๐Ÿ“š Chapter 21Part V: Structural Advantage

Reading the Market Cycle

The cycle tempts you to do the opposite of what works. Discipline is knowing the difference.

TC
Trace Cohen
3x founder ยท 65+ investments ยท Author, The Value Add VC

Key Insight

Venture capital practitioners spend careers in 1-2 full market cycles. Understanding cycle dynamics โ€” which phase you're in, which decisions belong to each โ€” is one of the most valuable and least-taught skills in the industry. Expansion phases make discipline seem optional. Contractions reveal which companies have genuine revenue durability. The rule: expand your pipeline in contractions. Tighten ownership discipline in expansions. The cycle tempts you to do the opposite of both.

$621B
Peak global VC funding (2021 expansion peak)
2025
First year of net decrease in active VC firms since dot-com
>10,000
VC firms on paper in the US
<50%
Of those that are actively investing

The One-Cycle Problem

Most venture practitioners spend their careers in one or two full market cycles. A typical fund manager who raises Fund I at 35 might see three cycles over a 30-year career. The compressed nature of fund lifecycles means a manager's track record may reflect primarily one macro environment rather than full-cycle performance.

This creates a specific failure mode: confusing the performance of a specific cycle with the performance of a strategy. Managers who launched in 2018 and deployed through 2021 often saw extraordinary marks on everything โ€” not because their strategy was exceptional, but because rising markets lift all boats. Those same marks deteriorated when the cycle turned.

Expansion: What It Hides

In expansion phases, nearly every manager looks good. Marks rise. Capital is abundant. The feedback loop between investment activity and valuation appreciation obscures a lot. The danger isn't that expansions last too long โ€” it's that they make discipline seem optional.

The managers who emerge from expansions intact are those who held ownership discipline when competitive pressure pushed them to accept lower stakes, and who reserved capital for breakout signals rather than averaging down in companies that were marking up but not growing.

The 2021 Lesson

In 2021, global venture funding reached $621 billion. Some managers abandoned discipline under competitive pressure โ€” accepting lower ownership, writing bigger checks into later stage, raising larger funds than their strategy warranted. By 2023, many of those companies faced down rounds. Many of those funds were explaining underperformance to LPs. The 2021 vintage included excellent companies and capital badly misallocated under the assumption that the cycle would continue indefinitely.

Contraction: What It Reveals

Contractions are clarifying. They reveal which companies have genuine revenue durability and which were growing on loose underwriting and abundant capital. They reveal which fund models were built for the real exit distribution and which relied on optimistic assumptions that evaporate when the IPO window closes.

The current contraction is visible in the data. Per Sapphire Partners, 2025 marked the first year since the dot-com collapse that the venture industry experienced a net decrease in active firms. More than 10,000 venture firms exist on paper in the US, but fewer than half are actively investing. The rest are zombie funds โ€” carrying unrealized marks, collecting management fees on legacy funds, but functionally absent from the market.

The Counter-Intuitive Rules

The rules of cycle-aware investing are counter-intuitive. Expand your pipeline in contractions โ€” when there are fewer competing investors and better companies are more accessible. Tighten your ownership discipline in expansions โ€” when competitive pressure tempts you to accept terms that don't work.

The cycle tempts you to do the opposite of both. In contractions, fear makes you pull back from new investments when you should be leaning in. In expansions, FOMO pushes you to accept worse terms when you should be holding firm. The managers who understand this intellectually and can actually execute against it emotionally in real time are the ones who generate consistent performance across full cycles.

For investors with dry powder in a contraction: this is the vintage that tends to outperform. Deploy with discipline into the highest-quality surviving companies. The competition is thinner. The valuations are more honest. The founders who are still here are the ones who know how to operate under constraint.

Frequently Asked Questions

How do you identify which phase of the venture market cycle you're in?+
Expansion indicators: rising valuations at every stage, compressed due diligence timelines, founders receiving multiple competing term sheets, narrative-driven investing, managers raising oversubscribed funds quickly. Contraction indicators: longer diligence timelines, fewer competing offers, rising ARR thresholds at every stage, down round frequency, fund managers struggling to raise, IPO window closed. Recovery: selective discipline returning while activity picks up, valuations stabilizing, highest-quality companies attracting interest first.
Why do expansion phases make discipline seem optional?+
In expansion, nearly every manager looks good. Marks rise quarterly. Capital is abundant. The feedback loop between investment activity and valuation appreciation makes all decisions seem correct in the moment. The dangerous consequence: ownership discipline looks unnecessary when every deal is going up regardless, and moving to larger fund sizes looks smart when LPs want to give you more capital. Managers who maintain discipline during expansions are often outbid. In retrospect, they were right.
What opportunities do contractions create for disciplined investors?+
For investors with dry powder, contractions represent some of the best vintage-year opportunities: entry valuations reflect constrained sentiment rather than optimism, competition decreases (fewer investors competing for deals), companies that survive quality selection are often dramatically better positioned than marks suggest, and founders are more realistic about valuation expectations. Cambridge Associates consistently shows outperformance from funds raised during contractions โ€” the 2010 vintage (post-GFC) and 2023 vintage are positioned to follow this pattern.
What happened to the VC market in 2025?+
2025 marked the first year since the dot-com collapse that the venture industry experienced a net decrease in active firms, per Sapphire Partners. More than 10,000 venture firms exist on paper in the US, but fewer than half are actively investing. The rest are 'zombie funds' โ€” carrying unrealized marks, collecting management fees on legacy funds, but functionally absent. New fund formation fell below replacement rate. PitchBook's 2026 outlook called difficulty for emerging managers to raise 'the biggest risk in early-stage investing' โ€” and also the biggest opportunity for those who can.
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