Lenny's Podcast: Product | Career | Growth

Billion dollar failures, and billion dollar success | Tom Conrad (Quibi, Pandora, Pets.com, Snap, Zero)

November 26, 2023

AI Summary

5 min read

Tom Conrad shares lessons from engineering at Apple, leading product and engineering at Pandora and Snap, high-profile failures at Pets.com and Quibi, and now CEO at fasting app Zero. He emphasizes evaluating opportunities by product fit and team dynamics, while stressing that execution alone cannot fix a flawed business model.

Job Selection and Team Fit

Conrad advises prioritizing products you love and teams that challenge you productively, over external metrics like scale or acclaim. Trust instincts from initial interactions, as mismatches in values or styles become evident quickly. He credits career satisfaction to roles with amazing collaborators, regardless of outcomes—successes built skills, failures opened doors via visibility.

Failures and the Perils of Bad Math

At Pets.com, overfunding sparked an irrational ad arms race among competitors, while dial-up internet made shipping heavy goods unviable; Chewy later proved the model workable with better timing. Quibi raised $2B for bespoke mobile TV but failed on content scale—$2B built 70 shows, far short of retention needs—and COVID halted daily studio production. Key lesson: companies are math equations turning investment into returns; test foundational assumptions (e.g., top-10 app launch via Hollywood marketing) before iterating on product details, as high costs leave no room for normal startup grinding.

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What you'll learn

1 *(04:44) **Early Career at Apple: Inventing Spring-Loaded Folders***
2 *(11:05) **Job Selection: Passion for Product + People Fit***
3 *(14:37) **Pets.com Failure: Overfunding and Timing Traps***
4 *(18:29) **Quibi Postmortem: Broken Business Math***
5 *(35:56) **You Don't Know Jack: Swim Lanes and Depth***
6 *(40:24) **Pandora Growth: Authentic Engagement to 80M Users***
7 *(55:21) **Snap Experience: Executing Founder Vision and Big Bets***

+ Full timestamped outline available in the app

Show Notes

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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