”

Kevin Rose
#Proof podcast#Modern Finance#NFT media#podcast strategy

Takeaway· 1

Takeaway

Why Kevin Chose True Ventures' Long-Term Philosophy

Kevin explains what drew him to join True Ventures full-time: their patient, founder-first approach that removes pressure to force exits or IPOs.

  • True Ventures backed multiple of Kevin's companies (Milk, Hodinkee, Zero) before he joined as a partner
  • The firm avoids pushing entrepreneurs toward forced sales or IPOs
  • Kevin transitioned from venture partner to full-time partner after having his first child and wanting more stability

“we pride ourselves in trying to take as all the pressure off the entrepreneur.”

Kevin Rose

“Kevin, this is your company. Do whatever you want, man.”

#True Ventures#venture capital#career transition