Jan 2, 2019 · 23m · a16z

a16z Podcast | Improv'ing Leadership

Dick Costolo · 17m spoken Peter Levine · 3m spoken Sonal Chokshi · 21s spoken

0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this a16z podcast episode, former Twitter CEO Dick Costolo and General Partner Peter Levine discuss how lessons from improv comedy, personal resilience, machine learning, and candid mentorship shape effective technology leadership and organizational management.

Chapters · click to jump

1 statement ▾

Dick Costolo worked as unpaid technical consultant on HBO's Silicon Valley open →

1 statement ▾

Costolo trained in same Second City improv group as Steve Carell open →

2 statements ▾

Costolo: AI will replace human-only medical diagnosis within ten years open →

Costolo: AI recommendations will outperform human judgment when they disagree open →

2 statements ▾

Costolo: Leaders must correct mistakes quickly rather than try preventing them open →

Costolo: Twitter took seven years to hit $16, one day to $47 open →

1 statement ▾

Costolo: Twitter partnered with Google to bypass Egypt's Arab Spring shutdown open →

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →

The host as informed peer 1.7 Guest teaching 3.0 Guest disagreement 0.4 The host pushing back 0.0

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

Sharpest disagreement ▶ 10:53 Playful correction on CEO quality ratio

Dick quickly interjects to reframe Peter's statement about CEO quality, playfully nudging back on the categorization of how many CEOs are great versus not great.

Hardest push from the host ▶ 14:13 Pressing on White House call details

Peter presses Dick to move past generalities and detail specifically what the White House wanted when contacting Twitter during international events.

Biggest teaching moment ▶ 11:13 Correcting vs preventing mistakes leadership lesson

Dick educates on leadership strategy by citing Ed Catmull, explaining why leading by preventing mistakes paralyzes companies while rapid correction fosters speed.

The host holds their own ▶ 21:02 Host sharing personal executive mentorship wisdom

Rather than passing the audience question immediately to the guest, host Peter Levine steps in to explain his own career trajectory and mentorship philosophy from his time at Veritas.

the scores for every segment, with the reasoning behind each

Topic	The host as informed peer	Guest teaching	Guest disagreement	Why
Improv Comedy Roots and Lessons in Leadership	1	3	1	Peter asks a standard exploratory question about Dick's unique dual background in comedy improv and tech. Dick provides an extended response on how improv listening skills and handling unpredictable live audiences apply directly to tech management.
Doing What You Love and Building Resilience	2	2	0	Peter shares his GSB teaching philosophy regarding following passion over external expectations. Dick strongly agrees and elaborates with his Michigan commencement address core message on resilience and unexpected world impacts.
Future Tech Trends: Machine Learning and AI	2	4	0	Peter prompts Dick for consumer tech trends. Dick explains machine learning applications from Twitter Moments to healthcare terabytes and AlphaGo's counterintuitive winning moves.
Defining Great CEOs and Embracing Organizational Mistakes	2	4	2	Dick lightly interrupts and reframes Peter's setup on CEO quality before laying out his core philosophy on organizational resilience, citing Ed Catmull on correcting versus preventing mistakes.
Geopolitics, World Leaders, and Twitter's Global Impact	1	3	0	Peter asks about navigating global crises as CEO. Dick shares colorful anecdotes about White House calls, Obama meetings, and handling foreign government faxes without prior political background.
Audience Q&A: Storytelling and Visual Analogies	1	3	0	Peter asks about Dick's reputation as a storyteller. Dick explains using Michelangelo's David as a visual metaphor to maintain employee focus amidst external stock market noise.
Audience Q&A: Mentorship and Seeking Direct Truth-Tellers	3	2	0	In response to an audience question about trusted advisors, Peter shares his own experience on mentorship at Veritas before Dick emphasizes seeking blunt truth-tellers regardless of seniority.

Statements from this episode (7)

Assertion Supported

Dick Costolo worked as unpaid technical consultant on HBO's Silicon Valley

“I contacted the HBO folks who were doing the TV show Silicon Valley and said, hey, I want to come work on Silicon Valley, and the CEO of HBO, Richard Pepler, said, well, we need a, like, technical consultant, but, like, we can't, like, pay you to do it. And I …”

Dick Costolo Jan 2, 2019 ▶ 0:52

Assertion Partly supported

Costolo trained in same Second City improv group as Steve Carell

“I remember I got there my first day, and you're doing the Second City Training Center, and Steve Carell and I and Rachel Dratch were all in the same group, so he and I and Rachel know each other from, like, God, 30 years ago now.”

Dick Costolo Jan 2, 2019 ▶ 2:50

Prediction Not checkable as stated

Costolo: AI will replace human-only medical diagnosis within ten years

“Healthcare, we're going to look back 10 years from now and go, oh my god, we let humans who had only seen four cases of this decide what to do next instead of running it through, you know, here are the symptoms and evaluating against terabytes of historical da…”

Dick Costolo Jan 2, 2019 ▶ 9:17

Prediction Not checkable as stated

Costolo: AI recommendations will outperform human judgment when they disagree

“There are going to be lots of cases of, in specific domains of, it did this thing a human would never do, and there will be lots of machine learning examples of, well, the machine thinks we should do X, and the people think we should do Y, but the machines wil…”

Dick Costolo Jan 2, 2019 ▶ 10:10

Insight

Costolo: Leaders must correct mistakes quickly rather than try preventing them

“It's not your job as a leader to prevent mistakes from happening. It's your job as leader to correct mistakes as quickly as you can when they happen. If you try to lead by preventing mistakes from happening, nobody's going to friggin' take any chances, and the…”

Dick Costolo Jan 2, 2019 ▶ 11:28

Assertion Partly supported

Costolo: Twitter took seven years to hit $16, one day to $47

“So we're doing our IPO for Twitter in November, 2013, and it took us like seven years to get to 16 dollars a share. And then it took us Two weeks to get to 26 dollars a share, and then a day to get to 47 dollars a share.”

Dick Costolo Jan 2, 2019 ▶ 12:17

Assertion Partly supported

Costolo: Twitter partnered with Google to bypass Egypt's Arab Spring shutdown

“Egypt, you know, during the Arab Spring, we sort of started in Tunisia with people organizing protests on Twitter, and they were able to organize protests on Twitter because they were writing under pseudonyms and not, you know, their actual names, so people we…”

Dick Costolo Jan 2, 2019 ▶ 13:28

a16z Podcast | Improv'ing Leadership

How this conversation actually went

Statements from this episode (7)

Turn any episode into a week of clips.