Nov 27, 2017 · 25m · 20vc
20VC: Kleiner Perkins' Bing Gordon on Lessons From Serving On Amazon & Zynga's Board, Why The Best Investors Are Good Listeners and Sceptical Optimists & The Most Important Value Add A VC Can Provide
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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 Bing Gordon, Partner and Chief Product Officer at Kleiner Perkins, to explore high-impact board governance, venture capital investment strategies, and internal partnership dynamics. Drawing from his executive tenure at Electronic Arts and board roles at Amazon and Zynga, Gordon delivers actionable insights on founder mentorship, valuation, and board leadership.
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 34.4% of the talking time here. How this is scored →
Harry as informed peer 2.0 Guest teaching 3.3 Guest disagreement 1.0 Harry pushing back 1.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 15:14 Contrarian take on valuation sensitivity
Bing rejects Peter Fenton's premise that VCs should ignore valuation, demonstrating mathematically why overpaying reduces total fund opportunities.
Hardest push from Harry ▶ 14:55 Harry challenging valuation logic with Fenton quoteHarry brings a strong counter-opinion from Peter Fenton to test Bing's investment discipline on price sensitivity.
Biggest teaching moment ▶ 5:30 Expected value vs loss avoidance lessonBing educates Harry on how top investors evaluate startup performance through expected value rather than loss avoidance, using Mark Pincus as an example.
Harry holds his own ▶ 14:55 Harry framing valuation debate with industry peer quoteHarry demonstrates industry knowledge by bringing Peter Fenton's exact formulation on valuation traps into the discussion.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Episode Sponsors and Podcast Pre-Roll | 1 | 1 | 0 | 0 | The segment consists primarily of host sponsor reads and an intro. Bing briefly summarizes his 35-year relationship with Kleiner Perkins in a collaborative tone. | |
| Lessons from EA and Managing Venture Cash | 2 | 4 | 1 | 1 | Harry prompts Bing with an insider tip from Eric Feng regarding EA's early days. Bing shares lessons on cash management from Don Valentine and reframes time allocation using expected value rather than loss avoidance. | |
| The Role of a Skeptical Optimist on Board | 2 | 4 | 1 | 1 | Harry brings up the cheerleader versus realist dichotomy of board roles. Bing educates Harry using Amazon's skeptical optimist principle and parenting analogies for board management. | |
| Memorable Board Meetings and Key Pivots | 2 | 3 | 1 | 0 | Harry prompts Bing to share stories of high-impact board decisions. Bing details key moments at Amazon and NG MoCo, along with praising board peers like Mike Maples and USV. | |
| Valuation Sensitivity and Investment Strategy | 4 | 5 | 2 | 3 | Harry cites Peter Fenton's view that price sensitivity is a mental trap. Bing pushes back on the simplification, explaining how overpaying by double cuts fund at-bats in half. | |
| VC Partnership Dynamics and Decision Making | 2 | 3 | 2 | 2 | Harry asks about Kleiner Perkins partnership dynamics before transitioning into quickfire questions. Bing playfully questions Harry's prompt on Taylor Swift before sharing insights on mentor communication. | |
| Improving Venture Capital and Recent Investments | 1 | 3 | 0 | 0 | Bing explains what he would alter about VC and outlines his rationale for recent investments in Network and Zume Pizza. |
Statements from this episode (20)
Gordon: VCs cannot help failing CEOs, only help successful ones scale
“You can't much help them when they fail, but how do you help them scale when they succeed?”
Gordon: Investor board members must be the primary guardians of cash
“The investor board members just half It has to be the most attentive to cash because creative people and strategists don't always think about cash.”
Gordon: Pure investors focus on riding winners over fixing losers
“Most people who are pure investors tend to ride winners rather than trying to fix losers.”
Gordon: Great investors optimize for expected value, not loss avoidance
“And Mark, I think great investors think about expected value, not loss avoidance.”
Gordon: Creativity requires confidence built on optimism and earned success
“Psychologists can prove that creativity is enhanced with confidence. And confidence is built with optimism and with earned success.”
Gordon: Board members must ask hard questions without being hostile
“So I'd say in general, it's ask hard questions, but don't be an asshole.”
Gordon: The hardest operator-to-board-member transition is relinquishing control
“Being a board member for somebody who's been an operator, the hardest thing to do is to realize that you're not in charge anymore.”
Gordon: Optimal three-hour board meetings yield five actionable management ideas
“Board meetings are rated most highly when people are energized and when the management team takes away a couple of good, useful ideas. So I think in a three hour board meeting, five ideas that the manager team writes down and tries to figure out what to deal w…”
Gordon: Amazon AWS, Kindle, and Prime were shaped in key board meetings
“I remember the board meeting on Amazon where we first talked About what become Amazon Web Services, AWS. I remember the first time, I remember a series of meetings that led to the presentation of Kindle. I remember a series of meetings that led to the presenta…”
Gordon: Mike Maples provides game-changing insights in every board meeting
“So I love Mike Maples from Floodgate. He's been, I've been on a couple boards with him. What he does is so well, he has high empathy for CEOs. It seems in every board meeting, he says at least one thing that's game changing.”
Gordon: Most boardroom attendees never say anything useful
“You know, my experience in boards, most people who sit in a boardroom don't say a single useful thing, you know, so if there's only five useful things, if the goal, the high watermark is five useful things in three hours, and when there's five board members, n…”
Gordon: Fred Wilson was crucial early at Zynga despite dialing in
“Fred Wilson is kind of the crown prince of New York venture capital and a great blogger. He was extremely helpful in the early days of Zynga, even though he was mostly dialed in. He's just such a crisp, sharp thinker.”
Gordon: USV led edtech discourse years before making edtech investments
“And then Albert Wenger, he created the meme of hacking education, which I'm a fanboy of. And that was probably in oh nine or oh 10. He convened leading thinkers. And interestingly enough, they didn't invest in any learning and Companies for several years after…”
Gordon: Only execute M&A deals if willing to pay double
“My math is never do a merger and acquisition deal if you wouldn't pay double. Because the ones that work, basically a year later, they're twice as valuable as you thought they were. And the ones that don't work, the amount you spend probably doesn't matter.”
Gordon: Overpaying by 2x cuts a VC fund's at-bats in half
“The negative about that is most of the things that you think you're big game hunting for don't work out, and if you can do 30 investments in a fund and you overpay by double, and there's x percent are gonna be big winners, now you've cut your at-bats in half.”
Gordon: No successful startup investor completely ignores valuation
“I don't know any successful investor in companies who invest that way.”
Gordon: Controversial startup deals are better VC investments than obvious ones
“The other thing that we've discovered is we go around the table and it's controversial. That's often a good thing. And at that point, we depend on one person being a fervent champion on behalf of the company. But if it's really obvious to us, it's probably obv…”
Gordon: Kleiner Perkins requires a single passionate partner to champion every deal
“And, you know, but for us, there's got to be one person who pounds the table.”
Gordon: Analytical strategy documents disable the creative process
“The way to hand off strategies to creative people is Was not to write an analytical doc. He said his secret was to write a short story. So I've taken that forever that I try to get creative people engaged in primary research, basically see customers that if I …”