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Sep 10, 2018 · 32m · 20vc

20VC: The Biggest Lessons From Working Alongside John Doerr, How To Optimize The Speed of Investment Decision-Making & Why Saying No Graciously Is The Most Important Thing with Shabih Rizvi, Founding Partner @ Gradient Ventures

Shabih "Shabby" Rizvi · 20m spoken Harry Stebbings · 10m spoken
0:00 / 0:00

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In this episode of The 20 Minute VC, host Harry Stebbings interviews Shabih Rizvi, founding partner at Gradient Ventures, to explore key lessons learned working alongside John Doerr, effective founder relationship management, and actionable frameworks for venture deal sourcing and decision velocity.

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 34.9% of the talking time here. How this is scored →

Harry as informed peer 2.6 Guest teaching 3.6 Guest disagreement 0.2 Harry pushing back 0.8
05100:0010:0020:0030:003:23–6:22 · Harry as informed peer 1/10 Shabih Rizvi's Path from Biotech to Venture Capital Harry asks friendly background questions about Shabby's career trajectory and the origin of Gradient Ventures. Shabby outlines his journey from Genentech biotech to AdMob, Google Play, Kleiner Perkins, and finally founding Gradient.6:22–13:56 · Harry as informed peer 3/10 Lessons Learned Working Alongside Venture Legend John Doerr Harry cites Trey from Defy's time with John Doerr to frame a question about board member development. Shabby shares insights on Doerr's cerebral boardroom style and details how staying in touch with the UJet founder eventually led to Kleiner leading their round.13:56–20:01 · Harry as informed peer 4/10 The Art of Saying No Graciously to Founders Harry shares his personal difficulty with saying no to founders and brings up Hunter Walk's concept of dark deal flow. Shabby provides a structured method for gracious rejection and reframes dark deal flow as alumni and proprietary networks rather than something negative.20:01–23:53 · Harry as informed peer 3/10 Pitch Filtering Techniques, Bias Mitigation, and Founder Meetings Harry references pitch filtering techniques and asks how investors avoid cognitive biases after losing money in a sector. Shabby explains how founders can overcome VC biases by demonstrating why market dynamics have changed.23:53–29:35 · Harry as informed peer 2/10 Investment Decision-Making and Velocity at Gradient Ventures Harry guides Shabby through quickfire questions covering decision speed at Gradient, favorite books, and startup ecosystems. Shabby discusses geographical valuation differences and Gradient's focus on velocity.3:23–6:22 · Guest teaching 2/10 Shabih Rizvi's Path from Biotech to Venture Capital Harry asks friendly background questions about Shabby's career trajectory and the origin of Gradient Ventures. Shabby outlines his journey from Genentech biotech to AdMob, Google Play, Kleiner Perkins, and finally founding Gradient.6:22–13:56 · Guest teaching 4/10 Lessons Learned Working Alongside Venture Legend John Doerr Harry cites Trey from Defy's time with John Doerr to frame a question about board member development. Shabby shares insights on Doerr's cerebral boardroom style and details how staying in touch with the UJet founder eventually led to Kleiner leading their round.13:56–20:01 · Guest teaching 5/10 The Art of Saying No Graciously to Founders Harry shares his personal difficulty with saying no to founders and brings up Hunter Walk's concept of dark deal flow. Shabby provides a structured method for gracious rejection and reframes dark deal flow as alumni and proprietary networks rather than something negative.20:01–23:53 · Guest teaching 4/10 Pitch Filtering Techniques, Bias Mitigation, and Founder Meetings Harry references pitch filtering techniques and asks how investors avoid cognitive biases after losing money in a sector. Shabby explains how founders can overcome VC biases by demonstrating why market dynamics have changed.23:53–29:35 · Guest teaching 3/10 Investment Decision-Making and Velocity at Gradient Ventures Harry guides Shabby through quickfire questions covering decision speed at Gradient, favorite books, and startup ecosystems. Shabby discusses geographical valuation differences and Gradient's focus on velocity.3:23–6:22 · Guest disagreement 0/10 Shabih Rizvi's Path from Biotech to Venture Capital Harry asks friendly background questions about Shabby's career trajectory and the origin of Gradient Ventures. Shabby outlines his journey from Genentech biotech to AdMob, Google Play, Kleiner Perkins, and finally founding Gradient.6:22–13:56 · Guest disagreement 0/10 Lessons Learned Working Alongside Venture Legend John Doerr Harry cites Trey from Defy's time with John Doerr to frame a question about board member development. Shabby shares insights on Doerr's cerebral boardroom style and details how staying in touch with the UJet founder eventually led to Kleiner leading their round.13:56–20:01 · Guest disagreement 1/10 The Art of Saying No Graciously to Founders Harry shares his personal difficulty with saying no to founders and brings up Hunter Walk's concept of dark deal flow. Shabby provides a structured method for gracious rejection and reframes dark deal flow as alumni and proprietary networks rather than something negative.20:01–23:53 · Guest disagreement 0/10 Pitch Filtering Techniques, Bias Mitigation, and Founder Meetings Harry references pitch filtering techniques and asks how investors avoid cognitive biases after losing money in a sector. Shabby explains how founders can overcome VC biases by demonstrating why market dynamics have changed.23:53–29:35 · Guest disagreement 0/10 Investment Decision-Making and Velocity at Gradient Ventures Harry guides Shabby through quickfire questions covering decision speed at Gradient, favorite books, and startup ecosystems. Shabby discusses geographical valuation differences and Gradient's focus on velocity.3:23–6:22 · Harry pushing back 0/10 Shabih Rizvi's Path from Biotech to Venture Capital Harry asks friendly background questions about Shabby's career trajectory and the origin of Gradient Ventures. Shabby outlines his journey from Genentech biotech to AdMob, Google Play, Kleiner Perkins, and finally founding Gradient.6:22–13:56 · Harry pushing back 1/10 Lessons Learned Working Alongside Venture Legend John Doerr Harry cites Trey from Defy's time with John Doerr to frame a question about board member development. Shabby shares insights on Doerr's cerebral boardroom style and details how staying in touch with the UJet founder eventually led to Kleiner leading their round.13:56–20:01 · Harry pushing back 2/10 The Art of Saying No Graciously to Founders Harry shares his personal difficulty with saying no to founders and brings up Hunter Walk's concept of dark deal flow. Shabby provides a structured method for gracious rejection and reframes dark deal flow as alumni and proprietary networks rather than something negative.20:01–23:53 · Harry pushing back 1/10 Pitch Filtering Techniques, Bias Mitigation, and Founder Meetings Harry references pitch filtering techniques and asks how investors avoid cognitive biases after losing money in a sector. Shabby explains how founders can overcome VC biases by demonstrating why market dynamics have changed.23:53–29:35 · Harry pushing back 0/10 Investment Decision-Making and Velocity at Gradient Ventures Harry guides Shabby through quickfire questions covering decision speed at Gradient, favorite books, and startup ecosystems. Shabby discusses geographical valuation differences and Gradient's focus on velocity.

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

0:00 · Harry 100% · guest 0%0:00 · Harry 100% · guest 0%3:00 · Harry 25.4% · guest 74.6%3:00 · Harry 25.4% · guest 74.6%6:00 · Harry 25.3% · guest 74.7%6:00 · Harry 25.3% · guest 74.7%9:00 · Harry 5.4% · guest 94.6%9:00 · Harry 5.4% · guest 94.6%12:00 · Harry 18.6% · guest 81.4%12:00 · Harry 18.6% · guest 81.4%15:00 · Harry 23.9% · guest 76.1%15:00 · Harry 23.9% · guest 76.1%18:00 · Harry 17.8% · guest 82.2%18:00 · Harry 17.8% · guest 82.2%21:00 · Harry 25.9% · guest 74.1%21:00 · Harry 25.9% · guest 74.1%24:00 · Harry 20.9% · guest 79.1%24:00 · Harry 20.9% · guest 79.1%27:00 · Harry 33% · guest 67%27:00 · Harry 33% · guest 67%30:00 · Harry 100% · guest 0%30:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 17:08 Reframing Dark Deal Flow

Shabby gently pushes back on Harry's term 'dark deal flow', arguing that the phrase carries an unfairly negative connotation for standard alumni network deal sourcing.

 Hardest push from Harry ▶ 17:08 Challenging the Existence of Dark Deal Flow

Harry questions whether dark deal flow still exists in Silicon Valley given the rise of transparent platforms like AngelList.

 Biggest teaching moment ▶ 14:20 Framework for Saying No Graciously

Shabby lays out a clear multi-step methodology for letting founders down politely, explaining when email, phone calls, or face-to-face meetings are required.

 Harry holds his own ▶ 6:22 Referencing Industry Peer Experiences

Harry displays domain knowledge by bringing up specific takeaways from Trey at Defy regarding John Doerr's mentorship style.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Shabih Rizvi's Path from Biotech to Venture Capital 1200 Harry asks friendly background questions about Shabby's career trajectory and the origin of Gradient Ventures. Shabby outlines his journey from Genentech biotech to AdMob, Google Play, Kleiner Perkins, and finally founding Gradient.
Lessons Learned Working Alongside Venture Legend John Doerr 3401 Harry cites Trey from Defy's time with John Doerr to frame a question about board member development. Shabby shares insights on Doerr's cerebral boardroom style and details how staying in touch with the UJet founder eventually led to Kleiner leading their round.
The Art of Saying No Graciously to Founders 4512 Harry shares his personal difficulty with saying no to founders and brings up Hunter Walk's concept of dark deal flow. Shabby provides a structured method for gracious rejection and reframes dark deal flow as alumni and proprietary networks rather than something negative.
Pitch Filtering Techniques, Bias Mitigation, and Founder Meetings 3401 Harry references pitch filtering techniques and asks how investors avoid cognitive biases after losing money in a sector. Shabby explains how founders can overcome VC biases by demonstrating why market dynamics have changed.
Investment Decision-Making and Velocity at Gradient Ventures 2300 Harry guides Shabby through quickfire questions covering decision speed at Gradient, favorite books, and startup ecosystems. Shabby discusses geographical valuation differences and Gradient's focus on velocity.

Statements from this episode (9)

Opinion
John Doerr combines humility with incisive boardroom problem-solving
“And it was one of the remarkable things about John is just, he lights up a room when he walks in and he's got this incredibly humble personality, but he can really quickly get to the core of a problem or an issue and very quickly start to ask the questions tha…”
Shabih "Shabby" Rizvi Sep 10, 2018 ▶ 7:23
Assertion Not checkable as stated
Snapchat had only 13 employees when Shabih Rizvi first met them
“So I remember when I first met the Snapchat team, it was only about 13 people at the time.”
Shabih "Shabby" Rizvi Sep 10, 2018 ▶ 9:20
Insight
Rocket ship startups face continuous unsolicited investment offers
“Once you sort of hit this special rocket ship status, I would say there's always suitors waiting to come and invest in your company, which of course can be somewhat jarring sometimes for the founders, because many of them want nothing but to build their compan…”
Shabih "Shabby" Rizvi Sep 10, 2018 ▶ 13:17
Insight
Saying no graciously is the most important and difficult part of VC
“I think it's actually the hardest part of the job, because ultimately, as we touched on before, this is a services industry, and when founders come and pitch us, they're sharing their life vision, life dream. They've probably spent countless hours Ridiculous s…”
Shabih "Shabby" Rizvi Sep 10, 2018 ▶ 14:21
Disclosure
Rizvi met Honey co-founder George Ruan through a cold lawyer introduction
“So a couple of years ago, got an introduction through actually a lawyer just out of the blue, got an intro to a founder that was going to be in town from Los Angeles and a little bit of a primer on the company. And I was intrigued. So I responded and ultimatel…”
Shabih "Shabby" Rizvi Sep 10, 2018 ▶ 18:50
Insight
Unclear founder backgrounds or motivations trigger quick rejections at Gradient Ventures
“If they can't explain those two things relatively quickly, if that's not clear in a slide or in an email, then I would say it can be usually be a quick no, but a very polite no.”
Shabih "Shabby" Rizvi Sep 10, 2018 ▶ 20:19
Insight
Top founders deeply study past failures in their startup category
“I found that the best founders that are going after some of these categories, or maybe there have been companies that haven't worked up, have actually made an effort to connect with either people on those teams, or try and understand the story intimately well,…”
Shabih "Shabby" Rizvi Sep 10, 2018 ▶ 22:10
Assertion Not checkable as stated
Gradient Ventures meets twice weekly to accelerate investment decisions
“We get together as a group twice a week. We meet companies on those days. We also do our partner discussions those days. And so we have a pretty nimble and velocity oriented process.”
Shabih "Shabby" Rizvi Sep 10, 2018 ▶ 23:58
Insight
Regional startup valuation disparities are set by local investor norms
“Yeah, I think it does vary by region, and I think a lot of that is a byproduct of the micro or the ecosystem on the capital side within those regions. So investors within a region really, I think, are setting the price for what may be the norm there, and so we…”
Shabih "Shabby" Rizvi Sep 10, 2018 ▶ 27:14
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