Kevin Rose from Web 2.0 to Web3

Summary Notes


In this engaging episode of Acquired, hosts Ben Gilbert and David Rosenthal are joined by Kevin Rose, a trailblazer of Web 2.0 and early investor in tech giants like Twitter, Facebook, and Square. As a partner at True Ventures and host of the Modern Finance podcast, Kevin reflects on his journey from founding Digg to becoming a prominent figure in Silicon Valley's investment scene. The conversation delves into Kevin's role in pioneering podcast networks with Revision3, his insights on the rise of cryptocurrencies and NFTs, and his commitment to producing content that demystifies the hype around emerging technologies. The episode also touches on Kevin's personal anecdotes, including how a Twitter suggestion from Evan Williams led to meeting his wife, and his future endeavors with Proof, a new podcast dedicated to NFTs.

Summary Notes

Introduction to Acquired Podcast with Kevin Rose

  • Kevin Rose is recognized for his role in the Web 2.0 movement, founding Digg, and being an early investor in several successful tech companies.
  • Currently, he is a partner at True Ventures and hosts the Modern Finance podcast.
  • The podcast episode will delve into his experiences and insights from the Web 2.0 era to the present Web 3.0 and crypto trends.

"Today, we're sitting down with Kevin Rose. Kevin was one of the pioneers of Web 20 as the founder of Dig and then became one of the Valley's first super angels, investing early in companies like Twitter, Facebook, and Square. Today, he's a partner at True Ventures and hosts of the modern finance podcast."

This quote introduces Kevin Rose, highlighting his significant contributions to the tech industry both as an entrepreneur and investor. His background sets the stage for an in-depth discussion about the evolution of the web and investment landscape.

Kevin Rose's Early Interest in Computers and Technology

  • Kevin Rose's interest in technology began early, leading him to attend Comdex, the world's largest computer convention, as a teenager.
  • He learned about the tech industry by reading computer magazines and attending tech conventions.
  • Rose's initial exposure to the tech world was through bulletin board systems and his attendance at Comdex, which he accessed by creating a fake business.

"And so I was like, oh, I've got to go to this Comdex thing, right?"

Kevin Rose's determination to attend Comdex reflects his early passion for technology and his proactive approach in immersing himself in the industry.

Transition to Silicon Valley and TechTV

  • Kevin Rose moved to the Bay Area to work in digital marketing for an online furniture retailer before joining TechTV.
  • His break into on-air talent came after discovering a Windows vulnerability and discussing it on TechTV.
  • Rose's tenure at TechTV was marked by a rapid learning curve and the development of his on-camera presence, facilitated by a talent coach.

"But the problem with tech tv is that we weren't as a network really making that much money."

This quote explains the financial challenges faced by TechTV, which eventually led to its acquisition by G4 and the subsequent changes that prompted Rose to pursue other opportunities.

Founding Digg and Revision3

  • After leaving G4, Kevin Rose founded Digg and Revision3, focusing on creating content for tech enthusiasts.
  • Revision3 was started before the term "podcast" was popularized, and it aimed to distribute video content for niche audiences.
  • The success of Revision3 was based on the realization that there was a significant audience for specialized content online.

"So for me, the kind of writing was on the wall that I needed to go do something else, know, hopefully get back to the Bay Area."

Kevin Rose recognized the need to pivot from traditional media to the burgeoning online space, leading to the creation of Digg and Revision3, which catered to the interests of tech-savvy viewers.

Evolution from Web 2.0 to Web 3.0

  • The podcast episode will explore the transition from Web 2.0, characterized by social media and user-generated content, to Web 3.0, which involves blockchain and crypto technologies.
  • Kevin Rose's experiences and insights are expected to provide valuable lessons on how the principles from the Web 2.0 era can be applied to the emerging Web 3.0 landscape.

"We start in web two and we end in web three. And obviously, Kevin is super deep on all things crypto, blockchain, NFts..."

This quote sets the stage for discussing the evolution of the web, with Kevin Rose's deep understanding of both the Web 2.0 and Web 3.0 eras serving as a foundation for the conversation.

The Role of Pilot and the Creator Economy

  • Pilot is highlighted as a vital service for startups, offering accounting, tax, and CFO services, emphasizing the importance of focusing on core business aspects.
  • The discussion touches on the creator economy and how the Internet has opened up direct channels for creators to reach their audiences.

"Pilot is the one team for all of your company's accounting, tax and bookkeeping needs..."

The mention of Pilot underscores the podcast's theme of leveraging specialized services to enhance business efficiency, paralleling the way creators use online platforms to directly engage with their audience.

Disclaimer and Community Engagement

  • The hosts remind listeners that the podcast is for entertainment and informational purposes only and not investment advice.
  • They encourage listeners to join the Acquired Slack community to engage with nearly 10,000 members interested in technology and business.

"This is not investment advice from either us or Kevin. Do your own research."

This quote serves as a standard disclaimer, emphasizing the podcast's educational and entertainment value while urging listeners to conduct their own due diligence when it comes to investments.

Kevin Rose's Reflections on TechTV and Early Career

  • Rose's experience on TechTV was formative, and he reflects on the close-knit community and creative environment there.
  • The acquisition of TechTV by G4 marked a turning point in his career, leading him to pursue entrepreneurial ventures.

"It was a really special place. The majority of people were in their twenty s that kind of like were around the set and hanging out, and we would all just party with each other afterwards and go out."

This quote captures the camaraderie and unique culture of TechTV, which played a significant role in shaping Kevin Rose's career trajectory and approach to content creation.

Emergence of Revision3 and Online Media Distribution

  • Revision3 was created as an alternative to traditional TV network distribution, leveraging the internet to share content.
  • It was sold to Discovery Networks for $35 million, a significant deal at the time, and became their digital arm.
  • The transition represented a shift from traditional to digital media for Discovery Networks.

"ld talk to each other and use the Internet to kind of share that this type of content was out there, we didn't have to rely upon these distribution agreements of these big old school television networks to get viewership, and we could actually measure it in a much more accurate way. And so that's what kind of started revision three. And, yeah, that went on for many years and actually had a great outcome. It was sold to discovery networks for 35 million."

The quote explains the rationale behind starting Revision3, emphasizing the independence from traditional TV network agreements and the ability to accurately measure viewership online. It also mentions the successful sale to Discovery Networks.

The Flywheel Effect of Media Streams and Dig Nation

  • Kevin Rose discussed the creation of Dig Nation as a means to engage with the community of the website Dig.
  • The show leveraged the existing fan base and provided a platform to discuss geeky news and stories.
  • Dig Nation contributed to increased usage of Dig by featuring community members and their submissions.
  • Dig eventually outgrew Dig Nation, with a much larger audience.

"And so at what point did you realize the flywheel effect of having a media stream with dig nation and other ways that you were reaching people and being the founder of Dig, like having this web 20 property?"

The quote addresses the realization of the reinforcing cycle where media streams like Dig Nation helped to grow the Dig website's user base, creating a flywheel effect.

The Growth and Impact of Dig

  • Dig reached a peak of 38 million monthly uniques, becoming a top ten web property.
  • Kevin Rose reflects on the growth and impact of Dig, comparing its reach to the current scale of platforms like Facebook.

"Dig was reaching, I think. What did it cap out at like 38 million monthly uniques?"

The quote highlights the significant reach of Dig at its peak, emphasizing its status as a major web property.

The Influence of Dig on Facebook's 'Like' Button

  • Mark Zuckerberg visited Kevin Rose to discuss the dig button, which influenced Facebook's development of the 'like' button.
  • Dig had a common investor with Facebook, which facilitated the introduction between Kevin and Mark.
  • The meeting focused on the benefits of content voting and recommendations, which were integral to Dig's platform and later inspired Facebook's features.

"So we had a common investor, Greylock, and David Z, who was at Greylock, who's on our board and also on the board of Facebook was like, hey, you guys should get together and did an email introduction."

The quote explains the connection between Dig and Facebook through a mutual investor and how it led to a meeting that influenced Facebook's development of the 'like' button.

Misconceptions About the Origin of Dig

  • There are many false stories about the inspiration behind Dig.
  • The true origin involved Delicious, a social bookmarking site, and a conversation with Commander Taco from Slashdot.
  • Kevin Rose clarified the founding story of Dig, dispelling myths and incorrect information found in media and on Wikipedia.

"So basically what happened is there was a site out there called Delicious that was created by Joshua Schachter that was all about social bookmarking."

This quote provides the actual inspiration behind Dig, which was influenced by the social bookmarking site Delicious and a desire to apply its concept more broadly.

The Web 2.0 Era and Its Culture

  • Kevin Rose discusses the early days of the Web 2.0 era, a time of close-knit community and collaboration among tech entrepreneurs.
  • The term "Web 2.0" was not well understood initially, but it came to represent a new era of dynamic content and social media.
  • The Web 2.0 era was characterized by a spirit of genuine information sharing and belief in a common purpose.

"You're one of the biggest Web 2.0 companies."

The quote reflects the recognition of Dig as a significant player in the Web 2.0 era, even though the term was not initially understood by its founder.

The Transition to Web 3 and Similarities to Early Web 2.0

  • Kevin Rose feels that the current excitement around Web 3 is similar to the early days of Web 2.0, with a sense of camaraderie and belief in the technology.
  • Web 3, like Web 2.0, is not yet fully embraced by the mainstream but holds promise for the future.

"It does, yeah. I would say this is the first time since Web two where I've felt that type of connection and camaraderie around a new technology that the mainstream has yet to embrace, is starting to embrace, but is yet to embrace."

The quote captures Kevin's sentiment that the early stages of Web 3 evoke similar feelings of community and anticipation as the Web 2.0 era did.

Skepticism and Excitement in Emerging Technologies

  • Early skepticism about social networks and web 3 mirrors current doubts about the legitimacy and scalability of crypto and NFTs.
  • There is excitement in believing in a technology early on, even when others are doubtful.
  • The speaker enjoys the thrill of seeing potential in something that is not yet widely accepted.

"What are these social network things about? Am I really going to show people what I'm into by voting on things? There was a lot of just, I don't know that I believe this to be true. And that's the same thing that's happening in web three now."

The quote reveals a parallel between past doubts about social networks and current doubts about web 3, highlighting a pattern of skepticism that often accompanies new technologies.

Entrepreneurship and Investment in Web 3

  • The web 3 space is filled with NFT artists, entrepreneurs, and DeFi projects initiated by community members who see a need.
  • The speaker's investment firm prefers backing ambitious and novel ideas that could be massively successful, rather than traditional business plans.
  • The excitement comes from supporting incredible people building ambitious projects.

"We don't invest in business plans. We sit down with an entrepreneur, we listen to their idea. We want it to be new, novel, exciting, and if it works, it should be massive."

This quote emphasizes the investment philosophy of backing unique and potentially transformative ideas rather than conventional business plans.

Kevin Rose's Early Engagement with Bitcoin

  • Kevin Rose first tweeted about Bitcoin in 2012 and had his initial encounter with it in an email from an angel investor in 2011.
  • He received his first Bitcoin as a referral bonus from Coinbase in August 2012.
  • The speaker reflects on the early days of Bitcoin and the excitement of receiving it when it was worth much less.

"So the first email I have about bitcoin is June twelveth of 2011, and it's an angel investor business plan."

The quote marks the speaker's first documented encounter with Bitcoin, showing how early he was exposed to the cryptocurrency.

Foundation Show and Interaction with Trent Reznor

  • The Foundation show used open-source music from Trent Reznor for its intro, aligning with its non-commercial nature.
  • Kevin Rose had the opportunity to visit Trent Reznor's home and was impressed by his recording studio and passion as an artist.
  • The conversation reveals how certain creative experiences, like interviewing Trent Reznor, leave a lasting impression.

"We used to do these before there were ask me anything. We did these things called dig dialogues where people could vote up their favorite questions for people to ask."

The quote explains the concept of "dig dialogues," a precursor to the popular "ask me anything" sessions, and how it was used in the speaker's show.

Early Bitcoin Tweets and Reflections on Coinbase

  • Kevin Rose reflects on his early tweets about Bitcoin, including asking for test transactions and mentioning Coinbase.
  • He regrets losing access to a wallet with over a Bitcoin in it due to lost keys.
  • The speaker interviewed Brian Armstrong of Coinbase on the Foundation show, which helped onboard many into crypto.

"In June 2011, you tweeted, testing out bitcoin. Can someone send a couple of cents to this address?"

This quote is a recollection of one of the speaker's earliest public interactions with Bitcoin, showcasing his early curiosity and engagement with the cryptocurrency.

Evaluating Cryptocurrency and NFT Projects

  • The speaker discusses the importance of discerning the true motivations behind cryptocurrency projects.
  • He believes in avoiding projects that are knockoffs or focused solely on price appreciation.
  • The speaker values projects that push technology forward and have a credible team, avoiding those primarily discussed in the context of making money.

"I always look through the lens of one is there a use case here that needs to be solved that this company is going out and solving? Is it a credible team behind it?"

The quote outlines the speaker's criteria for evaluating new cryptocurrency projects, focusing on practical use cases and the credibility of the team behind the project.

Personal Approach to Buying NFTs and Cryptocurrency

  • Kevin Rose discusses his personal investment strategy, distinguishing between affordable art NFTs and more significant investments.
  • He looks for "blue chip" NFT projects that were first at something or historically important to the space.
  • The speaker's interest in art and design influences his appreciation for and investment in NFTs.

"When I personally buy an NFT, I'll say, first and foremost, what's the price point? If the price point is hundreds of dollars and it's something that you could afford to lose if you had to, then I want to love the art."

This quote reveals the speaker's personal approach to purchasing NFTs, balancing the art's appeal with the consideration of the investment's affordability and risk.

The Value of True Believers in New Paradigms

  • Early adopters who believe in the intrinsic value of a new technology have the most upside potential.
  • The speaker warns of the potential for scams that mimic legitimate emerging trends, exploiting those eager to join the next big thing.
  • The discussion highlights the importance of understanding the motivations behind a project and the community's focus on either technology or profit.

"Anytime there's a paradigm shift, it requires a leap of faith to become a true believer in the new thing."

The quote captures the essence of embracing new paradigms and the risks and rewards associated with being an early believer in a groundbreaking concept.

Kevin Rose's Career and Transition to Full-Time Investing

  • Kevin Rose discusses his career journey, including his transition from being an entrepreneur to a full-time investor.
  • He values the long-term, relationship-focused approach of his investment firm, True Ventures.
  • The speaker's decision to move into investing was influenced by his desire for a better quality of life and his passion for supporting entrepreneurs.

"It's about getting more people on board and excited about these new and upcoming technologies and hopefully helping them avoid a lot of the crap that's out there."

The quote reflects the speaker's motivation to educate and guide people through the complex landscape of new technologies, emphasizing the importance of authenticity and avoiding scams.

Kevin Rose's Focus on Blockchain and NFT Investments

  • Kevin Rose primarily evaluates cryptocurrency, blockchain, and NFT-related companies in his role at True Ventures.
  • He has helped deploy a significant portion of the fund's capital into blockchain startups, demonstrating a strong belief in the technology's future.
  • The conversation underscores the substantial investment and interest in blockchain and NFTs within the venture capital space.

"We've probably deployed, if I had to guess, probably 75 million this year into blockchain related startups."

This quote indicates the level of financial commitment and confidence the speaker's firm has in the potential of blockchain technology and related startups.

Impact of Technology on Various Sectors

  • Technology is anticipated to revolutionize multiple industries, particularly finance, collectibles, and gaming.
  • These changes are expected to have a significant effect on how these sectors operate.

"that this technology is going to change everything, especially the financial and collectibles world and gaming as well."

The quote underlines the transformative potential of technology across critical industries, emphasizing a shift in traditional operations within these sectors.

Crusoe: A Clean Compute Cloud Provider

  • Crusoe is a company that provides cloud services specifically optimized for AI workloads.
  • Nvidia is a major partner of Crusoe, and their data centers consist mainly of Nvidia GPUs.
  • Crusoe's data centers are located at sites with stranded energy, such as oil flares and wind farms, which allows them to utilize energy that would otherwise be wasted.
  • The use of stranded or clean energy allows Crusoe to offer improved performance per dollar compared to traditional cloud providers.
  • Energy is a significant cost in running AI, second only to the cost of chips from Nvidia.
  • Crusoe's approach benefits both the environment and customers by reducing reliance on the energy grid and lowering costs.

"Crusoe's data centers are nothing but racks and racks of a. Because Crusoe's cloud is purpose built for AI and run on wasted, stranded, or clean energy, they can provide significantly better performance per dollar than traditional cloud providers."

This quote explains Crusoe's business model, highlighting their specialization in AI workloads and cost-effective performance, which is achieved through innovative energy use.

Differentiation in the Cryptocurrency and NFT Space

  • Traditional cryptocurrency and DeFi (Decentralized Finance) are seen as one bucket, while the developments with NFTs (Non-Fungible Tokens) represent a separate and distinct area.
  • A new podcast called "Proof" is being launched to explore all things related to NFTs, including art, programmability, generative aspects, DAOs (Decentralized Autonomous Organizations), gaming, and virtual land.
  • The "Modern Finance" podcast will continue to cover broader crypto topics, including DeFi, scaling solutions, and new coins, but will feature significant NFT developments occasionally.
  • The division into two podcasts is a response to differing audience demands for more NFT content and traditional crypto discussions.
  • The "Proof" podcast aims to delve into the nuances of the NFT ecosystem, showcasing emerging artists and innovative uses of NFTs.

"So 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, just NFT content."

The quote announces the launch of a new podcast focused on the diverse and evolving world of NFTs, catering to a growing interest in this specific segment of the cryptocurrency space.

Evolution and Future Potential of NFTs

  • NFTs are seen as a vehicle for valuing digital artwork, providing artists with incentives to create rare and innovative pieces.
  • The younger generation values their digital identity, often more than their physical one, and NFTs cater to this demographic by enabling ownership of virtual goods.
  • NFTs offer unique features not possible with traditional art, such as programmability, portability, and resilience to physical damage.
  • The historical resistance to the transition from wall or wood paintings to canvas art is paralleled in the skepticism some have towards NFTs.
  • The future of art consumption and ownership could involve digital displays and seamless transactions using blockchain technology.

"I just love that there's something really cool about being able to walk into a gallery or bar or wherever you are, see something on the wall and being like, wow, that artist really connects with me. Oh, it's $700 worth of eth scan, a code, it transfers to your wallet, it disappears from the wall. Something else appears there, and now you own it. That's freaking cool. That is going to happen."

This quote captures the transformative experience NFTs could bring to art ownership and appreciation, emphasizing the seamless integration of technology and the arts.

The Intersection of Content and Commerce

  • The speaker discusses their experience with Hodinkee, a platform combining in-depth editorial content with e-commerce for watches.
  • Hodinkee successfully maintained a balance between critical editorial content and commercial interests, ensuring credibility and trust.
  • The speaker plans to apply similar principles to the NFT space, particularly with the "Proof" podcast.
  • The goal is to build trust by providing high-quality content and editorial coverage of the NFT industry, highlighting the importance of historical context and artistic value.

"I don't think of these businesses being built in the next six months to a year. We need to spend the first three years gaining trust."

This quote emphasizes the long-term approach to building a business in the NFT space, focusing on establishing trust through quality content and editorial integrity.

Venture Capital and Entrepreneur Engagement

  • Most deals in the speaker's venture capital firm come from referrals by entrepreneurs they've previously backed.
  • The referral network acts as a filter to manage the volume of pitches the firm receives.
  • The speaker is primarily interested in cryptocurrency, blockchain, NFT-related deals, health and fitness, and some consumer internet projects.
  • Entrepreneurs seeking to engage with the firm are advised to connect through the existing network of backed companies or reach out via open channels like Twitter DMs.

"I would say 90% of our deals come from referrals from entrepreneurs that we've already backed."

The quote explains the venture capital firm's approach to sourcing new investment opportunities, highlighting the importance of a trusted referral network.

Personal Anecdotes and Networking

  • The speaker shares a story about how they were added to Twitter's suggested user list at a bar, leading to a massive increase in followers.
  • This inclusion on the suggested user list indirectly led to the speaker meeting their future wife.
  • The speaker also discusses the historical context of art and technology adoption, drawing parallels between past resistance to new art mediums and current attitudes towards NFTs.

"I had turned on notifications for anytime someone follows me because that's how small it was. And instantly, my phone was like, boom, boom, boom, boom, boom. I was like, holy crap, dude, this is taken off."

This quote recounts a pivotal moment in the speaker's online presence and the power of networking and chance encounters facilitated by social media platforms like Twitter.

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