Oct 11, 2023 · 54m · news
Roundtable #4 with Jason Lemkin, Woody Marshall, Deven Parekh, Harry Stebbings | E1071 · 20VC with Harry Stebbings
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
A digital roundtable of prominent venture capitalists and investors discusses the shifting realities of growth-stage investing, navigating the hangover of inflated 2021 valuations, and the long-term outlook for the newly reopened tech IPO market.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 8.2% of the talking time here. How this is scored →
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Woody directly counters Harry's anecdote from a trillion-dollar asset manager, flatly stating 'I don't. I don't' and attributing aftermarket performance to small floats and macro headwinds.
Hardest push from Harry ▶ 40:19 Harry challenges guest optimism using a $1T asset manager's critiqueHarry refuses to accept the guests' positive framing of recent tech IPOs, bringing in direct quotes from an asset manager who characterized all three offerings as lackluster.
Biggest teaching moment ▶ 16:37 Deven schools Jason on how structured terms ruin M&A alignmentDeven reframes Jason's naive defense of structured terms by demonstrating how a guaranteed 2x liquidity structure blocks sensible mid-tier strategic M&A acquisitions.
Harry holds his own ▶ 31:34 Harry uses market data to challenge the IPO window timelineHarry demonstrates strong market expertise by connecting 6x ARR public trading multiples with frozen late-stage growth rounds to argue for a delayed 2025 IPO window.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Roundtable Participant Introductions | 1 | 0 | 0 | 0 | Standard intro round where Harry quickly welcomes the panelists and has each guest summarize their firm background and role. | |
| The State of Growth Investing and Deal Pacing | 2 | 4 | 1 | 1 | Harry prompts with the general belief that growth investing is dead. Deven reframes this by providing portfolio data showing solid underlying company growth despite slower deal pacing. | |
| Scaling Into High Valuations and Option Realignment | 4 | 4 | 2 | 3 | Harry asks a targeted question about whether 100x ARR valuations create scaling issues and if team equity gets wiped out by liquidity preferences. Deven and Woody explain option resetting dynamics. | |
| The Debate on Structured Terms in Funding Rounds | 1 | 6 | 4 | 0 | Co-guest Jason challenges the consensus against structured terms, while Harry remains passive. Deven and Woody educate Jason on how 2x liquidity structures create severe M&A misalignment. | |
| VC Write-Downs and LP Alignment | 5 | 5 | 2 | 4 | Harry challenges the panelists on VC delay in marking down books to protect LP fundraising. Deven uses an Ivy League admissions analogy to explain public multiple shift toward profitability. | |
| Can a 6x ARR Multiple Sustain the Growth Market? | 6 | 5 | 3 | 5 | Harry cites 6x ARR public baselines and argues that frozen late-stage growth rounds will push the IPO window back to late 2025. Deven counters Harry's premise, taking Jason's side for late 2024. | |
| IPO Pricing, Execution, and Public Market Realities | 2 | 4 | 1 | 1 | Woody and Deven explain why recent tech IPOs were priced small to put the puck on the ice. Jason asks how late-stage firms discuss down rounds internally while Harry listens. | |
| Venture Capital Risk Culture and Internalizing Mistakes | 7 | 5 | 5 | 6 | Harry pushes back on guest optimism by quoting a top asset manager who called recent tech IPOs lackluster. Woody forcefully disagrees, citing low floats and high short interest. | |
| The Economics of High-Quality SaaS Startups | 2 | 3 | 2 | 1 | Jason asks if high-profile SaaS IPOs should take one for the team by pricing lower to restart the market. Deven and Woody explain why leaving money on the table causes editorial backlash. | |
| Late-Stage AI Valuation Hype Cycle | 4 | 3 | 2 | 2 | Harry queries the panelists on late-stage AI valuation frothiness. Deven confirms Insight avoided AI deals in 2023 due to a valuation hype cycle. | |
| Case Study: Is a 50/50/0 SaaS Company Fundable? | 2 | 4 | 1 | 1 | Jason presents a hypothetical 50/50/0 startup case study to ask about growth multiples. Deven notes valuation depends on 5-year compounding durability rather than current multiples alone. |