20VC Digg CEO, Gary Liu on The Rebirth Of Digg & The Evolution Of Content

In this episode of "20 minutes VC," host Harry Stebbings interviews Gary Liu, the new CEO of Digg, exploring Gary's journey through the tech industry. Starting at Google, Gary advanced to roles at AOL's Patch and Spotify before taking the helm at Digg. He discusses the evolution and fall of Digg, its rebirth post-2012 under Betaworks, and its current focus on quality content discovery and conversations. Gary highlights Digg's hybrid approach of data-driven curation complemented by editorial insight and expresses the need for thoughtful, civil discourse in online communities. Additionally, he touches on the challenges of monetization in the digital age, advocating for branded content as a viable solution. Gary aspires for Digg to become a 'stutter step' app, a go-to for users in between tasks, by excelling in content discovery and fostering quality conversations.

• Gary Liu is an exceptional operator and the new CEO at DiG, a platform for finding and sharing popular stories.
• Gary has a background in tech, starting at Google in sales operations.
• He then moved to a VC-backed startup, Clickable, focusing on search advertising for SMBs.
• Gary's career progressed through AOL's Patch, where he led revenue strategy and operations.
• He joined Spotify in 2011, leading ad product strategy and Spotify Labs.
• Gary was introduced to DiG by Andrew McLaughlin, a partner at Betaworks and former DiG CEO.
• He became COO at DiG in March 2015, then transitioned to CEO.

"Gary is an exceptional operator, and he's recently been named the new CEO at the infamous Dig, the platform that allows users to find, read and share the most talked about stories on the Internet."

This quote introduces Gary Liu, highlighting his recent appointment as CEO of DiG and his past experiences in the tech industry.

• Gary started at Google, where he learned about sales operations, analytics, and saw the company's massive scale and profitability.
• At Clickable, Gary worked in a less glamorous industry, focusing on making search advertising manageable for small businesses with limited time.
• His time at AOL's Patch involved growing a revenue strategy and operations team from the ground up.
• At Spotify, Gary felt the energy of a scrappy startup and led ad product strategy, eventually leading Spotify Labs.
• His experiences at these companies, especially Google, provided him with principles and practices he hopes to bring to DiG.

"I started my tech career in sales operations at Google in Ann Arbor, Michigan, of all places."

Gary describes his beginnings at Google, setting the stage for the valuable skills and insights he gained from working at such a prominent tech company.

• Gary was an early user of DiG and witnessed the community's migration in 2010.
• Reintroduced to DiG in 2013, he admired the product's design and content curation.
• Conversations with Andrew McLaughlin about DiG's past and future vision excited Gary about the company.
• He joined DiG as COO and later became CEO, as Andrew McLaughlin returned to Betaworks as a full-time partner and chairman of the DiG board.

"I was a dig user early, early on again back in the Kevin and Jay days, like you. And I was also one of the folks that was really, really sad in 2010 when the entire community fled for a bunch of reasons."

Gary shares his personal connection with DiG, indicating his long-term interest and emotional investment in the platform, which later influenced his decision to join the company's leadership.

• Gary acknowledges the importance of the lessons learned at Google, AOL, and Spotify.
• His experience at Google showed him the benchmark of tech company success.
• Gary suggests that working at a large company like Google can provide critical learning for those with entrepreneurial aspirations.
• At AOL's Patch, he learned from the challenges of a company that hadn't yet found a working business model.
• Spotify's startup-like environment in the U.S. provided insights into building a company from a smaller scale.
• Gary believes these experiences equipped him with principles that he can apply to his role at DiG.

"I definitely hope that I've taken some of those principles to dig. Otherwise, I feel like it'll be a serious misuse of the luck that I had along the way."

This quote reflects Gary's desire to leverage his past experiences and the principles he learned from tech giants to succeed in his role at DiG and to not waste the fortunate opportunities he's had in his career.

• Harry Stebbings discusses Gary Liu's early career experiences and the lessons he learned from working at AOL and Spotify.
• At AOL, Gary encountered challenges with monetization in a high-cost organization focused on local news.
• Efficiency, productivity, and business planning were key lessons from AOL for Gary.
• At Spotify, Gary was part of the team that worked on generating revenue, especially for the free service, during a period of significant growth and scaling.

"And so it was a fascinating process of taking what was already a high cost organization in a business that was very, very difficult, which was local news, and trying to figure out how best to monetize." "And then finally at Spotify, certainly in the US, and you can make an argument for even globally at that point in 2011, it wasn't scaled."

These quotes emphasize the challenges Gary faced in monetizing complex, high-cost businesses like local news at AOL and the early stages of Spotify's growth, highlighting the importance of strategic planning in scaling a business.

• Gary Liu provides insight into the history of Digg and its initial success as a content curation platform.
• Digg was founded in 2004 and had a successful run as the "darling of the Internet" until 2010.
• The "Digg effect" describes the significant traffic driven to publishers' websites when featured on Digg's front page.
• However, in 2010, Digg version four was released, fundamentally changing the product and alienating the community.

"Digg's history is fascinating. Founded, I think, in 2004 by Kevin and Jay, the old version of Dig, and had an incredible run through, really about six years until 2010." "It really was Dig version four. That was a launch in the summer of 2010 where Digg effectively fundamentally changed as a product."

These quotes highlight Digg's initial success and influence on internet content curation, followed by the pivotal moment in 2010 when a product update led to a decline in user trust and engagement.

• Gary discusses the controversial update to Digg, known as version four, which introduced unwanted social features and removed popular functionalities.
• The update was unstable and seemed tone-deaf to the community's desires.
• The changes led to a loss of trust in Digg's content democracy, causing users to migrate to Reddit as an alternative.

"A lot of things just didn't quite work the way that they were supposed to, and it did for the community, which you and I were a part of. It felt slightly tone deaf." "And one of the things was that this was actually paired at the same time as the front page, becoming less and less relevant because there was suddenly this group of super users that could effectively control what articles made it to the front page."

These quotes describe the negative reception of Digg version four by the community, the technical issues it faced, and the shift in content control that contributed to its decline.

• Post-2010, CEO Matt Williams attempted to stabilize Digg, but by 2012 the company was split, with assets going to The Washington Post, LinkedIn, and Betaworks.
• Betaworks acquired the Digg brand and merged it with News.me, a simple content discovery tool.
• The new version of Digg aimed to be an efficient way to find interesting content, combining data analytics with editorial oversight.

"By the end of 2012, what happened was that dig was really split apart into kind of three different deals." "The original idea really was to use just data. And as Mike and his team were refactoring news me, the data infrastructure that news me had at the time, and rebuilding the front end of Dig, what they realized was that data just wasn't quite enough."

The quotes explain the transition of Digg after its decline, including the sale of its assets and the strategy behind the new direction under Betaworks, which aimed to blend data-driven content curation with editorial expertise.

• Dig's core product revolves around curating quality content for the homepage.
• The company distinguishes itself within the crowded news sector by focusing on quality content discovery.
• Dig is not aiming to compete directly with breaking news or social viral content platforms.

That's what we have as dig today.

The quote explains that the essence of Dig's product, as it stands, is a curated content platform that has remained largely unchanged with only minor tweaks since its inception.

We break down products and platforms in three different ways. We have breaking news, we have social environmental content, and then we have quality content discovery. And we believe that we sit in that third bucket.

Gary Liu categorizes the news sector into three segments and positions Dig in the 'quality content discovery' segment, differentiating it from breaking news and social viral content.

• Dig is not publisher-specific; it focuses on quality content from various sources, including individual publishers on Medium or personal blogs.
• The platform values content that is educational and enriching, regardless of the content's length.
• Dig aims to redefine quality content discovery and build the right product for this purpose.

We're going to take all the publishers effectively equally.

Gary Liu emphasizes that Dig does not favor specific publishers but rather seeks quality content from a wide range of sources.

It doesn't have to be long form, but certainly long form as a format lends itself to quality.

This quote clarifies that while long form content often correlates with quality, Dig is open to shorter pieces that still meet their quality standards.

• Dig plans to reintroduce quality conversations into the platform, addressing the challenges associated with online commenting.
• The new feature, 'dig dialogue,' aims to foster thoughtful, civil conversations anchored on quality content.
• The conversational platform is designed to feel like a live chat and is pre-moderated to maintain a high standard of discourse.

We want to reintroduce quality conversation into the platform.

Gary Liu explains that Dig is seeking to enhance the user experience by adding a feature that allows users to engage in meaningful discussions about the content they consume.

Our product itself, the actual conversational platform, is built to feel much more like a live chat than a commenting system where you have to refresh.

This quote details the user-friendly nature of Dig's conversational platform, which aims to create a dynamic and engaging environment for users.

• Dig acknowledges the challenge of monetizing content due to the prevalence of ad blockers and the decreasing ad revenue.
• The company recognizes a value gap between content creation and consumption, exacerbated by the expectation of free content.
• Dig's approach to monetization includes branded content or native advertising, allowing brands to co-create quality content that users want to consume.

The biggest issue at this point is ad blockers.

Gary Liu identifies ad blockers as a significant obstacle for publishers and media companies in generating revenue from ads.

The one answer that at this point seems repetitive, but really is the direction that the industry is going in is branded content.

This quote reveals Dig's strategy to pivot towards branded content as a solution to the monetization challenge posed by ad blockers and changing consumer preferences.

Our ad product right now is relatively simple on our homepage and we really care a lot about what goes on there.

Gary Liu underscores Dig's careful consideration of the ads displayed on their homepage, suggesting a focus on maintaining quality and relevance in their advertising strategy.

• Digg is selective about the products, services, and educational platforms they feature on their homepage.
• They actively search for offerings that align with their editors' and employees' interests and preferences.
• The promotion on Digg's homepage includes a daily highlight of a chosen product or service.
• Digg collaborates with brands to ensure the landing pages provide valuable and informative content.
• They recently partnered with Blue Apron to create content on cooking the perfect steak, with easy-to-follow GIFs.

We actually go out and search for some of the best products, services, educational platforms that as dig editors and dig employees we would want to use.

This quote explains that Digg's team curates products and services that they personally find valuable, implying a level of trust and quality in what they promote.

So once a day we will choose one of these products and services and we will promote it on our homepage.

Here, the speaker outlines the frequency and method of promotion for selected products, indicating a daily spotlight on the homepage.

But we work with the advertiser or the brand to make sure that that landing page is actually telling you something that you didn't know before.

The speaker highlights Digg's commitment to providing educational value in their advertisements, not just a direct sales pitch.

So we actually created a page that taught you how to cook the perfect steak.

This quote exemplifies how Digg creates engaging and useful content in partnership with advertisers, focusing on user value.

• Gary Liu views his current job as a career highlight, indicating satisfaction and pride in his role.
• He shares an anecdote from his time at Spotify involving Lars Orek from Metallica and Sean Parker, showcasing a memorable personal experience.
• Gary had the opportunity to witness a reconciliatory moment between Lars Orek and Sean Parker, which he considers a standout moment in his career.

Oh man, I think the right answer should be getting this job that I'm in right now.

Gary suggests that his current position is a significant achievement, reflecting on his career progression.

When I was at Spotify, I had the opportunity to watch an incredible scene where Lars Orek, the drummer from Italica, and Sean Parker, one of the founders of Napster, kind of made up on stage.

This quote provides context for one of Gary's career highlights, emphasizing the unique experiences available in his line of work.

• Gary recommends John Russell's Asia Tech news review newsletter for its in-depth coverage of the Asian tech market.
• He admires Ben Sung, a partner at Primary Ventures and former founder of social sites, for his ideas and transition from operator to venture capitalist.

One of my favorites right now is John Russell, who's the Asia editor for TechCrunch.

Gary identifies John Russell as a valuable source for tech news in Asia, highlighting the importance of specialized regional insight.

He also was the founder of a series of social sites back when, including Asian Avenue, Black Planet.

This quote reveals Gary's admiration for Ben Sung's entrepreneurial background and contributions to the tech industry.

• Gary's preferred productivity tool is Gmail, which he uses with multiple inboxes and tags to manage tasks and action items.

Honestly, it's Gmail.

The speaker shares his reliance on Gmail as a productivity tool, demonstrating its versatility and personal organization system.

• Gary believes there is a need for both long and short-form journalism.
• He sees a natural progression from short-form breaking news to more in-depth long-form investigative pieces.

I think both. I think there is absolutely a place for both.

This quote reflects Gary's perspective on the importance of different lengths and styles of journalism to cater to various content needs.

• Gary's favorite book is "Franny and Zoe" by J.D. Salinger, particularly for its footnote that connects Salinger's literary world.

And I think my favorite there is probably Franny and Zoe.

The speaker shares his literary preference, offering insight into his personal interests and what he values in literature.

• Gary aims to make Digg the best content discovery platform with the best online conversations.
• He aspires for Digg to become a "stutter step app," a go-to app for users in their idle moments.

We are trying very much to create the best content discovery in the world, also have the best conversation in the world.

Here, Gary outlines the strategic goal for Digg, focusing on content discovery and user engagement.

And we think that if we get best kind of discovery and best conversation and we find the intersection between those two, then dig can become that stutter step app.

The speaker articulates the long-term vision for Digg, aiming to become a staple in users' digital habits.

• Gary expresses modesty and openness to editing his interview responses.
• Harry Stebbings concludes the episode by praising Gary's career and vision for Digg's future.

Harry, thanks so much. Hopefully you should cut and edit my answers as much as you need.

Gary's humility is evident as he allows for his interview to be edited for clarity or brevity.

What a fantastic episode that was and absolutely brilliant to hear his career at Spotify, at Google, and the lessons learned and how he plans to regenerate dig into the incredible company that it once was and will be in the future.

Harry summarizes the episode, commending Gary's past experiences and his plans for revitalizing Digg.