Marketplace Memo #18 - Agent-Led Marketplaces, SaaS Crash and More
OpenClaw Marketplaces, Marketplaces Outperform SaaS, eBay Acquires Depop, OpenAI Launches Ads, Etsy and Wayfair Now in Google Gemini, Airbnb Q4 GBV Up 16% And Much More!
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👋 Welcome to the 18th edition of the Marketplace Memo. My goal is to share curated news, content, and stories about marketplaces, with a splash of my own color. Please enjoy and share with others!
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Agent Economy Vibes
About a year ago, I wrote:
"The real potential of AI in marketplaces lies not in optimizing processes but in reimagining them entirely. AI is the key to a new model in which the heavy lifting of aggregation, matching, and decision-making is no longer human-driven but agent-led." - Agent-Led Marketplaces
And I think that revolution is starting to happen. But first, let’s talk about internet lobsters. 🦞
Peter Steinberger built Clawdbot as a weekend project in November. It is an open-source software that connects an AI model to your messaging apps so you can text it tasks and it executes them (much more to it, but that is the gist). By late January, it had been renamed twice (Anthropic’s trademark lawyers had gotten involved) and reborn as OpenClaw. Then, Matt Schlicht had his agent build a social network called Moltbook, which launched on January 28th and, within days, had 1.6 million bot accounts and 7.5 million AI-generated posts (now much more). Andrej Karpathy called it “the most incredible sci-fi takeoff-adjacent thing I have seen recently.” All of this in about three months, and then OpenAI “acquired” OpenClaw. Outside of the tech theater, what caught my eye was that people/agents immediately started building marketplaces, kickstarting the agent or agentic economy, as some have called it.
Three distinct models have emerged:
A2A (Agent-to-Agent): Agents are on both the demand and supply sides. Platforms like Openlancer let agents post jobs, pitch, and pay each other, mostly via crypto.
A2H (Agent-to-Human): Agents are the demand side, humans are the supply side. RentAHuman launched on February 2nd and has gotten some traction, pulling in 70,000 signups. Agents browse human profiles and book people at $5–$500/hour for real-world tasks.
H2A (Human-to-Agent): Humans are the demand side, agents are the supply side. Moltverr is already live: humans post jobs, agents apply, best pitch wins.
So which model will take off? I think it is too early for A2A, and I am unsure of its current real-world use cases (maybe small micro transactions). I'm betting H2A and A2H are the two models that scale with H2A scaling first. It works like hiring already works; you have a job, you find the best candidate, except now the candidate pool includes agents that work 24/7 at a fraction of the cost. That said, Yonder portfolio company FeltSense is pushing the A2H model to its limits. Marik Hazan just raised $5.1M to build AI agents as fully autonomous founders. FeltSense has agents creating and running a business, and hiring humans as needed along the way!
We are in the early innings of the next generation of marketplaces, but I am still not sure we are there yet. OpenClaw agents are far too difficult for the vast majority of people to use and are rife with security vulnerabilities. We took a huge leap, but as with all things, the last mile of adoption is always the longest.
If you know of any cool agent-led marketplaces, please share in the comments!
While agent-led marketplaces represent the future, traditional marketplaces are thriving in the present, especially compared to their SaaS counterparts.
🔥 The Highlight
SaaS Is Getting Crushed. Marketplaces Are Not (for the most part).
AI is software on steroids, and no surprise, it's eating the world, and it largely is a net positive tailwind for marketplaces. I've been saying this for a while now, and one might even call me a perma marketplace bull, but the public markets are making the case better than I ever could, and my good friends at FJ Labs illustrated this well.
My other friends at SNAK Venture Partners dug even deeper into the data. Over the last 12 months, WCLD (the cloud SaaS ETF) is down -31.2%, with Adobe and Salesforce both off -42.5%. Meanwhile, horizontal marketplaces like eBay, Alibaba, and MercadoLibre averaged +15.1%, and asset marketplaces like Carvana were up +25.9%. An equal-weighted basket of marketplace stocks (excluding labor) outperformed WCLD by more than 30 percentage points.
In my opinion, the reason is structural. AI improves efficiency, automates workflows, and reduces headcount, which sounds great until you realize those are the exact things SaaS customers are paying for. SaaS sells a workflow (which requires people) while AI sells an outcome, which is great for marketplaces!
"Enterprise software companies charge recurring subscription fees for access to software that helps people do their jobs. If AI agents can do those jobs directly—or if foundation models make bespoke software irrelevant—the subscription fee disappears. Marketplaces, with their network effects and transaction-based revenue, are structurally harder to disrupt in this way." - Sonia Nagar of SNAK Venture Partners
For marketplaces, the economics run the other way: more efficient marketing, lower per unit costs, better matching, smarter pricing, lower CAC, etc. Every AI improvement drives efficiency at the transactional level, which, in turn, means better margins (a huge generalization, but it's directionally right).
The dividing line isn’t really marketplace vs. SaaS; it’s whether AI replaces what you sell with an actual outcome, or helps you improve what and how you sell.
I'm seeing this dynamic validated in the venture funding marketplace, too. Early-stage marketplace deals are picking up meaningfully, suggesting investors are cycling back into the category. I have been here all along, but it’s nice to see a focus on the defensibilities that marketplaces offer.
📰 News
Announcements
“Our approach to advertising and expanding access to ChatGPT” - OpenAI announced plans to test ads in ChatGPT’s free and Go tiers, promising that ads will never influence answers. It is a pivotal moment for how AI-mediated commerce will work and for whether OpenAI can build an ad model fundamentally different from those that came before. OpenAI
“ChatGPT's 4% Fee Confirms Marketplace Economics” - Shopify confirmed merchants will pay OpenAI a 4% fee on ChatGPT checkout sales, bringing all-in costs to roughly 9%, still well below Amazon's 25%+, and with conversion rates nearly 9x higher than Google organic. Marketplace Pulse argues this makes ChatGPT the first organic discovery channel at scale since Amazon's ad business killed unpaid visibility. Marketplace Pulse
“Google makes Etsy and Wayfair items shoppable within agentic AI search” - Google’s Universal Commerce Protocol now lets users buy Etsy and Wayfair items without leaving Google Search or Gemini, marking a major milestone in agentic commerce, going from concept to reality and creating both opportunity and existential questions for marketplace operators. Retail Brew
“Public and Autopilot Partner to Bring a New Model of Managed Investing to Retail Investors” - Public partnered with Autopilot (creators of the viral Pelosi Stock Tracker) to offer managed investing strategies, blending the marketplace model with creator-driven finance. PR Newswire
“We launched Zumper’s app on ChatGPT today!” - Zumper became the first rentals-only app live on ChatGPT, allowing users to browse rental inventory conversationally. LinkedIn
“’Grubhub Will Eat the Fees’: George Clooney and Yorgos Lanthimos Lead the Brand’s Big Game Debut, Redefining Restaurant Delivery with New No-Fee Benefit” - Grubhub made its first-ever Super Bowl appearance, announcing it will permanently eliminate delivery and service fees on restaurant orders over $50 to grab market share. Multivu
“We’re honored to be named the Exclusive Prediction Market Partner of the Wall Street Journal & the Dow Jones.” - Polymarket continues its march toward mainstream legitimacy with a landmark media partnership, proving that prediction markets are becoming embedded infrastructure for how we consume and trust information. X
“Known dating app launch” - Known launched in San Francisco as a post-swipe dating platform designed around intentionality and getting people on real dates, and another entry in the growing wave of dating startups challenging the incumbent model. X
Updates
Airbnb just reported Q4 earnings. GBV up 16%, our strongest growth in over two years." - Brian Chesky shared a thread breaking down Airbnb's Q4 results and the operating philosophy behind them: small teams, obsessive focus, and a two-year internal initiative called Project Hawaii that eliminated cleaning fees, simplified booking, and removed low-quality listings. The result is ~40% free cash flow margins and nearly $19B in free cash flow generated since IPO. X
“FJ Labs Q4 2025 Update” - Fabrice Grinda’s quarterly update is always worth reading: highlights include Vinted accelerating through €10B GMV and €1B revenue while highly profitable, Numerai raising $30M at a $500M valuation, and Refurbed approaching €1B GMV. Fabrice Grinda
“Update on Micro1: $200M RR now” - Micro1, the AI talent/data labeling marketplace, hit $200M in recurring revenue, a 2x jump in roughly 3 months, with a $100M round coming together. X
“CharterUP 2025 Recap: Year in Review” - CharterUP surpassed $2B in platform volume, completed 128,000 trips, and served 6M passengers across 12M miles traveled. LinkedIn
“Language learning marketplace Preply’s unicorn status embodies Ukrainian resilience” - Preply hit a $1.2B valuation after raising $150M in Series D funding, reaching EBITDA profitability after 12 months while maintaining 150 employees in Kyiv despite the ongoing war. TechCrunch
“Recap of 2025, as a first-time founder” - SideShift founder Nicholas Lawton shares a first-year recap: 800K creators on the platform, 700+ brands, $10M+ paid out to creators, and 25B+ views generated, demonstrating the explosive growth potential in the UGC/creator economy marketplace. X
“January was a record breaking month for Whop” - Whop posted January numbers: $240M+ earned by users globally, 50K daily signups, 252K businesses created, and 140% 12-month NRR. X
"Rejigg crosses $100M in transaction volume and raises $10.5M to build the future of SMB M&A" - Barrett Glasauer and Alex pulled the curtain back on what they've been building at Rejigg: $100M+ in platform transaction volume, $3B+ in businesses listed, 6X YoY growth in 2025, and a $10.5M raised. Be sure to watch the video. LinkedIn
Acquisitions
“eBay to Acquire Depop from Etsy for $1.2B in Cash” - eBay is buying secondhand fashion marketplace Depop for $1.2B which is a 26% haircut from the $1.62B Etsy paid five years ago, but a bet on a platform doing nearly $1B in GMS with 60% YoY U.S. growth and 7M active buyers, nearly 90% under 34. Fashion already generates $10B+ in annual GMV for eBay, and Depop gives them the younger, mobile-first audience. Etsy
“Rover Group Acquires Cat-Centric Marketplace, Meowtel” - In a classic vertical marketplace roll-up play, the world’s largest online pet care marketplace acquired the #1 cat sitting marketplace, which has grown to over 4,000 providers serving 125,000+ cats across 8,000 cities. Rover.com
People
“The AI Talent Wars Have Hit Data Labeling” - Mercor is offering $500K-$2M signing bonuses to poach micro1 employees, extending the AI talent wars from researchers into sales and operations roles at data-labeling marketplace companies.
So far, there’s no public sign that Mercor has successfully poached micro1 staff. According to LinkedIn, no one has yet made the jump. In one message viewed by Forbes, a micro1 employee rejected the pitch outright.
“Get out of here,” he replied. Forbes
“Airbnb announces Ahmad Al-Dahle as Chief Technology Officer” - Airbnb hired the former head of Meta’s Generative AI group (the team behind Llama) as CTO, with Brian Chesky framing the hire around making technology serve human connection and a signal that Airbnb’s AI strategy will be deeply integrated into the core marketplace experience. Airbnb
“Amir Nathoo Steps Back from Leading Outschool” - After 11 years, Outschool’s founder steps down from the education marketplace he built to 100,000+ live online classes serving 1M+ learners across 196 countries. LinkedIn
“Excited to share that I’ve joined Bounce as the first Chief Growth Officer.” - Andrew Tweed joins the luggage storage marketplace, which has already expanded to 100 countries with 35,000 locations backed by a16z and General Catalyst. LinkedIn
💰 Fundraising
Another raises $2.5M seed led by Anthemis Female Innovators Lab Fund - Another’s retail marketplace targets inventory liquidation, helping brands and retailers efficiently offload surplus stock.
FeltSense raises $5.1M - The round had participation from Draper Associates, Precursor Ventures, Liquid2 Ventures, Yonder (🎉), and angels including Matt Schlicht (Moltbook), Jager McConnell (Crunchbase), and Peter Green (Republic).
Noise Announces $7.1M Series Seed Led by Paradigm - Noise raised a $7.1M seed round led by Paradigm, further validating the growing intersection of crypto infrastructure and marketplace models.
Ditto AI raises $9.2M seed round - Ditto AI is building an agentic social network focused on college dating, leveraging AI agents to automate match-making and date coordination with early viral adoption in university communities.
When raises $10.2M Series A to transform employee health benefits - When provides a workforce transitions platform offering an AI-powered marketplace for affordable healthcare coverage alternatives during employment changes. EINPresswire
Konnex raised $15M - Konnex is building a marketplace for autonomous robots that work like apps, contracted, verified, and paid, an ambitious bet on the future of physical labor marketplaces. X
Plug raises $20M Series A led by Lightspeed - Plug is building a real-time marketplace specialized in electric vehicle inventory, focusing on pricing transparency and rapid transactions to stabilize residual values in the growing EV market. LinkedIn
Hiive completes Series B on its own platform - Hiive, a private stock marketplace, completed its own Series B funding round using its own platform, a remarkable proof of concept that closed in just 6 weeks, including a record-setting $500M in December transaction volume alone. LinkedIn
Buy&Ship closes $12M Series C - Buy&Ship is a cross-border e-commerce enabler that uses AI-driven logistics and discovery to streamline international shopping, and is aggressively expanding into the U.S. market. HKSTP
Solace Health raises $130M Series C at a $1B valuation - Solace Health operates a patient advocacy marketplace that connects registered nurse advocates with patients to navigate complex healthcare, monetizing via Medicare reimbursement shares. EINPresswire
🥳 Yonder Fund I raises $4.64M to back marketplace founders - Yonder Fund focuses on early-stage marketplaces building new economies with embedded SaaS, fintech, and managed services to enhance defensibility and network effects. Yonder
📖 Reads
“Runnin’ Down A Dream” - Bill Gurley has written a new book, not about marketplaces, but about finding a career you love, which I am enjoying reading. I was lucky enough to hear him talk about it at the Future Titans conference put on by the one and only Daniel Dart (thank you for the copy of the book!). Amazon
“Top tips for founders building marketplaces in the AI era” - Olivia Moore at a16z shared her framework for how marketplaces are evolving in 2026, drawing on lessons from Airbnb, Instacart, and Whatnot. Required reading for marketplace founders! X
"Magic Tricks, Moats, and the Three-Body Problem of AI Networks" - Casey Winters argues that most AI consumer products today are "magic tricks"—novel but shallow—and that the real winners will optimize for structure and compounding density rather than virality, drawing parallels to the mobile era where Instagram and Uber came years after the initial App Store hype. Casey Accidental
"The Software Shakeout: What Is Durable and What Is Not in the Age of AI?" - Dan Hockenmaier's framework for which software companies survive the AI shakeout comes down to two questions: how hard is it for customers to switch, and does the product's value compound with scale? The real pressure is an explosion of competition from every direction: startups building cheaper, platforms verticalizing, incumbents moving horizontally, and customers shifting budgets from subscriptions to tokens. Dan Hock's Essays
"How DoorDash solved problems, pt 2." - Steve Kenning continues his series on DoorDash's operational playbook, this time on scoping solutions. His framework is simple: there are only three types of solutions to an operational business problem: add more people to do more of the same stuff, change a process so people are forced to do different stuff, or build a product so people don't have to do stuff anymore. Great example of how DoorDash Catering cut average delivery times by questioning whether to optimize the distribution, cut off the long tail, or delete the distribution entirely. Missing & Incorrect
“OpenAI Wants to Buy Pinterest?” - Speculation that OpenAI might acquire Pinterest for $17B highlights a fascinating strategic logic: OpenAI has the world’s best AI but almost no commerce data, while Pinterest processes 600M users doing 80B visual searches monthly (a lot of it with purchase intent). AI for E-commerce
“At what point do we agree you’re no longer a ‘prediction market’” - A timely question as Polymarket expands into media partnerships, sports betting, and financial markets, blurring the line between prediction market, exchange, and information platform. X
“Where Ambition Meets Guidance: The Growth Story Behind Leland” - Forbes profiles Leland, a coaching marketplace building real relationships between ambitious professionals and experienced coaches, showing how services marketplaces can thrive by going deep on trust and outcomes rather than competing on volume. Forbes
“No Hangover and Hard Abs: Welcome to Newest Kind of Partying” - The rise of “soft partying,” e.g. sober-curious social events, fitness meetups, and intellectual gatherings, is spawning a new wave of marketplace and community-building startups like Sweatpals ($16M raised), Offline, and Matinee Social Club, as young adults trade hangovers for genuine connection. Business Insider
📽 Watch or Listen
“Airbnb Co-Founder and CEO Brian Chesky says more AI founders should be starting consumer businesses.” - Chesky points out that 87% of Y Combinator companies are enterprise-focused, arguing the biggest prize is consumer AI—the kind that makes daily life easier for billions of people. LinkedIn
THE DART BOARD ep #35: Bill Gurley | Benchmark - Bill Gurley shares insights on building enduring businesses, the compounding nature of obsession and learning, and the transformative impact of AI on careers and marketplaces.
Keith Rabois and Eric Newcomer’s Heated Conversation on Tech, Trump, and Tariffs - Rabois discusses Ramp’s vision, AI investment theses, and the intersection of tech, politics, and ethics in today’s venture landscape. But most importantly, talks a bit about AI and marketplaces at 10:09.
"Starting & Scaling Hipcamp With Alyssa Ravasio | EM Group Chat #205" - Alyssa Ravasio, Founder & CEO of Hipcamp, breaks down how she built the largest marketplace for booking campsites, RV parks, and unique outdoor stays. from solving the cold start problem through education-first supply onboarding to scaling past $90M+ raised from a16z, Benchmark, and Index Ventures. Great discussion on how supply drives demand, bootstrapping before venture capital, and why network effects in outdoor stays look different from those in traditional travel marketplaces.
Thanks for reading!
That is a wrap for the week! As always, please email me at colin@yonder.vc with any feedback or news I missed. Hot tips are always welcome. Please don’t forget to subscribe and follow me on X and LinkedIn for other great marketplace content. If you’d like to schedule a call, you can find me on expert marketplaces Hubble or Intro.
Power your marketplace with...
Whop Payments Network – Best rates, embedded checkout, global payouts, 24/7 human support, and a whole lot more.
I am thrilled to be partnering with Whop to share an EXCLUSIVE OFFER:
Get your first $200K in volume processed for free.
Accept Card, ACH, Venmo, Crypto, and more with one embedded checkout
Instantly pay out globally in ACH, Venmo, PayPal, & crypto.
Join the network trusted by innovators like Micro1, SideShift, and Metafy.
Learn what the hype is about and claim your benefits here.
About Me:
Colin is a marketplace geek and the General Partner of Yonder, a pre-seed marketplace fund that invests in marketplaces that create new economies. He has also been a longtime advisor to marketplaces, helping them with product growth, monetization, liquidity optimization, and strategy. Previously, he served as the CPO/CRO at Outdoorsy and has worked at Tripping.com, Ancestry.com, JustAnswer, and the Federal Reserve.
Beast of an article, thanks for sharing Colin!
Great Memo! So many wins on the marketplaces frontier 📈