Predicting the SpaceX, OpenAI, and Anthropic IPOs — With Dick Costolo
Dick Costolo is the ex-CEO of Twitter and managing partner at 01 Advisors. Costolo joins Big Technology Podcast to look ahead to the SpaceX, OpenAI, and Anthropic IPOs, looking at whether the offerings will be successful, who should go first, how the companies differ, and where the capital will come from. Tune in for the second half where we discuss the state of Meta, Costolo's Twitter memories, and Silicon Valley's 'Permanent Underclass.' Tune in for a fun, in-depth discussion of the most important pending business event in decades.
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EP 32: Former Twitter CEO Dick Costolo Talks About His Time at Second City, Running Twitter, and Missing Out on Instagram
In the 32nd episode of Cartoon Avatars former Twitter CEO Dick Costolo discusses his time at Second City with greats like Tina Fey, Amy Poehler, and Steve Carrell, successfully managing and running Twitter as a non-founder, and trying to buy Instagram.
(0:00) Intro
(0:58) Mark Cuban canceled
(4:08) The editing room
(6:07) Logan’s engagement
(9:22) Welcome Dick Costolo
(13:54) Dick’s time at Second City
(28:16) After Second City
(32:44) Why Twitter is a unique challenge
(35:06) Treating all Twitter accounts equally
(40:09) Social Media Regulation
(42:06) Twitter monetization
(44:06) Trying to buy Instagram
(48:37) Social media platform Saturn
(52:01) Expectation setting
(57:10) Leading a company you didn’t found
(59:53) Role vs identity
(1:02:15) Bill Campbell’s mentorship
(1:07:57) Letting people go
(1:12:47) Successful managing
(1:15:42) Marxist vs Darwinian management
(1:19:13) Assume best intentions
(1:24:40) Getting unfollowed by Elon Musk
(1:30:31) Rapid fire
(1:35:14) Outro
Mixed and edited: Justin Hrabovsky
Produced: Andrew Nadeau and Rashad Assir
Executive Producer: Josh Machiz
Music: Griff Lawson
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About the Show
A Saturday morning podcast hosted by Logan Bartlett (Partner and Managing Director at Redpoint Ventures) covering the tech news with his friends and other people with industry expertise.
Executive Producer: Rashad Assir
Producer: Leah Clapper
Mixing and editing: Justin Hrabovsky
Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA
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About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.
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Twitter (with Dick Costolo)
A week before the 2020 US Presidential election, former Twitter CEO Dick Costolo joins us to tell the story of a company that has impacted all of our lives (political and otherwise) like none other. While it's easy to forget now, a very viable alternate history exists where it's Twitter, not Facebook, who owns Instagram, and Vine, not TikTok, that's the global platform for mobile video. We dive into it all on this episode — and of course while we had Dick, we also had to discuss his controversial recent deleted tweet.
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New! We're codifying our own Playbook notes and takeaways from each episode, and posting them on our website. You can read them at: https://www.acquired.fm/episodes/twitter-with-dick-costolo
Links:
Ashish Goel at Stanford: https://web.stanford.edu/~ashishg/twitter.html
Dick and Adam's new firm, 01 Advisors: https://01a.com/
Carve Outs:
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a16z Podcast: Improv'ing Leadership
Leadership is not just about management, but about passion, a bit of humor, and resilience. General partner Peter Levine and Dick Costolo (entrepreneur, former CEO of Twitter, and erstwhile comedian) share their thoughts on the topic in this episode of the a16z Podcast -- based on a conversation recorded as part of the BreakLine program (hosted at Andreessen Horowitz) preparing military veterans transitioning into tech careers.
Among other things, Costolo shares what running Twitter was like pre-IPO and after, as well as what it’s like to suddenly find yourself thrust onto the world stage; the role of improv and imagery in leadership; and the difference between preventing mistakes from happening... and correcting them as quickly as you can when they do happen.
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Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.
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20VC: Dick Costolo on The Balance of Vision and Realism in Startups, The Biggest Challenge in Scaling Twitter & How To Optimise Decision Making Internally
Dick Costolo is the Chief Executive and co-founder of Chorus, a startup that is reimagining the path to personal fitness. Dick is also a Mentor @ Index Ventures, one of the world's leading venture funds, which he joined in 2016. Costolo was most recently Chief Executive of Twitter from 2010 to 2015, where was at the forefront for their hypergrowth onto the main stage of tech. Prior to joining Twitter, Dick co-founded and ran three startups, including FeedBurner, which sold to Google in 2007. The former improv comedian has been a consultant on HBO's "Silicon Valley" and currently sits on the boards of Patreon and IfOnly.
In Today's Episode You Will Learn:
1.) How Dick made his way from Improv Comedian to founding a startup acquired by Google and then becoming CEO of Twitter?
2.) Why does Dick believe that starting a company is like an improv stage? What were Dick's biggest personal learnings from his drama career that he has applied to being a better leader today?
3.) Having given up the comedy dream for tech, how does Dick balance the entrepreneurial unwavering vision with a realism of when things are not working? What is the inflection point?
4.) What was the biggest challenge over the 5 years in scaling Twitter? What strategies did Dick utilise to combat this? How does Dick think about creating a culture of accountability without fear? How does this change the ownership of decisions?
5.) What is Dick's biggest superpower and super weakness? Why must all entrepreneurs have to have a fundamental ability to compartmentalize? In terms of temperament, what were Dick's biggest lessons from watching Youtube CEO, Susan Wojcicki, operate?
Items Mentioned In Today's Show:
Dick's Fave Book: Creativity Inc.
As always you can follow Harry, The Twenty Minute VC and Dick on Twitter here!
Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.
Cooley are the global law firm built around startups and venture capital. Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund's lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.
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Recode Decode: Dick Costolo, CEO, Chorus
Chorus CEO Dick Costolo, the former CEO of Twitter, talks with Recode's Kara Swisher about why he loves comedy and why his peers in the tech community are so infrequently "in on the joke." Before he was a tech entrepreneur, Costolo wanted to be a comedian, taking improv classes at Second City in Chicago in the hopes of one day making it to "Saturday Night Live." Today, he explains, more people than ever have the ability to succeed in comedy because they can make and distribute their comedy online, rather than needing to go to Second City or be a touring stand-up comic. Costolo also talks about what happened when he left Twitter and how he became an advisor to the writers of HBO's "Silicon Valley" during that show's third season.
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a16z Podcast: Teams, Trust, and Object Lessons
Some of the best management books are actually military books, argues Ben Horowitz. There's just a certain mental toughness and focus that that experience gives you, adds Dick Costolo based on his observations.
So how then do you build trust on a team in a company, when it's not (literally) life or death as it is in the military? When giving someone a public "object lesson" -- the equivalent of Sun Tzu's chopping someone's head off -- could mean losing talent ... or being more tyrant than leader? How do you tell the difference?
This conversation -- between Horowitz and Costolo (entrepreneur, former CEO of Twitter, comedian and consultant on the HBO show "Silicon Valley") -- took place before a group of 25 veterans who participated in the Breakline education and hiring program (one week of which was hosted at Andreessen Horowitz) for veterans shifting into careers in the tech industry.
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Follow our host: https://twitter.com/eriktorenberg
Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.
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Recode Decode: Dick Costolo, Former Twitter CEO
Former Twitter CEO Dick Costolo sits down with Kara Swisher to talk about what he's doing next, what he thinks of Twitter's future under Jack Dorsey and why men often fail to "do diversity." Later, Lauren Goode wheels in to Kara's desk to answer readers' questions about "hoverboards."
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