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Jan 25, 2017 · 26m · 20vc

20VC: Preparing For The Next Big Trend, Why Conversational Will Be The Next Big Thing & How Entrepreneurs Should View Market Size with Sarah Guo @ Greylock Partners

Sarah Guo · 17m spoken Harry Stebbings · 7m spoken
0:00 / 0:00

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In this episode of The 20 Minute VC, host Harry Stebbings interviews Greylock Partners investor Sarah Guo about her career path from Goldman Sachs to venture capital, key frameworks for evaluating early-stage enterprise startups, and emerging technology trends across artificial intelligence and greenfield industry verticals.

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 30.7% of the talking time here. How this is scored →

Harry as informed peer 2.2 Guest teaching 3.5 Guest disagreement 1.0 Harry pushing back 1.2
05100:0010:0020:002:08–4:58 · Harry as informed peer 1/10 Sarah Guo's Origin Story and Path to Greylock Harry opens with a standard biographical prompt asking Sarah about her path to Greylock. Sarah shares her background working at Casa Systems as a teen, her experience at Goldman Sachs, and how meeting Anil Bhusri led her to Greylock.4:58–8:17 · Harry as informed peer 2/10 Learnings from Taking Tech Companies Public Harry brings a question from partner Josh Elman about learnings from Workday's IPO. Sarah explains how public readiness requires clear narrative and market size, prompting Harry to ask for a specific example of exceptional narrative framing.8:17–13:01 · Harry as informed peer 3/10 Identifying the Next Technological Platform Shift Harry asks about the next platform shift after mobile and cloud. Sarah reframes the question using Elad Gil's work to distinguish technical enablers from distribution ecosystems, and explicitly rejects Harry's suggestion that AI will be sold as 'machine learning in a box'.13:01–17:11 · Harry as informed peer 3/10 Investing in Greenfield Markets and Evaluating Market Size Harry offers an insightful observation comparing market size to valuation as fluid and transient. Sarah introduces her 'neighborhood' framework for market adjacency, and Harry pushes back to ask her to define what she means by 'capital gap'.17:11–20:04 · Harry as informed peer 3/10 The Evolution and Future of Venture Capital Harry asserts a strong view on how VC value-add is evolving beyond Andreessen-style advice. Sarah politely side-steps the direct comment on Andreessen and outlines how Greylock combines software pattern recognition with human relationship building.20:04–24:21 · Harry as informed peer 1/10 Quick-Fire Round: Books, Routines, Mentors, and Rhumbix A quick-fire round covering book recommendations, morning schedules, and recent investments. Sarah details her 4am routine and explains the contrarian thesis behind investing in construction tech startup Rhumbix.2:08–4:58 · Guest teaching 2/10 Sarah Guo's Origin Story and Path to Greylock Harry opens with a standard biographical prompt asking Sarah about her path to Greylock. Sarah shares her background working at Casa Systems as a teen, her experience at Goldman Sachs, and how meeting Anil Bhusri led her to Greylock.4:58–8:17 · Guest teaching 4/10 Learnings from Taking Tech Companies Public Harry brings a question from partner Josh Elman about learnings from Workday's IPO. Sarah explains how public readiness requires clear narrative and market size, prompting Harry to ask for a specific example of exceptional narrative framing.8:17–13:01 · Guest teaching 5/10 Identifying the Next Technological Platform Shift Harry asks about the next platform shift after mobile and cloud. Sarah reframes the question using Elad Gil's work to distinguish technical enablers from distribution ecosystems, and explicitly rejects Harry's suggestion that AI will be sold as 'machine learning in a box'.13:01–17:11 · Guest teaching 4/10 Investing in Greenfield Markets and Evaluating Market Size Harry offers an insightful observation comparing market size to valuation as fluid and transient. Sarah introduces her 'neighborhood' framework for market adjacency, and Harry pushes back to ask her to define what she means by 'capital gap'.17:11–20:04 · Guest teaching 4/10 The Evolution and Future of Venture Capital Harry asserts a strong view on how VC value-add is evolving beyond Andreessen-style advice. Sarah politely side-steps the direct comment on Andreessen and outlines how Greylock combines software pattern recognition with human relationship building.20:04–24:21 · Guest teaching 2/10 Quick-Fire Round: Books, Routines, Mentors, and Rhumbix A quick-fire round covering book recommendations, morning schedules, and recent investments. Sarah details her 4am routine and explains the contrarian thesis behind investing in construction tech startup Rhumbix.2:08–4:58 · Guest disagreement 0/10 Sarah Guo's Origin Story and Path to Greylock Harry opens with a standard biographical prompt asking Sarah about her path to Greylock. Sarah shares her background working at Casa Systems as a teen, her experience at Goldman Sachs, and how meeting Anil Bhusri led her to Greylock.4:58–8:17 · Guest disagreement 0/10 Learnings from Taking Tech Companies Public Harry brings a question from partner Josh Elman about learnings from Workday's IPO. Sarah explains how public readiness requires clear narrative and market size, prompting Harry to ask for a specific example of exceptional narrative framing.8:17–13:01 · Guest disagreement 2/10 Identifying the Next Technological Platform Shift Harry asks about the next platform shift after mobile and cloud. Sarah reframes the question using Elad Gil's work to distinguish technical enablers from distribution ecosystems, and explicitly rejects Harry's suggestion that AI will be sold as 'machine learning in a box'.13:01–17:11 · Guest disagreement 1/10 Investing in Greenfield Markets and Evaluating Market Size Harry offers an insightful observation comparing market size to valuation as fluid and transient. Sarah introduces her 'neighborhood' framework for market adjacency, and Harry pushes back to ask her to define what she means by 'capital gap'.17:11–20:04 · Guest disagreement 2/10 The Evolution and Future of Venture Capital Harry asserts a strong view on how VC value-add is evolving beyond Andreessen-style advice. Sarah politely side-steps the direct comment on Andreessen and outlines how Greylock combines software pattern recognition with human relationship building.20:04–24:21 · Guest disagreement 1/10 Quick-Fire Round: Books, Routines, Mentors, and Rhumbix A quick-fire round covering book recommendations, morning schedules, and recent investments. Sarah details her 4am routine and explains the contrarian thesis behind investing in construction tech startup Rhumbix.2:08–4:58 · Harry pushing back 0/10 Sarah Guo's Origin Story and Path to Greylock Harry opens with a standard biographical prompt asking Sarah about her path to Greylock. Sarah shares her background working at Casa Systems as a teen, her experience at Goldman Sachs, and how meeting Anil Bhusri led her to Greylock.4:58–8:17 · Harry pushing back 1/10 Learnings from Taking Tech Companies Public Harry brings a question from partner Josh Elman about learnings from Workday's IPO. Sarah explains how public readiness requires clear narrative and market size, prompting Harry to ask for a specific example of exceptional narrative framing.8:17–13:01 · Harry pushing back 2/10 Identifying the Next Technological Platform Shift Harry asks about the next platform shift after mobile and cloud. Sarah reframes the question using Elad Gil's work to distinguish technical enablers from distribution ecosystems, and explicitly rejects Harry's suggestion that AI will be sold as 'machine learning in a box'.13:01–17:11 · Harry pushing back 2/10 Investing in Greenfield Markets and Evaluating Market Size Harry offers an insightful observation comparing market size to valuation as fluid and transient. Sarah introduces her 'neighborhood' framework for market adjacency, and Harry pushes back to ask her to define what she means by 'capital gap'.17:11–20:04 · Harry pushing back 2/10 The Evolution and Future of Venture Capital Harry asserts a strong view on how VC value-add is evolving beyond Andreessen-style advice. Sarah politely side-steps the direct comment on Andreessen and outlines how Greylock combines software pattern recognition with human relationship building.20:04–24:21 · Harry pushing back 0/10 Quick-Fire Round: Books, Routines, Mentors, and Rhumbix A quick-fire round covering book recommendations, morning schedules, and recent investments. Sarah details her 4am routine and explains the contrarian thesis behind investing in construction tech startup Rhumbix.

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

0:00 · Harry 88.3% · guest 11.7%0:00 · Harry 88.3% · guest 11.7%3:00 · Harry 7.2% · guest 92.8%3:00 · Harry 7.2% · guest 92.8%6:00 · Harry 18.6% · guest 81.4%6:00 · Harry 18.6% · guest 81.4%9:00 · Harry 20.4% · guest 79.6%9:00 · Harry 20.4% · guest 79.6%12:00 · Harry 23.1% · guest 76.9%12:00 · Harry 23.1% · guest 76.9%15:00 · Harry 20.8% · guest 79.2%15:00 · Harry 20.8% · guest 79.2%18:00 · Harry 15.3% · guest 84.7%18:00 · Harry 15.3% · guest 84.7%21:00 · Harry 10.3% · guest 89.7%21:00 · Harry 10.3% · guest 89.7%24:00 · Harry 82.6% · guest 17.4%24:00 · Harry 82.6% · guest 17.4%
Sharpest disagreement ▶ 9:51 Refuting 'AI in a Box'

Sarah directly rejects Harry's premise that AI will be sold as a turnkey 'Oracle solution in a box', explaining that domain expertise and custom system design make generic turnkey AI products unrealistic.

 Hardest push from Harry ▶ 15:43 Challenging 'Capital Gap' Jargon

Harry interrupts the discussion flow to explicitly challenge Sarah to define what she means by 'capital gap', refusing to let venture jargon pass without clarification.

 Biggest teaching moment ▶ 8:35 Platform Shifts vs Enabling Technologies

Sarah corrects the premise of Harry's question by breaking down the distinction between enabling technologies like AI and actual distribution/ecosystem platforms like mobile and cloud.

 Harry holds his own ▶ 14:11 Re-framing Market Size as Dynamic

Harry demonstrates strong market expertise by arguing that market size is fluid and transient like valuation, citing ephemeral messaging to challenge traditional static market evaluation.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Sarah Guo's Origin Story and Path to Greylock 1200 Harry opens with a standard biographical prompt asking Sarah about her path to Greylock. Sarah shares her background working at Casa Systems as a teen, her experience at Goldman Sachs, and how meeting Anil Bhusri led her to Greylock.
Learnings from Taking Tech Companies Public 2401 Harry brings a question from partner Josh Elman about learnings from Workday's IPO. Sarah explains how public readiness requires clear narrative and market size, prompting Harry to ask for a specific example of exceptional narrative framing.
Identifying the Next Technological Platform Shift 3522 Harry asks about the next platform shift after mobile and cloud. Sarah reframes the question using Elad Gil's work to distinguish technical enablers from distribution ecosystems, and explicitly rejects Harry's suggestion that AI will be sold as 'machine learning in a box'.
Investing in Greenfield Markets and Evaluating Market Size 3412 Harry offers an insightful observation comparing market size to valuation as fluid and transient. Sarah introduces her 'neighborhood' framework for market adjacency, and Harry pushes back to ask her to define what she means by 'capital gap'.
The Evolution and Future of Venture Capital 3422 Harry asserts a strong view on how VC value-add is evolving beyond Andreessen-style advice. Sarah politely side-steps the direct comment on Andreessen and outlines how Greylock combines software pattern recognition with human relationship building.
Quick-Fire Round: Books, Routines, Mentors, and Rhumbix 1210 A quick-fire round covering book recommendations, morning schedules, and recent investments. Sarah details her 4am routine and explains the contrarian thesis behind investing in construction tech startup Rhumbix.

Statements from this episode (11)

Insight
Guo: A founder's storytelling ability correlates directly with company success
“And so I am always surprised by how correlated the ability to describe why a company is important and good and winning is to sort of your ability to actually go be those things. Because if you tell the story right, you can get the highest quality people on you…”
Sarah Guo Jan 25, 2017 ▶ 6:12
Assertion Not checkable as stated
Guo: Many startup founders cannot explain why customers buy their product
“And so, like, I, I'm always trying to ask the very direct question of, like, why do customers pay you, or why do people find and want your product? And a lot of founders can't answer that question.”
Sarah Guo Jan 25, 2017 ▶ 6:33
Prediction Not checkable as stated
Guo: Next major tech wave is conversational mixed reality and ubiquitous computing
“What we'll see next that matters is like conversational mixed reality software, more computing nodes everywhere in your house, in your car, in AR and VR.”
Sarah Guo Jan 25, 2017 ▶ 8:58
Insight
Guo: AI is an enabling technology, not a distribution platform
“AI is the enabling technology, but people are talking about AI itself as a platform, but it's not distribution and ecosystem.”
Sarah Guo Jan 25, 2017 ▶ 9:12
Assertion Not checkable as stated
Guo: No Plug-and-Play 'AI in a Box' Exists for Meaningful Applications
“I don't think that there's anything that looks like AI in a box today for applications that matter.”
Sarah Guo Jan 25, 2017 ▶ 9:51
Insight
Guo: Startups Using Public Internet Data Face Incumbent Risk From Big Tech
“If your plan as a company is to take internet accessible data sets and do something interesting with them on the machine learning side and productize them, if it's an area that Google and Facebook care deeply about, you're on dangerous ground, right? They, tho…”
Sarah Guo Jan 25, 2017 ▶ 11:41
Prediction Not checkable as stated
Guo: Building Company-Specific Models with Internal Data Is Defensible AI Opportunity
“I also think an interesting opportunity that we will see is building sort of company specific models with internal data. There's a question of how custom software like and services like these companies get, but if you are building a model that works in a speci…”
Sarah Guo Jan 25, 2017 ▶ 12:31
Insight
Guo: Assess market size by adjacent expansion potential, not initial market
“The way we think of it is, is really about the neighborhood. And what I mean by that is, is there a special team with a tiny toehold that Of value to the user with immediate ROI that they can get wins with, that they can continue to raise capital on, and do th…”
Sarah Guo Jan 25, 2017 ▶ 14:50
Insight
Guo: Startup launch costs have dropped, but scaling costs have risen
“The cost to start one that really matters has come down dramatically in many areas, right? AWS increased seed capital, a cultural shift where it's okay to drop out of school and start a company, three D printing, a bigger sort of supportive ecosystem, you name…”
Sarah Guo Jan 25, 2017 ▶ 18:33
Insight
Guo: Most VC firms are fragile and fail to scale partners
“Most venture firms are pretty fragile. And They don't scale past a certain number of partners historically, and they need to go through constant reinvention.”
Sarah Guo Jan 25, 2017 ▶ 19:27
Insight
Guo: Context Switching in Venture Capital Is Extremely Costly
“The context switching in venture is very costly, right? And so, it's very important to me to have some time when I'm not trying to field emails from people in the portfolio or jump from one meeting on perception for autonomous vehicles to another on developer …”
Sarah Guo Jan 25, 2017 ▶ 20:58
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