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Aug 1, 2016 · 26m · 20vc

20VC: YC's Justin Kan on The 3 Qualities All Successful Investors Have & Why 'VCs Don't Really Do Any Real Work'?

Justin Kan · 17m 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 20 Minute VC, host Harry Stebbings interviews Justin Kan, partner at Y Combinator and co-founder of Twitch. Kan shares insights on Y Combinator's scaling model, the evolution of seed investing, founder evaluation criteria, and his personal journey from entrepreneur to angel investor.

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 28.5% of the talking time here. How this is scored →

Harry as informed peer 3.6 Guest teaching 4.2 Guest disagreement 2.0 Harry pushing back 2.6
05100:0010:0020:001:59–7:33 · Harry as informed peer 2/10 Justin Kan's Entrepreneurial Journey and Path to YC Justin provides a lengthy summary of his entrepreneurial path from Kiko to Justin.tv, Socialcam, and Twitch's sale to Amazon. Harry maintains an encouraging, light banter role, interjecting briefly with a joke about the acquisition price missing the $1B mark.7:34–12:10 · Harry as informed peer 6/10 Evolution of YC Interviews and the Venture Capital Landscape Harry demonstrates strong industry context by quoting Sam Altman's Stanford lecture about older VCs and probing whether YC's $700M Continuity Fund directly competes with traditional venture firms. Justin reframes YC's emergence through classical disruption theory and clarifies where the continuity fund actually competes.12:11–14:22 · Harry as informed peer 3/10 Angel Investment Philosophy and Pattern Recognition Harry asks Justin about his personal angel investing rules and how his decision-making evolved since 2012. Justin explains how his pattern recognition shifted away from market-size thesis toward evaluating founder execution capability.14:22–17:44 · Harry as informed peer 4/10 Scaling Y Combinator Batches and Managing Founder Needs Harry asks how YC scales batch size while preserving mentorship quality and asks if any competing brand outperforms YC. Justin outlines YC's sharded group structure and enumerates the three core pillars of investor success.17:44–25:07 · Harry as informed peer 3/10 Leveraging Snapchat for Startup and Fitness Advice During Snapchat talk and quickfire questions, Justin offers candid, contrarian opinions, notably asserting that VC is an easy job because VCs do not do real work. Harry listens and mildly probes, acknowledging Justin's provocative stance in the outro.1:59–7:33 · Guest teaching 3/10 Justin Kan's Entrepreneurial Journey and Path to YC Justin provides a lengthy summary of his entrepreneurial path from Kiko to Justin.tv, Socialcam, and Twitch's sale to Amazon. Harry maintains an encouraging, light banter role, interjecting briefly with a joke about the acquisition price missing the $1B mark.7:34–12:10 · Guest teaching 5/10 Evolution of YC Interviews and the Venture Capital Landscape Harry demonstrates strong industry context by quoting Sam Altman's Stanford lecture about older VCs and probing whether YC's $700M Continuity Fund directly competes with traditional venture firms. Justin reframes YC's emergence through classical disruption theory and clarifies where the continuity fund actually competes.12:11–14:22 · Guest teaching 4/10 Angel Investment Philosophy and Pattern Recognition Harry asks Justin about his personal angel investing rules and how his decision-making evolved since 2012. Justin explains how his pattern recognition shifted away from market-size thesis toward evaluating founder execution capability.14:22–17:44 · Guest teaching 4/10 Scaling Y Combinator Batches and Managing Founder Needs Harry asks how YC scales batch size while preserving mentorship quality and asks if any competing brand outperforms YC. Justin outlines YC's sharded group structure and enumerates the three core pillars of investor success.17:44–25:07 · Guest teaching 5/10 Leveraging Snapchat for Startup and Fitness Advice During Snapchat talk and quickfire questions, Justin offers candid, contrarian opinions, notably asserting that VC is an easy job because VCs do not do real work. Harry listens and mildly probes, acknowledging Justin's provocative stance in the outro.1:59–7:33 · Guest disagreement 1/10 Justin Kan's Entrepreneurial Journey and Path to YC Justin provides a lengthy summary of his entrepreneurial path from Kiko to Justin.tv, Socialcam, and Twitch's sale to Amazon. Harry maintains an encouraging, light banter role, interjecting briefly with a joke about the acquisition price missing the $1B mark.7:34–12:10 · Guest disagreement 3/10 Evolution of YC Interviews and the Venture Capital Landscape Harry demonstrates strong industry context by quoting Sam Altman's Stanford lecture about older VCs and probing whether YC's $700M Continuity Fund directly competes with traditional venture firms. Justin reframes YC's emergence through classical disruption theory and clarifies where the continuity fund actually competes.12:11–14:22 · Guest disagreement 1/10 Angel Investment Philosophy and Pattern Recognition Harry asks Justin about his personal angel investing rules and how his decision-making evolved since 2012. Justin explains how his pattern recognition shifted away from market-size thesis toward evaluating founder execution capability.14:22–17:44 · Guest disagreement 2/10 Scaling Y Combinator Batches and Managing Founder Needs Harry asks how YC scales batch size while preserving mentorship quality and asks if any competing brand outperforms YC. Justin outlines YC's sharded group structure and enumerates the three core pillars of investor success.17:44–25:07 · Guest disagreement 3/10 Leveraging Snapchat for Startup and Fitness Advice During Snapchat talk and quickfire questions, Justin offers candid, contrarian opinions, notably asserting that VC is an easy job because VCs do not do real work. Harry listens and mildly probes, acknowledging Justin's provocative stance in the outro.1:59–7:33 · Harry pushing back 1/10 Justin Kan's Entrepreneurial Journey and Path to YC Justin provides a lengthy summary of his entrepreneurial path from Kiko to Justin.tv, Socialcam, and Twitch's sale to Amazon. Harry maintains an encouraging, light banter role, interjecting briefly with a joke about the acquisition price missing the $1B mark.7:34–12:10 · Harry pushing back 5/10 Evolution of YC Interviews and the Venture Capital Landscape Harry demonstrates strong industry context by quoting Sam Altman's Stanford lecture about older VCs and probing whether YC's $700M Continuity Fund directly competes with traditional venture firms. Justin reframes YC's emergence through classical disruption theory and clarifies where the continuity fund actually competes.12:11–14:22 · Harry pushing back 2/10 Angel Investment Philosophy and Pattern Recognition Harry asks Justin about his personal angel investing rules and how his decision-making evolved since 2012. Justin explains how his pattern recognition shifted away from market-size thesis toward evaluating founder execution capability.14:22–17:44 · Harry pushing back 3/10 Scaling Y Combinator Batches and Managing Founder Needs Harry asks how YC scales batch size while preserving mentorship quality and asks if any competing brand outperforms YC. Justin outlines YC's sharded group structure and enumerates the three core pillars of investor success.17:44–25:07 · Harry pushing back 2/10 Leveraging Snapchat for Startup and Fitness Advice During Snapchat talk and quickfire questions, Justin offers candid, contrarian opinions, notably asserting that VC is an easy job because VCs do not do real work. Harry listens and mildly probes, acknowledging Justin's provocative stance in the outro.

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

0:00 · Harry 68.5% · guest 31.5%0:00 · Harry 68.5% · guest 31.5%3:00 · Harry 0.9% · guest 99.1%3:00 · Harry 0.9% · guest 99.1%6:00 · Harry 19.1% · guest 80.9%6:00 · Harry 19.1% · guest 80.9%9:00 · Harry 34.9% · guest 65.1%9:00 · Harry 34.9% · guest 65.1%12:00 · Harry 30.7% · guest 69.3%12:00 · Harry 30.7% · guest 69.3%15:00 · Harry 24.7% · guest 75.3%15:00 · Harry 24.7% · guest 75.3%18:00 · Harry 12% · guest 88%18:00 · Harry 12% · guest 88%21:00 · Harry 19.1% · guest 80.9%21:00 · Harry 19.1% · guest 80.9%24:00 · Harry 61.4% · guest 38.6%24:00 · Harry 61.4% · guest 38.6%
Sharpest disagreement ▶ 23:04 Justin dismisses VC difficulty and workload

Justin forcefully rejects the premise that VC work is stressful or difficult, claiming VCs do not do any real work and calling it an easy job if you remain stoic.

 Hardest push from Harry ▶ 10:43 Harry questions YC's Continuity Fund as VC competition

Harry refuses Justin's polite framing that YC is purely synergistic with VCs, pressing him on whether YC's $700M growth fund acts as direct market competition.

 Biggest teaching moment ▶ 9:27 Justin explains YC's rise via market disruption theory

Justin reframes Harry's question about VC complacency by delivering a clear explanation of classical low-cost disruption driven by AWS and cheaper software distribution.

 Harry holds his own ▶ 8:58 Harry quotes Sam Altman's Stanford course on VC complacency

Harry shows deep knowledge of YC history and theory by citing Sam Altman's lecture in Greylock's Stanford course to challenge Justin on VC industry dynamics.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Justin Kan's Entrepreneurial Journey and Path to YC 2311 Justin provides a lengthy summary of his entrepreneurial path from Kiko to Justin.tv, Socialcam, and Twitch's sale to Amazon. Harry maintains an encouraging, light banter role, interjecting briefly with a joke about the acquisition price missing the $1B mark.
Evolution of YC Interviews and the Venture Capital Landscape 6535 Harry demonstrates strong industry context by quoting Sam Altman's Stanford lecture about older VCs and probing whether YC's $700M Continuity Fund directly competes with traditional venture firms. Justin reframes YC's emergence through classical disruption theory and clarifies where the continuity fund actually competes.
Angel Investment Philosophy and Pattern Recognition 3412 Harry asks Justin about his personal angel investing rules and how his decision-making evolved since 2012. Justin explains how his pattern recognition shifted away from market-size thesis toward evaluating founder execution capability.
Scaling Y Combinator Batches and Managing Founder Needs 4423 Harry asks how YC scales batch size while preserving mentorship quality and asks if any competing brand outperforms YC. Justin outlines YC's sharded group structure and enumerates the three core pillars of investor success.
Leveraging Snapchat for Startup and Fitness Advice 3532 During Snapchat talk and quickfire questions, Justin offers candid, contrarian opinions, notably asserting that VC is an easy job because VCs do not do real work. Harry listens and mildly probes, acknowledging Justin's provocative stance in the outro.

Statements from this episode (9)

Assertion Supported
Justin Kan Sold Web Calendar Startup Kiko on eBay for $250,000
“Ended up selling on eBay. Decided startups weren't quite as bad as we'd thought because from the eBay sale, which was about a quarter of a million dollars, we made a little bit of money.”
Justin Kan Aug 1, 2016 ▶ 4:42
Assertion Supported
Amazon's Twitch Acquisition Exceeded $1 Billion After Employee Retention Packages
“We ended up selling to Twitch To Amazon for nine or seventy million dollars. Does that annoy you that it's not a billion? I think they specifically did that, but you know, it's after retention, it was over a billion”
Justin Kan Aug 1, 2016 ▶ 6:48
Assertion Supported
Y Combinator Shortened Founder Interviews From 40 Minutes to 10 Minutes
“So the interviews when they started off were 40 minutes long, which I'm sure to the interviewers felt exhausting. Now they're only 10 minutes long and they still feel exhausting.”
Justin Kan Aug 1, 2016 ▶ 7:58
Assertion Supported
YC Continuity Fund Was Designed to Compete With Public Market Investors
“The continuity fund originally was conceived of as a way to compete with more of the growth stage investors that were coming into the market in the later stage. So that's people who weren't actually classically VCs. I think as you've seen like tech companies, …”
Justin Kan Aug 1, 2016 ▶ 11:01
Insight
Justin Kan: Successful Investors Need Platform, Selection Thesis, and Relentless Pursuit
“Well, I think investors have to have, you know, there's three qualities of investors that I, or of investors or firms that I think are important investing. I've thought about this a little bit. The first one is a platform that generates leads for them or reaso…”
Justin Kan Aug 1, 2016 ▶ 16:03
Opinion
Justin Kan: Snapchat Is the Most Compelling Product of the Past Decade
“Their product teams are like pretty good and they've Really built a, what I think is the most compelling product I've seen in the last 10 years.”
Justin Kan Aug 1, 2016 ▶ 19:35
Insight
Justin Kan: When Faced With Only Bad Choices, Doing Nothing Is Optimal
“One of them is that you don't actually necessarily have to do anything. When you don't have a good decision, when you're faced between multiple bad decisions, maybe you should just do nothing and wait and see what happens.”
Justin Kan Aug 1, 2016 ▶ 20:14
Opinion
Justin Kan Defends Zenefits Founder Parker Conrad as an Impressive Leader
“I always think that he is like a very impressive founder and someone who is like relentlessly bent on growing his company.”
Justin Kan Aug 1, 2016 ▶ 21:17
Insight
Justin Kan: Venture Capital Is Easy Because VCs Do No Real Work
“Because you don't do any of the real work. You know, like, this is, I can, I talk to founders all day, and I give them my advice, and they either do it or they don't do it. But at the end of the day, you know, I, you don't have any control. And so you wait, se…”
Justin Kan Aug 1, 2016 ▶ 23:04
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