Jan 25, 2021 · 41m · 20vc
20VC: Evernote & mmhmm Founder Phil Libin on Why We are Beginning a Multi-Trillion Dollar Restructuring of the World, Why Shortcuts are the Biggest Mistakes Startups Make & The Future of Video and The Unbundling of Zoom
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In this episode of The 20 Minute VC, host Harry Stebbings interviews Phil Libin, co-founder and CEO of mmhmm and former CEO of Evernote. Libin shares deep insights on leadership, startup recruitment, the flaws of traditional venture capital incentives, and why remote work is triggering a multi-trillion-dollar restructuring of global communication.
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 30.8% of the talking time here. How this is scored →
Harry as informed peer 3.4 Guest teaching 5.6 Guest disagreement 3.0 Harry pushing back 2.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:19 Calling out 'relationship business' as amateur
Phil forcefully rejects Harry's claim that media and venture are relationship businesses, labeling that line of thinking as a sign of an immature, non-serious industry.
Hardest push from Harry ▶ 12:59 Harry challenges delegation model with relationship argumentHarry directly refuses Phil's blanket advice on delegation, arguing that highly network-driven businesses based on personal relationships cannot simply be handed off to subordinates.
Biggest teaching moment ▶ 11:33 Phil provides live 'founder therapy' on delegationPhil explicitly re-educates Harry on CEO responsibility, pointing out that an inability to delegate is a personal failure to hire people who are strictly superior at their respective roles.
Harry holds his own ▶ 12:59 Harry counters Phil's hiring advice using industry realitiesHarry pushes back on Phil's idealist management philosophy by presenting the practical reality of relationship-governed media businesses, forcing Phil to defend his position.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Phil Libin's Startup Journey and the Founding of mmhmm | 3 | 3 | 1 | 1 | Harry asks standard, well-structured questions regarding Phil's startup background, team retention, and hiring strategies. Phil responds collaboratively, offering advice on allocating capital toward recruiters to hire outside comfortable social circles. | |
| Startup Shortcuts and Venture Capital Incentives | 4 | 7 | 4 | 4 | Phil playfully blames VCs for forcing startups into taking shortcuts and then offers Harry live 'founder therapy' when Harry admits to struggling with delegation. Harry pushes back by questioning how delegation works in relationship-driven industries. | |
| Deconstructing the Relationship Fallacy and 'Brain Is Not My Friend' | 3 | 8 | 5 | 3 | Phil sharply rejects the idea that business is about personal relationships, calling that mindset a crutch of non-serious industries and contrasting it with Netflix's professionalization of Hollywood. He introduces his 'brain is not my friend' framework to explain cognitive biases. | |
| Lessons Learned as an Investor at General Catalyst | 3 | 5 | 2 | 2 | Phil reflects self-deprecatingly on his time as a venture capitalist at General Catalyst, explaining how Hemant Taneja identified why he processed pitches like a CEO rather than an investor. He also discusses adapting leadership styles for introverted employees in remote work setups. | |
| Consumer vs. Enterprise Markets and the Video Transformation | 4 | 7 | 4 | 2 | When Harry asks about B2B vs. B2C usage patterns, Phil reframe-challenges the premise as an overly reductive Western analytic approach that ignores core similarities. He then lays out his thesis on the multi-trillion-dollar restructuring of the world through video integration. | |
| Building Native Video Software and Managing Growth vs. Impact | 4 | 6 | 3 | 3 | Phil draws a historical parallel between early theater-style movies and first-generation video tools, predicting a shift toward native video applications. Harry probes about downside protection, but Phil argues early-stage startups should focus entirely on impact rather than risk mitigation. | |
| Quickfire Round: Books, Silicon Valley, and Board Members | 3 | 3 | 2 | 1 | During the quickfire round, Phil shares book recommendations, critiques Silicon Valley's geographical concentration of opportunity, makes self-deprecating jokes about his upper body strength, and praises board member Roelof Botha for keeping conversational state across meetings. |
Statements from this episode (19)
Libin: mmhmm started as a joke to make Zoom calls less boring
“It started as a joke, just as a way to make our life on video a little bit less boring. So we just started goofing around with backgrounds and pictures and things you can do in Zoom, and pretty soon it became a product.”
Libin: The biggest shortcut early-stage startups take is hiring personal friends
“One of the many things that are wrong with startups is startups are all about shortcuts. All of the incentives are to take as many shortcuts as you can. The biggest shortcut that you can take is just hiring your friends”
Libin: Startups aren't serious about talent diversity unless they spend money
“I mean, for businesses, you pretty much, it all comes down to the same tool, which is money. So if you're not spending money on it, you're not serious about it.”
Libin: We pay recruiters specifically to source out-of-network candidates
“So we spend money on recruiters and we specifically tell recruiters that we are paying you money to send us people that are outside of our comfort zones and outside of our networks, because we know plenty of, you know, middle-aged white dudes.”
Libin: Early-stage VC incentives force startups to take damaging shortcuts
“The incentives are when you're investing, especially if you're doing early stage investing, just like me, you're not looking for things that are likely to succeed, right? You're looking for things that have a plausible chance of succeeding, even if it's not a …”
Libin: The shift to video communication is a multi-trillion-dollar opportunity
“And for mm-hmm, since I think this is a multi-trillion dollar thing that's happening right now, I think mm-hmm needed to get pretty big, pretty quickly, raise external capital, and so it was a perfect thing to say, okay, yeah, embodying this in a spin-out star…”
Libin: Founders should be the worst person at every job function
“So never hire someone whose job you can do better than them. Only hire people, only surround yourself with people that are ridiculously better than you or that are superior to you in their job or other things as much as possible. Like always be the worst perso…”
Libin: A founder's struggle to delegate is a failure to hire well
“Like, it is your failure if you have not hired people that you think are better than you at their job.”
Libin: Calling an industry a relationship business signals it is immature
“A sign of, like, a non-serious business is when people in it say this is a relationship business. This is a sign of, like, it's immature, and it's not professionalized.”
Libin: Evaluating pitches based on what you would build is flawed
“When you hear a pitch, you get excited about what you would do with this idea. And that's a really shitty way to make investments because you're not going to do anything with this idea. You got to try to figure out what they're going to do with this idea.”
Libin: A leader's strong conviction does not make a belief more accurate
“Just because I believe something strongly doesn't actually make it any more or less likely to be accurate or true than if some random person in the street believed in it strongly.”
Libin: Employees earn no credit for following instructions, only for outcomes
“There are no points for following instructions. There's only points for succeeding, for doing the right stuff”
Libin: Digital collaboration tools unlock productivity from introverted team members
“When we went from being in person to doing all of these things, you know, we no longer do brainstorming in a big conference room with, you know, stick stickies, post-it notes, you know, now we do it all on Figma, and actually I started noticing, man, I'm just …”
Libin: Formal performance reviews often do more harm than good
“I just haven't had good success with like reviews that felt more useful than harmful.”
Libin: Video integration will transform everything within two years
“Integrating video into everything in this hybrid model is going to literally affect almost a hundred percent of all things in life. It's going to be a bigger transformation as the dot-com transformation was, except it's not going to take 10 years. It's going t…”
Libin: Within a year, native video startups will redefine meetings
“And obviously, within a year, like, this isn't what video is going to be like. Obviously, It's going to be the next generation of like native to video companies that comes along and says, well, no, we're not trying to recreate the old reality. We're not trying…”
Libin: Exceptional talent is global, but opportunity is concentrated near Stanford
“Exceptional talent, like, Mozart-level brilliant, exceptional talent is very, very rare in the world, but it's evenly distributed, and, but opportunity isn't, and so it is bad for the world that so much of the opportunity for crazy, exceptionally talented, cre…”
Libin: Most startup boards are stateless, but Roelof Botha maintains context
“Most boards' conversations are totally stateless, meaning that the board members walk in, and they don't remember anything that you talked about before, and you start over. And this is the most frustrating thing for entrepreneurs, because, of course, like, you…”