Navigating Leadership Transitions

Tom Conrad is the CEO of Zero and on the board of Sonos. He began his career in engineering at Apple, where he helped build key features that remain in iOS today. Tom was previously the VP of Product at Snap and the chief technology officer of Pandora. He also held leadership positions at notable tech flops Pets.com and Quibi, giving him a unique perspective not only on what it takes to build a successful company but also on lessons from failure. In today’s conversation, we discuss:

• Lessons learned from the infamous failures of Pets.com and Quibi

• Lessons learned from the successes of Apple, Pandora, and Snap

• Advice on choosing where to work

• Understanding the math formula of a business

• How to avoid burnout

• Why Tom says not everyone needs to be a founder

• What he’s building now

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Brought to you by Coda—Meet the evolution of docs | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | HelpBar by Chameleon—the free in-app universal search solution built for SaaS

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Find the transcript at: https://www.lennysnewsletter.com/p/billion-dollar-failures-and-billion

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Where to find Tom Conrad:

• X: https://twitter.com/tconrad

• LinkedIn: https://www.linkedin.com/in/tomconrad/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Tom’s background

(04:40) Landing a gig at Apple

(07:41) Pioneering the blinking folder design on iOS

(11:04) Advice on choosing where to work

(12:43) The importance of trusting your gut when it comes to people

(14:05) Lessons from failed ventures

(17:32) Why and how Pets.com shut down 

(18:30) How Tom’s experience at Quibi renewed his passion for building

(28:48) Takeaways from Quibi and why it ultimately failed

(31:42) Failing is okay

(35:04) Tom’s career at Apple

(39:11) Lessons from You Don’t Know Jack

(40:24) Lessons from building Pandora

(48:24) Looking back at Pandora and what could have been done differently

(55:17) How Tom became VP of Product at Snapchat

(1:01:31) Tom’s philosophy on being involved as CEO

(1:05:51) Tom’s current role as CEO of Zero, and what he’s learned along the way

(1:10:37) How Zero builds product

(1:18:33) Advice on work-life balance 

(1:27:22) Contrarian corner: why not everyone needs to be a founder

(1:30:08) Lightning round

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Referenced:

• Ron Lichty on LinkedIn: https://www.linkedin.com/in/ronlichty/

• What happened to Pets.com?: https://fourweekmba.com/pets-com-failure/

• 11 reasons why Quibi crashed and burned in less than a year: https://www.theverge.com/2020/10/22/21528404/quibi-shut-down-cost-subscribers-content-tv-movies-katzenberg-whitman-tiktok-netflix

• Meg Whitman: https://en.wikipedia.org/wiki/Meg_Whitman

• Jeffrey Katzenberg on LinkedIn: https://www.linkedin.com/in/jeffrey-katzenberg-4b3b47123/

• John Sculley on LinkedIn: https://www.linkedin.com/in/johnsculley/

• Flickr: https://www.flickr.com/

• How Pandora Soothed the Savage Beast: https://www.fastcompany.com/3001052/how-pandora-soothed-savage-beast

• Joe Kennedy on LinkedIn: https://www.linkedin.com/in/joe-kennedy-329417/

• Why Did Yahoo Pay $160 Million for Musicmatch?: https://www.wired.com/2007/07/why-did-yahoo-p/

• TikTok Is the New TV: https://www.wired.com/story/tiktok-new-show-tv-takeover/

• Evan Spiegel on X: https://twitter.com/evanspiegel

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• What sets great teams apart | Lane Shackleton (CPO of Coda): https://www.lennyspodcast.com/what-sets-great-teams-apart-lane-shackleton-cpo-of-coda/

• Flashtags: https://lane.substack.com/p/flashtags

• Patrick Spence on LinkedIn: https://www.linkedin.com/in/patrickspence/

• The Philosophy of Ikigai: 3 Examples About Finding Purpose: https://positivepsychology.com/ikigai

• The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life: https://www.amazon.com/Subtle-Art-Not-Giving-Counterintuitive/dp/0062457713

• High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100

• Hyperion: https://www.amazon.com/Hyperion-Cantos-Dan-Simmons/dp/0553283685

• A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285/

• Mrs. Davis on Peacock: https://www.peacocktv.com/stream-tv/mrs-davis

• Watchmen on HBO: https://www.hbo.com/watchmen

• Lost on Hulu: https://www.hulu.com/series/lost-466b3994-b574-44f1-88bc-63707507a6cb

• Eartune replacement tips: https://eartune.com/products/eartune-fidelity-ufa

• Charles Eames’s quote: https://www.brainyquote.com/quotes/charles_eames_169188

• Compuserve: https://www.compuserve.com/

• Steve Wilhite: https://en.wikipedia.org/wiki/Steve_Wilhite

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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