Luck, Grind, and the Founder-to-CEO Transition

In 2010, software engineer Natalie Gordon was pregnant– and fed up with the overwhelming baby aisles in big box stores.  So she quit her computer job to code the registry she wished existed. No pink-and-blue giraffes. No allegiance to a single store. Just a universal list that let friends give the real help that new parents need—from strollers to diaper services to dog-walking.

Natalie coded the first lines of Babylist during her son’s nap time. She managed customer support, pitched bloggers from coffee shops, and learned growth the hard way—first through affiliates, then with a pivotal Pinterest bet, and finally by taking on her own inventory (and all the headaches that come with it). Along the way she wrestled with hiring, firing, fundraising, and the identity shift from founder to CEO. Today, Babylist is one of the most trusted parenting platforms in the U.S., with a retail arm, editorial content, and a program for providing breast pumps. 

This is a masterclass in living a problem–and building a solution. 

You’ll learn:

• How to spot a customer pain point and design an MVP around it
• The power of slow virality
• How to use a small seed round without losing control
• The painful path from affiliate revenue to first-party e-commerce
• Stumbles with hiring – and firing– as a first-time CEO
• How paid growth works on visual platforms like Pinterest
• How “controlling your destiny” justifies a hard shift in business model
• How coaching and feedback helps you evolve from founder to leader

Timestamps:

• 05:32 - Learning to solve hard problems at Amazon -
• 08:28 - Sabbatical in Latin America: Natalie’s first (failed) business and what it taught her
• 17:50 - A meltdown in a superstore → the Babylist “aha” moment
• 19:40 - Designing a universal registry, dog-walking included
• 24:42 - Blitzing the mommy blogs, a  “pregnant hacker” post on Hacker News
• 30:01 - Why $140/month revenue felt like a victory
• 39:18 - Going solo at an Accelerator, and the agony of early hiring and firing
• 49:29 - From “slowly viral” to real scale, and how Pinterest helped
• 58:09 - Affiliate links to in-house inventory → piles of bassinets in the office 
• 1:01:57 - COVID’s unexpected windfall,  the health wedge (breast pumps & beyond)

This episode was produced by Kerry Thompson with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineers were Patrick Murray and Jimmy Keeley.

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