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Jan 4, 2017 · 22m · 20vc

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

Phil Libin · 13m spoken Harry Stebbings · 6m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The Twenty Minute VC, host Harry Stebbings interviews Phil Libin, former Evernote CEO and Managing Director at General Catalyst, about his transition into venture capital, the maturation of bot technology, and his core investment philosophy.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 33.1% of the talking time here. How this is scored →

Harry as informed peer 1.6 Guest teaching 3.2 Guest disagreement 1.8 Harry pushing back 0.6
05100:0010:0020:002:19–4:34 · Harry as informed peer 1/10 Phil Libin's Transition from Evernote to General Catalyst Harry opens with a broad question about Phil's transition from Evernote to VC. Phil warmly explains his transition process, making the conversation friendly and introductory without pushback.4:36–6:45 · Harry as informed peer 1/10 Lessons from Operating Evernote and VC Surprises Harry relays questions sourced from General Catalyst partner Nico regarding operating lessons and VC surprises. Phil shares personal reflections on focus and operational overhead in VC without friction.6:46–10:38 · Harry as informed peer 2/10 The Evolution and Distribution of Bot Technology Harry prompts Phil on the bot hype and platform distribution concerns. Phil rejects common industry panic over discovery, arguing high quality products like Pokemon Go organically succeed.10:41–13:39 · Harry as informed peer 2/10 Defining Meaningful Bots and Software Botification Harry asks about meaningful bots and potential software botification. Phil outlines a clear taxonomy separating authoring tools from conversational software and draws parallels to early app days.13:45–20:24 · Harry as informed peer 2/10 Bot Business Models and Interfacing Paradigms Phil details how bots disrupt human-computer interaction by participating in multi-human conversations, then navigates a quickfire round covering his 'Star Trek vs Mad Max' investment philosophy.2:19–4:34 · Guest teaching 1/10 Phil Libin's Transition from Evernote to General Catalyst Harry opens with a broad question about Phil's transition from Evernote to VC. Phil warmly explains his transition process, making the conversation friendly and introductory without pushback.4:36–6:45 · Guest teaching 2/10 Lessons from Operating Evernote and VC Surprises Harry relays questions sourced from General Catalyst partner Nico regarding operating lessons and VC surprises. Phil shares personal reflections on focus and operational overhead in VC without friction.6:46–10:38 · Guest teaching 5/10 The Evolution and Distribution of Bot Technology Harry prompts Phil on the bot hype and platform distribution concerns. Phil rejects common industry panic over discovery, arguing high quality products like Pokemon Go organically succeed.10:41–13:39 · Guest teaching 4/10 Defining Meaningful Bots and Software Botification Harry asks about meaningful bots and potential software botification. Phil outlines a clear taxonomy separating authoring tools from conversational software and draws parallels to early app days.13:45–20:24 · Guest teaching 4/10 Bot Business Models and Interfacing Paradigms Phil details how bots disrupt human-computer interaction by participating in multi-human conversations, then navigates a quickfire round covering his 'Star Trek vs Mad Max' investment philosophy.2:19–4:34 · Guest disagreement 0/10 Phil Libin's Transition from Evernote to General Catalyst Harry opens with a broad question about Phil's transition from Evernote to VC. Phil warmly explains his transition process, making the conversation friendly and introductory without pushback.4:36–6:45 · Guest disagreement 1/10 Lessons from Operating Evernote and VC Surprises Harry relays questions sourced from General Catalyst partner Nico regarding operating lessons and VC surprises. Phil shares personal reflections on focus and operational overhead in VC without friction.6:46–10:38 · Guest disagreement 4/10 The Evolution and Distribution of Bot Technology Harry prompts Phil on the bot hype and platform distribution concerns. Phil rejects common industry panic over discovery, arguing high quality products like Pokemon Go organically succeed.10:41–13:39 · Guest disagreement 2/10 Defining Meaningful Bots and Software Botification Harry asks about meaningful bots and potential software botification. Phil outlines a clear taxonomy separating authoring tools from conversational software and draws parallels to early app days.13:45–20:24 · Guest disagreement 2/10 Bot Business Models and Interfacing Paradigms Phil details how bots disrupt human-computer interaction by participating in multi-human conversations, then navigates a quickfire round covering his 'Star Trek vs Mad Max' investment philosophy.2:19–4:34 · Harry pushing back 0/10 Phil Libin's Transition from Evernote to General Catalyst Harry opens with a broad question about Phil's transition from Evernote to VC. Phil warmly explains his transition process, making the conversation friendly and introductory without pushback.4:36–6:45 · Harry pushing back 0/10 Lessons from Operating Evernote and VC Surprises Harry relays questions sourced from General Catalyst partner Nico regarding operating lessons and VC surprises. Phil shares personal reflections on focus and operational overhead in VC without friction.6:46–10:38 · Harry pushing back 1/10 The Evolution and Distribution of Bot Technology Harry prompts Phil on the bot hype and platform distribution concerns. Phil rejects common industry panic over discovery, arguing high quality products like Pokemon Go organically succeed.10:41–13:39 · Harry pushing back 1/10 Defining Meaningful Bots and Software Botification Harry asks about meaningful bots and potential software botification. Phil outlines a clear taxonomy separating authoring tools from conversational software and draws parallels to early app days.13:45–20:24 · Harry pushing back 1/10 Bot Business Models and Interfacing Paradigms Phil details how bots disrupt human-computer interaction by participating in multi-human conversations, then navigates a quickfire round covering his 'Star Trek vs Mad Max' investment philosophy.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 86.7% · guest 13.3%0:00 · Harry 86.7% · guest 13.3%3:00 · Harry 13% · guest 87%3:00 · Harry 13% · guest 87%6:00 · Harry 24.1% · guest 75.9%6:00 · Harry 24.1% · guest 75.9%9:00 · Harry 8% · guest 92%9:00 · Harry 8% · guest 92%12:00 · Harry 23.1% · guest 76.9%12:00 · Harry 23.1% · guest 76.9%15:00 · Harry 17.2% · guest 82.8%15:00 · Harry 17.2% · guest 82.8%18:00 · Harry 33.2% · guest 66.8%18:00 · Harry 33.2% · guest 66.8%21:00 · Harry 100% · guest 0%21:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 9:06 Dismissing bot discovery concerns

Phil forcefully rejects the common industry premise that app stores are broken and bot distribution will be impossible, insisting that quality products effortlessly find discovery.

 Hardest push from Harry ▶ 8:50 Probing platform dependency

Harry explicitly presses Phil on whether messaging platform dominance and platform-centric ecosystems create risks for the rise of bots.

 Biggest teaching moment ▶ 14:45 Redefining the human-computer interaction paradigm

Phil educates Harry on how conversational bots represent a fundamental paradigm shift from one-person-one-computer software to active multi-human conversation participants.

 Harry holds his own ▶ 7:00 Framing the SF bot explosion

Harry uses his own observation from San Francisco to challenge Phil on why bots suddenly captured industry attention after years of existing.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Phil Libin's Transition from Evernote to General Catalyst 1100 Harry opens with a broad question about Phil's transition from Evernote to VC. Phil warmly explains his transition process, making the conversation friendly and introductory without pushback.
Lessons from Operating Evernote and VC Surprises 1210 Harry relays questions sourced from General Catalyst partner Nico regarding operating lessons and VC surprises. Phil shares personal reflections on focus and operational overhead in VC without friction.
The Evolution and Distribution of Bot Technology 2541 Harry prompts Phil on the bot hype and platform distribution concerns. Phil rejects common industry panic over discovery, arguing high quality products like Pokemon Go organically succeed.
Defining Meaningful Bots and Software Botification 2421 Harry asks about meaningful bots and potential software botification. Phil outlines a clear taxonomy separating authoring tools from conversational software and draws parallels to early app days.
Bot Business Models and Interfacing Paradigms 2421 Phil details how bots disrupt human-computer interaction by participating in multi-human conversations, then navigates a quickfire round covering his 'Star Trek vs Mad Max' investment philosophy.

Statements from this episode (8)

Assertion Not checkable as stated
Phil Libin almost entirely stopped using email as Evernote CEO
“I'd kind of stopped sitting and I stopped doing email almost entirely. Like for the past few years of my life, like I had very, very slight contact with email”
Phil Libin Jan 4, 2017 ▶ 5:56
Insight
Great Products Get Discovered Automatically Without a Distribution Strategy
“I've never cared about discovery and about distribution. I think, like, the best stuff gets discovered automatically.”
Phil Libin Jan 4, 2017 ▶ 9:47
Prediction Not checkable as stated
Only a Couple Hundred Famous Bots Will Dominate Globally
“There's going to be a couple of hundred famous bots in the world, and everyone's going to know them, and everyone's going to be able to interact with them, and they're not going to be, it's not going to matter what directories are listed in. They're just going…”
Phil Libin Jan 4, 2017 ▶ 10:11
Prediction Not checkable as stated
80% of Work Software and 50% of Consumer Software Will Become Conversational
“So my guess is about 50% of what we use as consumers will become conversational, botified, and about 80% of what we do at work.”
Phil Libin Jan 4, 2017 ▶ 12:02
Disclosure
Phil Libin Only Invests in Bots With Direct Pay-For-Function Utility Models
“The stuff that we're working on, the stuff that I'm investing in or helping to build, it's all like the, these are bots that do specific functions that people pay for.”
Phil Libin Jan 4, 2017 ▶ 14:08
Prediction Not checkable as stated
Bots Will Disrupt Software by Joining Multi-Human Conversations
“I think it's a major point of disruption. I think that the single biggest change is going to be for the past few decades almost all of our interactions with technology have been one person interacting with some system. So it's been like you using Microsoft Wor…”
Phil Libin Jan 4, 2017 ▶ 14:45
Prediction Not checkable as stated
Phil Libin Maintains a Strict Personal Rule Never to Work on Airplanes
“A really quick one is I don't work on airplanes. I made this arbitrary rule where I will not work on an airplane.”
Phil Libin Jan 4, 2017 ▶ 17:24
Insight
Libin Refuses to Invest in Startups Not Advancing a Star Trek Future
“My entire long-term investment hypothesis is really straightforward. Like, I think the world has two possible futures. Like, there's two directions that the world can go in. The world can become more like Star Trek, or the world can become more like Mad Max. E…”
Phil Libin Jan 4, 2017 ▶ 19:35
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