Two-Sided - The Marketplace Podcast – Details, episodes & analysis

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!

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.