ExpertsFMRamtin Naimi - The State of Venture - [Invest Like the Best, EP.499]
Invest Like the Best with Patrick O'Shaughnessy · November 6, 2026
5 Selected Lessons:
case · 3 heuristic · 2
Compare growth within your company's revenue 'style', not against the headline leaders
Source
Invest Like the Best with Patrick O'Shaughnessy — Ramtin Naimi - The State of Venture - [Invest Like the Best, EP.499] (November 6, 2026) · at 3:05 ▸
When this applies
when benchmarking performance against public 'best in class' numbers that may not be apples-to-apples
The takeaway
Benchmark performance against peers with comparable economics and business structure, not against the most extreme headline numbers in your broader category.
Why it works
Headline growth rates often hide structural differences (margin profile, revenue type, customer concentration) that make direct comparison meaningless; the real comparison set is companies with the same revenue structure.
One level up
Decompose any eye-popping aggregate metric into its structural components before using it as a comparison standard.
Where it stops holding
This stops working when revenue structures genuinely are comparable — in that case the headline comparison is valid and this caveat is unnecessary.
Detail
rule: Compare your revenue growth to companies within your style of company, not to absolute top-line growth leaders.
threshold: Growth of 10-20x/year companies typically have some offsetting issue: low/negative margins, high customer concentration, annualized (not recurring) revenue, or consumer/usage-based revenue instead of enterprise contracts.
rationale: Without this adjustment, founders with normal (but healthy) growth wrongly conclude they are being left behind.
In their words
But I think if you peel back the layers and you start looking at it, you need to actually compare your revenue growth to companies within your style of company versus the absolute top line figures.
Being allocation-constrained (not capital-constrained) in your best deals is a sizing signal
Source
Invest Like the Best with Patrick O'Shaughnessy — Ramtin Naimi - The State of Venture - [Invest Like the Best, EP.499] (November 6, 2026) · at 38:03 ▸
When this applies
when reviewing your best past decisions and finding you were limited by permission/access rather than resources
The takeaway
When your limiting factor in your best opportunities has consistently been access/allocation rather than resources, that's a reliable signal you're under-resourced relative to your real capacity.
Why it works
If your fund's best-performing investments were capped not by lack of capital but by lack of allocation (not being allowed to invest more / not being the lead), that's direct evidence that more capital would have been straightforwardly deployable at the same quality in the past — a strong basis for raising a larger fund.
One level up
Diagnose constraints precisely — the type of constraint (resource vs. access) you repeatedly hit tells you exactly what to fix next cycle.
Where it stops holding
This stops working when the pattern of allocation-constraint was a one-off rather than a repeated pattern across many deals — a single instance isn't strong evidence of systemic under-capitalization.
Detail
rule: Check whether your best historical deals were limited by capital or by allocation/access.
rationale: Abstract's lion's-share-of-returns deals were almost all allocation-constrained, not capital-constrained — meaning they could have invested more and gotten more ownership if their fund size and lead-investor positioning had allowed it.
In their words
So, I think we have a lot of data points that support. We have very good relationship with a lot of the companies in our portfolio. We have great conviction in those companies, but historically, our fund size hasn't given us the option to be a lead investor in those financings.
GC's Customer Value Fund — debt tied to proven revenue-unlock ratio
Source
Invest Like the Best with Patrick O'Shaughnessy — Ramtin Naimi - The State of Venture - [Invest Like the Best, EP.499] (November 6, 2026) · at 16:00 ▸
When this applies
when a new financing product ties debt issuance to a provable, repeatable unit-economic ratio rather than generic covenants
The takeaway
A new capital structure gains adoption when it's tied to a clear, provable causal ratio between capital deployed and revenue generated, rather than abstract terms investors have to take on faith.
Why it works
By pegging debt size directly to a measurable output ratio ($X of debt unlocks $3X of revenue), the lender de-risks the loan while giving founders non-dilutive growth capital, making adoption easier once trust is established.
One level up
Financial innovation succeeds when it reduces to a legible, falsifiable unit-economics formula that both sides can verify.
Where it stops holding
This stops working when the revenue-unlock ratio isn't reliably provable or repeatable, or when VCs/founders default to resisting novel structures out of preference for clean equity.
Detail
situation: Founders needed growth capital without diluting equity to fund customer acquisition/compute spend.
decision: GC's fund offers debt sized to a proven ratio: every $10M of debt unlocks $30M of revenue.
outcome: The product has become 'enormously successful,' raising significant capital, despite early multi-year education effort needed to overcome VC skepticism of debt products.
lesson: Novel capital structures need both a legible value proposition and a persistence through an education/adoption curve before becoming standard.
In their words
It's like if you could prove that for every $10 million that unlocks $30 million of revenue, we'll give you the money to finance that.
Neolabs: huge capital needs, hard to underwrite, benchmark-maxing risk
Source
Invest Like the Best with Patrick O'Shaughnessy — Ramtin Naimi - The State of Venture - [Invest Like the Best, EP.499] (November 6, 2026) · at 18:50 ▸
When this applies
when a new category of capital-hungry companies proliferates and it's unclear whether their visible output reflects durable capability or optimized demos
The takeaway
When a category's public signal of quality (demos, benchmarks) can be optimized independently of real commercial value, be skeptical of using that signal alone to judge underlying quality.
Why it works
Because these companies' 'proof' of progress is impressive public demos/benchmarks, it's hard to distinguish genuinely generalizable breakthroughs from narrowly tuned benchmark performance that won't commercialize.
One level up
Any measurable proxy for success invites optimization toward the proxy rather than the underlying goal (Goodhart's law) — watch for this whenever a metric becomes the basis for capital allocation.
Where it stops holding
This stops working when a company's benchmark performance is independently validated against real commercial deployment, removing the proxy risk.
Detail
situation: Dozens of well-funded AI research labs are raising massive rounds, each claiming impressive demo results.
decision: Investors underwrite these companies despite difficulty discerning real generalizable progress from benchmark-tuned demos.
outcome: Unclear how many of the 80-90 will continue raising the capital they need — could be anywhere from 10% to 50%.
lesson: Treat benchmark-driven proof points skeptically in categories where capital allocation incentivizes benchmark optimization over real commercialization.
In their words
Oftentimes, it's hard to discern whether they're launching something that's truly impressive on a generalizable scale or if they launched something that was specifically tuned to perform really well on benchmarks.
Conduit and Etched — brilliant founders ahead of a market the market hasn't noticed yet
Source
Invest Like the Best with Patrick O'Shaughnessy — Ramtin Naimi - The State of Venture - [Invest Like the Best, EP.499] (November 6, 2026) · at 26:46 ▸
When this applies
when a clearly exceptional person chooses to dedicate years to a category that the broader market currently finds unimportant or implausible
The takeaway
The fact that a demonstrably brilliant person has chosen to dedicate a decade to a non-obvious category is itself strong evidence the category deserves attention, ahead of consensus recognition.
Why it works
Smart, well-informed founders often understand a market's future importance well before capital markets catch up; once a visible catalyst (e.g., a trusted lead investor, a hot comparable) validates the category, pricing re-rates sharply for everyone in it.
One level up
Trust revealed conviction of exceptional people over current market consensus as a leading indicator of category importance.
Where it stops holding
This stops working when the founder's brilliance doesn't translate to market-relevant execution, or when the category genuinely never becomes commercially viable despite the founder's talent.
Detail
situation: Conduit (BCI) and Etched (AI chip fabrication) founders were assessed by many top investors as brilliant, but the category itself was considered unimportant or unwinnable at the time.
decision: Ramtin backed Conduit at seed when nobody cared about BCI; other investors waited until Sequoia's $10B valuation of Etched made the chip category 'obvious' to invest.
outcome: Conduit later raised a highly oversubscribed round (13 term sheets) once BCI became a hot category; Etched's valuation triggered a repricing of the entire AI chip startup category.
lesson: The market being obvious to the founder before it's obvious to investors is the exact window where proactive investing captures outsized value.
In their words
I think smart people generally tend to understand markets well before the market starts to pay attention to them.