During this year’s NYC Tech Week, Ugly Talk: Scaling Marketplace Startups drew an overwhelming response, with 370 people registering for the packed-house event at the Bank of Ireland Hub. Founders, investors, and marketplace operators came together for a no-fluff conversation about what it really takes to build and scale two-sided platforms.
Moderated by Doug Rogers of Trustap, the panel featured raw, unfiltered insights from Rebecca Kelly (Venue Scanner), Ari Williams (SkipReturns), and Nancy Rhodes (Alternew). From the cold start problem to scaling strategies, the discussion pulled back the curtain on the real challenges (and real tactics) behind successful marketplace growth.
Each founder shared unique experiences navigating the complexities of two-sided platforms, from initial traction to scaling strategies. The overarching message was clear: there’s no single magic bullet, but rather a series of hard-won lessons and strategic pivots.
Below are four key takeaways that emerged from their “no sugar-coating allowed” stories, mistakes, and breakthroughs – insights to keep in mind as you build and scale your own marketplace!
1. That First Deal? Just Make it Happen.
The panel unanimously emphasized that the primary goal is to prove the concept, even if it means relying on manual processes, spreadsheets, and personal intervention to connect your first buyers and sellers. Get your hands dirty.
Why this is important: Early traction, however scrappy, validates your core idea and provides invaluable learning. Focusing too much on perfecting the process before you’ve even had a transaction can lead to analysis paralysis. The aim is to start transacting; refinement and automation can follow.
2. “Organic” is Nice, but “Momentum” is Better. Don’t Wait.
The consensus was that you often need to aggressively seed one side of your marketplace. Ari Williams for instance, spoke about leveraging “demand centers” to tap into existing pools of demand and quickly distribute products, thereby kickstarting activity.
Why this is important: Waiting for perfect organic balance can mean stalling before you even get off the ground. Proactively generating initial liquidity, even if it feels artificial at first, creates momentum that can then attract more organic users to a platform that already shows signs of life.
3. Prove your Model, then Expand.
Start by focusing on and dominating a specific niche, vertical or geographic area. Prove your model and get the flywheel spinning in a controlled environment. Only then should you consider expanding into new territories or broader offerings. However, as Rebecca Kelly’s experience expanding VenueScanner into the US likely illustrates, each new market is its own unique challenge.
Why this is important: What works in one market or segment might require significant adaptation for another due to local nuances, cultural differences, and varying user behaviors. Assuming a simple copy-paste approach for expansion is a common pitfall. Deeply understanding and adapting to each new market is crucial for successful scaling.
4. Leverage Your Users: Turn Pain into Your Recruitment Engine.
Leverage the power of your earliest, most enthusiastic users. Nancy Rhodes of Alternew, with her AI-enabled B2B2C marketplace for after-sales care, highlighted how super-serving these users can turn them into powerful advocates and even active recruiters for the other side of your marketplace. For Alternew, individuals with pressing tailoring or repair needs, when well-served, could be incentivized to bring brands and tailors into the network.
Why this is important: Your most engaged users are not just customers; they can be a powerful, cost-effective growth engine. By identifying their core needs and empowering them, you can transform early traction into a vibrant, self-sustaining community where users help build the network for you.
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This “Ugly Talk” was a fantastic opportunity to learn from those who’ve navigated the chaotic journey of marketplace building. If you were there, thanks for contributing to the conversation. If not, we hope these takeaways provide some valuable food for thought, and we look forward to seeing you at a future event!
Special thanks to Anson Wu for helping put this all together. Visit the Ugly Talk website for info on future events designed to bring founders together for real talk and actionable strategies!
