Where you start seeing structure in deals is in deals is when a founder is trying to preserve a valuation they got last year... you'll start to see them happen later this year when companies get more desperate.View on YouTube
Multiple independent data points show that, as 2022 wore on and funding conditions tightened, startups increasingly used structured terms (especially enhanced liquidation preferences) to preserve prior high valuations rather than accept headline down rounds.
- In June 2022, TechCrunch reported that many Series A/B companies that had raised at rich 2021 valuations were now doing “overly structured flat and extension rounds” instead of clean down rounds, and that these structured deals were “the most common thing we’re seeing at this moment.” The article describes investors adding punitive terms (e.g., high liquidation preferences, participating preferred) explicitly to avoid reducing the last round’s valuation. (techcrunch.com)
- On SVB Financial Group’s Q3 2022 earnings call, management said: “right now, we’re not seeing a lot of down rounds, we’re seeing more structured rounds,” explaining that companies were keeping the same price but adding a 2x liquidation preference and similar terms. This was described as what they were actively seeing in late 2022, and framed as a way to protect valuations while markets reset. (nasdaq.com)
- Carta’s "State of Private Markets" data for Q1 2019–Q2 2023 show that the share of rounds with investor‑friendly terms like liquidation multipliers and participating preferred rose to unusually high levels by late 2022 / early 2023 (8.2% of rounds in Q1 2023, 6.1% in Q2 2023), which the report characterizes as elevated “when the venture market tightens up and funding is harder to find.” (carta.com) This implies a marked increase in structured deals versus the 2019–2021 period.
- Valuation Research Corp’s analyses of the post‑2021 downturn note that down rounds reached multiyear highs in 2023, but that statistics undercount effective down rounds because many companies chose flat or structured financings instead. They state explicitly that the number of structured new rounds—featuring downside protection, cumulative dividends, and liquidation preferences at multiples of the original issue price—was increasing, used to avoid marking headline valuations down even though economics were equivalent to a down round. (valuationresearch.com)
- Follow‑on commentary in 2023 describes structured term sheets as “back in vogue”, with new investors demanding liquidation preferences up to 4x as an alternative to cutting valuations, again confirming the pattern sacks described—structure used to mask what would otherwise be down‑round pricing in a tougher market that began in 2022. (techcrunch.com)
Taken together, these sources show that starting in mid‑ to late‑2022, as startups that had raised at peak 2021 valuations ran into a much tougher funding environment, there was a clear, noticeable increase in structured rounds with features like multiple liquidation preferences and other preferences used specifically to preserve prior valuations. That matches sacks’s prediction on both timing (“later this year”) and mechanism (structure used to avoid down rounds), so the prediction is best judged as right.