Explore every episode of the podcast Two-Sided - The Marketplace Podcast
| Title | Pub. Date | Duration | |
|---|---|---|---|
| S3E06 - From first revenue to breakout success - Colin Gardiner (Yonder.vc) | 26 Feb 2025 | 00:33:33 | |
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:
Did this make you curious? Then don’t wait and tune in to this episode! | |||
| S3E05 - Founders and speed: finding and funding scalable marketplaces - Jeroen Arts (Speedinvest) | 19 Feb 2025 | 00:34:32 | |
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:
Enjoy this episode! | |||
| S2E10 - Growing a marketplace through perseverance - Trisha Bantigue (Queenly) | 08 Nov 2022 | 00:44:58 | |
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:
Overall, a truly inspiring story for all of the marketplace founders listening | |||
| S2E09 - How Drive lah balances speed vs. quality - Gaurav Singhal (Drive lah) | 25 Oct 2022 | 00:45:26 | |
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.
In the latest episode of Two-Sided, Gaurav shares his lessons on:
An enlightening episode, with something for everyone building a marketplace. | |||
| S2E08 - How Curtsy drove $25M annual GMV with a team of 6 - David Oates (Curtsy) | 11 Oct 2022 | 00:46:57 | |
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:
A very entertaining episode, showing that even crowded spaces have room for new entrants with an innovative approach. | |||
| S2E07 - Why you shouldn’t underestimate the power of sales for your marketplace - Jason Bergman (MarketPryce) | 27 Sep 2022 | 00:47:18 | |
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:
A fun episode, giving a glimpse inside a relatively early-stage marketplace growing very rapidly. | |||
| S2E06 - Having fun building your business is a competitive advantage - Andrew Gazdecki (MicroAcquire) | 13 Sep 2022 | 00:40:37 | |
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:
A really inspiring episode, giving a serial entrepreneur’s perspective on building a marketplace business. | |||
| S2E05 - How a passion turned into a marketplace - Dirk Fehse (PaulCamper) | 26 Jul 2022 | 00:33:43 | |
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:
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| S2E04 - How to start a marketplace in an industry you know nothing about - Emmanuel Nataf (Reedsy) | 12 Jul 2022 | 00:35:02 | |
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. | |||
| S2E03 - Focus on a problem that you have experienced yourself - James Younger (TempStars) | 28 Jun 2022 | 00:36:45 | |
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. | |||
| S2E02 - Transforming from a network to a marketplace - James McAulay (Encore) | 14 Jun 2022 | 00:39:16 | |
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. | |||
| S2E01 - Lessons from two decades in two-sided platforms - Casey Winters (Eventbrite) | 31 May 2022 | 00:37:50 | |
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. | |||
| S3E04 - Navigating marketplace growth: Lateral attacks and the power of the niche - Mira Mihaylova (Piton Capital) | 12 Feb 2025 | 00:31:44 | |
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.
After this episode, you’ll again have a slightly deeper understanding of what makes marketplaces succeed! | |||
| Two-Sided Season 2 - Trailer | 24 May 2022 | 00:01:56 | |
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. 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! | |||
| S1E12 - Season 1 Recap: Five takeaways from this season | 12 Aug 2020 | 00:37:07 | |
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.
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| S1E11 - From mowing lawns to tech entrepreneur - Bryan Clayton (Greenpal) | 05 Aug 2020 | 00:40:51 | |
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.
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| S1E10 - Lessons learned from building Kickstarter - Charles Adler (co-founder Kickstarter) | 29 Jul 2020 | 00:53:27 | |
Charles Adler, co-founder of Kickstarter, shares how Kickstarter began and how they grew organically while maintaining the quality and the vibe.
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| S1E9 - Dealing with trust and Covid-19 in a travel industry marketplace - Jacob Wedderburn-Day (Stasher) | 22 Jul 2020 | 00:38:21 | |
Jacob Wedderburn-Day tells Sjoerd about building Stasher fresh out of university and dealing with the pandemic in a travel industry marketplace.
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| S1E8 - Free marketplaces will disappear - Ryan Gill (Communo) | 15 Jul 2020 | 00:37:43 | |
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. | |||
| S1E7 - Building an enterprise gateway marketplace - Kevin Lustig (Scientist.com) | 08 Jul 2020 | 00:48:16 | |
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| S1E6 - Talent marketplaces and the future of work - Sophie Adelman (WhiteHat/ex-Hired) | 01 Jul 2020 | 00:34:15 | |
Sophie Adelman: [00:00:00] But I think people forget that all of these companies started off with humans going out into the streets and making that business work. | |||
| S1E5 - Embrace, don't replace the middleman - Michael DeGiorgio (Crexi) | 24 Jun 2020 | 00:36:56 | |
TS_Michael_Master Michael DeGiorgio: [00:00:00] And I kind of, in the back of my mind, thought, "If nothing else, you know, this'll be a platform that we can transact on ourselves if people didn't want to use it." Speaker 2: [00:00:13] Welcome to Two-Sided, the marketplace podcast, brought to you by Sharetribe. Sjoerd: [00:00:24] Hi. I'm Sjoerd, CMO at Sharetribe, and I am your host. For this episode, I talked to Michael DeGiorgio, founder and CEO of CREXi, a marketplace for commercial real estate. This is an area, uh, [laughs] as you'll hear, which I knew absolutely nothing about, but it turns out to be an actually fascinating industry which was ripe for some serious disruption, as you'll hear. I talk with Mike about how to build productivity tools for one side of the marketplace 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. This is a really intriguing talk, and I think there are some great insights in here for anyone building a marketplace business. Enjoy. Hi, Mike. Welcome to the podcast. Michael DeGiorgio: [00:01:17] Hey, Sjoerd. Really nice to be here. Thank you so much for having me. Sjoerd: [00:01:19] Yeah. I really appreciate it. Hey, before we dive super into the [inaudible 00:01:23] world of CREXi, can you tell the audience a little bit about who you are? Michael DeGiorgio: [00:01:27] Yeah. My name's Mike. I was born on the East Coast of the United States. Started my career about 11 years ago now in commercial real estate. I started it at a company called Auction.com, where we were trying to change the way people bought and sold both residential and commercial real estate. Uh, I was one of the first people on their commercial division, so I was really trying to take commercial real estate transactions online and to online auctions, uh, where I got a pretty good sense of the ecosystem, the software available in our space, and some of the deficiencies in our space. Uh, I spent about four years there, had 10 different roles while I was there, did everything from broker deals to be an auctioneer on auction day, and oversaw multiple different teams, uh, during my run there. And then, left about five years ago to form CREXi. Sjoerd: [00:02:11] All right. So there was already effectively a marketplace, Auction.com? Michael DeGiorgio: [00:02:15] It was really just a different way to transact. It was, uh, taking the traditional process, which is, you know, very manual, and bringing it to an online auction. Auctions were still, at the time, were a known way of transacting commercial real estate and residential real estate, typically for distressed real estate. Uh, what we did was really just bring that auction part online. The rest of our process was, uh, still very much like a broker. Sjoerd: [00:02:39] All right. Yeah. Was it a big operation? Michael DeGiorgio: [00:02:41] So when we started, I was, you know, maybe one of the first five people on the commercial division. My, after being there for about three years, we had raised a large round from Google Capital. We raised $50 million at a 1.2 billion valuation. The company grew to 1,000 plus people [inaudible 00:02:56] during my time there. And then, I left. So got big over time. Sjoerd: [00:03:00] Yeah. And so, you left, and then immediately after, you started CREXi? Or did you leave really to start CREXi? Michael DeGiorgio: [00:03:07] Left to start CREXi. I was pushed by a former mentor of mine, uh, over drinks one night, to kind of, threw a, lobbed a question at me asking what I would do if I could go kind of out on my own. And I responded by telling him, "I think there's a way to bring, really, everything about commercial real estate, leasing, transacting, data, online in an intuitive way that's not out there, and I would go start that company." And he became my first investor, and I left my career behind about a month and a half later to go start CREXi. Sjoerd: [00:03:36] All right. So basically, you are this, well, let's say, hardcore real estate veteran. And during your time at Auction, you were just thinking, "Ah, we could do this so much better." Is that what happened? Michael DeGiorgio: [00:03:48] Yeah. I think especially, you know, at first, I was very bought into the vision. I think over time, as I learned how the transaction works for real estate really well, I probably sold 600 commercial real estate properties during my time there. Sjoerd: [00:04:00] [laughs] Wow. Michael DeGiorgio: [00:04:00] As I kind of started to learn the different ways commercial real estate was sold and really started to get to know some of the software that was available to us in the space, because we still used other software platforms to help our process, I started to see that there was none I really believed in, and there was a much better way of doing it. And a lot of them were really, you know, antiquated, kind of web 1.0 version technology that I thought could be enhanced and taken so much further than it was. So I set out on the journey. Sjoerd: [00:04:27] And could you share a little bit, like, what were the things that you're like, "Ah, this is, you know, we, first thing I'm going to do at CREXi, this is what we're going to do. Like, this is how we are going to be different from Auction.com and whatever other things were out there?" Michael DeGiorgio: [00:04:40] Yeah. I guess in its most simple form, you know, Auction.com was really putting people in a box. They were forcing, if you wanted to use it, you had to transact in an auction. And I started to learn pretty quickly that oftentimes, I would sell the property prior to the auction, more traditionally, or after the auction, because the deal wouldn't sell in the auction, more traditionally after the auction. And there's just so many different ways to transact commercial real estate. And there's also a lot of tedious processes involved in transacting commercial real estate that would take half your day and really get in the way of just you getting a deal done. And so I, I really thought, you know, the two basic things were, most importantly, let's build some tech to solve some of these pain points that, you know, maybe used to take a half a day. I could take it and make it a couple clicks of a mouse. And let's make it more flexible so you didn't kind of get forced to transact in an auction only. I thought, over time, you know, that can be an offering we have. But let's make it really flexible so that you can transact in multiple different ways on the platform. And I kind of, in the back of my mind, thought, "If nothing else, you know, this'll be a platform that we can transact on ourselves, if people didn't want to use it." So that was kind of our backup plan, was let's build something where, if I had to go start transacting real estate again tomorrow, I would be able to transact better than I could without this platform that we were going to build. And the hope was people saw the value in that, the time saving in that, the different, you know, advantages of being able to use a platform like ours, and everybody would start to use it. And we'd get the whole industry there together. And if we didn't, you know, we had, we at least knew we could transact on it and make it big that way. Sjoerd: [00:06:10] Yeah. So... | |||
| S1E4 - Talk to your users before building anything - Charles Armitage (Florence) | 17 Jun 2020 | 00:40:18 | |
Sjoerd Handgraaf: [00:00:15] Welcome to two-sided, the marketplace podcast brought to you by Sharetribe. Sjoerd Handgraaf: [00:00:23] Hi, I'm Sjoerd CMO with Sharetribe and I'm your host. I'm actually very excited today because this is the first time that I can say to at least some of you welcome back because we dropped the first few episodes last week and the response has been absolutely amazing. And if you're one of the people who heard those and came back, thank you so much.And also thank you for the fantastic response we've gotten so far. Now let's dive into the episode. So in this episode, I'm talking to Charles Armatage. Charles was actually a doctor and training to go into emergency medicine, but then decided to radically change his career to start a marketplace for independent nurses and elderly care. Well, Charles will tell us all about that. And it's a very interesting story, but he'll also show us the importance of talking to your customers before actually building your huge product. You know, spoiler alert, their first version failed hard and how to build relationship and have trust in such a delicate Margaret. Again, I've only had fantastic episodes so far, and this one is no exception. So sit tight and listen to Charles story Charles Armitage: [00:01:27] about Florence. Sjoerd Handgraaf: [00:01:36] Hi Charles. Welcome to the show. Charles Armitage: [00:01:38] Thanks very much for having me. Sjoerd Handgraaf: [00:01:39] Hey, I checked out a little bit of your background. I saw that you're trained as a doctor and well, I think we'd like to know a little bit more about you. So can you tell us a little bit about what you did before you ended up at Florence? Charles Armitage: [00:01:51] Sure. So, uh, absolutely. So it was a, a doctor in the UK and a number of different specialties, but it kind of was settling in on emergency medicine and then laterally surgery. So was pursuing a career in trauma surgery, but still relatively, kind of early on in that journey. It takes quite a long time to get to. You know, the end of being a trauma surgeon, but yeah, so worked in a lot of places, worked in London a lot on the South coast and up in Scotland and then some other funny places around the world, like South America and Africa and places like that. Sjoerd Handgraaf: [00:02:21] That was too boring for you or what was the reason why were like, Hey, Charles Armitage: [00:02:25] sure. I'm sorry. Is that something that was a bit boring actually. So I could talk about this forever, but the thing about medicine is that, um, you know, you get moments of absolute, huge adrenaline rushes and amazing thrills. Also punctuated by quite a lot of time, grinding your head against quite a challenging system. And you can spend a lot of your time doing paperwork and filling out. You're not necessarily having a massive impact. And certainly that the impact you're having isn't exactly scalable. You were kind of an equals wide and there's only so much you can do really to make a change. And so Sjoerd Handgraaf: [00:02:54] were you always into tech that you're like, I'm going to start a startup for like, maybe you can tell us a little bit into the origin of Florence. Charles Armitage: [00:03:02] Yeah, for sure. I mean, I've always been kind of interested in tech and I was like new shiny things, but essentially, you know, learn more and more about myself. And my drivers is kind of my goal and the journey, but essentially I just like new things and maybe I've got a slightly short attention span. So always kind of looking for something new on the horizon. And I was working in. London at the time in emergency medicine and was really enjoying their job. But at the same time, it was kind of investigating things on the size. And one of the things I noticed and it's kind of a pervasive problem throughout healthcare in the UK and actually most of the world is, you know, the biggest challenge is staffing. And how do you create a solution to some of the biggest challenges we face as a society, which is, you know, looking after an aging population and providing the staff to do that in like a safe and high quality way. So I was messing around with some ideas in this, any department, trying to kind of build an app for me and my colleagues to swap shifts and, you know, work more effectively between us. And obviously like couldn't build it because I'm not technical. And it started kind of the idea going and didn't really come to much. And then I met my cofounder, Dan, who is from the military, but I guess comes from the other side of the fence as well. He manages a care home group. Well manage the cat and group in London. So it was having challenges, finding staff to look after their residents. And we met, we were introduced by a mutual friend and kind of started bouncing some ideas around. We both had ideas in the kind of space of how can we use technology to bring together this supply and demand in a more intelligent way and, you know, high quality cost effective, all these kinds of great things. And then we just started like, thinking about it and it's right. Single map. And you know, the rest is history. Sjoerd Handgraaf: [00:04:40] Yeah for the people at home. So could you tell us a little bit about what is Florence exactly. Charles Armitage: [00:04:45] Sure. So Florence is the online marketplace for flexible staffing on demand staffing in the cat section UK. So what we do is we have a platform that connects care homes to nurses and carers looking for extra shifts. And I guess, traditionally the problem in the UK cast actor is a massively understaffed industry. So. It was around about 120,000 vacancies in UK care sector. So what ends up happening is a huge proportion of shifts. About 10% of all shifts in calc care in the UK have felt both. Temporary workers, flexible workers. Sjoerd Handgraaf: [00:05:18] Is that elderly care only or health care. Charles Armitage: [00:05:21] Yeah. So when I talk about car I’m talking about elderly care in the community. So in town homes, nursing homes, not necessarily the health care sites, which is more the NHS, and there's a bit of a differentiation of the UK. What ends up happening is about 10% of this workforce is temporary, is flexible and it's managed. Pre Florence was managed by traditional recruitment agencies who were really fragmented offline processes. You know, one man and his phone kind of with relationships with individual workers or homes and bring these two people together. And, you know, whilst. That's a model as well. For very long time, it was hugely expensive for the care sector. So billion spent every year just on the kind of the agency models in the middle. And there's just so much that could be done with technology to improve those engagements. Sjoerd Handgraaf: [00:06:02] Yeah. And so Dan had experienced that problem himself. Charles Armitage: [00:06:05] Yeah. So he was the chairman of this nursing home that couldn't find nurses. And on the other side was a doctor who would occasionally work these flexible shifts in the NHS and, you know, weekends or holidays. I, you know, want to get an extra share for a bit more pocket money. And whilst I knew there was a shift down the road, I'd have to call up my recruitment agency and get sent to Birmingham and, you know, turn up and get thrown the keys and told, you know, that they'd be back in 12 hours. So it was January, a really poor experience and I needed a better way of doing it. Yeah. Sjoerd Handgraaf: [00:06:33] And so you said, Dan is your co founder, is he a more technical pers... | |||
| S3E03 - What turns a good marketplace into a great marketplace? - Andrew Blachman (Marketplace Capital) | 05 Feb 2025 | 00:36:35 | |
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:
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| S1E3 - Building a marketplace for a fragmented market with complex workflows - Ruthie Amaru (Freightos) | 07 Jun 2020 | 00:38:59 | |
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.
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| S1E2 - Optimize for quality and productivity in your marketplace - Josh Breinlinger (Jackson Square Ventures) | 07 Jun 2020 | 00:21:00 | |
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.
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| S1E1 - Build something people want - Lenny Rachitsky (ex-Airbnb) | 07 Jun 2020 | 00:44:12 | |
Sjoerd Handgraaf: [00:00:23] Hello and welcome to two-sided. I am Sjoerd CMO at Sharetribe, and I'm your host. And this episode I talked to Lenny Rachitsky. He first founded his own marketplace company, then sold it to Airbnb, worked there for seven years until last year. Since then he has been writing fantastic content about marketplaces, which you can find at lennysnewsletter.com. I talked to him about his time at Airbnb about his framework for evaluating which marketplace to invest in, why Shopify still has a lot of work to do with their new shop app. Why Neighbor the Airbnb for storage might just work, but most importantly, we talked about how to kickstart and scale a marketplace business. I really enjoyed talking to Lenny and I hope you will as well. Hi Lenny, welcome to the podcast. Lenny Rachitsky: [00:01:17] Thanks for having me. Sjoerd Handgraaf: [00:01:18] Like I already mentioned in the introduction, so you worked a long time at Airbnb. Nowadays, you read a lot about marketplaces. I'm curious what got you first into online marketplaces. I dug a little bit into your history and I saw that Localmind was maybe the first one. Can you tell us a little bit about that? Lenny Rachitsky: [00:01:35] Yeah, you bet. So Localmind was a company that I started in 2010. I was working as an engineer before that for about 10 years, engineering dream manager. And I always had this goal of starting a company and it was randomly in Montreal visiting a friend at a conference, and we were talking in this idea for what Localmind turned into kind of spring out of that. And so I moved to Montreal to start this company and stayed there actually for eight months and then moved to the Bay area. And with the company was all about, was. It was around the time Foursquare was really popular and everyone was going to check it in. And there's all this data around location and where your friends are at and where you're spending time. And so we had this idea, what if, what if we could connect people that are at any place in the world with people that want to know what's happening there because everyone's got this phone in their pocket. There's a way to reach them. Now there's all this data about where people are and if they opt into, but if we could connect people at a place where people want to know what's going on at that place, and that's what Localmind was. You open up the app, you choose a place that you're thinking about going to, and then you ask questions and we route it to somebody there. Right now that's check in on Foursquare, Google or Facebook or someone that knows a lot about the place and that's what it did. Sjoerd Handgraaf: [00:02:43] And then questions like, you know, who's deejaying or like what's on the menu? Or like those kinds of things. Lenny Rachitsky: [00:02:50] Yeah. The most popular was like, how long has the line at this club? Is it busy at this restaurant? Or like, yeah, that kind of thing. And in the end we found it wasn't a big enough problem for people, so it wouldn't last as a standalone business. And that's how we ended up selling therapy and B. But it was fun and it might be possible now. It might be worth trying to have some time. Sjoerd Handgraaf: [00:03:10] Yeah. What's your, something with Localmind, because it is a kind of marketplace, but was there something that you learned there that you still feel like, Oh yeah, that is a huge lesson that I learned there. Lenny Rachitsky: [00:03:18] I rarely look back at local. Mine is kind of building a marketplace, but it definitely was, and we should probably spend more time on this, but I'd say the main takeaway is a marketplace, maybe like 90 I don't know, maybe 99% of the success of a marketplace is the same as the success of any business, which is just, does anybody even want this thing? Is this actually solving a problem for anybody? And so with Localmind, we basically eventually realized this is not a big enough problem. People wanting to go out and really needing to know what was happening at a place. So most of the learning there is just how could we have earlier knowing that this is not a frequent enough problem for enough people and maybe just a course or not. Sjoerd Handgraaf: [00:03:58] Yeah, because now while you were saying this, my question that was straight coming to am I like, okay, is there any other way you could have validated this without actually building a whole product? Lenny Rachitsky: [00:04:07] Yeah, maybe like we could have had text messages or something initially. But you know, it wasn't years of work and we built it pretty quick. Maybe the other lesson that's interesting is one of the more common ways to build a marketplace and to bootstrap a marketplace is to piggyback off of an existing network. Like the way Airbnb allegedly is, Craigslist and Uber, and a lot of other companies use Craigslist. So what we did is we bootstrapped off of Foursquare's data. We basically let you connect your four square account, and then we knew about every check in that you made, and as soon as you checked it on Foursquare, we had you. At that location in our app, and that made it a lot easier to scale. And with the work that I've been doing recently, looking into how the marketplace has worked, that's one of the more common strategies that worked back then and still works. Sjoerd Handgraaf: [00:04:50] And then, so Airbnb bought Localmind Was it like an acquihire? Did you then straight move into Airbnb? Lenny Rachitsky: [00:04:57] It was not technically an acquire. They acquired the whole company. All of us went over except for one person who decided to do some different, and they bought us as a team and they wanted us to. Work on a specific need that they had at that time, which was based on, so at that point, the kind of the strategy of the company was focused around what was called snow white snow white frames, which there's some articles about this. And the way that worked is Brian, the CEO over the holidays, red. Walt Disney's biography, and he learned as he was reading that, that the movie, snow white, was the first animated feature film. And to make that possible, they have to use storyboards in order to kind of map out the story. And when you make a storyboard, you basically map out the key frames of a story to understand where it goes and how it all fits together. And what Brian kind of realized while he was reading it as a trip on Airbnb is just like a story that unfolds. There's a beginning, there's a middle, there's an end. And what he ended up doing is hiring a storyboard artist from Pixar to come work at everybody full time and to map out the story of an Airbnb guest and an Airbnb host. And so if you go to the office at Airbnb on CDs frames on the wall, and it's something that folks look to when they're thinking about what to focus on, how to think about the user. And so this happened right around the time they acquired us. And the reason they wanted us to work at Airbnb is they wanted us to nail the, I'm out and about in a city. What should I do? How do we make that experience amazing? And they wanted to make every one of those key frames amazing. At week. And so they acquired us, focused on that problem, and we ended up building something that ended up not launching later. But that's its own story. Sjoerd Handgraaf: [00:06:33] Yeah. So what's your journey within every MBA? So you started with that then for you moves into growth. Lenny Rachitsky: [00:06:40] Yeah. So first we built that, then we moved into building a community platform for the host community. To help them connect with each othe... | |||
| Two-Sided - The Marketplace Podcast - An Introduction | 03 Jun 2020 | 00:01:27 | |
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!
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| S3E02 - Four steps to evaluate a network effects business - Sameer Singh (SpeedInvest / Breadcrumb.vc) | 29 Jan 2025 | 00:32:26 | |
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:
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. | |||
| S3E01 - Lessons from investing in 1,100+ network businesses with Jose Marin of FJ Labs. | 22 Jan 2025 | 00:38:33 | |
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:
I couldn’t have asked for a better opener, so dive right in! | |||
| Two-Sided Season 3 coming out next week! - Trailer | 16 Jan 2025 | 00:03:58 | |
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. | |||
| Sharetribe launched on Product Hunt! | 30 Jan 2024 | 00:06:16 | |
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.com Follow Sharetribe on
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| S2E12 - Season 2 Recap: six essentials insights from this season | 06 Dec 2022 | 00:28:12 | |
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. | |||
| S2E11 - How a comic book community turned into a marketplace - Gene Miguel (Shortboxed) | 22 Nov 2022 | 00:49:48 | |
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.
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:
A compelling story of a marketplace where passion is combined with a solid business case. | |||
| S3E09: Season 3 Recap: six key takeaways | 03 Apr 2025 | 00:29:09 | |
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! | |||
| S3E08 - Building defensible marketplaces: insights on network effects and AI - Pete Flint (NFX) | 12 Mar 2025 | 00:27:01 | |
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:
Tune in to hear Pete’s insights on building long-lasting, resilient marketplace businesses powered by network effects. | |||
| S3E07 - Disrupting Legacy Industries with B2B Marketplaces - Laurens Groenendijk & Bas Rieter (DFF) | 05 Mar 2025 | 00:37:32 | |
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:
Listen to hear how DFF Ventures is backing innovative B2B marketplaces and how aspiring founders can capture market share in under-digitized industries. | |||
| Introducing a new podcast: Sharetribe Founder Stories - Marcel Fairbairn of GearSource | 14 May 2025 | 00:44:00 | |
**This is a one-off cross-promotional episode of our new podcast: Sharetribe Founder Stories.** 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:
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| [Bonus Episode] Dribbble's controversial pivot to a lead-gen marketplace with Constantine Anastasakis (CEO @ Dribbble) | 22 Oct 2025 | 00:51:23 | |
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.
We discuss:
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