20VC Evernote's Phil Libin on The Pros and Cons Of Moving To VC, The Future For Bots & Having Marc Benioff & Reid Hoffman As Mentors

Summary Notes


In this episode of "20 minutes VC," host Harry Stebbings interviews Phil Libin, the managing director at General Catalyst and founder and executive chairman at Evernote. Libin discusses his transition from CEO of Evernote to venture capital, emphasizing his desire to continue building and tinkering rather than purely investing. He shares insights on the future of bots, predicting that meaningful bots will enhance human conversations and that a substantial portion of consumer and work software will become conversational. Libin also touches on his investment philosophy, which is driven by a desire to push the world towards a more positive, "Star Trek"-like future, and his recent investment in Sunflower Labs, a home security drone company. Throughout the conversation, Libin reflects on personal productivity, mentorship, and the importance of creating products that people are willing to pay for, without relying on overly complex business models.

Summary Notes

Introduction to the Podcast and Host

  • Harry Stebbings is the host of the 20 minutes VC podcast.
  • Harry is active on Snapchat and writes on Mojitovc.com.
  • The podcast aims to bring interviews with major figures in the industry.

This is the 20 minutes VC with your host Harry Stebbings at h Stebbings on Snapchat and found writing some hopefully intelligent things on Mojitovc.com.

This quote introduces the host, Harry Stebbings, and sets the stage for the podcast's objective to deliver high-profile interviews.

Guest Introduction: Phil Libin

  • Phil Libin is the managing director at General Catalyst and founder and executive chairman at Evernote.
  • Phil evolved Evernote from an idea to a productivity platform with millions of users.
  • Evernote secured over $160 million in VC funding from top firms like Sequoia Capital.
  • Phil has a fondness for all things boss and has made several angel investments.
  • Nico Bonassos facilitated Phil's introduction to the podcast.

So joining me today, I'm thrilled to welcome Phil Libin. Now Phil is managing director, general catalyst and founder and executive chairman at Evernote.

This quote introduces Phil Libin, highlighting his roles and achievements, setting the stage for the discussion about his career and insights.

Sponsorship and New Year's Resolutions

  • Simba Hybrid is promoted as an advanced mattress with a unique combination of springs and memory foam.
  • Sirius Insight is a productivity tool for sales professionals integrating with Gmail, Outlook, and Salesforce.

And that's where Simba hybrid comes in. It's the most advanced mattress in the world. And Sirius Insight is perfect for sales support and success.

These quotes describe the sponsors of the podcast, Simba Hybrid and Sirius Insight, linking them to the themes of sleep and productivity, which are part of the host's New Year's resolutions.

Phil Libin's Transition to Venture Capital

  • Phil did not plan his post-Evernote career while at Evernote.
  • He decided to replace himself as CEO before considering future plans.
  • Phil was approached by VC firms after announcing his departure from Evernote.
  • Despite being familiar with VCs, Phil had not considered becoming one.
  • He initially rejected the idea of being a VC, preferring to build and start companies.

I kind of specifically refused to think about what I would do after Evernote. And up until that point, I'd never really thought about being a VC.

Phil explains that he deliberately avoided planning his future while at Evernote and that he was new to the idea of being a venture capitalist, which emphasizes his focus on his role at Evernote and his initial reluctance to transition into VC.

The Incubator Plan and Joining General Catalyst

  • Phil's initial plan was to create an incubator to work on various projects.
  • General Catalyst offered him a role where he could incubate projects and invest.
  • Phil was attracted to the opportunity to do both within a larger platform.

So what I decided to do was I was going to make an incubator. Their pitch to me know, come here and do both.

This quote outlines Phil's initial plan to start an incubator and General Catalyst's proposal, which allowed him to combine his interest in incubating with investing.

Phil's Approach to Focus and Diversification

  • Running a company requires intense focus, often advised by investors and board members.
  • Phil structured his life post-Evernote to work on a variety of things without feeling guilty.
  • He now enjoys the freedom to explore different interests and meet entrepreneurs.

Now is kind of the biggest eye-opening thing was when you're running a company, it really is all about focus.

Phil reflects on the importance of focus when running a company and how his current role allows him to diversify his interests and activities without the guilt associated with deviating from a company's core mission.

Transition to Venture Capital (VC)

  • Harry Stebbings discussed the unexpected aspects of transitioning to VC, including the increase in sitting and email communication.
  • The positive surprise was the exposure to big picture ideas and engaging with people building amazing things.
  • Despite minor frustrations, the overall experience was more positive than expected.

"Oh, so much sitting around, so much email."

This quote highlights the increased sedentary nature and volume of email communication experienced after transitioning to venture capital.

"The biggest positive surprise is, like, how amazing all of the big picture things are, how it's my job to learn about really cool things and how people that are building amazing things, want to talk to me and want to tell me what they're working on."

This quote reflects the excitement and satisfaction derived from learning about innovative ideas and interacting with creators in the VC role.

Explosion of Excitement in Bots

  • Phil Libin noted that the excitement around bots does not necessarily equate to important progress.
  • Fundamental technologies have improved significantly, allowing for commercial combinations and exponential growth in the bot ecosystem.
  • The current state of bot technology is compared to the app boom in 2008, driven by advancements in smartphones, touchscreens, and social media.

"I think the reason that it's happening is we have a package, kind of a basket of fundamental technologies that have each gone from being early and academic to just getting good enough, where now they could be combined in commercial ways."

This quote explains that the convergence of mature technologies has enabled the current surge in bot development.

"So I think that's how the technology cycle is driven."

This quote summarizes the speaker's view on the cyclic nature of technology advancements leading to innovation surges.

Distribution and Platforms for Bots

  • The discussion moved to the distribution of bots through messaging platforms.
  • Phil Libin expressed less concern about the challenges of bot distribution compared to apps.
  • The belief is that quality will lead to discovery, as seen with successful apps like Pokemon Go.
  • The future of bots is seen as a meritocracy, where the most meaningful and high-quality bots will naturally become well-known.

"I really care about the 20 or 30 that are going to be really meaningful."

This quote emphasizes the focus on a small number of bots that will have significant impact rather than the vast number of lesser bots.

"It'll be moving more and more towards a meritocracy of product."

This quote predicts that the quality of bots will be the primary factor in their success and visibility.

Characteristics of Meaningful Bots

  • Phil Libin shared his thoughts on what constitutes a meaningful bot.
  • Bots should have a point of view, be helpful, and assist users in achieving something significant.
  • The value of bots is seen as a hybrid between apps and human interaction.

"You should be doing something. You should have an opinion, a point of view. You should be helpful in actually helping somebody achieve something meaningful."

This quote outlines the criteria for what makes a bot meaningful, emphasizing utility and purpose.

"I think bots are going to be judged somewhere halfway between how apps are judged and how people are judged."

This quote suggests that the assessment of bots will blend the evaluation criteria used for both applications and human contributions.

Botification of Software

  • Not all software should be botified, but a significant portion will become conversational.
  • Authoring and creation tools will remain with rich user experiences.
  • About 50% of consumer software and 80% of business software could become botified.

"I kind of think there's going to be two classes of things. There's going to be authoring and creation tools... And those will probably still be bespoke rich ux... But I think almost everything else... will become conversational, will become a bot."

This quote explains the speaker's perspective on the future of software, distinguishing between tools for creation, which will maintain their complex interfaces, and other types of software which will transition to conversational bots.

Barriers to Bot Proliferation

  • Early bots are often gimmicks or poorly executed ideas.
  • Bots are in an early stage similar to apps in 2008, with most being low quality but with potential for meaningful applications.
  • It may take a year or two for truly useful and native bots to emerge.

"I think bots are the same way. It's like right now, most bots are just gimmicks... But you'll start to see native bots coming out in the next few months... I think it'll take a year or two to get real bots."

The quote compares the current state of bots to the early days of mobile apps, suggesting that while many bots are currently of low quality, the potential for impactful and native bot experiences exists and will be realized soon.

Business Models for Bots

  • The speaker prefers straightforward business models where customers pay for good products.
  • There is a hope that ad models will not dominate the bot space, as ads are generally disliked.

"I think your business model ought to be make something that good enough that people want to pay for it and let people pay for it... I kind of hope that there won't be much of an ad model for bots."

This quote expresses the speaker's belief in creating valuable products that people are willing to pay for, rather than relying on advertising for revenue, especially within the context of bots.

Disruption vs. Evolution in Interface Paradigm

  • The transition to bots represents a major disruption.
  • The future involves multiple humans conversing with technology participating in the conversation.

"It's hard to imagine a more fundamental change in how we deal with technology, where instead of having this custom bespoke paradigm, where I'm poking at something, the technology is there, it's present, and it participates in a conversation among multiple humans."

The speaker predicts a dramatic shift in how humans interact with technology, moving from individual interactions to a more communal conversational experience with bots.

Personal Insights and Preferences

Favorite Book

  • The "Three-Body Problem" trilogy is the speaker's current favorite.
  • It is recommended for its quality as a big-budget Chinese sci-fi series.

"Well, currently it's the Three-Body Problem trilogy, which is amazing. Everyone should read it."

The quote shares the speaker's personal book recommendation, highlighting the "Three-Body Problem" trilogy for its notable impact and recent completion of English translations.

Career Inflection Points

  • The speaker had an epiphany about not being suited for the CEO role as Evernote grew.
  • Career progression and planning are alien concepts to the speaker.

"This is really when I first had an inkling that I probably shouldn't be the CEO of Evernote when we got too big."

This quote reflects a personal realization by the speaker about their suitability for a leadership role in a large company, tying it to a significant moment of self-awareness and career development.


  • The transcript is incomplete and does not provide information on the speaker's mentors.

(Note: The last theme on mentorship is incomplete due to the transcript being cut off.)

Mentors and Influences

  • Speaker B has had multiple mentors who have generously shared their time.
  • Mark Benioff, Reed Hoffman, and Hiroshi Mikitani are specifically mentioned as significant mentors.
  • Hiroshi Mikitani, CEO of Rakuten, has been particularly influential in how Speaker B structures things.
  • Speaker B also values the input from their work partners, including Haman and Nico.

"But Mark Benioff has been a really amazing mentor to me. Reed Hoffman has been great. Hiroshi Mikitani, who's the CEO of Rakuten, the big Japanese company, has been maybe the most influential kind of mentor and thinker on how I structure things."

This quote highlights the importance of mentors in Speaker B's professional life, particularly emphasizing Hiroshi Mikitani's impact on their approach to structuring things.

Productivity Tips

  • Speaker B shares a personal productivity tip of not working on airplanes, preferring to use the time to relax or engage in leisure activities.
  • This rule helps Speaker B look forward to long flights and travel in general.
  • Speaker B enjoys reading and watching movies during flights, which provides a break from work.

"A really quick one is I don't work on airplanes. Made this arbitrary rule where I will not work on an airplane. I sleep, I read, I play video games, I watch movies, but I refuse to work."

This quote explains Speaker B's personal rule to not work on airplanes and how it positively impacts their attitude towards travel.

Reading Habits

  • Speaker B has an eclectic approach to reading, starting the day with major publications.
  • The New York Times and The Economist are part of Speaker B's daily reading routine.
  • Speaker B jokes about the importance of being seen reading The Economist to appear adult-like.
  • Speaker B's online reading is spontaneous, following links and recommendations from email and various streams.

"I'm really eclectic with my reading. Like, I basically wake up in the morning, I read some of the major publications, I read the New York Times every day. I read the Economist. It's important for me to be seen reading the Economist."

The quote illustrates Speaker B's diverse reading interests and the significance of maintaining an informed image, particularly through reading reputable publications like The Economist.

Investment Philosophy

  • Speaker B discusses a recent public investment in Sunflower Labs, a company that makes home security drones.
  • The decision to invest was influenced by the founder's relationship with Speaker B and the innovative nature of the product.
  • Speaker B's long-term investment strategy is to support ventures that push the world towards a "Star Trek" future, which is a metaphor for a positive, science-based, and abundant society.

"My entire long term investment hypothesis is really straightforward. I think the world has two possible futures. There's two directions that the world can go in. The world could become more like Star Trek, or the world could become more like Mad Max."

This quote reveals Speaker B's investment strategy, which is guided by the desire to contribute to a future that is technologically advanced and abundant, akin to the world depicted in Star Trek.

Gratitude and Acknowledgments

  • Speaker A and Speaker C express their gratitude to Speaker B for participating in the show.
  • Speaker A thanks Nico at General Catalyst for making the introduction to Speaker B, which made the show possible.
  • Speaker A is a self-proclaimed Evernote fan and appreciates the opportunity to host Speaker B.

"And I want to say again, a huge thank you to Phil for giving up his time today. To be on the show really was such a pleasure for me as a huge Evernote fan and a huge hand to Nico at General Catalyst for the intro, without which the show would not have been possible."

This quote is a formal expression of gratitude from Speaker A to Speaker B for his participation and to Nico for facilitating the introduction.

Personal and Professional Updates

  • Speaker A shares personal goals for the new year, including getting more sleep and improving productivity.
  • Speaker A endorses the Simba hybrid mattress and Sirius Insight, a plugin for sales professionals.
  • Speaker A invites listeners to provide feedback and stay tuned for future episodes.

"And if you love the show today and would like to see more from me, then do not hesitate to add me on Snapchat at htebings with two B's or check out mojitovc.com."

This quote is an invitation from Speaker A to the audience to engage with him on social media and visit his website for more content, indicating an effort to build a relationship with the listeners and gather feedback.

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