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Two-Sided - The Marketplace Podcast

Two-Sided, the podcast about building an online marketplace business. Two-sided of course, because we’ll discuss Demand & Supply, but also the good side and the bad side, the easy stuff and the hard stuff, and how it looks from the outside versus what is really going on on the inside of an online marketplace. In this series, we sit down with marketplace entrepreneurs, investors and other brilliant minds who work with online marketplaces and two-sided platforms every single day. We will talk…

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[Bonus Episode] Dribbble's controversial pivot to a lead-gen marketplace with Constantine Anastasakis (CEO @ Dribbble)

Surprise! It’s a Two-Sided bonus episode! Sjoerd sat down with Constantine Anastasakis, CEO of Dribbble, to discuss their transition from an online design community to a lead-generation marketplace. The shift sparked a loud social-media backlash, but, as you’ll hear in the episode, the comments mostly missed what was actually happening on the platform. We discuss: The pivot timeline and rationale:…

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Introducing a new podcast: Sharetribe Founder Stories - Marcel Fairbairn of GearSource

** This is a one-off cross-promotional episode of our new podcast: Sharetribe Founder Stories.** This new podcast features interviews with founders building successful online marketplaces with Sharetribe. Discover how founders identified opportunities, overcame challenges, and scaled their platforms—from their first transaction to millions in GMV. Each episode dives into both the strategies that…

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S3E09: Season 3 Recap: six key takeaways

In this solo episode, Sjoerd wraps up Season 3 of Two-Sided, summarizing key lessons from eight insightful conversations with leading marketplace investors. He highlights essential themes like leveraging network effects for defensibility, the power of starting small before scaling, succeeding in B2B marketplaces, and how AI is reshaping the future. A concise yet rich recap—don’t miss it!

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S3E08 - Building defensible marketplaces: insights on network effects and AI - Pete Flint (NFX)

In this episode, we dive into the world of marketplaces with Pete Flint, co-founder of NFX, one of the leading venture firms specializing in network effects. Pete brings decades of marketplace experience, from the founding team at Lastminute.com to the creation of Trulia and its merger with Zillow. At NFX, Pete and his team have a unique perspective on how network effects drive defensibility in…

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S3E07 - Disrupting Legacy Industries with B2B Marketplaces - Laurens Groenendijk & Bas Rieter (DFF)

In this episode, we dive into the world of B2B marketplace investments with Laurens Groenendrijk and Bas Rieter from DFF Ventures. With years of experience as founders and investors, Bas and Laurens (as co-founder of JustEat and Treatwell) share valuable insights into building and scaling marketplaces that disrupt traditional industries. Tune in for: The rise of re-commerce and the role of…

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S3E06 - From first revenue to breakout success - Colin Gardiner (Yonder.vc)

In this episode, we’re joined by Colin Gardiner, a seasoned operator and investor in the marketplace space. From his experience scaling Outdoorsy to leading early-stage investments, Colin dives into the critical elements that make marketplaces succeed and thrive. Highlights: Why unique supply is key: Colin explains how aggregating truly unique supply drives the success of a marketplace. The…

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S3E05 - Founders and speed: finding and funding scalable marketplaces - Jeroen Arts (Speedinvest)

In this episode of Two-Sided, we explore how early-stage marketplace investors like Jeroen Arts at Speedinvest evaluate and support marketplace founders. Jeroen brings years of experience in identifying scalable marketplace models, high-potential founders and shares his approach to spotting opportunities and avoiding common mistakes for early stage founders. Highlights include: The power of speed…

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S3E04 - Navigating marketplace growth: Lateral attacks and the power of the niche - Mira Mihaylova (Piton Capital)

In this episode, we are joined by Mira Mihaylova from Piton Capital. Since its inception in 2010, Piton Capital has focused solely on network effects businesses, having invested in over 100 businesses, all with network effects, and the vast majority of them are marketplaces. Some of the things we’ll talk about: Frontal vs lateral attack strategy: Mira highlights the challenges of launching a…

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S3E03 - What turns a good marketplace into a great marketplace? - Andrew Blachman (Marketplace Capital)

In this episode, Andrew Blachman, co-founder of Marketplace Capital, shares his wealth of experience in building and investing in online marketplaces. As an operator turned investor, he reveals valuable insights for aspiring marketplace founders. Highlights: The importance of creating new market opportunities: Andrew explains how successful marketplaces unlock new supply or demand that didn’t…

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S3E02 - Four steps to evaluate a network effects business - Sameer Singh (SpeedInvest / Breadcrumb.vc)

In this episode, we'll talk to Sameer Singh, an angel investor known for his excellent blog on network effects, Breadcrumb.vc, former Atomico Angel, and current venture partner at SpeedInvest. We’ll discuss how Sameer evaluates marketplace businesses: Evaluating Network Effects : Sameer walks through his four-step evaluation process for marketplace investments, focusing on unique multiplayer…

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