Navigating Entrepreneurial Journeys and Product Differentiation

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Ayo Omojola is Chief Product Officer at Carbon Health, one of the fastest-growing and most innovative health tech companies in the world. Previously, he was a PM leader at Cash App, where he co-created the Cash Card and scaled it to a nine-figure revenue line for Square. He’s also an angel investor in companies like Mercury, Modern Treasury, Faire, and many others. In this episode, we discuss:

• How Cash App broke through the noise and became a consumer app success story

• Why small teams are better than big ones

• Hard-won lessons on team building and hiring

• Why it’s “criminal” not to connect people in your network to things that they need

• Why you sometimes shouldn’t listen to experts

• The importance of first-principles thinking

• Advice for health tech founders

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Find the full transcript at: https://www.lennyspodcast.com/frameworks-for-product-differentiation-team-building-and-thinking-from-first-principles-ayo-omojola-carbon-health-cash-app/#transcript

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Where to find Ayo Omojola:

• Twitter: https://twitter.com/ay_o

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

• Blog: https://kunle.app/

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Where to find Lenny:

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

• Twitter: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Ayo’s background

(04:13) The story of how Ayo used Quora for discoverability 

(06:44) The scale of Cash App 

(07:37) What Cash App did well

(10:12) Lessons from building consumer apps 

(13:08) Why it’s so important to be different

(14:08) What Ayo learned from how Square/Block operates

(16:36) How to succeed at building a startup within a startup

(19:06) How Ayo transitioned from fintech to health tech

(22:51) Why Ayo loves hiring founders 

(28:32) Team-building strategies

(32:12) The importance of going deep and challenging assumptions

(36:58) Why you should always ask questions

(38:45) Lessons in leadership

(41:43) Advice for founders in the health-care space

(44:48) What Carbon Health is

(46:58) Lightning round

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Referenced:

• Ayo on Quora: https://www.quora.com/profile/Ayo-Omojola

• Carbon Health: https://carbonhealth.com/

• Cash App: https://cash.app/

• Lob: https://www.lob.com/

• Mailform: https://www.mailform.io/

• Venmo: https://venmo.com/

• PayPal: https://www.paypal.com/us/home

• Apple Cash: https://www.apple.com/apple-cash/

• Square: https://squareup.com/us/en/home/

• Block: https://block.xyz/

• Pinwheel: https://www.pinwheelapi.com/

• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032

• Children of Time: https://www.amazon.com/Children-of-Time

• Children of Memory: https://www.amazon.com/Children-Memory-Adrian-Tchaikovsky/

• Children of Ruin: https://www.amazon.com/Children-Ruin-Time-Adrian-Tchaikovsky/

• Stormlight Archive: https://www.amazon.com/Stormlight-Archive-Boxed-Set-Books/

• Fire in the Deep: https://www.amazon.com/Fire-Deep-Robert-J-Miller/

• War of the Worlds on Amazon Prime: https://www.amazon.com/gp/video/detail/amzn1.dv.gti.49a287c2-44ed-4ffc-afa0-fab86dd0d31d

• Succession on HBO Max: https://play.hbomax.com/player/urn:hbo:episode:GWukCJAu0e4uHwwEAAAB5

• No Context Succession on Twitter: https://twitter.com/nocontextroyco

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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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