leader

also referred to as: leaders

17 statements across 15 episodes · 1 bullish · 4 bearish · 15 people on the record · first statement Jan 9, 2017 by Josh Stein · said 2 times in 1 episodes since 2017 · across every show →

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Everything said about leader, oldest first

Jan 9, 2017 neutral
Assertion Not checkable as stated
DFJ replaces portfolio CEOs primarily for failing to learn from mistakes
“The number one reason where we do occasionally say, Hey, this is not the right leader for the company is when you see someone who's not able to learn from their mistakes, right. And adapt to them.”
Josh Stein Jan 9, 2017 ▶ 9:25 20VC: DFJ's Josh Stein on Why VCs Must Adapt To Their Founders, The Major Transition Points For Aaron Levie @ Box & Why SaaS Startups Are Growing At A Rate Never Seen Before
Jul 14, 2017
Insight
Levchin: Great leaders must drop into trenches and work alongside teams
“Hallmark of a really great leader is someone who can drop down from the 64,000 feet into the trenches with the team, roll up their sleeves, and do some of the work directly right there with the team.”
Max Levchin Jul 14, 2017 ▶ 8:45 20VC: Max Levchin on What Makes A Truly Great CEO, Why Self-Awareness Is The Most Important Trait For Entrepreneurs & Why When There Is Doubt There Is No Doubt
Aug 9, 2019
Insight
Shah: Overconfidence Diminishes a Leader's Impact and True Knowledge
“The more you think, you know, the less you actually are able to have an impact and the less you actually know.”
Hiten Shah Aug 9, 2019 ▶ 11:00 20VC: Hiten Shah on The Right Way To Think About Depression, Control and Burnout, Why Nobody Really Knows What They Are Doing and How One Should Receive Advice As A Result & How To Gain Self-Awareness As A Leader
Jun 1, 2020 negative
Insight
Petersen: Being generically right and specifically wrong is dangerous for leaders
“I think being generically right and specifically wrong is extremely Extremely dangerous as a leader, so you have to actually dive in and really understand the details of what people are doing.”
Ryan Petersen Jun 1, 2020 ▶ 28:49 20VC: It's Time To Talk About Drinking; How To Stop, The Impact It Has, How Life Changes Post-Alcohol and The Biggest Misconceptions on Drinking with Ryan Petersen, Founder @ Flexport, Justin Kan, Founder @ Twitch, Matteo Franceschetti, Founder @ Eight
Mar 30, 2022
Insight
Nottebohm: Executive leaders must absorb pressure rather than pass down anxiety
“And I think part of as you decide that you want to try to help a company grow and be in a leadership position, part of what you're signing up to is absorbing the pressure. That is part of your function. If you just take the pressure and pass down the anxiety, …”
Olivia Nottebohm Mar 30, 2022 ▶ 19:07 20 Sales: Notion's CRO Olivia Nottebohm on How To Build Great Operations at Your Company, How To Use The Trust Equation in Hiring, How To Do Referencing Most Effectively and Whether To Fill Seats or Wait for the Perfect Hire?
Mar 30, 2022
Insight
Nottebohm: Leaders who constantly question their standing operate at half speed
“And a leader who is constantly questioning what their leadership, their own leadership thinks of them is operating at half speed, right?”
Olivia Nottebohm Mar 30, 2022 ▶ 19:26 20 Sales: Notion's CRO Olivia Nottebohm on How To Build Great Operations at Your Company, How To Use The Trust Equation in Hiring, How To Do Referencing Most Effectively and Whether To Fill Seats or Wait for the Perfect Hire?
May 16, 2022 negative
Insight
Fialkow: Poor family relationships signal poor leadership potential
“Somebody who's a loner and somebody that doesn't like to get along with people who has shitty relationships with their family, not as a rule, but it's pretty hard to imagine that they're going to be a great leader.”
David Fialkow May 16, 2022 ▶ 29:33 20VC: The Founding of General Catalyst, What it Takes to Build a Firm That Stands the Test of Time, Why VCs Need to Give Founders Greater Permission to Go For It & Why Venture Capital is Like Tennis with David Fialkow, Co-Founder @ General Catalyst
Jun 15, 2022 negative
Insight
Fishman: Traditional executive interviewing is broken; side-by-side work works best
“I think that the traditional interview process for leaders is broken and the best way to learn about someone is really working side by side with them.”
Adam Fishman Jun 15, 2022 ▶ 26:02 Adam Fishman: Takeaways from Lyft and Patreon; How to Build Viral Loops | 20VC #897 · 20VC with Harry Stebbings
Jul 17, 2023
Insight
Clark: Leaders limit employee potential out of fear of overstretching them
“And, you know, I think people too often put limits on what they think their people are capable of out of fear of overstretching them in some way.”
Dave Clark Jul 17, 2023 ▶ 1:43 Dave Clark: Lessons from Leading 1M Employees w/ Jeff Bezos at Amazon to CEO of Flexport | E1036 · 20VC with Harry Stebbings
Sep 27, 2023
Insight
Lanng: Leaders gain more trust by admitting their weaknesses
“People will actually trust you more. If you show vulnerability. If you say, hey, this is an area I'm bad at as a leader. This is an area I'm good at. Because that helped build a relationship with people.”
Christian Lanng Sep 27, 2023 ▶ 39:15 Christian Lanng: "How Being a Founder Almost Killed Me" | E1065 · 20VC with Harry Stebbings
Sep 27, 2023
Insight
Lanng: Leaders cannot publicly share mental health struggles with their entire company
“As the leader, like, you're a symbol in a way, right? You can't go in a town hall in the whole company and say, listen, guys, I'm actually getting severely depressed at doing the work, or like, you know, I'm suffering from burnout, and I'm not sure I can go th…”
Christian Lanng Sep 27, 2023 ▶ 7:18 Christian Lanng: "How Being a Founder Almost Killed Me" | E1065 · 20VC with Harry Stebbings
Mar 4, 2024
Insight
Tangen: Leaders fail when attempting too many organizational changes too fast
“The people who fail are people who try to do too many things too fast.”
Nicolai Tangen Mar 4, 2024 ▶ 37:44 Nicolai Tangen: Managing the Largest Sovereign Wealth Fund in the World | E1122 · 20VC with Harry Stebbings
Mar 29, 2024
Insight
Hult: Leaders shouldn't just get out of the way of great hires
“I think that there are aspects of a sort of ecosystem or a complicated company where you hire great people. And it's not that you get out of their way, but maybe you support them in a way where they feel empowered to do their job really well.”
Billy Hult Mar 29, 2024 ▶ 8:42 Billy Hult: 27 Years of Compounding Growth Leading to the Market Leader with $1.4BN in Revenue|E1134 · 20VC with Harry Stebbings
May 17, 2024
Insight
Jiaona Zhang: Leaders must model 1.5x the decision speed expected from teams
“I would actually encourage leaders to almost model like 1.5 X where they're hoping out of their team. So if you're like, I want my team to move faster than you as a leadership team need to make faster decisions.”
Jiaona Zhang May 17, 2024 ▶ 37:21 Jiaona Zhang: Why All Product Teams Should Have a Scorecard & How to Use It | E1154 · 20VC with Harry Stebbings
May 29, 2024
Insight
Schroepfer: Great leaders act as conductors to align top talent
“I describe a good leader as sort of like a conductor of an orchestra. It's like I can have the best players in the world, but if they're all playing from a different song sheet, it's gonna sound terrible.”
Mike Schroepfer May 29, 2024 ▶ 0:04 Mike Schroepfer: Former Meta CTO on "Why The Best Leaders are Like Music Conductors" | E1158 · 20VC with Harry Stebbings
Feb 26, 2025 positive
Insight
Leaders Must Constantly Challenge Team Outputs to Maintain High Company Standards
“When I walk into a meeting, I try to remind myself, okay, my mission here is just to add more velocity and to raise the standards. No, nothing that they will present is going to be fine. No, this is the mentality that any leader has to go into, because if you …”
Oscar Pierre Feb 26, 2025 ▶ 40:50 Oscar Pierre, Glovo CEO & Founder: Selling 30% for €100K |The McDonald's Deal That Saved Them |E1263 · 20VC with Harry Stebbings
Jan 9, 2026 negative
Insight
Peet: A Leader's Need For Popularity Prevents Right Decision-Making
“That's the biggest shortcoming I see of a lot of leaders. They cannot stand not to be popular with the people that are beneath them. They avoid conflict, and which means they avoid making the right decision.”
Chad Peets Jan 9, 2026 ▶ 44:40 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets
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