Two-Sided - The Marketplace Podcast

Hosted by Sjoerd Handgraaf / Sharetribe

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Oct 2025

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About the show

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 about starting, building, growing and scaling, and every stage in between. In each episode, we will do our best to uncover insights and wisdom you won’t find anywhere else. If you are into online marketplace businesses, you will be into this podcast.

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39 recent

October 22, 202551 min

[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: Constantine explains why the change occurred now and how it was introduced step-by-step to the community.Finding out who your power-users are and what they want: There were several assumptions, both internally and externally, about what Dribbble was, who it served, and who its power users were. But when Constantine had several conversations with uers, and combined the insights from there with the data, it became clear that agencies were the true power users, which helped shape the direction of the changes.The aftermath and the metrics: Despite the initial uproar online, the team soon realized that the loudest comments didn't come from the power users. In fact, within three months, the team saw the GMV triple.All in all, a very thoughtful conversation, that offers several practical lessons on turning attention into reliable revenue, without breaking your community. A must-listen for anyone building a service marketplace!

May 14, 202544 min

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 worked and the mistakes that taught valuable lessons.In this first episode, you can hear the story of Marcel Fairbairn and Gearsource.GearSource is a marketplace that helps rental companies sell professional audio and event production equipment they no longer need. Marcel Fairbairn built the company in 2002, which makes GearSource one of the oldest online marketplaces still in operation, alongside giants like eBay and Amazon.What you'll learn:How a self-funded founder built one of the oldest surviving marketplaces on the internetHow Marcel identified an “invisible inventory problem” that became an idea for a marketplace businessThe critical "aha moment" when Marcel realized his 16-year-old business was actually a marketplace, and how that changed everything in Marcel's approachWhy lowering commission rates accelerated growth and scalabilityThe painful lessons from three platform migrations before finding stability with SharetribeHow to transition from a high-touch service model to an automated marketplaceMarcel's unconventional strategy: "Be aggressive on growing revenue, conservative on growing expenses

April 3, 2025Episode 929 min

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!

March 12, 2025Episode 827 min

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 marketplace businesses.Here are three highlights from the conversation:The Key to Defensibility: Pete explains why network effects are the best form of defensibility for marketplace businesses and how they make companies resilient over time.AI's Role in Marketplaces: Pete discusses how AI is both disrupting and enabling marketplaces, and why it’s creating entirely new marketplace models.The Best Advice for Marketplace Founders: Pete shares his top tips for aspiring founders, from identifying the hardest side of the marketplace to seizing opportunities during economic or regulatory change.Tune in to hear Pete’s insights on building long-lasting, resilient marketplace businesses powered by network effects.

March 5, 2025Episode 737 min

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 technology in creating trust and transparency within B2B marketplaces.Why focusing on niche markets can be the key to achieving fast growth in B2B spaces.A shift in monetization strategies: How B2B marketplaces are moving beyond traditional transaction feesListen to hear how DFF Ventures is backing innovative B2B marketplaces and how aspiring founders can capture market share in under-digitized industries.

February 26, 2025Episode 633 min

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 importance of a strong distribution strategy: A strong go-to-market plan can be the deciding factor in whether a marketplace reaches scale.AI-driven agent-led marketplaces: The future of marketplaces may lie in AI and automation to scale operations and improve the user experience.Did this make you curious? Then don’t wait and tune in to this episode!

February 19, 2025Episode 534 min

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 in decision-making: Jeroen discusses the critical importance of “clock speed” in founders—how quickly they make decisions and adapt to change in the early days.Why market focus trumps premature internationalization: Learn why trying to scale too quickly into multiple regions can backfire for many early-stage marketplace founders.Trends driving marketplace innovation: Jeroen shares his excitement about emerging opportunities, especially in industries like health and Gen Z-driven consumer behaviors.Enjoy this episode!

February 12, 2025Episode 431 min

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 marketplace that directly competes with an established player (frontal attack), advising founders to instead focus on a smaller adjacent market to gain traction and gradually expand into the larger market (lateral attack).The importance of starting in a small, adjacent market: Mira explains how focusing on a niche can lead to faster product-market fit and eventual scalability.Why liquidity is the core of any marketplace: She stresses the importance of building liquidity before worrying about advanced tech or scaling.The role of AI in disrupting marketplaces: Mira discusses how AI can optimize marketplace operations and help founders stay ahead of competition.After this episode, you’ll again have a slightly deeper understanding of what makes marketplaces succeed!

February 5, 2025Episode 336 min

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 exist before, like Airbnb did for short-term rentals.Why building traction before raising capital is key: He shares advice on how to validate your marketplace idea and gain traction without relying on funding too early.The impact of AI on the future of marketplaces: Andrew discusses how AI can enhance marketplace experiences, making connections more efficient and improving customer satisfaction.

January 29, 2025Episode 232 min

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 interactions and defensibility.Challenges in Early-Stage Marketplaces: He discusses common mistakes made by aspiring marketplace founders, such as picking overly narrow markets or trying to tackle too many problems at once.Future Trends in Marketplaces: Sameer emphasizes the lasting power of network effects and we explore some opportunities driven by behavioral shifts, especially with Gen Z and AI technology.A terrific episode, packed with valuable tips and sights. If you're building a marketplace or network effects business, you’re going to love this.