Two-Sided - The Marketplace Podcast

Sjoerd Handgraaf / Sharetribe
  • 4.9 (18)
  • ENTREPRENEURSHIP
  • UPDATED SEMIMONTHLY

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.

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

    10/22/2025 · BONUS

    [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!

    51 min
  2. Introducing a new podcast: Sharetribe Founder Stories - Marcel Fairbairn of GearSource

    SEASON 3 TRAILER

    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

    44 min
  3. S3E09: Season 3 Recap: six key takeaways

    04/03/2025

    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!

    29 min

  4. 03/12/2025

    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.

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

    03/05/2025

    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.

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

    02/26/2025

    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!

    34 min
  7. S3E05 - Founders and speed: finding and funding scalable marketplaces - Jeroen Arts (Speedinvest)

    02/19/2025

    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!

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

    02/12/2025

    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!

    32 min
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4.9
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About

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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