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Jun 12, 2017 · 34m · 20vc

20VC: Kevin Rose on Putting The Entire Fund Into Uber, The Future For Mobile & Whether Angels Should Have Super Pro-Rata Rights?

Kevin Rose · 23m spoken Harry Stebbings · 9m spoken
0:00 / 0:00

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In this episode of The 20 Minute VC, host Harry Stebbings interviews serial entrepreneur and venture partner Kevin Rose about his transition from angel investing to institutional venture capital, high-conviction deal structures like Google Ventures' investment in Uber, tech sector perspectives, and founder wellness.

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 28.7% of the talking time here. How this is scored →

Harry as informed peer 3.3 Guest teaching 3.3 Guest disagreement 1.6 Harry pushing back 3.0
05100:0010:0020:0030:002:36–5:11 · Harry as informed peer 1/10 Kevin Rose's Transition from Angel Investor to VC Harry introduces Kevin and asks standard background questions about his foray into venture capital. Kevin comfortably walks through his progression from web 2.0 founder to advisory roles and small angel checks.5:11–8:24 · Harry as informed peer 4/10 Institutional VC Decision-Making and the Uber Investment Strategy Harry presses Kevin on portfolio theory when Kevin mentions Google Ventures put an entire annual fund into Uber. Kevin explains how GV's annual $300M checkbook refresh altered traditional portfolio construction logic.8:24–11:05 · Harry as informed peer 3/10 Public vs. Private Market Investing Strategy Harry asks about Kevin's dual strategy across public and private markets and asks how he handles market timing. Kevin outlines his long-term 5-10 year horizon and dollar-cost averaging strategy.11:05–13:39 · Harry as informed peer 3/10 Pro-Rata Rights and Bearish Stance on Virtual Reality Harry brings up potential founder friction around pro-rata rights before shifting to Kevin's bearish stance on VR. Kevin strongly criticizes VR as isolating and clunky compared to AR.13:39–18:10 · Harry as informed peer 5/10 The Mobile Ecosystem, Recommendation Engines, and Niche Growth Harry cites opposing perspectives from Bessemer's Jeremy Levine and Goodwater Capital to question mobile distribution limits. Kevin reframes the premise by demonstrating how modern recommendation engines allow niche products to thrive.18:10–24:52 · Harry as informed peer 5/10 Insights from Podcasting and Founder Mental Health Harry directly challenges Kevin's argument that VCs should remove pressure from founders, contending that fear of failure drives peak performance. Kevin explicitly rejects Harry's framing, advocating for sustainable long-term pacing over burnout.24:52–33:02 · Harry as informed peer 2/10 Quick Fire Round: Biohacking, Essentialism, Mentors, and Investments Harry guides Kevin through a quick-fire round covering biohacking, essentialism, key mentors, and recent startup investments. The dynamic is collaborative and conversational.2:36–5:11 · Guest teaching 1/10 Kevin Rose's Transition from Angel Investor to VC Harry introduces Kevin and asks standard background questions about his foray into venture capital. Kevin comfortably walks through his progression from web 2.0 founder to advisory roles and small angel checks.5:11–8:24 · Guest teaching 4/10 Institutional VC Decision-Making and the Uber Investment Strategy Harry presses Kevin on portfolio theory when Kevin mentions Google Ventures put an entire annual fund into Uber. Kevin explains how GV's annual $300M checkbook refresh altered traditional portfolio construction logic.8:24–11:05 · Guest teaching 3/10 Public vs. Private Market Investing Strategy Harry asks about Kevin's dual strategy across public and private markets and asks how he handles market timing. Kevin outlines his long-term 5-10 year horizon and dollar-cost averaging strategy.11:05–13:39 · Guest teaching 3/10 Pro-Rata Rights and Bearish Stance on Virtual Reality Harry brings up potential founder friction around pro-rata rights before shifting to Kevin's bearish stance on VR. Kevin strongly criticizes VR as isolating and clunky compared to AR.13:39–18:10 · Guest teaching 5/10 The Mobile Ecosystem, Recommendation Engines, and Niche Growth Harry cites opposing perspectives from Bessemer's Jeremy Levine and Goodwater Capital to question mobile distribution limits. Kevin reframes the premise by demonstrating how modern recommendation engines allow niche products to thrive.18:10–24:52 · Guest teaching 5/10 Insights from Podcasting and Founder Mental Health Harry directly challenges Kevin's argument that VCs should remove pressure from founders, contending that fear of failure drives peak performance. Kevin explicitly rejects Harry's framing, advocating for sustainable long-term pacing over burnout.24:52–33:02 · Guest teaching 2/10 Quick Fire Round: Biohacking, Essentialism, Mentors, and Investments Harry guides Kevin through a quick-fire round covering biohacking, essentialism, key mentors, and recent startup investments. The dynamic is collaborative and conversational.2:36–5:11 · Guest disagreement 0/10 Kevin Rose's Transition from Angel Investor to VC Harry introduces Kevin and asks standard background questions about his foray into venture capital. Kevin comfortably walks through his progression from web 2.0 founder to advisory roles and small angel checks.5:11–8:24 · Guest disagreement 1/10 Institutional VC Decision-Making and the Uber Investment Strategy Harry presses Kevin on portfolio theory when Kevin mentions Google Ventures put an entire annual fund into Uber. Kevin explains how GV's annual $300M checkbook refresh altered traditional portfolio construction logic.8:24–11:05 · Guest disagreement 1/10 Public vs. Private Market Investing Strategy Harry asks about Kevin's dual strategy across public and private markets and asks how he handles market timing. Kevin outlines his long-term 5-10 year horizon and dollar-cost averaging strategy.11:05–13:39 · Guest disagreement 3/10 Pro-Rata Rights and Bearish Stance on Virtual Reality Harry brings up potential founder friction around pro-rata rights before shifting to Kevin's bearish stance on VR. Kevin strongly criticizes VR as isolating and clunky compared to AR.13:39–18:10 · Guest disagreement 2/10 The Mobile Ecosystem, Recommendation Engines, and Niche Growth Harry cites opposing perspectives from Bessemer's Jeremy Levine and Goodwater Capital to question mobile distribution limits. Kevin reframes the premise by demonstrating how modern recommendation engines allow niche products to thrive.18:10–24:52 · Guest disagreement 4/10 Insights from Podcasting and Founder Mental Health Harry directly challenges Kevin's argument that VCs should remove pressure from founders, contending that fear of failure drives peak performance. Kevin explicitly rejects Harry's framing, advocating for sustainable long-term pacing over burnout.24:52–33:02 · Guest disagreement 0/10 Quick Fire Round: Biohacking, Essentialism, Mentors, and Investments Harry guides Kevin through a quick-fire round covering biohacking, essentialism, key mentors, and recent startup investments. The dynamic is collaborative and conversational.2:36–5:11 · Harry pushing back 0/10 Kevin Rose's Transition from Angel Investor to VC Harry introduces Kevin and asks standard background questions about his foray into venture capital. Kevin comfortably walks through his progression from web 2.0 founder to advisory roles and small angel checks.5:11–8:24 · Harry pushing back 5/10 Institutional VC Decision-Making and the Uber Investment Strategy Harry presses Kevin on portfolio theory when Kevin mentions Google Ventures put an entire annual fund into Uber. Kevin explains how GV's annual $300M checkbook refresh altered traditional portfolio construction logic.8:24–11:05 · Harry pushing back 2/10 Public vs. Private Market Investing Strategy Harry asks about Kevin's dual strategy across public and private markets and asks how he handles market timing. Kevin outlines his long-term 5-10 year horizon and dollar-cost averaging strategy.11:05–13:39 · Harry pushing back 3/10 Pro-Rata Rights and Bearish Stance on Virtual Reality Harry brings up potential founder friction around pro-rata rights before shifting to Kevin's bearish stance on VR. Kevin strongly criticizes VR as isolating and clunky compared to AR.13:39–18:10 · Harry pushing back 4/10 The Mobile Ecosystem, Recommendation Engines, and Niche Growth Harry cites opposing perspectives from Bessemer's Jeremy Levine and Goodwater Capital to question mobile distribution limits. Kevin reframes the premise by demonstrating how modern recommendation engines allow niche products to thrive.18:10–24:52 · Harry pushing back 6/10 Insights from Podcasting and Founder Mental Health Harry directly challenges Kevin's argument that VCs should remove pressure from founders, contending that fear of failure drives peak performance. Kevin explicitly rejects Harry's framing, advocating for sustainable long-term pacing over burnout.24:52–33:02 · Harry pushing back 1/10 Quick Fire Round: Biohacking, Essentialism, Mentors, and Investments Harry guides Kevin through a quick-fire round covering biohacking, essentialism, key mentors, and recent startup investments. The dynamic is collaborative and conversational.

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

0:00 · Harry 94.6% · guest 5.4%0:00 · Harry 94.6% · guest 5.4%3:00 · Harry 12.7% · guest 87.3%3:00 · Harry 12.7% · guest 87.3%6:00 · Harry 21.1% · guest 78.9%6:00 · Harry 21.1% · guest 78.9%9:00 · Harry 20.7% · guest 79.3%9:00 · Harry 20.7% · guest 79.3%12:00 · Harry 21.3% · guest 78.7%12:00 · Harry 21.3% · guest 78.7%15:00 · Harry 6.1% · guest 93.9%15:00 · Harry 6.1% · guest 93.9%18:00 · Harry 30.1% · guest 69.9%18:00 · Harry 30.1% · guest 69.9%21:00 · Harry 20.6% · guest 79.4%21:00 · Harry 20.6% · guest 79.4%24:00 · Harry 24.9% · guest 75.1%24:00 · Harry 24.9% · guest 75.1%27:00 · Harry 4.8% · guest 95.2%27:00 · Harry 4.8% · guest 95.2%30:00 · Harry 17.7% · guest 82.3%30:00 · Harry 17.7% · guest 82.3%33:00 · Harry 98.7% · guest 1.3%33:00 · Harry 98.7% · guest 1.3%
Sharpest disagreement ▶ 22:22 Kevin rejecting fear of failure as a motivator

Kevin directly counters Harry's premise that fear of failure is required for founder success, arguing that constant sprint pressure damages long-term execution.

 Hardest push from Harry ▶ 21:55 Harry challenging the removal of failure pressure

Harry explicitly pushes back against Kevin's philosophy, arguing that eliminating failure pressure replaces drive with comfort.

 Biggest teaching moment ▶ 7:05 Kevin explaining GV's annual fund structure for Uber

When Harry questions whether concentrating a fund into Uber violates portfolio theory, Kevin educates him on how Google Ventures' annual checkbook refresh changed their investment math.

 Harry holds his own ▶ 13:39 Harry citing opposing VC market perspectives on mobile

Harry demonstrates strong industry knowledge by contrasting contradictory stances from Bessemer's Jeremy Levine and Goodwater Capital to challenge Kevin on mobile app distribution.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Kevin Rose's Transition from Angel Investor to VC 1100 Harry introduces Kevin and asks standard background questions about his foray into venture capital. Kevin comfortably walks through his progression from web 2.0 founder to advisory roles and small angel checks.
Institutional VC Decision-Making and the Uber Investment Strategy 4415 Harry presses Kevin on portfolio theory when Kevin mentions Google Ventures put an entire annual fund into Uber. Kevin explains how GV's annual $300M checkbook refresh altered traditional portfolio construction logic.
Public vs. Private Market Investing Strategy 3312 Harry asks about Kevin's dual strategy across public and private markets and asks how he handles market timing. Kevin outlines his long-term 5-10 year horizon and dollar-cost averaging strategy.
Pro-Rata Rights and Bearish Stance on Virtual Reality 3333 Harry brings up potential founder friction around pro-rata rights before shifting to Kevin's bearish stance on VR. Kevin strongly criticizes VR as isolating and clunky compared to AR.
The Mobile Ecosystem, Recommendation Engines, and Niche Growth 5524 Harry cites opposing perspectives from Bessemer's Jeremy Levine and Goodwater Capital to question mobile distribution limits. Kevin reframes the premise by demonstrating how modern recommendation engines allow niche products to thrive.
Insights from Podcasting and Founder Mental Health 5546 Harry directly challenges Kevin's argument that VCs should remove pressure from founders, contending that fear of failure drives peak performance. Kevin explicitly rejects Harry's framing, advocating for sustainable long-term pacing over burnout.
Quick Fire Round: Biohacking, Essentialism, Mentors, and Investments 2201 Harry guides Kevin through a quick-fire round covering biohacking, essentialism, key mentors, and recent startup investments. The dynamic is collaborative and conversational.

Statements from this episode (10)

Assertion Supported
Kevin Rose: GV deployed its entire $254M annual fund into Uber
“I definitely know that largest GVs ever done is Uber, where it was two hundred and fifty four million, I believe. So it was our entire fund into one of their rounds.”
Kevin Rose Jun 12, 2017 ▶ 6:55
Assertion Supported
Kevin Rose: GV operated on an annually refreshed $300M allocation
“GB was a little bit different than your typical fund that is invested over the course of two to three years, whereas ours was refreshed annually. So we had a brand new you know, three hundred million dollar checkbook come January first.”
Kevin Rose Jun 12, 2017 ▶ 7:57
Prediction Not checkable as stated
Kevin Rose refuses to invest in cryptocurrencies that merely tweak Bitcoin
“I'm not going to buy into a cryptocurrency that is just a somewhat slightly version or somewhat slightly tweaked version of Bitcoin. It has to be something that is truly novel and unique”
Kevin Rose Jun 12, 2017 ▶ 10:31
Disclosure
Kevin Rose pushes for super pro-rata rights in follow-on funding rounds
“When I'm getting into those markets, I'll place kind of smallish bets initially, and then as I see progress, continue to increase those over time. And that's part of the reason why I go for pro rata rights as an angel, and oftentimes push for kind of a super p…”
Kevin Rose Jun 12, 2017 ▶ 10:49
Opinion
Kevin Rose: Pro-rata rights for angel investors are rarely contentious
“I mean, not everyone's going to want to give it to you, but you know, we're talking small dollars here, so it's not like you're kind of taking up a large round. Right, exactly. So it's not that big a deal.”
Kevin Rose Jun 12, 2017 ▶ 11:16
Opinion
Kevin Rose: Virtual reality is a passing fad
“I've always disliked virtual reality. I've never been a fan of it. I wrote a blog post on a medium here, I guess a year and a half, two years ago about just virtual reality being a fad.”
Kevin Rose Jun 12, 2017 ▶ 11:41
Disclosure
Kevin Rose's free fasting app reached #1 and logged 700k fasts
“Yeah. So, you know, it was just a simple little free app and we were able to quickly kind of shoot up in the rankings inside of the app store for the word fasting. So now if you go into the app store and Apple and type in fasting, we're kind of the number one …”
Kevin Rose Jun 12, 2017 ▶ 17:16
Insight
Kevin Rose: 24/7 hustle causes founder burnout and hurts long-term success
“If you're burning the kind of midnight oil, and you're staying up, and you're pushing your entire team extremely hard, it's okay to do that in very small, small Sprints, but I don't believe that is taking the long-term view. I think that I want my founders not…”
Kevin Rose Jun 12, 2017 ▶ 22:27
Insight
Kevin Rose: Struggling to admit ignorance is a major founder handicap
“I think that the hardest thing for anyone is really to admit that you know, you don't know something. I think that's really hard for brilliant founders, and it can be a big crutch”
Kevin Rose Jun 12, 2017 ▶ 30:50
Disclosure
Kevin Rose is investing in former Google HR head Laszlo Bock's startup
“Laszlo Bach, who was basically ran human resources at Google for 10 years, 10 plus years. He recently left Google about a year ago, and he has a new startup that I'll be investing in as well.”
Kevin Rose Jun 12, 2017 ▶ 32:36
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