Take the dive | 99d Summary

Author: Yoni Rechtman, Partner at Slow Ventures

1. Key Themes

Theme 1: AI's Second-Order Effects Are the Real Investment Opportunity

The most actionable insight isn't AI itself — it's the downstream infrastructure breakdowns AI causes and the new systems required to replace them.

"AI amplifies volume until existing filtering/routing mechanisms collapse and need to be rebuilt."

"I'm extremely bullish on and interested in the second order effects of AI... the most interesting questions are what happens after we've done it."

Rechtman maps five specific collapse vectors: software deployment, hiring, outbound sales, code collaboration, and trust/security — each with portfolio companies already being built to address them.

Theme 2: Systems Infrastructure Is About to Flip — Scarcity and Abundance Are Inverting

A structural market shift is underway: things that were once scarce (content, code, applications, outreach) are becoming abundant, while attention and verification become the scarce resources.

"There are a huge number of spaces where attention (abundant) and production (scarce) will flip to devastating effect."

"Git was built for scarce, human-written code. Whatever replaces it will be built for abundance."

This framing implies entire software categories — version control, recruiting funnels, email security, sales tooling — are ripe for replacement, not just improvement.

Theme 3: SIs (Systems Integrators) Will Become a Dominant Force This Cycle

Deployment is the chokepoint, and Rechtman argues SIs — typically overlooked in venture — will capture outsized power.

"SIs are critical chokepoints and will become very powerful this cycle."

This is a specific, investable thesis: as AI accelerates software output, the humans and firms who manage integration and deployment become bottlenecks — and bottlenecks capture margin.

Theme 4: Trust and Online Authenticity Are a Systemic Infrastructure Problem

The internet's identity and content verification layer is breaking at scale.

"Everything on the internet is fake. Content, identities, credentials. Systems that assumed human-scale production and human-verifiable authenticity stop working."

Rechtman is backing companies like Outtake and Sublime Security in this space. The implication: this isn't a niche cybersecurity wedge — it's a fundamental rebuild of internet trust infrastructure.

Theme 5: Early Employees at Venture-Backed Companies Are an Underserved, High-Value Audience

Rechtman is launching Cliff Club, a community specifically for early employees at VC-backed startups, signaling a gap in structured resources for this cohort.

"We love getting together to hang with operators and builders early/earlier in their journeys, whether or not they wind up building companies. I find that much/most of our best network comes organically by hanging out and jamming with people months or years ahead of a transactable opportunity."

The community addresses real, unmet questions around equity (QSBS, early exercise), career structure, and role evolution — areas where early employees often lack quality guidance.

2. Contrarian Perspectives

Contrarian 1: The Current U.S. Productivity Boom Is Real — And Unexplained

The consensus productivity narrative ties recent gains to AI, but Rechtman pushes back, noting the boom predates AI's measurable economic impact — and nobody knows why it's happening.

"America is experiencing a productivity miracle and we basically don't know why. It's not because of AI (at least not yet) but it is really good news."

This is significant: if the productivity surge is structural and non-AI-driven, it changes assumptions about labor markets, rates, and the timing of AI's actual economic impact.

Contrarian 2: The Outbound Sales Channel Is Effectively Dead

While most sales teams are doubling down on AI-powered outbound, Rechtman argues the widespread democratization of sophisticated outreach is poisoning the channel for everyone.

"Sophisticated campaigns available to everyone, flooding channels. The well gets poisoned and new GTMs replace it."

The investment implication: the next GTM motion doesn't look like better outbound — it looks like something entirely different. He's backing Memelord (and a stealth company) in this space.

Contrarian 3: A U.S. Confrontation with Iran Risks Permanent Geopolitical Damage — Not a Recoverable Loss

Rechtman links to analysis arguing that a failed engagement with Iran would be categorically different from past American military setbacks.

"Defeat in the present confrontation with Iran will be of an entirely different character. It can neither be repaired nor ignored. There will be no return to the status quo ante... With control of the strait, Iran emerges as the key player in the region and one of the key players in the world... Far from demonstrating American prowess... the conflict has revealed an America that is unreliable and incapable of finishing what it started."

The geopolitical risk here — Iranian control of the Strait of Hormuz and a realignment toward China and Russia — would have severe energy market and global trade implications.

3. Companies Identified

Company	Description	Why Mentioned	Quote
Phoebe	Hiring/recruiting tech	Addresses AI-driven collapse of resume screening and candidate filtering	"Applications are free to send. Volume explodes. Recruiters can't distinguish candidates. Resume screening stops working."
MeritFirst	Hiring/recruiting tech	Same thesis as Phoebe — rebuilding the hiring funnel	Same as above
Tofu	Hiring/recruiting tech	Portfolio company in the hiring infrastructure rebuild space	Same as above
Memelord	Outbound sales / GTM	Addresses poisoning of traditional outbound channels by AI	"Sophisticated campaigns available to everyone, flooding channels. The well gets poisoned and new GTMs replace it."
Atomic	Code collaboration	Building the replacement for Git in an AI-abundant code environment	"Git was built for scarce, human-written code. Whatever replaces it will be built for abundance."
Outtake	Trust & security / content authenticity	Addresses collapse of content and identity verification at scale	"Everything on the internet is fake. Content, identities, credentials."
Sublime Security	Email/cybersecurity	Addresses AI-driven increase in sophisticated, hard-to-detect threats	Same as above
Cliff Club	Community for early startup employees	Rechtman's own initiative to serve early employees at VC-backed companies	"A community exclusively for early employees at venture-backed companies, starting in NYC."
Rho	Business banking / fintech	Hosted the podcast where Rechtman discussed his AI theses	Referenced as podcast host
Slow Ventures	Venture capital firm	Rechtman's firm, deploying from a ~$325M fund at pre/seed	"I lead pre/seed rounds from a ≈$325M fund."

4. People Identified

Person	Description	Why Mentioned	Quote
Yoni Rechtman	Partner at Slow Ventures, pre/seed generalist investor	Author; shares investment theses on AI second-order effects and seed-stage investing	"I'm a generalist investor looking for weird takes on important stories: N-of-1 companies taking non-obvious approaches to markets that matter."
Charley	Operator/entrepreneur (last name not given)	Co-building Cliff Club with Rechtman	"Really excited to work on this with my friends Charley and Leeor."
Leeor	Operator/entrepreneur (last name not given)	Co-building Cliff Club with Rechtman	Same as above
Stephen Miller	U.S. Deputy Chief of Staff for Policy & Homeland Security Adviser	Cited as the most powerful unelected person in America, architect of immigration policy	"Stephen Miller is surely the most powerful unelected person in America... he has had in shaping Trump's most hardline anti-immigration policies and rhetoric for the past decade."
Jimmy Fallon	Tonight Show host	Used as a cultural critique vehicle in the "Haterade" section	"Fallon acts as the high priest of a terrified optimism, his rictus grin serving as a shield against the encroaching silence of the real."

5. Operating Insights

Insight 1: Build Relationships with Founders Long Before a Deal is Possible

Rechtman's networking philosophy is explicitly pre-transactional — and he frames it as a competitive edge for investors and operators alike.

"I find that much/most of our best network comes organically by hanging out and jamming with people months or years ahead of a transactable opportunity. But we only earn the right to your time if we can be of service."

Tactical takeaway: For investors, this argues for structured community-building (like Cliff Club) as a deal-sourcing mechanism. For founders, it suggests engaging investors well before a raise — and choosing investors who offer value before a check is written.

Insight 2: Seed Investors Should Minimize Interference

Rechtman reduces his entire seed investing philosophy to a memorable maxim when describing his Rho podcast appearance.

"The right way to back seed founders [is to] give them money and don't fuck it up."

Tactical takeaway: Seed investors who over-engineer portfolio management, impose governance too early, or distract founders with board dynamics create drag. The best seed-stage value-add may simply be capital, conviction, and absence.

6. Overlooked Insights

Overlooked Insight 1: "Greenfield Opportunities That Would Have Previously Been Impossible or Unimportant"

Rechtman briefly flags an entire category of new business models that AI makes possible for the first time — but doesn't elaborate.

"Simultaneously there are greenfield opportunities that would have previously been impossible or unimportant."

This is a distinct investment bucket from the "infrastructure rebuild" thesis and deserves more unpacking. It implies entirely novel markets — not just AI-accelerated versions of existing ones — are emerging. Investors focused only on what AI breaks may be missing what AI creates from scratch.

Overlooked Insight 2: A New Project is Teased But Unnamed

Rechtman mentions a new project in the opening line but gives no detail — only a link.

"Very busy week with a lot cooking including a teaser for a new project. More to come soon."

Given his commentary on community-building, content, and operator networks, this could signal a new media property, fund vehicle, or platform beyond Cliff Club. Worth watching.