Two-Sided - The Marketplace Podcast

**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

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!

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.

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.

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!

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!

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!

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.

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.

After a brief hiatus, Two-sided—the marketplace podcast is back! I'm super excited to kick off season three of the podcast with a chat with Jose Marin of FJ Labs. FJ Labs is considered the world's most prolific angel investor: they have over 1,100 startups in their portfolio, including heavy hitters like Airbnb, Alibaba, and AngelList (and that's just the ones beginning with the letter A). Jose has also been a marketplace founder himself. His marketplace DeRemate (eBay model for Latin America) was acquired by Mercado Libre, which today is a NASDAQ-listed company. In this episode, Jose and I discuss:How FJ Labs has built its unique investment approach using their vast vertical expertise.The emerging trends in marketplaces FJ Labs are seeing in their portfolio, such as B2B digitalization and cross-border commerce.Some important things that early-stage marketplace founders should look out for.I couldn't have asked for a better opener, so dive right in!

Season three of Two-Sided is here, and we're switching focus. After exploring the experiences of entrepreneurs and founders in previous seasons, we now dive into the minds of the investors shaping the future of online marketplaces. I chat with top marketplace VCs like Jose Marin from FJ Labs, Pete Flint from NFX, and Andrew Blachman from Marketplace Capital to uncover what they look for in startups, the challenges they see, and the trends to watch. Whether you're building or funding, this season is full of insights you won't want to miss.

In this special, one-off mini-episode of Two-sided, Sjoerd asks for your help and reflects back on the past ten years of building marketplace software at Sharetribe.On January 30th, 2024, Sharetribe launched its best marketplace builder today on Product Hunt. We were featured as #2 Product of the Day! Thank you so much for your support! With the new Sharetribe, you can launch a marketplace in a day, without coding. You can also extend it infinitely with code. And scale to any size.Create a Sharetribe account: https://www.sharetribe.comCheck out Sharetribe on Product Hunt: https://www.producthunt.com/posts/sharetribe-2Follow Sharetribe onLinkedIn: SharetribeX (Twitter): @sharetribeInstagram: @sharetribeFacebook: @sharetribe

In this final episode, Sjoerd looks back at season 2. He highlights the top takeaways that any early-stage marketplace entrepreneur can use, and backs them up with outtakes from the interviews.Besides a recap, you can use this episode as a quick guide to discover the episodes you have yet to listen to or rediscover your favorites.We hope you enjoyed this season! If you have any feedback about the podcast, email sjoerd at sjoerd@sharetribe.com.

A community can be a strong foundation for a marketplace. In the early days, it helps with onboarding initial supply and demand and creates trust. Later, it can form a powerful moat that defends the marketplace from competitors.But building a community takes time and work and, most importantly, engaging in it yourself.In this episode, Sjoerd interviews Gene Miguel, CEO and co-founder of Shortboxed, a marketplace for buying and selling comic books.Gene and his co-founder have been lifelong comic book nerds. They both had day jobs in tech, but dealt comic books on the side and spent their days off at comic book conventions. They also started a comic book blog, around which slowly a community started to form.As dealers, they experienced first-hand how poorly and inefficiently the entire comic book secondary market was run. That's when they decided to build Shortboxed.In this season's final Two-Sided interview, Gene shares: How starting a blog helped them build the community How building in public with the community helped them onboard the first supply and demand What a double-bind marketplace is, and why Shortboxed uses that model How they faked many features by running them manually before automating them A compelling story of a marketplace where passion is combined with a solid business case.

Sometimes, the story of the founder can be just as interesting as the story of the marketplace.In the case of Trisha Bantigue, this is certainly the case. Trisha was born in the Philippines, raised by her grandparents, immigrated to the US at age 10, and paid her way through college by competing in pageants. Today, she is the CEO and co-founder of Queenly, a marketplace for formal dresses. Queenly is backed by prestigious investors such as YCombinator and Andreessen Horowitz.Though Two-sided does not focus on founder stories, Trisha's journey is pivotal in the story of Queenly. The idea behind the platform comes from Trisha's own pageant experience. And marketplaces in their early stages need non-scalable tactics; in other words, perseverance. Trisha had that in plenty.In the latest episode of Two-sided, Trisha tells Sjoerd how Queenly got to where it is now:  Launching the app and getting absolutely no traction for months. The difficulty of estimating your own worth as a first-time founder. The challenge of talking to investors in a way that makes them understand your vision and punctures their preconceptions. How to deal with incredible setbacks, and turn them around for the better. Overall, a truly inspiring story for all of the marketplace founders listening

First-time marketplace founders often struggle to balance speed to market and marketplace quality. On the one hand, launching an MVP as fast as possible is often the best strategy.On the other hand, high quality and trustworthiness are essential, especially for peer-to-peer marketplaces.Despite being first-time founders, Gaurav Singhal and Dirk-Jan ter Horst cracked this trade-off from the get-go. When they launched their peer-to-peer car rental platform in Singapore, their sole focus was to get to the market fast. Yet they had a clear vision for Drive lah's customer experience from day one.In the latest episode of Two-Sided, Gaurav shares his lessons on: Transitioning from a corporate job to entrepreneurship: both founders were working at the same corporation, where they conceived the idea over lunch. Testing potential features with manual work before building them – and spending lots of time with customers in the process.  Launching fast with Sharetribe Flex without compromising on their customer experience vision. Working with regulatory limits: before Drive lah, it was illegal in Singapore for private individuals to rent out their car. Putting trust front and center: having raised their seed round one month before Covid, Drive lah was able to turn a potential disaster into a tailwind. Expanding Drive lah to Australia as Drive mate. And much more. An enlightening episode, with something for everyone building a marketplace.

Marketplaces have conquered some industries earlier and faster than others. Besides home-sharing and ride-haling, one such industry is fashion. The European second-hand clothing giant Vinted was founded in 2008. The US-based Poshmark started in 2011 and is now a listed company.One might think there are no opportunities left for new marketplaces in these pioneer industries. One would be wrong. In this episode of Two-Sided, Sjoerd talks to David Oates, CEO and co-founder of Curtsy. Curtsy is thriving in one of the most crowded spaces for marketplaces: reselling apparel.On the podcast, David shares the most important lessons they learned since Curtsy was founded in 2015: Be efficient: Curtsy reached $25M in GMV with a team of six. Start with one niche: Curtsy started as a peer-to-peer dress rental platform for sorority students in Southern universities in the United States. Don't force your business model on your market: it took Curtsy some time to find out people wanted to sell rather than rent out their pre-loved clothing. Have big bets on your roadmap: David finds it important that Curtsy doesn't only focus on incremental improvements. Get the best advice available: Curtsy was part of Y Combinator, which is generally considered one of the best startup accelerators in the world. A very entertaining episode, showing that even crowded spaces have room for new entrants with an innovative approach.

Jason Bergman thinks most marketplace founders underestimate the power of sales.Jason is a big sports fan and has always loved working in sales. Before founding MarketPryce, he ran his own sports agency where he tried acquiring customers by sending Instagram messages to almost three thousand professional athletes.The success rate of the Instagram tactic was pretty terrible. But the experience paid off big time when Jason co-founded MarketPryce, a platform for athletes to find marketing deals. MarketPryce has matched thousands of brands and athletes together. For finding both sides, effective direct sales has been a core strategy.In the latest episode of Two-Sided, Sjoerd talks with Jason about: How most marketplace founders still underestimate the power of direct sales How a change in regulation grew MarketPryce's market one hundred times overnight How MarketPryce modeled its user experience after Tinder. A fun episode, giving a glimpse inside a relatively early-stage marketplace growing very rapidly.

Andrew Gazdecki loves building businesses. He was the weird kid in high school with an eBay store. He built and sold a job board in college. He used the proceeds to start another company, still in college, which he sold before he turned 30. Andrew's latest venture is MicroAcquire, a marketplace for buying and selling online businesses. The platform boasts a community of more than 150,000 entrepreneurs and raised $6.3m in funding last year.In the latest episode of Two-Sided, Andrew talks to Sjoerd about: How his entrepreneurial journey influenced his approach to building MicroAcquire Making non-obvious bets The importance of loving what you do And much more. A really inspiring episode, giving a serial entrepreneur's perspective on building a marketplace business. 

I'm talking to Dirk Fehse, founder and CEO of PaulCamper, Europe's leading marketplace for RV rentals.Many of us have probably daydreamed about spending a few weeks on the road in an RV. Just get in the van, and park it wherever you want, and that's your home for the night. Dirk loved this too, and so much that he founded a company around it. It's a wonderful story, driven by passion, and started out really lean, as you will hear.We talk about:  How PaulCamper got started How Dirk built it piece by piece How they keep quality under control  The quite remarkable way how they use insurance as an anti-disintermediation tool  And how much work Dirk needed to do to get this insurance product into existence.

In business school, Emmanuel Nataf and his friends were bored. They were more interested in startups and tech than studying, and so they decided to start a company: a marketplace around services for self-publishing books. Had any of them ever published a book? No! Did that prevent them from becoming successful? Also, no!We talk a bit about that journey, how they found content & SEO to be their best channel, and how they doubled down on that. We also discuss how Reedsy built a community to support the business and some interesting thoughts about financing your startup.

Knowing is half the battle, said the wise man G.I. Joe at the end of each episode. This rings doubly true for James Younger of TempStars, a marketplace for temporary dental hygienists and assistants. Not only is James working on a problem that he knows really well, but he also made a point of getting to know as much as he could about design, web development, and digital marketing after the first version of Tempstars turned out disastrous. We speak about that, and about how Tempstars got started, how they built a special algorithm to maintain quality, and how they plan to scale the whole of North America.

For this episode, I spoke to James McAulay, CEO & co-founder of Encore, a marketplace for booking musicians. We speak about how James combined his love for music and computer science into Encore. How they got started initially as a “LinkedIn for musicians”, then moved to a “managed reverse marketplace” model to ultimately transform into the online marketplace it is today. Many great stories and lessons to be learned from here.

We kick off the season with a deep-dive by Casey Winters, one of the most knowledgable and experienced two-sided platform people out there. Casey started at Apartments.com, helped Grubhub to IPO-ready, grew Pinterest to an enormous scale, and is now Chief Product Officer at Eventbrite. In between, he has advised a gazillion marketplace startups: Hipcamp, Faire, Airbnb, Uber, GoFundMe... It's almost more difficult to name one that he hasn't advised.

It is coming. Finally. Two-Sided Season 2. I know many of you have been waiting a long time. A big thanks to everyone who has reached out me since the first season, and let me or Sharetribe know how much they liked it. It has been a big motivator for us to continue. It's later than expected, but good things come to those who wait.And boy, are good things coming! I have already recorded some really terrific interviews and a few more in the pipeline, and I found myself learning a whole lot again, about network effects, prototyping, insurance as a service layer, low-frequency marketplaces, and many many more things.  We're going to take it a bit slower this time and we aim to release one episode every two weeks. If you want to be notified automatically, subscribe on Spotify, Apple Podcasts or whatever is the platform of your choice. Also reviews are still very much welcome, hit the 5 stars if you like it, and hopeful that will help us reach more people.That is all for now, you will hear from me and some brilliant marketplace minds soon!

In this episode we look back at season 1. I distill five interesting takeaways that any early-stage marketplace entrepreneur can use, and I have picked out the most relevant outtakes from this season’s interviews.

Bryan Clayton, co-founder and CEO of Greenpal, tells the story behind Greenpal, the marketplace for lawn care, and how he transformed himself from a blue-collar entrepreneur into a tech entrepreneur.

Charles Adler, co-founder of Kickstarter, shares how Kickstarter began and how they grew organically while maintaining the quality and the vibe.

Jacob Wedderburn-Day tells Sjoerd about building Stasher fresh out of university and dealing with the pandemic in a travel industry marketplace.

Ryan Gills shares how Communo got started, why he thinks Fiverr & UpWork are in a race to the bottom, why they built a community that is about giving before receiving and how Communo is building for the future generations.

Kevin Lustig recounts how Scientist.com got started 14 years ago, the ups and downs on the way and how they ended up building an enterprise gateway marketplace serving the biggest enterprises in the pharmaceutical industry.

Sophie Adelman (Whitehat/Hired) shares her experience in building talent marketplaces, and her thoughts on the future of work.

Michael DeGiorgio, founder and CEO of Crexi, joins us for this episode. CREXI is a marketplace for commercial real estate, which, as Michael explains, was an industry ripe for some serious disruption. We talk about how to build productivity tools for one side of your marketplace, how to continuously overdeliver on value, and also about how instead of getting rid of the “middleman”, which is something that you often see when marketplaces enter a space, Crexi actually embraced the middleman. A terrific episode, overflowing with advice for anyone building a marketplace for a B2B vertical.

Before starting Florence, Charles Armitage was a doctor and training to go into emergency medicine. He then decided to radically change his career to start a marketplace for independent nurses and elderly care. Charles tells us all about that, shows us the importance of talking to your customers before building a huge product, (spoiler: their first version failed hard), and how to build relationships and trust in such a delicate market.

We talk to Ruthie Amaru, CEO of Freightos, the world's biggest marketplace for freight. We’ll talk about how to serve fragmented markets, with complex workflows and middleman. We talk about how to get supply onboard before having demand, about building for trust and loads of other great things, especially for B2B marketplaces.

We sat down with Josh Breinlinger to dive into his long history with online marketplaces. Josh was early at oDesk and Rev.com and has invested in several marketplaces while working in Venture Capital at Jackson Square ventures. We talked productivity tools, being anti-hype, and quality in the marketplace.

Lenny Rachitsky (ex-Airbnb) shared his extensive experience and research into kickstarting online marketplace businesses. We'll discuss Airbnb's "Snow White" strategy, his framework for assessing marketplaces, the potential of Neighbor.com, Shopify's Shop App, which flirts with being a marketplace and loads more.

Hi and welcome to Two-Sided, the podcast about building an online marketplace business. My name is Sjoerd, I am your host and also the CMO at Sharetribe, which is the company that brings you this podcast. We decided to call it Two-sided, because of course we’ll discuss Demand & Supply, but also the good sides and the bad sides, the easy and the hard parts, how it looks from the outside versus what is really going on 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 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. I promise you that if you are into marketplaces, you will really enjoy this podcast. So please, subscribe to get updated on the latest episodes, and if you know someone else who might be interested in this topic, don’t hesitate to share this with them!