Casey Winters is a legendary advisor on scaling, product and growth. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit. Until recently, Casey was the Chief Product Officer at Eventbrite, and has also led growth and product teams at Pinterest and Grubhub.

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In today’s episode, we discuss:

What every marketplace founder should think about
Why marketplaces are different
Finding product market fit
Key ingredients to scaling a marketplace
Strategies for acquiring demand and supply

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Referenced:

Airbnb: https://airbnb.com/
Bill Gurley: https://www.linkedin.com/in/billgurley/
Blue Apron: https://www.blueapron.com/
Booking.com: https://www.booking.com/
DoorDash: https://www.doordash.com/
eBay: https://ebay.com/
Eventbrite: https://www.eventbrite.com/
Expedia: https://www.expedia.com/
Faire: https://www.faire.com/
Fermat Commerce: https://www.fermatcommerce.com/
Grubhub: https://www.grubhub.com/
Lyft: https://www.lyft.com/
Pinterest: https://www.pinterest.com/
Postmates: https://postmates.com/
Shopify: https://www.shopify.com/
Simon Rothman: https://www.linkedin.com/in/simonrothman/
Square: https://squareup.com/
Tony Xu: https://www.linkedin.com/in/xutony/
Turo: https://turo.com/
Uber: https://www.uber.com/
Zillow: https://www.zillow.com/

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Where to find Casey Winters

LinkedIn: https://www.linkedin.com/in/caseywinters/
Twitter/X: https://twitter.com/onecaseman
Website: https://caseyaccidental.com/

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Where to find Brett Berson:

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson

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Where to find First Round Capital:

Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast

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Timestamps:

(00:00) Introduction

(02:30) Ingredients for a successful marketplace

(05:34) Creating scalable growth loops

(08:42) Emerging marketplaces in 2024

(10:56) 2 ways to acquire supply and demand

(15:39) What’s unique about building a marketplace

(18:27) When to focus on the demand side

(23:10) Who to hire

(26:22) Finding sticky customers

(26:27) What Grubhub should’ve done

(30:19) Uber versus Lyft

(34:23) One thing all marketplace founders should know

(34:45) Finding product market fit

(40:45) Single versus multi-category marketplaces

(43:02) When to expand

(44:22) The best low-frequency marketplace

(46:00) The product is supply, not software

(50:48) No value in car-sharing

(56:11) Improving supply and demand over time

(61:04) The “setup, aha, and habit” framework

(66:27) Avoid these marketplace mistakes

(71:16) 2 people who influenced Casey’s thinking

67: The Data Optimist