The Perch: September Issue

We’ve spent the last several days on the road across New York (Primary Summit), the Middle East, and Asia, where we’ve heard sharply divergent sentiments among founders and investors on the AI landscape.

We find ourselves somewhere in the middle. On one hand, the total addressable market created by AI is both vast and unprecedented. Its utility is already evident, reflected in real revenues rather than speculation, and there remains significant, obvious ground to cover (agents, for instance, are still in their infancy). At the same time, we recognize that many of today’s $1B+ AI companies may not prove enduring. Competitive moats remain unclear across much of the landscape, suggesting that pricing and margins will compress over time, while valuations for perceived category leaders can quickly become inflated. Against this backdrop, we continue to study opportunities and emerging trends with an open, but disciplined, lens.

Trend Watch: Payments × AI Agents

The current payments infrastructure was designed for humans — and, in many ways, to keep bots out.

This paradigm is shifting. Autonomous agents are beginning to function as economic actors. Consumers are already using tools like OpenAI Operator and Perplexity Shopping to discover and transact — e.g., “ChatGPT, find a two-night experience for my wife and me over Labor Day weekend under $500.”

Because agents transact differently — searching across vastly more catalogs, splitting purchases across multiple merchants, operating without a human or card present, and enabling one-to-many workflows — we believe a new payments stack will emerge. This stack will be defined by instant settlement, seamless reconciliation, and significantly greater scalability.

Two early blueprints have begun to take shape: Stripe’s Tempo (regulated, merchant-focused) and Coinbase’s x402 (open-source, composable, and more web3-native). Incumbents are also moving quickly — Visa has launched VisaPay, Mastercard announced AgentPay, and Shopify recently introduced an agent development kit.

We view this as a massive opportunity. Pre-agent infrastructure companies have already produced category-defining outcomes — Stripe (~$90B) and Adyen (~$50B+). We believe the addressable market for agentic payments could be materially larger, driven by lower friction and the proliferation of nano-transactions. The space remains early and is currently dominated by agile incumbents, but we are watching it closely.

Portfolio

In recent months, we have joined cap tables alongside General Catalyst, NEA, Kleiner Perkins, NFX, Sequoia Arc, and Lightspeed. With each investment, our reputation continues to strengthen — as does our right to win.

We have made fourteen investments to date, all at the pre-seed or seed stage, backing exceptional global engineers applying AI to solve meaningful problems. A few highlights:

• Anterior (entry at $15M cap) raised a Series B at a $250M post-money valuation, led by a top-tier firm

• Antes (stealth) raised a $3.5M follow-on seed round led by Jeanette at General Catalyst

Community

We continue to invest in building meaningful founder communities. These efforts have delivered tangible value — from expanding our pipeline to helping portfolio companies recruit talent.

• In June, we hosted a fireside chat with AJ Tennant (former VP of Sales at Glean) on scaling an AI company to $100M ARR in under two years, followed by a private dinner with 35 founders

• We co-hosted founder dinners in San Francisco with Brex (B2B payments) and Rho for pre-seed and seed-stage companies

• In August, conversations with Indian-origin founders highlighted a recurring gap: the lack of community in the first 500 days. We are actively exploring ways to address this need.

  
  

  

Closing Thoughts

The opportunity ahead is larger than we initially anticipated. It is increasingly likely that, in a few years, we will look back and wish we had invested more aggressively.

Co-Investment Opportunity

We are currently evaluating a co-investment opportunity in a portfolio company demonstrating strong momentum:

• ~$40M revenue run-rate

• ~20% margins

• ~70% of revenue from repeat customers

• Targeting $100M run-rate by year-end

The addressable market is effectively uncapped, with a credible path to category leadership. We have up to ~$3M of allocation within a targeted $50M round and would be happy to discuss further on a one-on-one basis.

Team ODDBIRD