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

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 — Brought to you by Coda—Meet the evolution of docs: https://coda.io/lenny | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc | HelpBar by Chameleon—the free in-app universal search solution built for SaaS: https://helpbar.ai/lenny/?utm_source=lennys-podcast&utm_medium=sponsorship&utm_campaign=helpbar-launch-lennys-podcast Find the transcript at: https://www.lennysnewsletter.com/p/billion-dollar-failures-and-billion Where to find Tom Conrad: • X: https://twitter.com/tconrad • LinkedIn: https://www.linkedin.com/in/tomconrad/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ 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 Referenced: • Ron Lichty on LinkedIn: https://www.linkedin.com/in/ronlichty/ • 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 • 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 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Tom ConradguestLenny Rachitskyhost
Nov 25, 20231h 40mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

From Pets.com to Quibi: Tom Conrad’s Hard-Won Product Lessons

  1. Tom Conrad, veteran product and engineering leader (Apple, Pandora, Snap, Quibi, Pets.com), reflects on decades of successes and high-profile failures and how they shaped his approach to product, careers, and company-building.
  2. He argues that careers are made as much by failures as by wins, and emphasizes understanding the ‘math formula’ of a business, not just building great products, as a core responsibility for modern product leaders.
  3. Conrad contrasts different company cultures (Apple, Pandora, Snap, Quibi, Zero) to draw lessons on risk-taking, founder dynamics, leadership style, and the value of joining the right team over being a founder at all costs.
  4. Now CEO of Zero, a consumer health app, he shares how focusing on unit economics, metabolic health outcomes, and balanced work culture informs his current leadership and his views on burnout and sustainable careers.

IDEAS WORTH REMEMBERING

5 ideas

Don’t optimize only for product; understand the business ‘math formula’.

Conrad says companies are equations that turn investment into returns. Product leaders must grasp LTV, CAC, unit economics, and the cost structure of their business, or they risk building great features on top of a fundamentally broken model, as he believes happened at Quibi.

Failures can become powerful career assets, not just setbacks.

Experiences at Pets.com and Quibi, while publicly labeled disasters, gave Conrad credibility, opened doors (e.g., to Pandora), and sharpened his judgment on capital, timing, and competitive dynamics. Working at a famous failure can teach timeless lessons and even help you get your next role.

Trust your gut about people and culture when choosing jobs.

He argues most people can sense cultural mismatches during interviews but talk themselves out of it. Long-term satisfaction correlates far more with loving the people and day-to-day collaboration than with external success metrics.

Unit economics and capital discipline beat growth-at-all-costs, especially in consumer subscription.

At Zero, Conrad and the founder chose to grow by improving LTV and retention on organic traffic rather than buying growth, which he contrasts with pandemic-era health apps that burned capital on paid acquisition and later suffered when the market turned.

Not everyone should be a founder; joining the right team can be better.

Conrad believes many smart, semi-visionary people would create more impact—and have better careers—by bringing their skills to teams with sound business fundamentals instead of raising a seed round for a weak idea just to be ‘a founder’.

WORDS WORTH SAVING

5 quotes

There’s this belief that everybody needs to be a founder. I think our industry would be much better off if there were fewer founders.

Tom Conrad

Companies are also kind of like a math problem that describes how you take investment and pour it into the equation, and out the other side comes returns.

Tom Conrad

If the equation is fundamentally broken, no amount of iteration and execution can get you out of the failed outputs of the broken equation.

Tom Conrad

The details are not the details, they make the design.

Tom Conrad, quoting Charles Eames

Whatever the thing is that gets you out of bed every morning, you can achieve that in collaboration with others. You don’t have to be the person that raises the seed round.

Tom Conrad

How to choose where to work: product vs. people vs. business model ‘math’Lessons from major failures: Pets.com and Quibi’s structural and timing issuesLessons from successes: Apple, You Don’t Know Jack, Pandora, and SnapThe importance of understanding a company’s underlying business equation (LTV, CAC, unit economics)Founder vs. operator roles and why not everyone should start a companyLeadership style, risk-taking, and how CEOs should (and shouldn’t) drive productHealth, burnout, and Conrad’s transition to leading Zero Longevity Science

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