Yesterday Podcast

Yesterday

Interviews on inspiring life stories. yesterdayy.substack.com

  1. Aaron Levie | He Cold Emailed Mark Cuban To Invest in His Startup (Now They’re Worth $5B)

    10/17/2025

    Aaron Levie | He Cold Emailed Mark Cuban To Invest in His Startup (Now They’re Worth $5B)

    Episode #18 of Yesterday:Aaron Levie is the co-founder and CEO of Box (NYSE: BOX), a cloud storage company used by over 100,000 businesses worldwide, including 67% of the Fortune 500. He co-founded Box in 2005 while a student at USC, initially funding it with online poker winnings before securing an investment from Mark Cuban off a cold email. Under Aaron’s leadership, Box grew from a dorm-room startup to a publicly traded company with more than $1 billion in annual revenue and over 2,000 employees. In this episode, Aaron shares the unfiltered journey behind that growth: The early pivot from a consumer product to an enterprise-first model, to navigating the “innovator’s dilemma” He also discusses how the iPhone and the broader mobile revolution reshaped Box’s product strategy and accelerated enterprise adoption. TIMESTAMPS: 00:00 Intro 01:34 Box Origin Story 04:24 Funding the Company with Online Poker 05:46 The Cold Email That Landed Mark Cuban 07:06 Dropping Out of College for the Dream 09:52 Advice From Mark Cuban 11:12 Enterprise vs. Consumer 12:50 Using the “Innovator’s Dilemma” 15:59 The iPhone Launch 17:46 The ChatGPT Moment 21:02 AI Pivot 26:05 SORA Video Generation 29:45 Why Most Companies Are Failing 33:12 Agents Automating Everything 35:50 Jack Dorsey’s Favorite Entrepreneur 38:13 Advice for Young Founders Presented by Rho: Rho is the all-in-one banking platform for startups, used by Perplexity, Product Hunt, and thousands of other companies. You get everything you need to manage your startup’s cash & a team that’s obsessed with helping founders beat industry giants. Learn more at rho.co/yesterday Sponsored by The Cannon Project (TCP): TCP recruits founding GTM and engineering teams for startups like Ramp, Cursor, and Decagon while investing through their flagship venture fund, TCP 1. Apply for roles and learn more at thecannonproject.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com

    46 min
  2. Jonathan Neman | How Sweetgreen Became a Multi-Billion Dollar Salad Chain

    10/15/2025

    Jonathan Neman | How Sweetgreen Became a Multi-Billion Dollar Salad Chain

    Episode #17 of Yesterday:Jonathan Neman is the co-founder and CEO of Sweetgreen, Inc. (NYSE: SG), the mission-driven restaurant brand redefining fast food through fresh, seasonal, and sustainable meals. Born in Los Angeles and a graduate of Georgetown University’s McDonough School of Business (’07), Neman co-founded Sweetgreen with classmates Nicolas Jammet and Nathaniel Ru shortly after graduation, opening the first location in Georgetown, D.C. in 2007. Under his leadership, Sweetgreen has grown from a single salad shop into a nationwide company with hundreds of locations, a leading digital platform, and a public listing on the New York Stock Exchange. Timestamps: 00:00 Intro 01:41 Parents Fled a Revolution for the American Dream 04:00 The One Rule Dad Had 08:33 Selling Ads in High School 14:49 The 25,000-Person Music Festival 17:03 Escaping the “LA Bubble” 21:41 The Australian Cafe That Inspired Sweetgreen 24:23 The Hated Consulting Job 26:45 The Partner Who Told Me to Quit 29:23 The Complaint That Sparked Sweetgreen 36:24 Raising $300k from $5,000 Checks 37:23 The Co-Founder Who Quit 45:15 The Power of Doing One Thing Perfectly 47:50 The #1 Rule for Running a Business 50:52 From Dishwasher to Head Coach 55:25 Building a Restaurant App 58:32 Revolutionizing Takeout 1:11:18 The Reality of a Founder’s Life 1:13:42 Happiest vs. Unhappiest Moments Presented by Rho: Rho is the all-in-one banking platform for startups, used by Perplexity, Product Hunt, and thousands of other companies. You get everything you need to manage your startup’s cash & a team that’s obsessed with helping founders beat industry giants. Learn more at rho.co/yesterday Sponsored by The Cannon Project (TCP): TCP recruits founding GTM and engineering teams for startups like Ramp, Cursor, and Decagon while investing through their flagship venture fund, TCP 1. Apply for roles and learn more at thecannonproject.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com

    1h 16m
  3. Akshay Kothari | $90M Acquisition to Co-Founding Notion ($10B+ Valuation)

    09/16/2025

    Akshay Kothari | $90M Acquisition to Co-Founding Notion ($10B+ Valuation)

    We discuss the life story of Notion’s co-founder, Akshay Kothari. Notion is a productivity tool, valued at $10B+ with over 100M users. Akshay grew up in Western India in Ahmedabad, the largest city in the state of Gujarat. He has two brothers, Nikunj & Pranav, and is the middle child. Their family business centered around finance and loan-giving, common for some Indian families at that time. Early on, Akshay was quite terrible at school… once all-consumed by the desire of being a cricket player. A pursuit that his loving mom supported, with the caveat that he must work & practice accordingly if that was his dream. After realizing cricket wasn’t going to be his calling, Akshay took inspiration from his older brother Pranav and made his way to the USA to study engineering at Purdue. Through a series of unfortunate, yet equally fortunate, circumstances Akshay made his way to Stanford for a graduate degree. On his first day, Lehman Brothers collapsed in the Great Financial Crisis. Later in his Stanford tenure, he founded a news reader app called Pulse. That same year, Steve Jobs announced them as his favorite iPad app on stage at WWDC. Later, Pulse was acquired by LinkedIn for $100M. This prompted Akshay’s move to India to spearhead LinkedIn’s growth there, and also a series of angel checks. The first of which was Notion. For four years, the company made minimal progress. When they finally started seeing PMF, Akshay joined as a co-founder alongside Ivan and Simon. Fast forward to the present day, Akshay has been at Notion for just over 7 years. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com

    36 min

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Interviews on inspiring life stories. yesterdayy.substack.com

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