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Managing Follow On Investment Decisions

ASecurity

Evaluates pro-rata and follow-on investment decisions with portfolio construction, signaling effects, and reserve management. Use when making follow-on decisions, managing reserves, or evaluating pro-rata rights.

22 stars
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Added 9/20/2026
businessapiperformance

Works with

cliapi

Security Analysis

A100/100

Scanned 9/20/2026

Install to Claude Code

$npx -y skills add lev-os/agents --skill managing-follow-on-investment-decisions --agent claude-code

Installs into .claude/skills of the current project.

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SKILL.md
---
name: managing-follow-on-investment-decisions
description: Evaluates pro-rata and follow-on investment decisions with portfolio construction, signaling effects, and reserve management. Use when making follow-on decisions, managing reserves, or evaluating pro-rata rights.
tags:
  - management
  - venture-capital
  - investment
  - portfolio
metadata:
  author: casemark
  practice_areas:
    - Venture Capital
    - Seed/Series Investing
    - Startup Ecosystems
  document_types:
    - Management Report
  skill_modes:
    - Management
    - Coordination
---
# Managing Follow On Investment Decisions

## When To Use

- A portfolio company is raising a new round and you hold pro-rata rights
- Reserve allocation review is due (quarterly or triggered by upcoming round)
- Evaluating whether to lead, participate, or pass on a follow-on opportunity
- Assessing signaling risk of declining to participate in a round
- Rebalancing fund reserves across the active portfolio

## Inputs To Gather

- **Portfolio company data**: current round terms (valuation, structure, lead investor), prior round terms for each investment, cap table with your current ownership percentage
- **Company performance**: revenue trajectory, burn rate, runway, KPIs relative to plan at time of last investment
- **Fund-level data**: total fund size, capital deployed to date, remaining reserves, number of active portfolio companies, target reserve ratio
- **Pro-rata rights**: confirm contractual right to participate (from side letter, investor rights agreement, or ROFR provisions) and any expiration or exercise deadlines
- **Round dynamics**: identity of lead investor, round size, whether existing investors are participating, any pay-to-play provisions [VERIFY]
- **Co-investor sentiment**: indications from syndicate partners on their participation plans

## Workflow

1. **Confirm pro-rata entitlement and deadlines**
   - Pull the relevant clause from the investor rights agreement or side letter
   - Note the exercise window and any notice requirements
   - Flag pay-to-play consequences for non-participation [VERIFY — terms vary by deal]

2. **Assess company performance against original thesis**
   - Compare current metrics to the underwriting case at initial investment
   - Identify thesis-breaking changes (market shift, team departure, competitive loss) vs. thesis-confirming signals (revenue growth, retention, market expansion)
   - Score conviction: high / moderate / low

3. **Evaluate round terms and dynamics**
   - Benchmark valuation against comparable rounds (stage, sector, geography)
   - Assess round structure for investor-unfriendly terms (heavy liquidation preferences, ratchets, participating preferred)
   - Identify the lead investor and their track record — a strong new lead at a fair price is a positive signal

4. **Model ownership and return impact**
   - Calculate current ownership and post-dilution ownership if you pass
   - Model pro-rata participation: dollar amount required, resulting ownership, and implied return at target exit scenarios (1x, 3x, 5x fund returner thresholds)
   - Compare marginal dollar return of this follow-on vs. deploying the same capital into a new deal or another portfolio company's follow-on

5. **Analyze reserve budget and portfolio-level trade-offs**
   - Map remaining reserves against anticipated follow-on needs across the portfolio
   - Rank portfolio companies by conviction and expected capital need over the next 12–18 months
   - Determine if participating here forces you to pass on a higher-conviction follow-on later

6. **Assess signaling risk**
   - If your fund is a known, lead, or significant investor, declining sends a negative signal to the market
   - Quantify the risk: Will other investors read non-participation as a lack of confidence? Could it impair the company's ability to close the round?
   - Consider partial participation (less than full pro-rata) as a middle path — maintains presence while conserving reserves

7. **Formulate recommendation and document rationale**
   - Decision options: full pro-rata, partial participation (specify amount), or pass
   - For each option, state the ownership outcome, reserve impact, signaling effect, and key risk
   - Present to the investment committee with a clear recommendation and the supporting analysis

## Output

Produce a **Follow-On Investment Decision Memo** containing:

- **Company snapshot**: name, stage, sector, current round terms, lead investor
- **Ownership table**: pre-round ownership, pro-rata amount, post-round ownership (participate vs. pass)
- **Performance assessment**: 3–5 bullet summary of company trajectory vs. original thesis
- **Return modeling**: scenario table showing implied returns at 1x, 3x, 5x exit multiples for participate vs. pass
- **Reserve impact**: current reserve balance, draw-down from this follow-on, remaining reserves, and coverage ratio for other anticipated follow-ons
- **Signaling analysis**: 1–2 sentences on market perception risk
- **Recommendation**: participate (full/partial) or pass, with one-paragraph rationale
- **IC action items**: approval required, exercise deadline, wire instructions or next steps

## Quality Checks

- Ownership math ties to the cap table and round terms — verify dilution calculations independently
- Reserve projections account for all portfolio companies with upcoming rounds, not just this one
- Signaling analysis reflects your fund's actual visibility and role (lead vs. passive participant)
- Pay-to-play and pro-rata terms are confirmed against the actual agreement, not assumed [VERIFY]
- Return scenarios use defensible exit assumptions grounded in comparable transactions, not aspirational targets
- Recommendation clearly states the trade-off being made and does not present the decision as risk-free

Attribution

lev-oslev-os
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